1035968-25-2Relevant academic research and scientific papers
Structural and stereochemical studies of α-methylene-γ-lactone- bearing cembrane diterpenoids from a South China Sea soft coral Lobophytum crassum
Zhang, Wen,Krohn, Karsten,Ding, Jian,Miao, Ze-Hong,Zhou, Xiu-Hong,Chen, Si-Han,Pescitelli, Gennaro,Salvador, Piero,Kurtan, Tibor,Guo, Yue-Wei
, p. 961 - 966 (2008)
Four new α-methylene-γ-lactone-bearing cembranoids, 20-acetylsinularolide B (6), presinularolide B (7), 3-dehydroxylpresinularolide B (8), and 3-dehydroxyl-20-acetylpresinularolide B (9), together with five known analogues, sinularolides B - E (1-4) and 20-acetylsinularolide C (5), were isolated from a South China Sea soft coral Lobophytum crassum. Their structures and relative stereochemistry were established by a combination of detailed spectroscopic data analysis and chemical correlations. The structures of 1-9 were further confirmed by an X-ray diffraction study on a single crystal of sinularolide B (1). The absolute configurations of sinularolide B (1) and presinularolide B (7) were determined by a novel solid-state CD/TDDFT approach and by a modified Mosher's method, respectively. This study also revealed that the coupling constant between the lactonic methine protons 3J 1,2) varies considerably with different functional groups on the cembrane ring and that the determination of the stereochemistry of lactone ring fusion based on this coupling constant is risky. In a bioassay, sinularolides B and C (1 and 2) and new cembranoids 7 and 8 showed in vitro cytotoxicity against the tumor cell lines A-549 and P-388.
Durumolides A-E, anti-inflammatory and antibacterial cembranolides from the soft coral Lobophytum durum
Cheng, Shi-Yie,Wen, Zhi-Hong,Chiou, Shu-Fen,Hsu, Chi-Hsin,Wang, Shang-Kewi,Dai, Chang-Feng,Chiang, Michael Y.,Duh, Chang-Yih
, p. 9698 - 9704 (2008/12/22)
Chemical investigations on the acetone extract of the soft coral Lobophytum durum have afforded five new cembranoids with a trans-fused α-methylene-γ-lactone, durumolides A-E (1, 6, and 8-10), and five previously characterized cembrane-based diterpenoids (2-5 and 7). The structures of the isolated metabolites were elucidated through extensive spectroscopic analyses, while the relative stereochemistry of 4 was confirmed by X-ray diffraction analyses. Moreover, the absolute configurations of 3-5 and 8 were established by application of modified Mosher's method. The anti-inflammatory effects, antibacterial activities, and inhibition assay of HCMV (Human cytomegalovirus) endonuclease activity of these isolated metabolites 1-10 were evaluated in vitro.
