Extending the record of dolabellane-type diterpenoids from the soft coral Clavularia viridis: Structures and stereochemistry

Ye-Qing Du; Yuan Gao; Yi Zang; Jia Li; Xu-Wen Li; Yue-Wei Guo

doi:10.1016/j.phytochem.2023.113671

Extending the record of dolabellane-type diterpenoids from the soft coral Clavularia viridis: Structures and stereochemistry

Phytochemistry. 2023 Jun:210:113671. doi: 10.1016/j.phytochem.2023.113671. Epub 2023 Apr 5.

Authors

Ye-Qing Du¹, Yuan Gao², Yi Zang², Jia Li³, Xu-Wen Li³, Yue-Wei Guo⁴

Affiliations

¹ State Key Laboratory of Drug Research, Shanghai Institute of Materia Medica, Chinese Academy of Sciences, 555 Zu Chong Zhi Road, Zhangjiang Hi-Tech Park, Shanghai, 201203, China; School of Chinese Materia Medica, Nanjing University of Chinese Medicine, Nanjing, 210023, China.
² State Key Laboratory of Drug Research, Shanghai Institute of Materia Medica, Chinese Academy of Sciences, 555 Zu Chong Zhi Road, Zhangjiang Hi-Tech Park, Shanghai, 201203, China.
³ State Key Laboratory of Drug Research, Shanghai Institute of Materia Medica, Chinese Academy of Sciences, 555 Zu Chong Zhi Road, Zhangjiang Hi-Tech Park, Shanghai, 201203, China; School of Chinese Materia Medica, Nanjing University of Chinese Medicine, Nanjing, 210023, China; Shandong Laboratory of Yantai Drug Discovery, Bohai rim Advanced Research Institute for Drug Discovery, Yantai, Shandong, 264117, China.
⁴ State Key Laboratory of Drug Research, Shanghai Institute of Materia Medica, Chinese Academy of Sciences, 555 Zu Chong Zhi Road, Zhangjiang Hi-Tech Park, Shanghai, 201203, China; School of Chinese Materia Medica, Nanjing University of Chinese Medicine, Nanjing, 210023, China; Shandong Laboratory of Yantai Drug Discovery, Bohai rim Advanced Research Institute for Drug Discovery, Yantai, Shandong, 264117, China; Collaborative Innovation Center of Yangtze River Delta Region Green Pharmaceuticals and College of Pharmaceutical Science, Zhejiang University of Technology, Hangzhou, 310014, China. Electronic address: ywguo@simm.ac.cn.

PMID: 37024001
DOI: 10.1016/j.phytochem.2023.113671

Abstract

Five undescribed dolabellane-type diterpenoids (1-5), together with three related known ones (6-8), were isolated from the soft coral Clavularia viridis. Their structures and stereochemistry were elucidated by extensive spectroscopic analysis and NMR calculation with DP4+ probability analysis. The absolute configurations of 1 and 5 were unambiguously determined by X-ray crystallographic analysis. A plausible biosynthetic connection between undescribed compounds 1-5 was proposed.

Keywords: Clavularia viridis; Configuration determination; Diterpenoids; Dolabellane; Structure elucidation.

MeSH terms

Animals
Anthozoa* / chemistry
Diterpenes* / chemistry
Magnetic Resonance Spectroscopy
Molecular Structure

Substances

dolabellane
Diterpenes