Briarenols W-Z: Chlorine-Containing Polyoxygenated Briaranes from Octocoral Briareum stechei (Kükenthal, 1908)

You-Ying Chen; Yi-Lin Zhang; Gene-Hsiang Lee; Lun Kelvin Tsou; Mingzi M Zhang; Hsing-Pang Hsieh; Jih-Jung Chen; Chou-Yuan Ko; Zhi-Hong Wen; Ping-Jyun Sung

doi:10.3390/md19020077

Briarenols W-Z: Chlorine-Containing Polyoxygenated Briaranes from Octocoral Briareum stechei (Kükenthal, 1908)

Mar Drugs. 2021 Jan 31;19(2):77. doi: 10.3390/md19020077.

Authors

You-Ying Chen^{1

2}, Yi-Lin Zhang^{2

3}, Gene-Hsiang Lee⁴, Lun Kelvin Tsou⁵, Mingzi M Zhang⁶, Hsing-Pang Hsieh^{5

7

8}, Jih-Jung Chen⁹, Chou-Yuan Ko^{10

11}, Zhi-Hong Wen^{1

12}, Ping-Jyun Sung^{1

2

3

13

14}

Affiliations

¹ Department of Marine Biotechnology and Resources, National Sun Yat-sen University, Kaohsiung 804201, Taiwan.
² National Museum of Marine Biology and Aquarium, Pingtung 944401, Taiwan.
³ Graduate Institute of Marine Biology, National Dong Hwa University, Pingtung 944401, Taiwan.
⁴ Instrumentation Center, National Taiwan University, Taipei 106319, Taiwan.
⁵ Institute of Biotechnology and Pharmaceutical Research, National Health Research Institutes, Miaoli 350401, Taiwan.
⁶ Institute of Molecular and Genomic Medicine, National Health Research Institutes, Miaoli 350401, Taiwan.
⁷ Department of Chemistry, National Tsing Hua University, Hsinchu 300044, Taiwan.
⁸ Biomedical Translation Research Center, Academia Sinica, Taipei 115202, Taiwan.
⁹ Faculty of Pharmacy, School of Pharmaceutical Sciences, National Yang Ming Chiao Tung University, Taipei 112304, Taiwan.
¹⁰ Division of Gastroenterology, Department of Internal Medicine, Kaohsiung Armed Forces General Hospital, Kaohsiung 802301, Taiwan.
¹¹ Institute of Medical Science and Technology, National Sun Yat-sen University, Kaohsiung 804201, Taiwan.
¹² Institute of BioPharmaceutical Sciences, National Sun Yat-sen University, Kaohsiung 804201, Taiwan.
¹³ Chinese Medicine Research and Development Center, China Medical University Hospital, Taichung 404394, Taiwan.
¹⁴ Graduate Institute of Natural Products, Kaohsiung Medical University, Kaohsiung 807378, Taiwan.

Abstract

Briareum stechei is proven to be a rich source of 3,8-cyclized cembranoids (briarane) with a bicyclo[8.4.0] carbon core. In the present study, four previously unreported briaranes, briarenols W-Z (1-4), along with solenolide A (5), briarenolide M (6), briaexcavatolide F (7), and brianolide (8), were isolated and characterized through spectroscopic analysis, and the absolute configuration of 8 was corroborated by a single-crystal x-ray diffraction analysis. Briaranes 2 and 5 were found to induce significant inflammatory activity in lipopolysaccharide (LPS)-induced RAW 264.7 mouse macrophage cells by enhancing the expression of the inducible nitric oxide synthase (iNOS) and cyclooxygenase-2 (COX-2) proteins.

Keywords: Briareum stechei; COX-2; briarane; briarenol; iNOS; inflammation.

MeSH terms

Animals
Anthozoa / chemistry*
Chlorine
Diterpenes / chemistry
Diterpenes / isolation & purification*
Diterpenes / pharmacology
Magnetic Resonance Spectroscopy
Mice
RAW 264.7 Cells

Substances

Diterpenes
Chlorine

Grants and funding

MOST 107-2320-B-291-001-MY3, 108-2638-B-400-001-MY2, and 109-2320-B-291-001-MY3/Ministry of Science and Technology of Taiwan