Sesquiterpenes and butenolides, natural anti-HIV constituents from Litsea verticillata.
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.
Zhang
Hong-Jie
HJ
Department of Medicinal Chemistry and Pharmacognosy, College of Pharmacy, The University of Illinois at Chicago, Chicago, IL, USA. zhanghj@uic.edu
Nguyen
Van Hung
VH
Nguyen
Manh Cuong
MC
Soejarto
D Doel
DD
Pezzuto
John M
JM
Fong
Harry H
HH
Tan
Ghee Teng
GT
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
D019380:Anti-HIV Agents; D010936:Plant Extracts; D012717:Sesquiterpenes; C004511:butenolide; D015107:4-Butyrolactone