New Sesquiterpenes from Litsea verticillata.
Seven new sesquiterpenes, named litseagermacrane (1), 7-epi-eudesm-4(15)-ene-1alpha,6alpha-diol (2), 5-epi-eudesm-4(15)-ene-1beta,6beta-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-1beta,6beta-diol (3), eudesm-4(15)-ene-1beta,6alpha-diol (5), octahydro-4-hydroxy-3alpha-methyl-7-methylene-alpha-(1-methylethyl)-1H-indene-1-methanol (8), 10-hydroxyl-15-oxo-alpha-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 IC(50) values of 6.5 (27.5), 17.4 (73.1), and 28.0 (119.7) microg/mL (microM), 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.
Zhang
Hong-Jie
HJ
Program for Collaborative Research in the Pharmaceutical Sciences (m/c877), Department of Medicinal Chemistry and Pharmacognosy, College of Pharmacy, University of Illinois at Chicago, 833 S. Wood Street, 60612, USA.
Tan
Ghee Teng
GT
Santarsiero
Bernard D
BD
Mesecar
Andrew D
AD
Hung
Nguyen Van
NV
Cuong
Nguyen Manh
NM
Doel Soejarto
D
D
Pezzuto
John M
JM
Fong
Harry H S
HH
D019380:Anti-HIV Agents / Q000737:chemistry / Q000302:isolation & purification* / Q000494:pharmacology; D018360:Crystallography, X-Ray; D049452:Green Fluorescent Proteins; D020128:Inhibitory Concentration 50; D032862:Litsea / Q000737:chemistry*; D008164:Luminescent Proteins; D008968:Molecular Conformation; D015394:Molecular Structure; D019906:Nuclear Magnetic Resonance, Biomolecular; D018515:Plant Leaves / Q000737:chemistry; D010946:Plants, Medicinal / Q000737:chemistry*; D012717:Sesquiterpenes / Q000737:chemistry / Q000302:isolation & purification* / Q000494:pharmacology; D013237:Stereoisomerism; D014744:Vietnam
D019380:Anti-HIV Agents; D008164:Luminescent Proteins; D012717:Sesquiterpenes; D049452:Green Fluorescent Proteins