title: Phloroglucinols with prooxidant activity from Garcinia subelliptica.
abstract: A new phloroglucinol, garcinielliptone HF ( 1), possessing an unprecedented skeleton, and the tautomeric pair of garcinielliptone FC ( 2/ 2a) were isolated from the heartwood and pericarp of Garcinia subelliptica, respectively. Their structures, including relative configurations, were elucidated by means of spectroscopic methods. The ability of compounds 1 and 2/ 2a to induce DNA-cleavage activity was examined using supercoiled plasmid pBR322 DNA. In the presence of Cu(II), compounds 1 and 2/ 2a caused significant breakage of pBR322 DNA. The involvement of H2O2 and O2 (*-), and H2O2, O2 (*-), and OH (*) in 1- and 2/ 2a-mediated scission, respectively, was established by inhibition or no protection of DNA breakage by various oxygen radical scavengers. Thus, in the presence Cu(II), 1 and 2/ 2a may show a prooxidant effect on DNA and induce cell death.
authors.affiliation: School of Pharmacy, Kaohsiung Medical University, Kaohsiung 807, Taiwan, Republic of China.
authors.forename: Chien-Chang
authors.initials: CC
authors.lastname: Wu
authors.forename: Yi-Huang
authors.initials: YH
authors.lastname: Lu
authors.forename: Bai-Luh
authors.initials: BL
authors.lastname: Wei
authors.forename: Shyh-Chyun
authors.initials: SC
authors.lastname: Yang
authors.forename: Shen-Jen
authors.initials: SJ
authors.lastname: Won
authors.forename: Chun-Nan
authors.initials: CN
authors.lastname: Lin
mesh_terms: D001577:Benzophenones / Q000737:chemistry / Q000302:isolation & purification* / Q000494:pharmacology*; D016923:Cell Death / Q000187:drug effects; D003300:Copper / Q000494:pharmacology; D004247:DNA / Q000187:drug effects; D016166:Free Radical Scavengers / Q000494:pharmacology; D029760:Garcinia / Q000737:chemistry*; D015394:Molecular Structure; D016877:Oxidants / Q000737:chemistry / Q000302:isolation & purification* / Q000494:pharmacology*; D010084:Oxidation-Reduction; D010696:Phloroglucinol / Q000737:chemistry / Q000302:isolation & purification* / Q000494:pharmacology*; D010946:Plants, Medicinal / Q000737:chemistry*; D010957:Plasmids / Q000187:drug effects; D013237:Stereoisomerism
chemical_list: D001577:Benzophenones; D016166:Free Radical Scavengers; D016877:Oxidants; C528162:garcinielliptone HF; D003300:Copper; D004247:DNA; D010696:Phloroglucinol