Benzofuran ε-caprolactam glucosides, amides and phenylpropanoid derivatives with anti-inflammatory activity from Oxybaphus himalaicus.

Yan Qiu, Xuedong Yang, Jun Xu, Bo Liu, Xiaoxue Li

Journal: Phytochemistry 2021;191():112905

PMID: 34392008

Full Text on Elsevier Science View on PubMed

Abstract

(+)-(2S,3S)- and (-)-(2R,3R)-Oxybaphuslactam A glucosides are two undescribed benzofuran ε-caprolactams featuring a unique 7/6/5 fused tricyclic framework with p-glucosyl-O-phenyl unit. They were isolated from the root of Tibetan medicinal plant Oxybaphus himalaicus along with an undescribed sucrose ester, 3-O-feruloyl sucrose, an undescribed lignan glucoside, (7'R,8R,8'S)-3,3',5,5'-tetramethoxy-7',9-epoxylignan-9'-ol-7-one 4,4'-di-O-β--glucopyranoside and ten known amides and phenylpropanoid derivatives. Based on the spectral analyses, X-ray crystallography and comparison of experimental and TD-DFT calculated ECD spectra, the structures of these compounds were determined. The anti-inflammatory assay showed the undescribed compounds had significant inhibitory effects on the formation of NO, TNF-α and IL-6, which were evaluated by LPS induced RAW 264.7 cell model.

Address: School of Pharmaceutical Science and Technology, Tianjin University, Tianjin, 300072, China.; School of Pharmaceutical Science and Technology, Tianjin University, Tianjin, 300072, China. Electronic address: [email protected].

DOI: 10.1016/j.phytochem.2021.112905

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MeSH Terms: Amides, Anti-Inflammatory Agents, Benzofurans, Caprolactam, Glucosides, Lignans, Molecular Structure