Isolation of rhododaurichromanic acid B and the anti-HIV principles rhododaurichromanic acid A and rhododaurichromenic acid from Rhododendron dauricum

被引:229
作者
Kashiwada, Y [1 ]
Yamazaki, K
Ikeshiro, Y
Yamagishi, T
Fujioka, T
Mihashi, K
Mizuki, K
Cosentino, LM
Fowke, K
Morris-Natschke, SL
Lee, KH
机构
[1] Niigata Coll Pharm, Niigata 9502081, Japan
[2] Kitami Inst Technol, Kitami, Hokkaido 0908507, Japan
[3] Fukuoka Univ, Fac Pharmaceut Sci, Fukuoka 8140180, Japan
[4] Welfide Corp, Div Pharmaceut Res, Drug Dev Labs, Yoshitomi, Fukuoka 8718550, Japan
[5] BBI Biotech Res Labs, Gaithersburg, MD 20877 USA
[6] Univ N Carolina, Sch Pharm, Div Med Chem & Nat Prod, Nat Prod Lab, Chapel Hill, NC 27599 USA
关键词
antivirals; chromenes; chromanes; Rhododendron dauricum;
D O I
10.1016/S0040-4020(00)01144-3
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
Two novel chromane derivatives (1 and 2) and the known chromene (3) were isolated from the leaves and twigs of Rhododendron dauricum. The absolute stereostructure of 1 was established by spectroscopic examination and X-ray crystallographic analysis. The absolute stereostructures of 2 and 3 were also confirmed by photochemical conversion of 3 into 1 and 2. Daurichromenic acid (3) demonstrated potent anti-HIV activity with an EC50 value of 0.00567 mug/mL and therapeutic index (TI) of 3,710. Rhododaurichromanic acid A (1) also showed relatively potent anti-HIV activity with an EC50 value of 0.37 mug/mL, and a TI of 91.9, whereas rhododaurichromanic acid B (1) displayed no anti-HIV activity. (C) 2001 Elsevier Science Ltd. All rights reserved.
引用
收藏
页码:1559 / 1563
页数:5
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