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Biochemical Studies on Relationships between Plant Fungitoxins and Phytopathogens

植物真菌毒素与植物病原体关系的生化研究

基本信息

批准号：
61560130
负责人：
TAHARA Satoshi
金额：
$ 1.15万
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：
1986
资助国家：
日本
起止时间：
1986 至 1987
项目状态：
已结题

项目摘要

As the results of the present study on constitutive isoflavonoids in lupins (Lupinus albus and L. luteus) were found to contain numerous simple and complex isoflavones and coumaronochromones, many of which were fungitoxic. The structural variation in the lupin isoflavonoids are due to the following five factors:1) basic structure (4 kinds of simple isoflavonoids)2) prenyl (=3,3-dimethylallyl) substitution at 6 and/or 3'(L. albus) and at 6 or 8 (L. luteus)3) modification of the prenyl sidechain (hydration, terminal hydroxylation and transformation to 2-hydroxy-3-methyl-3-butenyl group)4) ring formation (dihydrofurano-, dihydropyrano- and pyrano-fused A- and/or B-ring5) 5-O-methylation (L. luteus)It has long been recognized that some fungi have the ability to metabolise and detoxify isoflavonoids, and in certain cases this process seems to be closely linked with pathogenicity. Botrytis cinerea was found to convert prenylated isoflavones into various dihydrofurano- and dihydropyrano-isoflavones, and glycols, all of which might arise via epoxidation of the unsaturated sidechain in the appropriate substrate. The substrate specificity of the fungal metabolism yielding those polar compounds with greatly decreased fungitoxicity and stereochemistry in the metabolism of an achiral isoflavone to a chiral one been elucidated.A further experiment was conducted to confirm the presence of an epoxide as a metabolic intermediate from a prenylated isoflavone to cyclic ether and glycol derivatives. The expected epoxide was successfully detected by using B. cinerea and 5,2',4'-trihydroxy-7 methoxy-8-prenylisoflavone as a substrate.The fate of 5,7,2',4'-tetrahydroxy-6-prenylisoflavone (luteone) in rat liver homogenates was also examined from the interest in comparative biochemistry of the prenylated isoflavone metabolism.

本文对羽扇豆（Lupinus albus和L. luteus）含有许多简单和复杂的异黄酮和香豆色酮，其中许多是真菌毒素。羽扇豆内酯的结构变异主要由以下5个因素引起：1）基本结构（4种简单内酯）; 2）6位和/或3 '位（L. albus）和6或8（L. luteus）3）异戊二烯侧链的修饰（水合、末端羟基化和转化为2-羟基-3-甲基-3-丁烯基）4）环形成（二氢呋喃并-、二氢吡喃并-和吡喃并-稠合的A-和/或B-环5）5-O-甲基化（L. luteus）长期以来，人们认识到一些真菌具有代谢和解毒真菌的能力，在某些情况下，这一过程似乎与致病性密切相关。发现灰葡萄孢菌将异戊二烯化的异戊烯酮转化为各种二氢呋喃并-和二氢吡喃并-异戊烯酮和二醇，所有这些都可能通过在适当的底物中不饱和侧链的环氧化而产生。通过实验进一步证实了环氧化物作为异戊二烯化的异戊二烯衍生物生成环醚和乙二醇衍生物的代谢中间体的存在。通过使用B成功地检测到预期的环氧化物。从异戊烯化的异戊烯代谢的比较生物化学的兴趣，还检查了5，7，2 ′，4 ′-四羟基-6-异戊烯基异黄酮（叶黄素）在大鼠肝匀浆中的命运。