Induction of Phytoalexin Synthesis in Soybean. Structure and Reactions of Naturally Occurring and Enzymatically Prepared Prenylated Pterocarpans from Elicitor-Treated Cotyledons and Cell Cultures of Soybean

U. Zähringer 1 , E. Schaller 2  and H. Grisebach 1
  • 1 Biologisches Institut II der Universität Freiburg, Lehrstuhl für Biochemie der Pflanzen, Schänzlestr. 1, D-7800 Freiburg i. Br.
  • 2 Gödecke AG, Berlin, Werk Freiburg

Using HPLC on a partisil column (5 μm) it was possible to separate two reaction products from an enzyme incubation of dimethylallylpyrophosphate and 3,6a,9-trihydtoxypterocarpan with a particulate fraction from elicitor-treated soybean cotyledons (Harosoy 63) or soybean cell cultures. These two products were identified by MS and 1H-NMR analysis as 2- and 4-dimethylallyltrihydroxypterocarpan. Both compounds also occur as natural products in elicitor-treated soybean cotyledons and to a smaller extent in soybean cell cultures. Introduction of the dimethylallyl substituent into trihydroxypterocarpan increases the fungitoxicity against Cladosporium cucumerinum.

Upon treatment with alkali, solutions of 3,6a,9-trihydroxypterocarpans turn to an intense red colour with λmax around 530 nm. One of the products from 2-DMA-THP could be isolated by reversed phase HPLC. According to its mass spectrum a quinoid structure is proposed for this red pigment

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A Journal of Biosciences: Zeitschrift für Naturforschung C (ZNC) is an international scientific journal for the emerging field of natural and natural-like products. ZNC publishes original research on the isolation, bio-chemical synthesis and bioactivities of natural products, their biochemistry, pharmacology, biotechnology, and biological activity and innovative developed computational methods for predicting their structure and/or function.