LC-ESI-MS Study of the Flavonoid Glycoside Malonates of Red Clover (Trifolium pratense)
High-performance liquid chromatography−electrospray ionization−mass spectrometry (LC-ESI-MS) was applied to the analysis of the flavonoids and their glycoside malonates of the flowers and leaves of red clover (Trifolium pratense). Through LC-MS comparative studies on the plant extracts and their mal...
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Published in | Journal of agricultural and food chemistry Vol. 48; no. 2; pp. 354 - 365 |
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Main Authors | , , , , , , |
Format | Journal Article |
Language | English |
Published |
Washington, DC
American Chemical Society
01.02.2000
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Subjects | |
Online Access | Get full text |
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Summary: | High-performance liquid chromatography−electrospray ionization−mass spectrometry (LC-ESI-MS) was applied to the analysis of the flavonoids and their glycoside malonates of the flowers and leaves of red clover (Trifolium pratense). Through LC-MS comparative studies on the plant extracts and their malonate-free extracts, ∼20 flavonoid glycoside malonates were detected in the flower extract. Eight were identified as genistin 6‘ ‘-O-malonate (39), formononetin 7-O-β-d-glucoside 6‘ ‘-O-malonate (40), biochanin A 7-O-β-d-glucoside 6‘ ‘-O-malonate (41), trifoside 6‘ ‘-O-malonate (42), irilone 4‘-O-β-d-glucoside 6‘ ‘-O-malonate (43), pratensein 7-O-β-d-glucoside 6‘ ‘-O-malonate (44), isoquercitrin 6‘ ‘-O-malonate (45), and 3-methylquercetin 7-O-β-d-glucoside 6‘ ‘-O-malonate (46). About 15 other flavonoids and clovamides were proved to be present in this extract. The study also found that the flowers contained flavones as the major flavonoids, whereas the leaves had isoflavones as the major flavonoids. This is the first detection of the six malonates (39 and 42−46) in the extracts of red clover, and among them, 42, 43, and 46 are new compounds. Keywords: Trifolium pratense; red clover; Leguminosae; flavonoids; flavonoid glycoside malonates; clovamides; LC-ESI-MS analysis |
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Bibliography: | istex:9AC00F7EC2A80FA36C232D5A3C4BDEDD961A8648 ark:/67375/TPS-8JGDT41T-7 ObjectType-Article-1 SourceType-Scholarly Journals-1 ObjectType-Feature-2 content type line 23 |
ISSN: | 0021-8561 1520-5118 |
DOI: | 10.1021/jf991002+ |