研究者詳細 - 清田　洋正

論文 - 清田　洋正

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P-60 サリチルアルデヒド型イネいもち病菌毒素の合成化学的研究(ポスター発表の部)

清田洋正, 佐々木郁香, 田中功二, 中村葉子, 上田留美, 鈴木雄二, 桑原重文, 貫名学

天然有機化合物討論会講演要旨集 ( 53 ) 661 - 666 2011年9月

記述言語：日本語出版者・発行元：天然有機化合物討論会

Rice blast disease, caused by infection of rice blast fungus Magnaporthe grisea (Hebert) Barr. (perfect stage of Pyricularia oryzae Cabara), has been the most serious pest for rice. The fungus mainly produces several phytotoxic compounds according to fermentation method, i. e., dihydropyriculol (1), pyriculol (2), and pyriculone (3) by a shaking culture; dihydropyriculariol (5) and pyriculariol (6) by an aeration and agitation culture; and tenuazonic acid by a stationary culture in a soy sauce-sucrose medium. Pyricuol (4) together with 2 were produced by a shaking culture with a potato dextrose medium. These salicylaldehyde-type phytotoxins are common metabolites of blast fungi of various host plants except a ginger. To develop novel methods to control the blast disease a better knowledge of the biosynthesis is necessary. Synthesis of both enantiomers of pyricuol (4) from (R)- and (8-lactates was achieved using [2,31-Wittig rearrangement and Stille coupling reactions as the key steps. This revealed that the natural 4 has an R-configuration. Racemic synthesis is also reported. On the other hand, optically active pyriculariol (6) was synthesized from L-rhamnose using microwave assisted Stille coupling reaction of the unprotected substrates as the key step. A comparison of the CD spectra and 1H NMR spectra of the corresponding MTPA esters found that natural pyriculariol (6) existed as a racemate. Biotransformation of the plausible biosynthetic intermediates 7-d2 and 8-d in deuterio forms was also examined. Not diol 7-d2 but aldehyde 8-d was converted by the fungus M. grisea into dihydropyriculariol (1-d) in soy sauce-sucrose medium under a shaking culture. Foliar application test of the synthetic compounds on rice leaves revealed that both a salicylaldehyde and a side chain fragments are necessary for the necrotic activity. In conclusion, the blast fungus M. grisea produced 1, 2, and 4 in optically active forms and 5 and 6 as racemates depending on the culture conditions. Additionally, it is interesting that both oxidation and reduction would be coexist at the later stage of biosynthesis of these phytotoxins.

DOI： 10.24496/tennenyuki.53.0_661

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Biotransformation of a biosynthetic intermediate mimic of nonactin by Streptomyces griseus

Tadaatsu Hanadate, Kentaro Takai, Naoki Abe, Teiko Yamada, Shigefumi Kuwahara, Hiromasa Kiyota

HETEROCYCLIC COMMUNICATIONS 17 ( 3-4 ) 93 - 98 2011年9月

記述言語：英語掲載種別：研究論文（学術雑誌）出版者・発行元：WALTER DE GRUYTER GMBH

A mimic of a plausible biosynthetic intermediate of bishomononactic acid, one of the monomers of macrotetrolide antibiotics (polynactin), was synthesized as a thiol ester. FAB-MS analysis showed that fermentation of polynactin producing Streptomyces griseus with the compound, afforded the unnatural polynactins containing bishomononactic acid(s).

DOI： 10.1515/HC.2011.021

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Synthesis of macrotetrolide alpha, a designed polynactin analog composed of bishomononactic acids

Kentaro Takai, Tadaatsu Hanadate, Masaki Abe, Yukie Ono, Teiko Yamada, Shigefumi Kuwahara, Hiromasa Kiyota

TETRAHEDRON 67 ( 37 ) 7066 - 7072 2011年9月

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

Macrotetrolide alpha (1), a designed polynactin analog composed of (+)- and (-)-bishomononactic acids, was synthesized. The monomeric acids were prepared using cis-selective iodoetherification and optical resolution of the corresponding O-acetylmandelates as the key steps. Esterification and macrolactonization of the monomers were performed by Corey-Mukaiyama-Gerlach method. Compound 1 showed no immunosuppressive activity contrary to other natural polynactin congeners. (C) 2011 Elsevier Ltd. All rights reserved.

DOI： 10.1016/j.tet.2011.07.012

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Novel metabolic pathways of organochlorine pesticides dieldrin and aldrin by the white rot fungi of the genus Phlebia

Pengfei Xiao, Toshio Mori, Ichiro Kamei, Hiromasa Kiyota, Kazuhiro Takagi, Ryuichiro Kondo

CHEMOSPHERE 85 ( 2 ) 218 - 224 2011年9月

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

White rot fungi can degrade a wide spectrum of recalcitrant organic pollutants, including polychlorinated dibenzo-p-dioxins (PCDDs) and polychlorinated biphenyls (PCBs). In this experiment, 20 white rot fungi, belonging to genus Phlebia, were investigated for their ability to degrade dieldrin. Based on the screening results, we further investigated Phlebia acanthocystis, Phiebia brevispora, and Phlebia aurea to determine their degradation capacity and metabolic products towards dieldrin and aldrin. The three fungi were able to remove over 50% of dieldrin in a low nitrogen medium, after 42 d of incubation. Three hydroxylated products were detected as metabolites of dieldrin, suggesting that in Phlebia strains, hydroxylation reactions might play an important role in the metabolism of dieldrin. In contrast to dieldrin, aldrin exhibited higher levels of degradation activity. Over 90% of aldrin was removed after 28 d of incubation, and several new metabolites of aldrin in microorganisms, including 9-hydroxyaldrin and two carboxylic acid products, were detected in fungal cultures. These results indicate that the methylene moiety of aldrin and dieldrin molecules might be prone to enzymatic attack by white rot fungi. In this study, we describe for the first time a new metabolic pathway of both compounds by fungi of genus Phlebia. (C) 2011 Elsevier Ltd. All rights reserved.

DOI： 10.1016/j.chemosphere.2011.06.028

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Novel Taxa-4(20),12-diene and 2(3 -> 20)Abeotaxane from Needles of Taxus canadensis

Zhi-Yu Ni, Yi-Bing Wu, Man-Li Zhang, Yu-Fang Wang, Mei Dong, Francoise Sauriol, Chang-Hong Huo, Qing-Wen Shi, Yu-Cheng Gu, Hiromasa Kiyota, Bin Cong

BIOSCIENCE BIOTECHNOLOGY AND BIOCHEMISTRY 75 ( 9 ) 1698 - 1701 2011年9月

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

A novel 6/8/6-membered taxane with a rare C-12(13)-double bond and rare 2(3 -> 20)abeotaxane were isolated from the needles of Taxus canadensis. Their structures were characterized as 7 beta,9 alpha,10 beta-triacetoxy-taxa-4(20),12-diene-2 alpha,5 alpha,11 beta-triol (1) and 2 alpha,7 beta,10 beta-triacetoxy-5 alpha-hydroxy-2 (3 -> 20)abeotaxa-4(20),11-diene-9,13-dione (2) on the basis of 1D and 2D spectroscopic data. 1 is the first example of a natural taxane without substitution at both C-13 and C-14.

DOI： 10.1271/bbb.110223

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Achillinin A, a Cytotoxic Guaianolide from the Flower of Yarrow, Achillea millefolium

Yong Li, Man-Li Zhang, Bin Cong, Si-Ming Wang,Mei Dong, Fran?oise Sauriol, Chang-Hong Huo,Qing-Wen Shi, Yu-Cheng Gu, Hiromasa Kiyota*

Biosci. Biotechnol. Biochem. 75 ( 8 ) 1554 - 1556 2011年8月

Chemical and Pharmacological Research of the Plants of Genus Caesalpinia

Yan Yanga, Lei Zhaoa, Changhong Huoa, Yucheng Gua, Qingwen Shi, Hiromasa Kiyota*

Chemistry and Biodiversity 8 ( 8 ) 1370 - 1399 2011年8月

Isolation and identification of dieldrin-degrading Pseudonocardia sp strain KSF27 using a soil-charcoal perfusion method with aldrin trans-diol as a structural analog of dieldrin

Futa Sakakibara, Kazuhiro Takagi, Ryota Kataoka, Hiromasa Kiyota, Yuuki Sato, Sanae Okada

BIOCHEMICAL AND BIOPHYSICAL RESEARCH COMMUNICATIONS 411 ( 1 ) 76 - 81 2011年7月

記述言語：英語掲載種別：研究論文（学術雑誌）出版者・発行元：ACADEMIC PRESS INC ELSEVIER SCIENCE

We isolated a novel aerobic dieldrin-degrading bacterium from an enrichment culture in a soil-charcoal perfusion system. Enrichment culture using a soil-charcoal perfusion system was an effective way to obtain microorganisms that degrade recalcitrant compounds. The soil-charcoal perfusion was performed using aldrin trans-diol, which was a metabolite of dieldrin. Aldrin trans-diol had higher bioavailability (2.5 mg/l) than dieldrin (0.1-0.25 mg/l), therefore it is possible for microorganisms to utilize it as a substrate in soil. After 100 days of circulation and three exchanges of the medium, the enriched charcoal was harvested and a bacterium isolated. The isolate was designated as strain KSF27 and was found to be closely related to Pseudonocardia spp. as determined by 16S rRNA sequencing analysis. Strain KSF27 degraded aldrin trans-diol by 0.05 mu mol/l from an initial concentration of 25.5 mu mol/l. The metabolite of aldrin trans-diol was detected by HPLC/MS and determined to be aldrindicarboxylic acid based on retention time and the MS fragment. Moreover, strain KSF27 degraded dieldrin from 14.06 mu mol/l to 2.01 mu mol/l over a 10-day incubation at 30 degrees C. This strain degraded dieldrin and other persistent organo-chlorine pesticides, such as alpha-endosulfan, beta-endosulfan, endosulfan sulfate, heptachlor, heptachlor epoxide and chlordecone. (C) 2011 Elsevier Inc. All rights reserved.

DOI： 10.1016/j.bbrc.2011.06.096

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A Novel Taxatetraene Framework Formed From a New Natural Taxane from Taxus cuspidata

Yong Li, Yong-Li Wang, Zhi-Yu Ni, Mei Dong, Bin Cong, Francoise Sauriol, Man-Li Zhang, Yu-Fang Wang, Chang-Hong Huo, Yu-Cheng Gu, Qing-Wen Shi, Hiromasa Kiyota

ZEITSCHRIFT FUR NATURFORSCHUNG SECTION B-A JOURNAL OF CHEMICAL SCIENCES 66 ( 7 ) 759 - 761 2011年7月

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

Sinenxan H [2 alpha,14 beta-diacetoxytaxa-4(20),11-diene-5 alpha, 10 beta-diol, 1] was isolated from the heartwood of Taxus cuspidata, for the first time from natural sources. Compound 1 was found to be readily converted into 2 alpha-acetoxytaxa-4(20),10,12(18),13-tetraen-5 alpha-ol (2), the first example of a taxane with 10,11- and/or 13,14-double bond(s) and a conjugated triene system, in CDCl(3).

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The First Taxane peroxide from the Rooted Cuttings of Taxus canadensis

Zhen-Hua Pan, Man-Li Zhang, Yu-Fang Wang, Mei Dong, Chang-Hong Huo, Fran?oise Sauriol, Qing-Wen Shi, Hiromasa Kiyota*, Yong-Jian Zhang

Heterocyclic Communications 17 ( 1-2 ) 87 - 91 2011年7月

Stereochemistry of enacyloxins 6. Synthesis of a C16'-C17' fragment of Enacyloxins, A Series of Antibiotics from Frateuria sp. W-315

Wataru Igarashi, Hiroaki Hoshikawa, Hiroyuki Furukawa, Teiko Yamada, Shigefumi Kuwahara, and Hiromasa Kiyota*

Heterocyclic Communications 17 ( 1-2 ) 7 - 9 2011年7月

Stereochemistry of enacyloxins. Part 5: Synthesis of a C9 '-C15 ' fragment of enacyloxins, a series of antibiotics from Frateuria sp W-315

Hiroyuki Furukawa, Hiroaki Hoshikawa, Wataru Igarashi, Manabu Yaosaka, Teiko Yamada, Shigefumi Kuwahara, Hiromasa Kiyota

HETEROCYCLIC COMMUNICATIONS 17 ( 1-2 ) 3 - 5 2011年7月

Improved Method for Antinematodal Assay by Using Extraction Thimble and Antinematodal Activity of 4-Methylumbelliferyl Glycosides Synthesized by Mitsunobu Reaction 査読

Nematological Research 51 ( 2 ) 33 - 36 2011年3月

A Novel Taxane 13-Glucoside and Other Taxanes from the Leaves of Taxus cuspidata

Zhi-Yu Ni, Mei Dong, Bin Cong, Francoise Sauriol, Man-Li Zhang, Yu-Fang Wang, Chang-Hong Huo, Qing-Wen Shi, Hiromasa Kiyota

PLANTA MEDICA 77 ( 3 ) 281 - 283 2011年2月

記述言語：英語掲載種別：研究論文（学術雑誌）出版者・発行元：GEORG THIEME VERLAG KG

Three new taxanes, 2 alpha, 9 alpha, 10 beta-triacetoxy-13 alpha-(beta-D-glucopyranosyloxy)taxa-4(20), 11-dien-5 alpha-ol (1), 5 alpha, 10 beta, 13 alpha-triacetoxytax-11-ene-2 alpha,7 beta,9 alpha,20-tetraol (2), and 5 alpha, 10 beta, 13 beta-triacetoxy-2 alpha, 7 beta-dihydroxy-2(3 -> 20)abeotaxa-4(20), 11-dien-9-one (3), were isolated from the leaves of the Japanese yew, Taxus cuspidata. Compound 1 is the first example of a taxane with 13-glycosidic linkage.

DOI： 10.1055/s-0030-1250333

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Oxepinamides: Novel Liver X Receptor Agonists from Aspergillus puniceus

Xin-Hua Lu, Qing-Wen Shi, Zhi-Hui Zheng, Ai-Bing Ke, Hua Zhang, Chang-Hong Huo, Ying Ma, Xiao Ren, Ye-Ying Li, Jie Lin, Qin Jiang, Yu-Cheng Gu, Hiromasa Kiyota

EUROPEAN JOURNAL OF ORGANIC CHEMISTRY ( 4 ) 802 - 807 2011年2月

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-BLACKWELL

Four novel oxepin-containing pyrimidines, namely oxepinamides D-G (1-4), were isolated from cultures of Aspergillus puniceus F02Z-1744. The structures of 1-4 were elucidated by analyzing their spectroscopic data generated by 1D and 2D NMR and MS methods. The configurations of 1 and 2 were established based on single-crystal X-ray crystallographic analysis. All four compounds 1-4 showed transcriptional activation on Liver X Receptor alpha (LXR alpha) with EC(50) values of 10.6, 12.8, 13.6, and 12.1 mu M, respectively.

DOI： 10.1002/ejoc.201000812

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Chemical and Pharmacological Research of the Plants of Genus Senecio

Yan Yang, Lei Zhao, Yu-Fang Wang, Man-Li Chang, Chang-Hong Huo, Yu-Cheng Gu, Qing-Wen Shi, Hiromasa Kiyota*

Chemistry and Biodiversity 8 ( 1 ) 13 - 72 2011年

Two New Phytoecdysteroids from the Needles of Taxus canadensis

Yu Fang, Zhi-Yu Ni, Teiko Yamada, Yu-Fang Wang, Man-Li Zhang, Mei Dong, Bin Cong, Francoise Sauriol, Chang-Hong Huo, Qing-Wen Shi, Hiromasa Kiyota

ZEITSCHRIFT FUR NATURFORSCHUNG SECTION B-A JOURNAL OF CHEMICAL SCIENCES 65 ( 11 ) 1401 - 1405 2010年11月

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

Two new phytoecdysteroids with a 20,22-acetal group were identified for the first time from the needles of the Canadian yew, Taws canadensis. Their structures were characterized as ponasterone A 20,22-p-hydroxybenzylidene acetal (1) and ponasterone A 20,22-acetonide (2) on the basis of 1D, 2D NMR evidence and high-resolution FABMS analysis.

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Biodegradation of Dieldrin by a Soil Fungus Isolated from a Soil with Annual Endosulfan Applications

Ryota Kataoka, Kazuhiro Takagi, Ichiro Kamei, Hiromasa Kiyota, Yuuki Sato

ENVIRONMENTAL SCIENCE & TECHNOLOGY 44 ( 16 ) 6343 - 6349 2010年8月

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

An aerobic dieldrin-degrading fungus, Mucor racemosus strain DDF, was isolated from a soil to which endosulfan had been annually applied for more than 10 years until 2008 Strain DDF degraded dieldrin to 1 01 mu M from 143 mu M during a 10-day incubation at 25 degrees C Approximately 0 15 mu M (9%) of aldrin transdiol was generated from the dieldrin degradation after a 1-day incubation The degradation of dieldrin by strain DDF was detected over a broad range of pH and concentrations of glucose and nitrogen sources. Extracellular fluid without mycelia also degraded dieldrin Strain DDF degraded not only dieldrin but also heptachlor, heptachlor epoxide, endosulfan, endosulfan sulfate, DDT, and ODE Endosulfan sulfate and heptachlor were degraded by 0.64 mu M (95%) and 0.75 mu M (94%), respectively, whereas endosulfan and DDE were degraded by 2 42 mu M (80%) and 3 29 mu M (79%), respectively, and DDT and heptachlor epoxide were degraded by 695 mu M (49 3%) and 5 36 mu M (67 5%), respectively, compared with the control, which had a concentration of approximately 14 mu M. These results suggest that strain DDF could be a candidate for the bioremediation of sites contaminated with various persistent organochlorine pesticides including POPs

DOI： 10.1021/es1000227

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Chemical Constituents of Plants from Genus Valeriana

Yu-Fang Wang, Li-Qing Jin, Chang-Hong Huo, Qing-Wen Shi, Yu-Cheng Gu, Hiromasa Kiyota*

Mini-Reviews in Organic Chemistry 7 ( 2 ) 161 - 172 2010年5月

Xylocarponoids A and B, Unique C28 Skeleton Limonoids from Xylocarpus granatum

Chang-Hong Huo, Dong Guo, Li-Ru Shen, Bao-Wei Yin, Fran?oise Sauriol, Li-Geng Li, Man-Li Zhang, Qing-Wen Shi, Hiromasa Kiyota*

Tetrahedron Letters 51 ( 4 ) 754 - 757 2010年1月

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