1.Application of immobilized glycosidase in the synthesis of glycoside compounds.
Jiawei DAI ; Hanchi CHEN ; Xiao JIN ; Xiaocan MAO ; Linjiang ZHU ; Yuele LU ; Xiaolong CHEN
Chinese Journal of Biotechnology 2021;37(12):4169-4186
Glycoside compounds are widely used in medicine, food, surfactant, and cosmetics. The glycosidase-catalyzed synthesis of glycoside can be operated at mild reaction conditions with low material cost. The glycosidase-catalyzed processes include reverse hydrolysis and transglycosylation, appropriately reducing the water activity in both processes may effectively improve the catalytic efficiency of glucosidase. However, glucosidase is prone to be deactivated at low water activity. Thus, glucosidase was immobilized to maintain its activity in the low water activity environment, and even in neat organic solvent system. This article summarizes the advances in glycosidase immobilization in the past 30 years, including single or comprehensive immobilization techniques, and immobilization techniques combined with genetic engineering, with the aim to provide a reference for the synthesis of glycosides using immobilized glycosidases.
Catalysis
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Enzymes, Immobilized
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Glycoside Hydrolases/genetics*
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Glycosides/biosynthesis*
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Hydrolysis
2.Isolation and identification of endophytic fungi producing harpagoside and harpagide from Scrophularia ningpoensis.
Zhan-Yun SHEN ; Bo ZHU ; Quan-Long ZHANG ; Lu-Ping QIN
China Journal of Chinese Materia Medica 2019;44(10):2046-2050
The endophytic fungi from root,main stem,branch and leaf of Scrophularia ningpoensis were isolated from Zhejiang,whether these strains could yield harpagide or harpagoside were tested by HPLC and LC-MS. According to the morphological characteristic and the similarity of the nucleotide sequence of internal transcribed spacer( ITS) between r DNAs,the strains producing harpagide or harpagoside were identified. The results showed that 210 strains were isolated from the samples,which were classified into 9 orders,13 families and 17 genera by morphological study. Harpagide was detected in endogenous fungi ZJ17 and harpagoside was detected in endogenous fungi ZJ25 by HPLC coupled with LC-MS. ZJ17 was identified as Alternaria alternate and ZJ25 was identified as A.gaisen by its morphology and authenticated by ITS( ITS4 and ITS5 regions and the intervening 5. 8 S rDNA region).
China
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DNA, Fungal
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genetics
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DNA, Ribosomal Spacer
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genetics
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Endophytes
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classification
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metabolism
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Fungi
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classification
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metabolism
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Glycosides
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biosynthesis
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Iridoid Glycosides
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metabolism
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Pyrans
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metabolism
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Scrophularia
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microbiology
3.Effects of methyl jasmonate and salicylic acid on phenylethanoid glycosides synthesis in suspension cultures of Cistanche deserticola.
Liang-Sheng XU ; Xiao-Feng XUE ; Chun-Xiang FU ; Zhi-Ping JIN ; Yu-Quan CHEN ; De-Xiu ZHAO
Chinese Journal of Biotechnology 2005;21(3):402-406
The present study investigated the influence of the methyl jasmonate and salicylic acid elicitors on the formation of phenylethanoid glycosides (PeG) in the suspension cultures of Cistanche deserticola. The results showed that methyl jasmonate and salicylic acid enhanced greatly the accumulation of PeG and echinacoside (Echin), but their optimum elicitation dosage and addition time were different. The yields of PeG and Echin were significantly increased in the presence of 5 micromol/L methyl jasmonate on day 14 (up to 2.59-fold and 3.82-fold, respectively), whereas treated with 50 micromol/L salicylic acid on day 28, the maximum content of them were, respectively, 2.71 and 3.16-fold higher than the untreated cell cultures.
Acetates
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pharmacology
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Cell Culture Techniques
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Cistanche
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drug effects
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metabolism
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Culture Media
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Cyclopentanes
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pharmacology
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Glycosides
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biosynthesis
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Oxylipins
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pharmacology
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Phenylethyl Alcohol
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metabolism
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Salicylic Acid
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pharmacology
4.Suppressive effects of GTW treatment on mesangial lesions in experimental irreversible glomerulosclerosis.
Yi-gang WAN ; Wei SUN ; Fujio SHMIZU ; Liu-bao GU ; Koichi SUZIKI ; Tamaki KARASAWA ; Hiroshi KAWACHI
China Journal of Chinese Materia Medica 2005;30(5):361-365
OBJECTIVETo examine suppressive effects of multi-glycoside of Tripterygium wilfordii Hook. f. (GTW)on mesangial injury induced by two-injecti on of anti-Thy1. 1 monoclonal antibody(mAb) 1-22-3 in vitro.
METHODWe established the irreversible model of glomerulosclerosis with anti-Thy1. 1 mAb 1-22-3. After 42 days of oral treatment with GTW (50 mg x kg(-1) BW)and vehicle (distilled water), to observe effects of GTW on proteinuria, renal function, mesangial morphological change, and mRNA expressions of collagen type I and TGF-beta by light microscope (LM), immunofluorescence (IF), and Reverse Transcription Polymerase Chain Reaction (RT-PCR).
RESULTGTW ameliorated proteinuria (from day24 to day 42) and mesangial proliferation [total cell number, GTW group 65.67+/-3.43 vs. control group 87.02+/-2.41, P < 0.05; matrix expansion, GTW group 1.20+/-0.06 vs. control group 2.77+/-0.23, P < 0.05; alpha-smooth muscle actin(alpha-SMA) expression, GTW group 1.75+/-0.33 vs. control group 2.62+/-0.15, P < 0.05; collagen type I expression, GTW group 1.68+/-0.31 vs. control group 2.06+/-0.24, P < 0.05], moreover, significantly reduced the glomerular expression of mRNA for collagen type 1(53.5% to the control group, P < 0.05)and TGF-beta(14.7% to the control group, P < 0.05)on day 42day.
CONCLUSIONGTW can not only decrease proteinuria, but also ameliorate mesangial alterations probably by the reduction of cytokines. GTW may be a promising agent for the prevention of progressive and irreversible glomerulosclerosis.
Actinin ; metabolism ; Animals ; Collagen Type I ; biosynthesis ; genetics ; Female ; Glomerular Mesangium ; metabolism ; pathology ; Glomerulonephritis, Membranoproliferative ; metabolism ; pathology ; Glycosides ; isolation & purification ; pharmacology ; Plants, Medicinal ; chemistry ; Proteinuria ; drug therapy ; RNA, Messenger ; biosynthesis ; genetics ; Rats ; Rats, Wistar ; Transforming Growth Factor beta ; biosynthesis ; genetics ; Tripterygium ; chemistry
5.Preventive effect of multi-glycoside of tripterygium Wilfordii Hook. f. on proteinuria and mesangial injury in experimental mesangial proliferative glomerulonephritis.
Yi-gang WAN ; Wei SUN ; Yan-jun ZHEN
Chinese Journal of Integrated Traditional and Western Medicine 2005;25(9):817-821
OBJECTIVETo observe the preventive effect of multi-glycoside of Tripterygium Wilfordii Hook. f. (GYW) on proteinuria and mesentery injury in experimental mesangial proliferative glomerulonephritis in vivo.
METHODSThe reversible anti-Thyl.1 antibody glomerulo nephritis model of rats was established with monoclonal antibody 1-22-3 and intervened with GTW, and a control group was set up in the same time. Changes of 24h urinary protein excretion, serum creatinine (Scr), blood urea nitrogen (BUN), total plasma protein (TP) and glomerular morphology were observed, and the level of mRNA expression of proliferative factors, including platelet-derived growth factor-BB (PDGF-BB) and transforming growth factor-beta (TGF-beta), in renal tissue was determined.
RESULTSGTW could inhibit proteinuria and mesangial injury in anti-Thyl. 1 antibody nephritis model. The PDGF-BB and TGF-beta mRNA expression in the anti-Thy1.1 antibody nephritis model rats were increased for 2.84 and 1.64 times respectively to those in the normal control group. GTW could down-regulate the over-expression of PDGF-BB mRNA by 33.1%, it was significantly different to that in the control group (P < 0.05).
CONCLUSIONGTW could reduce the proteinuria and inhibit mesangial cells proliferation and extracellular matrix deposition, these effects maybe related to the down-regulating of PDGF-BB mRNA expression.
Animals ; Antibodies, Monoclonal ; immunology ; Drugs, Chinese Herbal ; therapeutic use ; Female ; Glomerular Mesangium ; pathology ; Glomerulonephritis, Membranoproliferative ; chemically induced ; metabolism ; prevention & control ; Glycosides ; isolation & purification ; pharmacology ; therapeutic use ; Phytotherapy ; Plant Extracts ; therapeutic use ; Platelet-Derived Growth Factor ; biosynthesis ; genetics ; Proteinuria ; prevention & control ; Proto-Oncogene Proteins c-sis ; Random Allocation ; Rats ; Rats, Wistar ; Thy-1 Antigens ; immunology ; Transforming Growth Factor beta ; biosynthesis ; genetics ; Tripterygium ; chemistry
6.Inhibitory effects of tilianin on the expression of inducible nitric oxide synthase in low density lipoprotein receptor deficiency mice.
Ki Hoan NAM ; Jae Hoon CHOI ; Yun Jeong SEO ; Young Mi LEE ; Yong Sung WON ; Mi Ran LEE ; Mi Ni LEE ; Jong Gil PARK ; Young Myeong KIM ; Hyoung Chin KIM ; Chul Ho LEE ; Hyeong Kyu LEE ; Sei Ryang OH ; Goo Taeg OH
Experimental & Molecular Medicine 2006;38(4):445-452
We investigated the effect of tilianin upon inducible nitric oxide synthesis in the plasma of low-density lipoprotein receptor knock-out (Ldlr-/-) mice fed with high cholesterol diet and in primary peritoneal macrophages of Ldlr-/- mice. High cholesterol diet induced nitric oxide production in the plasma of Ldlr-/- mice. Tilianin reduced the level of nitric oxide (NO) in plasma from Ldlr-/- mice induced by the high cholesterol diet. Tilianin also inhibited the NO production from the primary culture of peritoneal macrophages treated with lipopolysaccharide. The inhibition of NO production was caused by the suppression of inducible nitric oxide synthase (iNOS) gene expression in peritoneal macrophages isolated from Ldlr-/- mice. Moreover, tilianin inhibited the transcriptional activation of iNOS promoter that has NF-kappa B binding element. Thus, these results provide the first evidence that tilianin inhibit iNOS expression and production of NO and may act as a potential anti-inflammatory agent.
Tyrosine/analogs & derivatives/metabolism
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Tissue Distribution
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Sinus of Valsalva/metabolism/pathology/ultrastructure
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Receptors, LDL/*genetics
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Promoter Regions (Genetics)/drug effects
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Nitric Oxide Synthase Type II/*metabolism
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Nitric Oxide/biosynthesis/blood
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NF-kappa B/metabolism
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Mice, Knockout
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Mice
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Male
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Inflammation/metabolism
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Glycosides/*pharmacology
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Flavonoids/*pharmacology
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Down-Regulation/drug effects
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Atherosclerosis/metabolism
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Animals
7.Effects of multi-glycoside of Tripterygium wilfordii Hook. f. on proteinuria and expression of slit diaphragm-associated molecules in rats with anti-thy1.1 glomerulonephritis.
Yi-Gang WAN ; Wei SUN ; Yang WANG
Chinese Journal of Integrated Traditional and Western Medicine 2006;26(12):1094-1102
OBJECTIVETo examine the effect of multi-glycoside of Tripterygium wilfordii Hook. f. (GTW) on proteinuria and expression of slit diaphragm-associated molecules such as nephrin and podocin in glomerulonephritis induced by anti-Thy1.1 antibody (anti-Thy1 . 1 GN).
METHODSAnti-Thy1.1 GN was induced in rats by a single intravenous injection with 500 microg of anti-Thy1.1 mAb 1-22-3. Fourteen rats were randomly divided into 2 groups, the GTW-treated group and vehicle treated group, and sacrificed on day 14 in Experiment 1 or on day 7 in Experiment 2 after induction of Anti-Thy1.1 GN. Daily oral administration of GTW and vehicle as a control was started from 3 days before injection or at the same time of injection to the day of sacrifice in Experiment 1 or 2. Proteinuria was determined during 14 days in Experiment 1 or during 7 days in Experiment 2. From kidneys taken at sacrifice, glomerular morphological changes, glomerular macrophage infiltration, glomerular expression of nephrin and podocin, and its mRNA expression in renal tissue were examined.
RESULTSIn Experiment 1, proteinuria and mesangial matrix expansion were significantly attenuated by GTW treatment. No difference in staining intensity of nephrin and podocin in glomeruli was observed between GTW treated group and vehicle treated group on day 14. In Experiment 2, GTW treatment significantly ameliorated proteinuria, mesangial injury and activated macrophage infiltration in glomerulus. In addition, it significantly increased the expression of nephrin and podocin and its mRNA expression in glomeruli on day 7.
CONCLUSIONIn anti-Thy1.1 GN, the reduced expression of nephrin and podocin may contribute to the development of mesangial injury and proteinuria. The findings suggest that GTW ameliorates not only proteinuria but also mesangial lesions in anti-Thy1 . 1 GN most likely by increasing the expression of nephrin and podocin.
Animals ; Female ; Fluorescent Antibody Technique ; Glomerulonephritis, Membranoproliferative ; drug therapy ; immunology ; Glycosides ; therapeutic use ; Intracellular Signaling Peptides and Proteins ; genetics ; Isoantibodies ; immunology ; Membrane Proteins ; biosynthesis ; genetics ; Phytotherapy ; Podocytes ; drug effects ; metabolism ; pathology ; Proteinuria ; drug therapy ; Rats ; Reverse Transcriptase Polymerase Chain Reaction ; Thy-1 Antigens ; immunology ; Tripterygium ; chemistry
8.Effect of PMTG on atherosclerotic lesion formation and expression of ICAM-1 and VCAM-1 in ApoE-deficient mice.
Wei FANG ; Hui-xin ZHANG ; Lu-ya WANG ; Yan-wen QIN ; Ying WU ; Wei WANG ; Bin LIU
China Journal of Chinese Materia Medica 2007;32(13):1320-1323
OBJECTIVETo study the protecting effect of polygoni multiflori total glycosides (PMTG) on the atherosclerotic lesion formation and the expression of ICAM-1, VCAM-1 in aolipoprotein (apo) E-deficient transgenic mice.
METHODThirty-two female apoE-deficienct mice were randomized into four groups: PMTG high dose group (150 mg x kg x d), low dose group (25 mg x kg x d), atorvastatin positive control group (5 mg x kg x d), and model group. At the end of the tenth week, all mice were killed. The serum levels of Total cholesterol (TC), Triglyceride (TG), High-density lipoprotein-cholesterol (LDL-C) were measured by enzyme dynamics method. Transmission electron microscopy (TEM) were used to observe the morphologic changes of aortic endothelia cell. The expressions of NF-kappaB were studied by SABC immunohistochemistry.
RESULTAs compared with the model control group. (1) PMTG could reduce the levels of serum TC, TG significantly (P < 0.01), and LDL-C level significantly (P < 0.01). (2) It could increase the levels of serum NO and the anti-oxidation capacities significantly (P < 0.01), but reduce the levels of serum MDA significantly (P < 0.01). (3) PMTG could keep the normal morphology of aortic endothelial cell. (4) PMTG could deregulated the expression of NF-kappaB in aortic wall.
CONCLUSIONPMTG could inhibit the occurrence and development of atherosclerotic lesions by its anti-oxidation abilities, which reduce LDL-C level. The low LDL-C level could deregulated the of expression of NF-kappaB, which could deregulated ICAM-1 and VCAM-1 in AopE-/-mice in aortic wall through.
Animals ; Antioxidants ; pharmacology ; Aorta, Thoracic ; drug effects ; metabolism ; pathology ; Apolipoproteins E ; deficiency ; genetics ; Atherosclerosis ; blood ; pathology ; prevention & control ; Cholesterol ; blood ; Cholesterol, LDL ; blood ; Endothelial Cells ; drug effects ; pathology ; ultrastructure ; Female ; Glycosides ; isolation & purification ; pharmacology ; Immunohistochemistry ; Intercellular Adhesion Molecule-1 ; biosynthesis ; Malondialdehyde ; blood ; Mice ; Mice, Knockout ; Microscopy, Electron, Transmission ; NF-kappa B ; metabolism ; Nitric Oxide ; blood ; Plants, Medicinal ; chemistry ; Polygonum ; chemistry ; Random Allocation ; Triglycerides ; blood ; Vascular Cell Adhesion Molecule-1 ; biosynthesis