Open AccessNew caryophyllene-type sesquiterpene and flavonol tetraglycoside with sixteen known compounds from sword bean (Canavalia gladiata)
Author(s) -
Hyun Jeong An,
Eun Hee Kim,
Hyoung Jae Lee,
Jeong-Yong Cho,
Jae–Hak Moon
Publication year - 2020
Publication title -
food science and biotechnology/food science and biotechnology
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.595
H-Index - 38
eISSN - 2092-6456
pISSN - 1226-7708
DOI - 10.1007/s10068-020-00794-8
Subject(s) - chemistry , stereochemistry , kaempferol , sesquiterpene , methyl gallate , lupeol , caryophyllene , organic chemistry , gallic acid , quercetin , essential oil , chromatography , antioxidant
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.