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

Nov 6, 2009Journal of agricultural and food chemistry

Compounds in adlay seed hulls that reduce inflammation caused by bacterial toxins in immune cells

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Abstract

The ethyl acetate fraction of adlay seed hull extracts showed anti-inflammatory activity by reducing nitric oxide and prostaglandin E2 production.

Subfractions AHE-Ea-J, AHE-Ea-K, and AHE-Ea-M counteracted the inflammatory response induced by lipopolysaccharide in macrophages.
These subfractions down-regulated the expression of inducible nitric oxide synthase and cyclooxygenase 2.
Eriodictyol and a specific ceramide were identified as key compounds contributing to the anti-inflammatory effects.
This is the first identification of eriodictyol and the ceramide in adlay seed hull extracts.

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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.

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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

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