New Sesquiterpenes from Litsea verticillata

• Published in: Journal of natural products (Washington, D.C.) Vol. 66; no. 5; pp. 609 - 615
• Main Authors: ZHANG, Hong-Jie, TAN, Ghee Teng, SANTARSIERO, Bernard D., MESECAR, Andrew D., HUNG, Nguyen Van, CUONG, Nguyen Manh, DOEL SOEJARTO, D., PEZZUTO, John M., FONG, Harry H. S.
• Format: Journal Article
• Language: English
• Published: WASHINGTON American Chemical Society 01.05.2003; Amer Chemical Soc; American Society of Pharmacognosy
• Subjects: Anti-HIV Agents - chemistry; Anti-HIV Agents - isolation & purification; Anti-HIV Agents - pharmacology; Biological and medical sciences; Chemistry, Medicinal; Crystallography, X-Ray; General pharmacology; Green Fluorescent Proteins; Inhibitory Concentration 50; Life Sciences & Biomedicine; Litsea - chemistry; Luminescent Proteins; Medical sciences; Molecular Conformation; Molecular Structure; Nuclear Magnetic Resonance, Biomolecular; Pharmacognosy. Homeopathy. Health food; Pharmacology & Pharmacy; Pharmacology. Drug treatments; Plant Leaves - chemistry; Plant Sciences; Plants, Medicinal - chemistry; Science & Technology; Sesquiterpenes - chemistry; Sesquiterpenes - isolation & purification; Sesquiterpenes - pharmacology; Stereoisomerism; Vietnam; Asia; Vietnam; ANTI-HIV AGENTS; HIV-1 virus; Epimer; Alcohol; Medicinal plant; Dicotyledones; Sesquiterpenes; Angiospermae; Antiviral; Lauraceae; Terpenoid; Diol; Pharmacognosy; Retroviridae; Plant leaf; Lentivirus; Ketone; In vitro; Biological activity; Virus; Cell line; Plant origin; Green fluorescent protein; Phenols; Isolation; Spermatophyta; Human immunodeficiency virus; Enone; Structural analysis
• ISSN: 0163-3864; 1520-6025
• DOI: 10.1021/np020508a

Seven new sesquiterpenes, named litseagermacrane (1), 7-epi-eudesm-4(15)-ene-1a,6a-diol (2), 5-epieudesm-4(15)-ene-1b,6b-diol (4), litseahumulanes A (6) and B (7), and litseachromolaevanes A (11) and B (12), as well as the known compounds 7-epi-eudesm-4(15)-ene-1b,6b-diol (3), eudesm-4(15)-ene-1b,6a-diol (5), octahydro-4-hydroxy-3a-methyl-7-methylene-a-(1-methylethyl)-1H-indene-1-methanol (8), 10-hydroxyl-15-oxo-a-cadinol (9), and aphanamol II (10), were isolated from an anti-HIV fraction of the leaves and twigs of Litsea verticillata Hance (Figure 1). Isolates 1, 4, and 12 were found to inhibit HIV-1 replication in a green fluorescent protein (GFP)-based reporter cell line (HOG.R5) with IC50 values of 6.5 (27.5), 17.4 (73.1), and 28.0 (119.7) mg/mL (mM), respectively. The structures of these isolates were determined by spectral data including 1D and 2D NMR spectra. Compound 11 was confirmed by X-ray crystallographic analysis.