title: Diterpenes from the Hainan soft coral Lobophytum cristatum Tixier-Durivault.
abstract: Two new prenylgermacrane-type diterpenoids, lobophytumins A and B (1 and 2), two new prenyleudesmane-type diterpenoids, lobophytumins C and D (3 and 4), and two new spatane-type diterpenoids, lobophytumins E and F (5 and 6), were isolated from the Hainan soft coral Lobophytum cristatum Tixier-Durivault. Their structures, including relative configuration, were elucidated by detailed analysis of spectroscopic data and by comparison with related known compounds. In addition, the absolute configuration of lobophytumin C (3) was tentatively assigned by comparing its specific rotation with that of the closely related model compound (-)-β-selinene (8). On the basis of biogenetic considerations, the absolute configurations of lobophytumins A, B, and D-F were also tentatively suggested. This is the first report of spatane-type diterpenoids from a soft coral source. The present work supports Faulkner's proposal of prenylgermacrene as the precursor of many diterpenes. In a bioassay, lobophytumins C and D (3 and 4) showed weak in vitro cytotoxicities against the tumor cell lines A-549 and HCT-116.
authors.affiliation: State Key Laboratory of Drug Research, Shanghai Institute of Materia Medica, Chinese Academy of Sciences, Zu Chong Zhi Road 555, Zhangjiang Hi-Tech Park, Shanghai 201203, People's Republic of China.
authors.forename: Liang
authors.initials: L
authors.lastname: Li
authors.forename: Li
authors.initials: L
authors.lastname: Sheng
authors.forename: Chang-Yun
authors.initials: CY
authors.lastname: Wang
authors.forename: Yu-Bo
authors.initials: YB
authors.lastname: Zhou
authors.forename: Hui
authors.initials: H
authors.lastname: Huang
authors.forename: Xiu-Bao
authors.initials: XB
authors.lastname: Li
authors.forename: Jia
authors.initials: J
authors.lastname: Li
authors.forename: Ernesto
authors.initials: E
authors.lastname: Mollo
authors.forename: Margherita
authors.initials: M
authors.lastname: Gavagnin
authors.forename: Yue-Wei
authors.initials: YW
authors.lastname: Guo
mesh_terms: D000818:Animals; D037421:Anthozoa / Q000737:chemistry*; D000970:Antineoplastic Agents / Q000737:chemistry / Q000302:isolation & purification* / Q000494:pharmacology; D004224:Diterpenes / Q000737:chemistry / Q000302:isolation & purification* / Q000494:pharmacology; D004354:Drug Screening Assays, Antitumor; D006801:Humans; D015394:Molecular Structure; D019906:Nuclear Magnetic Resonance, Biomolecular; D045787:Sesquiterpenes, Eudesmane; D013237:Stereoisomerism; D013764:Tetrahydronaphthalenes / Q000737:chemistry
chemical_list: D000970:Antineoplastic Agents; D004224:Diterpenes; D045787:Sesquiterpenes, Eudesmane; D013764:Tetrahydronaphthalenes; C087920:beta-selinene