title: New Bioactive Lupane Triterpene Coumaroyl Esters Isolated from Buxus cochinchinensis.
abstract: Five new lupane triterpene coumaroyl esters (1-5), together with betulin (6) and a known Buxus alkaloid, N-3-benzoyldihydrocyclomicrophylline F (7), were isolated from a CHCl3-soluble partition of a methanol extract of Buxus cochinchinensis Pierre ex Gagnep. (Buxaceae) collected in Vietnam. Isolation work was monitored using human colon cancer cells (HT-29). The structures of the new compounds (1-5) were determined on the basis of spectroscopic data interpretation. In addition to their cytotoxicity against HT-29 cells and nuclear factor-kappa B (p65) inhibitory activity in an enzyme-linked immunosorbent assay, all isolates as well as two semisynthetic compounds derived from betulin and 5, respectively, were also evaluated for their in vitro antiplasmodial activities against the drug-resistant Dd2 strain of Plasmodium falciparum and antifungal effects on the growth of the pathogenic yeast Candida albicans. The new lupane triterpene coumaroyl esters (1-5), along with a betulin derivative and the known Buxus alkaloid, were found to show significant in vitro antimalarial activities, with IC50 values ranging from 0.26 to 2.07 µM.
authors.affiliation: Division of Medicinal Chemistry and Pharmacognosy, College of Pharmacy, The Ohio State University, Columbus, OH, USA.
authors.forename: Li
authors.initials: L
authors.lastname: Pan
authors.affiliation: Division of Pharmacy Practice and Administration, College of Pharmacy, The Ohio State University, Columbus, OH, USA.
authors.forename: Ulyana
authors.initials: U
authors.lastname: Muñoz Acuña
authors.affiliation: Division of Medicinal Chemistry and Pharmacognosy, College of Pharmacy, The Ohio State University, Columbus, OH, USA.
authors.forename: Heebyung
authors.initials: H
authors.lastname: Chai
authors.affiliation: Division of Medicinal Chemistry and Pharmacognosy, College of Pharmacy, The Ohio State University, Columbus, OH, USA.
authors.forename: Hyun-Young
authors.initials: HY
authors.lastname: Park
authors.affiliation: Institute of Ecology and Biological Resources, Vietnam Academy of Science and Technology, Hoang Quoc Viet, Cau Giay, Hanoi, Vietnam.
authors.forename: Tran Ngoc
authors.initials: TN
authors.lastname: Ninh
authors.affiliation: Institute of Ecology and Biological Resources, Vietnam Academy of Science and Technology, Hoang Quoc Viet, Cau Giay, Hanoi, Vietnam.
authors.forename: Bui Van
authors.initials: BV
authors.lastname: Thanh
authors.affiliation: Department of Biochemistry and the Virginia Tech Center for Drug Discovery, M/C 0308, Virginia Tech, Blacksburg, VA, USA.
authors.forename: Emilio F
authors.initials: EF
authors.lastname: Merino
authors.affiliation: Department of Biochemistry and the Virginia Tech Center for Drug Discovery, M/C 0308, Virginia Tech, Blacksburg, VA, USA.
authors.forename: Maria B
authors.initials: MB
authors.lastname: Cassera
authors.affiliation: Division of Medicinal Chemistry and Pharmacognosy, College of Pharmacy, The Ohio State University, Columbus, OH, USA.
authors.forename: L Harinantenaina
authors.initials: LH
authors.lastname: Rakotondraibe
authors.affiliation: Division of Medicinal Chemistry and Pharmacognosy, College of Pharmacy, The Ohio State University, Columbus, OH, USA.
authors.forename: Esperanza J
authors.initials: EJ
authors.lastname: Carcache de Blanco
authors.affiliation: Department of Medicinal Chemistry and Pharmacognosy, College of Pharmacy, University of Illinois at Chicago, Chicago, IL, USA.
authors.forename: Djaja D
authors.initials: DD
authors.lastname: Soejarto
authors.affiliation: Division of Medicinal Chemistry and Pharmacognosy, College of Pharmacy, The Ohio State University, Columbus, OH, USA.
authors.forename: A Douglas
authors.initials: AD
authors.lastname: Kinghorn
mesh_terms: D000470:Alkaloids / Q000737:chemistry* / Q000302:isolation & purification / Q000494:pharmacology; D000962:Antimalarials / Q000737:chemistry* / Q000302:isolation & purification / Q000494:pharmacology; D031235:Buxus / Q000737:chemistry*; D004952:Esters / Q000737:chemistry / Q000302:isolation & purification / Q000494:pharmacology; D019073:HT29 Cells; D006801:Humans; D020128:Inhibitory Concentration 50; D015394:Molecular Structure; D010936:Plant Extracts / Q000737:chemistry* / Q000302:isolation & purification / Q000494:pharmacology; D010963:Plasmodium falciparum / Q000187:drug effects; D014315:Triterpenes / Q000737:chemistry* / Q000302:isolation & purification / Q000494:pharmacology; D014744:Vietnam; D053978:Pentacyclic Triterpenes; D000094062:Betulinic Acid
chemical_list: D000470:Alkaloids; D000962:Antimalarials; D004952:Esters; D010936:Plant Extracts; D014315:Triterpenes; C480546:lupane; D053978:Pentacyclic Triterpenes; C002503:betulin; D000094062:Betulinic Acid