Sesquiterpene derivatives from marine sponge Smenospongia cerebriformis and their anti-inflammatory activity

[Display omitted] Using various chromatographic methods, five new sesquiterpene derivatives named smenohaimiens A–E (1–5) and five known, 19-hydroxy-polyfibrospongol B (6), ilimaquinone (7), dictyoceratin C (8), polyfibrospongol A (9), and polyfibrospongol B (10) were isolated from the marine sponge...

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Bibliographic Details
Published in:Bioorganic & medicinal chemistry letters 2017-04, Vol.27 (7), p.1525-1529
Main Authors: Kiem, Phan Van, Huyen, Le Thi, Hang, Dan Thuy, Nhiem, Nguyen Xuan, Tai, Bui Huu, Anh, Hoang Le Tuan, Cuong, Pham Van, Quang, Tran Hong, Minh, Chau Van, Dau, Nguyen Van, Kim, Young-A, Subedi, Lalita, Kim, Sun Yeou, Kim, Seung Hyun
Format: Article
Language:English
Subjects:
Animals
Anti-inflammation
Anti-Inflammatory Agents, Non-Steroidal - chemistry
Anti-Inflammatory Agents, Non-Steroidal - isolation & purification
Anti-Inflammatory Agents, Non-Steroidal - pharmacology
Cell Line
Circular Dichroism
Magnetic Resonance Spectroscopy
Mice
Nitric Oxide - antagonists & inhibitors
Nitric Oxide - biosynthesis
omega-N-Methylarginine - pharmacology
Porifera - chemistry
Quinones - chemistry
Quinones - isolation & purification
Quinones - pharmacology
Sesquiterpene derivative
Sesquiterpenes - chemistry
Sesquiterpenes - isolation & purification
Sesquiterpenes - pharmacology
Smenohaimiens A–E
Smenospongia cerebriformis
Stereoisomerism
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Summary:[Display omitted] Using various chromatographic methods, five new sesquiterpene derivatives named smenohaimiens A–E (1–5) and five known, 19-hydroxy-polyfibrospongol B (6), ilimaquinone (7), dictyoceratin C (8), polyfibrospongol A (9), and polyfibrospongol B (10) were isolated from the marine sponge Smenospongia cerebriformis Duchassaing & Michelotti, 1864. Their structures were assigned by 1D, 2D NMR spectroscopic analysis, HR ESI MS, and calculations of the electron circular dichroism spectra. All compounds were evaluated for the inhibitory activity against NO production in lipopolysaccharide-stimulated in BV2 microglia cells. As the results, compound 7 significantly inhibited NO production with the IC50 value of 10.40±1.28µM. The remaining compounds showed moderate inhibitory NO production activities with IC50 values ranging from 24.37 to 30.43µM.
ISSN:0960-894X
1464-3405
DOI:10.1016/j.bmcl.2017.02.040