Natural anti-HIV agents. Part IV. Anti-HIV constituents from Vatica cinerea.
In a continuing search for anti-HIV compounds from plants of Vietnam, 19 compounds, including a new triterpene, were isolated from an extract of the leaves and stem of Vatica cinerea. The new triterpene was determined to be a cycloartane triterpenoid with 29 skeletal carbons and was assigned the name vaticinone (1). The known triterpenes included three cycloartanes, a lanostane, two dammaranes, three lupanes, an ursane, and an oleanane. A chlorophyll isolate was identified as pheophorbide a (13). The majority of the triterpenes, the sesquiterpene, 1-hydroxycyclocolorenone, and pheophorbide a showed anti-HIV activity, with the chlorophyll being the most active, demonstrating an IC(50) value of 1.5 microgram/mL (2.5 microM), while being completely devoid of toxicity up to a concentration of 20 microgram/mL (33.8 microM). Vaticinone (1) was found to inhibit the replication of HIV-1, with an IC(50) value of 6.5 microgram/mL (15.3 microM; selective index = 1.4). The structures of these isolates were determined by spectral data including 1D and 2D NMR spectra.
Zhang
Hong-Jie
HJ
Program for Collaborative Research in the Pharmaceutical Sciences, Department of Medicinal Chemistry, University of Illinois at Chicago, Chicago, Illinois 60612, USA.
Tan
Ghee Teng
GT
Hoang
Vu Dinh
VD
Hung
Nguyen Van
NV
Cuong
Nguyen Manh
NM
Soejarto
D Doel
DD
Pezzuto
John M
JM
Fong
Harry H S
HH
D019380:Anti-HIV Agents / Q000737:chemistry / Q000302:isolation & purification* / Q000494:pharmacology; D002734:Chlorophyll / Q000737:chemistry / Q000302:isolation & purification / Q000494:pharmacology; D020448:Ericales / Q000737:chemistry*; D006801:Humans; D020128:Inhibitory Concentration 50; D008968:Molecular Conformation; D015394:Molecular Structure; D019906:Nuclear Magnetic Resonance, Biomolecular; D012516:Osteosarcoma; D018515:Plant Leaves; D018547:Plant Stems / Q000737:chemistry; D010946:Plants, Medicinal / Q000737:chemistry*; D012717:Sesquiterpenes / Q000737:chemistry / Q000302:isolation & purification / Q000494:pharmacology; D013237:Stereoisomerism; D014315:Triterpenes / Q000737:chemistry / Q000302:isolation & purification* / Q000494:pharmacology; D014407:Tumor Cells, Cultured / Q000187:drug effects; D014744:Vietnam
D019380:Anti-HIV Agents; D012717:Sesquiterpenes; D014315:Triterpenes; C475240:vaticinone; D002734:Chlorophyll