JOURNAL OF THE SCIENCE OF FOOD AND AGRICULTURE
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2021
·Vol. 102
·期 7
·2651-2659
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IF 3.639
Tongtong Zhang,Khaing zar Myint,Yongmei Xia,Jing Wu
BACKGROUND Rebaudioside A (RA) and its monoglucosyl derivative, as like rebaudioside D (RD) are the most popular stevia glycosides but possess poor solubility in water, which limited their application as edible surfactants, the applications as in micellar solubilization and drug delivery. Meanwhile, effect of the monoglucosyl attached to RA moiety remains unclear. RESULTS Monoglucosyl rebaudioside A (RAG1) was synthesized via hydrolyzing the transglycosylation product of RA with 95% of RA converted. RAG1 content in raw reaction mixture was as high as 69.5% of total glycosides, and harvested with a content of 88.2% by simple filtration. The RAG1 exhibited an aqueous solubility of 87 folds of RA or 391 folds of RD at 25 °C. The surface activity of RAG1 solution was higher than RA and invincible to RD. The RAG1 micelles promoted aqueous solubility of idebenone (IDE) up to 500 folds higher at 25 °C. The cumulative release rate of IDE encapsulated in RAG1 micelles was 777.5% or 456.7% higher of that of free IDE in simulated gastric/intestinal fluids in 14 h, respectively. The RAG1-IDE remained the same in 98 days at 25 °C. CONCLUSION The α-linked glucosyl to RA induced higher hydrophilicity and surface activity than that resulted by β-linked glucosyl, making RAG1 not only dramatically raise the aqueous solubility of RA, but also endow IDE folds higher in bioaccessibility, yet making the capsule stable at storage. The results would provide a new edible delivery nanocarrier for encapsulation of hydrophobic bioactive components. © 2021 Society of Chemical Industry.
研究领域:
食品科学
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药剂学
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化学工程
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DOI
PubMed
高影响因子
REPRODUCTIVE TOXICOLOGY
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2017
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IF 2.341
Jingle Jiang,Lina Qi,Quanwei Wei,Fangxiong Shi
Saccharin sodium and rebaudioside A are widely used as non-caloric sweeteners in our daily life; however, the impacts and regulatory mechanisms of such sweeteners on reproduction remain unclear. In the present study, we used rats as animal models to evaluate the effects of daily exposure to saccharin sodium and rebaudioside A on ovarian biologic functions. Weanling rats were distributed into five experimental groups receiving normal water, 1.5 or 7.5 mM saccharin sodium solution, or 0.5 or 2.5 mM rebaudioside A solution for 48 days of exposure. The results showed an increased percentage of abnormal estrous cycles, augmented number of ovarian cysts, elevated serum progesterone levels, and increased expression of steroidogenesis-related factors in saccharin sodium-treated groups. Conversely, rebaudioside A-treated groups showed decreased serum progesterone levels. Our findings suggest that saccharin sodium exerts adverse biologic effects on ovaries, and rebaudioside A is a potential steroidogenic disruptor in female rats.
研究领域:
药理学
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生殖生物学
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内分泌学
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PubMed
高影响因子
JOURNAL OF SEPARATION SCIENCE
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2022
·Vol. 45
·期 19
·3763-3773
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IF 3.614
Nana Chen,Mingli Huang,Qiaoge Fu,Chaoyi Shi,Ruili Guo
The separation and removal of stevioside from natural product steviol glycosides to obtain high-purity rebaudioside A is of great significance for the application of steviol glycosides in food, medicine, and other fields. Here, in order to explore the adsorbent pore structure suitable for the separation of stevioside and rebaudioside A, a hierarchically porous amino-functionalized metal–organic framework (HP-NH 2 -MIL-53) with an appropriate and narrow pore size distribution was prepared using a modulator-induced defect-formation strategy. The results showed that the hierarchically porous structure with micropores and mesopores increased the specific surface area and exposed amino groups compared with original metal organic framework (NH 2 -MIL-53), and the maximum adsorption capacity of HP-NH 2 -MIL-53 for stevioside and rebaudioside A was 233.89 mg/g. The narrow pore size distribution close to 3.80 nm promoted the screening effect, resulting in a maximum adsorption selectivity of 4.13. This work proves that when the pore size of the adsorbent is between 1.41 and 3.80 nm, it has a certain pore size screening effect on stevioside and rebaudioside A, and the hierarchically porous metal-organic frameworks provide a pre-design idea of adsorbent structure for the separation of natural products with molecular weight of 800–1000 Da.
研究领域:
食品科学
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材料科学
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天然产物化学
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DOI
高影响因子
Drug Delivery and Translational Research
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2020
·Vol. 11
·期 3
·1119-1132
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IF 2.664
Li Xuefei,Fang Jingwang,Xin Meng,Li Qiqi,Wang Jun,Yang Hui,Wu Xianggen
Nimodipine (NMD), a calcium channel blocker, has demonstrated benefits in treating glaucoma. However, its ocular therapeutic application remains limited due to its poor aqueous solubility, which restrains the development of an ophthalmic formulation. Thus, the present study aimed to formulate an NMD micelle ophthalmic solution to enhance the potential of NMD in an ocular topical formulation to treat glaucoma. The NMD micelle ophthalmic solution was formulated with nanocarriers composed of rebaudioside A and d -α-tocopheryl polyethylene glycol 1000 succinate. Spherical mixed micelles were optimized and obtained at a small micelle size 13.429 ± 0.181 nm with a narrow size distribution (polydispersity index 0.166 ± 0.023) and high encapsulation efficiency rate (99.59 ± 0.09%). Compared with free NMD, NMD in micelles had much greater in vitro membrane permeability and antioxidant activity. The NMD micelle ophthalmic solution was well tolerated in rabbit eyes. It profoundly improved the in vivo intraocular permeation of NMD, and in vivo intraocular pressure reduction and improved miosis were also observed. Accordingly, this NMD micelle ophthalmic solution might be a promising ocular formulation to treat glaucoma.
研究领域:
药剂学
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眼科
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DOI
PubMed
高影响因子
JOURNAL OF AGRICULTURAL AND FOOD CHEMISTRY
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2025
·
IF 6.2
Chengzhi Liu,Mengchu Niu,Yibing Wang,Lingyi Ren,Yueyue Li,Nan Jiang,Chunxuan Wu,Niu Liu,Yanwen Zhang,Jiakang He
Mangiferin (MGF), a bioactive compound found in mangoes and their byproducts, possesses various pharmacological activities and holds potential for use in natural nutritional supplements and pharmaceuticals. However, the low solubility and poor bioavailability significantly limit its effectiveness. To address these limitations, this study employed the natural sweetener rebaudioside A (Reb A) to encapsulate MGF within self-assembled nanomicelle (SAM), resulting in the formation of nanoscale spherical particles with an encapsulation efficiency of 87.14% ± 0.56% and a drug loading capacity of 44.31% ± 0.28%. MGF-Reb A SAM improved both the water solubility and thermal stability of MGF through structural transformation from the crystalline to the amorphous form. Additionally, MGF-Reb A SAM exhibited sustained-release properties, with 92.32% of the MGF released within 12 h. The release kinetics followed a first-order model. In Caco-2 cell studies, MGF-Reb A SAM demonstrated good cellular compatibility and increased MGF permeability across intestinal epithelial cells by enhancing passive diffusion, thereby improving bioavailability. Pharmacokinetic analysis revealed that MGF-Reb A SAM increased the bioavailability of MGF 2.41-fold. In conclusion, the Reb A-based delivery system developed in this study enhances the physicochemical properties of MGF, offering a promising strategy for its future use in food supplements and pharmaceuticals.
研究领域:
药学
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食品科学
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纳米技术
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生物物理
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药理学
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DOI
PubMed
高影响因子
Antioxidants
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2021
·Vol. 10
·期 2
·262
·
IF 6.313
Pan Li,Zehua Wang,Sin Man Lam,Guanghou Shui
Non-nutritive sweeteners are widely used in food and medicines to reduce energy content without compromising flavor. Herein, we report that Rebaudioside A (Reb A), a natural, non-nutritive sweetener, can extend both the lifespan and healthspan ofC. elegans. The beneficial effects of Reb A were principally mediated via reducing the level of cellular reactive oxygen species (ROS) in response to oxidative stress and attenuating neutral lipid accumulation with aging. Transcriptomics analysis presented maximum differential expression of genes along the target of rapamycin (TOR) signaling pathway, which was further confirmed by quantitative real-time PCR (qPCR); while lipidomics uncovered concomitant reductions in the levels of phosphatidic acids (PAs), phosphatidylinositols (PIs) and lysophosphatidylcholines (LPCs) in worms treated with Reb A. Our results suggest that Reb A attenuates aging by acting as effective cellular antioxidants and also in lowering the ectopic accumulation of neutral lipids.Keywords:C. elegans;non-nutritive sweetener;rebaudioside A;aging;oxidative stress resistance;TOR;lipidomics
研究领域:
衰老
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分子生物学
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遗传学
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生物化学
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DOI
PubMed
高影响因子
Canadian Journal of Chemistry
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2020
·Vol. 98
·期 11
·
IF 1.171
Guanyu Wang,Qiaoge Fu,Ruili Guo,Zhong Wei
The boronic acid functionalization metal-organic frameworks (MOFs), as unique boronate affinity adsorbents, have desired specific molecular affinity for the separation and enrichment of cis-diol-compounds. Herein, the boronic acid functionalized Zn-based MOF adsorbent (MOF-BA) was synthesized through a simple one-step microwave method and used for the recognition and isolation of steviol glycosides (SGs). This MOF-BA exhibits the same spherical structure and isostructure with the parent framework composed only of the primitive ligand as verified by SEM and XRD characterization. It was confirmed that changing the ratio of ligands could achieve the adjustability of the boron content in the framework. At the same time, the MOF-BA-1.0 showed a suitable pore size (4.69 nm), and the presence of boric acid functional groups showed favorable selectivity for stevioside (STV). The static adsorption results showed that adsorption performances of rebaudioside A (RA) and STV from crude sugar solution (5.0 mg mL−1, pH 8) on MOF-BA-1.0 were investigated at 303 K for 15 h. The adsorption capacities for STV and RA were 42.93 mg g−1 and 22.96 mg g−1, respectively, and the adsorption selectivity (αSTV/RA) reached 4.35. The adsorption isotherm and kinetic data of MOF-BA-1.0 for RA and STV obeyed the Langmuir isotherm model and pseudo second order kinetic model, respectively. The study demonstrated that MOF-BA-1.0 adsorbent could be used as a potential adsorbent to purify the active ingredients of stevia and obtain a high concentration of RA products.
研究领域:
化学
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材料科学
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药学
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分析化学
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DOI
高影响因子
Food Chemistry-X
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2025
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IF 8.2
TingYu Tong,YuMing Shan,JianCai Zhu,YuanBin She,YunWei Niu
Fruity aroma substances hold potential for enhancing the sensory properties of non-nutritive sweeteners. This study investigated the effects of six fruit-derived aroma compounds (isoamyl isovalerate, ethyl butyrate, isoamyl butyrate, ethyl 2-methylbutyrate, linalool, and phenethyl isobutyrate) on the sweetness and bitterness of Rebaudioside A (Reb A). Sensory evaluations revealed that these compounds significantly improved sweetness perception in 0.03 % Reb A solutions, with ethyl 2-methylbutyrate (1 mg/kg) exhibiting the strongest enhancement. T-I analysis demonstrated reduced bitterness intensity and duration, particularly for phenethyl isobutyrate. Molecular simulations indicated that aroma compounds lowered the binding free energy between Reb A and the T1R2 sweet receptor, stabilizing interactions via hydrogen bonds and steric hindrance. These findings elucidate the molecular mechanisms underlying odor-induced taste enhancement, offering practical strategies for optimizing Reb A's flavor profile in sugar-reduced products.
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高影响因子
CHINESE JOURNAL OF CHEMICAL ENGINEERING
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2024
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IF 3.7
Zhenguang Liu,Zexiang Ding,Yifeng Cao,Baojian Liu,Qiwei Yang,Zhiguo Zhang,Qilong Ren,Zongbi Bao
The equilibrium solubility of Rebaudioside A (Reb A) Form II in binary mixtures of methanol/ethanol and ethyl acetate was quantitatively determined within the temperature range of 283.15 to 328.15 K at ambient pressure. The experimental findings indicate a positive correlation between the solubility of Reb A (Form II) and both the temperature and the methanol/ethanol content in the solvent system. To describe the solubility data, six distinct models were employed: the modified Apelblat equation, the λh model, the CNIBS/R-K model, the van't Hoff-Jouyban-Acree (VJA) model, the Apelblat-Jouyban-Acree (AJA) model, and the Non-Random Two-Liquid (NRTL) model. The CNIBS/R-K model exhibited the most precise fit for solubility in methanol+ethyl acetate mixtures, reflected by an Average Relative Deviation (ARD) of 0.0011 and a Root Mean Square Deviation (RMSD) of 0.0000012. Conversely, for ethanol+ethyl acetate mixtures, the modified Apelblat equation provided a superior correlation (ARD=0.0014, RMSD=0.0000004). Furthermore, thermodynamic parameters associated with the dissolution of Reb A (Form II), including enthalpy, entropy, and the Gibbs energy change, were inferred from the data. The findings underscore that the dissolution process is predominantly endothermic across the solvent systems examined. Notably, the entropy changes appear to have a significant influence on the Gibbs free energy associated with the dissolution of Reb A (Form II), suggesting that entropic factors may play a pivotal role in the studied systems.
研究领域:
化学工程
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物理化学
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热力学
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DOI
高影响因子
EUROPEAN JOURNAL OF PHARMACOLOGY
·
2018
·
IF 3.04
Yuxin Wang,Linyao Li,Yawen Wang,Xiaokang Zhu,Mingdong Jiang,Erqun Song,Yang Song
A large population of drug candidates have failed “from bench to bed” due to unwanted toxicities. We intend to develop an alternative approach for drug discovery, that is, to seek candidates from “safe” compounds. Rebaudioside A (Reb-A) is an approved commercial sweetener from Stevia rebaudiana Bertoni. We found that Reb-A protects against carbon tetrachloride (CCl 4 )-induced oxidative injury in human liver hepatocellular carcinoma (HepG2) cells. Reb-A showed antioxidant activity on reducing cellular reactive oxygen species and malondialdehyde levels while increasing glutathione levels and superoxide dismutase and catalase activities. Reb-A treatment induced nuclear factor erythroid-derived 2-like 2 (Nrf2) activation and antioxidant response element activity, as well as the expression of heme oxygenase-1 (HO-1) and NAD(P)H quinone oxidoreductase 1 (NQO1). Further mechanistic studies indicated that c-Jun N-terminal kinase (JNK), extracellular signal-regulated protein kinase (ERK), mitogen-active protein kinase (MAPK) and protein kinase C epsilon (PKCε) signaling was upregulated. Thus, the present in vitro study conclusively demonstrated that Reb-A is an activator of Nrf2 and is a potential candidate hepatoprotective agent. More importantly, the present study illustrated that seeking drug candidates from “safe” compounds is a promising strategy.
研究领域:
药理学
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毒理学
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细胞生物学
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分子生物学
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药物发现
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产品关联
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PubMed
高影响因子
JOURNAL OF CHEMICAL AND ENGINEERING DATA
·
2018
·
IF 2.196
Behnaz Asadzadeh,Jialun Zhong,Weidong Yan
Solid–liquid equilibrium data of rebaudioside A (a natural sweetener) in nine pure solvents (methanol, ethanol, 1-propanol, 2-propanol, acetonitrile, 2-methoxyethanol, 2-ethoxyethanol, 2-buthoxyethanol, and ethylene glycol) and two binary mixed solvents (methanol + ethanol and 2-methoxyethanol + ethanol) were been measured by high performance liquid chromatography at temperatures ranging from (288.15 to 328.15) K and atmospheric pressure. From the experimental data, it was found that the solubility increased with the rising temperature in all studied solvents. The obtained values for the solubility of rebaudioside A in pure and mixed binary solvents were correlated with modified Apelblat and nonrandom two-liquid models. The results showed that these models can accurately correlate the solubility data obtained in this work. Furthermore, the crystal habits of rebaudioside A in selected solvents were studied.
研究领域:
食品科学
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物理化学
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DOI
高影响因子
JOURNAL OF AGRICULTURAL AND FOOD CHEMISTRY
·
2026
·
IF 6.7
Binhao Wang,Zhaoyue Fan,Jie Zhang,Ulrich Schwaneberg,Ye Ni,Ruizhi Han
Cyclodextrin glycosyltransferase (CGTase) is widely used in stevioside glycosylation, yet achieving precise regioselectivity remains a persistent challenge. Here, 200 ns molecular dynamics (MD) simulations identified residue Y260 in Paenibacillus macerans CGTase as a conformation-sensitive determinant for rebaudioside A (RebA) glycosylation. The Y260N variant achieved exclusive regioselectivity, producing only the C13-glycosylated products of RebA, although with a ∼30% reduction in conversion compared with wild-type. This high regioselectivity extended to other steviol glycosides─Reb C, D, and M─each yielding a single regioisomer. Further MD simulations indicated that conformational reorganization restricts access to O21 and stabilizes Glu258 toward O14, thereby enforcing C13-specific glycosylation. This work elucidates a mechanism for regioselective regulation in CGTase and provides a strategy for engineering other glycosylation enzymes.
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高影响因子
危险品化学品经营许可证（带存储）