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This study aimed to investigate the effect of fermentation with Lactobacillus plantarum NCU137 on the nutritional, sensory and stability properties of Coix (Coix lachryma-jobi L.) seed. The nutritional compounds, including free amino acid, free fatty acid, soluble dietary fiber and organic acids of fermented coix seed were significantly (p

Coix lachryma-jobi L. var. ma-yuen has been a source of food and traditional folk medicine in some parts of Asia for thousands of years; however, the roots of this plant have not been phytochemically investigated. Herein, we report the isolation of a new benzoxazinoid glycoside, coixlachryside B (1), along with ten known compounds (2–11), from the roots of C. lachryma-jobi var. ma-yuen using a variety of chromatographic methods. Among the known compounds, the absolute configuration of compound 4 was determined. The structures of all compounds were elucidated by interpreting NMR spectroscopic data, and experimental and calculated electronic circular dichroism spectra.

The effects of incubation on the nutritional and antioxidant properties of defatted adlay bran (DAB) were investigated in the current study. The results revealed that the incubation process significantly decreased pH, while increased the total titratable acidity and reducing sugar content of DAB. The DAB proteins were significantly degraded after incubation. During the 12-h incubation, the proportions of low molecular weight peptides increased gradually, and total free amino acid concentration increased 9.84-fold. Additionally, seven phenolics were detected in free and bound forms, and the incubation led to increased levels of most phenolics. Moreover, both the two phenolic fractions from incubated DAB, particularly the free fraction, demonstrated greater total phenolic content and antioxidant properties than those of non-incubated DAB. Consequently, incubation was an efficient approach to biologically modify DAB, which further enhanced the health benefits and utilization of the bran.

A new lignan glycoside, 1-[3,6-(4,4⿲-dihydroxy-3,3⿲-dimethoxy-δ-truxinyl)-β-fructofuranosyl]-α-glucopyranoside (1), named coixlachryside A, together with nine known simple phenolic compounds (3⿿11) were isolated from the roots of Coix lachryma-jobi var. ma-yuen using various chromatographic methods. Their chemical structures were determined based on the spectroscopic data interpretation, particularly circular dichroism (CD), 1D and 2D NMR data including HSQC and HMBC.

College of Pharmacy, Seoul National University, Seoul 151-742, KoreaReceived December 5, 2012, Accepted January 17, 2013Key Words : Coix lachryma-jobi L. var. ma-yuen Stapf., Gramineae, Fatty acidThe hulled seeds of Coix lachryma-jobi L. var. ma-yuenStapf. (Gramineae) have been used as a traditional herbalmedicine for treating inflammation, asthma, cough, stomachdisorder, diarrhea, and diabetes.

The first diastereoselective syntheses of the natural acetal glucosides, (2R)-2-β-d-glucopyranosyloxy-4-hydroxy-2H-1,4-benzoxazin-3(4H)-one and (2R)-2-β-d-glucopyranosyloxy-7-methoxy-2H-1,4-benzoxazin-3(4H)-one, are described by reaction of O-(2,3,4,6-tetra-O-acetyl-β-d-glucopyranosyl) trichloroacetimidate with hemiacetalic aglucones of the 2-hydroxy-2H-1,4-benzoxazin-3(4H)-one skeleton.

The anti-inflammatory activities of six benzoxazinoids isolated from roots of Coix lachryma-jobi var. ma-yuen and structurally related synthetic materials were investigated by measurement of their inhibition of histamine release from rat mast cells stimulated with concanavalin A (Con A) and sensitized with immunoglobulin E (reagin). Because the inhibition data for either Con A or IgE with these compounds were comparable, Con A can be used for rapid first-stage screening of active compounds. Four glycosides out of the eleven compounds investigated were not active. Other results showed that the free hydroxyl group at the 2-position in the benzoxazinone skeleton is important for the expression of inhibitory activity.