Inhibitory effects on HIV-1 protease of constituents from the wood of Xanthoceras sorbifolia.
From a methanolic extract of the wood of Xanthoceras sorbifolia, two new compounds, 29-hydroxy-3-oxotirucalla-7,24-dien-21-oic acid (3, xanthocerasic acid) and epigallocatechin-(4beta-->8, 2beta-->O-7)-epicatechin (6), were isolated, together with 11 known compounds. Of the isolated compounds, 3-oxotirucalla-7, 24-dien-21-oic acid (2), oleanolic acid (4), and 6 were found to be inhibitory substances against human immunodeficiency virus (HIV-1) protease, with their 50% inhibitory concentrations (IC(50)) being 20, 10, and 70 microg/mL, respectively. Condensed tannins of high molecular weights with epicatechin and epiafzelechin as the main extender units were found to be the most active principles of this plant (IC(50) values ca. 6.0 microg/mL).
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Institute of Natural Medicine, Toyama Medical and Pharmaceutical University, 2630 Sugitani, Toyama 930-0194, Japan.
Nakamura
N
N
Hattori
M
M
Kakuda
H
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Qiao
J
J
Yu
H
H
D000872:Anthocyanins / Q000302:isolation & purification* / Q000494:pharmacology; D002392:Catechin / Q000031:analogs & derivatives*; D018360:Crystallography, X-Ray; D016333:HIV Protease; D017320:HIV Protease Inhibitors / Q000302:isolation & purification* / Q000494:pharmacology; D006801:Humans; D009682:Magnetic Resonance Spectroscopy; D008745:Methylation; D010946:Plants, Medicinal / Q000737:chemistry*; D016339:Spectrometry, Mass, Fast Atom Bombardment; D013055:Spectrophotometry, Infrared; D014315:Triterpenes / Q000302:isolation & purification* / Q000494:pharmacology; D014934:Wood
D000872:Anthocyanins; D017320:HIV Protease Inhibitors; D014315:Triterpenes; C406633:epigallocatechin-(4-8,2-O-7)epicatechin; C406632:xanthocerasic acid; D002392:Catechin; D016333:HIV Protease