Anti-HIV Bioactive Stilbene Dimers of Caragana rosea

Abstract

Bioassay-guided fractionation of the ethanol extract of the aerial parts of Caragana rosea Turcz. led to the isolation of two new (cararosinol C and cararosinol D) and four known [scirpusin A (1), cis-scirpusin A (2), maackin (3), scirpusin B (4)] stilbene dimers. This is the first identification of these compounds from this plant and the first time that compound 2 has been isolated as a natural compound. Their structures were established mainly by spectral means. An in vitro assay against HIV-1_IIIB, demonstrated compounds 1 and 4 to be active against HIV, with EC₅₀ values of 10 μg/mL and 7 μg/mL respectively.

References

• 1 Jiang Su New Medical C ollege. Dictionary of Chinese traditional Medicine. Shanghai Science and Technology Press Shanghai; 1985: pp 1019-20
• 2 Yang G X, Hu C Q. A novel stilbenolignan from Caragana rosea Turcz.  Chin J Org Chem. 2003;  23 873-6
• 3 Yang G X, Hu C Q. A new stilbene tetramer from Caragana rosea .  Chin Chem Lett. 2003;  14 1048-50
• 4 Khan M A, Nabi S G, Prakash S, Zaman A. Pallidol, a resveratrol dimer from Cissus pallida .  Phytochemistry. 1986;  25 1945-8
• 5 Iliya I, Tanaka T, Iinuma M, Ali Z, Furasawa M, Nakaya K I. et al . Four dimeric stilbenes in stem lianas of Gentum africanum .  Heterocycles. 2002;  57 1507-12
• 6 Namkajima K, Taguchi H, Endo T, Yosioka I. The constituents of Scirpus fluviatilis (Torr.) A. Gray. I. The structures of two new hydroxystilbene dimers, scirpusin A and B.  Chem Pharm Bull. 1978;  26 3050-7
• 7 Kulesh N I, Maksimov O B, Fedoreev S A, Denisenko V A, Glasunov V P, Pokushalova T V, Glebko L I. About native components of extracts from Maackia amurensis wood.  Chem Nat Compd. 1999;  35 575-9
• 8 Kulesh N I, Isakov V V, Maksimov O B. Dimeric stilbenes of the wood of Maackia amurensis .  Chem Nat Compd. 1992;  28 407-14
• 9 Manfredi K P, Vallurupalli V, Demidova M, Kindscher K, Pannell L K. Isolation of an anti-HIV diprenylated bibenzyl from Glycyrrhiza lepidota .  Phytochemistry. 2001;  58 153-7
• 10 Dai J R, Hallock Y F, Cardellina JH I I, Boyd M R. HIV-inhibitory and cytotoxic oligostilbenes from the leaves of Hopea malibato .  J Nat Prod. 1998;  61 351-3
• 11 Montefiori DC; Zhou J Y. Selective antiviral activity of synthetic soluble L-tyrosine and L-dopa melanins against human immunodeficiency virus in vitro .  Antiviral Res. 1991;  15 11-25