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

Authors
Kashiwada, Y Yamazaki, K Ikeshiro, Y Yamagishi, T Fujioka, T Mihashi, K Mizuki, K Cosentino, LM Fowke, K Morris-Natschke, SL Lee, KH
Citation
Y. Kashiwada et al., Isolation of rhododaurichromanic acid B and the anti-HIV principles rhododaurichromanic acid A and rhododaurichromenic acid from Rhododendron dauricum, TETRAHEDRON, 57(8), 2001, pp. 1559-1563
Citations number
5
Categorie Soggetti
Chemistry & Analysis","Organic Chemistry/Polymer Science
Journal title
TETRAHEDRON
ISSN journal
00404020 → ACNP
Volume
57
Issue
8
Year of publication
2001
Pages
1559 - 1563
Database
ISI
SICI code
0040-4020(20010218)57:8<1559:IORABA>2.0.ZU;2-E
Abstract
Two novel chromane derivatives (1 and 2) and the known chromene (3) were is olated from the leaves and twigs of Rhododendron dauricum. The absolute ste reostructure of 1 was established by spectroscopic examination and X-ray cr ystallographic analysis. The absolute stereostructures of 2 and 3 were also confirmed by photochemical conversion of 3 into 1 and 2. Daurichromenic ac id (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.