Language：English   Publishing type：Research paper (scientific journal)   Publisher：The Japan Institute of Heterocyclic Chemistry  

DOI： 10.3987/com-22-14651

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Two new guaianolide sesquiterpenes, lanicepines A (1) and B (2), possessing unusual amino acid-derived substituents at C-13, were isolated from the flowering aerial parts of Saussurea laniceps, a traditional herbal medicine also known as "snow lotus". The structures of 1 and 2 were elucidated based on spectroscopic analysis including applications of the modified Mosher's method and Marfey's method as well as ECD calculations. Lanicepine A (1) contains a dihydropyridinone moiety with a carbamoyl and a hydroxymethyl group. This substituent was considered to consist of asparagine and a C4 unit. In contrast, lanicepine B (2) has a substituent that seems to be derived from l-proline and a C4 unit. Lanicepines A (1) and B (2) and two related known sesquiterpenes isolated from the same plant material, 11β,13-dihydrodesacylcynaropicrin (3) and 11β,13-dihydrodesacylcynaropicrin 8-O-β-d-glucoside (4), demonstrated inhibitory activity against IL-1β production from LPS-stimulated microglial cells.

DOI： 10.1021/acs.jnatprod.1c01069

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Language：English   Publishing type：Research paper (scientific journal)   Publisher：SAGE Publications  

Static blood (Oketsu) is a blood disorder of Kampo medicine. Many natural medicines have been used to cure static blood, and these drugs are called blood stasis-resolving formula. Some of these were reported to inhibit blood coagulation. Jidabokuippo (JDI), one of the blood stasis-resolving formulas, has been used to treat bruises and sprains. In this study, we evaluated the antithrombin activity of JDI and its active compounds using thrombin and an artificial substrate. Bioassay-guided isolation was performed for JDI, and the active compounds were identified using spectral data (NMR spectroscopy and mass spectrometry) by comparison with reported data. JDI depressed thrombin activity in a dose-dependent manner, ranging from 0.125 to 1 mg/mL. Chrysophanol-1- O-β-D-glucoside (1) and chrysophanol-8- O-β-D-glucoside (2) were obtained from JDI and showed thrombin inhibitory activity. This study provided the first report of the antithrombin effect of JDI and the isolation from it of two active compounds (1 and 2). These findings might contribute to the understanding of the mechanism of static blood and blood stasis-resolving formula.

DOI： 10.1177/1934578x221074529

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The production and accumulation of advanced glycation end products (AGEs) have been implicated in diabetes and diabetic complication. This study was conducted as a search for an AGE inhibitor from brown alga, Sargassum macrocarpum. Separation and purification were performed using AGEs inhibitory activity as an index, yielding isolation of 11 meroterpenoids, of which 3 were new compounds: macrocarquinoids A (1), B (6), and C (9). Their structures were elucidated using NMR spectral analysis with 2D techniques. All tested compounds showed AGEs inhibitory activity. Particularly, macrocarquinoid C (9) possessed the strongest activity (IC50: 1.0 mM) of isolated compounds. This activity was stronger than that of aminoguanidine (positive control).

DOI： 10.1007/s11418-020-01449-y

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Two new polyacetylene glycosides, kamiohnoyneosides A and B, were isolated from the flowers of edible Chrysanthemum "Kamiohno", along with a known polyacetylene glycoside and two known monoterpene glycosides. The structures of new compounds were elucidated on the basis of spectroscopic data. Kamiohnoyneoside A and three known compounds moderately inhibited formation of Nε-(carboxymethyl)lysine, one of the representative advanced glycation endproducts.

DOI： 10.1007/s11418-020-01443-4

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The manzamine alkaloids are absolutely one of the most fascinating marine natural products. The representative manzamine alkaloids, manzamines A-C, were isolated from a marine sponge Haliclona sp. collected off Cape Manzamo, Okinawa, Japan. The manzamine alkaloids are a unique class of alkaloids possessing a characteristic heterocyclic system, and exhibit a diverse range of bioactivities including cytotoxicity, antimicrobial activity, antimalarial activity, antiviral and antiinflammatory activities, antiinsecticidal activity, and proteasome inhibitory activity. About 100 manzamine alkaloids have been isolated from more than 16 species of marine sponges belonging to 5 families. The unusual ring systems, an intriguing suggested biogenetic pathway, and promising biological activities of manzamine alkaloids have attracted great interest as challenging targets for the total synthesis. This review is the continuation of the previous review published in volume 60 of The Alkaloids and covers isolation, structure elucidation, biosynthesis and biogenesis, chemical synthesis, and biological activity of manzamine alkaloids reported from 2003 to 2018.

DOI： 10.1016/bs.alkal.2020.03.001

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Two new bromotyrosine alkaloids, ma'edamines C and D, were isolated from an Okinawan marine sponge Suberea sp. The structures of ma'edamines C and D were elucidated on the basis of spectroscopic data. Ma'edamines C and D were the first natural products possessing a unique tetrasubstituted pyridinium moiety such as N-alkyl-3,5-diethyl-2-propylpyridinium and N-alkyl-3,5-diethyl-4-propylpyridinium, respectively. Ma'edamines C and D exhibited moderate cytotoxicity against murine leukemia cell line L1210 in vitro.

DOI： 10.1021/acs.orglett.9b03457

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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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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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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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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 25.0µM, while 1 and 3 possessed significant antibacterial activities against B. subtilis with MICs of 12.5 and 25.0µM, respectively. In contrast, cytotoxic 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).

DOI： 10.1016/j.bmcl.2017.05.060

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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 β-carboline unit. Zamamidine D (1) showed antimicrobial activity against several bacteria and fungi.

DOI： 10.1021/acs.jnatprod.6b01110

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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 cyclo-(L-Tyr1-L-Tyr2-L-Tyr3-L-Pro1-L-Pro2-L-Val-L-Pro3) 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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Twenty new neo-clerodane type diterpenoids, scutefolides G1-S (1-20), were isolated from the 70 % aqueous acetone extract of the aerial parts of Scutellaria coleifolia. Their structures were elucidated by extensive spectroscopic analyses. The absolute configurations of 1, 2, 7, 8, 14 and 15 were determined by means of the CD exciton chirality method. Compounds 1, 2, 5, 7, 8, 12, 14, 15, 18 and 19 were evaluated for their cytotoxic activities against four human cancer cell lines, and anti-bacterial activities against methicillin-resistant Staphylococcus aureus.

DOI： 10.1007/s11418-016-0967-3

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Three new acylated triterpene saponins, acernikoenosides A-C (1-3), were isolated from the stem bark of Acer nikoense, together with a known sterol glucoside. Their structures were elucidated on the basis of extensive spectroscopic analyses. This study provided the first example of triterpene saponins isolated from this plant. The anti-genotoxic activity of 1, 3 and 4 against ultraviolet irradiation was evaluated by comet assay.

DOI： 10.1248/cpb.c16-00146

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Scutefolides A1 and A2, two acylated neo-clerodanes with a 19,18-γ-lactone, scutefolides B1, B2 and C, three 19-nor-neo-clerodanes, together with scutefolides D, E1, E2 and F, four neo-clerodanes, were isolated from the EtOAc-soluble fraction of the aerial parts of Scutellaria coleifolia. Their structures were established on the basis of spectroscopic analysis. The absolute configurations of four of these compounds were elucidated by the CD exciton chirality method. Cytotoxic activities of scutefolides D-F against four cancer cell lines (KB, A549, HeLa, and MCF7) were also evaluated, but they were inactive.

DOI： 10.1016/j.phytochem.2015.05.012

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Coleifolides A and B (1 and 2), two new sesterterpenoids with a β-methyl-α,β-unsaturated-γ-lactone moiety, were isolated from the aerial parts of Scutellaria coleifolia H.Lév. (Lamiaceae), together with three known compounds. Their structures were elucidated by NMR and MS examinations. Coleifolides A and B were concluded to be partially racemic compounds by the HPLC analysis using a chiral column or introduction of chiral derivatizing agents. The absolute configuration of the major isomer was determined by analyses of the CD spectrum as well as NMR data of (R)- and (S)-2-NMA derivatives. Coleifolides A and B are structurally similar to manoalide derivatives, previously isolated from marine sponges, and appear to be the first examples of this type of compounds being isolated from higher plants.

DOI： 10.1002/cbdv.201400248

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A new secoiridoid glucoside, algiolide A (1), was isolated from the aerial parts of a Mongolian traditional herbal medicine Gentiana algida (Gentianaceae). The structure of 1 was elucidated on the basis of spectroscopic analysis and chemical conversion as well as calculations of NMR and ECD spectra. Algiolide A (1) has a novel skeleton consisting of fused α,β-unsaturated-δ-lactone and cyclopentene rings.

DOI： 10.1016/j.tetlet.2014.12.107

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INTRODUCTION: According to published information, it has not been determined whether the inhalation of cigarette smoke can induce chromosome aberrations and/or point mutations in mice, though cigarette smoke is clearly carcinogenic to mice. We tested clastogenicity of inhaled cigarette smoke in mouse by a micronucleus test using peripheral erythrocytes. Since it is important to determine the in vivo anti-genotoxic effect against inhaled cigarette smoke to reduce the risk of tobacco carcinogenesis, we also tested in vivo anti-gnotoxic effect against inhaled cigarette smoke of a Connarus extract whose in vitro anti-genotoxic effect was shown. RESULTS: Male ICR mice were exposed for 1 min to a 6-fold dilution of the smoke once a day for up to 14 consecutive days. Although the frequencies of reticulocytes with micronucleus (MNRETs) and erythrocytes with micronuclei (MN erythrocytes) did not increase within 72 h after a single inhalation of cigarette smoke, the frequency of MN erythrocytes increased significantly upon inhalation for 7 and 14 days. When the Connarus extract was fed to mice at >23.7 ppm during the inhalation period of 14 days, frequency of MN erythrocytes was significantly lower than that at 0 ppm. In vitro antioxidant activity of Connarus extract was almost same to that of vitamin C. The antioxidant activity of the Connarus extract might play an important role in its anti-genotoxic effect against cigarette smoke in vivo, like vitamins C. CONCLUSIONS: Consecutive inhalation of cigarette smoke is clastogenic to mouse bone marrow as shown by the increased frequency of MN erythrocytes. Also, it was shown the possibility that the Connarus extract reduces the risk of tobacco carcinogenesis.

DOI： 10.1186/s41021-015-0009-5

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Language：English   Publishing type：Research paper (international conference proceedings)   Publisher：GEORG THIEME VERLAG KG  

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Four new triterpenoids, indicalilacols A-D (1-4), were isolated from the MeOH extract of the fruits of Azadirachta indica, including a new 19(10→9β)abeo-tirucallane derivative, two new tirucallane-type triterpenoids, and a new euphane-type triterpenoid, along with three known tirucallane-type triterpenoids. Their structures were elucidated on the basis of spectroscopic analyses. The absolute configuration of 2 was elucidated by the chemical conversion of 2 into 21-oxo-melianodiol 24,25-acetonide. Compounds 2, 6-8 exhibited moderate cytotoxicity against three human cancer cell lines, including multidrug-resistant (MDR) cancer cells (KB-C2). Although compound 5 was not cytotoxic against any of the tested cancer cell lines, 5 showed cytotoxicity against KB-C2 cells in the presence of 2.5 μM colchicine, suggesting that 5 might have an MDR-reversal effect.

DOI： 10.1016/j.fitote.2013.11.004

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Rigenolide A (1), a new secoiridoid glucoside with a cyclobutane skeleton and three new acylated secoiridoid glucosides, 2'-(2,3-dihydroxybenzoyl)-gentiopicroside (2), 2'-(2,3-dihydroxybenzoyl)-swertiamarin (3), 3'-(2,3-dihydroxybenzoyl)-sweroside (4), along with two noriridoids (7 and 8) and two known secoiridoid glucosides (5 and 6), were isolated from Gentiana rigescens Franch. The structures of new compounds were elucidated by extensive spectroscopic analyses. The isolated compounds were evaluated for DPPH free-radical scavenging activity.

DOI： 10.1016/j.fitote.2013.08.006

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Secoiridoid glucosides, including two conjugates with a phenolic and two conjugates with a nicotinic acid derivative (3 and 4), together with seven known secoiridoid derivatives, were isolated from flower buds of Lonicera japonica. The structures were elucidated by spectroscopic analyses. Anti-influenza activities of six isolated compounds were also evaluated by plaque assay and neuraminidase inhibitory assay.

DOI： 10.1016/j.phytochem.2013.09.021

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Five new eudesmane- (1-5), two new guaiane- (6 and 7) and one new germacrane-type (8) sesquiterpene lactone glucosides were isolated from the H2O-soluble fraction of the roots of Ferula varia. Their structures were elucidated by extensive spectroscopic analyses. The absolute configuration of 1 was determined by modified Mosher's method. © 2012 Phytochemical Society of Europe.

DOI： 10.1016/j.phytol.2012.08.001

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Two new caffeoyl quinic acid α-glucosides, together with three known caffeoyl quinic acids and five known flavonoid glucosides, were isolated from the leaves of Moringa oleifera Lam. The structures of the new compounds were elucidated as 4-O-(4'-O-α-D-glucopyranosyl)-caffeoyl quinic acid (1) and 4-O-(3'-O-α-D-glucopyranosyl)-caffeoyl quinic acid (2) by spectroscopic analyses.

DOI： 10.1007/s11418-011-0563-5

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Seven new sesquiterpene lactone glycosides (1-7) were isolated from the H2O-soluble fraction from the MeOH extract of the roots of Ferula varia. Their structures were elucidated by extensive spectroscopic analyses. The absolute configurations of compounds 1 and 2 were determined by modified Mosher's method.

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Six triterpenes and a triterpene glucoside were isolated from the MeOH extract of the leaves of Dysoxylum cumingianum together with three known triterpenes. Their structures were elucidated by extensive spectroscopic analyses. In cytotoxicity assays against three human cancer cell lines, including a multi-drug resistant cancer cell line (KB-C2), compounds 1, 2 and 5 demonstrated significantly enhanced cytotoxicity against KB-C2 cells in the presence of 2.5 μM colchicine, as compared with those in the absence of colchicine. This result suggested that these triterpenes might show some MDR-reversing effects.

DOI： 10.1016/j.phytochem.2011.08.002

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Eight new triterpenoids, including sinocalycanchinensins A-E (1-5) with a 3,4-seco-29-nor-cycloartane skeleton, sinocalycanchinensin F (6) possessing a novel 2,3-seco-29-nor-cycloartane skeleton, and 29-nor-cycloartanes, sinocalycanchinensins G and H (7 and 8), have been isolated from the leaves of Sinocalycanthus chinensis. Their structures were elucidated on the basis of spectroscopic examinations. The cytotoxicities of the isolated new triterpenes against a panel of human cancer cell lines, including multi-drug resistant (MDR) cancer cell lines, were also evaluated. Compound 5 demonstrated enhanced cytotoxicity against MDR KB cells in the presence of colchicine, although all the compounds showed moderate or no cytotoxicities.

DOI： 10.1016/j.bmc.2011.03.055

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As part of our chemical studies on the medical plants in Uzbekistan aimed at searching for new drug leads, we have examined the aerial parts of Mediasia macrophylla. This has resulted in the isolation of four new glucosides, together with 30 known compounds. The structures of new compounds were elucidated as (1'S)-(4-hydroxyphenyl) ethane-1',2'-diol 2'-O-β-glucopyranoside (1), 3-(4'-methoxyphenyl)-propanol 1-O-β-glucopyranoside (2), 2-methoxy-3-hydroxy-5-(E)-propenyl-phenol 1-O-β-glucopyranoside (3), 1-O-angeloyl-β-glucopyranose (4), on the basis of spectral analysis.

DOI： 10.1007/s11418-010-0444-3

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A new aurone glucoside (1) and three new biflavonoids (12 - 14), together with fourteen known compounds, were isolated from the flowers of Butea monosperma (Lam.) Taub. The structures of the new compounds were established by 1D, 2D NMR, MS and CD analyses. The isolated compounds were evaluated for their influenza A neuraminidase inhibitory activity and DPPH free-radical scavenging activity. © 2011 The Japan Institute of Heterocyclic Chemistry.

DOI： 10.3987/COM-11-12275

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Three new steroids dyscusins A-C (1-3), including a stigmastane-type sterol and two pregnanes, together with two known steroids were isolated from the leaves of Dysoxylum cumingianum (Meliaceae). Their structures were elucidated on the basis of extensive spectroscopic analyses. In a cytotoxicity assay, compound 1 showed ten-fold enhanced cytotoxicity against multi-drug resistant cancer cells (KB-C2) in the presence of 2.5 µM colchicine as compared with the absence of colchicine. This notable finding indicated that 1 possessed a multi-drug resistant reversal effect.

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Polyacetylenic glucosides (1-5) were isolated from the MeOH extract of Mediasia macrophylla, and their structures were established by spectroscopic analyses. Compounds 2-4 were the first examples of C(10)-polyacetylenic glucosides found in the family Umbelliferae, while compound 1 was a unique polyacetylenic glucoside possessing an alpha-pyrone moiety.

DOI： 10.1016/j.phytochem.2009.12.007

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