Effect of proanthocyanidin on the stability of Dendrobium officinale anthocyanins and its copigmentation mechanism

doi:10.3969/j.issn.1004-1524.20250272

Acta Agriculturae Zhejiangensis ›› 2026, Vol. 38 ›› Issue (3): 471-480.DOI: 10.3969/j.issn.1004-1524.20250272

• Horticultural Science • Previous Articles Next Articles

Effect of proanthocyanidin on the stability of Dendrobium officinale anthocyanins and its copigmentation mechanism

YANG Chenchen¹^,²(), TAO Wenyang², XING Jianrong², ZHOU Wanyi², WANG Mengzhu², LI Ming¹, YANG Ying²^,^*(), ZHAO Yuping¹^,^*()

^1. Huaiyin Institute of Technology, Huai’an 223001, Jiangsu, China
^2. Institute of Food Science, Zhejiang Academy of Agricultural Sciences, Hangzhou 310021, China

Received:2025-04-07 Online:2026-03-25 Published:2026-04-17
Contact: YANG Ying,ZHAO Yuping

Abstract

Abstract:

In order to enhance the stability of Dendrobium officinale anthocyanins (DOA), UV-VIS spectroscopy, Fourier transform infrared spectroscopy (FT-IR), X-ray diffraction (XRD), and molecular docking techniques were employed to investigate the effects of various copigments on DOA stability and their underlying mechanisms. The results showed that under the same temperature conditions, catechin (C), grape seed proanthocyanidins (GSPEs), and bayberry leaf proanthocyanidins (BLPEs) significantly decreased the degradation rate constant of DOA by inducing the peak shifts of hydroxyl groups and aromatic rings in DOA, thereby improving its thermal and oxidative stability. These copigments interact with DOA via hydrogen bonds and π-π stacking interactions, forming stable complexes. Notably, due to the low binding energy between the polyhydroxyl structure and DOA, BLPEs can fully encapsulate the C-ring of anthocyanins, preventing nucleophilic attacks by water molecules and thus enhancing DOA stability more effectively. This study elucidated the specific effects and mechanisms of proanthocyanidins in stabilizing DOA through copigmentation, providing a theoretical foundation for the regulation of natural pigment stability in food processing and technical support for the development of high-stability anthocyanin preparations.

Key words: Dendrobium officinale, anthocyanins, proanthocyanidins, copigment, stability

CLC Number:

TS264.4

YANG Chenchen, TAO Wenyang, XING Jianrong, ZHOU Wanyi, WANG Mengzhu, LI Ming, YANG Ying, ZHAO Yuping. Effect of proanthocyanidin on the stability of Dendrobium officinale anthocyanins and its copigmentation mechanism[J]. Acta Agriculturae Zhejiangensis, 2026, 38(3): 471-480.

Figures/Tables 5

References 26

[1]	SADOWSKA-BARTOSZ I, BARTOSZ G. Antioxidant activity of anthocyanins and anthocyanidins: a critical review[J]. International Journal of Molecular Sciences, 2024, 25(22): 12001.
[2]	LI F, LI H J, LI S B, et al. A review of Lycium ruthenicum Murray: geographic distribution tracing, bioactive components, and functional properties[J]. Heliyon, 2024, 10(21): e39566.
[3]	ENARU B, DRECANU G, POP T D, et al. Anthocyanins: factors affecting their stability and degradation[J]. Antioxidants, 2021, 10(12): 1967.
[4]	FAN L L, WANG Y, XIE P J, et al. Copigmentation effects of phenolics on color enhancement and stability of blackberry wine residue anthocyanins: chromaticity, kinetics and structural simulation[J]. Food Chemistry, 2019, 275: 299-308.
[5]	TROUILLAS P, SANCHO-GARCÍA J C, DE FREITAS V, et al. Stabilizing and modulating color by copigmentation: insights from theory and experiment[J]. Chemical Reviews, 2016, 116(9): 4937-4982.
[6]	GENÇDAǦ E, ÖZDEMIR E E, DEMIRCI K, et al. Copigmentation and stabilization of anthocyanins using organic molecules and encapsulation techniques[J]. Current Plant Biology, 2022, 29: 100238.
[7]	ZHANG B, WANG Q, ZHOU P P, et al. Copigmentation evidence of oenin with phenolic compounds: a comparative study of spectrographic, thermodynamic and theoretical data[J]. Food Chemistry, 2020, 313: 126163.
[8]	YU K J, SONG Y S, LIN J X, et al. The complexities of proanthocyanidin biosynthesis and its regulation in plants[J]. Plant Communications, 2023, 4(2): 100498.
[9]	LI L Q, ZHANG Y, SUN B G, et al. The neuroprotective effects of Chinese bayberry leaves proanthocyanidins[J]. Journal of Functional Foods, 2018, 40: 554-563.
[10]	YI F X, HOU F Y, ZHAN S Q, et al. Preparation, characterization and application of pH-responsive smart film based on chitosan/zein and red radish anthocyanin[J]. International Journal of Biological Macromolecules, 2023, 253: 127037.
[11]	REN Z Y, QIU F N, WANG Y J, et al. Network analysis of transcriptome and LC-MS reveals a possible biosynthesis pathway of anthocyanins in Dendrobium officinale[J]. BioMed Research International, 2020, 2020: 6512895.
[12]	ZHANG Y, ZHOU X Z, TAO W Y, et al. Antioxidant and antiproliferative activities of proanthocyanidins from Chinese bayberry (Myrica rubra Sieb. et Zucc.) leaves[J]. Journal of Functional Foods, 2016, 27: 645-654.
[13]	HALGREN T A, NACHBAR R B. Merck molecular force field IV: conformational energies and geometries for MMFF94[J]. Journal of Computational Chemistry, 1996, 17(5/6): 587-615.
[14]	SEERAM N P, BOURQUIN L D, NAIR M G. Degradation products of cyanidin glycosides from tart cherries and their bioactivities[J]. Journal of Agricultural and Food Chemistry, 2001, 49(10): 4924-4929.
[15]	RUENROENGKLIN N, YANG B, LIN H T, et al. Degradation of anthocyanin from Litchi fruit pericarp by H₂O₂and hydroxyl radical[J]. Food Chemistry, 2009, 116(4): 995-998.
[16]	FAVARO L, BALCÃO V, ROCHA L, et al. Physicochemical characterization of a crude anthocyanin extract from the fruits of Jussara(Euterpe edulis Martius): potential for food and pharmaceutical applications[J]. Journal of the Brazilian Chemical Society, 2018, 29(10): 2072-2088.
[17]	LYU J H, LI J M, JIANG W G, et al. Copigmentation effects of different phenolics on color stability of three basic anthocyanins in wines: chromaticity, thermodynamics and molecular dynamics simulation[J]. Food Chemistry, 2025, 476: 143499.
[18]	ZHANG L L, WANG W B, YUE X Y, et al. Gallic acid as a copigment enhance anthocyanin stabilities and color characteristics in blueberry juice[J]. Journal of Food Science and Technology, 2020, 57(4): 1405-1414.
[19]	WANG J D, ZHAO Y Q, SUN B, et al. The structure of anthocyanins and the copigmentation by common micromolecular copigments: a review[J]. Food Research International, 2024, 176: 113837.
[20]	NIE M, WANG L, LU S M, et al. Protective effect of amino acids on the stability of bayberry anthocyanins and the interaction mechanism between l-methionine and cyanidin-3-O-glycoside[J]. Food Chemistry, 2022, 396: 133689.
[21]	MERCALI G D, JAESCHKE D P, TESSARO I C, et al. Degradation kinetics of anthocyanins in acerola pulp: comparison between ohmic and conventional heat treatment[J]. Food Chemistry, 2013, 136(2): 853-857.
[22]	SOUSA D, BASÍLIO N, OLIVEIRA J, et al. A new insight into the degradation of anthocyanins: reversible versus the irreversible chemical processes[J]. Journal of Agricultural and Food Chemistry, 2022, 70(2): 656-668.
[23]	MOSHFEGH N, NIAKOUSARY M, HOSSEINI S M H, et al. Effect of maltodextrin and Persian gum as wall materials and tannic acid as copigment on some properties of encapsulated sour cherry anthocyanin microcapsules[J]. Food Chemistry, 2025, 463: 141165.
[24]	SERRANO C, LAMAS B, OLIVEIRA M C, et al. Exploring the potential of anthocyanin-based edible coatings in confectionery: temperature stability, pH, and biocapacity[J]. Foods, 2024, 13(15): 2450.
[25]	CAI W H, TREFS J L, HUGEL T, et al. Anisotropy of π-π stacking as basis for superlubricity[J]. ACS Materials Letters, 2023, 5(1): 172-179.
[26]	ZHANG B, HE F, ZHOU P P, et al. Copigmentation between malvidin-3-O-glucoside and hydroxycinnamic acids in red wine model solutions: investigations with experimental and theoretical methods[J]. Food Research International, 2015, 78: 313-320.

处理 Treatment	n(DOA)∶n(辅色素) n(DOA)∶n(copigment)	D_λ_,max	ΔD_λ_,max/%	λ_max/nm	Δλ_max/nm
DOA	—	0.233±0.008 d	—	542±0 e	—
DOA-C	1∶40	0.258±0.017 bcd	22.781±0.447 e	544±0 c	2±0 c
	1∶20	0.255±0.016 bcd	20.328±0.298 f	544±1 c	2±1 c
	1∶10	0.249±0.013 bcd	16.306±0.280 h	543±0 d	1±0 d
	1∶1	0.239±0.005 cd	6.894±0.265 i	543±0 d	1±0 d
DOA-GSPEs	1∶40	0.336±0.025 a	61.512±0.488 a	545±0 b	3±0 b
	1∶20	0.266±0.021 bc	28.326±0.313 c	545±1 b	3±1 b
	1∶10	0.249±0.013 bcd	16.087±0.377 h	544±0 c	2±0 c
	1∶1	0.237±0.006 cd	4.807±0.329 j	544±1 c	2±1 c
DOA-BLPEs	1∶40	0.278±0.024 b	35.213±0.311 b	546±0 a	4±0 a
	1∶20	0.265±0.020 bc	27.614±0.294 d	546±0 a	4±0 a
	1∶10	0.253±0.015 bcd	19.262±0.355 g	545±0 b	3±0 b
	1∶1	0.239±0.005 cd	6.670±0.464 i	544±0 c	2±0 c

处理 Treatment	n(DOA)∶n(辅色素) n(DOA)∶n(copigment)	D_λ_,max	ΔD_λ_,max/%	λ_max/nm	Δλ_max/nm
DOA	—	0.233±0.008 d	—	542±0 e	—
DOA-C	1∶40	0.258±0.017 bcd	22.781±0.447 e	544±0 c	2±0 c
	1∶20	0.255±0.016 bcd	20.328±0.298 f	544±1 c	2±1 c
	1∶10	0.249±0.013 bcd	16.306±0.280 h	543±0 d	1±0 d
	1∶1	0.239±0.005 cd	6.894±0.265 i	543±0 d	1±0 d
DOA-GSPEs	1∶40	0.336±0.025 a	61.512±0.488 a	545±0 b	3±0 b
	1∶20	0.266±0.021 bc	28.326±0.313 c	545±1 b	3±1 b
	1∶10	0.249±0.013 bcd	16.087±0.377 h	544±0 c	2±0 c
	1∶1	0.237±0.006 cd	4.807±0.329 j	544±1 c	2±1 c
DOA-BLPEs	1∶40	0.278±0.024 b	35.213±0.311 b	546±0 a	4±0 a
	1∶20	0.265±0.020 bc	27.614±0.294 d	546±0 a	4±0 a
	1∶10	0.253±0.015 bcd	19.262±0.355 g	545±0 b	3±0 b
	1∶1	0.239±0.005 cd	6.670±0.464 i	544±0 c	2±0 c

处理 Treatment	E_a/(kJ·mol^-1)	R²	T/K	K/h^-1	t_1/2/h	ΔH/(kJ·mol^-1)	ΔG/(kJ·mol^-1)	ΔS/(J·mol^-1)
DOA	29.964±1.873 d	0.991	313.15	0.034±0.002 hi	20.39±1.20 fg	27.360±1.873 d	88.108±0.153 m	-193.989±6.009 d
			323.15	0.045±0.003 g	15.40±1.03 ghi	27.277±1.873 d	89.790±0.179 k	-193.447±5.825 d
			333.15	0.061±0.004 e	11.36±0.74 ijk	27.194±1.873 d	91.687±0.182 gh	-193.583±5.650 d
			343.15	0.078±0.005 c	8.89±0.57 ijk	27.111±1.873 d	93.771±0.183 d	-194.260±5.486 d
			353.15	0.098±0.006 a	7.07±0.43 k	27.028±1.873 d	95.848±0.180 a	-194.875±5.329 d
DOA-C	35.713±2.156 c	0.990	313.15	0.018±0.001 lm	38.51±2.14 c	33.109±2.156 c	87.223±0.145 n	-172.805±6.905 c
			323.15	0.024±0.002 jk	28.88±2.41 de	33.026±2.156 c	89.335±0.224 l	-174.249±6.712 c
			333.15	0.037±0.002 h	18.73±1.01 fgh	32.943±2.156 c	91.053±0.150 i	-174.426±6.500 c
			343.15	0.055±0.004 f	12.60±0.92 hijk	32.860±2.156 c	92.737±0.208 f	-174.493±6.325 c
			353.15	0.086±0.005 b	8.06±0.47 jk	32.777±2.156 c	94.180±0.171 c	-173.873±6.135 c
DOA-GSPEs	53.195±2.487 b	0.994	313.15	0.007±0.001 n	99.02±14.15 a	50.591±2.487 b	89.815±0.372 k	-125.255±8.074 b
			323.15	0.014±0.001 m	49.51±3.54 b	50.508±2.487 b	90.808±0.192 ij	-124.710±7.724 b
			333.15	0.026±0.002 jk	26.66±2.05 e	50.425±2.487 b	92.019±0.213 g	-124.849±7.508 b
			343.15	0.047±0.003 g	14.75±0.94 ghij	50.342±2.487 b	93.183±0.182 e	-124.847±7.283 b
			353.15	0.067±0.005 d	10.35±0.77 ijk	50.259±2.487 b	94.932±0.219 b	-126.499±7.093 b
DOA-BLPEs	65.058±3.012 a	0.992	313.15	0.013±0.001 m	53.32±4.10 b	62.454±3.012 a	89.933±0.200 k	-87.747±9.664 a
			323.15	0.021±0.001 kl	33.01±1.57 cd	62.371±3.012 a	90.520±0.128 j	-87.106±9.347 a
			333.15	0.029±0.002 ij	23.90±1.65 ef	62.288±3.012 a	91.450±0.191 h	-87.534±9.085 a
			343.15	0.038±0.003 h	18.24±1.44 fgh	62.205±3.012 a	92.008±0.225 g	-86.852±8.838 a
			353.15	0.049±0.004 g	14.14±1.15 ghij	62.122±3.012 a	93.621±0.240 d	-89.195±8.599 a

处理 Treatment	E_a/(kJ·mol^-1)	R²	T/K	K/h^-1	t_1/2/h	ΔH/(kJ·mol^-1)	ΔG/(kJ·mol^-1)	ΔS/(J·mol^-1)
DOA	29.964±1.873 d	0.991	313.15	0.034±0.002 hi	20.39±1.20 fg	27.360±1.873 d	88.108±0.153 m	-193.989±6.009 d
			323.15	0.045±0.003 g	15.40±1.03 ghi	27.277±1.873 d	89.790±0.179 k	-193.447±5.825 d
			333.15	0.061±0.004 e	11.36±0.74 ijk	27.194±1.873 d	91.687±0.182 gh	-193.583±5.650 d
			343.15	0.078±0.005 c	8.89±0.57 ijk	27.111±1.873 d	93.771±0.183 d	-194.260±5.486 d
			353.15	0.098±0.006 a	7.07±0.43 k	27.028±1.873 d	95.848±0.180 a	-194.875±5.329 d
DOA-C	35.713±2.156 c	0.990	313.15	0.018±0.001 lm	38.51±2.14 c	33.109±2.156 c	87.223±0.145 n	-172.805±6.905 c
			323.15	0.024±0.002 jk	28.88±2.41 de	33.026±2.156 c	89.335±0.224 l	-174.249±6.712 c
			333.15	0.037±0.002 h	18.73±1.01 fgh	32.943±2.156 c	91.053±0.150 i	-174.426±6.500 c
			343.15	0.055±0.004 f	12.60±0.92 hijk	32.860±2.156 c	92.737±0.208 f	-174.493±6.325 c
			353.15	0.086±0.005 b	8.06±0.47 jk	32.777±2.156 c	94.180±0.171 c	-173.873±6.135 c
DOA-GSPEs	53.195±2.487 b	0.994	313.15	0.007±0.001 n	99.02±14.15 a	50.591±2.487 b	89.815±0.372 k	-125.255±8.074 b
			323.15	0.014±0.001 m	49.51±3.54 b	50.508±2.487 b	90.808±0.192 ij	-124.710±7.724 b
			333.15	0.026±0.002 jk	26.66±2.05 e	50.425±2.487 b	92.019±0.213 g	-124.849±7.508 b
			343.15	0.047±0.003 g	14.75±0.94 ghij	50.342±2.487 b	93.183±0.182 e	-124.847±7.283 b
			353.15	0.067±0.005 d	10.35±0.77 ijk	50.259±2.487 b	94.932±0.219 b	-126.499±7.093 b
DOA-BLPEs	65.058±3.012 a	0.992	313.15	0.013±0.001 m	53.32±4.10 b	62.454±3.012 a	89.933±0.200 k	-87.747±9.664 a
			323.15	0.021±0.001 kl	33.01±1.57 cd	62.371±3.012 a	90.520±0.128 j	-87.106±9.347 a
			333.15	0.029±0.002 ij	23.90±1.65 ef	62.288±3.012 a	91.450±0.191 h	-87.534±9.085 a
			343.15	0.038±0.003 h	18.24±1.44 fgh	62.205±3.012 a	92.008±0.225 g	-86.852±8.838 a
			353.15	0.049±0.004 g	14.14±1.15 ghij	62.122±3.012 a	93.621±0.240 d	-89.195±8.599 a

Effect of proanthocyanidin on the stability of Dendrobium officinale anthocyanins and its copigmentation mechanism

RichHTML

PDF (PC)

Knowledge

Abstract

Cite this article

share this article

Figures/Tables 5

References 26

Related Articles 15

Recommended Articles

Metrics

Comments

[1]	CAO Yongqing, YAO Xiaohua, WANG Kailiang, REN Huadong. Interannual stability of main traits for Camellia oleifera Abel. [J]. Acta Agriculturae Zhejiangensis, 2025, 37(8): 1624-1633.
[2]	REN Jindong, CHEN Honglin, NIU Baolong, XU Xiaojun, LOU Bao. Mining new housekeeping genes of Macrobrachium rosenbergii based on transcriptome analysis [J]. Acta Agriculturae Zhejiangensis, 2025, 37(7): 1424-1429.
[3]	SUN Fengting, WANG Xu, HAN Xinyu, XU Zhenlan, WU Shenggan, HUANG Hao, TANG Tao, SHENG Qing, WANG Qiang, SHEN Guoqiang, ZHAO Xueping. Effect of sodium nitrophenolate on flavonoid content and antioxidant activity in Dendrobium officinale [J]. Acta Agriculturae Zhejiangensis, 2025, 37(4): 934-942.
[4]	QIAO Huiru, FANG Xiangjun, WU Weijie, LIU Ruiling, CHEN Hangjun, DENG Shanggui, SHA Hao, GAO Haiyan. Process optimization and quality analysis of composite lactic acid bacteria fermented beverage with blueberries and Dendrobium officinale leaves [J]. Acta Agriculturae Zhejiangensis, 2025, 37(3): 654-666.
[5]	HUANG Hao, TANG Tao, XU Zhenlan, ZHAO Xueping. Effects of pyraclostrobin on polysaccharide and flavone in Dendrobium officinale [J]. Acta Agriculturae Zhejiangensis, 2025, 37(1): 115-125.
[6]	ZHANG Ni, TAO Wenyang, LUO Mengfan, ZHOU Wanyi, ZHENG Xiaojie, LI Yanpo, JIN Huoxi, YANG Ying. Effects of enzyme-assisted extraction on composition and gut microbiota regulation function of Dendrobium officinale polysaccharide [J]. Acta Agriculturae Zhejiangensis, 2024, 36(9): 2099-2109.
[7]	ZHAO Xiaoliang, LU Yun, KANG Xingxing, LONG Zeyu, ZHENG Xiaojie. Extraction, structural characterization and antioxidant activity of polysaccharide from Dendrobium officinale in Yandang Mountain, China [J]. Acta Agriculturae Zhejiangensis, 2024, 36(8): 1898-1908.
[8]	ZHU Yan, DING Lan, CHEN Yiqian, HUANG Xiujing, JIANG Weiwei, CHEN Donghong. Identification and functional analysis of CLE gene family in Dendrobium officinale Kimura et Migo [J]. Acta Agriculturae Zhejiangensis, 2024, 36(7): 1583-1590.
[9]	WANG Xiaomei, LUO Yuqin, ZHAO Xueping, LU Lanfei, FANG Nan, WANG Xiangyun, JIANG Jinhua, HE Hongmei, ZHANG Changpeng, WANG Qiang. Residues and dietary risk assessment of fluopyram in Dendrobium officinale [J]. Acta Agriculturae Zhejiangensis, 2024, 36(7): 1666-1676.
[10]	XIONG Rui, OUYANG Ning, OU Xi, ZHONG Kangyu, ZHOU Wentao, WANG Hongrui, LONG Pan, XU Ying, FU Zhiqiang. Effect of straw returning and tillage method on soil aggregates and carbon, nitrogen content in double-season rice [J]. Acta Agriculturae Zhejiangensis, 2024, 36(6): 1347-1356.
[11]	LI Yaping, JIN Fulai, HUANG Zonggui, ZHANG Tao, DUAN Xiaojing, JIANG Wu, TAO Zhengming, CHEN Jiadong. Identification and expression pattern analysis of glycoside hydrolase GH3 gene family in Dendrobium officinale [J]. Acta Agriculturae Zhejiangensis, 2024, 36(4): 790-799.
[12]	CUI Ningbo, WANG Siman, FAN Yueyuan. Study on import stability of feed grain in China under “dual circulation” pattern [J]. Acta Agriculturae Zhejiangensis, 2024, 36(3): 681-689.
[13]	LI Jingrui, TAO Wenyang, YANG Ying, ZHOU Wanyi, LU Shengmin, WANG Yangguang. Comparative studies of polysaccharides of three Dendrobium species from Zhejiang Province and exploration of their physiological functions [J]. Acta Agriculturae Zhejiangensis, 2023, 35(8): 1888-1895.
[14]	LU Lanfei, ZHAO Xueping, MA Zheng, FANG Nan, LUO Yuqin, WANG Xiaomei, YE Hui, LEI Yuan, WANG Qiang, ZHANG Changpeng. Determination of 2, 4-epibrassinolide residues in Dendrobium officinale by solid phase extraction-high performance liquid chromatography-mass spectrometry [J]. Acta Agriculturae Zhejiangensis, 2023, 35(8): 1896-1903.
[15]	LIU Wei, TAO Jianping. How does livestock and poultry restricted zone policy affect stability of China’s hog market? [J]. Acta Agriculturae Zhejiangensis, 2023, 35(5): 1195-1210.