CN104404065A - Mangosteen glycosyltransferase gene UGT74AC1 and application thereof - Google Patents
Mangosteen glycosyltransferase gene UGT74AC1 and application thereof Download PDFInfo
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Abstract
The invention discloses a mangosteen glycosyltransferase gene (i)UGT74AC1(/i) and application of glycosyltransferase with a gene (i)UGT74AC1(/i) code in synthetic mogrosideIE. The glycosyltransferase gene (i)UGT74AC1(/i) has a nucleotide coding sequence shown in SEQIDNO.1 and a peptide sequence shown in SEQIDNO.2. By utilization of an expression of the mangosteen glycosyltransferase gene (i)UGT74AC1(/i) in escherichia coli, the recombinant glycosyltransferase (i)UGT74AC1(/i) can catalyze mogrol and UDP-glucose to react, thereby generating the mogrosideIE. The glycosyltransferase gene (i)UGT74AC1(/i) disclosed by the invention can be applied to the artificial synthesis of the mogrosideIE. Meanwhile, the gene has an important application value in the aspect of improving momordica grosvenori by the utilization of a transgenic technology to improve the content of the mogroside.
Description
Technical field
The present invention relates to biological technical field, more specifically relate to a kind of new glycosyltransferase
uGT74AC1and generate the application in Momordica-Glycosides I E at catalysis momordica grosvenori alcohol.
Background technology
Grosvenor Momordica be Curcurbitaceae liana deciduous plant Grosvenor Momordica (
siraitia grosvenoriiswingle) mature fruit, is the specific precious medicinal and sweetener plant of China, has included in Pharmacopoeia of People's Republic of China always, use as conventional Chinese medicine since 1977.Grosvenor Momordica is listed in first and " is medicine and the kind list of food " by the Ministry of Health and the State Administration of Traditional Chinese Medicines.Arhat fruity is extremely sweet, cool in nature, nontoxic, there is relieving cough and moistening lung, reduce phlegm enrich blood, relax bowel, the functions such as the stasis of blood of dispelling (Prakash, Indra, and Venkata Sai Prakash Chaturvedula. Additional New Minor Cucurbitane Glycosides from Siraitia grosvenorii.
molecules19.3 (2014): 3669-3680.).
Momordica-Glycosides is the main active substances in Grosvenor Momordica, it is the desirable natural sweeteners of a kind of high sugariness, low calory, there is the effect (Chiu such as hypoglycemic, anti-oxidant, anticancer, antiviral in addition, Chun-Hui, et al. Biotransformation of Mogrosides from Siraitia grosvenorii Swingle by Saccharomyces cerevisiae. Journal of agricultural and food chemistry 61.29 (2013): 7127-7134.).Momordica-Glycosides is cucurbitane type tetracyclic triterpenoid, and since the seventies in last century, Chinese scholars has carried out large quantity research to it, and be successively separated from Grosvenor Momordica obtain Momordica-Glycosides I E,
e,
,
,
,
with sweet glucosides of kind more than 20 such as Simon glucosides.This kind of material is except minority, be extremely sweet or micro-sweet composition, wherein Momordica grosvenori mogroside V is the composition that in Grosvenor Momordica, content is the highest, its sugariness concentration in water is ten thousand/for the moment, 425 times of (Kasai R of 5% aqueous sucrose solution, Nie R L, Nashi K, et al. Sweet Cucurbitane Glycosides from Fruits of Siraitia siamensis (chi-zi luo-han-guo), a Chinese Folk Medicine (Organic Chemistry) [J]. Agricultural and biological chemistry, 1989, 53 (12): 3347-3349.).Momordica-Glycosides chemical structure is complicated, at present can't chemosynthesis, can only extract and obtain from Grosvenor Momordica.Meanwhile, because Grosvenor Momordica requires growing environment harsh, be only limitted to the minority areas such as In Northern Guangxi and generate, and the fruit growth cycle is long, sweet salidroside content is low, and fruit yield is large by natural environment influence, cannot meet the need of market, therefore urgently explore the novel method improving Momordica-Glycosides.
Glycosyltransferase (Glycosyltransferase) is the large fermentoid extensively existed in organism, it by the saccharide donor of activity as UDPG, UDP-semi-lactosi etc. transfer to-COOH ,-the OH ,-NH of saccharide acceptor as compounds such as triterpenes, flavonoid, phenyl propyls
2deng group being formed glucosides (Das, Shibendu Sekhar, et al. Purification and characterization of a betanidin glucosyltransferase from Amaranthus tricolor L catalyzing non-specific biotransformation of flavonoids. Plant Science 211 (2013): 61-69.).Glycosylation is one of significant biochemical reaction common in organism, the stability of saccharide acceptor, water-soluble, biological activity and in intracellular transport and location is changed by glycosylation, in addition, can also reduce or remove toxicity (Richman that is endogenous and exogenous material by glycosylation, Alex, et al. Functional genomics uncovers three glucosyltransferases involved in the synthesis of the major sweet glucosides of
stevia rebaudiana. The Plant Journal 41.1 (2005): 56-67.).The common precursor substance of Momordica-Glycosides is momordica grosvenori alcohol, and its No. 3 carbon can be glycosylated respectively with the hydroxyl that No. 24 carbon are connected and generate corresponding Momordica-Glycosides by β-1 → 6 glycosidic link
e and Momordica-Glycosides
a, or No. 3 carbon are glycosylated generation Momordica-Glycosides with the hydroxyl that No. 24 carbon are connected simultaneously
e.In addition, No. 2 position hydroxyls and No. 6 position hydroxyls of momordica grosvenori alcohol No. 3 carbon and the glucose molecule that No. 24 carbon hydroxyls are connected all can continue again to be glycosylated, thus generate the Momordica-Glycosides at most containing 6 glucosyl groups
.Glycosylation modified is final step reaction in Momordica-Glycosides biosynthetic pathway, and glycosylated degree determines the quality of Momordica-Glycosides.The current still blank out of the glycosylation modified mechanism of current Momordica-Glycosides, finds and in the glycosylation modified process of clear and definite Momordica-Glycosides, crucial glycosyltransferase has great importance to Grosvenor Momordica breeding and by metabolic engineering technology generation Momordica-Glycosides.
uGT74AC1be a member in momordica grosvenori sugar based transferase family, found to comprise in transcript profile research before
uGT74AC1interior may participate in Momordica-Glycosides route of synthesis a large amount of glycosyltransferase encoding genes (Tang, Qi, et al. An efficient approach to finding
siraitia grosvenoriitriterpene biosynthetic genes by RNA-seq and digital gene expression analysis. BMC genomics 12.1 (2011): 343.), but and whether these glycosyltransferases indefinite are genuine relevant with the synthesis of Momordica-Glycosides.Existing literature search shows, at home and abroad there is no any relevant glycosyltransferase
uGT74AC1in the relevant report of the sweet glucoside synthesis of catalysis.
Summary of the invention
An object of the present invention is to provide the glycosyltransferase gene excavated from Grosvenor Momordica transcript profile database
uGT74AC1,its nucleotide sequence is as SEQ ID NO:1, and coded peptide sequence is as SEQ ID NO:2.Specifically with Grosvenor Momordica pulp for raw material, after liquid nitrogen is milled, utilize Trizol reagent to extract Grosvenor Momordica total serum IgE, then with the RNA extracted for template reverse transcription obtains total cDNA of Grosvenor Momordica.After obtaining total cDNA, recycle specific primer and obtain glycosyltransferase by pcr amplification
uGT74AC1encoding gene.
Two of object of the present invention is to provide a kind of glycosyltransferase
uGT74AC1expression and purification method.The glycosyltransferase specifically will obtained
uGT74AC1pass through
ndei and
ecorI double digestion and same warp
ndei and
ecothe colibacillus expression plasmid of RI double digestion process connects, and recombinant plasmid is after sequence verification is correct, then conversion imports in intestinal bacteria Rosetta gami (DE3), builds recombination bacillus coli.In picking recombination bacillus coli list colony inoculation to 5 mL LB substratum, 37 DEG C, under 200rmp condition, overnight incubation.According to the inoculum size of 1%, seed liquor is inoculated in 100 mL substratum, 37 DEG C, under 200rmp condition, cultivate 2-3 h.When cell concentration OD600 reaches 0.6-0.8, add the IPTG that final concentration is 0.1 mmol, reduce culture temperature to 16 DEG C, shaking speed is reduced to 150 rmp, and induction time is 20h simultaneously.Then by collected by centrifugation thalline, after ultrasonication, recentrifuge collects broken liquid supernatant and relating operation purifying target protein on the histidine-tagged recombinant protein purification handbook provided according to GE company
uGT74AC1.
Three of object of the present invention is to provide one and utilizes glycosyltransferase
uGT74AC1catalysis momordica grosvenori alcohol generates sweet glucoside
the method of E.Particularly in enzyme reaction system, add 50 mM Tris-HCL, 5 mM MgCl
2, 0.2 mM momordica grosvenori alcohol, 1 mM UDPG and 100 μ g purifying
uGT74AC1albumen, reacts 4 h under 30 DEG C of conditions.
Adopt above technical scheme, the invention provides a kind of glycosyltransferase
uGT74AC1and generate the application in Momordica-Glycosides I E at catalysis momordica grosvenori alcohol.Experiment proves, glycosyltransferase
uGT74AC1can in intestinal bacteria solution expression with high efficiency, and can with momordica grosvenori alcohol and UDPG for substrate, catalysis generates Momordica-Glycosides I E.The discovery of this gene also provides important theoretical basis for utilizing genetic engineering bacterium to transform Grosvenor Momordica with the content improving Momordica-Glycosides simultaneously.
Accompanying drawing explanation
The expression of recombinant e. coli carrier pET21-that Fig. 1 builds
uGT74AC1physical map
Fig. 2 have expressed recombinant plasmid pET21-
uGT74AC1coli somatic, broken supernatant, precipitation and purified product SDS-PAGE electrophorogram;
Fig. 3 is
uGT74AC1high performance liquid chromatography (HPLC) collection of illustrative plates of reaction product;
Fig. 4. the mass-spectrogram of glycation product.
Embodiment
Below in conjunction with accompanying drawing and concrete case study on implementation, the specific embodiment of the present invention is described in detail.Following embodiment only for illustration of the present invention, but is not used in restriction use range of the present invention.It should be pointed out that to those skilled in the art, without departing from the inventive concept of the premise, several variation and improvement can also be made.These all belong to protection scope of the present invention.Unreceipted specific experiment method in following case study on implementation, usual conveniently condition, the molecular cloning of such as Sambrook etc.: laboratory manual (New York:Cold Spring Harbor Laboratory Pross, 1989) condition described in, or according to the suggestion that related reagent manufacturer provides.
Embodiment 1, glycosyltransferase gene
uGT74AC1the structure of Cloning and prokaryotic expression carrier
With Grosvenor Momordica pulp for raw material, according to TRIzol (Invitrogen, USA) operation steps on test kit extracts Grosvenor Momordica total serum IgE, then to extract the total serum IgE of acquisition for template, First Strand cDNA Synthesis Kit (Ferments, USA) reverse transcription is utilized to obtain total cDNA of Grosvenor Momordica.According to NCBI(http: //www.ncbi.nlm.nih.gov/) Grosvenor Momordica glycosyltransferase gene that database is announced
uGT74AC1dNA sequence dna, design a pair Auele Specific Primer UGT74AC1-F:CGC
cATATG cACCACCACCACCACCACATG
GAGAAAGGCGATACGCATATT and UGT74AC1-R:CGGAATTCTCAA
GTTTGCTTGAGCATGGCCAC increases
uGT74AC1complete sequence.By what obtain
uGT74AC1first pass through
ndei and
ecoafter RI enzyme is cut, with same warp
ndei and
ecothe pET21a of RI double digestion process carries out connection construction of expression vector pET21-UGT74AC1(accompanying drawing 1).
The structure of embodiment 2, E. coli recombinant stain and the expression of target protein and separation and purification
Transformed by expression vector pET21-UGT74AC1 correct for order-checking and import E. coli expression strains Rosetta gami (DE3), transformant has entered after E. coli expression strains Rosetta gami (DE3) for recombinant protein through bacterium colony PCR checking recombinant plasmid pET21-UGT74AC1 again
uGT74AC1expression.With the addition of the appropriate E. coli transformant of LB inoculation of medium of the penbritin of respective concentration, kantlex, paraxin and Streptomycin sulphate, 37 DEG C, 220 rpm incubated overnight.Then overnight culture is inoculated into fresh containing in corresponding antibiotic LB substratum in the ratio of 2:100,37 DEG C, 220 rpm are cultured to thalline OD
600for 0.6-0.8.Then adding IPTG to final concentration is 0.1 mM, at 16 DEG C, cultivates the expression that 16-20h induces target protein under 150 rpm.After having induced, 6000 rpm are centrifugal, and 10 min collect thalline, are then suspended and Buffer A(25 mM Tris-HCl, 150 mM NaCl, 30 mM Imidazole, PH=7.2 by thalline) in, under 4 DEG C of conditions, high-pressure breaking is carried out to thalline.By the broken liquid of Bacillus coli cells centrifugal 60 min under 15000 rpm conditions, collect supernatant and join in the nickel agarose column balanced with Buffer A in advance, according to the operation on GE protein purification handbook, with Buffer B (25 mM Tris-HCl, 150 mM NaCl, 250 mM Imidazole, PH=7.2) gradient elution is carried out to target protein.The purity of target protein detects through SDS-PAGE and reaches electrophoresis pure (accompanying drawing 2), can be used for follow-up enzyme activity determination.
Case study on implementation 3,
uGT74AC1the mensuration that enzyme is lived
Measure at the EP pipe of 2 mL
uGT74AC1enzyme live.Reaction system is: 1 mM UDPG, 0.2 mM momordica grosvenori alcohol, 100 μ g
uGT74AC1albumen, 50 mM Tri-HCl (PH 7.2), react 4 h under 30 DEG C of conditions.Then by isopyknic extraction into ethyl acetate reaction product 3 times, synthesis extraction product also dries up with nitrogen.Finally product is dissolved in hplc grade methanol, analyzes for LC-MS after the filter membrane process of 0.22 μm.
The LC-MS qualification of case study on implementation 4, enzyme reaction product
Utilize HPLC to analyze enzyme reaction product, liquid phase systems is Agilent 1260 system, and chromatographic column is Welch Ultimate C18 post (250 mm × 4.6 mm, 5 μm), sample size is 20 μ L, UV-detector, and determined wavelength is 210 nm.Moving phase is acetonitrile and water, and gradient operation method is: 0-20 min, 23% acetonitrile; 20-60 min, 50% acetonitrile.HPLC result display (accompanying drawing 3)
uGT74AC1can generate a new product peak by catalysis momordica grosvenori alcohol, this product appearance time is 36.10 min, and appearance time is consistent with the appearance time of Momordica-Glycosides I E standard substance.When the total protein extracted with the intestinal bacteria that have expressed empty carrier pET21 and momordica grosvenori alcohol carry out reacting and utilize same liquid chromatographic detection condition to detect, new product is not had to generate at 36.10 min places.
Mass spectrograph is Bruker-micrOTOF-II, ESI ion source, negative ion mode.Ionic conditions after optimization is: ion spray voltage is 4500V; Capillary temperature is 400 DEG C, and dry gas is nitrogen, and flow velocity is 6 mL/min, and drying temperature is 180 DEG C.Mass spectral results display (accompanying drawing 4)
uGT74AC1the reaction product of albumen and momordica grosvenori alcohol comprises (m/z, 637 [M-H] at the fragment ion at 36.10 min places
-, 683 [M-H+HCOOH]
-and 751 [M-H+TFA]
-), this with sweet glucoside I E standard substance mass spectral results be consistent, above result shows
uGT74AC1catalysis momordica grosvenori alcohol and UDPG can react and generate Momordica-Glycosides I E.
Above specific embodiment of the invention case is described.Use the Grosvenor Momordica glycosyltransferase gene found in the present invention
uGT74AC1can with momordica grosvenori alcohol and UDPG for substrate catalysis generates Momordica-Glycosides
e.It is to be appreciated that the present invention is not limited to particular implementation described above, those skilled in the art can make various distortion or amendment in the scope of claim, and this does not affect flesh and blood of the present invention.
Claims (10)
1. a nucleotide sequence, is characterized in that described nucleotide sequence is from lower group:
there is the nucleotide sequence as shown in SEQ ID NO.1;
but the nucleotide sequence of encode peptide sequence SEQ ID NO.2 shown in different from the nucleotide sequence shown in SEQ ID NO.1;
with the Yuan≤85%(of Xu row Tong shown in sequence SEQ ID NO.1 preferably 95%), and there is the nucleotide sequence that catalysis momordica grosvenori alcohol produces sweet glucoside I E activity;
the nucleotide sequence of the sequence hybridization that can limit with sequence table SEQ ID NO.1 under high high stringency conditions
with
the nucleotide sequence of arbitrary described nucleotide sequence complementary.
2. a peptide sequence, is characterized in that described peptide sequence is selected from lower group:
there is the peptide sequence as shown in SEQ ID NO.2;
peptide sequence shown in SEQ ID NO.2 through replacement, lack or add one or several amino acid and have catalysis momordica grosvenori alcohol generate sweet glucoside I E activity by
derivative peptide sequence;
tong Yuan≤the 90%(of peptide sequence shown in peptide sequence and SEQ ID NO.2 preferably 95%), and have catalysis momordica grosvenori alcohol generate sweet glucoside I E activity by
derivative peptide sequence.
3. a recombinant expression vector, is characterized in that this expression vector contains nucleotide sequence according to claim 2.
4., according to the recombinant expression vector described in right 3, it is characterized in that it is pET21-UGT74AC1.
5. a genetically engineered host cell, is characterized in that it is the host cell and the progeny cell thereof that transform, expression vector described in right of having transduceed 3 or genome incorporate nucleotide sequence described in right 2.
6., according to the host cell described in right 5, it is characterized in that described host cell is the offspring of bacterial cell, fungal cell, zooblast or vegetable cell and these host cells.
7., according to the host cell described in right 6, it is characterized in that described host cell is Bacillus coli cells Rosetta gami (DE3).
8. the nucleotide sequence described in right 1, amino acid residue sequence according to claim 2 and the recombinant expression vector described in right 3 are applied to expression glycosyltransferase
uGT74AC1.
9. utilize the glycosyltransferase that claim 8 is expressed
uGT74AC1carry out enzyme reaction catalysis momordica grosvenori alcohol and UDPG to react and generate Momordica-Glycosides I E.
10. reaction system is: 50 mM Tris-HCL, 5 mM MgCl
2, 0.2 mM momordica grosvenori alcohol, 1 mM UDPG and 100 μ g purifying
uGT74AC1albumen, under 30 DEG C of conditions, reacts 4 h.
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Cited By (9)
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|---|---|---|---|---|
| CN105002193A (en) * | 2015-05-18 | 2015-10-28 | 安徽农业大学 | Flavonol 3-O-glucosyltransferase CsUGT78A14 gene and coding protein and application thereof |
| CN105063067A (en) * | 2015-05-18 | 2015-11-18 | 安徽农业大学 | Flavonol3-O-galactosyltransferase CsUGT78A15 gene, coding protein and applications thereof |
| CN105087612A (en) * | 2015-07-10 | 2015-11-25 | 安徽农业大学 | Flavonol multi-site glucosyltransferase CsUGT73A20 gene as well as coding protein and application thereof |
| CN105087613A (en) * | 2015-07-10 | 2015-11-25 | 安徽农业大学 | Flavonol 7-O-glucosyltransferase CsUGT75L12 gene as well as coding protein and application thereof |
| WO2016060276A1 (en) * | 2014-10-17 | 2016-04-21 | サントリーホールディングス株式会社 | Mogrol glycosyltransferase and gene encoding same |
| CN106350564A (en) * | 2015-07-20 | 2017-01-25 | 中国科学院天津工业生物技术研究所 | Synthesis method of terpenoid and glycosylation products thereof in synthesis route of mogrol |
| CN112760301A (en) * | 2019-11-01 | 2021-05-07 | 中国科学院天津工业生物技术研究所 | Glycosyltransferase mutant with improved catalytic activity and application thereof |
| CN114752577A (en) * | 2021-01-08 | 2022-07-15 | 桂林莱茵生物科技股份有限公司 | Momordica grosvenori-derived glycosyltransferase mutant and application thereof |
| CN115804429A (en) * | 2021-09-13 | 2023-03-17 | 桂林莱茵生物科技股份有限公司 | Fructus momordicae sugar-reduced juice powder and preparation method thereof |
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| WO2016060276A1 (en) * | 2014-10-17 | 2016-04-21 | サントリーホールディングス株式会社 | Mogrol glycosyltransferase and gene encoding same |
| US10689682B2 (en) | 2014-10-17 | 2020-06-23 | Suntory Holdings Limited | Mogrol glycosyltransferase and gene encoding same |
| US10407706B2 (en) | 2014-10-17 | 2019-09-10 | Suntory Holdings Limited | Mogrol glycosyltransferase and gene encoding same |
| CN105063067B (en) * | 2015-05-18 | 2018-10-12 | 安徽农业大学 | A kind of flavonols 3-O- galactosyltransferase CsUGT78A15 genes and its coding albumen and application |
| CN105002193A (en) * | 2015-05-18 | 2015-10-28 | 安徽农业大学 | Flavonol 3-O-glucosyltransferase CsUGT78A14 gene and coding protein and application thereof |
| CN105002193B (en) * | 2015-05-18 | 2018-10-12 | 安徽农业大学 | A kind of flavonols 3-O- glucosyltransferase CsUGT78A14 genes and its coding albumen and application |
| CN105063067A (en) * | 2015-05-18 | 2015-11-18 | 安徽农业大学 | Flavonol3-O-galactosyltransferase CsUGT78A15 gene, coding protein and applications thereof |
| CN105087613A (en) * | 2015-07-10 | 2015-11-25 | 安徽农业大学 | Flavonol 7-O-glucosyltransferase CsUGT75L12 gene as well as coding protein and application thereof |
| CN105087612A (en) * | 2015-07-10 | 2015-11-25 | 安徽农业大学 | Flavonol multi-site glucosyltransferase CsUGT73A20 gene as well as coding protein and application thereof |
| CN106350564A (en) * | 2015-07-20 | 2017-01-25 | 中国科学院天津工业生物技术研究所 | Synthesis method of terpenoid and glycosylation products thereof in synthesis route of mogrol |
| CN112760301A (en) * | 2019-11-01 | 2021-05-07 | 中国科学院天津工业生物技术研究所 | Glycosyltransferase mutant with improved catalytic activity and application thereof |
| CN112760301B (en) * | 2019-11-01 | 2023-01-17 | 中国科学院天津工业生物技术研究所 | Glycosyl transferase mutant with improved catalytic activity and application thereof |
| CN114752577A (en) * | 2021-01-08 | 2022-07-15 | 桂林莱茵生物科技股份有限公司 | Momordica grosvenori-derived glycosyltransferase mutant and application thereof |
| CN114752577B (en) * | 2021-01-08 | 2024-04-16 | 桂林莱茵生物科技股份有限公司 | Momordica grosvenori-derived glycosyltransferase mutant and application thereof |
| CN115804429A (en) * | 2021-09-13 | 2023-03-17 | 桂林莱茵生物科技股份有限公司 | Fructus momordicae sugar-reduced juice powder and preparation method thereof |
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