title: Natural anti-HIV agents. Part IV. Anti-HIV constituents from Vatica cinerea.
abstract: 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.
authors.affiliation: Program for Collaborative Research in the Pharmaceutical Sciences, Department of Medicinal Chemistry, University of Illinois at Chicago, Chicago, Illinois 60612, USA.
authors.forename: Hong-Jie
authors.initials: HJ
authors.lastname: Zhang
authors.forename: Ghee Teng
authors.initials: GT
authors.lastname: Tan
authors.forename: Vu Dinh
authors.initials: VD
authors.lastname: Hoang
authors.forename: Nguyen Van
authors.initials: NV
authors.lastname: Hung
authors.forename: Nguyen Manh
authors.initials: NM
authors.lastname: Cuong
authors.forename: D Doel
authors.initials: DD
authors.lastname: Soejarto
authors.forename: John M
authors.initials: JM
authors.lastname: Pezzuto
authors.forename: Harry H S
authors.initials: HH
authors.lastname: Fong
mesh_terms: 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
chemical_list: D019380:Anti-HIV Agents; D012717:Sesquiterpenes; D014315:Triterpenes; C475240:vaticinone; D002734:Chlorophyll