Dicaffeoylquinic acid derivatives and flavonoid glucosides from glasswort ( Salicornia herbacea L.) and their antioxidative activity

• Published in: Food chemistry Vol. 125; no. 1; pp. 55 - 62
• Main Authors: Kim, Jin Young, Cho, Jeong-Yong, Ma, Young-Kyu, Park, Keun Young, Lee, Sang-Hyun, Ham, Kyung-Sik, Lee, Hyoung Jae, Park, Keun-Hyung, Moon, Jae-Hak
• Format: Journal Article
• Language: English
• Published: Kidlington Elsevier Ltd 01-03-2011; [Amsterdam]: Elsevier Science; Elsevier
• Subjects: Antioxidant; antioxidant activity; antioxidants; Biological and medical sciences; caffeic acid; chemical constituents of plants; chemical structure; Dicaffeoylquinic acid derivatives; Flavonoid glucosides; flavonols; Food industries; Fundamental and applied biological sciences. Psychology; glycoflavonoids; phytochemicals; Salicornate; Salicornia; Salicornia herbacea; Salicornia herbacea L; Salicornia herbacea L; Dicaffeoylquinic acid derivatives; Flavonoid glucosides; Antioxidant; Salicornate; Polyphenol; Glucoside; Flavonoid
• ISSN: 0308-8146; 1873-7072
• DOI: 10.1016/j.foodchem.2010.08.035

Two novel antioxidant compounds, isoquercitrin 6″-
O-methyloxalate (
6) and methyl 4-caffeoyl-3-dihydrocaffeoyl quinate (salicornate,
7), were isolated from
Salicornia herbacea L.. Six known compounds were also identified as 3,5-dicaffeoylquinic acid (
1), quercetin 3-
O-β-
d-glucopyranoside (
2), 3-caffeoyl-4-dihydrocaffeoylquinic acid (
3), methyl 3,5-dicaffeoyl quinate (
4), 3,4-dicaffeoylquinic acid (
5), and isorhamnetin 3-
O-β-
d-glucopyranoside (
8). Their chemical structures were determined by spectroscopic data from ESI–MS and NMR. The isolated dicaffeoylquinic acid derivatives (
1,
3,
4,
5, and
7) showed similar activities for scavenging 1,1-diphenyl-2-picrylhydrazyl radicals and inhibiting formation of cholesteryl ester hydroperoxide during copper ion-induced rat blood plasma oxidation. The two flavonol glucosides (
2 and
6), which have no substitutions in the B ring of their aglycones, also had similar activity. However, compound
8, which has the same structure as
2 except for the presence of a methoxyl group in the C-3′ position of the B ring, showed predominantly lower antioxidant activity than the other isolated compounds.