| Two new antioxidant malonated caffeoylquinic acid isomers in fruits of wild eggplant relatives. | |
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MedLine Citation:
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PMID: 21800866 Owner: NLM Status: Publisher |
Abstract/OtherAbstract:
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Fruits of the cultivated eggplant species <i>Solanum melongena</i> and its wild relative <i>Solanum incanum</i> have a high content of hydroxycinnamic acid conjugates, which are implicated in the human health benefits of various fruits and vegetables. Monocaffeoylquinic acid esters, in particular 5-<i>O</i>-(-<i>E</i>)-caffeoylquinic acid, are usually predominant in solanaceous fruits and tubers. Two closely related caffeoylquinic acid derivatives with longer C<sub>18</sub>-HPLC retention times than those of monocaffeoylquinic acids are minor constituents in cultivated eggplant fruit. In a prior study, the two compounds were tentatively identified as 3-<i>O</i>-acetyl- and 4-<i>O</i>-acetyl-5-<i>O</i>-(<i>E</i>)-caffeoylquinic acids, and composed ≤ 2% of the total hydroxycinnamic acid conjugates in fruit of most <i>S. melongena</i> accessions. We recently found that the pair of these caffeoylquinic acid derivatives can compose 15-25% of the total hydroxycinnamic acid conjugates in fruits of <i>S. incanum</i> and wild <i>S. melongena</i>. This facilitated C18-HPLC isolation and structural elucidation using <sup>1</sup>H- and <sup>13</sup>C-NMR techniques and HR-ToF-MS. The isomeric compounds were identified as 3-<i>O</i>-malonyl-5-<i>O</i>-(<i>E</i>)-caffeoylquinic acid (isomer 1), and 4-<i>O</i>-(<i>E</i>)-caffeoyl-5-<i>O</i>-malonylquinic acid (isomer 2). Both exhibited free radical scavenging activity, albeit about fourfold lower than that of the flavonol quercetin dihydrate. By contrast, the iron chelation activities of isomers 1 and 2, respectively, were about three- and six-fold greater than that of quercetin dihydrate. Reports of malonylhydroxycinnamoylquinic acids are rare, and only a few of these compounds have been structurally elucidated using both NMR and MS techniques. To our knowledge, these two malonylcaffeoylquinic acid isomers have not previously been reported. |
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Authors:
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Chunhui Ma; Keyvan Dastmalchi; Bruce D Whitaker; Edward J Kennelly |
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Publication Detail:
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Type: JOURNAL ARTICLE Date: 2011-7-29 |
Journal Detail:
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Title: Journal of agricultural and food chemistry Volume: - ISSN: 1520-5118 ISO Abbreviation: - Publication Date: 2011 Jul |
Date Detail:
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Created Date: 2011-8-1 Completed Date: - Revised Date: - |
Medline Journal Info:
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Nlm Unique ID: 0374755 Medline TA: J Agric Food Chem Country: - |
Other Details:
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Languages: ENG Pagination: - Citation Subset: - |
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From MEDLINE®/PubMed®, a database of the U.S. National Library of Medicine
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