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Purpose <p>Excessive sunlight exposure causes cinnamic acid-containing molecules in plants to undergo geometrical isomerization, increasing metabolomic diversity which poses an analytical challenge since the resulting compounds cannot be confidently distinguished by conventional mass spectrometry. However, past studies have demonstrated that the newly formed isomers can be distinguished from their <i>trans</i> counterparts through the formation of alkali metal adducts.</p> Methods <p>Herein, ultra high-performance liquid chromatography quadrupole time-of-flight mass spectrometry (UHPLC-q-TOF-MS) was employed for the first time to characterize a sodium adduct of dimeric 4-<i>cis</i>-caffeoylquinic acid (4-<i>cis</i>-CQA) in UV-irradiated <i>Viscum combreticola</i> methanolic extracts which was observed at <i>m/z</i> 729.164. Density functional theory was used to rationalize the formation of this dimer.</p> Results <p>Theoretical modelling revealed that this compound was formed by various interactions between a neutral 4-<i>cis</i>-CQA and doubly deprotonated 4-<i>cis</i>-CQA molecules, with a Na<sup>+</sup> ion sandwiched between the two 4-CQA units through their functional groups. These interactions occurred through the π-system of the aromatic rings, along with multiple interactions, including the lone pairs of electrons on the oxygen atom of the keto group.</p> Conclusion <p>Findings of the current study further reaffirm that <i>cis</i> isomers of hydroxycinnamate containing molecules formed by UV irradiation bind sodium more efficiently than their <i>trans</i> counterparts, a phenomenon that we believe can be further exploited in the discovery and development of drugs based on metal binding as a therapeutic mechanism of action.</p>

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Sodium Adduct Formation of a UV-induced 4-cis-caffeoylquinic Acid Dimer: Insights from the UHPLC-qTOF-MS and DFT Modelling

  • 期刊论文

  • 出版模式：

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  • 发表日期：

    2025年10月28日

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  • Mailane Rose Sekgobela,
  • Lutendo Michael Mathomu,
  • Babra Moyo,
  • Mwadham Mwombeki Kabanda,
  • Ntakadzeni Edwin Madala

摘要

Purpose

Excessive sunlight exposure causes cinnamic acid-containing molecules in plants to undergo geometrical isomerization, increasing metabolomic diversity which poses an analytical challenge since the resulting compounds cannot be confidently distinguished by conventional mass spectrometry. However, past studies have demonstrated that the newly formed isomers can be distinguished from their trans counterparts through the formation of alkali metal adducts.

Methods

Herein, ultra high-performance liquid chromatography quadrupole time-of-flight mass spectrometry (UHPLC-q-TOF-MS) was employed for the first time to characterize a sodium adduct of dimeric 4-cis-caffeoylquinic acid (4-cis-CQA) in UV-irradiated Viscum combreticola methanolic extracts which was observed at m/z 729.164. Density functional theory was used to rationalize the formation of this dimer.

Results

Theoretical modelling revealed that this compound was formed by various interactions between a neutral 4-cis-CQA and doubly deprotonated 4-cis-CQA molecules, with a Na+ ion sandwiched between the two 4-CQA units through their functional groups. These interactions occurred through the π-system of the aromatic rings, along with multiple interactions, including the lone pairs of electrons on the oxygen atom of the keto group.

Conclusion

Findings of the current study further reaffirm that cis isomers of hydroxycinnamate containing molecules formed by UV irradiation bind sodium more efficiently than their trans counterparts, a phenomenon that we believe can be further exploited in the discovery and development of drugs based on metal binding as a therapeutic mechanism of action.