Studies on the Interaction between Plant Secondary Metabolites and Xenobiotics

通过对植物次生代谢产物与外源物质相互作用的生物和化学研究，揭示了高等植物保护设施的有效性。1.首先研究了对苯并咪唑类杀菌剂具有解毒活性的植物次生代谢物，确定了以下5个从何首乌中分离得到的化合物为抗多菌灵(苯并咪唑类杀菌剂的活性成分多菌灵和甲基托布津)，并鉴定了它们的化学结构：何首乌中的大黄素(1)和α-生育酚(2)；节节龙中的5-甲氧基-6，7-二氧基黄酮(3)和3，5-二羟基-4-甲基二苯乙烯(4)；桑白菜中的2，6-二甲氧基-1，4-苯醌(5)。2.分析了其对MBC的解毒活性与苯二酚、黄酮类化合物之间的构效关系。活性最强的化合物是对苯二酚(3-羟基-4-戊基-萘酚)和未取代黄酮类化合物或5-甲氧基黄酮类化合物。3.解毒剂对MBC的作用机制非常感兴趣，MBC被认为是微管蛋白聚合的抑制剂，从而导致有丝分裂失败。据我们目前所知，上述解毒剂在体外并不与MBC竞争β-微管蛋白的结合部位。4.从豆科鱼腥草、蔷薇科玫瑰、金莲花和金莲花、苔草等植物中分离并鉴定了具有生理活性的次生代谢物异黄酮类、倍半萜类化合物和寡二苯乙烯类化合物。(莎草科)。

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).