FOOD CHEMISTRY
·
2023
·
IF 8.8
Xinmiao Wang,Qian Wang,Yuanyuan Hu,Fawen Yin,Xiaoyang Liu,Dayong Zhou
The models of rat everted gut sac and hydrolysis by rat plasma were used to clarify the hydrolysis and transport characteristics of tyrosol-SCFA esters (TYr-SEs). HPLC-UV results indicated that TYr-SEs could be hydrolyzed by intestinal lipase, which showed sustained release of SCFAs and TYr. Meanwhile, TYr-SEs and the liberated SCFAs and TYr could cross the membrane and were transported into blood circulation. TYr-SEs were further hydrolyzed by carboxylesterase in plasma. Obviously, the hydrolysis of TYr-SEs in blood also showed sustained release of SCFAs and TYr. Especially, the rates of hydrolysis and transport correlated positively with the acyl chain lengths. Besides, the above rates of the TYr-SE with a straight chain were greater than those of its isomer with a branched chain. Therefore, the above-mentioned two-step release of SCFAs and TYr clearly demonstrated that TYr-SEs would be an effective approach to enhance the beneficial health effects of SCFAs and TYr.
研究领域:
营养学
·
药理学
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产品关联
DOI
PubMed
高影响因子
JOURNAL OF BIOLOGICAL INORGANIC CHEMISTRY
·
2023
·Vol. 28
·期 4
·379-391
·
IF 3
Chen Chan,Tang Weikang,Chen Qinfei,Han Mengqi,Shang Qi,Liu Wenbin
Hydroxytyrosol, one of the most powerful natural antioxidants, exhibits certificated benefits for human health. In this study, a biomimetic approach to synthesize hydroxytyrosol from the hydroxylation of tyrosol was established. EDTA-Fe 2+ coordination complex served as an active center to simulate tyrosine hydroxylase. H 2 O 2 and ascorbic acid were used as oxygen donor and hydrogen donor, respectively. Hydroxy radical and singlet oxygen contributed to active species. The biomimetic system displayed analogous component, structure, and activity with TyrH. Hydroxytyrosol titer of 21.59 mM, and productivity of 9985.92 mg·L −1 ·h −1 was achieved with 100 mM tyrosol as substrate. The proposed approach provided efficient and convenient route to quickly produce high amount of hydroxytyrosol. Graphical abstract
研究领域:
生物化学
·
合成生物学
·
抗氧化研究
✓ 已验证
DOI
高影响因子
FOOD CHEMISTRY
·
2023
·
IF 8.8
Xinmiao Wang,Qian Wang,Dong Cai,Jinghan Yu,Xiaoyang Liu,Fawen Yin,Dayong Zhou
Phenolic esters are considered as promising functional food ingredients. However, their digestion, absorption and metabolism are still unclear. Tyrosol acyl esters (TYr-Es), hydroxytyrosol acyl esters (HTy-Es) and alkyl gallates (A-GAs) were hydrolyzed by carboxylesterase in plasma and exhibited slow release of polyphenols (phenolic acids). In vitro hydrolysis degrees initially increased and then decreased with the increasing carbon chain length (C2-C16). TYr-Es exhibited higher hydrolysis degrees compared to HTy-Es, and hydrolysis degrees of TYr-Es and HTy-Es were markedly higher than those of A-GAs. Due to the fast hydrolysis rates of TYr-Es and HTy-Es, they were undetectable in all rat plasma samples collected at several times within 24 h after administration. Whereas, A-GAs could be detected in rat plasmas and three absorption peaks were found in the pharmacokinetic profiles. Importantly, the T 1/2 , MRT, AUC 0-∞ , AUC 0-t in octyl gallate group were longer (or stronger) than those in propyl gallate and dodecyl gallate groups.
研究领域:
食品科学
·
营养学
·
生物化学
✓ 已验证
产品关联
DOI
PubMed
高影响因子
Scientific Reports
·
2014
·Vol. 4
·期 1
·1-8
·
IF 5.078
Bai Yanfen,Bi Huiping,Zhuang Yibin,Liu Chang,Cai Tao,Liu Xiaonan,Zhang Xueli,Liu Tao,Ma Yanhe
Salidroside (1) is the most important bioactive component of Rhodiola (also called as “Tibetan Ginseng”), which is a valuable medicinal herb exhibiting several adaptogenic properties. Due to the inefficiency of plant extraction and chemical synthesis, the supply of salidroside (1) is currently limited. Herein, we achieved unprecedented biosynthesis of salidroside (1) from glucose in a microorganism. First, the pyruvate decarboxylase ARO10 and endogenous alcohol dehydrogenases were recruited to convert 4-hydroxyphenylpyruvate (2), an intermediate of L -tyrosine pathway, to tyrosol (3) in Escherichia coli . Subsequently, tyrosol production was improved by overexpressing the pathway genes and by eliminating competing pathways and feedback inhibition. Finally, by introducing Rhodiola -derived glycosyltransferase UGT73B6 into the above-mentioned recombinant strain, salidroside (1) was produced with a titer of 56.9 mg/L. Interestingly, the Rhodiola -derived glycosyltransferase, UGT73B6, also catalyzed the attachment of glucose to the phenol position of tyrosol (3) to form icariside D2 (4), which was not reported in any previous literatures.
研究领域:
生物化学
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合成生物学
·
微生物学
✓ 已验证
DOI
PubMed
高影响因子
MOLECULES
·
2017
·Vol. 22
·期 6
·870
·
IF 2.861
Jiao-Jiao Yuan,Frank G.F. Qin,Jun-Ling Tu,Bing Li
Due to the multiple hydroxyl groups in its structure, hydroxytyrosol (HT) is very sensitive to air and light and has very strong instability and hydrophilicity that affect its biological activity. This study attempted to prepare liposomes containing water-soluble HT to improve the bioavailability and biocompatibility of the target drug. The preparation process factors (temperature, mass ratio of phospholipid (PL) and cholesterol (CH), Tween-80 volume, HT mass) were studied and response surface methodology (RSM) was applied to optimize the conditions. The results demonstrated that by using a temperature of 63 °C, mass ratio of PL and CH 4.5:1, HT mass 5 mg and Tween-80 volume of 6 mL, HT liposomes with an encapsulation efficiency (EE) of 45.08% were prepared. It was found that the particle sizes of the HT liposomes were well distributed in the range of 100–400 nm. Compared to free HT, prepared HT liposomes had better stability and a distinct slow release effect in vitro. Besides, HT liposomes presented better DPPH radical scavenging activity than free HT, which could be due to the fact that HT was encapsulated fully inside the liposomes. In addition, the encapsulation mechanism of HT was evaluated. In summary, the results indicated that HT liposome could enhance the antioxidant activity and was a promising formulation for prolonging the biological activity time of the target drug.Keywords:hydroxytyrosol;liposomes;preparation;slow release;antioxidant activity
研究领域:
药剂学
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食品科学
·
生物化学
✓ 已验证
产品关联
DOI
PubMed
高影响因子
PROCESS BIOCHEMISTRY
·
2023
·
IF 4.4
Chenchen Zhao,Yu Sha,Wei Zhuang,Yuan Rao,Jihang Zhang,Jinglan Wu,Tao Shen,Zhuotao Tan,Chenjie Zhu,Hongman Zhang,Hanjie Ying
Hydroxytyrosol (HT) is a novel functional pharmaceutical or food ingredient that can be prepared using tyrosinase (TYR) as the catalyst. In this study, cross-linked agarose resin (AG-NTA-Ni 2+ ) was selected as the carrier for the one-step immobilization and purification of the enzyme via specific adsorption of the His-tag on the protein and metal ions on the carrier particles. The immobilized TYR exhibited excellent thermal and pH stabilities and retained 82.3% of its relative activity after seven cycles. Using different reduction methods, immobilized TYR was used as a catalyst to synthesize HT via the controlled oxidation of tyrosol. The enzymatic cascade reaction of co-immobilized TYR and glucose dehydrogenase (GDH) as a biocatalyst served as a bioreduction method with an HT yield of 88%. For the chemical reduction using ascorbic acid (AA) as the reducing agent, an 80% HT yield was achieved. These results indicate that the immobilization method, which relies on the specific coordination between transition metal ions and certain protein amino acids , is a potential strategy for the effective co-immobilization of TYR and GDH. The proposed affinity co-immobilization technique is among the potential strategies for the efficient production of HT.
研究领域:
生物技术
·
酶学
·
药学
·
食品科学
✓ 已验证
产品关联
DOI
高影响因子
BIOCATALYSIS AND BIOTRANSFORMATION
·
2024
·
IF 1.4
Guo-Bin Liang,Cheng Yang,Kang-Hong Wang,Shuangfei Li,Zhen Yang
As a new generation of water-immiscible solvents, hydrophobic deep eutectic solvents (HDESs) have shown great potential as green and sustainable reaction media for biocatalytic applications. Tyrosol is a major phenolic compound present in olive oil and wine with potential pharmacological benefits due to its strong antioxidant properties, and its application can be highly extended by increasing its lipophilicity through esterification. In this study, two lipases, one from Aspergillus oryzae (AOL) and another from Pseudomonas fluorescens (PFL), were immobilized on inorganic salt crystals (i.e. @Cu3(PO4)2) and on metal-organic frameworks (i.e. @HKUST-1). The structural features of these four new biocatalysts were characterized and their activity and stability assayed. They were successfully employed to catalyze the esterification of tyrosol to produce tyrosol esters in HDESs with excellent yields, which are comparable to, or even better than, the results obtained by using the most commonly used commercial lipase (i.e. Novozym 435 from Novozymes). The carboxylic acid-based HDESs provide not only a reaction medium but also an acylating agent for the enzymatic (trans)esterification reactions.
研究领域:
生物化学
·
绿色化学
·
酶工程
✓ 已验证
DOI
高影响因子
BIOTECHNOLOGY AND BIOENGINEERING
·
2020
·Vol. 117
·期 8
·2410-2419
·
IF 4.002
Wei Guo,Qiulan Huang,Yuhui Feng,Taicong Tan,Suhao Niu,Shaoli Hou,Zhigang Chen,Zhi-Qiang Du,Yu Shen,Xu Fang
Metabolic engineering of Saccharomyces cerevisiae for high-level production of aromatic chemicals has received increasing attention in recent years. Tyrosol production from glucose by S. cerevisiae is considered an environmentally sustainable and safe approach. However, the production of tyrosol and salidroside by engineered S. cerevisiae has been reported to be lower than 2 g/L to date. In this study, S. cerevisiae was engineered with a push-pull-restrain strategy to efficiently produce tyrosol and salidroside from glucose. The biosynthetic pathways of ethanol, phenylalanine, and tryptophan were restrained by disrupting PDC1 , PHA2 , and TRP3 . Subsequently, tyrosol biosynthesis was enhanced with a metabolic pull strategy of introducing PcAAS and EcTyrA M53I/A354V . Moreover, a metabolic push strategy was implemented with the heterologous expression of phosphoketolase (Xfpk), and then erythrose 4-phosphate was synthesized simultaneously by two pathways, the Xfpk-based pathway and the pentose phosphate pathway, in S. cerevisiae . Furthermore, the heterologous expression of Xfpk alone in S. cerevisiae efficiently improved tyrosol production compared with the coexpression of Xfpk and phosphotransacetylase. Finally, the tyrosol yield increased by approximately 135-folds, compared with that of parent strain. The total amount of tyrosol and salidroside with glucose fed-batch fermentation was over 10 g/L and reached levels suitable for large-scale production.
研究领域:
生物技术
·
代谢工程
✓ 已验证
DOI
PubMed
高影响因子
BIOCATALYSIS AND BIOTRANSFORMATION
·
2024
·
IF 1.4
Kang-Hong Wang,Shuangfei Li,Ying-Fen Meng,Yong Zou,Guo-Bin Liang,Cheng Yang,Zhen Yang
Tyrosol is a principle phenolic compound present in olive oil and wine with great pharmacological potentials due to its strong antioxidant property. Its application can be highly extended by increasing its lipophilicity through esterification. In this study, tyrosol esters were synthesized by enzymatic transesterification of tyrosol with vinyl esters, with a commercial lipase from Novozymes (Novozym 435, Candida antarctica lipase B (CALB) immobilized on macroporous acrylic resin beads) as the catalyst, both in organic solvents and in ionic liquids. Methyl tert-butyl ether (MTBE) was the best solvent, offering complete conversions towards the synthesis of tyrosol esters with varying chain lengths (C2-C18) within 1 h. Taking the enzymatic transesterification between tyrosol and vinyl acetate as the model reaction, 18 organic solvents and 24 ionic liquids were screened, and their solvent properties (i.e. hydrophobicity, polarity, viscosity, water activity, and partition coefficients of substrate and product) were correlated to the enzyme activity. Upon enzyme screening, four new lipases were found to be highly efficient, relative to the best-performed Novozym 435 and Lipozyme TLIM (Thermomyces lanuginosus lipase (TLL) immobilized on silica gel), in tyrosol ester synthesis. This work provides enzymatic methods of esterifying tyrosol that are much more efficient than those reported in literature, and will shed light on re-consideration of the roles of solvents in nonaqueous enzymology.
研究领域:
生物化学
·
酶工程
✓ 已验证
产品关联
DOI
高影响因子
INTERNATIONAL JOURNAL OF BIOLOGICAL MACROMOLECULES
·
2024
·
IF 7.7
Guosi Li,Wei Wang,Heng Guo,Shanyong Yi,Fang Wang,Shiping Huang,Nan Hu,Qilin Xu,Yongjun Zang,Bangxing Han,Xinjian Yin
Microbial glycosyltransferases efficiently synthesize glucosides and have garnered increasing interest. However, limited regioselectivity has impeded their broad application, particularly in the pharmaceutical industry. In this study, the UDP-glycosyltransferase YjiC from Bacillus licheniformis ( Bl YjiC) was engineered to achieve the bidirectional regioselective glycosylation of tyrosol and its derivatives. Initially, site-directed saturation mutagenesis was performed on two newly identified substrate-binding cavities in the acceptor pocket of Bl YjiC to provide a comprehensive blueprint of the interplay between mutations and function (mutability landscape). Iterative saturation mutagenesis was performed, guided by the mutability landscape. Two highly regioselective mutants M6 (M112L/I325Y/L70R/Q136E/I67E/M77R) and M2’ (M112D/I62L) were generated, exhibiting >99 % regioselectivity toward the alcoholic and phenolic hydroxyl of tyrosol, respectively, compared with the wild-type (product mixture: 51:49 %). Both mutants exhibited excellent regioselectivity toward several dihydroxy phenolic substrates, offering valuable biocatalysts for the regioselective synthesis of glucosides. Their application was confirmed in a short synthesis of salidroside (3.6 g/L) and icariside D2 (2.4 g/L), which exhibited near-perfect regioselectivity. This study provides valuable insights into future protein engineering of similar enzymes and opens new avenues for their practical applications.
研究领域:
生物化学
·
合成生物学
·
制药工程
✓ 已验证
产品关联
DOI
PubMed
高影响因子
FOOD CHEMISTRY
·
2024
·
IF 8.5
Yexuan Yao,Li Ma,Chengwei Yu,Ce Cheng,Hongxia Gao,Teng Wei,Litong Li,Zhiyue Wang,Wei Liu,Zeyuan Deng,Liqiang Zou,Ting Luo
To improve the poor water solubility and oral bioavailability of tyrosol, novel tyrosol liposomes (Tyr-LPs) were prepared by pH-driven method. Fourier transform infrared (FTIR) absorption spectra and X-ray diffraction (XRD) analysis indicated that Tyr-LPs were successfully encapsulated and tyrosol was in an amorphous state in liposomes. When tyrosol content in Tyr-LP was 1.33 mg/ml and the Tyr:LP (mass ratio) = 1:2, favorable dispersibility of Tyr-LP was exhibited, with an instability index of 0.049 ± 0.004, PDI of 0.274 ± 0.003, and the EE of 94.8 ± 2.5 %. In vivo pharmacokinetic studies showed that after oral administration of tyrosol or Tyr-LP (Tyr:LP = 1:2), concentration-versus-time curve (AUC 0–720mins ) and maximum concentration (C max ) values of Tyr-LP was respectively 1.5-fold ( P < 0.01) and 2.25-fold ( P < 0.01) higher than tyrosol, which indicated that the oral bioavailability of tyrosol was effectively improved in Tyr-LPs. Our study thereby provides theoretical support for the application of Tyr-LP for optimal delivery of tryosol.
研究领域:
药剂学
·
药理学
✓ 已验证
产品关联
DOI
PubMed
高影响因子
FOOD CHEMISTRY
·
2020
·
IF 6.306
Yang Zhao,Ze-Hua Huang,Hui-Ming Zhou,Ke-Xue Zhu,Xiao-Na Guo,Wei Peng
Hexose oxidase was a feasible prevention for the dark spots in the fresh wet noodle sheets (FWNS). The chemical mechanism that hexose oxidase recucing the melanins of dark spots was discussed basis on the UPLC-TOF-MS analysis of the polyphenol oxidase (PPO)-catechol system. In the process of PPO browning, hexose oxidase catalyzed the oxidation of o -benzoquinone derivatives and their oligomers, hindering the formation of melanins. Hexose oxidase was efficient in FWNS with low ash content when water addition was 24%~44% or pH range was 4 ~ 7.5. Hexose oxidase could inhubit dark spots in the presence of 10 metal ions. The recommended addition amount was 40 ~ 60 ppm, by which the dark spots could be compolitely inhibited. Hexose oxidase was also suitable for wholewheat and oat FWNS, Δ L 6d of wholewheat and oat FWNS were reduced by 4 and 7.98, respectively.
研究领域:
食品科学
·
生物化学
✓ 已验证
产品关联
DOI
PubMed
高影响因子
危险品化学品经营许可证（带存储）