Natural anti-HIV agents-part I: (+)-demethoxyepiexcelsin and verticillatol from Litsea verticillata.
The eudesmane sesquiterpenoid, verticillatol (1), as well as the lignan, (+)-5'-demethoxyepiexcelsin (2), and a known lignan, (+)-epiexcelsin (3), were isolated from Litsea verticillata Hance. Lignan 2 showed moderate anti-HIV activity with an IC(50) value of 16.4 microg/ml (42.7 microM), while the known lignan 3 was inactive up to a concentration of 20 microg/ml (48.3 microM). Compound 1 demonstrated weak activity with an IC(50) value of 34.5 microg/ml (144.7 microM) while being devoid of cytotoxicity at 20 microg/ml. The structures were elucidated by 1D and 2D NMR spectroscopy, and the absolute configuration of the new sesquiterpenoid was determined by the generation of Mosher esters.
Hoang
Vu Dinh
VD
Program for Collaborative Research in Pharmaceutical Sciences, College of Pharmacy, University of Illinois at Chicago, 833 S. Wood St., Chicago, IL 60612, USA.
Tan
Ghee Teng
GT
Zhang
Hong-Jie
HJ
Tamez
Pamela A
PA
Hung
Nguyen Van
NV
Cuong
Nguyen Manh
NM
Soejarto
D Doel
DD
Fong
Harry H S
HH
Pezzuto
John M
JM
D019380:Anti-HIV Agents / Q000737:chemistry / Q000302:isolation & purification / Q000494:pharmacology*; D002460:Cell Line; D005663:Furans / Q000737:chemistry / Q000302:isolation & purification / Q000494:pharmacology*; D015497:HIV-1 / Q000187:drug effects / Q000472:pathogenicity; D019770:Lauraceae / Q000737:chemistry*; D017705:Lignans; D009682:Magnetic Resonance Spectroscopy; D008826:Microbial Sensitivity Tests; D015394:Molecular Structure; D012717:Sesquiterpenes / Q000737:chemistry / Q000302:isolation & purification / Q000494:pharmacology*; D021241:Spectrometry, Mass, Electrospray Ionization
C454519:5'-demethoxyepiexcelsin; D019380:Anti-HIV Agents; D005663:Furans; D017705:Lignans; D012717:Sesquiterpenes; C454499:verticillatol