title: Isolation, structure elucidation, and biological evaluation of 16,23-epoxycucurbitacin constituents from Eleaocarpus chinensis.
abstract: Eight new 16,23-epoxycucurbitacin derivatives, designated as elaeocarpucins A-H (1-8), and five known cucurbitacins (9-13) were isolated from the chloroform-soluble partitions of separate methanol extracts of the fruits and stem bark of Elaeocarpus chinensis collected in Vietnam. Isolation work was facilitated using a LC/MS dereplication procedure, and bioassay-guided fractionation was monitored using HT-29 human cancer cells. The structures of compounds 1-8 were determined on the basis of spectroscopic data interpretation, with the absolute configurations of isomers 1 and 2 established by the Mosher ester method. Compounds 1-13 were evaluated in vitro against the HT-29 cell line and using a mitochondrial transmembrane potential assay. Elaeocarpucin C (3), produced by partial synthesis from 16α,23α-epoxy-3β,20β-dihydroxy-10αH,23βH-cucurbit-5,24-dien-11-one (13), was found to be inactive when evaluated in an in vivo hollow fiber assay using three different cancer cell types (dose range 0.5-10 mg/kg/day, i.p.).
authors.affiliation: Division of Medicinal Chemistry and Pharmacognosy, College of Pharmacy, The Ohio State University, Columbus, Ohio 43210, United States.
authors.forename: Li
authors.initials: L
authors.lastname: Pan
authors.forename: Yeonjoong
authors.initials: Y
authors.lastname: Yong
authors.forename: Ye
authors.initials: Y
authors.lastname: Deng
authors.forename: Daniel D
authors.initials: DD
authors.lastname: Lantvit
authors.forename: Tran Ngoc
authors.initials: TN
authors.lastname: Ninh
authors.forename: Heebyung
authors.initials: H
authors.lastname: Chai
authors.forename: Esperanza J
authors.initials: EJ
authors.lastname: Carcache de Blanco
authors.forename: Djaja D
authors.initials: DD
authors.lastname: Soejarto
authors.forename: Steven M
authors.initials: SM
authors.lastname: Swanson
authors.forename: A Douglas
authors.initials: AD
authors.lastname: Kinghorn
mesh_terms: D000972:Antineoplastic Agents, Phytogenic / Q000737:chemistry / Q000302:isolation & purification* / Q000494:pharmacology*; D054728:Cucurbitacins / Q000737:chemistry / Q000302:isolation & purification* / Q000494:pharmacology*; D004354:Drug Screening Assays, Antitumor; D005638:Fruit; D019073:HT29 Cells; D006801:Humans; D015394:Molecular Structure; D024301:Plant Bark / Q000737:chemistry; D014744:Vietnam
chemical_list: D000972:Antineoplastic Agents, Phytogenic; D054728:Cucurbitacins