title: Constituents of an extract of Cryptocarya rubra housed in a repository with cytotoxic and glucose transport inhibitory effects.
abstract: A new alkylated chalcone (1), a new 1,16-hexadecanediol diester (2), and eight known compounds were isolated from a dichloromethane-soluble repository extract of the leaves and twigs of Cryptocarya rubra collected in Hawaii. The structures of the new compounds were determined by interpretation of their spectroscopic data, and the absolute configurations of the two known cryptocaryanone-type flavonoid dimers, (+)-bicaryanone A (3) and (+)-chalcocaryanone C (4), were ascertained by analysis of their electronic circular dichroism and NOESY NMR spectra. All compounds isolated were evaluated against HT-29 human colon cancer cells, and, of these, (+)-cryptocaryone (5) was found to be potently cytotoxic toward this cancer cell line, with an IC50 value of 0.32 μM. This compound also exhibited glucose transport inhibitory activity when tested in a glucose uptake assay.
authors.affiliation: Division of Medicinal Chemistry and Pharmacognosy, College of Pharmacy, The Ohio State University , Columbus, Ohio 43210, United States.
authors.forename: Yulin
authors.initials: Y
authors.lastname: Ren
authors.forename: Chunhua
authors.initials: C
authors.lastname: Yuan
authors.forename: Yanrong
authors.initials: Y
authors.lastname: Qian
authors.forename: Hee-Byung
authors.initials: HB
authors.lastname: Chai
authors.forename: Xiaozhuo
authors.initials: X
authors.lastname: Chen
authors.forename: Michael
authors.initials: M
authors.lastname: Goetz
authors.forename: A Douglas
authors.initials: AD
authors.lastname: Kinghorn
mesh_terms: D000972:Antineoplastic Agents, Phytogenic / Q000737:chemistry / Q000302:isolation & purification* / Q000494:pharmacology*; D047188:Chalcones / Q000737:chemistry / Q000302:isolation & purification* / Q000494:pharmacology*; D031369:Cryptocarya / Q000737:chemistry*; D004354:Drug Screening Assays, Antitumor; D005947:Glucose / Q000032:analysis / Q000378:metabolism*; D019073:HT29 Cells; D006254:Hawaii; D006801:Humans; D020128:Inhibitory Concentration 50; D019906:Nuclear Magnetic Resonance, Biomolecular; D018515:Plant Leaves / Q000737:chemistry; D013237:Stereoisomerism
chemical_list: D000972:Antineoplastic Agents, Phytogenic; D047188:Chalcones; D005947:Glucose