Isolation and Structure Elucidation of Cembranoids from a Dongsha Atoll Soft Coral Sarcophyton stellatum

Atallah F Ahmed; Yi-Wei Chen; Chiung-Yao Huang; Yen-Ju Tseng; Chi-Chen Lin; Chang-Feng Dai; Yang-Chang Wu; Jyh-Horng Sheu

doi:10.3390/md16060210

Isolation and Structure Elucidation of Cembranoids from a Dongsha Atoll Soft Coral Sarcophyton stellatum

Mar Drugs. 2018 Jun 14;16(6):210. doi: 10.3390/md16060210.

Authors

Atallah F Ahmed^{1

2}, Yi-Wei Chen³, Chiung-Yao Huang⁴, Yen-Ju Tseng⁵, Chi-Chen Lin⁶, Chang-Feng Dai⁷, Yang-Chang Wu⁸, Jyh-Horng Sheu^{9

10

11

12}

Affiliations

¹ Department of Marine Biotechnology and Resources, National Sun Yat-sen University, Kaohsiung 804, Taiwan. afahmed@KSU.EDU.SA.
² Department of Pharmacognosy, College of Pharmacy, King Saud University, Riyadh 11451, Saudi Arabia. afahmed@KSU.EDU.SA.
³ Department of Marine Biotechnology and Resources, National Sun Yat-sen University, Kaohsiung 804, Taiwan. m985020005@student.nsysu.edu.tw.
⁴ Department of Marine Biotechnology and Resources, National Sun Yat-sen University, Kaohsiung 804, Taiwan. huangcy@mail.nsysu.edu.tw.
⁵ Department of Marine Biotechnology and Resources, National Sun Yat-sen University, Kaohsiung 804, Taiwan. d935020003@student.nsysu.edu.tw.
⁶ Institute of Biomedical Sciences, National Chung Hsing University, Taichung 402, Taiwan. lincc@dragon.nchu.edu.tw.
⁷ Institute of Oceanography, National Taiwan University, Taipei 112, Taiwan. corallab@ntu.edu.tw.
⁸ Graduate Institute of Natural Products, Kaohsiung Medical University, Kaohsiung 807, Taiwan. yachwu@kmu.edu.tw.
⁹ Department of Marine Biotechnology and Resources, National Sun Yat-sen University, Kaohsiung 804, Taiwan. sheu@mail.nsysu.edu.tw.
¹⁰ Graduate Institute of Natural Products, Kaohsiung Medical University, Kaohsiung 807, Taiwan. sheu@mail.nsysu.edu.tw.
¹¹ Frontier Center for Ocean Science and Technology, National Sun Yat-sen University, Kaohsiung 804, Taiwan. sheu@mail.nsysu.edu.tw.
¹² Department of Medical Research, China Medical University Hospital, China Medical University, Taichung 404, Taiwan. sheu@mail.nsysu.edu.tw.

Abstract

Six new polyoxygenated cembrane-based diterpenoids, stellatumolides A⁻C (1⁻3), stellatumonins A and B (4 and 5), and stellatumonone (6), were isolated together with ten known related compounds (7⁻16) from the ethyl acetate (EtOAc) extract of soft coral Sarcophyton stellatum. The structures of the new compounds were established by extensive spectroscopic analyses, including 1D and 2D nuclear magnetic resonance (NMR) spectroscopy and data comparison with related structures. Compounds 8 and 14 were isolated from a natural source for the first time. The isolated metabolites were shown to be not cytotoxic against a limited panel of cancer cells. Compound 9 showed anti-inflammatory activity by reducing the expression of proinflammatory cyclooxygenase-2 (COX-2) and inducible nitric oxide synthase (iNOS) proteins in lipopolysaccharide (LPS)-stimulated mouse leukaemic monocyte macrophage (RAW 264.7) cells.

Keywords: Sarcophyton stellatum; anti-inflammatory activity; cembranoid; cytotoxic activity; soft coral.

MeSH terms

Animals
Anthozoa / chemistry*
Cell Line, Tumor
Cyclooxygenase 2 / metabolism
Cyclooxygenase 2 Inhibitors / chemistry*
Cyclooxygenase 2 Inhibitors / isolation & purification
Cyclooxygenase 2 Inhibitors / pharmacology
Diterpenes / chemistry*
Diterpenes / isolation & purification
Diterpenes / pharmacology
Drug Screening Assays, Antitumor
Humans
Inhibitory Concentration 50
Lipopolysaccharides / pharmacology
Macrophages / drug effects
Macrophages / metabolism
Magnetic Resonance Spectroscopy
Mice
Molecular Structure
Nitric Oxide Synthase Type II / antagonists & inhibitors
Nitric Oxide Synthase Type II / metabolism

Substances

Cyclooxygenase 2 Inhibitors
Diterpenes
Lipopolysaccharides
Nitric Oxide Synthase Type II
Nos2 protein, mouse
Ptgs2 protein, mouse
Cyclooxygenase 2