Original Paper Natural Product Chemistry	Planta Med 2005; 71: 452-457 DOI: 10.1055/s-2005-864142
© Georg Thieme Verlag KG Stuttgart · New York
Sesquiterpenes and Butenolides, Natural Anti-HIV Constituents from Litsea verticillata
Hong-Jie Zhang1, Nguyen Van Hung2, Nguyen Manh Cuong3, D. Doel Soejarto1, John M. Pezzuto1,4, Harry. H. S. Fong1, Ghee Teng Tan1
1 Program for Collaborative Research in the Pharmaceutical Sciences, Department of Medicinal Chemistry and Pharmacognosy, College of Pharmacy, The University of Illinois at Chicago, Chicago, IL, USA 2 Institute of Chemistry, Vietnamese Academy of Science and Technology, Hanoi, Vietnam 3 Cuc Phuong National Park, Nho Quan District, Ninh Binh Province, Vietnam 4 Current address: Schools of Pharmacy, Nursing, and Health Sciences, Purdue University, West Lafayette, IN, USA

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 μM, respectively. Structure elucidation and identification were based on spectroscopic means including 1D and 2D NMR analyses.

Key words

Litsea verticillata - Lauraceae - anti-HIV activity - bioassay-directed fractionation - sesquiterpenes - butenolides