Further polyoxygenated cembranoids from South China Sea soft coral Sarcophyton ehrenbergi

Geng Li; Heng Li; Wei Tang; Li-Gong Yao; Lin-Fu Liang; Yue-Wei Guo

doi:10.1016/j.bioorg.2020.103993

Further polyoxygenated cembranoids from South China Sea soft coral Sarcophyton ehrenbergi

Bioorg Chem. 2020 Aug:101:103993. doi: 10.1016/j.bioorg.2020.103993. Epub 2020 Jun 2.

Authors

Geng Li¹, Heng Li², Wei Tang², Li-Gong Yao³, Lin-Fu Liang⁴, Yue-Wei Guo⁵

Affiliations

¹ State Key Laboratory of Drug Research, Shanghai Institute of Materia Medica, Chinese Academy of Sciences, Shanghai 201203, China; University of Chinese Academy of Sciences, No. 19A Yuquan Road, Beijing 100049, China.
² Laboratory of Immunopharmacology, Shanghai Institute of Materia Medica, Chinese Academy of Sciences, Shanghai 201203, China; University of Chinese Academy of Sciences, No. 19A Yuquan Road, Beijing 100049, China.
³ State Key Laboratory of Drug Research, Shanghai Institute of Materia Medica, Chinese Academy of Sciences, Shanghai 201203, China.
⁴ College of Materials Science and Engineering, Central South University of Forestry and Technology, 498 South Shaoshan Road, Changsha 410004, China. Electronic address: lianglinfu@aliyun.com.
⁵ State Key Laboratory of Drug Research, Shanghai Institute of Materia Medica, Chinese Academy of Sciences, Shanghai 201203, China; College of Materials Science and Engineering, Central South University of Forestry and Technology, 498 South Shaoshan Road, Changsha 410004, China; University of Chinese Academy of Sciences, No. 19A Yuquan Road, Beijing 100049, China. Electronic address: ywguo@simm.ac.cn.

PMID: 32544737
DOI: 10.1016/j.bioorg.2020.103993

Abstract

Eleven new cembrane diterpenes, namely, sarcoehrenins A-J (1-9, 11) and (2S,11S,12S)-isosarcophytoxide (10), along with six known compounds, gibberosene B (12), (13S)-cembra-1,3,7,11-tetraen-13-ol (13), (+)-sarcophtol (14), cembrene-C (15), (1R,4R,2E,7E,11E)-cembra-2,7,11-trien-4-ol (16) and (1S,4R,2E,7E,11E)-cembratrien-4-ol (17) were isolated from the soft coral Sarcophyton ehrenbergi collected from Weizhou Island, Beibu Gulf, South China Sea. The structures of these compounds were elucidated by a combination of detailed spectroscopic analyses, chemical methods, and comparison with reported data. The absolute configuration of compound 2 was established by the modified Mosher's method in association with TDDFT ECD calculation, while the absolute configuration of compound 3 was assigned by TDDFT ECD approach. In in vitro bioassays, compounds 13 and 17 showed potent TNF-α inhibitory activities being similar to that of positive control dexamethasone. A preliminary structural-activity relationship was also described.

Keywords: Cembrane-type diterpenoids; ECD calculation; Modified Mosher's method; Sarcophyton ehrenbergi; Soft coral; TNF-α inhibitory activity.

Publication types

Research Support, Non-U.S. Gov't

MeSH terms

Animals
Anthozoa / chemistry*
Diterpenes / chemistry
Diterpenes / isolation & purification*
Diterpenes / pharmacology
Mice
Oxygen / chemistry*
RAW 264.7 Cells
Seawater
Spectrum Analysis / methods
Structure-Activity Relationship
Tumor Necrosis Factor-alpha / antagonists & inhibitors

Substances

Diterpenes
Tumor Necrosis Factor-alpha
Oxygen