Biosynthesis enhancement and antioxidant and anti-inflammatory activities of peanut (Arachis hypogaea L.) arachidin-1, arachidin-3, and isopentadienylresveratrol.

UNLABELLED: Peanut is a potent plant to be induced to synthesize bioactive stilbenoids. Bioactivities of those stilbenoids except resveratrol have been meagerly investigated. When peanut kernels (Tainan 14, a Spanish cultivar) were imbibed, incubated 3 days for germination, sliced, incubated with artificial aeration, periodically sampled, lyophilized, extracted with methanol, and subjected to reverse-phase HPLC analysis, four major fractionations were detected and identified as trans-resveratrol (Res), trans-arachidin-1 (Ara-1), trans-arachidin-3 (Ara-3), and trans-isopentadienylresveratrol (IPD). During incubation of the peanut slices, contents of Res, Ara-1, and Ara-3 increased tremendously from initially trace or not detectable amounts up to 147.3, 495.7, and 2414.8 microg/g, corresponding to 20, 16, and 24 h of incubation, while IPD contents continued to increase up to 28 h (4474.4 microg/g). When the four stilbenoids and butylated hydroxytoluene (BHT) were subjected to antioxidant characterization by various measures, all have exhibited varied potencies of antioxidant activity. In particular, retardation of absorbance increase at 234 nm as formation of the conjugated diene hydroperoxides in a real pork oil system stored at 60 degrees C, supplement of Ara-1 at 100 microM has shown equivalent or even greater activity than did BHT. When the media were supplemented with Res, Ara-1, Ara-3, and IPD at 15 microM for cultivation of mouse macrophage RAW 264.7 cells activated by lipopolysaccharide (LPS), the LPS-induced extracellular production of prostaglandin E2 (PGE2) and nitric oxide (NO) was significantly inhibited by Ara-1 (p < 0.001), Res (p < 0.001), Ara-3 (p < 0.01), and IPD (p < 0.01). It is noteworthy and of merit that all test stilbenoids have exhibited potent antioxidant and anti-inflammatory activities and varied as affected by number of hydroxyl groups and isopentenyl or isopentadienyl moiety. KEYWORDS: Arachis hypogaea L.; peanut; groundnut; resveratrol; stilbenoids; arachidin; antioxidant; anti-inflammation.