title: Sesquiterpenes and butenolides, natural anti-HIV constituents from Litsea verticillata.
abstract: In a continuing investigation, six sesquiterpenes, as well as five butenolides were isolated from the leaves and twigs of Litsea verticillata Hance (Lauraceae). Among the isolates, three were determined to be new sesquiterpenes: isolitseanes A (1), B (2) and C (3); three known sesquiterpenes were identified as oxyphyllenodiol B (4), 1,2,3,4-tetrahydro-2,5-dimethyl-8-(1-methylethyl)-1,2-naphthalenediol (5), and chromolaevanedione (6). The butenolides include the novel litseabutenolide (9) and four known compounds: 3- epi-litsenolide D2 (7), cis-listenolide D1 (8), 4-hydroxy-2-methylbut-2-enolide (10), and hydroxydihydrobovolide (11). Isolates 2, 4, 5, 7, 9, 10 and 11 were found to inhibit HIV-1 replication in a green fluorescent protein (GFP)-based reporter cell line (HOG.R5) with IC50 values of 38.1, 54.6, 91.0, 9.9, 40.3, 129.8, and 122.7 microM, respectively. Structure elucidation and identification were based on spectroscopic means including 1D and 2D NMR analyses.
authors.affiliation: Department of Medicinal Chemistry and Pharmacognosy, College of Pharmacy, The University of Illinois at Chicago, Chicago, IL, USA. zhanghj@uic.edu
authors.forename: Hong-Jie
authors.initials: HJ
authors.lastname: Zhang
authors.forename: Van Hung
authors.initials: VH
authors.lastname: Nguyen
authors.forename: Manh Cuong
authors.initials: MC
authors.lastname: Nguyen
authors.forename: D Doel
authors.initials: DD
authors.lastname: Soejarto
authors.forename: John M
authors.initials: JM
authors.lastname: Pezzuto
authors.forename: Harry H
authors.initials: HH
authors.lastname: Fong
authors.forename: Ghee Teng
authors.initials: GT
authors.lastname: Tan
mesh_terms: D015107:4-Butyrolactone / Q000008:administration & dosage / Q000031:analogs & derivatives* / Q000737:chemistry / Q000494:pharmacology / Q000627:therapeutic use; D019380:Anti-HIV Agents / Q000008:administration & dosage / Q000737:chemistry / Q000494:pharmacology* / Q000627:therapeutic use; D015497:HIV-1 / Q000187:drug effects*; D006801:Humans; D020128:Inhibitory Concentration 50; D032862:Litsea; D008517:Phytotherapy; D010936:Plant Extracts / Q000008:administration & dosage / Q000737:chemistry / Q000494:pharmacology* / Q000627:therapeutic use; D012717:Sesquiterpenes / Q000008:administration & dosage / Q000737:chemistry / Q000494:pharmacology / Q000627:therapeutic use
chemical_list: D019380:Anti-HIV Agents; D010936:Plant Extracts; D012717:Sesquiterpenes; C004511:butenolide; D015107:4-Butyrolactone