Exploring the chemical diversity of sesquiterpenes from the rarely studied south China sea soft coral Sinularia tumulosa assisted by molecular networking strategy

Sheng-Hui Zhu; Yuan-Min Chang; Song-Wei Li; Ming-Zhi Su; Li-Gong Yao; Lin-Fu Liang; Hong Wang; Yue-Wei Guo

doi:10.1016/j.phytochem.2024.114110

Exploring the chemical diversity of sesquiterpenes from the rarely studied south China sea soft coral Sinularia tumulosa assisted by molecular networking strategy

Phytochemistry. 2024 Apr 23:222:114110. doi: 10.1016/j.phytochem.2024.114110. Online ahead of print.

Authors

Sheng-Hui Zhu¹, Yuan-Min Chang², Song-Wei Li³, Ming-Zhi Su², Li-Gong Yao², Lin-Fu Liang⁴, Hong Wang⁵, Yue-Wei Guo⁶

Affiliations

¹ Shandong Laboratory of Yantai Drug Discovery, Bohai Rim Advanced Research Institute for Drug Discovery, Yantai, 264117, China; Collaborative Innovation Center of Yangtze River Delta Region Green Pharmaceuticals and College of Pharmaceutical Science, Zhejiang University of Technology, Hangzhou, 310014, China.
² Shandong Laboratory of Yantai Drug Discovery, Bohai Rim Advanced Research Institute for Drug Discovery, Yantai, 264117, China.
³ School of Medicine, Shanghai University, Shanghai, 200444, China.
⁴ College of Materials Science and Engineering, Central South University of Forestry and Technology, Changsha, 410004, China. Electronic address: lianglinfu@csuft.edu.cn.
⁵ Collaborative Innovation Center of Yangtze River Delta Region Green Pharmaceuticals and College of Pharmaceutical Science, Zhejiang University of Technology, Hangzhou, 310014, China. Electronic address: hongw@zjut.edu.cn.
⁶ Shandong Laboratory of Yantai Drug Discovery, Bohai Rim Advanced Research Institute for Drug Discovery, Yantai, 264117, China; Collaborative Innovation Center of Yangtze River Delta Region Green Pharmaceuticals and College of Pharmaceutical Science, Zhejiang University of Technology, Hangzhou, 310014, China; School of Medicine, Shanghai University, Shanghai, 200444, China. Electronic address: ywguo@simm.ac.cn.

PMID: 38663824
DOI: 10.1016/j.phytochem.2024.114110

Abstract

Molecular networking strategy-based prioritization of the isolation of the rarely studied soft coral Sinularia tumulosa yielded 14 sesquiterpenes. These isolated constituents consisted of nine different types of carbon frameworks, namely asteriscane, humulane, capillosane, seco-asteriscane, guaiane, dumortane, cadinane, farnesane, and benzofarnesane. Among them, situmulosaols A-C (1, 3 and 4) were previously undescribed ones, whose structures with absolute configurations were established by the combination of extensive spectral data analyses, quantum mechanical-nuclear magnetic resonance and time-dependent density functional theory electronic circular dichroism calculations, the Snatzke's method, and the modified Mosher's method. Notably, situmulosaol C (4) was the second member of capillosane-type sesquiterpenes. The plausible biogenetic relationships of these skeletally different sesquiterpenes were proposed. All sesquiterpenoids were evaluated for their antibacterial, cytotoxic and anti-inflammatory effects. The bioassay results showed compound 14 exhibited significant antibacterial activities against a variety of fish and human pathogenic bacteria with MIC₉₀ values ranging from 3.6 to 33.8 μg/mL. Moreover, moderate cytotoxic effects against HEL cells for components 13 and 14 and moderate inhibitory effect on lipopolysaccharide-induced inflammatory responses in RAW264.7 cells for substance 13 were also observed.

Keywords: Alcyoniidae; Anti-inflammatory activity; Antibacterial activity; Cytotoxicity; GNPS; Sesquiterpenes; Sinularia tumulosa; Soft coral.