CN114200059B - Method for rapidly screening toxic alkaloids in Chinese herbal medicine based on UPLC-QTOF-MS technology combined UNIFI - Google Patents

Method for rapidly screening toxic alkaloids in Chinese herbal medicine based on UPLC-QTOF-MS technology combined UNIFI Download PDF

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CN114200059B
CN114200059B CN202111528411.4A CN202111528411A CN114200059B CN 114200059 B CN114200059 B CN 114200059B CN 202111528411 A CN202111528411 A CN 202111528411A CN 114200059 B CN114200059 B CN 114200059B
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何聿
李慧晨
余艳槟
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Abstract

In view of the characteristics of complex structure, low content in biological samples, high toxicity, no specific clinical manifestation of poisoning and the like of toxic alkaloids, the invention develops a high-energy, high-flux and high-efficiency accurate screening method for the toxic alkaloids in the Chinese herbal medicines based on UPLC-QTOF-MS technology combined with UNIFI software. According to the invention, a Chinese herbal medicine sample is extracted by methanol, an organic filter membrane is adopted for filtering, UPLC-QTOF-MS detection is adopted, the sample to be screened is subjected to data acquisition by adopting an MSE detection mode, and the matching and screening of information such as mass-to-charge ratio, molecular ion peaks, fragment ions and the like are carried out on the original data by means of a natural product information base in UNIFI software. Compared with the traditional analysis and detection method, the method is simple to operate, quick in analysis and reliable in qualitative result, provides a good analysis and detection means for quick screening of toxic alkaloids in the Chinese herbal medicine, and has important significance in the field of clinical quality control application of the Chinese herbal medicine.

Description

Method for rapidly screening toxic alkaloids in Chinese herbal medicine based on UPLC-QTOF-MS technology combined UNIFI
Technical Field
The invention relates to the technical field of detection, in particular to a method for rapidly screening toxic alkaloids in Chinese herbal medicines based on UPLC-QTOF-MS technology combined UNIFI.
Background
The Chinese herbal medicine refers to substances which are used for preventing, treating and diagnosing diseases and have rehabilitation and health care effects under the guidance of the theory of traditional Chinese medicine, and is also an important mark of traditional Chinese medicine different from other medicines. The Chinese herbal medicine mainly comes from natural medicines and processed products thereof, including plant medicines, animal medicines, mineral medicines and partial chemical and biological products medicines. Because of the majority of Chinese herbal medicines, the theory that all medicines are herb-based is that the Chinese herbal medicines are herb-based. At present, most of Chinese herbal medicines are thought to be natural animal and plant and pure Chinese herbal medicine preparations, and are more mild and safer than chemical medicines in property, and no toxic or side effect of the medicines occurs. However, just like ancient clouds "three-component toxicity of drugs", if any misuse, decommissioning of the drug stones can also occur. The toxicity of the Chinese herbal medicine is a toxic reaction caused by toxic components contained in the medicine, and most of the toxic components are toxic alkaloids.
Alkaloids are a class of basic organic compounds containing nitrogen that exist in nature and have an alkali-like nature and have therefore in the past been referred to as pseudobases. Some of these alkaloids are toxic and are prone to poisoning. The part of alkaloid has complex structure, low content in biological samples, small poisoning dosage, large toxicity and no specific clinical manifestation of poisoning, which clearly increases the difficulty of screening and analyzing the toxic alkaloids, thus establishing a simple and rapid method for screening various toxic alkaloids has important significance for clinical Chinese herbal medicine application.
Comprehensive domestic and foreign literature reports indicate that the analysis and detection methods of the toxic alkaloids include liquid chromatography, liquid chromatography tandem mass spectrometry, gas chromatography tandem mass spectrometry, thin layer chromatography, molecular imprinting technology, high-efficiency capillary electrophoresis and the like. Most methods are complex in steps, time consuming, limited in detection of objects, and low in accuracy.
In summary, the inventor considers developing a high-energy, high-throughput and high-efficiency accurate screening method for toxic alkaloids in common Chinese herbal medicines based on UPLC-QTOF-MS technology combined UNIFI, so that the detection efficiency and accuracy of the toxic alkaloids in the Chinese herbal medicines are greatly improved.
Disclosure of Invention
The technical problem solved by the invention is to provide a method for rapidly screening toxic alkaloids in Chinese herbal medicines based on UPLC-QTOF-MS technology combined with UNIFI, which has the advantages of rapidness, sensitivity and accuracy.
In order to achieve the above purpose, the invention adopts the following technical scheme:
The invention provides a method for rapidly screening toxic alkaloids in Chinese herbal medicines based on UPLC-QTOF-MS technology in combination with UNIFI, which comprises the following steps:
Step a), grinding the dried Chinese herbal medicines into powder, and sieving; mixing the Chinese herbal medicine powder with a solvent, performing ultrasonic extraction at room temperature, centrifuging, filtering the supernatant by an organic filter membrane to obtain a sample, and storing the sample in a sample bottle for sample injection;
And b) separating and detecting the sample prepared in the step a) by using an ultra-high performance liquid chromatography tandem mass spectrometer to obtain an alkaloid component substance peak, and carrying out qualitative analysis on the substance peak by using UNIFI software.
Further, in step a), the mesh number of the screen is 60 mesh.
Further, in the step a), the solvent is methanol, and the ratio of the Chinese herbal medicine powder to the solvent is 1:100 m/v.
Further, in the step a), the ultrasonic extraction time is 30 min, the ultrasonic power is 200W, and the ultrasonic frequency is 40 kHz.
Further, in step a), the centrifugation time is 10 min and the centrifugation speed is 10000 rpm.
Further, in the step a), the supernatant is filtered by an organic filter membrane with the aperture of 0.45 mu m, and then filtered by an organic filter membrane with the aperture of 0.22 mu m.
Further, in the step b), the conditions of the liquid chromatography separation are: the column was ACQUITY UPLC-BEH C 18 (2.1 mm X100 mm,1.7 μm, waters, USA); sample injection amount is 1 mu L, flow rate is 0.2 mL/min, and column temperature is 40 ℃; the mobile phase of the elution system is: mobile phase A is water (10 mmol/L ammonium formate) and mobile phase B is methanol; gradient elution is performed by ：0-1 min,95% A;1-3 min,95% A→ 70% A;3-12 min,75% A→55% A;12-20 min,55% A→ 1% A;20-25 min,1% A;25-25.1 min,1%A-95% A;25.1-30min,95% A.
Further, in step b), the conditions for mass spectrometry detection are: electrospray ion source (ESI), MSE positive ion scan mode; nitrogen is the reverse blowing, desolventizing and atomizing gas of the taper hole, and argon is the collision gas; the capillary voltage is 2.00 kV, the cone hole voltage is 40V, the ion source temperature is 150 ℃, the desolvation air flow rate is 600L/h, the solvent air temperature is 350 ℃, the cone hole back-blowing air flow rate is 50L/h, the low energy collision voltage is 6V, the high energy collision voltage is 30-50V, the mass scanning range is 50-1200 Da, the scanning time is 0.250 s, and the scanning time interval is 0.250 s.
Further, in step b), the model number of the UNIFI software is Waters UNIFI 1.8.
The invention has the remarkable advantages that:
Compared with the existing detection method, the method provided by the invention can accurately measure the relative molecular mass of the compound, and can accurately determine the quality of the compound, so that false detection and omission of samples are avoided, the sample processing is simple, the screening variety is multiple, the qualitative result is accurate and reliable, the screening capability of the samples can be greatly improved, and the method has important significance in clinical quality control application of the Chinese herbal medicines.
Drawings
FIG. 1 is a secondary mass spectrum of aristolochic acid I.
FIG. 2 is a secondary mass spectrum of aconitine.
FIG. 3 is a second-order mass spectrum of the K.k.
FIG. 4 is a secondary mass spectrum of solanine.
Detailed Description
In order to make the contents of the present invention more easily understood, the technical scheme of the present invention will be further described with reference to the specific embodiments, but the present invention is not limited thereto.
Example 1
The herbs used in this example are selected from Table 1, which are commercially available.
TABLE 1 information on Chinese herbal medicine
The instruments and reagents used in this example were as follows:
Instrument: waters Acquity UPLC H-Class ultra-high performance liquid chromatography and Xex G2 QTOF/MS mass spectrometry.
Reagent: acetonitrile (mass spectro-pure, merck company, germany), methanol (chromatographic pure, merck company, germany), formic acid (chromatographic pure, ACS company, usa), sodium hydroxide (analytical pure, sigma-Aldrich company, usa), leucine enkephalin (mass spectro-pure, waters company, usa), ammonium formate (chromatographic pure, mackin company).
1. Sample preparation
Cutting the purchased dried Chinese herbal medicines into small blocks, putting into a pulverizer for pulverizing, grinding into powder, sieving with a 60-mesh sieve, and putting the sieved powder into a PE self-sealing bag for standby. Weighing 0.3g of Chinese herbal medicine powder, placing the powder into a 50 mL centrifuge tube, adding 30mL of methanol into the centrifuge tube, performing ultrasonic extraction at room temperature for 30min, performing ultrasonic power of 200W and ultrasonic frequency of 40 kHz, centrifuging for 10 min under 10000 r/min, filtering the supernatant by an organic filter membrane with the aperture of 0.45 mu m, filtering by an organic filter membrane with the aperture of 0.22 mu m, storing the filtrate in a sample bottle, and storing the filtrate at 4 ℃ in a dark place to be tested.
2. Separation and detection of samples
And separating and detecting the prepared sample by using an ultra-high performance liquid chromatography tandem mass spectrometer, wherein the ultra-high performance liquid chromatography tandem mass spectrometer consists of Waters Acquity UPLC H-Class ultra-high performance liquid chromatography and a Xex G2 QTOF/MS mass spectrometer.
The liquid chromatography conditions were: ACQUITY UPLC-BEH C 18 column (2.1X100 mm,1.7 μm); sample injection amount is 1 mu L, flow rate is 0.2 mL/min, and column temperature is 40 ℃; the mobile phase of the elution system is: mobile phase A is water (10 mmol/L ammonium formate) and mobile phase B is methanol; gradient elution is performed by ：0-1 min,95%A;1-3 min,95%A→70% A;3-12 min,75% A→55% A;12-20 min,55% A→1% A;20-25 min,1% A;25-25.1 min,1% A→95% A;25.1-30 min,95% A.
The mass spectrum conditions are as follows: electrospray ion source (ESI), positive ion scanning mode (ESI+), nitrogen is counter-blowing, desolventizing and atomizing gas of taper hole, argon is collision gas, capillary voltage is 2.00 kV, taper hole voltage is 40V, ion source temperature is 150 ℃, desolventizing gas flow rate is 600L/h, solvent gas temperature is 350 ℃, taper hole nitrogen flow rate is 50L/h, low energy collision voltage is 6V, high energy collision voltage is 30-50V, mass scanning range is 50-1200 Da, scanning time is 0.250 s, and scanning time interval is 0.250 s.
3. Qualitative analysis of toxic alkaloid components in Chinese herbal medicine
And introducing the peak data of alkaloid component substances measured by the ultra-high performance liquid chromatography tandem mass spectrometer into Waters UNIFI 1.8.8 software for analysis.
Before data processing, the English names, molecular formulas, precise molecular weights and CAS numbers of the chemical components are input into an Excel table by consulting related documents of alkaloid chemical components in 43 Chinese herbal medicines reported at home and abroad (the information of the Chinese herbal medicines is shown in table 1), the structural formula of each chemical component is obtained from CHEMSPIDER through the CAS numbers, the Excel table and the structural formula are imported into UNIFI 1.8.8 software of Waters, and 92 compounds are collected from a toxic alkaloid database. Then, the extracted alkaloid component substances in 43 Chinese herbal medicines are qualitatively analyzed in Waters UNIFI 1.8.8 software, the cracking mode is analyzed through the secondary mass spectrum fragment information of toxic alkaloids, 47 alkaloid components including aristolochia alkaloids, aconite alkaloids, pyrrolizidine alkaloids and other types of alkaloids are separated and identified in 43 Chinese herbal medicines, and the specific table 2 shows that. The references referred to are as follows:
[1] Mi Shili, shi Haiwei, tan Li, etc. qualitative and quantitative analysis of aristolochic acid components in 9 kinds of Chinese medicinal materials containing aristolochic acid toxic substances [ J ]. Pharmaceutical journal, 2021, 56 (7): 8.
[2] Kong Dejiang, gao Huiyuan, li Xin, etc. based on UHPLC-Q/TOF-MS technology, the content of 8 aristolochic acids in five plants of Aristolochiaceae [ J ]. Chinese pharmaceutical (English edition), 2015, 024 (006): 364-375 was rapidly determined.
[3] Yuan, lin Ji the method for qualitative and quantitative detection of 14 aconite alkaloids and their metabolites in aconite plants by ultra performance liquid chromatography-time-of-flight mass spectrometry [ J ]. Food safety quality detection report, 2018, 9 (21): 6.
[4] Su Yu identification and comparison of radix Aconiti and radix Aconiti Kusnezoffii, and analysis of pharmacological Activity [ J ]. Modern medicine, confucius, 2020, 18 (7): 2.
[5]Wang J , Zhang M , Chen L , et al. Determination of Toxic Pyrrolizidine Alkaloids in Traditional Chinese Herbal Medicines by UPLC-MS/MS and Accompanying Risk Assessment for Human Health[J]. Molecules, 2021, 26(6):1648.
[6] Zhimin, LUO, Xuan, et al. Development of UPLC-Q-TOF-MS Coupled with Cation-exchange Solid-phase Extraction Method for the Determination of Ten Pyrrolizidine Alkaloids in Herbal Medicines[J]. Analytical Sciences, 2019, 35(12):1317-1325.
[7] Wang Lin, sun Lin, liu Huiying, et al, chemical composition of gelsemium elegans, chinese herbal medicine, 2017, 48 (10): 5.
[8] Pang Yongfeng, chen Peifeng the chemical composition of Solanum nigrum, and the research of pharmacological and toxicology, J. Mountain-western medicine, 2011, 27 (1): 3.
Wherein 6 kinds of aristolochia alkaloids are identified by co-separation, taking compound 1 as an example (figure 1), in a positive ion mode, the primary mass spectrum M/z of compound 1 is 359.0873, corresponding to [ M+NH 4]+ ], and fragment ions M/z observed by the secondary mass spectrum are 324.04990, 280.05892, 265.03713 and 236.04102 which are respectively generated by [M+H-H2O]+,[M+H-H2O-CO2]+,[M+H-H2O-CO2-CH2O]+、[M+H-H2O-CO2-CH2O-CO]+; based on the molecular weight, ion fragment information and the compound database, it is inferred that the compound is aristolochic acid I, and the rest aristolochic alkaloid compounds are inferred according to the method.
Wherein 18 aconite alkaloids are identified by co-separation, taking compound 11 as an example (figure 2), in positive ion mode, the primary mass spectrum M/z of compound 11 is 646.3199 [ M+H ] +, the fragment ions M/z observed by the secondary mass spectrum are 614.29416, 586.29921, 570.30447, 554.27359, 522.28237 and 368.18411 respectively generated by [M+H-CH3OH]+、[M+H-CH3COOH]+、[M+H-CH3COOH-H2O]+、［M+H-CH3COOH-CH3OH]+、[M+H-CH3COOH-3CH3OH-C6H5COOH], the compound is inferred to be aconitine according to molecular weight, ion fragment information and compound database, and the rest aconite alkaloid compounds are inferred according to the method.
Wherein, 9 pyrrolizidine alkaloids are identified by co-separation, taking compound 26 as an example (figure 3), in a positive ion mode, M/z is 366.19088 [ M+H ] +, fragment ions M/z are 348.18072, 168.10164, 150.09096 and 122.05917 from a secondary mass spectrogram, the corresponding ions are [M+H-H2O]+、[M+H-C10H14O4(necic acid)]+、[M+H-C10H14O4(necic acid)-H2O]+、[M+H-C10H14O4(necic acid)-H2O-CO]+, respectively, the compound is inferred to be the k-senecine according to molecular weight, ion fragment information and a compound database, and the rest pyrrolizidine alkaloids compounds are inferred according to the method.
In the positive ion mode, the M/z of the compound 46 is 868.59372 [ M+H ] +, the fragment ions are 850.49265, 722.44697, 704.43586 and 558.37915, the corresponding ions are [M+H-H2O]+、[M+H-Rha]+、[M+H-Rha-H2O]+、[M+H-Rha-Glu]+,, the compound is estimated to be solanine according to the molecular weight, ion fragment information and a compound database, and the rest alkaloid compounds are all estimated according to the method.
TABLE 2 isolation of the identified alkaloids from 43 Chinese herbs
The foregoing description is only of the preferred embodiments of the invention, and all changes and modifications that come within the meaning and range of equivalency of the claims are therefore intended to be embraced therein.

Claims (2)

1. A method for rapidly screening toxic alkaloids in Chinese herbal medicines based on UPLC-QTOF-MS technology combined UNIFI, which is characterized by comprising the following steps:
Step a), grinding the dried Chinese herbal medicines into powder, and sieving; mixing the Chinese herbal medicine powder with a solvent, performing ultrasonic extraction at room temperature, centrifuging, filtering the supernatant by an organic filter membrane to obtain a sample, and storing the sample in a sample bottle for sample injection;
Step b), separating and detecting the sample prepared in the step a) by using an ultra-high performance liquid chromatography tandem mass spectrometer to obtain an alkaloid component substance peak, and carrying out qualitative analysis on the substance peak by using UNIFI software;
in the step a), the solvent is methanol, and the ratio of the Chinese herbal medicine powder to the solvent is 1:100 m/v;
in the step a), the ultrasonic extraction time is 30 min, the ultrasonic power is 200W, and the ultrasonic frequency is 40 kHz;
in step a), the centrifugation conditions are 10000 rpm, 10 min;
In the step a), the supernatant is filtered by a 0.45 mu m organic filter membrane and a 0.22 mu m organic filter membrane in sequence;
In step b), the chromatographic separation conditions are: the chromatographic column is ACQUITY UPLC BEH C 18, the specification of the chromatographic column is 2.1 mm multiplied by 100 mm, and the size of the chromatographic column is 1.7 mu m; sample injection amount is 1 mu L, flow rate is 0.2 mL/min, and column temperature is 40 ℃; the mobile phase of the elution system is: mobile phase A is water containing 10 mM ammonium formate, mobile phase B is methanol; gradient elution is performed by ：0-1 min,95% A;1-3 min,95% A→70% A;3-12 min,75% A→55% A;12-20 min,55% A→1% A;20-25 min,1% A;25-25.1 min,1% A→95% A;25.1-30 min,95% A;
In step b), the conditions for mass spectrometry detection are: an electrospray ion source, MSE positive ion scan mode; nitrogen is the reverse blowing, desolventizing and atomizing gas of the taper hole, and argon is the collision gas; capillary voltage 2.00 kV, taper hole voltage 40V, ion source temperature 150 ℃, desolvation gas flow rate 600L/h, desolvation gas temperature 350 ℃, taper hole gas flow rate 50L/h, low energy collision voltage 6V, high energy collision voltage 30-50V, mass scanning range 50-1200 Da, scanning time 0.250 s, and scanning time interval 0.250 s;
The toxic alkaloid is aristolochic acid I, aristolochic acid II, aristolochic acid III, aristolochic acid IV, aristololactam I, aristolochic ketone, 10-hydroxy aconitine, 14-benzoyl aconitine, and other drugs acetylaconitine, aconitine, cha Siman' S, deoxyaconitine, aconitine, aconitfor producing aconitine, aconite, aconitine, aconitfor producing aconitine aconitine, mesaconitine, neoconine, nimodine, sodium hydroxide, sodium Taraxacum, lycoramine-N-oxide, kjeldahl senecine, seal-metadine, integerrimine, cepharanthine-N-oxide, lansidine, seal-N-oxide, (-) -scopolamine, (S) - (-) -atropine, anisodamine, gelsemine B, gelsemine A, gelsemine C, gelsemine B, gelsemine, papaverine, protopine, solasodine and solasodine;
The Chinese herbal medicine is fructus Aristolochiae, herba Senecionis Scandentis, radix Aconiti lateralis Preparata, camptotheca acuminata, herba Aristolochiae Mollissimae, herba Lycopi, semen hyoscyami, nandina seed, radix Clematidis, herba Eupatorii, radix Anisodi Acutanguli, caulis et folium Nandinae Domesticae, herba asari, flos Farfarae, mao Sheding herba Golgi, rhizoma corydalis, radix Stephaniae Tetrandrae, herba cynoglossi, menispermi, radix Trigonellae, radix Aristolochiae, herba Aristolochiae, aristolochiae Kaempferi, herba Solani Nigri, caulis Clematidis, herba Paederiae, pseudobulbus Cremastrae seu pleiones, rhizoma Ligustici Chuanxiong, radix Saposhnikoviae, radix Aconiti, fructus evodiae, herba Dendrobii, radix Ledebouriellae, radix Aconiti Kusnezoffii, and herba Heterophyllae.
2. The method of claim 1, wherein in step b), the UNIFI software is model Waters UNIFI 1.8.
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CN109917066A (en) * 2019-04-30 2019-06-21 江阴天江药业有限公司 A method of lycopodium calvatum alkaloid component is detected based on UPLC-QTOF-MS

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CN112444592A (en) * 2020-11-11 2021-03-05 谱尼测试集团北京检验认证科学研究院有限公司 Method for rapidly screening active ingredients in liquorice by UPLC-Q-TOF-MS

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