Three new phloroglucinol derivatives from Hypericum scabrum

Abstract

A chemical investigation on the aerial parts of Hypericum scabrum L. resulted in the isolation of three new phloroglucinol derivatives, hyperscabrins A (1), B (2), and C (3), together with one known compound, (2R,3R,4S,6R)-3-methyl-4,6-di(3-methyl-2-butenyl)-2-(2-methyl-1-oxopropyl)-3-(4-methyl-3-pentenyl)-cyclohexanone (4). The structures were elucidated by means of spectroscopic methods, including MS, IR, 1D NMR, and 2D NMR, and the absolute configurations of chiral centers in these phloroglucinol derivatives were determined for the first time by studying their circular dichroism spectra.

Keywords:

• Guttiferae
• Hypericum scabrum
• phloroglucinol

Acknowledgments

The authors acknowledge the Department of Instrumental Analysis, Institute of Materia Medica, Chinese Academy of Medical Sciences, and Peking Union Medical College for all spectral analysis. We are all greatly indebted to Prof. Yi-Kang Si for her help in the determination of absolute configuration and to Prof. Jin Li of Xinjiang Normal University for the identification of plant.