Ching-Fun Chang

Chemical Studies on “Clover Sickness”: Part II. Biological Functions of Isoflavonoids and Their Related Compounds

The functions of isoflavonoids and related compounds as well as of their degradation products in the allelopathy of red clover were investigated from chemical standpoint. Susceptibilities of red clover to isoflavonoids, related compounds and their degradation products were higher than those of various plants including white and alsike clovers, and contents of the isoflavonoids in red clover were extremely higher as compared with those in white clover and orchard grass. Inhibitory substances were isolated from the soil capable to cause “clover sickness,” but they were not isoflavonoids but phenolic acids considered to be originated probably in the formers. These acids were also obtained together with some kinds of isoflavonoids from the waste culture solution used for cultivation of red clover seedlings. Finally degradation process of isoflavonoids was followed up in neutral, acidic and alkaline solutions.

Chemical Studies on "Clover Sickness":Part I. Isolation and Structural Elucidation of Two New Isoflavonoids in Red Clover

Two new isoflavonoids were isolated from red clover as germination inhibitors for the same plant and their structures were determined as a glucoside of biochanin A (7-d-β-glucosyl-5,7-dihydroxy-4′-methoxyisoflavone) (II) and its 5-malonate (I), respectively. Besides these compounds the following substances were also isolated as inhibitors: trifolirhizin (III), ononin (IV), daidzein (V) and its 7-glucoside (VI), formononetin (VII), genistein (VIII) and biochanin A (IX).

Aspochracin, a New Insecticidal Metabolite of Aspergillus ochraceus: Part I. Isolation, Structure and Biological ActivitiesPart II. Synthesis of Hexahydroaspochracin

A new insecticidal substance named aspochracin was isolated from the culture filtrate of Aspergillus ochraceus, a pathogenic fungus causing muscardine on insects. The compound was found to be a novel cyclotripeptide, composed of N-methyl-l-alanine, N-methyl-l-valine and l-ornithine, containing an octatrienoic acid side chain. Isolation procedure, structural elucidation and biological activities are described in detail.Hexahydroaspochracin (II) derived on hydrogenation of aspochracin (I), an insecticidal metabolite of Aspergillus ochraceus, was synthesized by cyclization of N-methyl-l-valyl-N- methyl-l-alanyl-α-caprylyl-l-ornithine (XIV). In addition to II, isohexahydroaspochracin (XV) was isolated from the reaction mixture.