title: Enantioselective synthesis of dictyoceratin-A (smenospondiol) and -C, hypoxia-selective growth inhibitors from marine sponge.
abstract: Total syntheses of (+)-dictyoceratin-C (1) and (+)-dictyoceratin-A (smenospondiol) (2), hypoxia-selective growth inhibitors isolated from marine sponge, were executed. The absolute stereochemistry of the each compound was determined through the enantioselective total syntheses of them. It revealed that the unnatural enantiomers of them also exhibited the hypoxia-selective growth inhibitory activity against human prostate cancer DU-145 cells.
authors: Graduate School of Pharmaceutical Sciences, Osaka University, 1-6 Yamada-oka, Suita, Osaka 565-0871, Japan.
authors: Yuji
authors: Y
authors: Sumii
authors: Graduate School of Pharmaceutical Sciences, Osaka University, 1-6 Yamada-oka, Suita, Osaka 565-0871, Japan. Electronic address: kotoku@phs.osaka-u.ac.jp.
authors: Naoyuki
authors: N
authors: Kotoku
authors: Graduate School of Pharmaceutical Sciences, Osaka University, 1-6 Yamada-oka, Suita, Osaka 565-0871, Japan.
authors: Akinori
authors: A
authors: Fukuda
authors: Graduate School of Pharmaceutical Sciences, Osaka University, 1-6 Yamada-oka, Suita, Osaka 565-0871, Japan.
authors: Takashi
authors: T
authors: Kawachi
authors: Graduate School of Pharmaceutical Sciences, Osaka University, 1-6 Yamada-oka, Suita, Osaka 565-0871, Japan.
authors: Yuta
authors: Y
authors: Sumii
authors: Graduate School of Pharmaceutical Sciences, Osaka University, 1-6 Yamada-oka, Suita, Osaka 565-0871, Japan.
authors: Masayoshi
authors: M
authors: Arai
authors: Graduate School of Pharmaceutical Sciences, Osaka University, 1-6 Yamada-oka, Suita, Osaka 565-0871, Japan. Electronic address: kobayasi@phs.osaka-u.ac.jp.
authors: Motomasa
authors: M
authors: Kobayashi
mesh_terms: D000818:Animals; D015687:Cell Hypoxia; D045744:Cell Line, Tumor; D049109:Cell Proliferation / Q000187:drug effects*; D004354:Drug Screening Assays, Antitumor; D006131:Growth Inhibitors / Q000138:chemical synthesis* / Q000737:chemistry / Q000494:pharmacology*; D006801:Humans; D062385:Hydroxybenzoates / Q000138:chemical synthesis* / Q000737:chemistry / Q000494:pharmacology*; D008297:Male; D008386:Marine Biology; D011161:Porifera / Q000737:chemistry*; D011471:Prostatic Neoplasms / Q000473:pathology; D012717:Sesquiterpenes / Q000138:chemical synthesis* / Q000737:chemistry / Q000494:pharmacology*; D013237:Stereoisomerism
chemical_list: D006131:Growth Inhibitors; D062385:Hydroxybenzoates; D012717:Sesquiterpenes; C493697:dictyoceratin-C; C000595511:smenospondiol
keywords: (+)-Dictyoceratin-A (smenospondiol); (+)-Dictyoceratin-C; Absolute stereochemistry; Hypoxia-selective growth inhibitor; Total synthesis