Streptoglycerides E–H, Unsaturated Polyketides from the Marine-Derived Bacterium Streptomyces specialis and Their Anti-Inflammatory Activity
Hee Jae Shin, Chang-Su Heo, Cao Văn Ánh, Yeo Dae Yoon, Jong Soon Kang
Abstract
Four new streptoglycerides E–H (1–4), with a rare 6/5/5/-membered ring system, were isolated from a marine-derived actinomycete Streptomyces specialis. The structures of 1–4 were elucidated by detailed analysis of HRESIMS, 1D and 2D NMR data and ECD spectra as well as comparison of their spectroscopic data with those reported in literature. Compounds 1–4 showed significant anti-inflammatory activity by inhibiting lipopolysaccharide (LPS)-induced nitric oxide (NO) production in Raw 264.7 cells with IC50 values ranging from 3.5 to 10.9 µM. Especially, 2 suppressed mRNA expression levels of iNOS and IL-6 without cytotoxicity.
Topics & Concepts
StreptomycesCytotoxicityLipopolysaccharideStereochemistryNitric oxideBacteriaTwo-dimensional nuclear magnetic resonance spectroscopyMicrobiologyChemistryAnti-inflammatoryBiologyIn vitroBiochemistryOrganic chemistryPharmacologyGeneticsEndocrinologyMicrobial Natural Products and BiosynthesisMarine Sponges and Natural ProductsSynthesis and Biological Activity