CN104894080B - A kind of flavonoids prenyltransferase AhFDT3 and its encoding gene and application - Google Patents
A kind of flavonoids prenyltransferase AhFDT3 and its encoding gene and application Download PDFInfo
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Abstract
The invention discloses a kind of flavonoids prenyltransferase AhFDT3 and its encoding gene and application.Present invention clone from jackfruit obtains flavonoids isopentenyl transferase genes AhFDT3, and its nucleotide sequence is as shown in SEQ ID NO.1；The flavonoids prenyltransferase AhFDT3 of coding, its amino acid sequence is as shown in SEQ ID NO.2.By using flavonoids isopentenyl transferase genes AhFDT3 construction of expression vector transformed saccharomyces cerevisiaes, acquisition overexpression flavonoids prenyltransferase AhFDT3 saccharomyces cerevisiae；Using its bacterium solution or microsome catalysis isopentene group donor and flavonoids substrate synthesis isopentene group flavonoids, conversion ratio may be up to 27%, and product purity is up to 76 90%.The present invention provides a kind of new method for the biosynthesis of isopentene group flavonoids, has easy to operate, small, the advantage such as product purity height of reaction pollution.
Description
Technical field
The invention belongs to biological technical field, and in particular to a kind of flavonoids prenyltransferase AhFDT3 and its coding
Gene and application.
Background technology
Jackfruit (Artocarpus heterophyllus Lam.) belongs to Moraceae fruit plant, mainly plants in heat
Band, subtropical area.Fruit aromatic flavour, sweet and sour taste are deep to be favored by south China consumer.Jackfruit is not only one kind
Characteristic fruit resource, its branches and leaves tissue are rich in the Flavonoid substances of a kind of special construction, i.e. isopentene group flavonoids.This kind of flavones
Class material is more stronger than the bioactivity of flavones substance of common structure, such as it is suppressing proliferative activity o f tumor, immune tune
Activity etc. is saved, the Flavonoid substances than no isopentene group are more notable.Isopentene group flavonoids in jackfruit tissue
Content it is not only high, and structure species enrich, and have now been found that the iso-amylene base class of more than 20 kind different structure forms is yellow
Ketone.As can be seen here, jackfruit is both abundant isopentene group flavonoids natural resources, and flavonoids prenyltransferase
Affluent resources.Isopentene group flavonoids has very important value in terms of the disease treatments such as tumour, has a wide range of applications
Prospect.Therefore, using the intrinsic inherent advantage of jackfruit, a kind of biosynthesis iso-amylene is developed by the means of biotechnology
The method of base class flavones is by with important industrial value.
The content of the invention
First purpose of the present invention is to provide a kind of flavonoids prenyltransferase AhFDT3 and its encoding gene
AhFDT3。
The flavonoids prenyltransferase AhFDT3 of the present invention, its amino acid sequence is as shown in SEQ ID NO.2.
Present invention also offers the flavonoids isopentene group transfer for encoding above-mentioned flavonoids prenyltransferase AhFDT3
Enzyme gene AhFDT3, its nucleotide sequence is as shown in SEQ ID NO.1.
Second object of the present invention is to provide flavonoids prenyltransferase AhFDT3 and is preparing iso-amylene base class Huang
Application in ketone.
Described application is preferably to add apiolin into expression flavonoids prenyltransferase AhFDT3 saccharomyces cerevisiae
In bacterium solution, it is catalyzed through flavonoids prenyltransferase AhFDT3 and produces isopentene group apiolin.
Described application is preferably using flavonoids and isopentene group donor as substrate, through flavonoids prenyltransferase
AhFDT3 catalysis produces isopentene group flavonoids.
It is preferred that described catalysis, the pH value of its reaction system is 7~9, and reaction temperature is 20~40 DEG C.
It is preferred that described flavonoids is apiolin, described isopentene group donor is dimethyl propylene alkenyl pyrophosphoric acid, through class
Flavones prenyltransferase AhFDT3 catalysis produces isopentene group apiolin.
It is preferred that described flavonoids is Kaempferol, described isopentene group donor is dimethyl propylene alkenyl pyrophosphoric acid, through class
Flavones prenyltransferase AhFDT3 catalysis produces isopentene group Kaempferol.
Present invention clone from jackfruit obtains flavonoids isopentenyl transferase genes AhFDT3, its flavonoids encoded
Prenyltransferase AhFDT3 has the good activity for catalyzing and synthesizing isopentene group flavonoids.By using flavonoids isoamyl
Alkenyl transferase gene AhFDT3 construction of expression vector transformed saccharomyces cerevisiaes, obtain overexpression flavonoids prenyltransferase
AhFDT3 saccharomyces cerevisiae；Utilize its bacterium solution or microsome catalysis isopentene group donor and flavonoids substrate synthesis iso-amylene base class
Flavones, conversion ratio may be up to 27%, and product purity is up to 76-90%.The present invention carries for the biosynthesis of isopentene group flavonoids
A kind of new method has been supplied, there is easy to operate, small, the advantage such as product purity height of reaction pollution.
Brief description of the drawings
Fig. 1 is the first mass spectrometric figure of isopentene group apiolin.
Fig. 2 is the second order mses figure of isopentene group apiolin.
Fig. 3 is the bacterium colony PCR primer electrophoretogram of saccharomyces cerevisiae positive bacteria.
Fig. 4 is the first mass spectrometric figure of isopentene group Kaempferol.
Fig. 5 is the second order mses figure of isopentene group Kaempferol.
Embodiment
Following examples are to further explanation of the invention, rather than limitation of the present invention.
The experimental method not indicated specifically in following Examples, can conventionally be carried out.
Embodiment 1：Clone flavonoids isopentenyl transferase genes AhFDT3, structure overexpression vector and conversion wine brewing ferment
It is female
The RNA of jackfruit blade is extracted, using reverse transcriptase M-MLV, the cDNA of reverse transcription reaction synthesis.Using the cDNA as
Template, using forward primer GCCACCATGGCTCAAGTTGG, reverse primer TATGAGTGGAAATATTATATACTCTGCAT,
TakaRa companies Ex Taq archaeal dna polymerases, enter performing PCR amplification；PCR conditions are：94 DEG C, 5min；94 DEG C, 45s, 56 DEG C,
1min, 72 DEG C, 1.5min；35 circulations；72 DEG C of extension 10min.Purpose fragment is reclaimed using agarose gel electrophoresis, by purpose
Fragment delivers sequencing.Through sequencing analysis, clone obtains flavonoids isopentenyl transferase genes AhFDT3, and its nucleotide sequence is such as
Shown in SEQ ID NO.1, it contains 1191 bases, and the albumen of coding is named as flavonoids prenyltransferase AhFDT3,
Totally 396 amino acid, specific amino acid sequence is as shown in SEQ ID NO.2.
Connection flavonoids isopentenyl transferase genes AhFDT3 to overexpression vector pYes2.1TOPO (is purchased from
Invitrogen companies, article No. K4150-01) on, coupled reaction condition is：Flavonoids isopentenyl transferase genes AhFDT3,
Plasmid pYes2.1TOPO, 1.2M NaCl, 0.06M MgCl2After mixing, room temperature places 30min and completes coupled reaction, is weighed
(flavonoids isopentenyl transferase genes AhFDT3 is inserted into the restructuring matter after overexpression vector pYes2.1TOPO to group plasmid
Grain).Then recombinant plasmid is converted into Saccharomyces cerevisiae competent cell again, conversion condition is：Into competent yeast cells
2 μ L recombinant plasmids, 5 μ L salmon sperm dnas are added, are mixed；Adding 600 μ L conversion fluids, (converting formula of liquid is：1mL 50%PEG,
125 μ L 10 × TE, 125 10 × LiAc of μ L), 30 DEG C, 100rpm shaking tables conversion 30min；Adding 70 μ L DMSO, (dimethyl is sub-
Sulfone), 42 DEG C of heat shock 15min；Ice bath places 13000rpm centrifugation 5s after 2min, adds 200 μ L 1 × TE suspension cells, is coated with SC-U
Suppress flat board, 30 DEG C are cultivated 3~5 days.Bacterium colony PCR screens recombinant plasmid successful conversion to the positive bacteria of brewing yeast cell, sieve
Choosing method is：Select single bacterium colony and be transferred to 50 μ L sterilized waters, 100 DEG C of heating 5min, centrifugation removes cell fragment；Take on 10 μ L
Clear liquid, add 5 μ L Ex Taq DNA polymerase buffers liquid, 1 μ L 10mM dNTPs, 1 μ L forward primers
GCCACCATGGCTCAAGTTGG, 1 μ L reverse primer ACCGAGGAGAGGGTTAGGGAT, 0.5 μ L Ex from plasmid sequence
Taq archaeal dna polymerases, 31.5 μ L sterilized waters, mixing；PCR programs are：94 DEG C, 5min；94 DEG C, 40s；56 DEG C, 40s；72 DEG C,
1.5min；35 circulations；72 DEG C of extension 10min.PCR primer is detected with agarose gel electrophoresis, as a result as shown in figure 3, Fig. 3
M is marker, and 1 is positive bacteria, and the positive bacteria can amplify purpose fragment, shows flavonoids isopentenyl transferase genes
AhFDT3 is inserted into the recombinant plasmid successful conversion after overexpression vector pYes2.1TOPO to brewing yeast cell, then through sequencing
Checking confirms, thus obtains flavonoids isopentenyl transferase genes AhFDT3 being inserted into overexpression vector pYes2.1TOPO
Recombinant plasmid successful conversion afterwards is named as saccharomyces cerevisiae pYes2.1TOPO-AhFDT3 to the positive bacteria of brewing yeast cell.
Mass propgation is carried out to saccharomyces cerevisiae pYes2.1TOPO-AhFDT3, chooses saccharomyces cerevisiae pYes2.1TOPO-AhFDT3 transfers first
Suppress culture medium (2% glucose is carbon source) to 50mL SC-U, 30 DEG C, 200rpm, cultivate to exponential phase；It is collected by centrifugation
Cell, OD600=0.4 is diluted to SC-U inducing cultures (2% galactolipin, 1% gossypose are carbon source), 30 DEG C, 200rpm,
Cultivate 24h.With SC-U inducing culture culture saccharomyces cerevisiae pYes2.1TOPO-AhFDT3, induce its overexpression flavonoids different
Amylene based transferase AhFDT3, that is, obtain overexpression flavonoids prenyltransferase AhFDT3 saccharomyces cerevisiae bacterium solution.
Embodiment 2：Synthesize flavonoids isopentenyl transferase genes AhFDT3, structure overexpression vector and conversion wine brewing ferment
It is female
Flavonoids isopentenyl transferase genes AhFDT3 full length sequences are directly synthesized (specifically such as using fully synthetic method
Shown in SEQ ID NO.1), flavonoids isopentenyl transferase genes AhFDT3 is connected to overexpression according to the method for embodiment 1
On carrier pYes2.1TOPO, then convert into Saccharomyces cerevisiae competent cell, obtain saccharomyces cerevisiae pYes2.1TOPO-
AhFDT3.Saccharomyces cerevisiae pYes2.1TOPO-AhFDT3 is subjected to mass propgation, induction overexpression flavonoids isopentene group turns
Enzyme AhFDT3 is moved, obtains overexpression flavonoids prenyltransferase AhFDT3 saccharomyces cerevisiae bacterium solution.
Embodiment 3：The biosynthesis of isopentene group apiolin
1. synthesize isopentene group apiolin
500 μ are added in the overexpression flavonoids prenyltransferase AhFDT3 of embodiment 1 saccharomyces cerevisiae bacterium solution
M apiolins, after 25 DEG C are reacted 48 hours, extracted using the ethanol solution of volume fraction 90%, ethanol mutually passes through C18 reversed-phase columns
(16mm × 460mm) is purified, with methanol：Water (50/50~100/0) elutes, and collects the elution that methanol/water volume ratio is 90/10
Component, obtain compound 1 (isopentene group apiolin).
2. the Structural Identification of compound 1 (isopentene group apiolin)
Compound 1 dissolves in methanol, and first mass spectrometric result is shown [M+H]+M/z=339.1, as shown in figure 1, showing the change
Adduct molecule amount is 338, than the molecular weight that apiolin has more an isopentene group.Second order mses generate two fragments, and m/z divides
Not Wei 283.1 and 165.1, as shown in Figure 2, it was demonstrated that the isopentene group is connected on the A rings of apiolin.Thereby confirm that compound 1
For isopentene group apiolin.
The conversion ratio of method synthesis isopentene group apiolin of the present embodiment is used as 11%, purity 76%.
Embodiment 4：The biosynthesis of isopentene group apiolin
500 μ are added in the overexpression flavonoids prenyltransferase AhFDT3 of embodiment 1 saccharomyces cerevisiae bacterium solution
M apiolins, 35 DEG C reaction 2 hours after, using the ethanol solution of volume fraction 60% extract, by C18 reversed-phase columns (16mm ×
460mm) purify, with methanol：Water (50/50~100/0) elutes, and collects the elution fraction that methanol/water volume ratio is 90/10, obtains
To isopentene group apiolin.Using the conversion ratio of method synthesis isopentene group apiolin of the present embodiment, purity is for 6%
82%.
Embodiment 5：The biosynthesis of isopentene group apiolin
500 μ are added in the overexpression flavonoids prenyltransferase AhFDT3 of embodiment 1 saccharomyces cerevisiae bacterium solution
M apiolins, 30 DEG C reaction 24 hours after, using the ethanol solution of volume fraction 80% extract, by C18 reversed-phase columns (16mm ×
460mm) purify, with methanol：Water (50/50~100/0) elutes, and collects the elution fraction that methanol/water volume ratio is 90/10, obtains
To isopentene group apiolin.Using the conversion ratio of method synthesis isopentene group apiolin of the present embodiment, purity is for 19%
79%.
Embodiment 6：The biosynthesis of isopentene group apiolin
It is collected by centrifugation in the overexpression flavonoids prenyltransferase AhFDT3 saccharomyces cerevisiae bacterium solution of embodiment 2
Bacterial strain, extract microsome；100 μ g microsomes are taken, add 100mM Tris-HCl (pH7.0), 10mM Mg2+、500μM DMAPP
(dimethyl propylene alkenyl pyrophosphoric acid), 500 μM of apiolins, after 20 DEG C are reacted 0.5 hour, using ethyl acetate extractive reaction liquid, second
Acetoacetic ester is mutually purified by C18 reversed-phase columns (16mm × 460mm), with methanol：Water (50/50~100/0) elutes, and collection methanol/
Water volume ratio is 90/10 elution fraction, obtains isopentene group apiolin (structure determination of the compound is with embodiment 3).Adopt
The conversion ratio that isopentene group apiolin is synthesized with the method for the present embodiment is 19%, purity 90%.
Embodiment 7：The biosynthesis of isopentene group apiolin
It is collected by centrifugation in the overexpression flavonoids prenyltransferase AhFDT3 saccharomyces cerevisiae bacterium solution of embodiment 1
Bacterial strain, extract microsome；100 μ g microsomes are taken, add 100mM Tris-HCl (pH9.0), 10mM Mg2+、500μM DMAPP
(dimethyl propylene alkenyl pyrophosphoric acid), 500 μM of apiolins, after 40 DEG C are reacted 24 hours, using ethyl acetate extractive reaction liquid, acetic acid
Ethyl ester is mutually purified by C18 reversed-phase columns (16mm × 460mm), with methanol：Water (50/50~100/0) elutes, and collects methanol/water
Volume ratio is 90/10 elution fraction, obtains isopentene group apiolin.Isopentene group celery is synthesized using the method for the present embodiment
The conversion ratio of element is 12%, purity 89%.
Embodiment 8：The biosynthesis of isopentene group apiolin
It is collected by centrifugation in the overexpression flavonoids prenyltransferase AhFDT3 saccharomyces cerevisiae bacterium solution of embodiment 1
Bacterial strain, extract microsome；100 μ g microsomes are taken, add 100mM Tris-HCl (pH8.0), 10mM Mg2+、500μM DMAPP
(dimethyl propylene alkenyl pyrophosphoric acid), 500 μM of apiolins, after 30 DEG C are reacted 24 hours, using ethyl acetate extractive reaction liquid, acetic acid
Ethyl ester is mutually purified by C18 reversed-phase columns (16mm × 460mm), with methanol：Water (50/50~100/0) elutes, and collects methanol/water
Volume ratio is 90/10 elution fraction, obtains isopentene group apiolin.Isopentene group celery is synthesized using the method for the present embodiment
The conversion ratio of element is 25%, purity 87%.
Embodiment 9：The biosynthesis of isopentene group Kaempferol
1. synthesize isopentene group Kaempferol
It is collected by centrifugation in the overexpression flavonoids prenyltransferase AhFDT3 saccharomyces cerevisiae bacterium solution of embodiment 1
Bacterial strain, extract microsome；100 μ g microsomes are taken, add 100mM Tris-HCl (pH8.0), 10mM Mg2+、500μM DMAPP
(dimethyl propylene alkenyl pyrophosphoric acid), 500 μM of Kaempferols, after 30 DEG C are reacted 24 hours, using ethyl acetate extractive reaction liquid, acetic acid
Ethyl ester is mutually purified by C18 reversed-phase columns (16mm × 460mm), with methanol：Water (50/50~100/0) elutes, and obtains compound 2
(isopentene group Kaempferol).
2. the Structural Identification of compound 2 (isopentene group Kaempferol)
Compound 2 dissolves in methanol, and first mass spectrometric result is shown [M+H]+M/z=355.1, as shown in figure 3, showing the change
The molecular weight of compound 2 is 354, than the molecular weight that Kaempferol has more an isopentene group.Second order mses generate a fragment, m/z
For 299.1, as shown in figure 4, showing due to Kaempferol fragment caused by the fracture of isopentene group.It is different to thereby determine that compound 2
Pentenyl Kaempferol.
The conversion ratio of method synthesis isopentene group Kaempferol of the present embodiment is used as 27%, purity 85%.
Claims (8)
- A kind of 1. flavonoids prenyltransferase AhFDT3, it is characterised in that its amino acid sequence such as SEQ ID NO.2 institutes Show.
- A kind of 2. flavonoids prenyltransferase for encoding the flavonoids prenyltransferase AhFDT3 described in claim 1 Gene, it is characterised in that its nucleotide sequence is as shown in SEQ ID NO.1.
- 3. applications of the flavonoids prenyltransferase AhFDT3 in isopentene group flavonoids is prepared described in claim 1.
- 4. application according to claim 3, it is characterised in that apiolin is added into expression flavonoids prenyltransferase In AhFDT3 saccharomyces cerevisiae bacterium solution, it is catalyzed through flavonoids prenyltransferase AhFDT3 and produces isopentene group apiolin.
- 5. application according to claim 3, it is characterised in that be that substrate, warp are used as using flavonoids and isopentene group donor Flavonoids prenyltransferase AhFDT3 catalysis produces isopentene group flavonoids.
- 6. application according to claim 5, it is characterised in that described catalysis, the pH value of its reaction system is 7~9, instead It is 20~40 DEG C to answer temperature.
- 7. application according to claim 5, it is characterised in that described flavonoids is apiolin, described isopentene group Donor is dimethyl propylene alkenyl pyrophosphoric acid, is catalyzed through flavonoids prenyltransferase AhFDT3 and produces isopentene group apiolin.
- 8. application according to claim 5, it is characterised in that described flavonoids is Kaempferol, described isopentene group Donor is dimethyl propylene alkenyl pyrophosphoric acid, is catalyzed through flavonoids prenyltransferase AhFDT3 and produces isopentene group Kaempferol.
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| CN113817698B (en) * | 2021-09-18 | 2023-08-25 | 江南大学 | Flavone 8-isopentenyl transferase from Korean epimedium and application thereof |
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| 乌拉尔甘草黄酮异戊烯基转移酶研究;李建华;《中国博士学位论文全文数据库.医药卫生科技辑》;20150115(第1期);引言、第1页第1节、第2页第3节、第15页第2段、第79-84页第2.2节、第110页第3.2.2节 * |
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