11β,20β-Epoxybriaranes from the Gorgonian Coral Junceella fragilis (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

doi:10.3390/md18040183

11β,20β-Epoxybriaranes from the Gorgonian Coral Junceella fragilis (Ellisellidae)

Mar Drugs. 2020 Mar 31;18(4):183. doi: 10.3390/md18040183.

Authors

Tung-Pin Su^{1

2}, Tsu-Jen Kuo^{3

4

5}, San-Nan Yang⁶, Gene-Hsiang Lee⁷, Yen-Tung Lee^{8

9

10}, Yi-Chen Wang¹¹, Jih-Jung Chen¹², Zhi-Hong Wen⁴, Tsong-Long Hwang^{13

14

15

16}, Ping-Jyun Sung^{1

2

4

17

18}

Affiliations

¹ Graduate Institute of Marine Biology, National Dong Hwa University, Pingtung 94450, Taiwan.
² National Museum of Marine Biology and Aquarium, Pingtung 94450, Taiwan.
³ Department of Stomatology, Kaohsiung Veterans General Hospital, Kaohsiung 81362, Taiwan.
⁴ Department of Marine Biotechnology and Resources, National Sun Yat-sen University, Kaohsiung 80424, Taiwan.
⁵ Department of Dental Technology, Shu-Zen Junior College of Medicine and Management, Kaohsiung 82144, Taiwan.
⁶ Department of Pediatrics, E-DA Hospital, School of Medicine, College of Medicine, I-SHOU University, Kaohsiung 82445, Taiwan.
⁷ Instrumentation Center, National Taiwan University, Taipei 10617, Taiwan.
⁸ Division of Natural Products, Graduate Institute of Biomedical Sciences, College of Medicine, Chang Gung University, Taoyuan 33302, Taiwan.
⁹ Department of Cosmetic Science, College of Human Ecology, Chang Gung University of Science and Technology, Taoyuan 33303, Taiwan.
¹⁰ Department of Chinese Medicine, MacKay Memorial Hospital, Taipei 10449, Taiwan.
¹¹ Division of Cardiology, Department of Internal Medicine, Kaohsiung Armed Forces General Hospital, Kaohsiung 80284, Taiwan.
¹² Faculty of Pharmacy, School of Pharmaceutical Sciences, National Yang-Ming University, Taipei 11221, Taiwan.
¹³ 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.
¹⁴ Graduate Institute of Natural Products, College of Medicine, Chang Gung University, Taoyuan 33302, Taiwan.
¹⁵ Chinese Herbal Medicine Research Team, Healthy Aging Research Center, Chang Gung University, Taoyuan 33302, Taiwan.
¹⁶ Department of Anaesthesiology, Chang Gung Memorial Hospital, Taoyuan 33305, Taiwan.
¹⁷ Chinese Medicine Research and Development Center, China Medical University Hospital, Taichung 40447, Taiwan.
¹⁸ Graduate Institute of Natural Products, Kaohsiung Medical University, Kaohsiung 80708, Taiwan.

Abstract

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.

Keywords: COX-2; Junceella fragilis; X-ray; briarane; fragilide; iNOS; juncenolide.

MeSH terms

Animals
Anthozoa / chemistry*
Cyclooxygenase 2 / metabolism
Diterpenes / chemistry
Diterpenes / isolation & purification
Diterpenes / pharmacology*
Inflammation Mediators / chemistry
Inflammation Mediators / isolation & purification
Inflammation Mediators / pharmacology*
Mice
Nitric Oxide Synthase Type II / metabolism
RAW 264.7 Cells
Taiwan
X-Ray Diffraction

Substances

Diterpenes
Inflammation Mediators
Nitric Oxide Synthase Type II
Nos2 protein, mouse
Ptgs2 protein, mouse
Cyclooxygenase 2