Investigation of the Photochemical Changes of Chlorogenic Acids Induced by Ultraviolet Light in Model Systems and in Agricultural Practice with Stevia rebaudiana Cultivation as an Example

Hande Karaköse, Rakesh Jaiswal, Sagar Deshpande, Nikolai Kuhnert

Research output: Contribution to journalArticle

19 Scopus citations

Abstract

Mono- and diacyl chlorogenic acids undergo photochemical trans-cis isomerization under ultraviolet (UV) irradiation. The photochemical equilibrium composition was established for eight selected derivatives. In contrast to all other dicaffeoylquinic acid derivatives, cynarin (1,3-dicaffeoylquinic acid) undergoes a [2 + 2] photochemical cycloaddition reaction, constituting a first example of Schmidt's law in a natural product family. The relevance of photochemical isomerization in agricultural practice was investigated using 120 samples of Stevia rebaudiana leave samples grown under defined cultivation conditions. Ratios of cis to trans chlorogenic acids were determined in leaf samples and correlated with climatic and harvesting conditions. The data indicate a clear correlation between the formation of cis-caffeoyl derivatives and sunshine hours prior to harvesting and illustrate the relevance of UV exposure to plant material affecting its phytochemical composition.

Original languageEnglish (US)
Pages (from-to)3338-3347
Number of pages10
JournalJournal of agricultural and food chemistry
Volume63
Issue number13
DOIs
StatePublished - Apr 8 2015

Keywords

  • Stevia rebaudiana
  • [2 + 2] photocycloaddition
  • chlorogenic acids
  • cis-trans isomerization
  • tandem mass spectrometry

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