CN107843663A - A kind of discrimination method of Morinda officinalis oligosaccharide composition - Google Patents
A kind of discrimination method of Morinda officinalis oligosaccharide composition Download PDFInfo
- Publication number
- CN107843663A CN107843663A CN201710996983.2A CN201710996983A CN107843663A CN 107843663 A CN107843663 A CN 107843663A CN 201710996983 A CN201710996983 A CN 201710996983A CN 107843663 A CN107843663 A CN 107843663A
- Authority
- CN
- China
- Prior art keywords
- hcoo
- sugar
- adducts
- retention time
- molecular formula
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
- Granted
Links
Classifications
-
- G—PHYSICS
- G01—MEASURING; TESTING
- G01N—INVESTIGATING OR ANALYSING MATERIALS BY DETERMINING THEIR CHEMICAL OR PHYSICAL PROPERTIES
- G01N30/00—Investigating or analysing materials by separation into components using adsorption, absorption or similar phenomena or using ion-exchange, e.g. chromatography or field flow fractionation
- G01N30/02—Column chromatography
-
- G—PHYSICS
- G01—MEASURING; TESTING
- G01N—INVESTIGATING OR ANALYSING MATERIALS BY DETERMINING THEIR CHEMICAL OR PHYSICAL PROPERTIES
- G01N30/00—Investigating or analysing materials by separation into components using adsorption, absorption or similar phenomena or using ion-exchange, e.g. chromatography or field flow fractionation
- G01N30/02—Column chromatography
- G01N30/04—Preparation or injection of sample to be analysed
- G01N30/06—Preparation
Landscapes
- Physics & Mathematics (AREA)
- Health & Medical Sciences (AREA)
- Life Sciences & Earth Sciences (AREA)
- Chemical & Material Sciences (AREA)
- Analytical Chemistry (AREA)
- Biochemistry (AREA)
- General Health & Medical Sciences (AREA)
- General Physics & Mathematics (AREA)
- Immunology (AREA)
- Pathology (AREA)
- Other Investigation Or Analysis Of Materials By Electrical Means (AREA)
- Saccharide Compounds (AREA)
Abstract
The invention provides a kind of discrimination method of the Morinda officinalis oligosaccharide composition based on UPLC QTof/MS.Including：Prepare sample solution and reference substance solution；Detected using UPLC QTof/MS, according to testing result, determine Morinda officinalis oligosaccharide composition.Present invention optimizes the chromatogram of Morinda officinalis medicinal material oligosaccharide and mass spectrum separation and testing conditions, utilize Acquity UPLC BEH Amide C18 posts, pass through UPLC QTof/MS detecting systems, it is successfully separated and identifies 19 oligosaccharide compositions in Morinda officinalis medicinal material, scientific basis is provided for Morinda officinalis original new drug developmental research.
Description
Technical field
The invention belongs to chemical composition of Chinese materia medica analysis technical field, and in particular to a kind of Morinda offcinalis How based on UPLC-QTof/MS
The discrimination method of its oligosaccharide composition.
Background technology
Morinda officinalis How is madder wort Morinda officinalis Morinda officinalis How dry root, and main product is in wide
The ground such as east, Fujian, Guangxi, Hainan, it is the good medicine of traditional kidney-replenishing, is one of four great Nan medicines, there is kidney-replenishing, strengthening the bones and muscles, dispel
Rheumatism effect.Morinda officinalis mainly contains the compositions such as carbohydrate, lipid, anthraquinone, organic acid.At present, mirror is separated from Morinda officinalis medicinal material
Fixed carbohydrate content has fructose, sucrose, Bajisin, ketose, this resistance to sugar, IF- fruit furyl glycosyls resistance to this sugar, inulobiose
To seven sugar.Oligosaccharide is but notable to drug effect in Morinda officinalis at present because its extensive bioactivity is one of current study hotspot
The research and development of oligosaccharide sugar product relatively lag behind, after extracting and developing and purifying or derivatization are mainly taken in the identification of oligosaccharide, then
Differentiated using the methods of nuclear magnetic resoance spectrum, mass spectrum, time-consuming for experiment, expensive；And it there are no to Morinda officinalis oligosaccharide composition
The research report characterized comprehensively.
The content of the invention
It is an object of the invention to provide a kind of discrimination method of the Morinda officinalis oligosaccharide composition based on UPLC-QTof/MS.
The discrimination method of Morinda officinalis oligosaccharide composition provided by the present invention based on UPLC-QTof/MS, including following steps
Suddenly：
1) sample solution and reference substance solution are prepared：
By the root drying of Morinda officinalis, crush, sieving, with methanol aqueous solution ultrasonic extraction, centrifugation, collect supernatant, will be upper
Clear liquid filters, and obtains sample solution, standby；
Reference substance is dissolved with methanol aqueous solution, obtains reference substance solution, it is standby；
2) detected using UPLC-QTof/MS, according to testing result, determine Morinda officinalis oligosaccharide composition.
In above method step 1), 40 mesh sieves are concretely crossed in the sieving.
The methanol aqueous solution of the methanol aqueous solution concretely volumetric concentration 30%.
The ultrasonic extraction is carried out at room temperature.
The ultrasonic extraction can be carried out repeatedly, concretely 2 times.
The time of each ultrasonic extraction can be 30min.
The condition of the centrifugation can be that 12000g centrifuges 10min.
The filtering can be through 0.2 μm of filtering with microporous membrane.
The reference substance is：This resistance to sugar of 1F- fruit furyl glycosyls, D (+) glucose, sucrose, ketose and this resistance to sugar,
Purity is >=98%.
The experiment condition of detection is as follows in above method step 2)：
Chromatographic condition：
Chromatographic column：Acquity UPLC BEH Amide C18 (2.1x 100mm, 1.7 μm)；
Mobile phase A：80% acetonitrile solution (v/v, containing 0.1% ammoniacal liquor), Mobile phase B：30% acetonitrile solution (v/v, contains
0.1% ammoniacal liquor)；
Gradient：0~0.5min (0 → 0A, i.e. eluent are 100% Mobile phase Bs), 0.5~2.0min (0 →
10%A), 2.0~2.5min (10% → 13%A), 2.5~9.0min (18% → 34%A), 9.0~14min (34% →
50%A), 14~16min (50% → 60%A), 16~18min (60% → 60%A)；
35 DEG C of column temperature；
Flow velocity：200μL·min-1；
Sample size：1.0μL.
Mass Spectrometry Conditions：
Data acquisition scheme：Continuum patterns are used under the conditions of anion (ESI-), with sodium iodide correction mass scope
50-2500Da；
Capillary voltage：2.0KV；
Taper hole voltage 40V, 110 DEG C of source temperature, 450 DEG C of desolventizing temperature；
Desolvention gas velocity 900L/h；
Low energy passage collision energy is 6eV, and high-energy scanning collision energy is 30~50eV.
The Information in Mass Spectra of Morinda officinalis oligosaccharide composition is as follows：
The Information in Mass Spectra of the Morinda officinalis oligosaccharide composition of table 1
Note：* it is Morinda officinalis oligosaccharide [M -2H]2─
The present invention uses UPLC-QTOF/MS methods, and rapidly Morinda officinalis oligosaccharide composition is characterized comprehensively, passed through
Spectrum elucidation, it is determined that the structure of 19 kinds of Morinda officinalis oligosaccharide, section is provided for the innovative utilization research of Morinda officinalis medicinal material
Learn foundation.
Brief description of the drawings
Fig. 1 is UPLC-Q-Tof MS total ion currents (TIC) chromatogram of Radix Morindae Officinalis extract.
Fig. 2 is to utilize inulin-type oligosaccharide 3D ion stream chromatograms in the Morinda officinalis of UNIFY software processings.
Fig. 3 is Morinda officinalis inulin-type oligosaccharide structures skeleton symbol.
Fig. 4 be Morinda officinalis sample in sucrose, ketose and Nai Si sugar mass spectrogram and its with corresponding reference substance mass spectrogram.
Fig. 5 is this resistance to sugared mass spectrogram of 1F- fruit furyl glycosyls, and wherein A is high-energy mass spectrogram, and B is low energy mass spectrogram.
Fig. 6 is the mass spectrogram at peak 8, and wherein A is high-energy mass spectrogram, and B is low energy mass spectrogram.
Fig. 7 is the mass spectrogram at peak 15, and wherein A is low energy mass spectrogram, and B is high-energy mass spectrogram, and C is the height of part amplification
Energy mass spectrogram.
Embodiment
Below by specific embodiment, the present invention will be described, but the invention is not limited in this.
Experimental method used in following embodiments is conventional method unless otherwise specified；Institute in following embodiments
Reagent, material etc., unless otherwise specified, commercially obtain.
Embodiment
1. material
1.1 sample
Morinda officinalis sample (fleshy root of Morinda officinalis) is collected in Guangdong Yunan, through Chinese department of traditional Chinese medicine institute Hao Jin great researcher
Rubiaceae section plant Morindaofficinalis How are accredited as, former plant specimen is now stored in Chinese department of traditional Chinese medicine institute Chinese medicine
Resource center.
1.2 instrument
Acquity UPLC-I-Class series connection Xevo-G2-S Q-TOF GC-MSs, equipped with the matter of Masslynx 4.1
Spectrum work station (Waters companies, the U.S.), assay balance (plum Teller-support benefit, Switzerland), centrifuge (Eppendorf companies,
Germany), KQ-100DE ultrasonic cleaning machines (Kunshan Ultrasonic Instruments Co., Ltd.), 0.2 μm of syringe filter (Pall companies,
The U.S.).
1.3 reagent
Chromatographic grade acetonitrile, methanol (Merck companies, Germany)；Ammoniacal liquor (chromatographic grade, German Merck companies)；Ultra-pure water is
Milli-Q pure water systems are prepared in (resistance >=18.2M Ω, Millipore companies, the U.S.)
1.4 reference substance
1F- fruit furyl glycosyls are resistance to this sugared (lot number 11965-201501, purchased from National Institute for Food and Drugs Control)；D(+)
Glucose (lot number W-F012-150730), sucrose (lot number Z-F038-160715), ketose (lot number Z-F005-
151203), resistance to this sugared (N-F016-150617), Beijing Rong Cheng Xin De Science and Technology Ltd.s provide, and above reference substance purity >=
98%.
2. method
It is prepared by 2.1 sample solutions and reference substance solution
Sample crosses 40 mesh sieves, precision weighs 0.1g, adds the methanol aqueous solutions of 2.0mL 30% (V/V), room through drying, crushing
Warm ultrasonic extraction 2 times, each 30min, 12000g centrifugation 10min, takes supernatant through 0.2 μm of filtering with microporous membrane, standby.Respectively
Precision weighs appropriate reference substance, adds methanol (30% methanol aqueous solution (V/V)) ultrasonic dissolution, 4 DEG C are kept in dark place, standby.
2.2 experiment condition
2.2.1 chromatographic condition
Chromatographic column is Acquity UPLC BEH Amide C18 (2.1x 100mm, 1.7 μm)；Mobile phase A：80% acetonitrile
The aqueous solution (v/v, 0.1% ammoniacal liquor), Mobile phase B：30% acetonitrile solution (v/v, 0.1% ammoniacal liquor)；Gradient：0~
0.5min (0 → 0A), 0.5~2.0min (0 → 10%A), 2.0~2.5min (10% → 13%A), 2.5~9.0min (18%
→ 34%A), 9.0~14min (34% → 50%A), 14~16min (50% → 60%A), 16~18min (60% → 60%
A), 35 DEG C of column temperature, flow velocity：200 μ Lmin-1, sample size：1.0μL.
2.2.2 Mass Spectrometry Conditions
Data acquisition scheme：Continuum patterns are used under the conditions of anion (ESI-), with sodium iodide correction mass scope
50-2500Da；Capillary voltage：2.0KV；Taper hole voltage 40V, 110 DEG C of source temperature, 450 DEG C of desolventizing temperature；Desolventizing
Gas velocity 900L/h；Low energy passage collision energy is 6eV, and high-energy scanning collision energy is 30~50eV.
2.3 data processing
The compound library of Morinda officinalis oligosaccharide is established, is imported in the softwares of UNIFY 1.7, carries out peak extraction and Auto-matching
Oligosaccharide is identified, and is compared with the chromatogram of reference substance and Information in Mass Spectra, confirmation matches the structure and its phase of compound
Shred characterization is answered, meanwhile, Morinda officinalis oligosaccharide related data according to the literature, Morinda officinalis oligosaccharide composition is identified, is gone forward side by side
Row structural confirmation.
3. result and analysis
3.1 experimental condition optimization
For comprehensively characterize Morinda officinalis medicinal material oligosaccharide composition, by compare using pure water, various concentrations methanol and ethanol as
During Extraction solvent, the chromatographic isolation degree and the Information in Mass Spectra under high and low energy of extract, chromatographic condition, Mass Spectrometry Conditions are entered
Optimization is gone, it is determined that the testing conditions of Morinda officinalis oligosaccharide, see 2.1,2.2.The UPLC-Q-Tof MSE of Radix Morindae Officinalis extract
Total ion current (TIC) chromatogram is shown in Fig. 1, utilizes inulin-type oligosaccharide 3D ion flow chromatographies in the Morinda officinalis of UNIFY software processings
Figure is shown in Fig. 2, by Fig. 2 can be visually seen [M-H]-, [2M-H]-, [M-2H]2-Ionic strength Deng fragments characteristic characterizes situation,
And it will become apparent from [2M-H] of low quality oligosaccharide-[M-2H] at peak, high quality oligosaccharide2-The ionic strength at peak is higher.
3.2 compound identification
Establish UNIFY analysis methods:Establish the oligomeric glycodatabase of Morinda officinalis, and the Chinese medicine carried with the softwares of UNIFI 1.7
Chemical composition data storehouse merges, the intensity threshold of setting 3D blob detection parameters and the species at adduct ion peak, under negative ion mode
Adduct ion be [M-H]-, [M+HCOO]-, [M-2H] 2-.UNIFY analysis softwares identify the trust data after processing automatically,
And the different adduction forms of same compound are identified, provide molecular formula, mass number error, the isotope matching of authenticating compound
The information such as deviation, retention time, peak intensity and adduct ion；It is meanwhile corresponding according to the patch information under high-energy, Auto-matching
The possible cracking mode of compound structure.Due to software can not effective district enantiomers class compound, and individual molecules sometimes
Quasi-molecular ions judgement also likely to be present error, and matching the result of identification needs to carry out manual confirmation.
More than 200 individual compounds of Auto-matching after being handled using UNIFI analysis softwares, with reference to the chromatogram matter of reference substance
Spectrum information, and document report, the oligosaccharide in Morinda officinalis medicinal material is inulin-type oligosaccharide, and inulin-type oligosaccharide one end is sugarcane
Sugar, the linear straight chain type oligosaccharide formed by β (1 → 2) glycosidic bond links, it is β-furan type levulan that sugar chain, which increases group, end
End often carries a glucose residue, and with the increase of the degree of polymerization, the group and connected mode of growth are constant, and the degree of polymerization (DP) is logical
Often between 2~60, the normal title fructose oligosaccharides of the degree of polymerization relatively low (DP=2~9).The study find that Morinda officinalis oligosaccharide
Distribution has certain regularity, i.e., six carbon that a mass number is 162Da (C6H10O5) are differed between two neighboring oligosaccharide
Sugar.Morinda officinalis inulin-type oligosaccharide structures skeleton symbol is shown in Fig. 3, and this experiment detects 19 Morinda officinalis inulin-type oligosaccharide.Morinda officinalis
Sucrose in sample, the mass spectrogram of ketose and Nai Si sugar and its see Fig. 4 with corresponding reference substance mass spectrogram, Morinda officinalis inulin-type is low
Glycan qualification result is shown in Table 1.
The identification of the Morinda officinalis oligosaccharides of 3.3DP=3~13
By taking peak 4 as an example, illustrate the MS fragment pathways of inulin-type oligosaccharide：Occur in low energy mass spectrogram quasi-molecule from
Sub- peak [M-H]-(m/z 827.2668), adduct ion peak [M+HCOO]-(m/z873.2733), and [2M-H]-(m/z
1655.5356)；In high-energy mass spectrogram, m/z647.2035 is to lose 1 molecule H2O and 1 molecule from [M-H]-slough
Fragment ion caused by C6H10O5；M/z 485.1503 is that [M-H]-slough loses 1 molecule H2O and 2 molecule C6H10O5 institutes
Caused fragment ion, m/z 323.0969 be [M-H]-lose fragment caused by 1 molecule H2O and 3 molecule C6H10O5 from
Son；M/z179.0543 is [M-H]-lose fragment ion caused by 4 molecule C6H10O5, by with reference substance 1F- fruit furans
The comparison of resistance to this fried sugar spectrum Information in Mass Spectra of glycosyl, determine that Fig. 5 is shown in peak 4 for this resistance to sugar of 1F- fruit furyl glycosyls, its mass spectrogram.
There is quasi-molecular ion peak [M-H]-(m/z 1475.4810), adduct ion peak [M in low energy mass spectrogram in peak 8
+ HCOO]-(m/z 1521.4850) and [M-2H] 2- (m/z 737.2354), [M+HCOO-2H] 2- (m/z760.2384)；
At a high energy, m/z1295.4162 be from [M-H]-slough lose fragment caused by 1 molecule H2O and 1 molecule C6H10O5 from
Son；M/z 1151.3727 is that [M-H]-slough loses fragment ion caused by 2 molecule C6H10O5, and m/z 971.3068 is
[M-H]-lose fragment ion caused by 1 molecule H2O and 3 molecule C6H10O5；M/z809.2545 is [M-H]-lose 1 molecule
Fragment ion caused by H2O and 4 molecule C6H10O5；M/z737.2354 is [M-H]-lose fragment caused by 2 molecule H2O
Ion；M/z 647.2023 and 485.1493 is [M-H] respectively, and-losing 1 molecule H2O, 5 molecule C6H10O5 and [M-H]-loses 1
Fragment ion caused by molecule H2O and 6 molecule C6H10O5, m/z 3411073 and 179 are [M-H]-slough 7 molecules
Fragment ion caused by C6H10O5 and 8 molecule C6H10O5.According to documentation ＆ info, thus it is speculated that peak 8 is the glycan of inulin-type 9, its matter
Spectrogram is shown in Fig. 6.
Similarly, occur the fragment ion peak and [M-2H] 2- that add 162Da in the low energy mass spectrogram at peak 9~14 successively
Peak, and corresponding adduct ion peak [M+Cl]-, [M+HCOO]-, have in high energy mass spectrogram [M-H-C6H10O5-H2O]-peak,
The fragment ion peak and [M-2H] 2- of depigmentation 18Da, 162Da, 180Da or its integral multiple successively such as [M-H-2C6H10O5]-peak are broken
Piece quasi-molecular ions, therefore, according to Information in Mass Spectra, and combine document report [1,10-13] i, thus it is speculated that it is low that peak 9~14 is followed successively by inulin-type
Oligomeric 15 sugar of poly- 10 sugar~inulin-type, qualification result are shown in Table 1.
3.3DP=14 the identification of~19 Morinda officinalis oligosaccharides
Mass detector quality axle is corrected to 2500Da with sodium iodide, so failing accurately to detect that mass number is more than
2500Da molecular ion peak.But [M-2H] 2-, [M-3H] 3-, [M-2H can be accurately detected in low energy mass spectrogram
+ Cl] 2- fragment peaks, occur in high energy mass spectrogram [M-H]-successively fragment of depigmentation 18Da, 162Da, 180Da or its integral multiple from
Sub- peak.
By taking peak 15 as an example, illustrate the cleavage of mass spectrum situation of the inulin-type the oligosaccharide, [M- occurred in low energy mass spectrogram
2H]-(m/z1304.4230), [M-H+HCOO] 2- (m/z1327.9240) fragment peak；In high-energy mass spectrogram, there is m/
z179.0551、341.1078、503.1615、665.2161、827.2669、989.3194、1475.6339、1637.5265、
1961.8220th, a series of [M-H]-depigmentation 162Da or 180Da such as 2123.8633,2285.9060 fragment ion, passes through
UNIFI is analyzed and is combined traditional Chinese medicine ingredients database, and combines document report, thus it is speculated that peak 15 is the sugar of inulin-type 16, and its mass spectrogram is shown in
Fig. 7.It is respectively the sugar of inulin-type 17,18,19 similarly to speculate peak 16,17,18.
4 discuss
Carbohydrate is widely distributed in nature, the difference of the connected mode of monose, the order of connection and absolute configuration, creates
The information of saccharide compound is very abundant.Because oligosaccharide has unique structure and extensive bioactivity, because it can significantly be carried
The growth of high intestinal microbiota and function；Again because being not easy to be digested absorption, it is widely used in food industry, for substituting
Fat or as sweetener low in calories.Oligosaccharide composition is Morinda officinalis medicinal material main component, accounts for more than the 30% of medicinal material dry weight.
Research report Morinda officinalis oligosaccharide has antidepression, promotes immune, resisting stress, protection Cardiovascular.This research optimizes bar
Chromatogram and the mass spectrum separation of halberd day medicinal material oligosaccharide and testing conditions, using Acquity UPLC BEH Amide C18 posts, lead to
UPLC-QTof/MS detecting systems are crossed, is successfully separated and identifies 19 oligosaccharide compositions in Morinda officinalis medicinal material, are created for Morinda officinalis
Novel drugs developmental research provides scientific basis.
Claims (4)
1. a kind of discrimination method of Morinda officinalis oligosaccharide composition, comprises the steps：
1) sample solution and reference substance solution are prepared：
By the root drying of Morinda officinalis, crush, sieving, with methanol aqueous solution ultrasonic extraction, centrifugation, supernatant is collected, by supernatant
Filtering, obtains sample solution, standby；
Reference substance is dissolved with methanol aqueous solution, obtains reference substance solution, it is standby；
2) detected using UPLC-QTof/MSE, according to testing result, determine Morinda officinalis oligosaccharide composition.
2. discrimination method according to claim 1, it is characterised in that：
In step 1), the methanol aqueous solution is the methanol aqueous solution of volumetric concentration 30%；
The ultrasonic extraction is carried out at room temperature；The ultrasonic extraction carries out multiple；The time of each ultrasonic extraction is 30min；
The reference substance is：This resistance to sugar of 1F- fruit furyl glycosyls, D (+) glucose, sucrose, ketose and this resistance to sugar, purity
>=98%.
3. discrimination method according to claim 1 or 2, it is characterised in that：The experiment condition of detection is as follows in step 2)：
Chromatographic condition：
Chromatographic column：Acquity UPLC BEH Amide C18 (2.1x100mm, 1.7 μm)；
Mobile phase A：80% acetonitrile solution, v/v contain 0.1% ammoniacal liquor, Mobile phase B：30% acetonitrile solution, v/v, containing 0.1%
Ammoniacal liquor；
Gradient：0~0.5min (0 → 0A), 0.5~2.0min (0 → 10%A), 2.0~2.5min (10% → 13%A),
2.5~9.0min (18% → 34%A), 9.0~14min (34% → 50%A), 14~16min (50% → 60%A), 16~
18min (60% → 60%A)；
35 DEG C of column temperature；
Flow velocity：200μL·min-1；
Sample size：1.0μL；
Mass Spectrometry Conditions：
Data acquisition scheme：Continuum patterns are used under the conditions of anion (ESI-), with sodium iodide correction mass scope 50-
2500Da；
Capillary voltage：2.0KV；
Taper hole voltage 40V, 110 DEG C of source temperature, 450 DEG C of desolventizing temperature；
Desolvention gas velocity 900L/h；
Low energy passage collision energy is 6eV, and high-energy scanning collision energy is 30~50eV.
4. according to the discrimination method any one of claim 1-3, it is characterised in that：
Retention time 9.98min；m/z 341.1078；Neutral mass(Da)342.1162；Adducts-H,+HCOO；It is high
Energy fragment (-) (m/z) 323.0965,267.0703,249.0596,179.0542,143.0332,113.0228,
Material corresponding to 101.0229,89.0229,71.0126 is sucrose, and its molecular formula is C12H22O11；
Retention time 11.39min；m/z 503.1614；Neutral mass(Da)504.1690；Adducts-H,+HCOO；It is high
Energy fragment (-) (m/z) 485.1421,341.1068,325.0255,179.0208,143.0332,113.0228,
Material corresponding to 101.0229,89.0229,71.0126 is ketose, and its molecular formula is C18H32O16；
Retention time 12.23；m/z 665.2175；Neutral mass(Da)666.2218；Adducts+HCOO,-H,-H+
HCOO；High-energy fragment (-) (m/z) 711.2206,485.1415,323.0914,247.0199,179.0575,101.0320,
Material corresponding to 71.0250 is this resistance to sugar, and its molecular formula is C24H42O21；
Retention time 12.90；m/z 827.2668；Neutral mass(Da)828.2747；Adducts-H,+HCOO,-H+
HCOO；High-energy fragment (-) (m/z) 873.2729,647.2053,485.1439,341.1040,323.0952,179.0577,
Material corresponding to 113.0305,101.0328 is this resistance to sugar of 1F- fruit furyl glycosyls, and its molecular formula is C30H52O26；
Retention time 13.45；m/z 989.3193；Neutral mass(Da)990.3275；Adducts-H,+HCOO,-H+
HCOO；High-energy fragment (-) (m/z) 809.2558,647.2033,485.1503,341.1075,323.0970,179.0544
Corresponding material is the sugar of inulin-type six, and its molecular formula is C36H62O31；
Retention time 13.98；m/z 1151.3723；Neutral mass(Da)1152.3803；Adducts-H,+HCOO,-
2H；High-energy fragment (-) (m/z) 989.3854,971.3716,809.2932,647.2025,485.1496,341.1069,
Material corresponding to 179.0541 is the sugar of inulin-type seven, and its molecular formula is C42H72O36；
Retention time 14.44；m/z 1313.4275；Neutral mass(Da)1314.4332；Adducts-H,+HCOO,-
2H；High-energy fragment (-) (m/z) 1133.3635,989.3191,809.2565,647.2028,485.1499,341.1075,
Material corresponding to 179.0545 is the sugar of inulin-type eight, and its molecular formula is C48H82O41；
Retention time 14.88；m/z 1475.4813；Neutral mass(Da)1476.4860；Adducts-H,+HCOO,-
2H；High-energy fragment (-) (m/z) 1295.4185,1151.3735,1133.3632,971.3093,809.2560,
Material corresponding to 737.2364,485.1511,341.1079,179.0545 is the sugar of inulin-type nine, and its molecular formula is C54H92O46；
Retention time 15.30；m/z 1637.5283；Neutral mass(Da)1638.5388；Adducts-H,+HCOO,-
2H；High-energy fragment (-) (m/z) 1457.4706,1313.4291,971.3083,818.2624,647.2032,485.1504,
Material corresponding to 341.1079,179.0544 is the sugar of inulin-type ten, and its molecular formula is C60H102O51；
Retention time 15.68；m/z 1799.5788；Neutral mass(Da)1800.5916；Adducts-H,+HCOO,-
2H,-H+2HCOO；High-energy fragment (-) (m/z) 1619.5164,1475.4785,1313.4261,1133.3590,
971.3075,899.2877,809.2554,737.2352,665.2127,503.1605,34 corresponding to 1.1074,179.0544
Material is the sugar of inulin-type 11, and its molecular formula is C66H112O56；
Retention time 16.02；m/z 1961.6332；Neutral mass(Da)1962.6444；Adducts-H,+HCOO,-
2H；High-energy fragment (-) (m/z) 1781.5574,1619.5194,1456.4677,1295.4120,1133.3604,
Material corresponding to 980.3140,773.2411,665.2130,503.1604,341.1075,179.0543 is the sugar of inulin-type 12,
Its molecular formula is C72H122O61；
Retention time 16.32；m/z 2123.6819；Neutral mass(Da)2124.6973；Adducts-H,+HCOO,-
2H,-H+HCOO；High-energy fragment (-) (m/z) 179.0541,341.1071,503.1601,665.2131,827.2652,
(100), 971.3075,1061.3392 material corresponding to 1295.4146,1619.5110,1781.7668,1943.8130 is chrysanthemum
The sugar of powder type 13, its molecular formula is C78H132O66；
Retention time 16.60；m/z 2275.6821；Neutral mass(Da)2286.7501；Adducts-2H,-H+HCOO；
High-energy fragment (-) (m/z) 179.0541,341.1073,503.1600,665.2132,827.2657,971.3059,
1052.3329,1142.3672,1313.4301,475.4690,1619.5095,1799.5665,1943.5879,
Material corresponding to 1961.5886 is the sugar of inulin-type 14, and its molecular formula is C84H142O71；
Retention time 16.86；m/z 2447.7971；Neutral mass(Da)2448.8029；Adducts-2H,-H+HCOO；
High-energy fragment (-) (m/z) 179.0541,341.1073,503.1612,665.2269,827.3028,989.3933,
1061.4259,1133.4506,1223.3937,1475.6639,1637.6936,1799.7751,1961.8220,
Material corresponding to 2123.8821,2297.8867,2448.9170 is the sugar of inulin-type 15, and its molecular formula is C90H152O76；
Retention time 17.09；m/z 1304.4230；Neutral mass(Da)1304.4200；Adducts-2H,-H+HCOO；
High-energy fragment (-) (m/z) 179.0551,341.1078,503.1615,665.2161,827.2669,869.2774,
989.3194,1133.4506,1304.9229,1327.9279,1475.6339,1637.7102,1799.7751,
Material corresponding to 1961.8220,2285.9060,2447.8833 is the sugar of inulin-type 16, and its molecular formula is C96H162O81；
Retention time 17.31；m/z 1385.5767；Neutral mass(Da)1385.4465；Adducts-2H,-H+HCOO；
High-energy fragment (-) (m/z) 179.0221,341.0862,503.1585,665.2269,827.3028,923.2950,
Material corresponding to 989.3933,1214.3844 is the sugar of inulin-type 17, and its molecular formula is C102H172O86；
Retention time 17.52；m/z 1466.6167；Neutral mass(Da)1466.4729；Adducts-2H,-H+HCOO；
High-energy fragment (-) (m/z) 179.0221,341.0862,503.1585,665.2269,827.3146,989.3804,
Material corresponding to 1151.4613,1377.0674,1467.1187 is the sugar of inulin-type 18, and its molecular formula is C108H182O91；
Retention time 17.73；m/z 1547.4991；Neutral mass(Da)1547.4993；Adducts-2H,-H+HCOO；
High-energy fragment (-) (m/z) 179.0221,341.0862,503.1585,665.2374,827.2656,989.3248,
Material corresponding to 1031.7328,1151.3612,1548.1543 is the sugar of inulin-type 19, and its molecular formula is C114H192O96；
Retention time 17.95；m/z 1628.7058；Neutral mass(Da)1628.5257；Adducts-2H,-H+HCOO；
High-energy fragment (-) (m/z) 179.0221,341.0862,503.1585,665.2269,827.3146,989.3804,
Material corresponding to 1085.4323,1151.4613,1466.9878,1548.4833,1628.5212 is that inulin-type 20 is sugared, its point
Minor is C120H202O101。
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CN201710996983.2A CN107843663B (en) | 2017-10-20 | 2017-10-20 | Identification method of morinda officinalis oligosaccharide component |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CN201710996983.2A CN107843663B (en) | 2017-10-20 | 2017-10-20 | Identification method of morinda officinalis oligosaccharide component |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| CN107843663A true CN107843663A (en) | 2018-03-27 |
| CN107843663B CN107843663B (en) | 2020-08-11 |
Family
ID=61662685
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CN201710996983.2A Active CN107843663B (en) | 2017-10-20 | 2017-10-20 | Identification method of morinda officinalis oligosaccharide component |
Country Status (1)
| Country | Link |
|---|---|
| CN (1) | CN107843663B (en) |
Cited By (6)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN109374779A (en) * | 2018-12-17 | 2019-02-22 | 杭州奕安济世生物药业有限公司 | A kind of rapid detection method of cane sugar content |
| CN109521109A (en) * | 2018-11-13 | 2019-03-26 | 中国中医科学院中药研究所 | A kind of fast quantitative measurement method for detecting of inulin-type oligosaccharide in Chinese medicine |
| CN110568111A (en) * | 2019-09-30 | 2019-12-13 | 广东一方制药有限公司 | Method for detecting oligosaccharide in morinda officinalis formula particles |
| CN112903839A (en) * | 2021-01-15 | 2021-06-04 | 中国检验检疫科学研究院 | Method for qualitatively detecting alpha and beta configurational isomers of monosaccharide and method for detecting proportion of monosaccharide isomers |
| CN112903842A (en) * | 2021-01-18 | 2021-06-04 | 中国检验检疫科学研究院 | Method for detecting monosaccharide |
| CN113768942A (en) * | 2021-08-20 | 2021-12-10 | 广州中医药大学(广州中医药研究院) | Morinda officinalis processed product oligosaccharide composition and preparation method and application thereof |
Citations (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN103372208A (en) * | 2012-04-19 | 2013-10-30 | 厦门大学 | Application of morindae radix extract in preparation of immunologic adjuvant |
| CN105675734A (en) * | 2014-11-19 | 2016-06-15 | 天津天士力现代中药资源有限公司 | Method for detecting oligosaccharide component content in compound salvia miltiorrhiza bge extract |
| CN107056851A (en) * | 2017-06-05 | 2017-08-18 | 广东省微生物研究所（广东省微生物分析检测中心） | A kind of preparation method of the total oligosaccharide of Morinda officinalis |
-
2017
- 2017-10-20 CN CN201710996983.2A patent/CN107843663B/en active Active
Patent Citations (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN103372208A (en) * | 2012-04-19 | 2013-10-30 | 厦门大学 | Application of morindae radix extract in preparation of immunologic adjuvant |
| CN105675734A (en) * | 2014-11-19 | 2016-06-15 | 天津天士力现代中药资源有限公司 | Method for detecting oligosaccharide component content in compound salvia miltiorrhiza bge extract |
| CN107056851A (en) * | 2017-06-05 | 2017-08-18 | 广东省微生物研究所（广东省微生物分析检测中心） | A kind of preparation method of the total oligosaccharide of Morinda officinalis |
Non-Patent Citations (2)
| Title |
|---|
| 景海漪等: "巴戟天炮制前后寡糖类成分 HPLC-CAD 指纹图谱研究", 《中草药》 * |
| 王美玲等: "UPLC-Q-TOF MSE技术结合UNIFI数据库筛查方法快速分析巴戟天化学成分", 《质谱学报》 * |
Cited By (7)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN109521109A (en) * | 2018-11-13 | 2019-03-26 | 中国中医科学院中药研究所 | A kind of fast quantitative measurement method for detecting of inulin-type oligosaccharide in Chinese medicine |
| CN109374779A (en) * | 2018-12-17 | 2019-02-22 | 杭州奕安济世生物药业有限公司 | A kind of rapid detection method of cane sugar content |
| CN110568111A (en) * | 2019-09-30 | 2019-12-13 | 广东一方制药有限公司 | Method for detecting oligosaccharide in morinda officinalis formula particles |
| CN112903839A (en) * | 2021-01-15 | 2021-06-04 | 中国检验检疫科学研究院 | Method for qualitatively detecting alpha and beta configurational isomers of monosaccharide and method for detecting proportion of monosaccharide isomers |
| CN112903839B (en) * | 2021-01-15 | 2023-02-17 | 中国检验检疫科学研究院 | Method for qualitatively detecting alpha and beta configurational isomers of monosaccharide and method for detecting proportion of monosaccharide isomers |
| CN112903842A (en) * | 2021-01-18 | 2021-06-04 | 中国检验检疫科学研究院 | Method for detecting monosaccharide |
| CN113768942A (en) * | 2021-08-20 | 2021-12-10 | 广州中医药大学(广州中医药研究院) | Morinda officinalis processed product oligosaccharide composition and preparation method and application thereof |
Also Published As
| Publication number | Publication date |
|---|---|
| CN107843663B (en) | 2020-08-11 |
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| CN107843663A (en) | A kind of discrimination method of Morinda officinalis oligosaccharide composition | |
| Engelberth et al. | Comparing extraction methods to recover ginseng saponins from American ginseng (Panax quinquefolium), followed by purification using fast centrifugal partition chromatography with HPLC verification | |
| Fan et al. | A rapid, accurate and sensitive method for determination of monosaccharides in different varieties of Osmanthus fragrans Lour by pre-column derivatization with HPLC-MS/MS | |
| CN109239224B (en) | Method for simultaneously and quantitatively measuring 9 blood-entering components in spina date seed water extract | |
| Hu et al. | Determination and analysis of monosaccharides in Polygonatum cyrtonema Hua polysaccharides from different areas by ultra‐high‐performance liquid chromatography quadrupole trap tandem mass spectrometry | |
| Gao et al. | Simultaneous determination of oleanolic acid, ursolic acid, quercetin and apigenin in Swertia mussotii Franch by capillary zone electrophoresis with running buffer modifier | |
| Li et al. | Rapid screening and identification of the differences between metabolites of Cistanche deserticola and C. tubulosa water extract in rats by UPLC-Q-TOF-MS combined pattern recognition analysis | |
| Luo et al. | UPLC-Q-TOF/MS coupled with multivariate statistical analysis as a powerful technique for rapidly exploring potential chemical markers to differentiate between radix paeoniae alba and radix paeoniae rubra | |
| Xiang et al. | Simultaneous determination of polysaccharides and 21 nucleosides and amino acids in different tissues of Salvia miltiorrhiza from different areas by UV–visible spectrophotometry and UHPLC with triple quadrupole MS/MS | |
| Zeng et al. | Preparation and quantification of the total phenolic products in Citrus fruit using solid‐phase extraction coupled with high‐performance liquid chromatography with diode array and UV detection | |
| Shen et al. | Development of a HPLC‐MS/MS Method to Determine the 13 Elements of Semen Cuscutae and Application to a Pharmacokinetic Study in Rats | |
| Wang et al. | Enhanced ultrasound-assisted enzymatic hydrolysis extraction of quinolizidine alkaloids from Sophora alopecuroides L. seeds | |
| CN101322758A (en) | Method for producing spina date seed extract using complex enzyme | |
| Qi et al. | Characterization and discrimination of steroidal saponins in Tribulus terrestris L. and its three different aerial parts by chemical profiling with chemometrics analysis | |
| CN103575830B (en) | The analysis method of 4 kinds of anthraquinones and its application in pharmacokinetics in blood plasma | |
| CN107056851A (en) | A kind of preparation method of the total oligosaccharide of Morinda officinalis | |
| CN110563686A (en) | Actinidia arguta root extract, extraction and separation method and application thereof | |
| CN112730677B (en) | UPLC-Q-TOF/MS method for detecting multiple chemical components in paederia scandens | |
| Jin et al. | Optimization of green extraction process with natural deep eutectic solvent and comparative in vivo pharmacokinetics of bioactive compounds from Astragalus-Safflower pair | |
| Duan et al. | High‐throughput LC–MS method for the rapid characterisation and comparative analysis of multiple ingredients of four hawthorn leaf extracts | |
| CN104606288B (en) | The preparation method of Scullcap total-flavonoid aglycone extract | |
| CN100457768C (en) | Preparation method of breviscapine raw material medicine by using big-hole resin | |
| CN109100431A (en) | A kind of effective substance research method of palace of the Qing Dynasty Shoutao pills | |
| Wang et al. | Ultra high performance liquid chromatography with quadrupole time‐of‐flight tandem mass spectrometry and liquid chromatography with tandem mass spectrometry combined with chemometric analysis as an approach for the quality evaluation of Mume Fructus | |
| Dai et al. | Global detection and identification of components from Y unnan B aiyao based on liquid chromatography hybrid ion trap time‐of‐flight mass spectrometry |
Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| PB01 | Publication | ||
| PB01 | Publication | ||
| SE01 | Entry into force of request for substantive examination | ||
| SE01 | Entry into force of request for substantive examination | ||
| GR01 | Patent grant | ||
| GR01 | Patent grant |