Natural anti-HIV agents. Part 3: Litseaverticillols A-H, novel sesquiterpenes from Litsea verticillata

Hongjie ZHANG, Ghee Teng Tan, Vu Dinh Hoang, Nguyen Van Hung, Nguyen Manh Cuong, Djaja Doel Soejarto, John M. Pezzuto, Harry H.S. Fong*

*Corresponding author for this work

Research output: Contribution to journalArticlepeer-review

39 Citations (Scopus)

Abstract

Bioassay directed-fractionation led to the identification of litseaverticillols A-H (1-8) from the leaves and twigs of Litsea verticillata Hance. These new sesquiterpenes possess a unique skeleton that was recently designated as 'litseane'. The structures of these compounds were determined by spectroscopic means including 1D and 2D NMR data. Structural configurations were determined by ROESY experiments. Mosher ester reactions and optical rotation measurements established the sesquiterpenes 1-8 as racemates. Isolates 1-8 inhibited HIV-1 replication in HOG.R5 cells with IC50 values ranging from 2 to 15μg/ml (8-58μM) while affecting the growth of HOG.R5 at concentrations 2-3-fold higher. Based on this data, structure-activity relationships can be discerned, suggesting compounds of this class are good candidates for analog production.

Original languageEnglish
Pages (from-to)141-148
Number of pages8
JournalTetrahedron
Volume59
Issue number2
DOIs
Publication statusPublished - 6 Jan 2003

Scopus Subject Areas

  • Biochemistry
  • Drug Discovery
  • Organic Chemistry

User-Defined Keywords

  • Anti-HIV activity
  • Bioassay-directed fractionation
  • Lauraceae
  • Litsea verticillata
  • Litseane
  • Litseaverticillols A-H
  • Sesquiterpenes

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