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Anti-neuroinflammatory activities of indole alkaloids from kanjang (Korean fermented soy source) in lipopolysaccharide-induced BV2 microglial cells

Kim, Dong-Cheol, Quang, Tran Hong, Yoon, Chi-Su, Ngan, Nguyen Thi Thanh, Lim, Seong-Il, Lee, So-Young, Kim, Youn-Chul, Oh, Hyuncheol
Food chemistry 2016 v.213 pp. 69-75
anti-inflammatory activity, indole acetic acid, indole alkaloids, inducible nitric oxide synthase, lipopolysaccharides, metabolites, methanol, nitric oxide, nuclear magnetic resonance spectroscopy, prostaglandin synthase, prostaglandins, screening, soy sauce, soybeans, transcription factor NF-kappa B
Kanjang (Korean soy sauce) is a byproduct of the production of the Korean fermented soybean. In the present study, seven indole alkaloid derivatives were isolated from methanol extract of kanjang. Their structures were identified as 1-propyl-1,2,3,4-tetrahydro-β-carboline-3-carboxylic acid (1), 1-methyl-1,2,3,4-tetrahydro-β-carboline-3-carboxylic acid (2), 1-methyl-1,2,3,4-tetrahydro-β-carboline-1-carboxylic acid (3), 3-indoleacetic acid (4), Nb-acetyltryptamine (5), 1-methyl-3,4-dihydro-β-carboline (6), and flazine (7) by NMR and MS analyses. Preliminary screening for anti-neuroinflammatory effects of isolated indole alkaloids in lipopolysaccharide (LPS)-stimulated BV2 cells revealed that these compounds inhibited the production of nitric oxide and prostaglandin E2. For the subsequent investigation of anti-neuroinflammatory action of these metabolites, compounds 4 and 7 were selected, and the results revealed that these inhibitory effects correlated with the suppressive effect of 4 and 7 on inducible nitric oxide synthase and cyclooxygenase-2 expression in LPS-stimulated BV2 cells. In regards to the mechanism of the anti-inflammatory effect, 4 and 7 significantly inhibited the nuclear factor-kappa B pathway.