1. Isolation of Lobane and Prenyleudesmane Diterpenoids from the Soft Coral Lobophytum varium
- Author
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Atallah F. Ahmed, Chuan-Hsiang Chang, Chiung-Yao Huang, Tian-Sheng Yang, Jyh-Horng Sheu, You-Cheng Lin, and Tsong-Long Hwang
- Subjects
prenyleudesmane ,food.ingredient ,Stereochemistry ,Neutrophils ,Coral ,Anti-Inflammatory Agents ,Pharmaceutical Science ,01 natural sciences ,Lobophytum ,Article ,Lobophytum varium ,chemistry.chemical_compound ,food ,Biosynthesis ,Superoxides ,Drug Discovery ,Animals ,Humans ,anti-inflammatory activity ,Pharmacology, Toxicology and Pharmaceutics (miscellaneous) ,lcsh:QH301-705.5 ,Pancreatic Elastase ,010405 organic chemistry ,Chemistry ,Superoxide ,Absolute configuration ,Stereoisomerism ,Carbon-13 NMR ,Anthozoa ,lobane ,0104 chemical sciences ,010404 medicinal & biomolecular chemistry ,lcsh:Biology (General) ,Diterpenes ,Two-dimensional nuclear magnetic resonance spectroscopy - Abstract
Further chemical investigation of the EtOAc extract of the soft coral Lobophytum varium resulted in the discovery of eleven new diterpenoids lobovarols F&ndash, P (1&ndash, 11) of lobane&ndash, and prenyleudesmane&ndash, types, along with two known metabolites (12 and 13). The structures of the new metabolites were established by spectroscopic analyses, including 2D NMR experiments. The absolute configuration of 1 was determined using Mosher&rsquo, s method. The complete assignment of 1H and 13C NMR spectroscopic data of 12 and 13 and the identification of pyran-derived moieties in the prenyleudesmanes were reported for the first time. Anti-inflammatory activities of the isolated compounds in suppressing elastase release and superoxide anion generation in human neutrophils were disclosed for 1, 2, 4, 12, and 13. A stereospecific biosynthesis for lobanes and prenyleudesmanes from the related prenylgermacranes could explain the coexistence of lobanes and prenylgermacranes in L. varium.
- Published
- 2020
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