Two New Constituents from the Bark of Holarrhena pubescens

HETEROCYCLES
2003.0

Abstract

Two new compounds, norkurchamide (3,20-dioxo-11α-hydroxycona-1,4-diene) (1) and pubatriol (3-oxo-11α,19,22-trihydroxycona-1,4-diene) (2) have been isolated from the bark of Holarrhena pubescens. Their structures have been established through spectroscopic studies. Holarrhena pubescens [synonym: H. antidysenterica Apocynaceae] inhabits the forest areas of the subcontinent. It has been extensively studied mainly because the bark commonly known as "Kurchi" is highly reputed in traditional medicine as a remedy for amoebic dysentery and other intestinal ailments.1,2 The plant has also been reported to possess anthelmintic, appetiser, astringent and antidiarroeal properties.3 A hot decoction of bark is used as a gargle in toothache.4 Chemical studies on H. pubescens were undertaken as far back as 1858 when the alkaloid conessine was first isolated by Hains5 from the bark of the plant. Since then this plant has been extensively studied for its alkaloids6 due to their pharmacological significance. Studies undertaken by this group on the bark of the plant led to the isolation of several new compounds.7-11 In continuation of these investigations two new compounds of conanine series have now been obtained. The isolation and structure elucidation of these constituents are being reported in this paper. The structural studies are based on 1D and 2D NMR experiments (COSY 45, HMQC and HMBC) and other spectral evidences.

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