JOURNAL OF THE SCIENCE OF FOOD AND AGRICULTURE
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2017
·Vol. 98
·期 4
·1574-1583
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IF 2.463
Shanshan Yu,Yufan Zhang,Yun Ran,Wenyi Lai,Zhaoshou Ran,Jilin Xu,Chengxu Zhou,Xiaojun Yan
BACKGROUND Steryl glycosides (SGs) are sterol conjugates found in various plants, especially in those making up human diets. It has been demonstrated that SGs have potential health benefits, and they could be used as food supplements in a variety of food matrixes. Marine microalgae are a potential resource for human food and ingredients. In this study, gas chromatography–triple quadrupole mass spectrometry (GC–QQQ-MS) was used to characterize unknown SGs in eight microalgae belonging to different classes ( Isochrysis galbana 3011, Pavlova viridis , Platymonas helgolandica , Conticribra weissflogii , Thalassiosira pseudonana , Nitzschia closterium , Gymnodinium sp., and Karlodinum veneficum ). RESULTS The SGs were first extracted from lyophilized algae with chloroform–methanol, purified by solid-phase extraction and analyzed as trimethylsilyl derivatives. Nine SGs have been identified. In particular, new SGs like occelasteryl glycoside and stellasteryl glycoside were found in Gymnodinium sp., 24-methylene cholesteryl glycoside was detected in P. helgolandica , and 4,24-dimethylcholestan-3-yl glycoside was identified as the main constituent of microalga K. veneficum . The results also showed that the compositions of SGs in different microalgae varied, with a range of 5.234 to 0.036 g kg −1 , and microalga P. viridis contained the most abundant SGs. CONCLUSION GC–QQQ-MS is a powerful tool to detect SGs with different structures from a variety of microalgae. The compositions of SGs in different microalgae varied greatly. Microalgae are a good source of highly valued SGs. © 2017 Society of Chemical Industry
研究领域:
海洋生物学
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分析化学
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食品科学
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产品关联
DOI
PubMed
高影响因子
Foods
·
2022
·Vol. 11
·期 6
·882
·
IF 5.561
Liangqin Xie,Zeyuan Deng,Jie Zhang,Huanhuan Dong,Wei Wang,Banghuai Xing,Xiaoru Liu
Flavonoids are well known for their extensive health benefits. However, few studies compared the differences between flavonoid O-glycoside and C-glycoside. In this work, flavonoid O-glycoside (isoquercitrin), C-glycoside (orientin), and their aglycones (quercetin and luteolin) were chosen to compare their differences on antioxidant activities and metabolism during in vitro digestion and in vivo. In vitro digestion, the initial antioxidant activity of the two aglycones was very high; however, they both decreased more sharply than their glycosides in the intestinal phase. The glycosidic bond of flavonoid O-glycoside was broken in the gastric and intestinal stage, while the C-glycoside remained unchanged. In vivo, flavonoid O-glycoside in plasma was more elevated than C-glycoside on the antioxidant activity; however, flavonoid C-glycoside in urine was higher than O-glycoside. These results indicate that differences of flavonoid glycosides and their aglycones on antioxidant activity are closely related to their structural characteristics and metabolism in different samples. Aglycones possessed higher activity but unstable structures. On the contrary, the sugar substituents reduced the activity of flavonoids while improving their stability and helping to maintain antioxidant activities after digestion. Especially the C-glycoside was more stable because the stability of the C–C bond is higher than that of the C–O bond, which contributes to the difference between flavonoid O-glycoside and C-glycoside on the absorption and metabolism in vivo. This study provided a new perspective for comparing flavonoid O-glycoside, flavonoid C-glycoside, and their aglycones on their structure–activity relationship and metabolism.Keywords:flavonoid;O-glycoside;C-glycoside;aglycones;in vitro digestion;antioxidant activity
研究领域:
营养学
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药理学
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生物化学
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产品关联
DOI
PubMed
高影响因子
RSC Advances
·
2017
·Vol. 7
·期 34
·21028-21035
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IF 3.108
Yuyu Liu,Xiaohui Wang,Ting Mo,Yaru Yan,Yuelin Song,Yunfang Zhao,Jun Li,Shepo Shi,Xiao Liu,Pengfei Tu
Recently, owing to the important pharmaceutical properties of malonylated glycosides, their chemoenzymatic synthesis using malonyltransferase has received significant attention. In the present study, a new malonyltransferase, NbMaT1, was identified from Nicotiana benthamiana. Extensive enzymatic assays revealed its significant substrate tolerance based on HPLC-UV and HR-MS analyses. Moreover, 16 of the tested glycosides including flavone glycosides, flavonol glycosides, dihydroflavone glycosides, isoflavone glycosides, coumarin glycosides, and phenylethyl chromone glycosides with various sugar moieties (such as glucose, xylose, and galactose) substituted at different positions of their skeleton could be accepted by NbMaT1 to conduct the corresponding malonylation. Among these, enzymatic malonylation of phenylethyl chromone glycosides as well as xylosides and galactosides has rarely been reported earlier. Furthermore, one-pot synthesis using the known malonyl-CoA synthetase MatB and NbMaT1 as well as an unnatural fusion protein MatB–NbMaT1 was designed, which allowed malonic acid to be directly used in the malonylation reaction without the addition of expensive malonyl-CoA. Moreover, a remarkably improved conversion rate was observed for all the tested substrates, with both commercial and industrial application values. The malonylated product of the bioactive flavonoid diglycoside icariin was prepared and NMR spectroscopy revealed that the malonyl group was specifically transferred onto the 6-OH group of the glucose moiety. NbMaT1 was expected to be a universal and effective tool for chemoenzymatic synthesis of diverse bioactive-malonylated glycoside derivatives for drug discovery.
研究领域:
生物化学
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药理学
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植物生物技术
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酶学
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DOI
高影响因子
BIORESOURCE TECHNOLOGY
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2012
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IF 4.98
Zheng-Zheng Zou,Hui-Lei Yu,Chun-Xiu Li,Xin-Wen Zhou,Chihiro Hayashi,Jie Sun,Bao-Hong Liu,Tadeyuki Imanaka,Jian-He Xu
A new β-glucosidase (DtGH) representing 40% identity with an apple seed glycosidase (ASG) was cloned from Dictyoglomus thermophilum . DtGH showed extremely high thermostability in aqueous solution, with half-lives of 533, 44, and 5 h measured at 70, 80 and 90 °C, respectively. Therefore it was used for direct glycosylation of n -octanol at 70 °C instead of 50 °C as usually. As a result, the glucose based conversion was increased by 27%, but the time spent to reach equilibrium was decreased from 7 d to 3 d. This enzyme also exhibited excellent stability under the reaction environment, retaining 70–80% of its initial activity after 7 d of incubation at 70 °C in either 1.7 M glucose solution or octanol-aqueous (85:15, v/v) system. It could retain part of synthetic activity even in boiling water. Owing to the strong glucose-tolerance and extremely high thermostability, DtGH should be promising for various glucosides synthesis.
研究领域:
生物化学
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酶工程
✓ 已验证
DOI
PubMed
高影响因子
CHEMICAL PAPERS
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2014
·Vol. 68
·期 8
·1132-1136
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IF 1.193
Tao Hong-Wen,Wang Xia,Yi Ping-Gui,Deng Zhi-Hong,Yu Xian-Yong,Li Xiao-Fang
A class of stereo-isomerically-pure alkanediol monoglycosides, 2-hydroxyethyl per- O -acetyl pyranosides ( IIIa-IIIf ), was conveniently prepared by a one-pot reaction of per- O -acetylated pyranoses ( Ia-If ) and 2-( tert -butyldimethylsilyloxy)ethanol ( II ) with catalysis by BF 3 ·OEt 2 . The α -( IIIa ) or β -linked glycosides ( IIIb-IIIf ) with 1,2- trans -configuration were obtained from glycosyl donors with participation of the neighbouring 2- O -acetyl group. BF 3 ·OEt 2 , along with hydrogen fluoride released from BF 3 ·OEt 2 under the experimental conditions used, facilitates the subsequent de-protection of siloxane to successfully afford 2-hydroxyethyl per- O -acetyl-pyranosides.
研究领域:
有机化学
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糖化学
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DOI
高影响因子
CHEMISTRY & BIODIVERSITY
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2021
·Vol. 18
·期 10
·e2100403
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IF 2.408
Jie Yan,Wenxiu Guo,Lanyu Zhou,Dale Guo,Jin Pei,Yun Deng,Haoyuan Zheng,Ding Liu,Xiaofang Xie,Cheng Peng
Three previously undescribed chlorophenyl glycosides, (2,4,6-trichloro-3-hydroxy-5-methoxyphenyl)methyl β-D-glucopyranoside ( 1 ), (2,4-dichloro-3,5-dimethoxyphenyl)methyl 6- O -β-D-glucopyranosyl-β-D-glucopyranoside ( 2 ) and 4-chloro-3-methoxy-5-methylphenyl 6- O -(6-deoxy-β-L-mannopyranosyl)-β-D-glucopyranoside ( 3 ) were obtained from Lilium regale . The absolute configurations of these new finds were elucidated by comprehensive analyses of spectroscopic data combined with acid hydrolysis derivatization. (2,4-dichloro-3,5-dimethoxyphenyl)methyl 6- O -β-D-glucopyranosyl-β-D-glucopyranoside ( 2 ) can inhibit the proliferation of lung carcinoma A549 cells with an IC 50 value of 29 μΜ. Graphical
研究领域:
植物化学
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药理学
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天然产物研究
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产品关联
DOI
PubMed
高影响因子
JOURNAL OF CHEMICAL ENGINEERING OF JAPAN
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2017
·Vol. 50
·期 9
·748-753
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IF 0.629
Zhaoyu Wang,Rongling Yang,Jizhong Wang,Yanhong Bi,Chun Zhu,Xiangjie Zhao,Linghong Nie,Wenqian Li
Regioselective enzymatic glycosylation of D-glucose and various structural alcohols for synthesizing β-D-glucopyranosides was successfully conducted. Among the β-glycosidases from seven potential plant seeds, the low-cost β-glycosidase from Prunus persica seed displayed excellent activity for salidroside preparation. Several crucial parameters, such as the solvent, buffer pH, buffer content, substrate molar ratio, enzyme dosage, and temperature were examined for yield optimization. Under the optimal conditions, the initial reaction rate and yield of salidroside were as high as 3.04 mM/h and 18.90%, respectively. Moreover, the alcohol acceptor recognition of the enzyme in synthesizing β-D-glucopyranosides was also investigated. The experimental data indicated that β-glycosidase activity and yield varied widely among all the tested alcohols due to the specific spatial structures of various acceptors.
研究领域:
生物化学
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酶工程
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DOI
高影响因子
JOURNAL OF INDUSTRIAL MICROBIOLOGY & BIOTECHNOLOGY
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2021
·
IF 3.346
Xue Yemin,Xue Mengke,Xie Fang,Zhang Mengchen,Zhao Hongyang,Zhou Tao
Alkyl glycosides are well-characterized nonionic surfactants, and can be prepared by transglycosylation reactions with retaining GH1 glycosidases being normally used for this purpose. The produced alkyl glycosides can also be hydrolyzed by the glycosidase, and hence, the yields of alkyl glycosides can be too low for industrial use. To improve the transglycosylation-to-hydrolysis ratio for a β-glucosidase from Thermotoga maritima (TmBglA) for the synthesis of alkyl glycoside, six mutants (N222F, N223C, N223Q, G224A, Y295F, and F414S) were produced. N222F, N223C, N223Q, G224A improved catalytic activity, F295Y and F414S are hydrolytically crippled with p-nitrophenol-β-d-glucopyranoside (pNPG) as substrate with an 85 and 70-fold decrease in apparent kcat, respectively; N222F shows the highest kcat/km value for pNPG. The substrate selectivity altered from pNPG to pNP-β-d-fucoside for N222F, F295Y, and F414S and from cellubiose to gentiobiose for N222F and F414S. Using pNPG (34 mM) and hexanol 80% (vol/vol), N222F, Y295F, and F414S synthesized hexyl-β-glycoside (HG) yields of 84.7%, 50.9%, and 54.1%, respectively, HG increased from 14.49 (TmBglA) to 22.8 mM (N222F) at 2 hr by 57.42%. However, this higher transglycosylation effect depended on that three mutants creates an environment more suited for hexanol in the active site pocket, and consequently suppressed its HG hydrolysis.
研究领域:
生物化学
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酶工程
✓ 已验证
DOI
PubMed
高影响因子
ACS Sustainable Chemistry & Engineering
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2024
·
IF 7.1
Mizeng Wang,Qiyu Liu,Xueqing Qiu,Run Tang,Zihan Zhang,Qiaozhi Ma
Glucan oligomers are unique chemicals with versatile value-added applications in agriculture and healthcare depending on their specific glycosidic linkages. Glucose glycosylation shows high efficiency in glucan oligomer production, but the formed glycosidic bonds are generally random, which limits its application. To address this issue, we employed an unacidified molten salt hydrate (MSH) of LiBr·3.2H2O as the reaction medium and glucose/disaccharides as the substrate. Results showed that a 66.6% yield of glucan oligomer can be produced from glucose with a high selectivity of 93.2%, suggesting limited byproduct degradation. When maltose was used as the substrate, the initial α(1 → 4) glycosidic bonds were well preserved. Maltose was effectively converted into an α-type glucan oligomer consisting of 79.9% α(1 → 4) and 20.1% α(1 → 6) glycosidic linkages. The kinetic analysis revealed that the α(1 → 4) bond has a high activation energy of 57.9 kJ/mol, ensuring its chemical stability in unacidified LiBr·3.2H2O conversion. The unacidified MSH reaction medium presents a possibility of enhanced and structure-tunable glucan oligomer production via a glycosylation method.
研究领域:
生物化学
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食品科学
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农业科学
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产品关联
DOI
高影响因子
FOOD CHEMISTRY
·
2024
·
IF 8.5
Han Yan,Wei-Xuan Li,Ying-Lin Zhu,Zhi-Yuan Lin,Dan Chen,Yue Zhang,Hai-Peng Lv,Wei-Dong Dai,De-Jiang Ni,Zhi Lin,Yin Zhu
The Fujian and Yunnan provinces in China are the most representative origins of white tea. However, the key differences in the chemical constituents of the two white teas have rarely been revealed. In this study, a comprehensive comparison of the aroma profiles, chiral volatiles, and glycosidically bound volatiles (GBVs) in Fujian and Yunnan white teas was performed, and 174 volatiles and 28 enantiomers, including 22 volatiles and six GBVs, were identified. Linalool, linalyl-β-primeveroside (LinPrim), and α-terpineol presented the opposite dominant configurations in Fujian and Yunnan white teas, and the chiral GBVs were firstly quantified with significant differences in the contents of R -LinPrim and β- d -glucopyranosides of (2 R , 5 R )-linalool oxide A and (2 R , 5 S )-linalool oxide B. Moreover, discrimination functions for Fujian and Yunnan white teas were created using nine key variables with excellent reliability and efficiency. These results provide a new method for objectively distinguishing authentic white teas according to geographical origin.
研究领域:
食品科学
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分析化学
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农业化学
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产品关联
DOI
PubMed
高影响因子
JOURNAL OF AGRICULTURAL AND FOOD CHEMISTRY
·
2015
·
IF 2.912
Jiadong Gui,Xiumin Fu,Ying Zhou,Tsuyoshi Katsuno,Xin Mei,Rufang Deng,Xinlan Xu,Linyun Zhang,Fang Dong,Naoharu Watanabe,Ziyin Yang
It was generally thought that aroma of oolong tea resulted from hydrolysis of glycosidically bound volatiles (GBVs). In this study, most GBVs showed no reduction during the oolong tea manufacturing process. β-Glycosidases either at protein or gene level were not activated during the manufacturing process. Subcellular localization of β-primeverosidase provided evidence that β-primeverosidase was located in the leaf cell wall. The cell wall remained intact during the enzyme-active manufacturing process. After the leaf cell disruption, GBV content was reduced. These findings reveal that, during the enzyme-active process of oolong tea, nondisruption of the leaf cell walls resulted in impossibility of interaction of GBVs and β-glycosidases. Indole, jasmine lactone, and trans-nerolidol were characteristic volatiles produced from the manufacturing process. Interestingly, the contents of the three volatiles was reduced after the leaf cell disruption, suggesting that mechanical damage with the cell disruption, which is similar to black tea manufacturing, did not induce accumulation of the three volatiles. In addition, 11 volatiles with flavor dilution factor ≥44 were identified as relatively potent odorants in the oolong tea. These results suggest that enzymatic hydrolysis of GBVs was not involved in the formation of volatiles of oolong tea, and some characteristic volatiles with potent odorants were produced from the manufacturing process.
研究领域:
食品科学
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植物学
·
生物化学
✓ 已验证
DOI
PubMed
高影响因子
JOURNAL OF CHROMATOGRAPHY B-ANALYTICAL TECHNOLOGIES IN THE BIOMEDICAL AND LIFE SCIENCES
·
2015
·
IF 2.729
Hongjuan Li,Ying Liu,Haizhu Jin,Sujing Liu,Shengtao Fang,Chunhua Wang,Chuanhai Xia
Vitexin-4″- O -glucoside and vitexin-2″- O -rhamnoside are the major flavonoids of hawthorn leaves. In this work, the adsorption and desorption characteristics of vitexin-4″- O -glucoside and vitexin-2″- O -rhamnoside on seven macroporous resins were evaluated. Among the tested resins, the HPD-400 resin showed the best adsorption and desorption capacities. Adsorption isotherms were constructed for the HPD-400 resin and well fitted to Langmuir and Freundlich models. Dynamic adsorption and desorption tests were performed on column packed with the HPD-400 resin to optimize the chromatographic parameters. After one run treatment with the HPD-400 resin, the contents of vitexin-4″- O -glucoside and vitexin-2″- O -rhamnoside in the product were increased 8.44-fold and 8.43-fold from 0.720% and 2.63% to 6.08% and 22.2% with recovery yields of 79.1% and 81.2%, respectively. These results show that the developed method is a promising basis for the large-scale purification of vitexin-4″- O -glucoside and vitexin-2″- O -rhamnoside from hawthorn leaves and other plant materials.
研究领域:
植物化学
·
分离纯化技术
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DOI
PubMed
高影响因子
危险品化学品经营许可证（带存储）