Flavonoid diversification in different leaf compartments of Primula auricula (Primulaceae)

Birgit Holzbach, Viktor Reuter, Markus Bacher, Johann Schinnerl, Lothar Brecker, Thomas Rosenau, Karin Valant-Vetschera*

*Corresponding author for this work

Research output: Contribution to journalArticleScientificpeer-review

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Populations of Primula auricula L. subsp. auricula from Austrian Alps were studied for flavonoid composition of both farinose exudates and tissue of leaves. The leaf exudate yielded Primula-type flavones, such as unsubstituted flavone and its derivatives, while tissue flavonoids largely consisted of flavonol 3-O-glycosides, based upon kaempferol (3, 4) and isorhamnetin (5–7). Kaempferol 3-O-(2″-O-β-xylopyranosyl-[6″-O-β-xylopyranosyl]-β-glucopyranoside) (3) and isorhamnetin 3-O-(2″-O-β-xylopyranosyl-[6″-O-β-xylopyranosyl]-β-glucopyranoside) (6) are newly reported as natural compounds. Remarkably, two Primula type flavones were also detected in tissues, namely 3′-hydroxyflavone 3′-O-β-glucoside (1) and 3′,4′-dihydroxyflavone 4′-O-β-glucoside (2), of which (1) is reported here for the first time as natural product. All structures were unambiguously identified by NMR and MS data. Earlier reports on the occurrence of 7,2′-dihydroxyflavone 7-O-glucoside (macrophylloside) in this species could not be confirmed. This structure was now shown to correspond to 3′,4′-dihydroxyflavone 4′-O-glucoside (2) by comparison of NMR data. Observed exudate variations might be specific for geographically separated populations. The structural diversification between tissue and exudate flavonoids is assumed to be indicative for different ecological roles in planta.

Original languageEnglish
Article number104310
JournalBiochemical Systematics and Ecology
Publication statusPublished - Oct 2021
MoE publication typeA1 Journal article-refereed


  • Exudate flavonoids
  • Flavonoid glycosides
  • Organ specific diversification
  • Primula auricula


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