CN107144651A - Arctic Sea fuchsin coccus B7740 produces the Structural Identification method of isoprenoid - Google Patents
Arctic Sea fuchsin coccus B7740 produces the Structural Identification method of isoprenoid Download PDFInfo
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Abstract
The invention discloses the Structural Identification method that Arctic Sea fuchsin coccus B7740 produces isoprenoid, this method carries out Preliminary Identification using Liquid Chromatography/Mass Spectrometry to Arctic Sea fuchsin coccus B7740 production isoprenoids.This method is easy to operate, reliable results, stably, can Preliminary Identification go out in Rhodococcus sp B7740 production isoprenoid materials to include 9 Carotenoids and 14 isoprenoid quinones.
Description
Technical field
The invention belongs to the technical field of Rhodococcus sp B7740 production isoprenoid analyses, and in particular to Arctic Sea fuchsin ball
Bacterium B7740 produces the Structural Identification method of isoprenoid.
Background technology
Rhod is the gram-positive bacteria that a class is distributed widely in nature, in soil, bottom sediment and food grass
Rich content in animal wastes, and it is most for battalion's saprogenesis.Rhod (Rhodococcus sp.) be 1891 by
What Zoof was set up, from setting up so far, classification position is not known always.At present, Rhodococcus sp belongs to actinomyces door
(Actinobacteria), Actinomycetes (Actinobacteria), actinomyces subclass (Actinobacteridae), actinomyces
Mesh (Actinomycetales), bar bacterium suborder (Croynebacterineae), Nocardiaceae (Nocardiaceae) is red
Coccus (Rhodococcus).
At present, the research both at home and abroad to rhodococcus erythropolis is more, is concentrated mainly on the research of its biodegradability and molecule
Research is learned, and isoprenoid material is produced to Rhodococcus sp and studies less, it is different especially to produce class to the Rhodococcus sp that polar ocean is originated
The identification of pentadiene material is still very deficient with studying, and Rhodococcus sp B7740 is arctic scientific expedition of China in the scientific investigation of the third time arctic
When found from the surface seawater of 20 meters of B77 websites, for the bacterium institute product Quality Research and traditional isoprenoid material
Identification is different.The carotenoid in common higher plant source is given birth to according to oxygen-containing and without oxygen be two classes as animals and plants
Required pigment is grown, what is identified at present there are about 750 kinds, wherein there are about 250 kinds from Yu Haiyang, 40 kinds appear in people
Among class meals.Rhodococcus sp B7740 produces the metabolic pathway of carotenoids procatarxis microorganism uniqueness, comes with common higher plant
Source carotenoid is compared, and structure difference is larger, and structure species are not single, and its unique structure not give only its unique work
Property, also increase the difficulty for identifying its molecular structure.
The content of the invention
To solve the problem of above-mentioned prior art is present, class isoamyl is produced the invention provides Arctic Sea fuchsin coccus B7740
The Structural Identification method of diene, the authentication method is easy to operate, reliable results, stably.
Realize technical scheme that above-mentioned purpose of the present invention used for：
Arctic Sea fuchsin coccus B7740 produces the Structural Identification method of isoprenoid, using Liquid Chromatography/Mass Spectrometry to Arctic Sea
Fuchsin coccus B7740 production isoprenoids carry out Preliminary Identification.
Arctic Sea fuchsin coccus B7740 produces the Structural Identification method of isoprenoid, comprises the following steps：
1st, the preparation of isoprenoid testing sample：
In the sodium chloride solution that isoprenoid extract solution is added to 8-10wt%, isoprenoid extract solution and sodium chloride
The volume ratio of solution is 1:1, it is well mixed, obtains mixed liquor, mixed liquor is layered in 3-8 DEG C of centrifugation, a layer nonferrous layer is removed, will have
Chromatograph is dried, and again with methanol is 1 with methyl tertiary butyl ether(MTBE) volume ratio:1 mixed solvent redissolves, and uses filtering with microporous membrane, obtains
To isoprenoid testing sample；
2nd, the detection of isoprenoid testing sample：
Isoprenoid testing sample is detected using LC-MS instrument：
2.1st, liquid phase chromatogram condition：
Chromatographic column YMCC30,25 DEG C of column temperature, ultraviolet absorption detector, Detection wavelength 450nm and 242nm；
Mobile phase：Mobile phase A is methanol, and Mobile phase B is methyl tertiary butyl ether(MTBE), flow velocity：1ml/min；
Elution program：
First stage：30 minutes, the wherein volume basis of mobile phase A are eluted using the mixed liquor of mobile phase A and Mobile phase B
Content is changed into 70% from 95%, and the volumn concentration of Mobile phase B is changed into 30% from 5%；
Second stage：20 minutes, the wherein volume basis of mobile phase A are eluted using the mixed liquor of mobile phase A and Mobile phase B
Content is changed into 50% from 70%, and the volumn concentration of Mobile phase B is changed into 50% from 30%；
Phase III：10 minutes, the wherein volume basis of mobile phase A are eluted using the mixed liquor of mobile phase A and Mobile phase B
Content is changed into 95% from 50%, and the volumn concentration of Mobile phase B is changed into 5% from 50%；
2.2nd, Mass Spectrometry Conditions：
APCI ion guns, positive ion mode, 300 DEG C of ion source temperature, capillary voltage 350V, corona voltage 1V are dried
Air-flow 7L/min, is atomized 350 DEG C of room temperature, nebulizer pressure 10psi, mass-to-charge ratio scanning range 50-1200.
Further, in step 2.1, the rotating speed of centrifugation is 7000rpm, and the time is 10min.
Further, in step 2.1, the aperture of miillpore filter is 0.22 μm.
Compared with prior art, the advantages of the present invention are：
1st, isoprenoid includes isoprenoid quinones and carotenoid, is that the class being widely present in nature is natural
Active material.At present, the research for the isoprenoid originated for plant and part marine animal is gradually perfect, has reached extensively
Application stage, but microorganism (particularly marine microorganism) not yet has extensive as the huge source of isoprenoid material
Report and research.The strain that Rhodococcus sp B7740 has found first as the arctic scientific investigation of China's third time, it produces isoprenoid thing
Matter content is higher, species it is abundant, it is necessary to identification that we carry out structure with the method for chemical analysis to it and primary product it is pure
Change.Agilent1100Series LC-MSD-Trap-XCT preliminary determining methods used of the invention, analysis is quick, reliable results,
It is stable, it is suitable as analyzing the preliminary determining method that Rhodococcus sp B7740 produces carotenoid.
2nd, the present invention can Preliminary Identification go out Rhodococcus sp B7740 production isoprenoid material in include 9 Carotenoids and 14
Isoprenoid quinone.
Figure of description
Fig. 1 is that Arctic Sea fuchsin coccus B7740 produces chromatograms of the isoprenoid material at 242nm.
Fig. 2 is that Arctic Sea fuchsin coccus B7740 produces chromatograms of the isoprenoid material at 450nm.
Fig. 3 A are the ultraviolet absorpting spectrum at No. 1 peak.
Fig. 3 B are the second order mses collection of illustrative plates at No. 1 peak.
Fig. 4 A are the ultraviolet absorpting spectrum at No. 11 peaks.
Fig. 4 B are the second order mses collection of illustrative plates at No. 11 peaks.
Fig. 5 A are the ultraviolet absorpting spectrum at No. 17 peaks.
Fig. 5 B are the second order mses collection of illustrative plates at No. 17 peaks.
Fig. 6 A are the ultraviolet absorpting spectrum at No. 20 peaks.
Fig. 6 B are the second order mses collection of illustrative plates at No. 20 peaks.
Fig. 7 A are the ultraviolet absorpting spectrum at No. 21 peaks.
Fig. 7 B are the second order mses collection of illustrative plates at No. 21 peaks.
Embodiment
With reference to specific embodiment, the present invention is described in detail.
Arctic Sea fuchsin coccus B7740 is inventor during the 7-9 months in 2008 Chinese third time Chinese Arctic Research Expeditions,
With Seabird911 Plus CTD systems from Sea Surface deep Arctic Ocean B77 websites (146 ° of 49.28 ' W, 76 ° of 58.08 ' N) 25m
Isolated in water sample, Ningbo City microorganism is compared online with environmental project key lab by 16S rDNA sequence Bs last
It is right, judge the bacterium as Rhod.
Embodiment 1
The Structural Identification experiment of Arctic Sea fuchsin coccus B7740 production isoprenoids
1st, experiment material
1.1st, experiment reagent
Lysozyme (20000U/mg) is purchased from Chemical Reagent Co., Ltd., Sinopharm Group, zinc acetate, sodium chloride, methanol and two
Chloromethanes is purchased from Chemical Reagent Co., Ltd., Sinopharm Group, and hplc grade methanol is purchased from silent winged scientific and technological (China) the limited public affairs of generation that of match
Department, chromatographic grade methyl tertiary butyl ether(MTBE) is purchased from Shanghai Aladdin biochemical technology limited company, beta carotene standard items (97%)
It is purchased from sigma companies of the U.S..
1.2nd, laboratory apparatus
The Series LC-MSD-Trap-XCT LC-MSs instrument of Agilent 1100 is purchased from Agilent company；
The desk-top refrigerated centrifuges of Centrifuge 5810R are purchased from EPPENDORF companies of Germany.
1.3rd, experimental raw
According to Chinese patent (a kind of microcapsule preparation method of Rhodococcus sp B7740 carotenoid, 201510016005.8)
Disclosed method prepares isoprenoid extract solution：
The lyophilized bacterium powders (Wanli College, Zhejiang's offer) of 0.8g Arctic Sea fuchsin coccuses B7740 are weighed to be placed in centrifuge tube, plus
Enter 16ml lysozyme solns (1mg/ml), centrifuge tube is placed in 37 DEG C of water-baths, avoid light place 1h, then add 24ml saturation vinegar
Sour zinc solution settles the Rhodococcus sp of broken wall, by the centrifuge tube in centrifuging 10min at 7000rpm, 4 DEG C, abandons supernatant, then
By 64ml mixed organic solvents (methanol：Dichloromethane=4:1, volume ratio) it is added in Rhodococcus sp precipitation, stirred with glass bar
Uniformly, centrifuge, isolate supernatant, continue to add mixed organic solvents (methanol into centrifuge tube：Dichloromethane=4:1, volume
Than), so extract 2-3 times repeatedly, merge supernatant, obtain isoprenoid extract solution.
2nd, experimental method
2.1st, the preparation of isoprenoid testing sample：
60ml isoprenoids extract solution is added in 60ml 10wt% sodium chloride solutions, is well mixed, obtains mixed liquor,
By mixed liquor in 7000rpm, 4 DEG C of centrifugation layerings, a layer nonferrous layer is removed, nonferrous layer is dried up with nitrogen, then with 2ml methanol and first
(volume ratio of methanol and methyl tertiary butyl ether(MTBE) is 1 to the mixed solvent of base tertbutyl ether:1) redissolve, and with 0.22 μm of miillpore filter
Filtering, obtains about 1.5ml testing samples.
2.2nd, the detection of isoprenoid testing sample：
Isoprenoid testing sample is detected using LC-MS instrument：
2.2.1, liquid phase chromatogram condition：
Chromatographic column YMCC30 (5um × 4.6mm × 150mm), 25 DEG C of column temperature, ultraviolet absorption detector, Detection wavelength
450nm, sample size 10uL；
Mobile phase：Mobile phase A is methanol, and B is methyl tertiary butyl ether(MTBE)；
Elution program：
First stage：30 minutes, the wherein volume basis of mobile phase A are eluted using the mixed liquor of mobile phase A and Mobile phase B
Content is changed into 70% from 95%, and the volumn concentration of Mobile phase B is changed into 30% from 5%；
Second stage：20 minutes, the wherein volume basis of mobile phase A are eluted using the mixed liquor of mobile phase A and Mobile phase B
Content is changed into 50% from 70%, and the volumn concentration of Mobile phase B is changed into 50% from 30%；
Phase III：10 minutes, the wherein volume basis of mobile phase A are eluted using the mixed liquor of mobile phase A and Mobile phase B
Content is changed into 95% from 50%, and the volumn concentration of Mobile phase B is changed into 5% from 50%；
2.2.2, Mass Spectrometry Conditions：
APCI ion guns, positive ion mode, 300 DEG C of ion source temperature, capillary voltage 350V, corona voltage 1V are dried
Air-flow 7L/min, is atomized 350 DEG C of room temperature, nebulizer pressure 10psi, mass-to-charge ratio scanning range 50-1200.
3rd, experimental result：
Under Detection wavelength 242 and 450nm, two liquid chromatograms are occurred in that respectively, and Fig. 1 is Rhodococcus sp under 242nm
B7740 produces the liquid chromatogram collection of illustrative plates of isoprenoid material, and Fig. 2 is Rhodococcus sp B7740 production isoprenoid materials under 450nm
Liquid chromatogram collection of illustrative plates, is numbered respectively according to peak sequence, and 10 peaks, respectively 1,2,3,4,5,6,9,11,13 are occurred in that in Fig. 1
With No. 15 peaks, occur in that 14 peaks in Fig. 2, respectively 7,8,10,11,12,13,16,17,18,19,20,21,22 and No. 23
Peak.
3.1st, isoprenoid quinones is analyzed and identified：
No. 1 peak is through analysis, as can be seen that secondly there is m/z=197 feature in level mass spectrogram from Fig. 3 A, Fig. 3 B and table 1
At fragment ion, its ultraviolet characteristic absorption peak 258nm, and hydrogenated molecule quasi-molecular ions m/z=455, therefore, judge No. 1 peak to be general
Quinones substance UQ4.
2nd, No. 3 peaks are through analysis, from table 1 it follows that secondly having m/z=187's (methylnaphthoquinone) in level mass spectrogram
Fragments characteristic quasi-molecular ions, their hydrogenated molecule quasi-molecular ions m/z is respectively 717,649, while ultraviolet characteristic absorption peak is all concentrated
At 242nm, therefore, judgement 2, No. 3 peaks are respectively methylnaphthoquinone MK8、MK7。
4th, 6,7 and No. 13 peaks are through analysis, from table 1 it follows that secondly having m/z=187 (methyl naphthalenes in level mass spectrogram
Quinone) fragments characteristic quasi-molecular ions, compared with No. 2 peaks, its ultraviolet characteristic absorption peak red shift, respectively 248nm, 244nm,
244nm, 248nm, their hydrogen molecular ion peak m/z is 717, therefore, judge 4,6,7 and No. 13 peaks be the same of No. 2 peaks
Enantiomers, are methylnaphthoquinone MK8。
No. 8 peaks are through analysis, from table 1 it follows that secondly level mass spectrogram has m/z=187 (methylnaphthoquinone) feature broken
Piece quasi-molecular ions, compared with No. 3 peaks, its ultraviolet characteristic absorption peak red shift, is 246nm, and its hydrogen molecular ion peak m/z is 649,
Therefore, judge isomer of No. 8 peaks as No. 3 peaks, be methylnaphthoquinone MK7。
5 and No. 11 peaks are through analysis, as can be seen that secondly level mass spectrogram has m/z=187 from table 1, Fig. 4 A and Fig. 4 B
The fragments characteristic quasi-molecular ions of (methylnaphthoquinone), compared with No. 3 peaks, its ultraviolet characteristic absorption peak red shift, respectively 248nm,
244nm, its hydrogenated molecule quasi-molecular ions m/z add 4,2Da respectively, and respectively 653,651, therefore, it is concluded that it is MK7It is different
Hydrogenation products on pentadiene chain, respectively MK7(H4)、MK7(H2)。
9 and No. 15 peaks are through analysis, as it can be seen from table 1 secondly level mass spectrogram has the feature of m/z=187 (methylnaphthoquinone)
Fragment ion peak, compared with No. 2 peaks, its red shift of ultraviolet characteristic absorption peak, respectively 254nm, 248nm, its hydrogenated molecule
Quasi-molecular ions m/z adds 4,2Da respectively, and it is the hydrogenation products on MK8 isoprene chains, MK to infer it8On isoprene chain
Hydrogenation products, respectively MK8(H4)、MK8(H2)。
14th, from detection data preliminary judgement, it is also isoprenoid quinones at No. 18 peaks.
The LC-MS instrument detection data at above-mentioned peak are as shown in table 1：
Table 1：Rhodococcus sp B7740 produces the appearance time of isoprenoid quinones, ultraviolet characteristic peak and mass spectrometric data
From the foregoing, 1,2,3,4,5,6,7,8,9,11,13,14, the material corresponding to 15 and No. 18 peaks be that class is different
Pentadiene quinone.
3.2nd, carotenoid is analyzed and identified：
No. 17 peaks can be seen that secondly level mass spectrogram has m/z=163 (C through analysis from table 2, Fig. 5 A, Fig. 5 A10H12O2+
H fragments characteristic quasi-molecular ions), its ultraviolet characteristic absorption peak is respectively at 274nm, 452nm, 468nm, and it is hydrogenated with quasi-molecular ions m/z
=589, therefore, judge No. 17 peaks as all-trans-synechoxanthin (χ, χ-caroten-18,18'-dioic
acid)。
10th, No. 12 peaks are through analysis, from table 2 it can be seen that secondly level ms fragment is consistent with No. 17 peaks, because of its UV absorption
Contain the cis-structure characteristic absorption peak 340 or so in collection of illustrative plates, judge it for cis-synechoxanthin.
No. 19 peaks are shown in Table 2 through analysis, specific data, by No. 19 peaks and ultraviolet absorpting spectrum, the liquid of beta carotene standard items
Phase collection of illustrative plates and second order mses figure are contrasted, it is found that both collection of illustrative plates are consistent substantially, therefore, judged No. 19 peaks as β-Hu Luo
Bu Su.
No. 16 peaks are through analysis, from table 2 it can be seen that secondly level ms fragment is consistent with No. 19 peaks, because of its UV absorption figure
Contain the cis-structure characteristic absorption peak 340 or so in spectrum, judge it for cis- β-carotene.
No. 20 peaks can be seen that secondly level mass spectrogram has m/z=413 [M+H-C through analysis from table 2, Fig. 6 A, Fig. 6 A9H12]
Fragments characteristic quasi-molecular ions, ultraviolet characteristic absorption peak is at 460nm, hydrogenated molecule quasi-molecular ions m/z=533, therefore, judge No. 20
Peak is chlorobactene (φ, ψ-carotene).
No. 21 peaks can be seen that secondly level mass spectrogram has m/z=409 [M+H-C through analysis from table 2, Fig. 7 A, Fig. 7 A9H12]
Fragments characteristic quasi-molecular ions, UV, visible light characteristic absorption peak at 282nm, 452nm, 476nm, hydrogenated molecule quasi-molecular ions be m/z
=529, therefore, judge No. 21 peaks as isorenieratene (φ, φ-carotene).
22nd, from detection data preliminary judgement, it is also carotenoid at No. 23 peaks.
The LC-MS instrument detection data at above-mentioned peak are as shown in table 2：
From the foregoing, 10,12,16,17,19,21,22, the material corresponding to No. 23 peaks be carotenoid.
Claims (4)
1. Arctic Sea fuchsin coccus B7740 produces the Structural Identification method of isoprenoid, it is characterised in that：Using Liquid Chromatography/Mass Spectrometry
Arctic Sea fuchsin coccus B7740 production isoprenoids are identified.
2. Arctic Sea fuchsin coccus B7740 according to claim 1 produces the Structural Identification method of isoprenoid, its feature
It is to comprise the following steps：
2.1st, the preparation of isoprenoid testing sample：
In the sodium chloride solution that isoprenoid extract solution is added to 8-10wt%, isoprenoid extract solution and sodium chloride solution
Volume ratio be 1:1, it is well mixed, obtains mixed liquor, mixed liquor is layered in 3-8 DEG C of centrifugation, a layer nonferrous layer is removed, by nonferrous layer
Dry, again with methanol is 1 with methyl tertiary butyl ether(MTBE) volume ratio:1 mixed solvent redissolves, and uses filtering with microporous membrane, obtains class
Isoprene testing sample；
2.2nd, the detection of isoprenoid testing sample：
Isoprenoid testing sample is detected using LC-MS instrument：
2.2.1, liquid phase chromatogram condition：
Chromatographic column YMC C30,25 DEG C of column temperature, ultraviolet absorption detector, Detection wavelength 450nm and 242nm；
Mobile phase：Mobile phase A is methanol, and Mobile phase B is methyl tertiary butyl ether(MTBE), flow velocity：1ml/min；
Elution program：
First stage：30 minutes, the wherein volumn concentration of mobile phase A are eluted using the mixed liquor of mobile phase A and Mobile phase B
It is changed into 70% from 95%, the volumn concentration of Mobile phase B is changed into 30% from 5%；
Second stage：20 minutes, the wherein volumn concentration of mobile phase A are eluted using the mixed liquor of mobile phase A and Mobile phase B
It is changed into 50% from 70%, the volumn concentration of Mobile phase B is changed into 50% from 30%；
Phase III：10 minutes, the wherein volumn concentration of mobile phase A are eluted using the mixed liquor of mobile phase A and Mobile phase B
It is changed into 95% from 50%, the volumn concentration of Mobile phase B is changed into 5% from 50%；
2.2.2, Mass Spectrometry Conditions：
APCI ion guns, positive ion mode, 300 DEG C of ion source temperature, capillary voltage 350V, corona voltage 1V, dry gas stream
7L/min, is atomized 350 DEG C of room temperature, nebulizer pressure 10psi, mass-to-charge ratio scanning range 50-1200.
3. Arctic Sea fuchsin coccus B7740 according to claim 2 produces the Structural Identification method of isoprenoid, it is special
Levy and be：In step 2.1, the rotating speed of centrifugation is 7000rpm, and the time is 10min.
4. the Arctic Sea fuchsin coccus B7740 according to profit requires 2 produces the Structural Identification method of isoprenoid, its feature
It is：In step 2.1, the aperture of miillpore filter is 0.22 μm.
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| JP2004233312A (en) * | 2003-02-03 | 2004-08-19 | Sumitomo Chem Co Ltd | B vitamin a, inducer of the same and analysis method of carotenoid |
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