胭脂萝卜酰化花色苷的吸附纯化行为及其体外抗脂肪酶活性

doi:10.3864/j.issn.0578-1752.2026.17.013

Abstract

Abstract:

【Objective】Anthocyanins of red radish (ARR) are natural red pigments characterized by strong processing stability and diverse physiological activities. This study aimed to optimize the purification process of ARR and systematically elucidate its inhibitory mechanism against pancreatic lipase, thereby providing a theoretical foundation for the development of functional foods targeting hyperlipidemia.【Method】The adsorption and desorption properties of six macroporous resins with different polarities on ARR were evaluated to select the optimal resin. The kinetic and thermodynamic characteristics of resin adsorbing ARR, as well as dynamic desorption characteristics at different ethanol concentrations, were investigated. Individual anthocyanins were identified by ultra-high performance liquid chromatography coupled with triple quadrupole mass spectrometry, and the purification performance of dextran gel chromatography was also assessed. Furthermore, the inhibitory activity and inhibition type of ARR against pancreatic lipase were evaluated in vitro, while the molecular interaction mechanism was explored using Fourier transform infrared spectroscopy and molecular dynamics simulations.【Result】The non-polar macroporous resin X-5 exhibited the highest recovery rate of ARR (81.17%) following sequential adsorption and desorption. The adsorption process followed pseudo-first-order kinetics and the Temkin isotherm model, indicating a spontaneous endothermic reaction with a maximum equilibrium adsorption capacity of 10.55 mg·g^-1 at 35 ℃. Ethanol (40%) was identified as the optimal desorption agent. Purification using X-5 resin alone yielded higher purity than the combined application of X-5 and dextran gel. A total of 22 anthocyanins were identified, including 15 polyacetylated, 4 monooacylated, and 3 common anthocyanins. The main components (58.14%) were pelargonidin-3-(feruloyl) diglucoside-5-(malonyl) glucoside, pelargonidin-3-(caffeoyl) diglucoside-5-(malonyl) glucoside, pelargonidin-3-(feruloyl) diglucoside-5-glucoside, and pelargonidin-3-(caffeoyl) diglucoside-5-glucoside. ARR functioned as a reversible and mixed-type inhibitor of pancreatic lipase with an IC₅₀ of 3.01 mg·mL^-1. ARR interacts with active site residues of pancreatic lipase (Phe77, His263, and Ser152) via hydrophobic, hydrogen bonding, and electrostatic interactions, inducing conformational changes in the secondary structure and inhibiting its activity.【Conclusion】High-purity ARR, efficiently prepared using X-5 macroporous resin, exerted a reversible mixed-type inhibitory effect on pancreatic lipase, mediated predominantly by hydrophobic and hydrogen- bonding interactions.

Key words: acylated anthocyanins, macroporous resin, adsorption, desorption, lipase inhibitory activity, red radish, molecular dynamics

LI WenFeng, HUANG ShiHan, HE LiQun, ZHANG LianNa, ZHU ChunLin, MING Jian. Adsorptive Purification Behavior of Acylated Anthocyanins from Red Radish and Its Anti-Lipase Activity in vitro[J].Scientia Agricultura Sinica, 2026, 59(17): 3890-3906.

Figures/Tables 13

Table 1

Table 2

Parameters for the determination of monomeric anthocyanin by UHPLC-QQQ-MS/MS"

简写 Abbreviation	花色苷全名 Full name of anthocyanins	母离子 [M+H]⁺	碎片离子 MS/MS (m/z)
P3CCD5MG	天竺葵素-3-(咖啡酰)(咖啡酰)二葡萄糖苷-5-(丙二酰)葡萄糖苷 Pelargonidin-3-(caffeoyl)(caffeoyl) diglucoside-5-(malonyl) glucoside	1167	919; 519; 271
P3CCD5G	天竺葵素-3-(咖啡酰)(咖啡酰)二葡萄糖苷-5-葡萄糖苷 Pelargonidin-3-(caffeoyl)(caffeoyl) diglucoside-5-glucoside	1081	919; 433; 271
P3CFD5G	天竺葵素-3-(咖啡酰)(阿魏酰)二葡萄糖苷-5-葡萄糖苷 Pelargonidin-3-(caffeoyl)(feruloyl) diglucoside-5-glucoside	1095	933; 433; 271
P3CD5MG	天竺葵素-3-(咖啡酰)二葡萄糖苷-5-(丙二酰)葡萄糖苷 Pelargonidin-3-(caffeoyl) diglucoside-5-(malonyl) glucoside	1005	757; 519; 271
P3CD5G	天竺葵素-3-(咖啡酰)二葡萄糖苷-5-葡萄糖苷 Pelargonidin-3-(caffeoyl) diglucoside-5-glucoside	919	757; 595; 271
P3FCD5MG	天竺葵素-3-(阿魏酰)(阿魏酰)二葡萄糖苷-5-(丙二酰)葡萄糖苷 Pelargonidin-3-(feruloyl)(caffeoyl) diglucoside-5-(malonyl) glucoside	1181	933; 771; 519; 271
P3FFD5MG	天竺葵素-3-(阿魏酰)(阿魏酰)二葡萄糖苷-5-(丙二酰)葡萄糖苷 Pelargonidin-3-(feruloyl)(feruloyl)diglucoside-5-(malonyl) glucoside	1195	947; 519; 271
P3FFD5G	天竺葵素-3-(阿魏酰)(阿魏酰)二葡萄糖苷-5-葡萄糖苷 Pelargonidin-3-(feruloyl)(feruloyl) diglucoside-5-glucoside	1109	947; 433; 271
P3FD5MG	天竺葵素-3-(阿魏酰)二葡萄糖苷-5-(丙二酰)葡萄糖苷 Pelargonidin-3-(feruloyl) diglucoside-5-(malonyl) glucoside	1019	771; 519; 271
P3FD5G	天竺葵素-3-(咖啡酰)二葡萄糖苷-5-葡萄糖苷 Pelargonidin-3-(feruloyl)diglucoside-5-glucoside	933	771; 433; 271
P3PCD5MG	天竺葵素-3-(对香豆酰)(咖啡酰)二葡萄糖苷-5-(丙二酰)葡萄糖苷 Pelargonidin-3-(p-coumaroyl)(caffeoyl) diglucoside-5-(malonyl) glucoside	1151	903; 519; 271
P3PCD5G	天竺葵素-3-(对香豆酰)(咖啡酰)二葡萄糖苷-5-葡萄糖苷 Pelargonidin-3-(p-coumaroyl)(caffeoyl) diglucoside-5-glucoside	1065	903; 433; 271
P3PFD5MG	天竺葵素-3-(对香豆酰)( 阿魏酰)二葡萄糖苷-5-(丙二酰)葡萄糖苷Pelargonidin-3-(p-coumaroyl)(feruloyl) diglucoside-5-(malonyl) glucoside	1165	917; 519; 271
P3PFD5G	天竺葵素-3-(对香豆酰)(咖啡酰)二葡萄糖苷-5-葡萄糖苷 Pelargonidin-3-(p-coumaroyl)(feruloyl) diglucoside-5-glucoside	1079	917; 433; 271
P3PPD5MG	天竺葵素-3-(对香豆酰)(对香豆酰)二葡萄糖苷-5-(丙二酰)葡萄糖苷 Pelargonidin-3-(p-coumaroyl)(p-coumaroyl) diglucoside-5-(malonyl) glucoside	1135	887; 519; 271
P3PPD5G	天竺葵素-3-(对香豆酰)(对香豆酰)二葡萄糖苷-5-葡萄糖苷 Pelargonidin-3-(p-coumaroyl)(p-coumaroyl) diglucoside-5-glucoside	1049	877; 433; 271
P3PD5MG	天竺葵素-3-(对香豆酰)二葡萄糖苷-5-(丙二酰)葡萄糖苷 Pelargonidin-3-(p-coumaroyl) diglucoside-5-(malonyl) glucoside	989	741; 519; 271
P3PD5G	天竺葵素-3-(对香豆酰) 二葡萄糖苷-5-葡萄糖苷 Pelargonidin-3-(p-coumaroyl) diglucoside-5-glucoside	903	741; 433; 271
P3D5MG	天竺葵素-3-二葡萄糖苷-5-(丙二酰)葡萄糖苷Pelargonidin-3-diglucoside-5-(malonyl) glucoside	843	595; 519; 271
P3D5G	天竺葵素-3-二葡萄糖苷-5-葡萄糖苷 Pelargonidin-3-diglucoside-5-glucoside	757	595; 433; 271
P3G	天竺葵素-3-葡萄糖苷 Pelargonidin-3-glucoside	433	271
P3G5G	天竺葵素-3-葡萄糖苷-5-葡萄糖苷 Pelargonidin-3-glucoside-5-glucoside	595	433; 271

Table 2

Table 3

Fig. 1

Table 4

Table 5

Fig. 2

Fig. 3

Table 6

Fig. 4

Fig. 5

Fig. 6

Table 7

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大孔树脂 Macroporous resins	极性 Polarity	颗粒直径 Particle diameter (mm)	水分含量 Water content (%)	比表面积 Specific surface area (m²·g^-1)	平均孔径 Average pore diameter (A°)	孔隙率 Porosity rate (%)
NKA-9	强极性 Strong polarity	0.3—1.25	65—75	500—550	100—120	55
DM301	半极性 Semi-polarity	0.3—1.25	65—75	500—550	100—120	55
DM130	弱极性 Weak polarity	0.3—1.25	65—75	500—550	90—100	55
AB-8	弱极性 Weak polarity	0.3—1.25	65—75	480—520	130—140	46
X-5	非极性 Non-polarity	0.3—1.25	65—75	500—550	55—75	55
D101	非极性 Non-polarity	0.3—1.25	70.5	550—600	90—100	44

大孔树脂 Macroporous resin	吸附能力 Adsorption capacity (mg·g^-1)	吸附率 Adsorption ratio (%)	解吸能力 Desorption capacity (mg·g^-1)	解吸率 Desorption ratio (%)	回收率 Recovery ratio (%)
NKA-8	5.27±0.31b	85.28±0.23d	2.98±0.66b	71.59±18.43a	61.03±15.55b
DM301	5.73±0.37ab	90.91±0.51b	3.11±0.27b	69.67±7.72b	63.31±6.70b
DM130	5.53±0.32ab	88.50±1.24c	3.24±0.59ab	73.94±10.36a	65.40±8.72ab
AB-8	5.80±0.32ab	91.79±1.19ab	3.59±0.21ab	78.93±5.29a	72.49±5.60ab
X-5	5.88±0.35a	92.79±0.19a	4.05±0.19a	87.49±7.18a	81.17±6.51a
D101	5.90±0.29a	93.00±0.82a	3.83±0.79ab	82.11±13.24a	76.34±12.21ab

温度 Temperature (℃)	模型 Model
	In-particle diffusion (IPD)	Pseudo-second-order kinetic (PSOK)	Pseudo-first-order kinetic (PFOK)
	R²	R²	R²	方程 Equation	K₁ (g·mg^-1·min^-1)	Qe (mg·g·resins^-1)
25	0.8262	0.9737	0.9991	y=0.0954x+0.2832	0.032	10.48
35	0.6750	0.9452	0.9997	y=0.0948x+0.1467	0.061	10.55
45	0.3918	0.7546	0.9995	y=0.0987x+0.0544	0.179	10.13

温度 Temperature (℃)	模型 Model
	Freundlich	Langmuir	Temkin
	R²	R²	R²	方程 Equation	K_T (L·mg^-1)	B_T (J·mol^-1)
25	0.8786	0.4421	0.9181	Qe=0.0047lnCe+0.0128	15.23	0.0047
35	0.7865	0.3200	0.9742	Qe=0.0055lnCe+0.0158	17.69	0.0055
45	0.7535	0.3427	0.9970	Qe=0.0099lnCe+0.0285	17.79	0.0099

花色苷名称 Name of anthocyanins	粗提物 Crude extract	X-5纯化 Purified by X-5	X-5和葡聚糖凝胶纯化 Purified by X-5 and dextran gel
P3FD5MG	139.42±11.14	121.98±1.05	76.47±2.95**#
P3CD5MG	71.98±0.73	58.71±1.72**	21.28±1.29**#
P3FD5G	59.13±5.76	65.52±4.75	19.64±1.25**#
P3CD5G	45.81±2.68	56.32±1.67**	6.21±0.31**#
P3FFD5MG	37.62±0.71	30.50±1.31**	11.54±0.38**#
P3PD5MG	33.25±1.31	31.83±0.53	21.68±1.57**#
P3PD5G	26.51±0.43	37.08±2.49**	9.08±0.95**#
P3D5G	26.9±4.34	30.54±3.35	13.53±1.30**#
P3D5MG	12.6±0.55	12.15±0.10	3.92±0.23**#
P3CCD5MG	9.52±0.48	7.35±0.12**	3.08±0.17**#
P3PFD5MG	9.88±0.44	9.94±0.27	4.66±0.21**#
P3FCD5MG	9.49±0.10	9.50±0.83	4.51±0.31**#
P3CFD5G	5.47±0.63	16.44±0.8**	2.03±0.15**#
P3FFD5G	4.25±0.03	7.35±0.67**	1.81±0.14**#
P3PCD5MG	3.90±0.25	3.37±0.03*	2.18±0.06**#
P3CCD5G	2.09±0.21	10.77±0.35**	1.26±0.02**#
P3PFD5G	1.73±0.08	4.00±0.13**	0.95±0.03**#
P3PCD5G	1.07±0.11	3.18±0.09**	0.70±0.03**#
P3PPD5MG	1.11±0.04	1.02±0.04*	0.81±0.02**#
P3G5G	0.73±0.12	1.20±0.15*	0.44±0.04*#
P3G	0.62±0.04	0.71±0.06	0.42±0.00**#
P3PPD5G	0.58±0.03	0.90±0.09**	0.46±0.03**#
多酰化花色苷 Polyacylated anthocyanins	331.34±11.70	316.82±1.28	153.42±1.41**#
单酰化花色苷 Monoacylated anthocyanins	144.06±5.87	171.08±8.25**	38.85±2.08**#
非酰化花色苷 Non-acetylated anthocyanins	28.25±4.27	32.45±3.52	14.38±1.28**#
花色苷总量 Total anthocyanin content	503.65±10.58	520.35±6.73	206.65±2.22**#

Adsorptive Purification Behavior of Acylated Anthocyanins from Red Radish and Its Anti-Lipase Activity in vitro

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能量 Energy (kJ·mol^-1)	花色苷Anthocyanin
能量 Energy (kJ·mol^-1)	P3FD5MG	P3FD5G	P3CD5MG	P3CD5G
范德华能 van der Waal energy	4327.38±101.75	-281.45±17.18	-276.44±29.15	-235.08±29.81
静电能 Electrostattic energy	-269.99±33.29	-302.10±21.13	-332.55±32.62	-246.73±31.25
极性溶剂化能 Polar solvation energy	268.80±38.32	268.30±21.33	336.19±44.01	209.25±37.31
溶剂可及表面积能 Solvent-accessible surface area energy	-32.57±1.98	-29.33±1.80	-32.22±2.39	-27.02±3.28
结合能 Binding energy	4293.61±99.79	-344.58±21.30	-305.03±29.25	-299.58±26.78

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