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Structure–activity relationships of anthocyanidin glycosylation

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Abstract

This paper summarizes the main achievements about the structure–activity relationships of anthocyanidin glycosylation. Anthocyanidin glycosylation is the essential step of anthocyanin biosynthesis and also the prerequisite of the further modifications of anthocyanins, which is jointly characterized by the glycosylation site, the type and number of the glycosyl as well as the glycosidic bond type. It generally enhances the stability, results in the hypsochromic effect and blueing, decreases the bioavailability and anticancer activity, and decreases, increases, or does not change the antioxidant activity of the anthocyanidins or anthocyanins, which is synergetically determined by the glycosylation site and the type and number of the glycosyl. Thereinto, in nature, the blue hues caused by the glycosylation may also be reinforced by the formation of the anthocyanic vacuolar inclusions. This review could provide a reference for the research of the structure-optimizing and function-exploiting of anthocyanins.

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Abbreviations

AVI:

Anthocyanic vacuolar inclusions

COX:

Cyclooxygenase

Cy:

Cyanidin

Dp:

Delphinidin

DPPH:

2,2-Diphenyl-1-picrylhydrazil

FRAP:

Ferric reducing antioxidant potential

HCT:

Human colon tumor

LDL:

Low density lipoprotein

LOX:

Lipoxygenase

MeLo:

Methyl linoleate

Mv:

Malvidin

–OH:

Hydroxyl

ONOO–:

Peroxynitrite anion

ORAC:

Oxygen radical absorbance capacity

Pg:

Pelargonidin

\(\hbox {pK}_\mathrm{H}\) :

Hydration constant

Pn:

Peonidin

Pt:

Petunidin

SAR:

Structure–activity relationship

t-BuOOH:

Tert-butyl hydroperoxide

TEAC:

Trolox- equivalent antioxidant capacity

VDT:

Visual detection threshold

VEGF:

Vascular endothelial growth

VEGFR:

Vascular endothelial growth receptor

\(\varepsilon \) :

Molar extinction coefficient

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Acknowledgments

This work was financially supported by the National Natural Science Foundation of China: (i) “Accumulation of Radix notoginseng et Rhizoma optimized by anthocyanin biosynthesis and its mechanism (No. 31060045)”. (ii) “Ecophysiological effects of Panax notoginsing anthocyanins on P. notoginsing (No. 31260091)”.

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Authors and Affiliations

  1. College of Agronomy and Biotechnology, Yunnan Agricultural University, Kunming, 650201, China

    Chang Ling Zhao & Xue Song Bai

  2. Miaoxiang Sanqi Industrial Corporation Ltd. of Wenshan City, Wenshan, 663000, China

    Zhong Jian Chen, Ting Ju Long, Fu Gang Wei & Kang Ru Miao

  3. Sanqi Research Institute, Wenshan University, Wenshan, 663000, China

    Zhong Jian Chen

  4. College of Tobacco Sciences, Yunnan Agricultural University, Kunming, 650201, China

    Can Ding

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  1. Chang Ling Zhao
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  2. Zhong Jian Chen
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  3. Xue Song Bai
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  4. Can Ding
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  5. Ting Ju Long
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  6. Fu Gang Wei
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  7. Kang Ru Miao
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Correspondence to Chang Ling Zhao.

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Zhao, C.L., Chen, Z.J., Bai, X.S. et al. Structure–activity relationships of anthocyanidin glycosylation. Mol Divers 18, 687–700 (2014). https://doi.org/10.1007/s11030-014-9520-z

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  • DOI: https://doi.org/10.1007/s11030-014-9520-z

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