11β,20β-Epoxybriaranes from the Gorgonian Coral <i>Junceella fragilis</i> (Ellisellidae)
Tung-Pin Su,
Tsu-Jen Kuo,
San-Nan Yang,
Gene-Hsiang Lee,
Yen-Tung Lee,
Yi-Chen Wang,
Jih-Jung Chen,
Zhi-Hong Wen,
Tsong-Long Hwang,
Ping-Jyun Sung
Affiliations
Tung-Pin Su
Graduate Institute of Marine Biology, National Dong Hwa University, Pingtung 94450, Taiwan
Tsu-Jen Kuo
Department of Stomatology, Kaohsiung Veterans General Hospital, Kaohsiung 81362, Taiwan
San-Nan Yang
Department of Pediatrics, E-DA Hospital, School of Medicine, College of Medicine, I-SHOU University, Kaohsiung 82445, Taiwan
Gene-Hsiang Lee
Instrumentation Center, National Taiwan University, Taipei 10617, Taiwan
Yen-Tung Lee
Division of Natural Products, Graduate Institute of Biomedical Sciences, College of Medicine, Chang Gung University, Taoyuan 33302, Taiwan
Yi-Chen Wang
Division of Cardiology, Department of Internal Medicine, Kaohsiung Armed Forces General Hospital, Kaohsiung 80284, Taiwan
Jih-Jung Chen
Faculty of Pharmacy, School of Pharmaceutical Sciences, National Yang-Ming University, Taipei 11221, Taiwan
Zhi-Hong Wen
Department of Marine Biotechnology and Resources, National Sun Yat-sen University, Kaohsiung 80424, Taiwan
Tsong-Long Hwang
Research Center for Chinese Herbal Medicine, Research Center for Food and Cosmetic Safety, Graduate Institute of Healthy Industry Technology, College of Human Ecology, Chang Gung University of Science and Technology, Taoyuan 33303, Taiwan
Ping-Jyun Sung
Graduate Institute of Marine Biology, National Dong Hwa University, Pingtung 94450, Taiwan
Two 11,20-epoxybriaranes, including a known compound, juncenolide K (1), as well as a new metabolite, fragilide X (2), have been isolated from gorgonian Junceella fragilis collected off the waters of Taiwan. The absolute configuration of juncenolide K (1) was determined by single-crystal X-ray diffraction analysis for the first time in this study and the structure, including the absolute configuration of briarane 2 was established on the basis of spectroscopic analysis and compared with that of model compound 1. One aspect of the stereochemistry of the known compound 1 was revised. Briarane 2 was found to enhance the generation of inducible nitric oxide synthase (iNOS) and cyclooxygenase-2 (COX-2) release from RAW 264.7 cells.
