New caryophyllene-type sesquiterpene and flavonol tetraglycoside with sixteen known compounds from sword bean (Canavalia gladiata)

• Published in: Food science and biotechnology Vol. 29; no. 10; pp. 1343 - 1353
• Main Authors: An, Hyun Jeong, Kim, Eun Hee, Lee, Hyoung Jae, Cho, Jeong-Yong, Moon, Jae-Hak
• Format: Journal Article
• Language: English
• Published: Singapore Springer Singapore 01.10.2020; Springer Nature B.V; 한국식품과학회
• Subjects: Beans; biotechnology; Canavalia gladiata; Carboxylic acids; Caryophyllene; Chemical compounds; Chemistry; Chemistry and Materials Science; Flavonols; Food Science; homoserine; Kaempferol; L-Rhamnopyranoside; lupeol; methyl gallate; NMR; Nuclear magnetic resonance; Nutrition; sesquiterpenoids; 식품과학; Flavonoid tetraglycoside; Sesquiterpenoic acid; Cerebioside; Sword bean
• ISSN: 1226-7708; 2092-6456; 2092-6456
• DOI: 10.1007/s10068-020-00794-8

Eighteen compounds including new caryophyllene-type sesquiterpene and flavonol tetraglycoside were purified and isolated from sword beans ( Canavalia gladiata ). Two new compounds, ( Z ,1 R ,7 S ,9 S )-7-hydroxy-11,11-dimethyl-8-methylenebicyclo[7.2.0]undec-4-ene-4-carboxylic acid ( 2 ) and kaempferol-7- O -α- l -dirhamnopyranosyl(1 → 2;1 → 6)- O -β- d -glucopyranosyl(1 → 2)- O -α- l -rhamnopyranoside ( 9 ), were identified. Other known compounds including methyl gallate ( 1 ), (2 S ,3 S ,4 E ,8 E )-2-aminooctadeca-4,8-diene-1,3-diol 1- O -β- d -glucopyranoside ( 3 ), (2 S ,3 S ,4 E ,8 Z )-2-aminooctadeca-4,8-diene-1,3-diol 1- O -β- d -glucopyranoside ( 4 ), lupeol ( 5 ), trilinolein ( 6 ), 1,6-di- O -galloyl β- d -glucopyranoside ( 7 ), N -(2-methoxybenzoyl)homoserine ( 8 ), dihydrophaseic acid ( 10 ), dillenetin ( 11 ), kaempferol-7- O -[2- O -β- d -glucopyranosyl-6- O -α- l -rhamnopyranosyl]-α- l -rhamnopyranoside ( 12 ), canavalioside ( 13 ), kaempferol-3- O -[2- O -β- d -glucopyranosyl-6- O -α- l -rhamnopyranosyl]-β- d -glucopyranoside ( 14 ), kaempferol-3- O -(2,6- O -α- l -dirhamnopyranosyl)-β- d -glucopyranoside ( 15 ), kaempferol-3- O -rutinoside ( 16 ), gladiatoside A 1 ( 17 ), and gladiatoside B 1 ( 18 ) were identified. The chemical structures of these compounds were determined by ESI–MS and NMR analyses.