New caryophyllene-type sesquiterpene and flavonol tetraglycoside with sixteen known compounds from sword bean ( Canavali
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New caryophyllene-type sesquiterpene and flavonol tetraglycoside with sixteen known compounds from sword bean (Canavalia gladiata) Hyun Jeong An1 • Eun Hee Kim1 • Hyoung Jae Lee1 • Jeong-Yong Cho1 Jae-Hak Moon1
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Received: 18 April 2020 / Revised: 29 June 2020 / Accepted: 6 July 2020 Ó The Korean Society of Food Science and Technology 2020
Abstract Eighteen compounds including new caryophyllene-type sesquiterpene and flavonol tetraglycoside were purified and isolated from sword beans (Canavalia gladiata). Two new compounds, (Z,1R,7S,9S)-7-hydroxy-11, 11-dimethyl-8-methylenebicyclo[7.2.0]undec-4-ene-4-carboxylic acid (2) and kaempferol-7-O-a-L-dirhamnopyranosyl(1 ? 2;1 ? 6)-O-b-D-glucopyranosyl(1 ? 2)-O-aL-rhamnopyranoside (9), were identified. Other known compounds including methyl gallate (1), (2S,3S,4E,8E)-2aminooctadeca-4,8-diene-1,3-diol 1-O-b-D-glucopyranoside (3), (2S,3S,4E,8Z)-2-aminooctadeca-4,8-diene-1,3diol 1-O-b-D-glucopyranoside (4), lupeol (5), trilinolein (6), 1,6-di-O-galloyl b-D-glucopyranoside (7), N-(2methoxybenzoyl)homoserine (8), dihydrophaseic acid (10), dillenetin (11), kaempferol-7-O-[2-O-b-D-glucopyranosyl6-O-a-L-rhamnopyranosyl]-a-L-rhamnopyranoside (12), canavalioside (13), kaempferol-3-O-[2-O-b-D-glucopyranosyl-6-O-a-L-rhamnopyranosyl]-b-D-glucopyranoside
Electronic supplementary material The online version of this article (https://doi.org/10.1007/s10068-020-00794-8) contains supplementary material, which is available to authorized users. & Jae-Hak Moon [email protected] Hyun Jeong An [email protected] Eun Hee Kim [email protected] Hyoung Jae Lee [email protected] Jeong-Yong Cho [email protected] 1
Department of Food Science and Technology, Chonnam National University, Gwangju 61186, Republic of Korea
(14), kaempferol-3-O-(2,6-O-a-L-dirhamnopyranosyl)-b-Dglucopyranoside (15), kaempferol-3-O-rutinoside (16), gladiatoside A1 (17), and gladiatoside B1 (18) were identified. The chemical structures of these compounds were determined by ESI–MS and NMR analyses. Keywords Canavalia galidata Sword bean Flavonoid tetraglycoside Sesquiterpenoic acid Cerebioside
Introduction Sword bean (Canavalia gladiata) belongs to the legume family, and it is widely cultivated in Asia and Africa (Lee and Jeong, 2005). The green fruit of sword bean is generally used as a domestic vegetable, and a ripe seed is consumed as cooked beans (Chang et al., 2011; Ekanayake et al., 2007). The bean has been used in traditional Chinese medicine for the treatment of purulent inflammation, such as sinusitis, hemorrhoids, and boils (Kim et al., 2012). Sword bean has been demonstrated to have several biological effects, including anti-oxidant (Gan et al., 2016), anti-bacterial (Lee and Jeong, 2005; Cho et al., 2000), antigastric inflammatory (Kim et al., 2013a, b), attenuation of bowel disease (Ji et al., 2018), and antiangiogenic activity (Jeon et al., 2005). Interestingly, sword bean does not contain isoflavones, such as daidzin, genistin, daidzein, and genistein, which are common bioactive compounds
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