title: Polyprenylated Benzoylphloroglucinols with DNA Polymerase Inhibitory Activity from the Fruits of Garcinia schomburgkiana.
abstract: Chemical investigation of the fruits of Garcinia schomburgkiana collected in Vietnam led to the isolation of eight new schomburgkianones, A-H (1-8), four known (9-12) polyprenylated benzoylphloroglucinols, and four known biflavonoids. The structures of these compounds were elucidated by spectroscopic and chemical means. The absolute configuration at C-40 of 1 and 2 was determined by (1)H NMR analyses of their MPA esters. The configuration of the bicyclo[3.3.1]nonane core of the polyprenylated benzoylphloroglucinols was assigned by comparison of their experimental ECD spectra with those of related compounds. The polyprenylated benzoylphloroglucinols exhibited inhibitory activities against mammalian DNA polymerases α and λ, with IC50 values ranging from 5.0 to 8.8 μM. Compounds 1, 2, 4, 5, and 9-11 showed cytotoxic effects against HeLa human cervical cancer cells with median lethal dose values lower than 10 μM.
authors.affiliation: Kobe Pharmaceutical University , Kobe 658-8558, Japan.
authors.forename: Duy Hoang
authors.initials: DH
authors.lastname: Le
authors.affiliation: Kobe Pharmaceutical University , Kobe 658-8558, Japan.
authors.forename: Katsumi
authors.initials: K
authors.lastname: Nishimura
authors.affiliation: Kobe Pharmaceutical University , Kobe 658-8558, Japan.
authors.forename: Yukiko
authors.initials: Y
authors.lastname: Takenaka
authors.affiliation: Graduate School of Agriculture, Shinshu University , Kamiina-gun, Nagano 399-4598, Japan.
authors.forename: Yoshiyuki
authors.initials: Y
authors.lastname: Mizushina
authors.affiliation: Kobe Pharmaceutical University , Kobe 658-8558, Japan.
authors.forename: Takao
authors.initials: T
authors.lastname: Tanahashi
mesh_terms: D000972:Antineoplastic Agents, Phytogenic / Q000737:chemistry / Q000302:isolation & purification* / Q000494:pharmacology; D004256:DNA Polymerase I / Q000037:antagonists & inhibitors*; D004354:Drug Screening Assays, Antitumor; D004365:Drugs, Chinese Herbal / Q000737:chemistry / Q000302:isolation & purification* / Q000494:pharmacology; D005638:Fruit / Q000737:chemistry*; D029760:Garcinia / Q000737:chemistry*; D006367:HeLa Cells; D006801:Humans; D020128:Inhibitory Concentration 50; D015394:Molecular Structure; D010696:Phloroglucinol / Q000031:analogs & derivatives / Q000737:chemistry / Q000494:pharmacology; D014744:Vietnam
chemical_list: D000972:Antineoplastic Agents, Phytogenic; D004365:Drugs, Chinese Herbal; D010696:Phloroglucinol; D004256:DNA Polymerase I