Studies on Fungal Metabolism of Phytoalexins

植物抗毒素的真菌代谢研究

• 批准号: 63560116
• 负责人: TAHARA Satoshi
• 金额: $ 1.34万
• 依托单位: Hokkaido University
• 依托单位国家: 日本
• 项目类别: Grant-in-Aid for General Scientific Research (C)
• 财政年份: 1988
• 资助国家: 日本
• 起止时间: 1988 至 1989
• 项目状态: 已结题
• 来源: https://kaken.nii.ac.jp/grant/KAKENHI-PROJECT-63560116/
• 关键词: Phytoalexin; Fungal Metabolism; Antifungal Compound; Prenylated Isoflavone; Isoflavonoid; Leguminosae; Botrytis cinerea; Epoxy-intermediate; ファイトアレキシンの代謝; プレニルイソフラボン; 微生物代謝; 植物由来抗菌物質; 解毒代謝; 防御物質

Fungal metabolism of phytoalexins was investigated by using prenylated isoflavones and related compounds as substrates, and Botrytis cinerea and Aspergillus flavus. Research results are summarized as follows. (1) 7-O-Methyl-luteone (1) and 7-O-Methyl-2,3-dehydrokievitone (2) both chemically derivated from the corresponding isoflavones, topazolin (3) isolated from Lupinus luteus and piscidone from the root barks of Piscidia erythrina were metabolized by two fungi. A 6-prenylated flavone 3 was metabolized as 6-prenylated isoflavone had been. The prenyl group at C-6' in 4 was successfully transformed into the corresponding cyclic ether by B. cinerea. (2) The major metabolite from 1 was confirmed to be 2,2-dimethyl-3-hydroxypyranoisoflavone with dextrorotatory nature. The stereochemistry was estimated to be S-configuration. (3) Compound 2 was rapidly metabolized not by A. flavus, but by B. cinerea to yield an epoxy-derivative at the double bond in the prenyl side chain and a glycol. The latter metabolite revealed to be S-isomer with which the acid hydrolyzate (stereo-retention) of the epoxide agreed well. Therefore the configuration of the epoxy-intermediate was confirmed to be S. The presence of an epoxy-intermediate in the metabolism of a prenylated compound into a dihydrofurano- or dihydropyrano-cyclic ether and/or a 2,3-dihydrodihydroxy- prenyl derivative was thus confirmed for the first time.Isoflavonoidal constituents in white lupin (L. albus) were precisely examined and the structures of complex lupin isoflavones suggested that they were presumably produced from prenylated isoflavones via epoxy-intermediates. The biogenedis for lupin isoflavones was thus closely related to their fungal metabolism.

以戊酰化异黄酮及其相关化合物为底物，以灰葡萄孢菌和黄曲霉为底物，研究了植物抗毒素的真菌代谢。研究结果总结如下：(1) 7-O-Methyl-luteone(1)和7- o - methyl -2,3-dehydrokievitone(2)均由相应的异黄酮化学衍生，从Lupinus luteus中分离的topazolin(3)和从pcidia erythrina根皮中分离的piscidone被两种真菌代谢。6-戊烯基化黄酮3被代谢为6-戊烯基化异黄酮。B. cinerea成功地将C-6′上的戊烯基转化为相应的环醚。(2) 1的主要代谢产物为2,2-二甲基-3-羟基异黄酮，具有右旋性质。立体化学估计为s构型。(3)化合物2不是被黄芽孢杆菌代谢，而是被灰芽孢杆菌代谢，在丙烯基侧链的双键处生成一个环氧衍生物和一个乙二醇。后一种代谢物显示为s -异构体，与环氧化物的酸水解产物（立体保留）一致。因此，证实了环氧中间体的构型为s。首次证实了环氧中间体在戊烯基化化合物代谢成二氢呋喃或二氢吡喃环醚和/或2,3-二氢二羟基戊烯基衍生物中的存在。对白罗苹（L. albus）中的异黄酮成分进行了精确的检测，其结构表明它们可能是由环氧中间体经戊酰化异黄酮合成的。因此，罗苹异黄酮的生物成因与其真菌代谢密切相关。

项目成果

田原哲士,吉原照彦,朝日田康司ら編(分担執筆): "生物生産効率の向上に関する研究" 北海道大学農学部, 27 (1988)

田原哲志、吉原照彦、旭田浩二等（共同作者）：《提高生物生产效率的研究》北海道大学农学部，27（1988）

S.Tahara,J.L.Ingham and J.Mizutani: "Indentification of an Epoxy-intermediate Resulting from the Fungal Metabolism of a Prenylated Isoflavone" Phytochemistry. 28. 2079-2084 (1989)

S.Tahara、J.L.Ingham 和 J.Mizutani：“异戊二烯化异黄酮真菌代谢产生的环氧中间体的鉴定”植物化学。

S.Tahara,F.Hanawa,Y.Harada and J.Mizutani: "A Fungitoxin Inducibly Produced by Dandelion Leaves Treated with Cupric Chloride" Agric.Biol.Chem.52. 2947-2948 (1988)

S.Tahara、F.Hanawa、Y.Harada 和 J.Mizutani：“氯化铜处理蒲公英叶诱导产生的真菌毒素”Agric.Biol.Chem.52。

S. Tahara and T. Yoshihara (a part): "Studies on the Improvement of Bio-production, ed, by K. Asahida et al., Faculty of Agriculture, Hokkaido University" pp. 80-106, 1988.

S. Tahara 和 T. Yoshihara（部分）：“生物生产改进研究，K. Asahida 等编辑，北海道大学农学院”，第 80-106 页，1988 年。

S.Tahara,E.Narita J.Mizutani and J.L.Ingham: "New Rotenoids from the Root Bark of Jamaican Dogwood(Piscidia erythrina L.)" Z.Naturforsch.,No.3-4. 45C. (1990)

S.Tahara、E.Narita J.Mizutani 和 J.L.Ingham：“来自牙买加山茱萸 (Piscidia erythrina L.) 根皮的新鱼藤素”Z.Naturforsch.，No.3-4。