Vitamin C and ursolic acid (UA) are key bioactive components in Rosa roxburghii, exhibiting synergistic functional effects, yet their molecular interaction mechanisms remain unclear.This study investigated the interaction characteristics between vitamin C and UA using Ultraviolet-visible spectroscopy (UV-Vis), Fourier transform infrared spectroscopy (FTIR), cyclic voltammetry (CV), and molecular simulations.Results showed that vitamin C significantly enhanced UA’s storage stability, reducing UA loss by 27.2% (P<0.05) compared to the control after 30 days at 35 ℃, while vitamin C stability remained unchanged (P>0.05).UV-Vis analysis revealed a redshift at 290.4 nm, indicating charge transfer complex (CTC) formation.FTIR confirmed hydrogen bonding between vitamin C’s enediol hydroxyl groups and UA’s carboxyl groups, evidenced by a blueshift in the O—H stretching vibration peak (3 434 cm-1).CV analysis demonstrated that the vitamin C-UA complex exhibited leftward shifts in oxidation peak potentials (ΔE1=0.012 V for the first peak, ΔE2=0.066 V for the second peak), suggesting enhanced electrochemical activity of UA due to hydrogen bond-mediated adsorption.Molecular simulations revealed a binding energy of -23.46 kcal/mol, with primary interaction sites at UA’s C-28 carboxyl group and vitamin C’s C-2 hydroxyl/hydroxymethyl groups.The vitamin C-UA interaction exhibited a unidirectional protective effect, hydrogen bonds selectively stabilized UA’s carboxyl groups but failed to protect vitamin C’s oxidation-prone enediol structure, leading to improved UA stability without affecting vitamin C degradation resistance.These findings advance the understanding of bioactive component interactions in Rosa roxburghii and provide theoretical insights for developing functional foods utilizing its active constituents.
ZHAO Xuhaicheng
,
DING Zhuhong
,
LI Silin
,
ZHANG Ting
,
WANG Yi
,
SONG Yuting
,
YU Yihong
. Interaction characteristics between vitamin C and ursolic acid in Rosa roxburghii[J]. Food and Fermentation Industries, 2025
, 51(21)
: 207
-214
.
DOI: 10.13995/j.cnki.11-1802/ts.043138
[1] 范晓燕, 孙彬焰, 郝东升, 等.刺梨的生物活性成分及加工利用研究进展[J].保鲜与加工, 2025, 25(1):139-147.
FAN X Y, SUN B Y, HAO D S, et al.Research progress on bioactive components and processing and utilization of Rosa roxburghii[J].Storage and Process, 2025, 25(1):139-147.
[2] 杜涛. 贵州刺梨产业全链条发展[N].中国食品报, 2024-12-24(002).
DU T.Comprehensive development of Guizhou Rosa roxburghii industry chain[N].China Food News, 2024-12-24(002).
[3] WANG J M, WANG G P, WANG X T, et al.Chemical constituents and bioactivities of Rosa roxburghii:A systematic review[J].Food Science and Technology, 2022, 42:e72722.
[4] FU M, LIU J, LI Q, et al.Synthesis of lipophilic vitamin C and evaluation of its antioxidant performance in sunflower seed oil frying[J].Food Chemistry, 2024, 460:140727.
[5] LUAN M Z, WANG H Y, WANG J Z, et al.Advances in anti-inflammatory activity, mechanism and therapeutic application of ursolic acid[J].Mini Reviews in Medicinal Chemistry, 2022, 22(3):422-436.
[6] KRASTEVA D, IVANOV Y, CHENGOLOVA Z, et al.Antimicrobial potential, antioxidant activity, and phenolic content of grape seed extracts from four grape varieties[J].Microorganisms, 2023, 11(2):395.
[7] TOFFALINI A, VIGOLO N, ROLLI N, et al.Association of low vitamin C concentrations and low consumption of fresh fruit and vegetables with cardiovascular disease in type 2 diabetes[J].BMC Nutrition, 2025, 11(1):68.
[8] 王晓霞, 马力通, 孙吉盛, 等.多光谱法和分子对接模拟法研究茶碱和胃蛋白酶的相互作用[J].光谱学与光谱分析, 2024, 44(3):714-721.
WANG X X, MA L T, SUN J S, et al.Study on the interaction between theophylline and pepsin by multispectral and molecular docking simulation[J].Spectroscopy and Spectral Analysis, 2024, 44(3):714-721.
[9] 尚永辉, 李子媛, 刘鑫雨, 等.抗坏血酸在多壁碳纳米管修饰玻碳电极上的电化学行为及其与DNA的相互作用[J].咸阳师范学院学报, 2021, 36(6):37-40;71.
SHANG Y H, LI Z Y, LIU X Y, et al.Electrochemical behavior of ascorbic acid on multi-walled nanotubes modified glassy carbon electrode and the intercation asarbic acid with DNA[J].Journal of Xianyang Normal University, 2021, 36(6):37-40;71.
[10] LU T, CHEN F W.Multiwfn:A multifunctional wavefunction analyzer[J].Journal of Computational Chemistry, 2012, 33(5):580-592.
[11] BRANDENBURG J G, BANNWARTH C, HANSEN A, et al.B97-3c:A revised low-cost variant of the B97-D density functional method[J].Journal of Chemical Physics, 2018, 148(6):064104.
[12] LEFEBVRE C, RUBEZ G, KHARTABIL H, et al.Accurately extracting the signature of intermolecular interactions present in the NCI plot of the reduced density gradient versus electron density[J].Physical Chemistry Chemical Physics, 2017, 19(27):17928-17936.
[13] LU T, CHEN Q X.Independent gradient model based on hirshfeld partition:A new method for visual study of interactions in chemical systems[J].Journal of Computational Chemistry, 2022, 43(8):539-555.
[14] 董志, 舒启江, 田爽, 等.黄芩苷与苦参碱分子间相互作用的量子化学计算与验证 [J].原子与分子物理学报, 2025(4):14-20.
DONG Z, SHU Q J, TIAN S, et al.Quantum chemical calculation and verification of the intermolecular interaction between baicalin and matrine [J].Journal of Atomic and Molecular Physics, 2025(4):14-20.
[15] EMAMIAN S, LU T, KRUSE H, et al.Exploring nature and predicting strength of hydrogen bonds:A correlation analysis between atoms-in-molecules descriptors, binding energies, and energy components of symmetry-adapted perturbation theory[J].Journal of Computational Chemistry, 2019, 40(32):2868-2881.
[16] 高莉, 任燕玲, 刘琳琳, 等.黑色素-纳米硒的制备及其性质[J].食品科学, 2023, 44(6):97-106.
GAO L, REN Y L, LIU L L, et al.Preparation and properties of melanin-nanoselenium complex[J].Food Science, 2023, 44(6):97-106.
[17] ALI H H, GHAREEB M M, AL-REMAWI M, et al.New insight into single phase formation of capric acid/menthol eutectic mixtures by Fourier-transform infrared spectroscopy and differential scanning calorimetry[J].Tropical Journal of Pharmaceutical Research, 2020, 19(2):361-369.
[18] MOTSHAKERI M, TRAVAS-SEJDIC J, PHILLIPS A R J, et al.Rapid electroanalysis of uric acid and ascorbic acid using a poly(3, 4-ethylenedioxythiophene)-modified sensor with application to milk[J].Electrochimica Acta, 2018, 265:184-193.
[19] TANG H, HU G Z, JIANG S X, et al.Selective determination of uric acid in the presence of ascorbic acid at poly(p-aminobenzene sulfonic acid)-modified glassy carbon electrode[J].Journal of Applied Electrochemistry, 2009, 39(12):2323-2328.
[20] CAI Z C, ZHU C, CHEN G Q, et al.Study on intermolecular hydrogen bond of uric acid water-clusters[J].Chemical Physics Letters, 2023, 818:140424.
