Chlorine-containing polyacetoxybriarane diterpenoids from the octocoral Junceella fragilis

Hai Nhat Do; Yu-Ta Chen; Su-Ying Chien; You-Ying Chen; Mingzi M. Zhang; Lun Kelvin Tsou; Jih-Jung Chen; Zhi-Hong Wen; Yi-Hao Lo; Li-Guo Zheng; Ping-Jyun Sung

doi:10.1039/D4RA03062A

Chlorine-containing polyacetoxybriarane diterpenoids from the octocoral Junceella fragilis†

Hai Nhat Do,‡^ab Yu-Ta Chen,‡^c Su-Ying Chien,^d You-Ying Chen,^b Mingzi M. Zhang,

^e Lun Kelvin Tsou,^f Jih-Jung Chen,^g Zhi-Hong Wen,^a Yi-Hao Lo,^chi Li-Guo Zheng

*^j and Ping-Jyun Sung

*^abklm

Author affiliations

* Corresponding authors

^a Department of Marine Biotechnology and Resources, National Sun Yat-sen University, Kaohsiung 804201, Taiwan

^b National Museum of Marine Biology & Aquarium, Pingtung 944401, Taiwan
E-mail: pjsung@nmmba.gov.tw

^c Department of Family Medicine, Zuoying Armed Forces General Hospital, Kaohsiung 813204, Taiwan

^d Instrumentation Center, National Taiwan University, Taipei 106319, Taiwan

^e Institute of Molecular and Genomic Medicine, National Health Research Institutes, Miaoli 350401, Taiwan

^f Institute of Biotechnology and Pharmaceutical Research, National Health Research Institutes, Miaoli 350401, Taiwan

^g Department of Pharmacy, School of Pharmaceutical Sciences, National Yang Ming Chia Tung University, Taipei 112304, Taiwan

^h Shu-Zen Junior College of Medicine and Management, Kaohsiung 821004, Taiwan

ⁱ Institute of Medical Science and Technology, National Sun Yat-sen University, Kaohsiung 804201, Taiwan

^j Doctoral Degree Program in Marine Biotechnology, National Sun Yat-sen University, Kaohsiung 804201, Taiwan
E-mail: t0919928409@gmail.com

^k Chinese Medicine Research and Development Center, China Medical University Hospital, Taichung 404394, Taiwan

^l Graduate Institute of Natural Products, Kaohsiung Medical University, Kaohsiung 807378, Taiwan

^m PhD Program in Pharmaceutical Biotechnology, Fu Jen Catholic University, New Taipei City 242062, Taiwan

Abstract

The chemical screening of an octocoral identifed as Junceella fragilis has led to the isolation of five chlorinated briarane-type diterpenoids, including three known metabolites, gemmacolide X (1), frajunolide I (2), and fragilide F (3), along with two new analogs, 12α-acetoxyfragilide F (4) and 12α-acetoxyjunceellin (5). Single-crystal X-ray diffraction analysis was carried out to determine the absolute configurations of 1 and 2, while the structures of new compounds 4 and 5 were ascertained with 2D NMR experiments. Briaranes 1 and 3–5 were active in enhancing alkaline phosphatase (ALP) activity.

RSC Advances

Chlorine-containing polyacetoxybriarane diterpenoids from the octocoral Junceella fragilis†

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Chlorine-containing polyacetoxybriarane diterpenoids from the octocoral Junceella fragilis

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