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The overlooked rotational isomerism of C-glycosyl flavonoids

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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.

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Abbreviations

HPLC:

High performance liquid chromatography

NMR:

Nuclear magnetic resonance spectroscopy

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Authors and Affiliations

  1. Guangdong Food and Drug Vocational College, No. 321 Longdong North Street, Tianhe District, Guangzhou, 510520, China

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

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  1. Guohong Zhou
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  2. Renliang Yan
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  3. Xiaogen Wang
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  4. Shaolin Li
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  5. Jin Lin
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  7. Zhendong Zhao
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Correspondence to Zhendong Zhao.

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Zhou, G., Yan, R., Wang, X. et al. The overlooked rotational isomerism of C-glycosyl flavonoids. Phytochem Rev 18, 443–461 (2019). https://doi.org/10.1007/s11101-019-09601-7

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