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CN-121994947-A - Method for detecting monacolin compounds

CN121994947ACN 121994947 ACN121994947 ACN 121994947ACN-121994947-A

Abstract

The application discloses a method for detecting monacolin compounds. According to the application, a non-targeted screening thought is adopted, key sub-ions of 4 monacolin compounds are discovered for the first time, and by utilizing the characteristic that the monacolin compounds are easily cracked in a mass spectrum, a non-targeted screening method of the monacolin compounds based on key sub-ion detection is respectively established in a high-resolution mass spectrum and a triple quadrupole mass spectrum, so that the distribution and the content of the monacolin compounds can be specifically presented. Compared with the original analysis method of the monacolin compounds, the analysis method of the monacolin compounds can filter the interference of most other compounds, specifically present the distribution and the content of the monacolin compounds, can be applied to the detection of the distribution and the relative content of the monacolin compounds in the fermentation products of monacolin compound-producing strains such as monascus and aspergillus terreus and the products of the fermentation products, and can also be applied to the establishment of the quality control methods such as the monacolin compound fingerprint, the content measurement and the like in the above matrixes.

Inventors

  • HU QING
  • MAO XIUHONG
  • CAO YIMIN
  • CHEN SUYUN
  • FENG RUI
  • ZHOU HENG
  • CHEN RUONAN
  • JI SHEN
  • WANG SHAOMIN
  • PAN HUIQIN
  • HUANG XIAOJING
  • LAN LAN

Assignees

  • 上海市食品药品检验研究院

Dates

Publication Date
20260508
Application Date
20241108

Claims (10)

  1. 1. A method for detecting monacolin compounds is characterized by comprising the step of analyzing a sample to be detected by using a liquid chromatography-mass spectrometer, wherein the mass spectrometry condition of the liquid chromatography-mass spectrometer comprises the steps of collecting C 19 H 23 O 2 + 、C 19 H 25 O 2 + 、C 19 H 27 O 2 + and C 19 H 29 O 2 + ions.
  2. 2. The method of claim 1, wherein the liquid chromatograph-mass spectrometer is selected from any one of a liquid chromatograph tandem high resolution mass spectrometer and a liquid chromatograph tandem triple quadrupole mass spectrometer.
  3. 3. The method of claim 2, wherein the sample to be analyzed is analyzed using liquid chromatography tandem high resolution mass spectrometry having mass spectrometry conditions that include extracting ion streams having molecular weights of 283.1693.+ -.20 ppm, 285.1849.+ -.20 ppm, 287.2006.+ -.20 ppm, 289.2162.+ -.20 ppm.
  4. 4. The method of claim 3, wherein the mass spectrometry conditions of the liquid chromatography tandem high resolution mass spectrometry comprise: ion source, electrospray; Scanning mode: positive ion scanning mode ESI (+); Monitoring mode is Auto MS/MS or Scan; Collision gas N 2 ; Collision energies 10, 20 and 40eV.
  5. 5. The method of claim 2, wherein the sample to be analyzed is by using a liquid chromatography tandem triple quadrupole mass spectrometry whose mass spectrometry conditions include collecting ions having charge-to-mass ratios of 283.0+ -1, 285.0+ -1, 287.0 + -1, 289.0 + -1.
  6. 6. The method of claim 5, wherein the mass spectrometry conditions of the liquid chromatography tandem triple quadrupole mass spectrometry comprise: selecting an ion with a charge-to-mass ratio of 283.0+/-1 as a parent ion, and selecting at least one ion with a charge-to-mass ratio of 223.0+/-1, 237.0+/-1 and 265.0 +/-1 as a child ion; Selecting an ion with a charge-to-mass ratio of 285.0+/-1 as a parent ion, and selecting at least one ion with a charge-to-mass ratio of 225.0+/-1, 239.0+/-1 and 267.0 +/-1 as a child ion; Selecting an ion having a charge-to-mass ratio of 287.0 + -1 as a parent ion and at least one ion having a charge-to-mass ratio of 227.0+ -1, 241.0 + -1, 269.0+ -1 as a child ion, and Selecting an ion with a charge-to-mass ratio of 289.0 +/-1 as a parent ion, and selecting at least one ion with a charge-to-mass ratio of 229.0 +/-1, 243.0 +/-1 and 271.0+/-1 as a child ion; Preferably, an ion having a charge-to-mass ratio of 283.0±1 is selected as the parent ion, and an ion having a charge-to-mass ratio of 223.0±1 is selected as the child ion; Selecting an ion with a charge-to-mass ratio of 285.0+/-1 as a parent ion, and selecting an ion with a charge-to-mass ratio of 225.0+/-1 as a child ion; Selecting an ion having a charge-to-mass ratio of 287.0 + -1 as a parent ion and an ion having a charge-to-mass ratio of 227.0+ -1 as a child ion, and An ion having a charge-to-mass ratio of 289.0 ±1 was selected as a parent ion, and an ion having a charge-to-mass ratio of 229.0 ±1 was selected as a child ion.
  7. 7. The method of claim 6, wherein the mass spectrometry conditions of the liquid chromatography tandem triple quadrupole mass spectrometry comprise: The declustering voltage is 180V, ions with charge-to-mass ratio of 283.0+/-1 are selected as parent ions under 24eV collision capacity, and ions with charge-to-mass ratio of 223.0+/-1 are selected as child ions; the declustering voltage is 180V, ions with the charge-to-mass ratio of 285.0+/-1 are selected as parent ions under 24eV collision capacity, and ions with the charge-to-mass ratio of 225.0+/-1 are selected as child ions; Selecting ion with charge-to-mass ratio of 287.0 + -1 as parent ion and ion with charge-to-mass ratio of 227.0+ -1 as child ion under declustering voltage of 200V and collision capacity of 22eV, and At a declustering voltage of 200V and a collision capacity of 24eV, ions with a charge-to-mass ratio of 289.0 + -1 are selected as parent ions, and ions with a charge-to-mass ratio of 229.0 + -1 are selected as child ions.
  8. 8. The method of claim 7, wherein the mass spectrometry conditions of the liquid chromatography tandem triple quadrupole mass spectrometry comprise: Ion source, electrospray, positive ion scanning mode ESI (+); the monitoring mode is MRM mode, and the temperature of the ion source is 200-600 ℃ (preferably 450 ℃).
  9. 9. The method of any one of claims 1-8, wherein the chromatographic conditions of the liquid chromatography-mass spectrometer comprise: The chromatographic column is an EC-C18 chromatographic column; The mobile phase is acetonitrile as the organic phase and 0.1% formic acid solution as the mobile phase as the aqueous phase; The elution mode is gradient elution.
  10. 10. The method of claim 9, wherein the chromatographic conditions of the liquid chromatography tandem triple quadrupole mass spectrometry comprise: the procedure for the gradient elution was as follows: 。

Description

Method for detecting monacolin compounds Technical Field The invention relates to the field of analysis and detection, in particular to a method for detecting monacolin compounds. Background Red rice originates from China, is called Danqu in ancient times, is also called red rice, and is a dry rice grain obtained by inoculating and fermenting rice with red aspergillus (Monascus spp.). Since the 20 th century 70 th Japanese scientist Yuanteng chapter separated from Monascus purpureus went for the first time, the hypolipidemic component monacolin K (lovastatin) was obtained, after lovastatin was developed as a hypolipidemic drug, monascus purpureus went as a research hotspot of pharmacy, and has higher economic value. The literature shows that the red rice contains abundant secondary metabolites, wherein the monacolin compounds are the main sources of the hypolipidemic activity of the red rice, the red rice can produce a plurality of monacolin compounds, the content distribution of the compounds is directly related to the hypolipidemic effect of the red rice, so that various researches are always focused on comprehensively analyzing and detecting the monacolin compounds in the red rice. At present, a great deal of literature is used for researching monacolin compounds in monascus fermentation products, including the material foundation research of monascus fermentation products, liquid fermentation products and monascus fermentation product extracts on solid matrixes such as rice, sorghum, highland barley and the like. The method for identifying 84 monacolins in red yeast rice by using a liquid phase-quadrupole-mass spectrometry combined technology by Li Meng-Ning and the like is the most complete research on the analysis of the monacolins in red yeast rice so far (ANALYTICA CHIMICA ACTA982 (2017) 156-157). Liang Jin Xiu et al identified 39 monacolins in red yeast rice by liquid phase-quadrupole-mass spectrometry (Journal of Ethnopharmacology (2019) 111879), chen Jia et al analyzed the product composition of red yeast rice and highland barley as solid fermentation bases, respectively (Food and Fuction (2022) 7000). The current detection method for the red Qu Mizhong monacolin compounds is focused on the detection of lovastatin and ring-opened lovastatin, and the detection of other monacolin compounds in red yeast rice is less. In the prior art Li Yongguo and the like develop a high performance liquid chromatography detection method aiming at 12 monacolin compounds, wang Mingjuan and the like detect a commercial red yeast rice sample by adopting a fingerprint method of Zhuikang raw material red yeast rice in Chinese pharmacopoeia. The method is characterized in that a high-resolution liquid-phase mass spectrometry method is adopted for substance basic research of the monacolin compounds, a parent ion and secondary spectrogram matching mode is adopted for identification, but the high-resolution liquid-phase mass spectrometry method depends on experimenters to identify the monacolin compounds according to literature data, the time is long, the experience requirements of the experimenters are high, in addition, the high-resolution liquid-phase mass spectrometry method can only be developed for specific monacolin compounds and depends on the physical property of ultraviolet absorption of the specific monacolin compounds for detection, however, part of monacolin compounds have no ultraviolet absorption, so that the whole analysis of the monacolin compounds cannot be carried out, and the discovery and identification of new monacolin compounds need extremely large workload of spectrogram analysis and are time-consuming and labor-consuming. In summary, the methods of loading in the current standards and the methods in the literature cannot be used for comprehensive analysis of the red Qu Mizhong monacolins, and even more for discovery of new monacolins in red yeast rice. There is a need in the art to develop new quality control methods for red yeast rice to comprehensively detect red Qu Mizhong monacolins. Disclosure of Invention The invention aims to provide a method for detecting monacolins. Another object of the present invention is to provide a quality control method of red rice. In order to solve the technical problems, the first aspect of the invention provides a method for detecting monacolin compounds, which comprises the steps of analyzing a sample to be detected by using a liquid chromatograph, wherein the mass spectrum condition of the liquid chromatograph comprises acquisition C19H23O2+、C19H25O2+、C19H27O2+ and C 19H29O2+ ions. In some preferred embodiments, the sample to be tested is a red yeast rice sample. In some preferred schemes, the method also comprises pretreatment of the sample to be tested before the sample introduction detection, and comprises the step of dissolving the sample to be tested by using a mixed solution of acetonitrile and water. In some preferred schemes, the pretreatment of the sam