title: Structural Elucidation and Structure-Anti-inflammatory Activity Relationships of Cembranoids from Cultured Soft Corals Sinularia sandensis and Sinularia flexibilis.
abstract: New cembranoids 4-carbomethoxyl-10-epigyrosanoldie E (1), 7-acetylsinumaximol B (2), diepoxycembrene B (6), dihydromanaarenolide I (8), and isosinulaflexiolide K (9), along with 11 known related metabolites, were isolated from cultured soft corals Sinularia sandensis and Sinularia flexibilis. The structures were elucidated by means of infrared, mass spectrometry, and nuclear magnetic resonance techniques, and the absolute configurations of 1, 4, 9, and 15 were further confirmed by single-crystal X-ray diffraction analysis. The absolute configurations of these coral metabolites and comparison with known analogues showed that one hypothesis (that cembrane diterpenes possessing an absolute configuration of an isopropyl group at C1 obtained from Alcyonacean soft corals belong to the α series, whereas analogues isolated from Gorgonacean corals belong to the β series) is not applicable for a small number of cembranoids. An in vitro anti-inflammatory study using LPS-stimulated macrophage-like cell line RAW 264.7 revealed that compounds 9-14 significantly suppressed the accumulation of pro-inflammatory proteins, iNOS and COX-2. Structure-activity relationship analysis indicated that cembrane-type compounds with one seven-membered lactone moiety at C-1 are potential anti-inflammatory agents. This is the first culture system in the world that has successfully been used to farm S. sandensis.
authors.affiliation: †Department of Marine Biotechnology and Resources, National Sun Yat-sen University, Kaohsiung 804, Taiwan.|‡Department of Beauty Science, Meiho University, Pingtung 912, Taiwan.
authors.forename: Tsung-Chang
authors.initials: TC
authors.lastname: Tsai
authors.affiliation: ∥Graduate Institute of Marine Biology, National Dong Hwa University, Pingtung 944, Taiwan.
authors.forename: Hsueh-Yu
authors.initials: HY
authors.lastname: Chen
authors.affiliation: †Department of Marine Biotechnology and Resources, National Sun Yat-sen University, Kaohsiung 804, Taiwan.
authors.forename: Jyh-Horng
authors.initials: JH
authors.lastname: Sheu
authors.affiliation: ⊥Department of Chemistry, National Sun Yat-sen University, Kaohsiung 804, Taiwan.
authors.forename: Michael Y
authors.initials: MY
authors.lastname: Chiang
authors.affiliation: †Department of Marine Biotechnology and Resources, National Sun Yat-sen University, Kaohsiung 804, Taiwan.
authors.forename: Zhi-Hong
authors.initials: ZH
authors.lastname: Wen
authors.affiliation: #Institute of Oceanography, National Taiwan University, Taipei 106, Taiwan.
authors.forename: Chang-Feng
authors.initials: CF
authors.lastname: Dai
authors.affiliation: ∥Graduate Institute of Marine Biology, National Dong Hwa University, Pingtung 944, Taiwan.
authors.forename: Jui-Hsin
authors.initials: JH
authors.lastname: Su
mesh_terms: D000818:Animals; D037421:Anthozoa / Q000737:chemistry*; D000893:Anti-Inflammatory Agents / Q000737:chemistry* / Q000494:pharmacology*; D051546:Cyclooxygenase 2 / Q000235:genetics / Q000276:immunology; D004224:Diterpenes / Q000737:chemistry* / Q000494:pharmacology*; D008264:Macrophages / Q000187:drug effects / Q000201:enzymology / Q000276:immunology; D051379:Mice; D052247:Nitric Oxide Synthase Type II / Q000235:genetics / Q000276:immunology; D000067996:RAW 264.7 Cells; D013329:Structure-Activity Relationship
chemical_list: D000893:Anti-Inflammatory Agents; D004224:Diterpenes; D052247:Nitric Oxide Synthase Type II; D051546:Cyclooxygenase 2
keywords: Sinularia flexibilis; Sinularia sandensis; anti-inflammatory; soft coral; structure−activity relationship