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

Chia-Cheng Lin; Jui-Hsin Su; Wu-Fu Chen; Zhi-Hong Wen; Bo-Rong Peng; Lin-Cyuan Huang; Tsong-Long Hwang; Ping-Jyun Sung

doi:10.3390/molecules24132487

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

Molecules. 2019 Jul 7;24(13):2487. doi: 10.3390/molecules24132487.

Authors

Chia-Cheng Lin¹, Jui-Hsin Su^{2

3}, Wu-Fu Chen^{1

4}, Zhi-Hong Wen⁴, Bo-Rong Peng², Lin-Cyuan Huang^{5

6}, Tsong-Long Hwang^{7

8

9

10

11

12}, Ping-Jyun Sung^{13

14

15

16

17}

Affiliations

¹ Department of Neurosurgery, Kaohsiung Chang Gung Memorial Hospital and Chang Gung University College of Medicine, Kaohsiung 833, Taiwan.
² National Museum of Marine Biology and Aquarium, Pingtung 944, Taiwan.
³ Graduate Institute of Marine Biology, National Dong Hwa University, Pingtung 944, Taiwan.
⁴ Department of Marine Biotechnology and Resources, National Sun Yat-sen University, Kaohsiung 804, Taiwan.
⁵ National Museum of Marine Biology and Aquarium, Pingtung 944, Taiwan. bigpa830123@gmail.com.
⁶ Graduate Institute of Marine Biology, National Dong Hwa University, Pingtung 944, Taiwan. bigpa830123@gmail.com.
⁷ Research Center for Chinese Herbal Medicine, College of Human Ecology, Chang Gung University of Science and Technology, Taoyuan 333, Taiwan. htl@mail.cgu.edu.tw.
⁸ Research Center for Food and Cosmetic Safety, College of Human Ecology, Chang Gung University of Science and Technology, Taoyuan 333, Taiwan. htl@mail.cgu.edu.tw.
⁹ Graduate Institute of Healthy Industry Technology, College of Human Ecology, Chang Gung University of Science and Technology, Taoyuan 333, Taiwan. htl@mail.cgu.edu.tw.
¹⁰ Graduate Institute of Natural Products, College of Medicine, Chang Gung University, Taoyuan 333, Taiwan. htl@mail.cgu.edu.tw.
¹¹ Chinese Herbal Medicine Research Team, Healthy Aging Research Center, Chang Gung University, Taoyuan 333, Taiwan. htl@mail.cgu.edu.tw.
¹² Department of Anaesthesiology, Chang Gung Memorial Hospital, Taoyuan 333, Taiwan. htl@mail.cgu.edu.tw.
¹³ National Museum of Marine Biology and Aquarium, Pingtung 944, Taiwan. pjsung@nmmba.gov.tw.
¹⁴ Graduate Institute of Marine Biology, National Dong Hwa University, Pingtung 944, Taiwan. pjsung@nmmba.gov.tw.
¹⁵ Department of Marine Biotechnology and Resources, National Sun Yat-sen University, Kaohsiung 804, Taiwan. pjsung@nmmba.gov.tw.
¹⁶ Graduate Institute of Natural Products, Kaohsiung Medical University, Kaohsiung 807, Taiwan. pjsung@nmmba.gov.tw.
¹⁷ Chinese Medicine Research and Development Center, China Medical University Hospital, Taichung 404, Taiwan. pjsung@nmmba.gov.tw.

Abstract

Two new 11,20-epoxybriaranes, fragilides P (1) and Q (2), as well as two known analogues, robustolide F (3) and juncin Z (4), were obtained from the gorgonian coral Junceella fragilis. The structures, including the absolute configurations of briaranes 1 and 2, were elucidated by using spectroscopic methods and comparing the spectroscopic and rotation data with those of known related analogues. Briarane 4 decreased the generation of superoxide anions by human neutrophils. The propionate group in 1 is rarely found.

Keywords: Junceella fragilis; briarane; fragilide; superoxide anion.

MeSH terms

Animals
Anthozoa / chemistry*
Diterpenes / chemistry*
Diterpenes / isolation & purification
Diterpenes / pharmacology
Models, Molecular
Molecular Conformation
Molecular Structure
Plant Proteins / chemistry*
Plant Proteins / isolation & purification
Plant Proteins / pharmacology
Spectrum Analysis

Substances

Diterpenes
Plant Proteins
juncin