Identification of Compounds in Adlay (Coix lachryma-jobi L. var. ma-yuen Stapf) Seed Hull Extracts That Inhibit Lipopolysaccharide-Induced Inflammation in RAW 264.7 Macrophages

• Published in: Journal of agricultural and food chemistry 2009-11, Vol.57 (22), p.10651-10657
• Main Authors: Huang, Din-Wen, Chung, Cheng-Pei, Kuo, Yueh-Hsiung, Lin, Yun-Lian, Chiang, Wenchang
• Format: Article
• Language: English
• Subjects: Animals; anti-inflammatory activity; Anti-Inflammatory Agents - pharmacology; Bioactive Constituents; Biological and medical sciences; cell culture; Cell Line; ceramide; Ceramides - analysis; Coix - chemistry; Coix lacryma-jobi; Dinoprostone - antagonists & inhibitors; Dinoprostone - biosynthesis; eriodictyol; Flavanones - analysis; Food industries; Fundamental and applied biological sciences. Psychology; hulls; inflammation; lipopolysaccharides; Lipopolysaccharides - pharmacology; Macrophages - drug effects; Macrophages - metabolism; medicinal plants; Mice; Nitric Oxide - antagonists & inhibitors; Nitric Oxide - biosynthesis; Plant Extracts - chemistry; Plant Extracts - pharmacology; seed extracts; Seeds - chemistry; viability
• ISSN: 0021-8561; 1520-5118
• DOI: 10.1021/jf9028514

We investigated the effects of adlay seed hull (AH) extracts on the lipopolysaccharide-induced inflammatory response in RAW 264.7 macrophages. An AH ethanol extract (AHE) was partitioned into ethyl acetate, n-butanol, and water fractions. Silica gel chromatography of the ethyl acetate fraction yielded 15 subfractions: AHE-Ea-A to AHE-Ea-O. Subfractions AHE-Ea-J, AHE-Ea-K, and AHE-Ea-M had anti-inflammatory activities, as they counteracted the increased cellular production of nitric oxide and prostaglandin E2 induced by lipopolysaccharide by down-regulating inducible nitric oxide synthase and cyclooxygenase 2 expression. Eriodictyol (1), the ceramide (2S,3S,4R)-2-[(2′R)-2′-hydroxytetracosanoyl-amino]-1,3,4-octadecanetriol (2), and p-coumaric acid (3) were found in the subfractions, and the first two compounds appeared to be primarily responsible for the anti-inflammatory activity. This is the first time that eriodictyol (1) and this ceramide (2) have been found in AH, and the anti-inflammatory properties of the AHE-Ea fraction can be attributed, at least in part, to the presence of these two compounds.