Rare Prenylated Isoflavones from Tephrosia calophylla

Author:

Ganapaty Seru1,Nair Vimal2,Devi Devarakonda Rama3,Pannakal Steve Thomas3,Laatsch Hartmut2,Dittrich Birger4

Affiliation:

1. Gitam Institute of Pharmacy, Gitam University, Rushikonda, Visakhapatnam-530 045, India

2. Institute of Organic and Biomolecular Chemistry, University of Göttingen, Tammannstrasse 2, D-37077 Göttingen, Germany

3. A.U. College of Pharmaceutical Sciences, Andhra University, Visakhapatnam-530 003 (A.P.), India

4. Institute for Inorganic and Applied Chemistry, Martin-Luther-King-Platz 6, D-20146 Hamburg, Germany

Abstract

Chemical re-examination of the roots of T. calophylla led to the isolation of four isoflavones, namely 2′,4′,5-trihydroxy-6,7-(2″,2″-dimethylchromene)-8-γ,γ-dimethylallylisoflavone (1a, auriculatin), 2′,5-dihydroxy-6,7-(2″,2″-dimethylchromene)-4′-γ,γ-dimethylallyloxyisoflavone (2a, isoauriculatin), 3′,4′,5-trihy-droxy-6,7-(2″,2″-dimethylchromene)-8-γ,γ-dimethylallylisoflavone (1b, auriculasin), and 3′,5-dihydroxy-6,7-(2″,2″-dimethylchromene)-4′-γ,γ-dimethylallyl-oxyisoflavone (2b, isoauriculasin). Auriculasin and isoauriculasin are reported for the first time with full NMR assignments. All metabolites were fully characterized by 1D and 2D NMR techniques including COSY, HSQC, HMBC experiments, mass spectra and in part on the basis of X-ray diffraction. Accurate ‘invariom’ refinements with aspherical scattering factors were carried out for 1a, 1b and 2a.

Publisher

SAGE Publications

Subject

Complementary and alternative medicine,Plant Science,Drug Discovery,Pharmacology,General Medicine

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