Studies on the Interaction between Plant Secondary Metabolites and Xenobiotics

植物次生代谢产物与外源物质相互作用的研究

• 批准号: 02454064
• 负责人: TAHARA Satoshi
• 金额: $ 3.78万
• 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 (B)
• 财政年份: 1990
• 资助国家: 日本
• 起止时间: 1990 至 1992
• 项目状态: 已结题
• 来源: https://kaken.nii.ac.jp/en/grant/KAKENHI-PROJECT-02454064/
• 关键词: benomyl; carbendazim; benzimidazole fungicide; polyphenol; tubulin; emodin; antidote; flavonoid; ベンズイミダゾ-ル殺菌剤; 解毒剤; βーチュ-ブリン; タデ科植物; 植物二次代謝産物; スチルベン誘導体; フラボン類; 生体異物; 抗菌性物質; ポリフェノ-ル; 相互作用

Biological and chemical studies on the interaction between plant seconda secondary metabolites and xenobiotics were conducted to reveal the potency of protective facilities of higher plants. 1. At first the plant secondary metabolites which exhibited antidoting activity against benzimidazole fungicides were surveyed and the following five compounds all from Polygonaceae were recognized as anti-MBC (=carbendazim, an active principle of benomyl and thiophanate-methyl both benzimidazole type fungicides) substances, and identified their chemical structures: emodin (1) and alpha-tocopherol(2)from Polygonum sachalinense; 5-methoxy-6,7-methylene-dioxyflavone (3) and 3,5-dihydroxy-4-methylstilbene (4) from P. nodosum; and 2,6-dimethoxy-1,4-benzoquinone (5) from P. thunbergii. 2. Structure-activity relationships between the antidoting activity against MBC and quinones (anthra- and naphtho-quinones) or flavones were analyzed. The most active compounds were lapachol (3-hydroxy-4-prenylnaphthoquinone) in quinones and unsubstituted flavone or 5-methoxyflavone in flavonoids. 3. The mode of action of the antidoting agent against MBC which is believed to be an inhibitor of tubulin polymerization and consequently resulting in a failure of mitosis, was very much interested. So far as we know at present is that the antidotes mentioned above do not compete with MBC for the binding site of beta-tubulin in vitro. 4. Some physiologically active secondary metabolites, isoflavonoids, sesquiterpene derivatives and oligostilbenes were isolated and elucidated their structures respectively, from Piscidia erythrina (Leguminosae); Rosa rugosa (Rosaceae) and Chloranthus Japonicus and C. serratus (Chloranthaceae); and Carex spp. (Cypreaceae).

为了揭示植物保护设施的效能，对植物次生代谢产物与外源物质的相互作用进行了生物学和化学研究。1.首先对苯并咪唑类杀菌剂的植物次生代谢产物进行了筛选，确定了以下五个化合物具有抗多菌灵活性（=苯菌灵和甲基硫菌灵的有效成分）物质，并鉴定了它们的化学结构：大黄素（1）和α-生育酚（2），分别来源于高山蓼（Polygonum sachalinense）; 5-甲氧基-6，7-亚甲基二氧基黄酮（3）和3，5-二羟基-4-甲基二苯乙烯（4）; 2.分析了对MBC的解毒活性与醌类（蒽醌和萘醌）或黄酮类之间的构效关系。醌类中活性最高的化合物为拉帕酚（3-羟基-4-异戊二烯基萘醌），黄酮类中活性最高的化合物为未取代黄酮或5-甲氧基黄酮。3. MBC被认为是微管蛋白聚合的抑制剂，因此导致有丝分裂的失败，解毒剂对MBC的作用模式非常感兴趣。目前我们所知的是，上述解毒剂在体外不与MBC竞争β-微管蛋白的结合位点。4.从刺桐花、玫瑰、金粟兰和金粟兰中分离鉴定了具有生理活性的次生代谢产物--异黄酮、倍半萜衍生物和低聚芪类化合物，并分别鉴定了它们的结构。serratus（金粟兰科（Chloranthaceae））;和苔草属（Carex spp.）（Cypreaceae）。

项目成果

M. Moriyama, S. Tahara, J. L. Ingham and J. Mizutani: "Isoflavonoid Alkaloids from Piscidia erythrina" Phytochemistry.

M. Moriyama、S. Tahara、J. L. Ingham 和 J. Mizutani：“来自赤藻的异黄酮生物碱”植物化学。

S.Tahara,M.Moriyama,J.L Ingham and J.Mizutani: "5,7,3',4',5'-Pentaoxygenated and 2',6'-Dipernylted Isoflacones from Piscidia erythrina" Phytochemistry. 30. 2769-2775 (1991)

S.Tahara、M.Moriyama、J.L Ingham 和 J.Mizutani：“来自 Piscidia erythrina 的 5,7,3,4,5-五氧化和 2,6-二哌酰异黄酮”植物化学。

S.Tahara,M.Moriyama,J.L.Ingham and J.Mizutani: "Structure Revision of Piscidone,a MaJor Igoflavonoid in the Root Bark of Piscidia erythrina" Phytochemistry. 31. 679-682 (1992)

S.Tahara，M.Moriyama，J.L.Ingham 和 J.Mizutani：“Piscidone 的结构修订，Piscidone 是 Piscidia erythrina 根皮中的一种主要 Igoflavonoid”植物化学。

Satoshi TAHARA: "Structure Revision of Piscidone,a Major Isoflavonoid in the Root Bark of Piscidia erythrina" Phytochemistry. 31. 679-682 (1992)

Satoshi TAHARA：“Piscidone（Piscidia erythrina 根皮中的一种主要异黄酮类化合物）的结构修正”植物化学。

S. Tahara, M. Moriyama, J. L. Ingham and J. Mizutani: "Diverse Oxygenated Isoflavonoids from Piscidia erythrina" Phytochemistry.

S. Tahara、M. Moriyama、J. L. Ingham 和 J. Mizutani：“来自 Piscidia erythrina 的多种含氧异黄酮”植物化学。