alexa LC–MSn analysis of the cis isomers of chlorogenic acids


Journal of Chemical Biology & Therapeutics

Author(s): Clifford MN, Kirkpatrick J, Kuhnert N, Roozendaal H, Salgado PR

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The behaviour of cis isomers of selected mono- and di-acyl chlorogenic acids produced by UV-irradiation has been investigated by LC–MSn. cis Isomers fragment identically to the more common trans isomers. cis-5-Acyl chlorogenic acids are more hydrophobic and elute later than their mono- or di-trans counterparts whereas the reverse is true for cis-3-acyl and cis-4-acyl chlorogenic acids. The cis isomers of 1,3-dicaffeoylquinic acid, the only 1-acyl chlorogenic acid investigated, are also more hydrophobic than the di-trans isomer. Coffee leaves had a proportionately greater content of cis isomers relative to trans isomers compared with coffee beans suggesting that UV-irradiation in vivo may also cause geometric isomerisation.

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This article was published in Food Chem and referenced in Journal of Chemical Biology & Therapeutics

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