8-C-Prenylated flavones from the roots of tephrosia hildebrandtii

Publication Type

Journal Article

Journal Name

Journal of Natural Products

Publication Date

1-1-1986

Abstract

Tephrosia hildebrandtii Vatke (Leguminosae) is a herbaceous plant occurring in East Africa (1). From the roots of T. hildebrandtii, we have previously described the isolation and identification of hildecarpin, a new 6a-hydroxypterocarpan with insect antifeedant and antifungal properties (2,3), and the isolation and identification of four new ß-substituted flavans (4). Here we report the isolation of two 8-C-prenylated flavones during a further study of the roots of T. hildebrandtii. They have been identified as 5,7-dimethoxy-8-(3“-hydroxy-3”-methyl-trans-but-1-enyl) flavone and 5,7-dimethoxy-8-(3“-methyl-trans-but-1,3-dienyl)-flavone, named trans-tephrostachin and trans-anhydrotephrostachin, respectively (5). Both trans-tephrostachin and trans-anhydrotephrostachin have been previously isolated from Tephrosia bracteolata Guill. et Perr. (5). Although trans-anhydrotephrostachin might reasonably be suspected as an artifact generated in the isolation procedure by dehydration of trans-tephrostachin, this does not, in fact, appear to be the case. Trans-anhydrotephrostachin appeared in the tic of the original cold MeOH extract. Under the same conditions, no trans-anhydrotephrostachin was evident as a dehydration product occurring during the tic of pure trans-tephrostachin. © 1986, American Chemical Society. All rights reserved.

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