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Exploring the chemical diversity of sesquiterpenes from the rarely studied south China sea soft coral Sinularia tumulosa assisted by molecular networking strategy.
- Source :
-
Phytochemistry [Phytochemistry] 2024 Jun; Vol. 222, pp. 114110. Date of Electronic Publication: 2024 Apr 23. - Publication Year :
- 2024
-
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 MIC <subscript>90</subscript> 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.<br />Competing Interests: Declaration of competing interest The authors declare that they have no known competing financial interests or personal relationships that could have appeared to influence the work reported in this paper.<br /> (Copyright © 2024 Elsevier Ltd. All rights reserved.)
- Subjects :
- Animals
Mice
Molecular Structure
Anti-Bacterial Agents pharmacology
Anti-Bacterial Agents chemistry
Anti-Bacterial Agents isolation & purification
China
RAW 264.7 Cells
Microbial Sensitivity Tests
Lipopolysaccharides pharmacology
Lipopolysaccharides antagonists & inhibitors
Structure-Activity Relationship
Humans
Antineoplastic Agents pharmacology
Antineoplastic Agents chemistry
Antineoplastic Agents isolation & purification
Density Functional Theory
Dose-Response Relationship, Drug
Anthozoa chemistry
Sesquiterpenes chemistry
Sesquiterpenes pharmacology
Sesquiterpenes isolation & purification
Subjects
Details
- Language :
- English
- ISSN :
- 1873-3700
- Volume :
- 222
- Database :
- MEDLINE
- Journal :
- Phytochemistry
- Publication Type :
- Academic Journal
- Accession number :
- 38663824
- Full Text :
- https://doi.org/10.1016/j.phytochem.2024.114110