title: DNA topoisomerase IIα inhibitory and anti-HIV-1 flavones from leaves and twigs of Gardenia carinata.
abstract: Four new flavones, 5,2'-dihydroxy-7,3',4',5'-tetramethoxyflavone (1), 5,2',5'-trihydroxy-7,3',4'-trimethoxyflavone (2), 5,7,2',5'-tetrahydroxy-6,3',4'-trimethoxyflavone (3) and 5,2',5'-trihydroxy-6,7,3',4'-tetramethoxyflavone (4), along with the known 5,3'-dihydroxy-6,7,4',5'-tetramethoxyflavone (5), 5,7,3',5'-tetrahydroxy-6,4'-dimethoxyflavone (6), syringaldehyde, vanillic acid and scopoletin were isolated from the leaves and twigs of Gardenia carinata (Rubiaceae). Their structures were determined by spectroscopic methods. Flavone 2 exhibited cytotoxic activity against P-388 and MCF-7 cell lines, while 3, 5 and 6 were active only in P-388 cell line. All active compounds were found to inhibit DNA topoisomerase IIα activity, which may be responsible for the observed cytotoxicity. Flavones 1-3, 5 and 6 also exhibited anti-HIV-1 activity in the anti-syncytium assay using (∆Tat/rev)MC99 virus and 1A2 cell line system; 2 was most potent. Only flavones 1 and 6 showed considerably activity against HIV-1 reverse transcriptase.
authors.affiliation: Department of Chemistry and Center for Innovation in Chemistry (PERCH-CIC), Faculty of Science, Mahidol University, Bangkok, Thailand.
authors.forename: Naowarat
authors.initials: N
authors.lastname: Kongkum
authors.forename: Patoomratana
authors.initials: P
authors.lastname: Tuchinda
authors.forename: Manat
authors.initials: M
authors.lastname: Pohmakotr
authors.forename: Vichai
authors.initials: V
authors.lastname: Reutrakul
authors.forename: Pawinee
authors.initials: P
authors.lastname: Piyachaturawat
authors.forename: Surawat
authors.initials: S
authors.lastname: Jariyawat
authors.forename: Kanoknetr
authors.initials: K
authors.lastname: Suksen
authors.forename: Chalobon
authors.initials: C
authors.lastname: Yoosook
authors.forename: Jitra
authors.initials: J
authors.lastname: Kasisit
authors.forename: Chanita
authors.initials: C
authors.lastname: Napaswad
mesh_terms: D019380:Anti-HIV Agents / Q000737:chemistry / Q000302:isolation & purification / Q000494:pharmacology*; D000951:Antigens, Neoplasm; D002470:Cell Survival; D004250:DNA Topoisomerases, Type II; D004268:DNA-Binding Proteins / Q000037:antagonists & inhibitors*; D047309:Flavones / Q000737:chemistry / Q000302:isolation & purification / Q000494:pharmacology*; D032062:Gardenia / Q000737:chemistry*; D015497:HIV-1 / Q000187:drug effects / Q000201:enzymology; D015394:Molecular Structure; D010936:Plant Extracts / Q000737:chemistry / Q000302:isolation & purification / Q000494:pharmacology*; D018515:Plant Leaves / Q000737:chemistry; D018520:Plant Shoots / Q000737:chemistry; D013329:Structure-Activity Relationship
chemical_list: C579552:5,2',5'-trihydroxy-7,3',4'-trimethoxyflavone; C579554:5,2'-dihydroxy-7,3',4',5'-tetramethoxyflavone; C579553:5,7,3',5'-tetrahydroxy-6,4'-dimethoxyflavone; D019380:Anti-HIV Agents; D000951:Antigens, Neoplasm; D004268:DNA-Binding Proteins; D047309:Flavones; D010936:Plant Extracts; D004250:DNA Topoisomerases, Type II