A new benzofuranone and anti-HIV constituents from the stems of Rhus chinensis.
A new benzofuran lactone, rhuscholide A (1), was isolated from the stems of RHUS CHINENSIS, together with six known compounds: 5-hydroxy-7-(3,7,11,15-tetramethylhexadeca-2,6,10,11-tetraenyl)-2(3 H)-benzofuranone (2), betulin (3), betulonic acid (4), moronic acid (5), 3-oxo-6 beta-hydroxyolean-12-en-28-oic acid (6) and 3-oxo-6 beta-hydroxyolean-18-en-28-oic acid (7). Based on 1D, 2D NMR (COSY, HMQC, HMBC) and mass (EI-MS, HR-EI-MS) spectral data, the structure of rhuscholide A was deduced to be 5-hydroxy-3-(propan-2-ylidene)-7-(3,7,11,15-tetramethylhexadeca-2,6,10,11-tetraenyl)-2(3 H)-benzofuranone (1). Anti-HIV-1 bioassays IN VITRO revealed that compound 1 possesses significant anti-HIV-1 activity with an EC50 value of 1.62 microM and a therapeutic index (TI) of 42.40. Compounds 2, 4, 5 and 7 showed moderate anti-HIV-1 activities with EC50 values of 3.70, 5.81, 7.49 and 13.11 microM, respectively.
Gu
Qiong
Q
State Key Laboratory of Phytochemistry and Plant Resources in West China, Kunming Institute of Botany, Chinese Academy of Sciences, Kunming, P. R. China.
Wang
Rui-Rui
RR
Zhang
Xue-Mei
XM
Wang
Yun-Hua
YH
Zheng
Yong-Tang
YT
Zhou
Jun
J
Chen
Ji-Jun
JJ
D019380:Anti-HIV Agents / Q000008:administration & dosage / Q000494:pharmacology* / Q000627:therapeutic use; D015658:HIV Infections / Q000188:drug therapy; D015497:HIV-1 / Q000187:drug effects*; D006801:Humans; D008826:Microbial Sensitivity Tests; D008517:Phytotherapy; D010936:Plant Extracts / Q000008:administration & dosage / Q000494:pharmacology* / Q000627:therapeutic use; D018547:Plant Stems; D029045:Rhus
D019380:Anti-HIV Agents; D010936:Plant Extracts