The overlooked rotational isomerism of C-glycosyl flavonoids View Full Text


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Article Info

DATE

2019-03-09

AUTHORS

Guohong Zhou, Renliang Yan, Xiaogen Wang, Shaolin Li, Jin Lin, Jia Liu, Zhendong Zhao

ABSTRACT

C-glycosyl flavonoids are important secondary plant metabolites with a wide range of biological activities. Rotational isomerism, arising from restricted bond rotation, has been observed on a portion of C-glycosyl flavonoids. NMR technique contributes most to the observation and research of this phenomenon. Signal duplication in NMR spectra may be the key characteristic of C-glycosyl flavonoids existing as rotamers. Bulky steric hindrance from the substituents at position 7 and sugar moieties are responsible for the restricted bond rotation. There are other influence factors including temperature, solvents, H-bonds and π-stacking, but these are of lesser importance. Difference exists between 8-C-glycosyl flavonoids and their 6-C-glycosyl isomers despite sharing the same flavonoid aglycone and sugar moiety. 8-C-glycosyl flavonoids are more likely to suffer from restricted rotation. The energy barriers between rotamers of C-glycosyl flavonoids seem not high enough for atropisomerism to be realized and the isolation of rotamers should be difficult. More... »

PAGES

1-19

References to SciGraph publications

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    https://app.dimensions.ai/details/publication/pub.1112673497


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    curl -H 'Accept: application/ld+json' 'https://scigraph.springernature.com/pub.10.1007/s11101-019-09601-7'

    N-Triples is a line-based linked data format ideal for batch operations.

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    Turtle is a human-readable linked data format.

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    RDF/XML is a standard XML format for linked data.

    curl -H 'Accept: application/rdf+xml' 'https://scigraph.springernature.com/pub.10.1007/s11101-019-09601-7'


     

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