掲載種別：研究論文（学術雑誌）   出版者・発行元：Elsevier {BV}  

A new 12-membered macrolide, symbiodinolactone A, was isolated from the culture broth of symbiotic marine dinoflagellate Symbiodinium sp. The gross structure of symbiodinolactone A was elucidated by spectroscopic analyses, and the relative configuration was elucidated by the J-based configuration analysis and density-functional theory calculations. Symbiodinolactone A is the new 12-membered macrolide possessing an E double bond between C-4 and C-5, a branched methyl group at C-7, and a 1,2,3-trihydroxybutyl group at C-11. Symbiodinolactone A is the first usual size macrolide and the first non-nitrogen-containing macrolide from dinoflagellate Symbiodinium sp. Symbiodinolactone A might be generated by the unexplained dinoflagellate polyketide biosynthetic machinery.

DOI： 10.1016/j.tetlet.2018.11.018

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掲載種別：研究論文（学術雑誌）   出版者・発行元：Elsevier {BV}  

A new indole alkaloid with the canthin-6-one skeleton, ishigadine A, has been isolated from an Okinawan marine sponge Hyrtios sp. The structure of ishigadine A was elucidated on the basis of spectroscopic analyses. Ishigadine A is a new canthin-6-one alkaloid possessing a hydroxy group, a 1,3-dimethyl-4-methylthioimidazolium, and a 1-propylguanidine. Ishigadine A is the third canthin-6-one alkaloid from sponges. Ishigadine A might be generated from L-arginine, L-histidine, and L-tryptophan. Ishigadine A exhibited moderate cytotoxicity against L1210 murine leukemia cells.

DOI： 10.1016/j.tetlet.2018.11.019

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記述言語：英語   掲載種別：研究論文（学術雑誌）   出版者・発行元：MDPI} {AG  

Two new bromotyrosine alkaloids, ceratinadins E (1) and F (2), were isolated from an Okinawan marine sponge Pseudoceratina sp. as well as a known bromotyrosine alkaloid, psammaplysin F (3). The gross structures of 1 and 2 were elucidated on the basis of spectroscopic data. The absolute configurations of 1 and 2 were assigned by comparison of the NMR and ECD data with those of a known related bromotyrosine alkaloid, psammaplysin A (4). Ceratinadins E (1) and F (2) are new bromotyrosine alkaloids possessing an 8,10-dibromo-9-methoxy-1,6-dioxa-2-azaspiro[4.6]undeca-2,7,9-trien-4-ol unit with two or three 11-N-methylmoloka'iamine units connected by carbonyl groups, respectively. Ceratinadin E (1) exhibited antimalarial activities against a drug-resistant and a drug-sensitive strains of Plasmodium falciparum (K1 and FCR3 strains, respectively).

DOI： 10.3390/md16120463

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記述言語：英語   掲載種別：研究論文（学術雑誌）   出版者・発行元：PERGAMON-ELSEVIER SCIENCE LTD  

The investigation of the Vietnamese marine sponge Spongia sp. led to the isolation of three new sesquiterpene phenols, langconols A-C (1-3), and one new sesquiterpene hydroxyquinone, langcoquinone C (4), together with two known meroterpenoids (5 and 6). Their structures were determined on the basis of spectroscopic analyses and comparisons with published data. Furthermore, the antibacterial assays of the isolates 1-6 suggested that 4 and 6 had significant antibacterial activities against Bacillus subtilis and Staphylococcus aureus, with MICs ranging from 6.25 to 25.0 mu M, while 1 and 3 possessed significant antibacterial activities against B. subtilis with MICs of 12.5 and 25.0 mu M, respectively. In contrast, cyto-toxic assays of the isolated compounds 1-6, as well as compounds 7-15 previously isolated from this sponge, indicated that 1 and the previously reported anti-B. subtilis and anti-S. aureus sesquiterpene phenol 9 lacked cytotoxic activities against three human cancer cell lines (A549, lung cancer; MCF7, breast cancer; HeLa, cervix cancer) and a human normal cell line (WI-38 fibroblast). (C) 2017 Elsevier Ltd. All rights reserved.

DOI： 10.1016/j.bmcl.2017.05.060

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記述言語：英語   掲載種別：研究論文（学術雑誌）   出版者・発行元：AMER CHEMICAL SOC  

A new manzamine alkaloid, zamamidine D (1), was isolated from an Okinawan Amphimedon sp. marine sponge. The structure of zamamidine D (1) including the relative configuration was elucidated on the basis of spectroscopic data. Zamamidine D (1) is the first manzamine alkaloid possessing a 2,2'-methylenebistryptamine unit as the aromatic moiety instead of a beta-carboline unit. Zamamidine D (1) showed antimicrobial activity against several bacteria and fungi.

DOI： 10.1021/acs.jnatprod.6b01110

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記述言語：英語   掲載種別：研究論文（学術雑誌）   出版者・発行元：PERGAMON-ELSEVIER SCIENCE LTD  

A new cyclic heptapeptide, stylissamide I (1), was isolated from an Okinawan marine sponge Stylissa sp. The structure of stylissamide I (1) was elucidated to be cydo-(L-Tyr(1)-L-Tyr(2)-L-Tyr(3)-L-Pro(1)-L-Pro(2)-L-Val-L-Pro(3)) by extensive spectral analyses and Marfey's method. Stylissamide I (1) showed antifungal activity against Aspergillus niger.

DOI： 10.3987/COM-16-S(S)45

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記述言語：英語   掲載種別：研究論文（学術雑誌）   出版者・発行元：PHARMACEUTICAL SOC JAPAN  

New bisindole alkaloids, hyrtinadines C (1) and D (2), have been isolated from an Okinawan marine sponge Hyrtios sp. The structures of hyrtinadines C (1) and D (2) were elucidated based on analyses of the spectral data. Hyrtinadines C (1) and D (2) were the relatively rare alkaloids possessing a 3,4-fused azepinoindole skeleton. Hyrtinadines C (1) and D (2) showed antimicrobial activity.

DOI： 10.1248/cpb.c16-00201

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記述言語：英語   掲載種別：研究論文（学術雑誌）   出版者・発行元：PHARMACEUTICAL SOC JAPAN  

The biogenetic origins of amphidinin A (1) and amphidinolide P (2) were investigated by feeding experiments with C-13-labeled acetates. C-13-NMR data of C-13-enriched samples revealed that the all carbons of 1 and 2 were derived from acetates. The polyketide chain of 1 was formed from one triketide chain, two diketide chains, and three unusual isolated C-1 units derived from C-2 of cleaved acetates, while the polyketide chain of 2 was formed from one pentaketide chain, two acetate units, and three unusual isolated C-1 units derived from C-2 of cleaved acetates. The all branched C-1 units of 1 and 2 were derived from C-2 of cleaved acetates.

DOI： 10.1248/cpb.c16-00202

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記述言語：英語   掲載種別：研究論文（学術雑誌）   出版者・発行元：WILEY-V C H VERLAG GMBH  

Amphidinolide N, the structure of which has been recently revised, is a 26-membered macrolide featuring allyl epoxide and tetrahydropyran moieties with 13 chiral centers. Due to its challenging structure and extraordinary potent cytotoxicity, amphidinolide N is a highly attractive target of total synthesis. During our total synthesis studies of the 7,10-epimer of the proposed structure of amphidinolide N, we have synthesized the C1-C13 subunit enantio- and diastereoselectively. Key reactions include an l-proline catalyzed enantioselective intramolecular aldol reaction, Evans aldol reaction, Sharpless asymmetric epoxidation and Tamao-Fleming oxidation. To aid late-stage manipulations, we also developed the 4-(N-benzyloxycarbonyl-N-methylamino)butyryl group as a novel ester protective group for the C9 alcohol.

DOI： 10.1002/chem.201504674

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記述言語：英語   掲載種別：研究論文（学術雑誌）   出版者・発行元：WILEY-V C H VERLAG GMBH  

The total synthesis of 7,10-epimer of the proposed structure of amphidinolideN was accomplished. The requisite chiral C17-C29 subunit was assembled stereoselectively via Keck allylation, Shi epoxidation, diastereoselective 1,3-reduction, and a later oxidative synthesis of the THF framework. The C1-C13 and C17-C29 subunits were successfully coupled using a Enders RAMP linchpin as the C14-C16 three carbon unit, thereby controlling the chirality at C14 and C16. The labile allyl epoxy moiety was successfully constructed by Grieco-Nishizawa olefination at a final stage of the synthesis.

DOI： 10.1002/chem.201504675

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記述言語：英語   掲載種別：研究論文（学術雑誌）   出版者・発行元：TAYLOR & FRANCIS LTD  

Speradine A is a derivative of cyclopiazonic acid (CPA) found in culture of an Aspergillus tamarii isolate. Heterologous expression of a predicted methyltransferase gene, cpaM, in the cpa biosynthesis gene cluster of A. tamarii resulted in the speradine A production in a 2-oxoCPA producing A. oryzae strain, indicating cpaM is involved in the speradine A biosynthesis.

DOI： 10.1080/09168451.2015.1065167

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記述言語：英語   掲載種別：研究論文（学術雑誌）   出版者・発行元：PERGAMON-ELSEVIER SCIENCE LTD  

Two new bromotyrosine alkaloids, tyrokeradines G (1) and H (2), have been isolated from an Okinawan marine sponge of the order Verongida. The structures of 1 and 2 were elucidated on the basis of spectroscopic data. Tyrokeradine G (1) is the first bromotyrosine alkaloid possessing a beta-alanine unit, while tyrokeradine H (2) is a rare bromotyrosine alkaloid possessing a N-substituted pyridinium ring. Tyrokeradines G (1) and H (2) showed antifungal activity. (C) 2015 Elsevier Ltd. All rights reserved.

DOI： 10.1016/j.bmcl.2015.09.061

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記述言語：英語   掲載種別：研究論文（学術雑誌）   出版者・発行元：PERGAMON-ELSEVIER SCIENCE LTD  

A new linear polyketide, amphidinin G (1), has been isolated from a symbiotic marine dinoflagellate Amphidinium sp. The planar structure of 1 was established mainly based on the 2D NMR data and the stereochemistry was elucidated by the combination off-value analysis, modified Mosher's method, and NMR chemical shift comparison with synthetic analogues. Amphidinin G (1) was expected to be a biosynthetic precursor of amphidinin A (2), a known linear dinoflagellate polyketide. Amphidinin G (1) showed antifungal activity against Trichophyton mentagrophytes. (C) 2015 Elsevier Ltd. All rights reserved.

DOI： 10.1016/j.tetlet.2015.01.058

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記述言語：英語   掲載種別：研究論文（学術雑誌）   出版者・発行元：PHARMACEUTICAL SOC JAPAN  

Iejimalides (IEJLs) A-D are 24-membered macrolides isolated from a tunicate Eudistoma cf. rigida, and exhibit potent cytotoxicity in vitro and antitumor activity in vivo. We previously reported that the molecular target of IEJL-A and -B was the vacuolar-type H+-ATPases (V-ATPases). However IEJL-C and -D, which are sulfonylated IEJL-A and -B, respectively, show more potent antitumor activity, and their molecular targets remain to be discovered. Here, we report that IEJL-C is also a potent V-ATPase inhibitor by binding in a site similar to the bafilomycin-binding site. Two-hour treatment with IEJL-C resulted in the complete disappearance of acidic organelles in HeLa cells. Interestingly, after 24-h treatment, small actin aggregates were observed instead of actin fibers. The same actin reorganization was also observed in cells treated with another V-ATPase inhibitor, bafilomycin A(1). Because IEJLs did not inhibit actin polymerization in vitro, these results suggest that the primary target of IEJL-C, as well as IEJL-A and -B, is V-ATPase, and actin reorganizations are probably caused by the disruption of pH homeostasis via V-ATPase inhibition.

DOI： 10.1248/bpb.b14-00548

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記述言語：英語   掲載種別：研究論文（学術雑誌）   出版者・発行元：AMER CHEMICAL SOC  

Four new polyketides, amphidinins CF (14), have been isolated from the culture broth of symbiotic dinoflagellate Amphidinium sp. The analysis of their spectral data revealed that amphidinins CF (14) were 4,5-seco-analogues of amphidinolide Q (5). The absolute configurations of the new compounds were elucidated by the combination of J-based configuration analysis, modified Moshers method, and chemical derivatization. Amphidinins D (2) and F (4) are the first glycosides related to amphidinolides. Amphidinins CF (14) showed antimicrobial activity against bacteria and/or fungi.

DOI： 10.1021/ol502685z

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記述言語：英語   掲載種別：研究論文（学術雑誌）   出版者・発行元：AMER CHEMICAL SOC  

The absolute configurations at six stereogenic centers in amphidinin A (1), a cytotoxic linear polyketide isolated from a symbiotic marine dinoflagellate, Amphidinium sp., were elucidated to be 2R, 4R, 6S, 9R 11R, and 12S by the combination of J-based configuration analysis, modified Mosher's method, and density-functional theory calculations.

DOI： 10.1021/np5003065

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記述言語：英語   掲載種別：研究論文（学術雑誌）   出版者・発行元：PHARMACEUTICAL SOC JAPAN  

New dimeric bromopyrrole-imidazole alkaloids, nagelamide I (1) and 2,2'-didebromonagelamide B (2), have been isolated from an Okinawan marine sponge Agelas species. The structures of 1 and 2 were elucidated based on analyses of the spectral data. Nagelamide I (1) was the first symmetric dimeric bromopyrrole-imidazole alkaloid consisting of two subunits connected with a single bond.

DOI： 10.1248/cpb.c13-00821

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記述言語：英語   掲載種別：研究論文（学術雑誌）   出版者・発行元：PHARMACEUTICAL SOC JAPAN  

New meroterpenoids, nakijiquinone S (1) and nakijinol C (2), have been isolated from an Okinawan marine sponge of the family Spongiidae. The gross structures and relative stereochemistries of 1 and 2 were elucidated on the basis of their spectral data. Nakijiquinone S (1) and nakijinol C (2) were new meroterpenoids consisting of a clerodane-type decalin ring connected to a 2-butoxy-5-hydroxy-benzoquinone unit or methyl 2,3,4-trihydroxybenzoate unit through a methylene, respectively. Nakijiquinone S (1) and nakijinol C (2) showed antimicrobial activities against several bacteria and fungi.

DOI： 10.1248/cpb.c13-00810

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記述言語：英語   掲載種別：研究論文（学術雑誌）   出版者・発行元：ROYAL SOC CHEMISTRY  

Two new acetylenic fatty acid derivatives possessing a taurine amide residue, taurospongins B (1) and C (2), have been isolated from an Okinawan marine sponge of the family Spongiidae. The gross structures of 1 and 2 were elucidated on the basis of their spectral data, especially 2D NMR and FABMS/MS data. The absolute configurations for 1 and 2 were established by chemical means. Taurospongin C (2) showed inhibitory activity against Cryptococcus neoformans.

DOI： 10.1039/c3ra47796g

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記述言語：英語   掲載種別：研究論文（学術雑誌）  

Two new alkaloids, hyrtimomines D (1) and E (2), were isolated from an Okinawan marine sponge Hyrtios sp. The structures of 1 and 2 were elucidated on the basis of spectroscopic analysis. Hyrtimomines D (1) and E (2) are structurally unique bisindole alkaloids possessing the canthin-6-one skeleton with a hydroxyindole and an imidazolium units. Hyrtimomines D (1) and E (2) exhibited antimicrobial activity. © 2013 Elsevier Ltd. All rights reserved.

DOI： 10.1016/j.tetlet.2013.05.073

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記述言語：英語   掲載種別：研究論文（学術雑誌）  

DOI： 10.1038/ja.2012.117

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記述言語：英語   掲載種別：研究論文（学術雑誌）   出版者・発行元：PERGAMON-ELSEVIER SCIENCE LTD  

Theonezolides A-C (1-3) are cytotoxic 37-membered macrolides with a long side chain isolated from an Okinawan marine sponge Theonella sp. The relative stereochemistry of 1-3 was investigated by combination of NMR analysis including application of a JBCA method, a Universal NMR database, and a C-13-acetonide method. Furthermore, the absolute configurations at 14 chiral centers in 1-3 were found to be 19S, 22R, 24S, 28S, 44S, 45S, 47R, 49S, 53R, 55S, 57S, 59S, 60S, and 63S by application of a modified Mosher's method. (C) 2012 Elsevier Ltd. All rights reserved.

DOI： 10.1016/j.tetlet.2012.11.120

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記述言語：英語   掲載種別：研究論文（学術雑誌）   出版者・発行元：AMER CHEMICAL SOC  

A manzamine related alkaloid, zamamiphidin A (1), consisting of a new heptacyclic ring system has been isolated from an Okinawan marine sponge Amphimedon sp. The structure of 1 including the relative stereochemistry was elucidated on the basis of the spectroscopic data. Compound 1 showed antibacterial activity against Staphylococcus aureus (MIC, 32 mu g/mL).

DOI： 10.1021/ol3034274

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記述言語：英語   掲載種別：研究論文（学術雑誌）   出版者・発行元：PERGAMON-ELSEVIER SCIENCE LTD  

Three new bis-3-alkylpyridine alkaloids, pyrinodemins G-I (1-3), were isolated from an Okinawan marine sponge Amphimedon sp. and the structures of 1-3 were elucidated on the basis of spectroscopic data. Pyrinodemins G-I (1-3) were novel bis-3-alkylpyridine alkaloids possessing an N-methoxy amide moiety, an alpha,beta-unsaturated 3,5-disubstituted gamma-lactone moiety, and a 2,3-di-substituted acrolein at a junction of two 3-alkylpyridines, respectively. Pyrinodemins G (1) and H (2) showed cytotoxicity against P388 murine leukemia cells. (C) 2012 Elsevier Ltd. All rights reserved.

DOI： 10.1016/j.tet.2012.10.062

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記述言語：英語   掲載種別：研究論文（学術雑誌）  

Metachromins are a series of sesquiterpenoid quinones isolated from Okinawan marine sponges. Inhibitory effects of metachromins L-Q (1-6), sesquiterpenoid quinones with an amino acid residue, and their related analogs (7-18) prepared from metachromins A (19) and C (20) against receptor tyrosine kinases EGFR and HER2 were investigated. Two analogs 11 and 12 showed relatively stronger inhibitory activity against EGFR, while metachromins L-Q (1-6) and seven analogs (8, 10, 11, and 15-18) showed inhibitory activities against HER2.

DOI： 10.1016/j.bmcl.2012.11.001

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記述言語：英語   掲載種別：研究論文（学術雑誌）   出版者・発行元：PERGAMON-ELSEVIER SCIENCE LTD  

Three new polyketides, manzamenones L-N (1-3), have been isolated from an Okinawan marine sponge of the genus Plakortis. The structures of 1-3 were elucidated on the basis of spectroscopic data. Manzamenones L-N (1-3) were new dimeric fatty-acid derivatives consisting of a tetrahydroindenone with three carboxy groups and two hexadecanyl chains. Manzamenones M (2) and N (3) showed antimicrobial activity against several bacteria and fungi. (c) 2012 Elsevier Ltd. All rights reserved.

DOI： 10.1016/j.bmcl.2012.10.109

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記述言語：英語   掲載種別：研究論文（学術雑誌）   出版者・発行元：PHARMACEUTICAL SOC JAPAN  

Four new bromotyrosine alkaloids, tyrokeradines C-F (1-4), have been isolated from Okinawan marine sponges of the order Verongidae. The structures of 1-4 were elucidated on the basis of spectroscopic data. Tyrokeradines C (1) and D (2) are new bromotyrosine alkaloids possesing an imidazole ring, while tyrokeradines E (3) and F (4) are new bromotyrosine alkaloids possesing a cyano group.

DOI： 10.1248/cpb.c12-00785

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記述言語：英語   掲載種別：研究論文（学術雑誌）   出版者・発行元：PERGAMON-ELSEVIER SCIENCE LTD  

New diterpene alkaloids, agelasines O-U (1-7), have been isolated from an Okinawan marine sponge Agelas sp. The gloss structures and relative stereochemistries of 1-7 were elucidated from the spectroscopic data. Agelasines O-R (1-4) were the third examples of diterpene alkaloid with a 9-N-methyladenine and a pyrrole units. Agelasine O (1) has a halimane skeleton, while agelasines P-R (2-4) have a clerodane skeleton. Agelasines S-U (5-7) were new diterpene alkaloids with a 9-N-methyladenine unit consisting of a halimane skeleton, a labdane skeleton, and a clerodane skeleton, respectively. Agelasines O-R (1-4) and T (6) showed antimicrobial activities against several bacteria and fungi. (c) 2012 Elsevier Ltd. All rights reserved.

DOI： 10.1016/j.tet.2012.09.040

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記述言語：英語   掲載種別：研究論文（学術雑誌）   出版者・発行元：PERGAMON-ELSEVIER SCIENCE LTD  

The structures of seven new secondary metabolites isolated from an Okinawan marine sponge Suberites sp., nakijinamines A (1), B (2), and F-I (3-6) and 6-bromoconicamin (7), have been elucidated on the basis of spectroscopic analysis, chemical conversion, and conformational analysis. These analyses disclosed that 1-6 were heteroaromatic alkaloids having the hybrid structures of an aaptamine-type alkaloid and an indole alkaloid, while 7 was a bromoindole alkaloid. Nakijinamine I (6) is the first example of an aaptamine-type alkaloid possessing a 1,4-dioxane ring. Antimicrobial activities of 1-7 were evaluated. (C) 2012 Elsevier Ltd. All rights reserved.

DOI： 10.1016/j.tet.2012.08.018

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記述言語：英語   掲載種別：研究論文（学術雑誌）   出版者・発行元：AMER CHEMICAL SOC  

Two new structurally unique dimeric sesquiterpenoids, halichonadins K (1) and L (2), were isolated from an Okinawan marine sponge Halichondria sp. The structures of 1 and 2 were elucidated on the basis of spectroscopic analysis including a single crystal X-ray diffraction analysis and chemical conversion. Halichonadins K (1) and L (2) are homodimers of the eudesmane sesquiterpene linked with a piperidine ring through amide bonds. Halichonadin K (1) showed moderate cytotoxicity against KB cells.

DOI： 10.1021/ol3014705

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記述言語：英語   掲載種別：研究論文（学術雑誌）   出版者・発行元：14  

DOI： 10.1016/j.bmcl.2011.05.072

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記述言語：英語   掲載種別：研究論文（学術雑誌）   出版者・発行元：AMER CHEMICAL SOC  

Three new heteroaromatic alkaloids, nakijinamines C-E (1-3), which are a hybrid of the aaptamine-type and bromoindole alkaloids possessing a taurine- or histidine-derived residue, have been isolated from an Okinawan marine sponge Suberites species. The structures of 1-3 were elucidated on the basis of spectroscopic data and chemical conversions. Nakijinamines C (1) and E (3) are the first natural products possessing a 1H-oxazolo[4',5':4,5]benzo[1,2,3-de][1,6]naphthyridine ring system.

DOI： 10.1021/ol2008473

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記述言語：英語   掲載種別：研究論文（学術雑誌）   出版者・発行元：4  

Two novel alkaloids with a furo[2,3-b]pyrazin-2(1H)-one moiety and a guanidino group, hyrtioseragamines A (1) and B (2), have been isolated from an Okinawan marine sponge Hyrtios species. The structures of 1 and 2 were elucidated on the basis of spectroscopic data and chemical conversions. Compounds 1 and 2 are the first natural products possessing a furo[2,3-b]pyrazine-related moiety.

DOI： 10.1021/ol102867x

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記述言語：英語   掲載種別：研究論文（学術雑誌）   出版者・発行元：PERGAMON-ELSEVIER SCIENCE LTD  

Three new Lycopodium alkaloids, lyconadins D (1) and E (2), and complanadine E (3), were isolated from the club moss Lycopodium complanatum. Lyconadin D (1) was the first example of fastigiatine-type alkaloid isolated from Lycopodium complanatum. The structures and relative stereochemistry of 1-3 were elucidated on the basis of spectroscopic data. Complanadine E (3) enhanced mRNA expression for NGF. (C) 2010 Elsevier Ltd. All rights reserved.

DOI： 10.1016/j.bmc.2010.12.025

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記述言語：英語   掲載種別：研究論文（学術雑誌）   出版者・発行元：PERGAMON-ELSEVIER SCIENCE LTD  

New Lycopodium alkaloids, lyconadins C (1) and F (2), were isolated from the club moss Lycopodium complanatum. Lyconadin C (1) is a new C(16)N(2)-type Lycopodium alkaloid possessing unique fused-tetracyclic ring system consisting of a cycloheptene ring fused to a decahydroquinoline and pyridone rings. Lyconadin F (2) possesses a primary amide moiety in its molecular, which is the first example of Lycopodium alkaloids. Biogenetically, lyconadins C (1) and F (2) might be related to lyconadins A (4) and B (5). The structures and relative stereochemistry of 1 and 2 were elucidated on the basis of spectroscopic data. The absolute stereochemistry of 2 was elucidated by chemical correlations with lyconadin B (5) through hemiaminal form of lyconadin F (3). (C) 2010 Elsevier Ltd. All rights reserved.

DOI： 10.1016/j.tetlet.2010.11.024

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記述言語：英語   掲載種別：研究論文（学術雑誌）   出版者・発行元：PERGAMON-ELSEVIER SCIENCE LTD  

Two new 3-alkylpyridine alkaloids, pyrinodemins E(1) and F(2), were isolated from an Okinawan marine sponge Amphimedon sp. and the structures of 1 and 2 were elucidated on the basis of spectroscopic data. Pyrinodemins E(1) and F(2) were novel 3-alkylpyridine alkaloids possessing a 4-(methoxyamino)piperidinone moiety and an indol-3-glyoxylamide moiety, respectively. Pyrinodemin E (1) showed cytotoxicity against P388 and L1210 murine leukemia cells. (C) 2010 Elsevier Ltd. All rights reserved.

DOI： 10.1016/j.bmcl.2010.11.020

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記述言語：英語   掲載種別：研究論文（学術雑誌）   出版者・発行元：PERGAMON-ELSEVIER SCIENCE LTD  

A new cytotoxic 25-membered macrolide, amphidinolide C3 (1), has been isolated from marine dinoflagellate Amphidinium sp. (Y-56 strain), and the structure of 1 was elucidated on the basis of spectroscopic data and chemical means.

DOI： 10.3987/COM-10-S(E)3

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記述言語：英語   掲載種別：研究論文（学術雑誌）   出版者・発行元：PERGAMON-ELSEVIER SCIENCE LTD  

A new polyketide, untenolide A (1), has been isolated from an Okinawan marine sponge Plakortis species, and the structure was elucidated from spectroscopic data and X-ray analysis. Untenolide A (1) is a new polyketide possessing a fused-pentacyclic skeleton with two hexadecanyl chains. (C) 2010 Elsevier Ltd. All rights reserved.

DOI： 10.1016/j.tetlet.2010.05.085

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記述言語：英語   掲載種別：研究論文（学術雑誌）   出版者・発行元：PERGAMON-ELSEVIER SCIENCE LTD  

Three new bromotyrosine alkaloids, ceratinadins A-C (1-3), were isolated from an Okinawan marine sponge Pseudoceratina sp. and the structures of 1-3 were elucidated on the basis of spectroscopic data. Ceratinadin A (1) was a novel bromotyrosine alkaloid possessing an N-imidazolyl-quinolinone moiety. Ceratinadins A (1) and B (2) showed antifungal activity. (C) 2010 Elsevier Ltd. All rights reserved.

DOI： 10.1016/j.bmcl.2010.06.015

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記述言語：英語   掲載種別：研究論文（学術雑誌）   出版者・発行元：PERGAMON-ELSEVIER SCIENCE LTD  

A new beta-carboline alkaloid, eudistomidin G (1), has been isolated from the Okinawan marine tunicate Eudistoma glaucus, and the structure was elucidated from spectroscopic data. Furthermore, the structure of eudistomidin B (2), which has been isolated from the same tunicate, was revised from 2a to 2b by detailed analyses of spectroscopic data. Asymmetric synthesis of the revised structure (2b) of eudistomidin B (2) and its (1S, 10S)-diastereomer (2c) has been accomplished with the Noyori catalytic asymmetric hydrogen-transfer reaction. The absolute configuration of eudistomidin B (2) was confirmed to be 2b possessing (1R, 10S)-configuration, from comparison of the (1)H NMR data, CD spectra, [a] D values, and HPLC analysis of 2b, 2c, and natural eudistomidin B. (C) 2010 Elsevier Ltd. All rights reserved.

DOI： 10.1016/j.bmcl.2010.05.071

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記述言語：英語   掲載種別：研究論文（学術雑誌）   出版者・発行元：AMER CHEMICAL SOC  

Nine new sesquiterpenoid quinones, nakijiquinones J-R (1 -9), have been isolated from three collections of Okinawan marine sponges of the family Spongiidae, and the structures and configurations were elucidated from the spectroscopic data and chemical correlations. Nakijiquinones J-L (1-3), M and N (4 and 5, respectively), 0 (6), 11 and Q (7 and 8, respectively), and R (9) are new sesquiterpenoid quinones possessing (S)-2-methylbutylamine, isopentylamine, isobutylamine, phenethylamine, and taurine residues, respectively, attached to each quinone ring.

DOI： 10.1021/np900470e

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記述言語：英語   掲載種別：研究論文（学術雑誌）   出版者・発行元：PERGAMON-ELSEVIER SCIENCE LTD  

Three new N-methyl pyridinium alkaloids, platisidines A-C (1-3), were isolated from an Okinawan marine sponge of the genus Plakortis, and the structures were elucidated from spectroscopic data. The structures of platisidines A-C (1-3) were elucidated to be N-methyl nicotinic acid derivatives with a n-hexadecanoyl chain. Platisidines A-C (1-3) showed inhibitory activity against acetylcholinesterase.

DOI： 10.3987/COM-09-S(S)131

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掲載種別：論文集(書籍)内論文  

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記述言語：英語   掲載種別：研究論文（学術雑誌）   出版者・発行元：PERGAMON-ELSEVIER SCIENCE LTD  

Four new prenylated xanthones, biyouxanthones A - D (1 - 4), were isolated from roots of Hypericum chinense. The gross structures of 1 - 4 were elucidated from spectroscopic data, and 2 was assigned as a racemate by chiral HPLC analysis. Biyouxanthones A (1) and B (2) exhibited anti-viral activity against hepatitis C virus (HCV).

DOI： 10.3987/COM-09-S(S)28

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記述言語：英語   掲載種別：研究論文（学術雑誌）   出版者・発行元：PERGAMON-ELSEVIER SCIENCE LTD  

A new dimeric bromopyrrole alkaloid possessing a benzocyclobutane ring, benzosceptrin C (1), has been isolated from an Okinawan marine sponge of the genus Agelas (SS-956), and the structure and relative stereochemistry were elucidated from spectroscopic data. Benzosceptrin C (1) showed antimicrobial activity. (C) 2009 Elsevier Ltd. All rights reserved.

DOI： 10.1016/j.tetlet.2009.10.017

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記述言語：英語   掲載種別：研究論文（学術雑誌）   出版者・発行元：PERGAMON-ELSEVIER SCIENCE LTD  

A novel Lycopodium alkaloid, lycopladine H (1), with a fused-tetracyclic ring system consisting of an azocane ring connected to a [2.2.2]-bicyclooctane ring and a 3-piperidone ring, was isolated from the club moss lycopodium complanatum. The structure and relative stereochemistry of I were elucidated on the basis of spectroscopic data (C) 2009 Elsevier Ltd All rights reserved

DOI： 10.1016/j.tetlet.2009.09.035

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記述言語：英語   掲載種別：研究論文（学術雑誌）   出版者・発行元：PHARMACEUTICAL SOC JAPAN  

Four new benzophenone-O-rhamnosides, petiolins F-I (1-4), were isolated from aerial parts of Hypericum pseudopetiolatum var. kiusianum, and the structures were elucidated by spectroscopic data and chemical means.

DOI： 10.1248/cpb.57.1171

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記述言語：英語   掲載種別：研究論文（学術雑誌）   出版者・発行元：PHARMACEUTICAL SOC JAPAN  

Four new benzophenone-O-rhamnosides, petiolins F-I (1-4), were isolated from aerial parts of Hypericum pseudopetiolatum var. kiusianum, and the structures were elucidated by spectroscopic data and chemical means.

DOI： 10.1248/cpb.57.1171

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記述言語：英語   掲載種別：研究論文（学術雑誌）  

DOI： 10.1016/j.tetlet.2009.06.021

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記述言語：英語   掲載種別：研究論文（学術雑誌）   出版者・発行元：PHARMACEUTICAL SOC JAPAN  

Three new Lycopodium alkaloids, lannotinidines H-J (1-3), were isolated from the club moss Lycopodium annotinum. The structures and relative stereochemistry of 1-3 were elucidated on the basis of spectroscopic data and the absolute stereochemistry of 2 was assigned by chemical correlation. Lannotinidine H (1) is the first Lycopodium alkaloid possessing a lycopodane skeleton with an additional C-3 unit.

DOI： 10.1248/cpb.57.877

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記述言語：英語   掲載種別：研究論文（学術雑誌）   出版者・発行元：PHARMACEUTICAL SOC JAPAN  

Three new Lycopodium alkaloids, lannotinidines H-J (1-3), were isolated from the club moss Lycopodium annotinum. The structures and relative stereochemistry of 1-3 were elucidated on the basis of spectroscopic data and the absolute stereochemistry of 2 was assigned by chemical correlation. Lannotinidine H (1) is the first Lycopodium alkaloid possessing a lycopodane skeleton with an additional C-3 unit.

DOI： 10.1248/cpb.57.877

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その他リンク： http://orcid.org/0000-0002-3553-5844

記述言語：英語   掲載種別：研究論文（学術雑誌）   出版者・発行元：PERGAMON-ELSEVIER SCIENCE LTD  

Two new Lycopodium alkaloids, lycopladines F (1) and G (2), have been isolated from the club moss Lycopodium complanatum, and the structures and relative stereochemistries of I and 2 were elucidated on the basis of spectroscopic data. Lycopladine F (1) is a rare C16N2-type Lycopodium alkaloid possessing an amino acid residue (C4N) (C) 2009 Elsevier Ltd. All rights reserved.

DOI： 10.1016/j.tetlet.2009.04.139

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記述言語：英語   掲載種別：研究論文（学術雑誌）   出版者・発行元：PERGAMON-ELSEVIER SCIENCE LTD  

A new piperidine alkaloid plakoridine C (1) has been isolated from an Okinawan marine sponge Plakortis species, and the structure was elucidated from spectroscopic data. Plakoridine C (1) is a new alkaloid possessing a piperidine ring connected to a beta-keto-gamma-lactone through a double bond. (C) 2009 Elsevier Ltd. All rights reserved.

DOI： 10.1016/j.tetlet.2009.01.135

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記述言語：英語   掲載種別：研究論文（学術雑誌）   出版者・発行元：PERGAMON-ELSEVIER SCIENCE LTD  

Two new Lycopodium alkaloids, serratezomines D (1) and E (2), were isolated from the club moss Lycopodium serratum var. serratum. Serratezomine D (1) is a new lucidine-type alkaloid, while serratezomine E (2) is a new phlegmarane-type alkaloid. The structures and relative stereochemistry of 1 and 2 were elucidated on the basis of spectroscopic data. Serratezomine D (1) exhibited an inhibitory activity against acetylcholinesterase. (C) 2009 Elsevier Ltd. All rights reserved.

DOI： 10.1016/j.bmcl.2009.04.146

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記述言語：英語   出版者・発行元：ROYAL SOC CHEMISTRY  

About two hundred Daphniphyllum alkaloids have so far been isolated from thirteen species of the genus Daphniphyllum. This comprehensive review summarizes all the research into the isolation and structure elucidation of these alkaloids reported since investigations began in 1966. The structures of the Daphniphyllum alkaloids are classified based on six Daphniphyllum alkaloids (daphniphylline, secodaphniphylline, yuzurimine, daphnilactone A, daphnilactone B and yuzurine); there are also a number of newly found skeletons. The biosynthetic pathways, total syntheses, and bioactivities of the Daphniphyllum alkaloids are also described.

DOI： 10.1039/b813006j

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記述言語：英語   掲載種別：研究論文（学術雑誌）   出版者・発行元：PHARMACEUTICAL SOC JAPAN  

Three new Daphniphyllum alkaloids, daphnezomines T-V (1-3), were isolated from the leaves and branches of Daphniphyllum humile (Daphniphyllaceae). The structures and relative stereochemistry of 1-3 were elucidated on the basis of spectroscopic data. Daphnezomine T (1) is the first alkaloid without a branched C-1 unit at C-5 among all Daphiniphyllum alkaloids reported so far.

DOI： 10.1248/cpb.57.504

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その他リンク： http://orcid.org/0000-0002-3553-5844

記述言語：英語   掲載種別：研究論文（学術雑誌）   出版者・発行元：PHARMACEUTICAL SOC JAPAN  

Three new Daphniphyllum alkaloids, daphnezomines T-V (1-3), were isolated from the leaves and branches of Daphniphyllum humile (Daphniphyllaceae). The structures and relative stereochemistry of 1-3 were elucidated on the basis of spectroscopic data. Daphnezomine T (1) is the first alkaloid without a branched C-1 unit at C-5 among all Daphiniphyllum alkaloids reported so far.

DOI： 10.1248/cpb.57.504

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記述言語：英語   掲載種別：研究論文（学術雑誌）   出版者・発行元：PERGAMON-ELSEVIER SCIENCE LTD  

Asymmetric synthesis of amphidinolactone A, a cytotoxic macrolide from the Cultured dinoflagellate Amphidinium sp., has been accomplished. Absolute configuration of amphidinolactone A was concluded to be 1 from comparison of the NMR data and vertical bar x vertical bar(D) values of synthetic and natural amphidinolactone A. (C) 2009 Elsevier Ltd. All rights reserved.

DOI： 10.1016/j.tetlet.2009.01.065

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記述言語：英語   掲載種別：研究論文（学術雑誌）   出版者・発行元：WILEY-V C H VERLAG GMBH  

A sequence of ring-closing alkyne metathesis followed by an intermolecular enyne metathesis of the resulting cycloalkyne with ethene was used to forge the macrocyclic skeleton and to set the vicinal exo-methylene branches characteristic for the cytotoxic marine natural product amphidinolide V (1). Comparison of the synthetic material with all authentic sample of this extremely scarce metabolite isolated from a dinoflagellate of the Amphidinium sp. eliminated any, doubts about its structure and allowed the absolute configuration of amphidinolide V to be determined as 8R,9S,10S,13R. Moreover, the flexibility inherent to the underlying Synthesis blueprint also opened access to a comprehensive set of diastereomers of I as well as to synthetic analogues differing from the natural lead in the lipophilic chains appended to the macrocyclic core. This set of designed analogues gave first insights into structure-activity relationships, which revealed that the stereo-structure Of the macrolactone is a highly critical parameter, whereas the examined alterations of the side chain did not diminish the cytotoxicity, of the compounds to any notable extent.

DOI： 10.1002/chem.200802068

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記述言語：英語   掲載種別：研究論文（学術雑誌）   出版者・発行元：PERGAMON-ELSEVIER SCIENCE LTD  

A new phloroglucinol derivative possessing citran skeleton, petiolin D (1), and a new chromone glucoside, petiolin E (2), were isolated from aerial parts of Hypericum pseudopetiolatum var. kiusianum. The structures of I and 2 were elucidated by spectroscopic data, and a single-crystal X-ray diffraction analysis of 1 revealed that 1 was a racemic mixture.

DOI： 10.3987/COM-08-S(D)64

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記述言語：英語   掲載種別：研究論文（学術雑誌）   出版者・発行元：AMER CHEMICAL SOC  

Two new dimeric bromopyrrole alkaloids, nagelamides Q (1) and R (2), have been isolated from Okinawan marine sponges of the genus Agelas (SS-1134 and SS-956, respectively), and the structures and stereochemistry were elucidated from spectroscopic data. Nagelamide Q (1) is a rare dimeric bromopyrrole alkaloid possessing a pyrrolidine ring, while nagelamide R (2) is the first bromopyrrole alkaloid having an oxazoline ring. Nagelamides Q (1) and R (2) showed antimicrobial activity.

DOI： 10.1021/ol900328c

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記述言語：英語   掲載種別：研究論文（学術雑誌）   出版者・発行元：PERGAMON-ELSEVIER SCIENCE LTD  

A new monoterpene indole alkaloid, naucleamide F (1), has been isolated from the bark and wood of Nauclea latifolia, and the structure and stereochemistry were elucidated on the basis of the spectral data. Naucleamide F (1) is a new monoterpene indole alkaloid consisting of a tetrahydro-beta-carboline ring fused to a pyridone ring, and a 1,3,5-trioxepane ring fused to a dihydropyran ring and a glucose unit.

DOI： 10.3987/COM-08-S(D)41

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記述言語：英語   掲載種別：研究論文（学術雑誌）   出版者・発行元：AMER CHEMICAL SOC  

Four new bromopyrrole alkaloids, nagelamides O (1) and P (2) and mukanadins E (3) and F (4), were isolated from three collections of Okinawan marine sponges of the genus Agelas. The structures and sterectchemistry of 1-4 were elucidated on the basis of their spectroscopic data.

DOI： 10.1021/np800645q

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記述言語：英語   掲載種別：研究論文（学術雑誌）   出版者・発行元：PERGAMON-ELSEVIER SCIENCE LTD  

Two new dimeric sesquiterpenoid quinones, nakijiquinones E (1) and F (2), have been isolated from an Okinawan marine sponge, and the structures and relative stereochemistry of 1 and 2 were elucidated on the basis of the spectral data. Nakijiquinones E (1) and F (2) were the first dimeric sesquiterpenoid quinones possessing a 3-aminobenzoate moiety. (C) 2008 Elsevier Ltd. All rights reserved.

DOI： 10.1016/j.bmc.2008.10.080

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記述言語：英語   掲載種別：研究論文（学術雑誌）   出版者・発行元：PERGAMON-ELSEVIER SCIENCE LTD  

New manzamine alkaloids, zamamidine C (1), 3,4-dihydro-6-hydroxy-10,11-epoxymanzamine A (2), and 3,4-dihydromanzamine J N-oxide (3). have been isolated from an Okinawan marine sponge Amphimedon species. The Structures and stereochemistries of 1-3 were elucidated from the spectroscopic data and chemical derivatization. Zamamidine C (1) is a new manzamine alkaloid possessing a second beta-carboline ring via an ethylene unit at N-2 of manzamine D, while 3,4-dihydro-6-hydroxy-10,11-epoxymanzamine A (2) is the first manzamine alkaloid possessing an epoxide ring at C-10 and C-11. Zamamidine C (1) showed significant antitrypanosomal activity against Trypanosoma brucei brucei, the parasite associated with sleeping sickness, and antimalarial activity against Plasmodium falciparum, the causative agent of malaria in vitro. (C) 2009 Elsevier Ltd. All rights reserved.

DOI： 10.1016/j.tet.2009.01.032

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記述言語：英語   掲載種別：研究論文（学術雑誌）   出版者・発行元：PERGAMON-ELSEVIER SCIENCE LTD  

Two new bromotyrosine alkaloids, tyrokeradines A (1) and B (2), with an imidazolyl-quinolinone moiety have been isolated from an Okinawan marine sponge of the order Verongida. The structures of 1 and 2 were elucidated on the basis of spectroscopic data. (C) 2009 Elsevier Ltd. All rights reserved.

DOI： 10.1016/j.bmcl.2009.01.056

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記述言語：英語   掲載種別：研究論文（学術雑誌）   出版者・発行元：AMER CHEMICAL SOC  

New manzamine alkaloids, zemamidines A (1) and B (2), have been isolated from an Okinawan marine sponge Amphimedon species. The structures and stereochemistry of 1 and 2 were elucidated from the spectroscopic data and conformational analysis. Zamamidines A (1) and B (2) are the first manzamine alkaloids possessing a second beta-carboline ring via an ethylene unit at N-2 of manzamine H and 1,2,3,4-tetrahydromanzamine B, respectively.

DOI： 10.1021/ol802251q

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記述言語：英語   掲載種別：研究論文（学術雑誌）   出版者・発行元：AMER CHEMICAL SOC  

Three new Daphniphyllum alkaloids, calyciphyllines N-P (1-3), were isolated from the leaves and stems of Daphniphyllum calycinum. The structures and relative stereochemistry of 1-3 were elucidated on the basis of spectroscopic data.

DOI： 10.1021/np800515s

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記述言語：英語   掲載種別：研究論文（学術雑誌）   出版者・発行元：PERGAMON-ELSEVIER SCIENCE LTD  

Two new bromopyrrole alkaloids, nagelamides M (1) and N (2), have been isolated from an Okinawan marine sponge Agelas species, and the structures and stereochemistry were elucidated from the spectroscopic data. Nagelamide M (1) is a novel bromopyrrole alkaloid possessing a 2-amino-octahydropyrrolo[2,3-d]imidazole ring with a taurine unit, while nagelamide N (2) is a new bromopyrrole alkaloid possessing a 2-amino-tetrahydroimidazole-4-one ring with a taurine unit and 3-(dibromopyrrole-2-carboxamido)propanoic acid moiety. Nagelamides M (1) and N (2) exhibited antimicrobial activity. (C) 2008 Elsevier Ltd. All rights reserved.

DOI： 10.1016/j.tet.2008.09.039

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記述言語：英語   掲載種別：研究論文（学術雑誌）   出版者・発行元：PERGAMON-ELSEVIER SCIENCE LTD  

A new pentacyclic hydroquinone sulfate with a 2,5-dihydro-2,5-furandiol ring, xestosaprol C (1), has been isolated from an Okinawan marine sponge Xestospongia sapra. The structure of I was elucidated by the spectroscopic data.

DOI： 10.3987/COM-08-S(N)122

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記述言語：英語   掲載種別：研究論文（学術雑誌）   出版者・発行元：AMER CHEMICAL SOC  

The absolute configurations at five chiral centers in amphidinolide Q (1), a cytotoxic 12-membered macrolide isolated from a marine dinoflagellate Amphidinium sp., were elucidated to be 4R, 7R, 9S, 11 R, and 13R on the basis of NMR analyses and a modified Mosher's method.

DOI： 10.1021/ol8013123

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記述言語：英語   掲載種別：研究論文（学術雑誌）   出版者・発行元：PERGAMON-ELSEVIER SCIENCE LTD  

Three new sesquiterpenoid quinones, nakijiquinones G-I (1-3), containing a different amino group derived from amino acids have been isolated from Okinawan marine sponges of the family Spongiidae, and the structures and relative stereochemistry of 1-3 were elucidated on the basis of the spectral data. Nakijiquinones G-I (1-3) showed modest cytotoxicity and inhibitory activity against HER2 kinase, while nakijiquinone H (2) exhibited antimicrobial activity. (C) 2008 Elsevier Ltd. All rights reserved.

DOI： 10.1016/j.bmc.2008.07.028

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記述言語：英語   掲載種別：研究論文（学術雑誌）   出版者・発行元：AMER CHEMICAL SOC  

Two new dimeric bromopyrrole alkaloids, nagelamides K (1) and L (2), have been isolated from Okinawan marine sponges Agelas species, and the structures and stereochemistry were elucidated from spectroscopic data. Nagelamide K (1) is a bromopyrrole alkaloid possessing a rare piperidinoiminoimidazolone ring with an aminoimidazole ring and a taurine unit, while nagelamide L (2) is a unique dimeric bromopyrrole alkaloid containing an ester linkage. Nagelamides K (1) and L (2) exhibited antimicrobial activity.

DOI： 10.1021/ol8003904

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記述言語：英語   掲載種別：研究論文（学術雑誌）   出版者・発行元：PERGAMON-ELSEVIER SCIENCE LTD  

Two new phloroglucinol derivatives possessing chromane skeleton, petiolins A ( 1) and B ( 2), and a new phloroglucinol derivative containing a dihydrofuran ring, petiolin C ( 3), were isolated from aerial parts of Hypericum pseudopetiolatum var. kiusianum. The gross structures of 1-3 were elucidated by spectroscopic data, and the relative stereochemistry of 3 was elucidated by NOESY data. Petiolins A-C (1-3) showed modest cytotoxicity, while petiolin C ( 3) exhibited antifungal activity. (C) 2008 Elsevier Ltd. All rights reserved.

DOI： 10.1016/j.bmc.2008.03.076

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記述言語：英語   掲載種別：研究論文（学術雑誌）  

DOI： 10.1016/j.tet.2008.01.111

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記述言語：英語   掲載種別：研究論文（学術雑誌）   出版者・発行元：PERGAMON-ELSEVIER SCIENCE LTD  

Six new Daphniphyllum alkaloids, calyciphyllines H-M (1-6), were isolated from the leaves and stems of Daphniphyllum calycinum (Daphniphyllaceac). The structures and relative stereochemistry of 1-6 were elucidated on the basis of spectroscopic data, and the absolute stereochemistry of 3 was assigned by PGME method. (C) 2007 Elsevier Ltd. All rights reserved.

DOI： 10.1016/j.tet.2007.11.087

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記述言語：英語   掲載種別：研究論文（学術雑誌）  

DOI： 10.3987/com-07-s(w)77

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記述言語：英語   掲載種別：研究論文（学術雑誌）   出版者・発行元：PERGAMON-ELSEVIER SCIENCE LTD  

A new C(16)N(1)-type alkaloid, lycopladine E (1), has been isolated from the club moss Lycopodium complanatum, and the structure and absolute stereochemistry were elucidated on the basis of spectroscopic data and chemical correlation.

DOI： 10.3987/com-07-s(w)76

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記述言語：英語   掲載種別：研究論文（学術雑誌）   出版者・発行元：AMER CHEMICAL SOC  

Extensive column chromatography of the ethanolic extract of the soft coral Cespitularia taeniata collected in Taiwan has resulted in the isolation of eight new nitrogen-containing verticillene diterpenes, designated cespitulactams D-K (1-8), together with three known diterpenes, cespitulactams A (9) and B (10) and cespitularin F. In addition, one new derivative, 6-O-acetyleespitulactam F (11), was prepared from compound 3. The structures of these compounds were elucidated on the basis of spectroscopic analyses, especially HRMS and 2D NMR experiments. The cytotoxicity against human oral epidermoid carcinoma (KB) and murine L1210 leukemia cell lines and antimicrobial activities of 1-8 and 11 were tested and evaluated. A biogenetic pathway for these novel diterpene alkaloids was also proposed.

DOI： 10.1021/np078011u

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記述言語：英語   掲載種別：研究論文（学術雑誌）   出版者・発行元：PHARMACEUTICAL SOC JAPAN  

Three new sesquiterpenoids, metachromins R-T (1-3), have been isolated from an Okinawan marine sponge Spongia sp. The structures and stereochemistry of 1-3 were elucidated on the basis of the spectroscopic data. Metachromins S (2) and T (3) showed modest cytotoxicity.

DOI： 10.1248/cpb.55.1731

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記述言語：英語   掲載種別：研究論文（学術雑誌）   出版者・発行元：PERGAMON-ELSEVIER SCIENCE LTD  

A new dimeric Lythraceac alkaloid with a cyclobutane ring, sarusubine A (1), has been isolated from the leaves of Lagerstroemia subcostata, and the structure and stereochemistry were elucidated by spectroscopic data. (C) 2007 Elsevier Ltd. All rights reserved.

DOI： 10.1016/j.tetlet.2007.08.059

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記述言語：英語   掲載種別：研究論文（学術雑誌）   出版者・発行元：PERGAMON-ELSEVIER SCIENCE LTD  

Six new sesquiterpenoid quinones with an amino acid residue, metachromins L-Q (1-6), have been isolated from an Okinawan marine sponge Spongia sp. The structures and stereochemistry of 1-6 were elucidated on the basis of the spectroscopic data and chemical correlations. Metachromins L (1) and M (2) showed modest cytotoxicity. (c) 2007 Elsevier Ltd. All rights reserved.

DOI： 10.1016/j.tet.2007.06.031

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記述言語：英語   掲載種別：研究論文（学術雑誌）   出版者・発行元：PERGAMON-ELSEVIER SCIENCE LTD  

Calyciphylline G (1), a novel Daphniphyllum alkaloid with an unprecedented fused-hexacyclic skeleton containing a 5-azatricyclo[6.2.1.0(1,5)]undecane ring, has been isolated from the stem of Daphniphyllum calycinum (Daphniphyllaceae), and the structure and relative stereochemistry were elucidated on the basis of spectroscopic data. (c) 2007 Elsevier Ltd. All rights reserved.

DOI： 10.1016/j.tetlet.2007.05.172

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記述言語：英語   掲載種別：研究論文（学術雑誌）  

DOI： 10.1016/j.tetlet.2007.05.121

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記述言語：英語   掲載種別：研究論文（学術雑誌）   出版者・発行元：AMER CHEMICAL SOC  

A novel dimeric bromopyrrole alkaloid, nagelamide J (1), with antimicrobial activity has been isolated from an Okinawan marine sponge Agelas species, and the structure and stereochemistry were elucidated from spectroscopic data. Nagelamide J (1) is the first bromopyrrole alkaloid possessing a cyclopentane ring fused to an amino imidazole ring.

DOI： 10.1021/ol0707867

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記述言語：英語   掲載種別：研究論文（学術雑誌）   出版者・発行元：JAPAN ANTIBIOTICS RESEARCH ASSOC  

A new 26-membered macrolide, amphidinolactone 13, has been isolated from a marine dinoflagellate Amphidinium sp., and the structure and relative stereochemistry were elucidated on the basis of spectroscopic data. Amphidinolactone B (1) showed modest cytotoxicity.

DOI： 10.1038/ja.2007.51

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記述言語：英語   掲載種別：研究論文（学術雑誌）   出版者・発行元：PERGAMON-ELSEVIER SCIENCE LTD  

Two new Daphniphyllum alkaloids, calyciphyllines E (1) and F (2), have been isolated from the leaves of Daphniphyllum calycinum (Daphniphyllaceae), and the structures and relative stereochemistry were elucidated on the basis of spectroscopic data. (C) 2007 Elsevier Ltd. All rights reserved.

DOI： 10.1016/j.tetlet.2007.03.156

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記述言語：英語   掲載種別：研究論文（学術雑誌）   出版者・発行元：PERGAMON-ELSEVIER SCIENCE LTD  

A new 13-membered macrolide, amphidinolactone A (1), has been isolated from a marine dinoflagellate Amphidinium sp., and the structure and relative stereochemistry were elucidated by spectroscopic data. Amphidinolactone A (1) is the first macrolide without a branched methyl or an exomethylene among all the macrolides isolated from the dinoflagellates so far.

DOI： 10.3987/com-06-s(k)49

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記述言語：英語   掲載種別：研究論文（学術雑誌）   出版者・発行元：AMER CHEMICAL SOC  

Calyciphylline D (1), a novel Daphniphyllum alkaloid with an unprecedented fused-pentacyclic skeleton containing a 8-azatricyclo[4.2.1.0.(4,8)]nonane ring system, has been isolated from the leaves of Daphniphyllum calycinum (Daphniphyllaceae), and the structure and relative stereochemistry were elucidated on the basis of spectroscopic data.

DOI： 10.1021/ol0631455

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記述言語：英語   出版者・発行元：AMER CHEMICAL SOC  

Marine microorganisms such as bacteria, cyanobacteria, dinoflagellates, and others have attracted many natural product chemists as the real producers of marine toxins such as fish and algal poisons as well as bioactive substances isolated from marine invertebrates such as sponges and tunicates. Among marine microorganisms, dinoflagellates have proved to be important sources of marine toxins and have been investigated worldwide by natural product chemists. We have continued investigations on chemically interesting and biologically significant secondary metabolites from Amphidinium spp., of a genus of symbiotic marine dinoflagellates separated from inside cells of Okinawan marine flatworms. This review covers the results described in our recent publications on a series of cytotoxic macrolides, designated amphidinolides, and long-chain polyketides isolated from Amphidinium spp. In this review, topics include the isolation, structure elucidation, synthesis, biosynthesis, and bioactivity of amphidinolides and long-chain polyketides.

DOI： 10.1021/np0605844

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記述言語：英語   掲載種別：研究論文（学術雑誌）   出版者・発行元：PERGAMON-ELSEVIER SCIENCE LTD  

Calyciphylline C (1), a novel Daphniphyllum alkaloid with unprecedented fused-hexacyclic ring system, has been isolated from the leaves of Daphniphyllum calycinum (Daphniphyllaceae), and the structure and relative stereochemistry were elucidated on the basis of spectroscopic data. (c) 2007 Elsevier Ltd. All rights reserved.

DOI： 10.1016/j.tetlet.2006.12.139

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記述言語：英語   掲載種別：研究論文（学術雑誌）   出版者・発行元：PERGAMON-ELSEVIER SCIENCE LTD  

Two new dimeric Lycopodium alkaloids, complanadines C (1) and D (2), have been isolated from the club moss Lycopodium complanatum, and the structures and relative stereochemistry of I and 2 were elucidated on the basis of the spectral data. Complanadine D (2) enhanced mRNA expression for NGF. (c) 2006 Elsevier Ltd. All rights reserved.

DOI： 10.1016/j.bmc.2006.09.043

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記述言語：英語   掲載種別：研究論文（学術雑誌）   出版者・発行元：PERGAMON-ELSEVIER SCIENCE LTD  

Six new cytotoxic bis-3-alkylpyridine alkaloids with an azoxy moiety, pyrinadines B-G (1-6), have been isolated from an Okinawan marine sponge Cribrochalma sp., and the structures were elucidated by spectroscopic data and chemical means. (c) 2006 Elsevier Ltd. All rights reserved.

DOI： 10.1016/j.bmc.2006.08.045

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記述言語：英語   掲載種別：研究論文（学術雑誌）   出版者・発行元：PERGAMON-ELSEVIER SCIENCE LTD  

A new C16N-type quaternary alkaloid, lycovatine A (1), has been isolated from the club moss Lycopodium clavatum var. robustum, and the structure including the relative stereochemistry was elucidated on the basis of spectroscopic data.

DOI： 10.3987/com-06-s(o)21

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記述言語：英語   掲載種別：研究論文（学術雑誌）   出版者・発行元：CELL PRESS  

Lymphocytes in T cell activation require extracellular nutrients to provide energy for cellular proliferation and effector functions. Therefore, inhibitors of nutrient transporters are expected to be a new class of immunosuppressant. Here, we report that the molecular target of brasilicardin A (BraA), an immunosuppressive compound, is the amino acid transporter system L. BraA inhibited the cell-cycle progression of murine T cell lymphocyte CTLL-2 cells in G1 phase, and potently inhibited the uptake of amino acids that are substrates for amino acid transport system L. Moreover, BraA stimulated the GCN2 activation and, subsequently, the phosphorylation of eIF2 alpha. These results suggest that the immunosuppressive activity of BraA is induced by amino acid deprivation via the inhibition of system L and that the amino acid transporter is a target for immunosuppressant.

DOI： 10.1016/j.chembiol.2006.09.006

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記述言語：英語   掲載種別：研究論文（学術雑誌）   出版者・発行元：AMER CHEMICAL SOC  

Four new oxindole alkaloids, paratunamides A-D (1-4), containing a secologanin unit, were isolated from the bark of Cinnamodendron axillare, and their structures and relative configurations were elucidated by spectroscopic data. The absolute configuration at C-7 in 1-4 was assigned as S, S, R, and S, respectively, on the basis of the CD spectra.

DOI： 10.1021/np0602968

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記述言語：英語   掲載種別：研究論文（学術雑誌）   出版者・発行元：PERGAMON-ELSEVIER SCIENCE LTD  

Four new alkaloids, lycopladines B-D (1-3) and lyconadin B (4), have been isolated from the club moss Lycopodium complanatum and the structures including the stereochemistry were elucidated on the basis of spectral data and modified Mosher's method. Lyconadin B (4) elevated NGF mRNA expression in 1321N1 human astrocytoma cells. (c) 2006 Elsevier Ltd. All rights reserved.

DOI： 10.1016/j.bmc.2006.05.028

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記述言語：英語   掲載種別：研究論文（学術雑誌）   出版者・発行元：WILEY-V C H VERLAG GMBH  

The biosynthesis of the antitumor antibiotic, ansamitocin, involves the assembly of a linear octaketide on the ansamitocin (asm) polyketide synthase (PKS), which is then cyclized to proansamitocin and further modified to the final product. In the first chain-extension step on the asm PKS, a stereocenter is generated which is then obliterated in a subsequent double-bond migration. The cryptic configuration at this stereocenter was determined by first synthesizing the two enantiomers of the intermediate diketide as their N-acetylcysteamine (SNAC) thioesters. These were then used to demonstrate that only the R enantiomer complements a 3-amino-5-hydroxybenzoic acid (AHBA) deficient mutant of Actinosynnema pretiosum to restore ansomitocin formation. The low efficiency of complementation by the diketide, compared to AHBA, is due to inefficient loading onto the PKS and not the inhibition of the enzyme. A presumed next chain-extension intermediate-the triketide with an unrearranged double bond-was also synthesized as its SNAC ester, but did not complement the AHBA(-) mutant.

DOI： 10.1002/cbic.200500506

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記述言語：英語   掲載種別：研究論文（学術雑誌）   出版者・発行元：JAPAN ANTIBIOTICS RESEARCH ASSOC  

A new polyketide metabolite, amphidinin B (1), has been isolated from a marine dinoflagellate Amphidinium sp. and the structure and absolute stereochemistry were elucidated on the basis of spectroscopic data and chemical means.

DOI： 10.1038/ja.2006.72

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記述言語：英語   掲載種別：研究論文（学術雑誌）   出版者・発行元：JAPAN ANTIBIOTICS RESEARCH ASSOC  

A new polyketide metabolite, amphidinin B (1), has been isolated from a marine dinoflagellate Amphidinium sp. and the structure and absolute stereochemistry were elucidated on the basis of spectroscopic data and chemical means.

DOI： 10.1038/ja.2006.72

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その他リンク： http://orcid.org/0000-0002-3553-5844

記述言語：英語   掲載種別：研究論文（学術雑誌）   出版者・発行元：PHARMACEUTICAL SOC JAPAN  

Cloning of polyketide synthase (PKS) gene for amphidinolide biosynthesis was attempted from a dinoflagellate Amphidinium sp. (strain Y-42). Fourteen beta-ketoacyl synthase gene fragments were obtained by Polymerase Chain Reaction (PCR) amplification from degenerated primer sets designed on the basis of the conserved amino acid sequences of beta-ketoacyl synthase domains in known type I PKSs. The PCR analysis using primer sets designed from these fourteen beta-ketoacyl synthase gene fragments revealed that these DNA sequences exist only in the dinoflagellates producing amphidinolides. The DNA sequence of the positive clone, which was isolated from genomic DNA library of Amphidinium sp. (strain Y-42) by PCR detection using the specific primer set, was analyzed by shotgun sequencing. The deduced gene products in the positive clone showed similarity with beta-ketoacyl synthase (KS), acyl transferase (AT), dehydratase (DH), ketoreductase (KR), and acyl carrier protein (ACP) in known type I PKSs and thioesterase (TE).

DOI： 10.1248/bpb.29.1314

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記述言語：英語   掲載種別：研究論文（学術雑誌）   出版者・発行元：PERGAMON-ELSEVIER SCIENCE LTD  

Amphezonol A (1), a novel polyhydroxyl linear carbon-chain metabolite, has been isolated from the cultured marine dinoflagellate Amphidinium sp., which was isolated from an Okinawan marine acoel flatworm Amphiscolops sp. The structure of 1 was elucidated by detailed analyses of 2D NMR spectra. Amphezonol A (1) possesses one tetrahydrofuran ring, two tetrahydropyran rings, and twenty-one hydroxyl groups on C-60-linear aliphatic chain with one exo-methylene and one methyl branch. Amphezonol A (1) exhibited a modest inhibitory activity against DNA polymerase alpha. (c) 2006 Elsevier Ltd. All rights reserved.

DOI： 10.1016/j.tetlet.2006.04.094

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記述言語：英語   掲載種別：研究論文（学術雑誌）   出版者・発行元：TAYLOR & FRANCIS LTD  

Iejimalides (IEJLs), 24-membered macrolides, are potent antitumor compounds, but their molecular targets remain to be revealed. In the course of screening, we identified IEJLs as potent osteoclast inhibitors. Since it is known that osteoclasts are sensitive to vacuolar H+-ATPase (V-ATPase) inhibitor, we investigated the effect of IEJLs on V-ATPases. IEJLs inhibited the V-ATPases of both mammalian and yeast cells in situ, and of. yeast V-ATPases in vitro. A bafilomycin-resistant yeast mutant conferred IEJL resistance, suggesting that IEJLs bind a site similar to the bafilomycins/concanamycins-binding site. These results indicate that IEJLs are novel V-ATPase inhibitors, and that antitumor and antiosteporotic activities are exerted via V-ATPase inhibition.

DOI： 10.1271/bbb.50644

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記述言語：英語   掲載種別：研究論文（学術雑誌）  

DOI： 10.1016/j.tet.2006.03.040

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記述言語：英語   掲載種別：研究論文（学術雑誌）   出版者・発行元：PERGAMON-ELSEVIER SCIENCE LTD  

A new C16N type alkaloid, lycopladine A (1), has been isolated from the club moss Lycopodium complanatum, and the structure and relative stereochemistry of 1 were elucidated on the basis of spectral data. (c) 2006 Elsevier Ltd. All rights reserved.

DOI： 10.1016/j.tetlet.2006.03.027

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記述言語：英語   掲載種別：研究論文（学術雑誌）   出版者・発行元：MOLECULAR DIVERSITY PRESERVATION INTERNATIONAL  

Manzamenones A similar to C (1 similar to 3) and E similar to F (5 similar to 6), unique oxylipin metabolites isolated from a marine sponge Plakortis sp., have been found to exhibit inhibitory activity against T-cell protein tyrosine phosphatase (TCPTP). The inhibitory activity of 2 and 5 against TCPTP was 4 times more potent than that against protein tyrosine phosphatase-1B (PTP1B).

DOI： 10.3390/md401009

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記述言語：英語   掲載種別：研究論文（学術雑誌）   出版者・発行元：PERGAMON-ELSEVIER SCIENCE LTD  

A novel cytotoxic bis-3-alkylpyridine alkaloid with an azoxy moiety, pyrinadine A (1), has been isolated from an Okinawan marine sponge Cribrochalina sp. (SS-1115), and the structure was elucidated by spectroscopic data and chemical means. (c) 2005 Elsevier Ltd. All rights reserved.

DOI： 10.1016/j.tetlet.2005.11.163

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記述言語：英語   掲載種別：研究論文（学術雑誌）   出版者・発行元：MOLECULAR DIVERSITY PRESERVATION INTERNATIONAL  

Luteophanol D ( 1), a new polyhydroxyl linear carbon-chain metabolite, has been isolated from the cultured marine dinoflagellate Amphidinium sp., which was isolated from Okinawan marine acoel flatworm Pseudaphanostoma luteocoloris. The structure of 1 was elucidated by detailed analyses of 2D NMR spectra. Luteophanol D ( 1) possesses two tetrahydropyran rings and twenty-three hydroxyl groups on C-63-linear aliphatic chain with one exo-methylene and two methyl branches.

DOI： 10.3390/md304113

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掲載種別：研究論文（学術雑誌）   出版者・発行元：MDPI} {AG  

A new cytotoxic 25-membered macrolide, amphidinolide C2 (1), has been isolated from marine dinoflagellate Amphidinium sp. (Y-71 strain), and the structure 1 was elucidated on the basis of spectroscopic data and chemical means.

DOI： 10.3390/md203083

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記述言語：英語   掲載種別：研究論文（学術雑誌）   出版者・発行元：PERGAMON-ELSEVIER SCIENCE LTD  

Two of each diastereomers of the C-1-C-10 and C-17-C-29 segments of amphidinolide C (1) were synthesized. Comparing the H-1 NMR chemical shifts of its MTPA esters with those of linear methyl ester of 1, the absolute configurations at C-7, C-8, C-20, C-23, and C-24 in amphidinolide C (1) were confirmed to be all R. (C) 2003 Elsevier Science Ltd. All rights reserved.

DOI： 10.1016/S0040-4020(03)00142-X

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記述言語：英語   掲載種別：研究論文（国際会議プロシーディングス）   出版者・発行元：Walter de Gruyter GmbH  

Absolute stereochemistry of amphidinolides G and H, potent cytotoxic 27- and 26-membered macrolides, respectively, isolated from a marine dinofiagellate Amphidinium sp., was determined by X-ray diffraction analysis, synthesis of a degradation product, and chemical interconversion. Six new macrolides, amphidinolides H2∼H5, G2, G3, and W, have been isolated from a marine dinoflagellate Amphidinium sp. (strain Y-42), and the structures were elucidated by 2D NMR data and chemical means. The structure-activity relationship of amphidinolide H-type macrolides for cytotoxicity was examined. The biosynthetic origins of amphidinolides B, C, H, J, T1, and W were investigated on the basis of 13C NMR data of 13C-enriched samples obtained by feeding experiments with [1-13C], [2-13C], and [1,2-13C2] sodium acetates in cultures of the dinoflagellates. Five novel long-chain polyhydroxyl compounds, colopsinols A∼E, were obtained from the Amphidinium sp. (strain Y-5).

DOI： 10.1351/pac200375020337

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その他リンク： http://orcid.org/0000-0002-3553-5844

記述言語：英語   掲載種別：研究論文（学術雑誌）   出版者・発行元：AMER CHEMICAL SOC  

The absolute configurations at eight chiral centers in amphidinolide E (1), a cytotoxic 19-membered macrolide isolated from a marine dinoflagellate Amphidinium sp., were determined to be 2R, 7R, 8R, 13S, 16S, 17R, 18R, and 19R on the basis of detailed analysis of NMR data and by chemical means.

DOI： 10.1021/jo016326n

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記述言語：英語   掲載種別：研究論文（学術雑誌）   出版者・発行元：PHARMACEUTICAL SOC JAPAN  

The biosynthetic origins of amphidinolide B (1) were investigated on the basis of C-13-NMR data of C-13-enriched samples obtained by feeding experiments with [1-C-13], [2-C-13], and [1,2-C-13(2)] sodium acetates in cultures of a dinoflagellate Amphidinium sp. These incorporation patterns suggested that 1 was generated from three successive polyketide chains, an isolated C-1 unit from C-2 of acetates, six branched C-1 units from C-2 of acetates, and an "m-m" and an "m-m-m" unit derived only from C-2 of acetates. The labeling patterns of amphidinolide B (1) were different from those of amphidinolide H (2), a 26-membered macrolide closely related to 1.

DOI： 10.1248/cpb.49.1366

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記述言語：英語   掲載種別：研究論文（学術雑誌）   出版者・発行元：PERGAMON-ELSEVIER SCIENCE LTD  

Amphidinolide T5 (1), a new 19-membered macrolide related to amphidinolide T1 (2), has been isolated from a marine dinoflagellate Amphidinium sp. The structure of 1 was elucidated on the basis of spectroscopic data and chemical means. The stereostructure of amphidinolide T1 (2) was confirmed by a single crystal X-ray diffraction analysis. (C) 2001 Elsevier Science Ltd. All rights reserved.

DOI： 10.1016/S0040-4020(01)00591-9

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記述言語：英語   掲載種別：研究論文（学術雑誌）   出版者・発行元：PERGAMON-ELSEVIER SCIENCE LTD  

The biosynthetic origins of amphidinolide C (1) were investigated on the basis of C-13 NMR data of C-13 enriched samples obtained by feeding experiments with [1-C-13], [2-C-13], and [1,2-(13)C2] sodium acetates in cultures of a dinoflagellate Amphidinium sp. These incorporation patterns suggested that amphidinolide C (1) was generated from four diketide chains, four acetate units, five isolated C-1 unit from C-2 of acetates, seven branched C-1 units from C-2 of acetates, and a 'm-m' and a 'm-m-m' units derived only from C-2 of acetates. (C) 2001 Elsevier Science Ltd. All rights reserved.

DOI： 10.1016/S0040-4020(01)00556-7

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記述言語：英語   掲載種別：研究論文（学術雑誌）   出版者・発行元：AMER CHEMICAL SOC  

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The absolute configurations at 12 chiral centers in amphidinolide C (1), a potent cytotoxic 25-membered macrolide isolated from a marine dinoflagellate Amphidinium sp,, were determined to be 3S, 4R, 6R, 7R, 8R, 12R 135, 16S, 20R, 23R, 24R, and 29S by combination of NMR analyses, degradation experiments, and synthesis of the C-1-C-7 segment.

DOI： 10.1021/ol015741z

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記述言語：英語   掲載種別：研究論文（学術雑誌）   出版者・発行元：AMER CHEMICAL SOC  

Three new 19-membered macrolides, amphidinolides T2 (2), T3 (3), and T4 (4), structurally related to amphidinolide T1 (1) have been isolated from two strains of marine dinoflagellates of the genus Amphidinium. The structures of 2-4 were elucidated on the basis of spectroscopic data. The absolute configurations at C-7, C-8, and C-10 of 1-4 were determined by comparison of NMR data of their C-1-C-12 segments with those of synthetic model compounds for the tetrahydrofuran portion. The biosynthetic origins of amphidinolide TI (1) were investigated on the basis of C-13 NMR data of a C-13 enriched sample obtained by feeding experiments with [1-C-13], [2-C-13], and [1,2-C-13(2)] sodium acetates and C-13-labeled sodium bicarbonstte in the cultures of the dinoflagellate. These incorporation patterns suggested that amphidinolide T1 (1) was generated from four successive palyketide chains, an isolated C-1 unit formed from C-2 of acetates, and three unusual Ct units derived only from C-2 of acetates. Furthermore, it is noted that five oxygenated carbons of C-l, C-7, C-12, C-13, and C-18 were not derived from the C-1 carbonyl, but from the C-2 methyl of acetates.

DOI： 10.1021/jo005607c

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記述言語：英語   掲載種別：研究論文（学術雑誌）   出版者・発行元：PERGAMON-ELSEVIER SCIENCE LTD  

Two new cytotoxic bromotyrosine alkaloids, ma'edamines A (1) and B (2), with a unique 2(1H)pyrazinone ring have been isolated from the Okinawan marine sponge Suberea sp. The structures were elucidated on the basis of spectroscopic data. (C) 2000 Elsevier Science Ltd. All rights reserved.

DOI： 10.1016/S0040-4020(00)00732-8

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記述言語：英語   掲載種別：研究論文（学術雑誌）   出版者・発行元：PHARMACEUTICAL SOC JAPAN  

Colopsinols D (1) and E (2), two new polyhydroxyl linear carbon chain compounds, have been isolated from the cultured marine dinoflagellate Amphidinium sp. The structures of 1 and 2 were elucidated on the basis of two-dimensional NMR and FAB-MS/MS data.

DOI： 10.1248/cpb.48.1447

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記述言語：英語   掲載種別：研究論文（学術雑誌）   出版者・発行元：PHARMACEUTICAL SOC JAPAN  

New bis-pyridine alkaloids, pyrinodemins B-D (1-3), have been isolated together with pyrinodemin A (4) and related 3-alkyl pyridine alkaloids 5-8 from the Okinawan marine sponge Amphimedon sp. and the structures were elucidated from spectroscopic data. Pyrinodemins B-D (1-3) showed potent cytotoxicity, while compounds 5-8 exhibited antimicrobial activity.

DOI： 10.1248/cpb.48.974

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記述言語：英語   掲載種別：研究論文（学術雑誌）   出版者・発行元：PHARMACEUTICAL SOC JAPAN  

New bis-pyridine alkaloids, pyrinodemins B-D (1-3), have been isolated together with pyrinodemin A (4) and related 3-alkyl pyridine alkaloids 5-8 from the Okinawan marine sponge Amphimedon sp. and the structures were elucidated from spectroscopic data. Pyrinodemins B-D (1-3) showed potent cytotoxicity, while compounds 5-8 exhibited antimicrobial activity.

DOI： 10.1248/cpb.48.974

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記述言語：英語   掲載種別：研究論文（学術雑誌）   出版者・発行元：PERGAMON-ELSEVIER SCIENCE LTD  

A novel 14-membered polyene macrolide, amphidinolide V (1), has been isolated from a marine dinoflagellate Amphidinium sp., and the structure was elucidated by spectroscopic data. The relative stereochemistry of C-8, C-9, C-10, and C-13 was elucidated by NOESY correlations. Amphidinolide V (1) possessing five exo-methylenes and one epoxide exhibited cytotoxicity against tumor cell lines. (C) 2000 Elsevier Science Ltd. All rights reserved.

DOI： 10.1016/S0040-4039(99)02170-X

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記述言語：英語   掲載種別：研究論文（学術雑誌）   出版者・発行元：ROYAL SOC CHEMISTRY  

Colopsinols B (1) and C (2), unique polyhydroxy compounds consisting of a C-53-linear aliphatic chain with three C-1 branches, three ether rings, six hydroxy groups, a glucoside moiety, and a sulfate ester have been isolated from the cultured marine dinoflagellate Amphidinium sp. The structures of 1 and 2 were elucidated on the basis of extensive NMR techniques as well as FABMS/MS data of the peroxide (3) of 2.

DOI： 10.1039/a906296c

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記述言語：英語   掲載種別：研究論文（学術雑誌）   出版者・発行元：PERGAMON-ELSEVIER SCIENCE LTD  

Two new theonellapeptolide-related cyclic depsipeptides (1 and 2) have been isolated from an Okinawan marine sponge Theonella sp. and the structures were elucidated on the basis of the 2D NMR data, PSD analysis of MALDI-TOFMS, and chemical means. Compound 1 was a theonellapeptolide congener possessing a methylsulfinylacetyl group at the N-terminus, while 2 was another theonellapeptolide congener having an acetyl group at the N-terminus. Compounds 1 and 2 exhibited antimicrobial activity. (C) 1999 Elsevier Science Ltd. All rights reserved.

DOI： 10.1016/S0040-4020(99)00586-4

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記述言語：英語   掲載種別：研究論文（学術雑誌）   出版者・発行元：PERGAMON-ELSEVIER SCIENCE LTD  

A novel cytotoxic pyridine alkaloid, pyrinodemin A (1), with a unique cis-cyclopent[c]isoxazolidine moiety has been isolated from the Okinawan marine sponge Amphimedon sp., and the structure was elucidated from 2D NMR data and EIMS fragmentation. (C) 1999 Elsevier Science Ltd. All rights reserved.

DOI： 10.1016/S0040-4039(99)00852-7

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記述言語：英語   掲載種別：研究論文（学術雑誌）   出版者・発行元：PERGAMON-ELSEVIER SCIENCE LTD  

A novel cytotoxic pyridine alkaloid, pyrinodemin A (1), with a unique cis-cyclopent[c]isoxazolidine moiety has been isolated from the Okinawan marine sponge Amphimedon sp., and the structure was elucidated from 2D NMR data and EIMS fragmentation. (C) 1999 Elsevier Science Ltd. All rights reserved.

DOI： 10.1016/S0040-4039(99)00852-7

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その他リンク： http://orcid.org/0000-0002-3553-5844

記述言語：英語   掲載種別：研究論文（学術雑誌）   出版者・発行元：AMER CHEMICAL SOC  

Colopsinol A (1), a novel polyhydroxyl compound, has been isolated from the cultured marine dinoflagellate Amphidiniun sp., from which a number of cytotoxic macrolides, amphidinolides, have been obtained to date, and the gross structure of 1 was elucidated on the basis of extensive spectroscopic analyses including recent 2D NMR techniques of CH2-seIected editing HSQC as well as FABMS/MS experiments and chemical means. Colopsinol A (1), C71H119O25SNa, is the first member of a new class of polyketide natural products possessing a gentiobioside moiety and a sulfate eater. The polyketide aglycon consisted of a C-56-linear aliphatic chain with one exo-methylene and two methyl branches as well as two ketones, five hydroxyl groups, and a tetrahydropyran and two epoxide rings.

DOI： 10.1021/jo981882b

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記述言語：英語   掲載種別：研究論文（学術雑誌）   出版者・発行元：ROYAL SOC CHEMISTRY  

Colopsinols B (1) and C (2), unique polyhydroxy compounds consisting of a C-53-linear aliphatic chain with three C-1 branches, three ether rings, six hydroxy groups, a glucoside moiety, and a sulfate ester have been isolated from the cultured marine dinoflagellate Amphidinium sp. The structures of 1 and 2 were elucidated on the basis of extensive NMR techniques as well as FABMS/MS data of the peroxide (3) of 2.

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記述言語：英語   掲載種別：研究論文（学術雑誌）   出版者・発行元：PERGAMON-ELSEVIER SCIENCE LTD  

Luteophanols B (1) and C (2), new polyhydroxyl linear carbon-chain compounds, have been isolated from the cultured marine dinoflagellate Amphidinium sp. The structures of 1 and 2 were elucidated by detailed analyses of two-dimensional NMR data containing HMBC, HMQC-RELAY, CH2-selected E-HSQC, and CH2-selected E-HSQC, TOCSY. (C) 1998 Elsevier Science Ltd. All rights reserved.

DOI： 10.1016/S0040-4020(98)00898-9

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記述言語：英語   掲載種別：研究発表ペーパー・要旨（国際会議）   出版者・発行元：GEORG THIEME VERLAG KG  

DOI： 10.1055/s-0036-1596659

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記述言語：英語   掲載種別：研究発表ペーパー・要旨（国際会議）   出版者・発行元：GEORG THIEME VERLAG KG  

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記述言語：日本語   出版者・発行元：公益社団法人日本生物工学会  

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記述言語：英語   出版者・発行元：PERGAMON-ELSEVIER SCIENCE LTD  

DOI： 10.1016/j.tet.2009.05.081

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記述言語：日本語   出版者・発行元：天然有機化合物討論会  

Sesquiterpenoid quinines and hydroquinones are representative marine natural products with unique structures and interesting biological activities. In our continuous search for bioactive compounds having unique structures from Okinawan marine sponges, we have isolated new sesquiterpenoid quinones, nakijiquinones E〜I (1〜5) and metachromins L-Q (6〜11), from three collections of Okinawan marine sponges. The structures of 1〜5 were elucidated on the basis of 2D NMR data, while those of 6〜11 were established by chemical correlations. Furthermore, biological activities for 1〜11 and synthetic metac...

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記述言語：日本語   出版者・発行元：天然有機化合物討論会  

Bromopyrrole alkaloids are known to be one of the most common metabolites contained in marine sponges. During our search for bioactive substances from marine organisms, we have isolated bromopyrrole alkaloids with unique cyclic skeletons from sponges of the genus Agelas or Hymeniacidon. Recently, three new bromopyrrole alkaloids, nagelamides K, M, and N (1-3), have been isolated from an Okinawan marine sponge Agelas sp. (SS-1134). The structures and relative stereochemistry of 1〜3 were elucidated on the basis of spectroscopic data. Nagelamide K (1) is a new dimeric bromopyrrole alkaloid pos...

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記述言語：日本語   出版者・発行元：天然有機化合物討論会  

Daphniphyllum alkaloids are a structually diverse group of natural products with unique fused-heterocyclic skeletons, which are elaborated by trees of the genus Daphniphyllum (Daphniphyllaceae). These unusual ring systems have been challenging targets for total synthesis as well as biosynthetic studies. We have isolated novel types of Daphniphyllum alkaloids from Daphniphyllum macropodum, D. humile, D. teijsmanni, and D. glaucescense. In our continuing search for structually unique and biogenetically interesting new alkaloids, calyciphyllines C-G (1-5) have been isolated from D. calycinum, ...

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記述言語：日本語   出版者・発行元：東京化学同人  

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記述言語：日本語   出版者・発行元：天然有機化合物討論会実行委員会  

Diffusion-ordered NMR spectroscopy (DOSY) is a versatile and powerful NMR technique and a noninvasive analytical method for mixture analysis that does not require prior physical separation of the analysis. In our search for new metabolites from natural resources, DOSY was applied for constituent analysis of crude bromopyrrole fractions separated from an Okinawan marine sponge Agelas sp. (SS-1056) so that two new bromopyrrole alkaloids, agesamides A (1) and B (2), have been isolated. The structures and relative stereochemistry of 1 and 2 were elucidated fromspectroscopic data. Furthermore, two new bromopyrrole alkaloids, nagelamides J (3) and K (4), have been isolated from another Okinawan marine sponge Agelas sp. (SS-1077), and the structures and relative stereochemistries were elucidated from spectroscopic data. Nagelamide J (3) is the first bromopyrrole alkaloid possessing a cyclopentane ring fused to an amino imidazole ring and nagelamide K (4) is a unique dimeric bromopyrrole alkaloid containing an ester linkage. Nagelamide J (3) exhibited antimicrobial activity against Staphylococcus aureus (MIC, 8.35μg/ml) and antifungal activity against Cryptococcus neoformans (MIC, 16.7μg/ml), while nagelamide K (4) exhibited antimicrobial activity against Micrococcus luteus (MIC, 16.7μg/ml).

DOI： 10.24496/tennenyuki.49.0_1

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記述言語：日本語   出版者・発行元：天然有機化合物討論会実行委員会  

Diffusion-ordered NMR spectroscopy (DOSY) is a versatile and powerful NMR technique and a noninvasive analytical method for mixture analysis that does not require prior physical separation of the analysis. In our search for new metabolites from natural resources, DOSY was applied for constituent analysis of crude bromopyrrole fractions separated from an Okinawan marine sponge Agelas sp. (SS-1056) so that two new bromopyrrole alkaloids, agesamides A (1) and B (2), have been isolated. The structures and relative stereochemistry of 1 and 2 were elucidated fromspectroscopic data. Furthermore, two new bromopyrrole alkaloids, nagelamides J (3) and K (4), have been isolated from another Okinawan marine sponge Agelas sp. (SS-1077), and the structures and relative stereochemistries were elucidated from spectroscopic data. Nagelamide J (3) is the first bromopyrrole alkaloid possessing a cyclopentane ring fused to an amino imidazole ring and nagelamide K (4) is a unique dimeric bromopyrrole alkaloid containing an ester linkage. Nagelamide J (3) exhibited antimicrobial activity against Staphylococcus aureus (MIC, 8.35μg/ml) and antifungal activity against Cryptococcus neoformans (MIC, 16.7μg/ml), while nagelamide K (4) exhibited antimicrobial activity against Micrococcus luteus (MIC, 16.7μg/ml).

DOI： 10.24496/tennenyuki.49.0_1

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記述言語：日本語   出版者・発行元：天然有機化合物討論会  

Club moss (Lycopodiaceae) is known to be a rich source of Lycopodium alkaloids posessing unique heterocyclic ring systems such as C_<16>N, C_<16>N_2, and C_<27>N_3, which have attracted great interest from biogenetic, synthetic, and biological points of view. In our continuing efforts to find new Lycopodium alkaloids, lycopladines A-D (1-4), lyconadin B (5), and complanadines C (6), D (7) were isolated from the club moss Lycopodium complanatum. The structures for 1-7 were elucidated on the basis of spectral data. Lycopladine A (1) obtained as colorless amourphous solid, showed the pseudomol...

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記述言語：日本語   出版者・発行元：日本薬学会  

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記述言語：日本語   出版者・発行元：天然有機化合物討論会実行委員会  

Amphezonol A (1), a novel polyhydroxyl compound, was isolated from a marine dinoflagellate Amphidinium sp. (Y-72), and the structure was elucidated on the basis of 2D NMR data including HSQC-TOCSY and INADEQUATE spectra (920MHz) using the ^<13>C-enriched sample. Amphezonol A (1), C_<62>H_<114>O_<24>, was the first member of a new class of polyketide natural products consisting of a C_<60>-linear aliphatic chain with twenty-one hydroxyl groups, and two tetrahydropyran and a tetrahydrofuran rings. Cloning of polyketide synthase (PKS) gene from a dinoflagellate Amphidinium sp. was attempted and PKS gene fragments were obtained by PCR amplification from degenerated primer sets designed on the basis of the conserved amino acid sequences in known type I PKSs. The PCR analysis, using primer sets designed from these PKS gene fragments, revealed that these DNA sequences exist only in the dinoflagellates producing polyketides.

DOI： 10.24496/tennenyuki.47.0_151

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記述言語：日本語   出版者・発行元：天然有機化合物討論会実行委員会  

Amphezonol A (1), a novel polyhydroxyl compound, was isolated from a marine dinoflagellate Amphidinium sp. (Y-72), and the structure was elucidated on the basis of 2D NMR data including HSQC-TOCSY and INADEQUATE spectra (920MHz) using the ^<13>C-enriched sample. Amphezonol A (1), C_<62>H_<114>O_<24>, was the first member of a new class of polyketide natural products consisting of a C_<60>-linear aliphatic chain with twenty-one hydroxyl groups, and two tetrahydropyran and a tetrahydrofuran rings. Cloning of polyketide synthase (PKS) gene from a dinoflagellate Amphidinium sp. was attempted and PKS gene fragments were obtained by PCR amplification from degenerated primer sets designed on the basis of the conserved amino acid sequences in known type I PKSs. The PCR analysis, using primer sets designed from these PKS gene fragments, revealed that these DNA sequences exist only in the dinoflagellates producing polyketides.

DOI： 10.24496/tennenyuki.47.0_151

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記述言語：日本語   出版者・発行元：(公社)日本薬学会  

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記述言語：日本語   出版者・発行元：天然有機化合物討論会実行委員会  

Amphidinolide C (1) is a unique 25-membered macrolide isolated from a marine dinoflagellate Amphidinium sp. (strain Y-5). The gross structure of 1 has been elucidated by 2D-NMR data, whereas the stereochemistry remains undefined. During our search for bioactive metabolites from marine dinoflagellates, relatively large amounts of 1 have been recently isolated from two strains (Y-56 and Y-71) of the genus Amphidinium, which allowed us to investigate the stereochemistry of 1 Absolute configurations at C-12, C-13, C-20, C-23, C-24, and C-29 of amphidinolide C (1) were assigned by combination of NMR analyses including J-based configuration analysis and Mosher's method, while absolute configurations at C-7 and C-8 of 1 were assigned by application of Mosher's method for erythro glycol and comparison of ^1H-NMR data of natural specimen with those of synthetic C-1-C-10 segments. Absolute configurations at C-3, C-4, C-6, and C-16 of 1 were elucidated by comparison of NMR data of degradation products of 1 with synthetic C-1-C-7 and C-16-C-18 segments. On the other hand, five new 19-membered macrolides amphidinolides T1-T5 (2-6) have been isolated from the Y-56 and Y-71 strains of the genus Amphdinium. The gross structures were elucidated by 2D-NMR analyses. Absolute configurations at C-2, C-13, C-14, and C-18 of amphidinolide T1 (2) were assigned on the basis of NMR data of the MTPA esters of 2 and those of degradation products of 2, while absolute configurations at C-7, C-8, and C-10 of 2 were elucidated by comparison of ^1H-NMR data of C-1-C-12 segment with those of synthetic model compounds for tetrahydrofuran portion. The absolute stereochemistry of amphidinolides T2-T5 (3-6) were also elucidated by similar methods. The stereostructure of 2 was also confirmed by a single crystal X-ray diffraction analysis.

DOI： 10.24496/tennenyuki.43.0_97

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記述言語：日本語   出版者・発行元：天然有機化合物討論会実行委員会  

Amphidinolide C (1) is a unique 25-membered macrolide isolated from a marine dinoflagellate Amphidinium sp. (strain Y-5). The gross structure of 1 has been elucidated by 2D-NMR data, whereas the stereochemistry remains undefined. During our search for bioactive metabolites from marine dinoflagellates, relatively large amounts of 1 have been recently isolated from two strains (Y-56 and Y-71) of the genus Amphidinium, which allowed us to investigate the stereochemistry of 1 Absolute configurations at C-12, C-13, C-20, C-23, C-24, and C-29 of amphidinolide C (1) were assigned by combination of NMR analyses including J-based configuration analysis and Mosher's method, while absolute configurations at C-7 and C-8 of 1 were assigned by application of Mosher's method for erythro glycol and comparison of ^1H-NMR data of natural specimen with those of synthetic C-1-C-10 segments. Absolute configurations at C-3, C-4, C-6, and C-16 of 1 were elucidated by comparison of NMR data of degradation products of 1 with synthetic C-1-C-7 and C-16-C-18 segments. On the other hand, five new 19-membered macrolides amphidinolides T1-T5 (2-6) have been isolated from the Y-56 and Y-71 strains of the genus Amphdinium. The gross structures were elucidated by 2D-NMR analyses. Absolute configurations at C-2, C-13, C-14, and C-18 of amphidinolide T1 (2) were assigned on the basis of NMR data of the MTPA esters of 2 and those of degradation products of 2, while absolute configurations at C-7, C-8, and C-10 of 2 were elucidated by comparison of ^1H-NMR data of C-1-C-12 segment with those of synthetic model compounds for tetrahydrofuran portion. The absolute stereochemistry of amphidinolides T2-T5 (3-6) were also elucidated by similar methods. The stereostructure of 2 was also confirmed by a single crystal X-ray diffraction analysis.

DOI： 10.24496/tennenyuki.43.0_97

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記述言語：日本語  

J-GLOBAL

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記述言語：日本語  

J-GLOBAL

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記述言語：日本語   出版者・発行元：天然有機化合物討論会実行委員会  

Marine dinoflagellates of the genus Amphidinium have been recognized as a rich source of novel bioactive substances with unique structures. We previously isolated a series of cytotoxic macrolides, designated amphidinolides, possessing unique structural features from several strains of the dinoflagellates Amphidinium sp., among which the strain Y-5 was the richest source of the amphidinolides. Further search for metabolites from the strain Y-5, which was a symbiont of Okinawan marine acoel flatworm Amphiscolops sp., resulted in the isolation of two novel polyhydoroxyl compounds, colopsinols A (1) and B (2), belonging to a new class of polyketide metabolites. The structures of 1 and 2 were elucidated on the basis of extensive NMR techniques including a newly developed 2D NMR experiments such as CH_2-selected editing HSQC (E-HSQC) as well as FABMS/MS data. Colopsinols A (1) and B (2) are new class of polyketide natural products consisting of C_<56> and C_<53>-liner carbon chains, respectively, possessing a gentiobioside (β-D-glucopyranosyl-(1-6)-β-D-glucopyranoside) moiety and a sulfate ester. From this strain (Y-5), 13 cytotoxic macrolides, amphidinolides A-D, J, K, and M-S, have been isolated so far. Biosynthetically it is interesting that quite different type of polyketides such as colopsinols and amphidinolides are produced from the same dinoflagellate. Colopsinol A (1) showed inhibitory activity against DNA polymerase α and β with IC_<50> values of 13 and 7μM, respectively.

DOI： 10.24496/tennenyuki.41.0_595

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J-GLOBAL

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記述言語：日本語   出版者・発行元：天然有機化合物討論会実行委員会  

Marine dinoflagellates of the genus Amphidinium have been recognized as a rich source of novel bioactive substances with unique structures. We previously isolated a series of cytotoxic macrolides, designated amphidinolides, possessing unique structural features from several strains of the dinoflagellates Amphidinium sp., among which the strain Y-5 was the richest source of the amphidinolides. Further search for metabolites from the strain Y-5, which was a symbiont of Okinawan marine acoel flatworm Amphiscolops sp., resulted in the isolation of two novel polyhydoroxyl compounds, colopsinols A (1) and B (2), belonging to a new class of polyketide metabolites. The structures of 1 and 2 were elucidated on the basis of extensive NMR techniques including a newly developed 2D NMR experiments such as CH_2-selected editing HSQC (E-HSQC) as well as FABMS/MS data. Colopsinols A (1) and B (2) are new class of polyketide natural products consisting of C_<56> and C_<53>-liner carbon chains, respectively, possessing a gentiobioside (β-D-glucopyranosyl-(1-6)-β-D-glucopyranoside) moiety and a sulfate ester. From this strain (Y-5), 13 cytotoxic macrolides, amphidinolides A-D, J, K, and M-S, have been isolated so far. Biosynthetically it is interesting that quite different type of polyketides such as colopsinols and amphidinolides are produced from the same dinoflagellate. Colopsinol A (1) showed inhibitory activity against DNA polymerase α and β with IC_<50> values of 13 and 7μM, respectively.

DOI： 10.24496/tennenyuki.41.0_595

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記述言語：日本語  

J-GLOBAL

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記述言語：日本語   出版者・発行元：天然有機化合物討論会実行委員会  

During our continuing search for structurally unique secondary metabolites from marine dinoflagellates, we previously isolated a series of cytotoxic macrolides, amphidinolides, from dinoflagellates Amphidinium sp. Recently we investigated another strain of Amphidinium sp. (strain number Y-52), which was isolated from the inside cells of the Okinawan marine acoel flatworm Pseudaphanostoma luteocoloris, and isolated two new polyhydroxyl compounds, luteophanols B (1) and C (2), both consisting of a C_<64>-linear aliphatic chain. The structure elucidation of 1 and 2 were elucidated on the basis of chemical degradation and newly developed 2D NMR experiments, E-HSQC and E-HSQC-TOCSY. E-HSQC and E-HSQC-TOCSY are very useful techniques for structure elucidations of complex natural products possessing many aliphatic methine and methylene carbons such as luteophanols B (1) and C (2). CH_2-selected E-HSQC-TOCSY^6 experiments seem to be suitable to assign very closely resonated carbon signals, since this method affords the high resolution in F_1 axis by limiting the F_1 spectral width, in which sp^2 methylene carbons are resonated.

DOI： 10.24496/tennenyuki.40.0_473

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J-GLOBAL

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記述言語：日本語   出版者・発行元：天然有機化合物討論会実行委員会  

During our continuing search for structurally unique secondary metabolites from marine dinoflagellates, we previously isolated a series of cytotoxic macrolides, amphidinolides, from dinoflagellates Amphidinium sp. Recently we investigated another strain of Amphidinium sp. (strain number Y-52), which was isolated from the inside cells of the Okinawan marine acoel flatworm Pseudaphanostoma luteocoloris, and isolated two new polyhydroxyl compounds, luteophanols B (1) and C (2), both consisting of a C_<64>-linear aliphatic chain. The structure elucidation of 1 and 2 were elucidated on the basis of chemical degradation and newly developed 2D NMR experiments, E-HSQC and E-HSQC-TOCSY. E-HSQC and E-HSQC-TOCSY are very useful techniques for structure elucidations of complex natural products possessing many aliphatic methine and methylene carbons such as luteophanols B (1) and C (2). CH_2-selected E-HSQC-TOCSY^6 experiments seem to be suitable to assign very closely resonated carbon signals, since this method affords the high resolution in F_1 axis by limiting the F_1 spectral width, in which sp^2 methylene carbons are resonated.

DOI： 10.24496/tennenyuki.40.0_473

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