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Published on: August 14, 2019
Orphan flavonoids and dihydrochalcones from Primula exudates
Tshering Doma Bhutia1, Karin M Valant-Vetschera, Lothar Brecker
1Chemodiversity Research Group, Dept. of Systematic and Evolutionary Botany, Institute of Botany, University of Vienna, Rennweg 14, A-1030 Vienna, Austria. tshering.doma.bhutia@univie.ac.at
Researchers discovered two novel oxepin-containing flavonoids, Primcortusin and 3'-OH-Primcortusin, in leaf exudates of Primula cortusoides. These unique compounds, along with dihydrochalcone derivatives from P. glutinosa, expand the known chemical diversity in the Primula genus.
Area of Science:
- Phytochemistry
- Natural Product Chemistry
- Organic Chemistry
Background:
- Leaf exudates of Primula species are a source of diverse secondary metabolites.
- Previous studies have identified various flavonoids and related compounds in Primula, but oxepin-containing structures were previously unknown.
- The chemical ecology and biosynthetic pathways of Primula exudates are not fully understood.
Purpose of the Study:
- To isolate and elucidate the structures of novel compounds from the leaf exudates of Primula cortusoides and Primula glutinosa.
- To characterize the chemical constituents of leaf exudates from these two Primula species.
- To discuss the potential biosynthetic origins of the identified novel compounds and other related Primula flavones.
Main Methods:
- Isolation of compounds using chromatographic techniques.
- Structure elucidation of isolated compounds utilizing 2D Nuclear Magnetic Resonance (NMR) spectroscopy and Mass Spectrometry (MS).
- Comparative analysis of chemical profiles between P. cortusoides and P. glutinosa.
Main Results:
- Two novel orphan flavonoids, Primcortusin (1) and 3"-OH-Primcortusin (2), featuring an oxepin structure in ring A, were isolated from Primula cortusoides leaf exudates.
- Two dihydrochalcone derivatives (3,4) were identified from Primula glutinosa leaf exudates.
- These identified structures represent new chemical entities not previously reported in other Primula species.
Conclusions:
- The discovery of Primcortusin and 3"-OH-Primcortusin expands the known structural diversity of flavonoids within the Primula genus.
- The findings suggest unique biosynthetic capabilities in P. cortusoides and P. glutinosa regarding flavonoid and dihydrochalcone derivative production.
- Further research into the biosynthesis and ecological roles of these novel compounds is warranted.
