CN116332825A - Preparation method of aristolochia lactam component in houttuynia cordata - Google Patents

Preparation method of aristolochia lactam component in houttuynia cordata Download PDF

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CN116332825A
CN116332825A CN202111606693.5A CN202111606693A CN116332825A CN 116332825 A CN116332825 A CN 116332825A CN 202111606693 A CN202111606693 A CN 202111606693A CN 116332825 A CN116332825 A CN 116332825A
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lactam
aristolochia
methanol
aristololactam
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卢燕
徐子砚
陈道峰
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Fudan University
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    • C07D209/00—Heterocyclic compounds containing five-membered rings, condensed with other rings, with one nitrogen atom as the only ring hetero atom
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Abstract

The invention belongs to the technical field of traditional Chinese medicine pharmacy, and relates to a preparation method of an aristolochia lactam component in houttuynia cordata. The invention establishes a method for rapidly enriching the aristololactam components from houttuynia cordata (Houttuynia cordata) by adopting a high-speed countercurrent chromatography technology, wherein three lactam components, namely aristololactam A II, aristololactam F I and aristololactam B II, are enriched from houttuynia cordata. Further provides a necessary reference substance for the safety evaluation and quality control of the traditional Chinese medicine houttuynia cordata.

Description

Preparation method of aristolochia lactam component in houttuynia cordata
Technical Field
The invention belongs to the field of traditional Chinese medicine pharmacy, relates to a preparation method of aristololactam components in houttuynia cordata, and in particular relates to a method for enriching aristololactam A II, aristololactam F I and aristololactam B II from houttuynia cordata.
Background
The prior art discloses that houttuynia cordata is fresh whole herb or dry overground part of houttuynia cordata (Houttuynia cordata) of Saururaceae, mainly produced in the middle part of China, each region from southeast to southwest, has the effects of clearing heat and detoxicating, eliminating carbuncles and expelling pus, and inducing diuresis and treating stranguria, is often used as vegetables or seasonings by people in southwest of China, and belongs to a first medicinal and edible homologous traditional Chinese medicine variety approved by Wei Jian Committee of China. Modern pharmacological researches have found that houttuynia cordata has antibacterial, anti-inflammatory, antiviral and anticomplement activities, and is mostly used for treating enteritis, dysentery, nephritic edema, mastitis, tympanitis and the like, which suggests that houttuynia cordata has wide use value.
Studies have disclosed that aristolochic acid components are widely present in plants of the Aristolochiaceae family (Aristolochiaceae), and have been demonstrated to have nephrotoxic, carcinogenic and mutagenic effects. The aristololactam component is a major metabolite of aristolochic acid components, and is not only present in plants of the family aristolochiaceae but also distributed in houttuynia cordata. There have been studies demonstrating that the compound aristololactam I is more nephrotoxic than aristolochic acid I! Preliminary researches of the research team also find that a plurality of aristololactam components in the cordate houttuynia have similar structures with the aristololactam I, have obvious cytotoxicity to renal tubular epithelial cells HK-2, and suggest that the preparation of the component reference substance has important significance for quality control and safe and reasonable application of the cordate houttuynia.
Research practice shows that the content of the aristololactam in the cordate houttuynia is very low, and the cost for preparing the reference substance by the traditional column chromatography separation process is high and the yield is low. Thus, the establishment of a method for rapid enrichment of aristolochia lactam compounds from houttuynia cordata has attracted attention by those skilled in the art.
Based on the current state of the art, the inventor of the application aims to provide a method for rapidly enriching the aristolochic lactam component from houttuynia cordata, and the method can be helpful for providing necessary research samples and reference substances for deep toxicology research, safety evaluation and quality control of the aristolochic lactam component in Chinese herbal medicines.
Disclosure of Invention
The invention aims at providing a preparation process of aristololactam components in houttuynia cordata based on the current state of the art, and particularly relates to a method for enriching aristololactam A II, aristololactam F I and aristololactam B II from houttuynia cordata.
The three aristolochia lactam components have the following structural formula:
Figure BDA0003434194130000021
the technical scheme adopted by the invention for achieving the purpose is as follows:
a method for preparing aristololactam a II, aristololactam F I, aristololactam BII from houttuynia cordata, comprising the steps of:
(1) Extracting herba Houttuyniae with organic solvent such as methanol or ethanol for several times, mixing extractive solutions, concentrating, recovering solvent, and evaporating to obtain extract. The extraction method can adopt flash extraction, ultrasonic extraction or percolation extraction.
(2) Suspending the extract obtained in the step (1) with water, extracting with petroleum ether, dichloromethane or ethyl acetate for 4 times, mixing the extracts, concentrating, recovering solvent, and evaporating to dryness to obtain extract.
(3) Separating the extract obtained in the step (2) by normal phase silica gel column chromatography, and performing gradient elution by using 5-7 times of column volume of dichloromethane-methanol (120:1, 50:1, 10:1, 1:1) or dichloromethane-methanol (100:1, 50:1, 20:1, 10:1), and collecting eluting parts of dichloromethane-methanol (50:1, 10:1) or dichloromethane-methanol (50:1, 20:1) according to Liquid Chromatography Mass Spectrometry (LCMS) analysis results to obtain crude extracts of the aristololactam components.
Enriching the crude extract obtained in the step (3) through high-speed countercurrent chromatography, selecting an n-hexane-ethyl acetate-methanol-water (1:2:1.55:1.45) or n-hexane-ethyl acetate-methanol-water (1:2:1.5:1.5) system, taking the upper phase (n-hexane-ethyl acetate) as a stationary phase, taking the lower phase (methanol-water) as a mobile phase, distributing under the conditions of a flow rate of 2.0mL/min and a host rotating speed of 850r/min, detecting the wavelength of 280nm, determining the peak position of the aristolochic acid amide component according to an LCMS characteristic spectrum, collecting the effluent in the place, concentrating and recovering the solvent, and evaporating to dryness to obtain the aristolochic acid amide component enrichment.
(4) Purifying the concentrate obtained in the step (4) by high performance liquid chromatography, eluting with C18 chromatographic column (250×20mm,5 μm) at 25deg.C and acetonitrile-water (50:50) or (53:47) at flow rate of 10mL/min, and collecting main chromatographic peaks to obtain Aristolochia lactam A II, aristolochia lactam F I and Aristolochia lactam B II.
The invention establishes a method for rapidly enriching the aristololactam components from houttuynia cordata (Houttuynia cordata) which is a houttuynia plant by adopting a high-speed countercurrent chromatography technology, and enriches three lactam components of aristololactam A II, aristololactam F I and aristololactam B II from houttuynia cordata, thereby further providing necessary reference substances for the safety evaluation and quality control of the houttuynia cordata which is a traditional Chinese medicine for clearing heat and detoxicating.
The invention has the following beneficial effects:
the enrichment process of the aristolochia debilis lactam component provided by the invention is simple, convenient and rapid, has high yield, is suitable for industrial preparation, and can be used for large-scale enrichment of the aristolochia debilis lactam compound reference substance in the Chinese herbal medicine.
Drawings
FIG. 1 shows the structures of Aristolochia lactam A II (AL AII), aristolochia lactam F I (AL FI), aristolochia lactam B II (AL BII).
FIG. 2 is a schematic diagram of the enrichment process according to example 1, example 6, and example 8.
FIG. 3 is a multi-level mass spectrum of aristololactam A II, aristololactam F I, and aristololactam B II in example 5.
FIG. 4 shows the putative cleavage pathways of Aristolochia lactam A II, aristolochia lactam F I, aristolochia lactam B II in example 5.
FIG. 5 is a liquid chromatogram of samples HH-PE1 to HH-PE11 in example 6.
FIG. 6 is a high-speed countercurrent chromatography of sample HH-PE-H in example 8.
Detailed Description
Example 1: extraction and extraction of houttuynia cordata
Taking 5kg of underground part of houttuynia cordata, crushing by a crusher, adding 100L of methanol, performing flash extraction for 5min at a voltage of 100V for 1 time, combining filtrates, concentrating and evaporating to dryness to obtain 1279.62g of extract; the extract was dispersed in 4L of water, and extracted with petroleum ether 4 times to obtain 152.38g of petroleum ether extract (shown in FIG. 1).
Example 2: extraction and extraction of houttuynia cordata
Taking 19kg of cordate houttuynia, crushing the cordate houttuynia by a crusher, soaking the crushed cordate houttuynia in 95% ethanol for 96 hours after soaking the crushed cordate houttuynia in 95% ethanol for all night, adding 95% ethanol with a feed-liquid ratio of 1:10 every day, merging filtrate, concentrating and evaporating the filtrate, and extracting the extract by petroleum ether for 4 times to obtain 273.82g of petroleum ether extracted parts.
Example 3: extraction and extraction of houttuynia cordata
Taking 5.05g of cordate houttuynia, crushing by a crusher, adding 100mL of methanol, carrying out ultrasonic treatment for 30min for 3 times, combining the filtrates, concentrating and evaporating to dryness to obtain 1.96g of methanol extract; the extract was dispersed in 10mL of water, and extracted with methylene chloride 4 times to obtain 0.12g of a methylene chloride extract.
Example 4: extraction and extraction of houttuynia cordata
Taking 5.03g of cordate houttuynia, crushing by a crusher, adding 100mL of methanol, carrying out ultrasonic treatment for 30min for 3 times, combining the filtrates, concentrating and evaporating to dryness to obtain 1.63g of methanol extract; the extract was dispersed in 10mL of water, and extracted with ethyl acetate 4 times to obtain 0.12g of an ethyl acetate extract.
Example 5: UPLC-MS of characteristic peak of target object n Identification of
The chromatographic separation was carried out using a YMC-Triart C18 column (150X 2.1mm,1.9 nm). The column temperature is 30 ℃, the flow rate is 0.3mL/min,0.1 percent formic acid water-acetonitrile gradient elution (0-2 min,10 percent acetonitrile; 2-12min,10-40 percent acetonitrile; 12-32min,40-50 percent acetonitrile; 32-45min, 50-100 percent acetonitrile; 45-55min,100 percent acetonitrile; 55-60min,100-10 percent acetonitrile; 60-65min,10 percent acetonitrile), the sample injection amount is 5 mu L, and the wavelength is 277nm. The primary mass spectrum adopts electrospray ion source (ESI) positive ion mode full-scan detection, and the secondary and tertiary mass spectra adopt data dependency scanning. The mass range m/z is 100.0-1000.0. The capillary temperature is 350 ℃, the capillary voltage is 35V, the spray voltage is 3.5KV, the sheath air flow rate is 40psi, and the auxiliary air flow rate is 10psi.
Taking Aristolochia lactam A II, aristolochia lactam F I and Aristolochia lactam B II as reference substances, and collecting primary, secondary and tertiary mass spectrograms (shown in figure 2). Aristolochia lactam A II, aristolochia lactam F I and Aristolochia lactam B II all form [ M+H ] in positive ion mode] + Ions. Aristolochia lactam A II and Aristolochia lactam F I are isomers, and CH is removed by both secondary mass spectrometry 3 Formation of m/z 251[ M+H-CH ] 3 ] + Ion, tertiary mass spectrometry can see low abundancem/z 223[M+H-CH 3 -CO] + The ion, but the higher abundance M/z 195 is presumed to be [ M+H-CH ] 3 -CO-HCN-H] + Ions. Secondary mass spectrometry of aristololactam B II likewise first removes CH 3 Formation of m/z 265[ M+H-CH ] 3 ] + Ion, tertiary mass spectrum is m/z 264[ M+H-CH ] 3 -H] + The ions, the left substituent presumably forms a closed loop structure of methylenedioxy (as shown in FIG. 3). According to the retention time (t R ) And mass spectrum characteristic fragment information can identify the aristololactam A II, the aristololactam F I and the aristololactam B II.
TABLE 1 mass spectrum fragmentation information of Aristolochia lactam Components in houttuynia cordata
Figure BDA0003434194130000041
Example 6: normal phase silica gel column chromatographic separation of cordate houttuynia extraction part
Mixing the petroleum ether extraction part in example 1 with 2kg of silica gel (200-300 meshes), eluting 3 column volumes with dichloromethane-methanol as an eluting system at a ratio of 120:1, eluting 1 column volume with 50:1, eluting 1 column volume with 10:1, eluting 1 column volume again with 1:1, and preliminarily combining the eluted components into 11 components (HH-PE 1-HH-PE 11) by Thin Layer Chromatography (TLC) spot plate according to UPLC-MS n The target components (as shown in FIG. 4) were tracked by profile, HH-PE 6-HH-PE 10 were collected and pooled to give 26.14g of HH-PE-H fraction eluted mainly from methylene chloride-methanol (50:1, 10:1).
Example 7: normal phase silica gel column chromatographic separation of cordate houttuynia extraction part
The petroleum ether extraction site in example 2 was stirred with 3.5kg of silica gel (200 to 300 mesh) and dichloromethane-methanol was used as an elution system, 100: eluting 3 column volumes in proportion of 1, eluting 2 column volumes in proportion of 50:1, eluting 1 column volume in proportion of 20:1, eluting 1 column volume again in proportion of 10:1, performing gradient elution with normal phase silica gel chromatographic column, and primarily combining the eluted components into 8 components (HH-PE 1-HH-PE 8) by Thin Layer Chromatography (TLC) point plate according to UPLC-MS n The target components were tracked by profile, HH-PE 5-HH-PE 7 were collected and pooled to give 57.78g of HH-PE-H fraction, which was eluted mainly from methylene chloride-methanol (50:1, 20:1).
Example 8: high-speed countercurrent chromatography enrichment and semi-preparative high-performance liquid chromatography purification
The HH-PE-H component in example 6 was suspended with a small amount of an upper phase (n-hexane-ethyl acetate), eluted with a high-speed countercurrent chromatography, the upper phase was a stationary phase, the lower phase was a mobile phase, the flow rate was 2.0mL/min, the rotation speed was 850r/min, the temperature was 25℃and the loading amount was about 1000mg each time, data were collected at an online chromatographic workstation, 10 components HH-PE-H1 to HH-PE-H10 (as shown in FIG. 5) were collected and obtained from the peaks of ultraviolet chromatography, and the components HH-PE-H7 and HH-PE-H9 containing the aristololactam were collected, respectively, according to UPLC-MS/MS (detection conditions and example 5) analysis results (as shown in FIG. 6), and the solvent was recovered under reduced pressure, thereby obtaining enriched components HH-PE-H7 component 259.07mg and HH-PE-H9 component 218.91mg, respectively;
HH-PE-H7 component was purified by reverse phase high performance liquid chromatography eluting isocratically with acetonitrile-water (53:47), flow rate 10mL/min, detection wavelength 280nm, column temperature: collecting components for 11.1-11.3 min and 12.3-12.7 min at room temperature, and recovering solvent under reduced pressure to obtain Aristolochia lactam A II (5.35 mg) and Aristolochia lactam F I (7.08 mg); purifying HH-PE-H9 component by reverse phase high performance liquid chromatography, eluting with acetonitrile-water (50:50) isocratic, flowing at 10mL/min, detecting wavelength of 280nm, and column temperature: collecting the components for 19.4-20.1 min at room temperature, and recovering the solvent under reduced pressure to obtain aristololactam B II (34.76 mg).
Example 9: high-speed countercurrent chromatography enrichment and semi-preparative high-performance liquid chromatography purification
The HH-PE-H component in example 7 was suspended with a small amount of an upper phase (n-hexane-ethyl acetate), eluted with a high-speed countercurrent chromatography, the upper phase was a stationary phase, the lower phase was a mobile phase, the flow rate was 2.0mL/min, the rotation speed was 850r/min, the temperature was 25℃and the loading amount was about 1000mg each time, data were collected at an online chromatographic workstation, 12 components HH-PE-H0 to HH-PE-H11 were collected and obtained from the ultraviolet chromatographic peaks, and the components HH-PE-H6 and HH-PE-H9 containing the aristololactam were collected, respectively, and the solvent was recovered under reduced pressure according to the UPLC-MS/MS (detection conditions were the same as in example 5) analysis results, thereby obtaining an enriched component HH-PE-H6 component 449.93mg and HH-PE-H9 component 519.84mg, respectively.
Purifying HH-PE-H6 component by reverse phase high performance liquid chromatography, eluting with acetonitrile-water (53:47) isocratic, flowing at 10mL/min, detecting wavelength of 280nm, and column temperature: collecting components for 11.0-11.4 min and 12.2-12.7 min at room temperature, and recovering solvent under reduced pressure to obtain Aristolochia lactam A II (18.59 mg) and Aristolochia lactam F I (24.59 mg); purifying HH-PE-H9 component by reverse phase high performance liquid chromatography, eluting with acetonitrile-water (50:50) isocratic, flowing at 10mL/min, detecting wavelength of 280nm, and column temperature: collecting the components for 19.2-19.8 min at room temperature, and recovering the solvent under reduced pressure to obtain aristololactam B II (165.06 mg).
The present invention has been described in terms of the above-described embodiments, it will be appreciated by those skilled in the art that changes, modifications, substitutions and alterations may be made to these embodiments without departing from the principles and spirit of the invention, the scope of which is defined in the appended claims and their equivalents.

Claims (7)

1. A preparation method of an aristolochia lactam component in houttuynia cordata is characterized by comprising the following steps:
(1) Mixing herba Houttuyniae with organic solvent at a certain ratio, extracting for several times, mixing extractive solutions, and recovering solvent to obtain extract;
(2) Suspending the extract obtained in the step (1) with water, extracting with organic solvent for several times, mixing the extractive solutions, and recovering solvent to obtain extract;
(3) Eluting the extract obtained in the step (2) by normal phase silica gel column chromatography with a dichloromethane-methanol mixed solvent, performing liquid chromatography-mass spectrometry analysis on each tube of eluent, collecting and combining the eluent containing the aristololactam component, and recovering the solvent to obtain a crude extract of the aristololactam component;
(4) Separating the crude extract obtained in the step (3) by high-speed countercurrent chromatography, and collecting and combining the eluent containing the aristolochic lactam component according to the liquid chromatography-mass spectrometry analysis result of the eluent to obtain an aristolochic lactam component enrichment substance;
(5) Separating the concentrate obtained in the step (4) by high performance liquid chromatography, taking acetonitrile-water mixed solvent as mobile phase, collecting chromatographic peak containing Aristolochia lactam component, and recovering solvent to obtain Aristolochia lactam A II, aristolochia lactam F I and Aristolochia lactam B II respectively.
2. The process of claim 1 wherein said organic solvent of step (1) is selected from the group consisting of methanol and ethanol.
3. The method of claim 1, wherein the extraction method of step (1) is selected from flash extraction, ultrasonic extraction, or percolation extraction.
4. The process of claim 1, wherein the organic solvent of step (2) is selected from petroleum ether, methylene chloride, or ethyl acetate.
5. The method of claim 1, wherein the elution conditions of the normal phase silica gel column chromatography of step (3) are: the dichloromethane-methanol is eluted according to the proportion gradient of 120:1, 50:1, 10:1 and 1:1 or the dichloromethane-methanol is eluted according to the proportion gradient of 100:1, 50:1, 20:1 and 10:1, and the eluting part of the dichloromethane-methanol 50:1, 10:1 or the dichloromethane-methanol 50:1 and 20:1 is collected.
6. The method of claim 1, wherein the separation conditions of the high-speed countercurrent chromatography of step (4) are: an n-hexane-ethyl acetate-methanol-water system mixed with 1:2:1.55:1.45 or 1:2:1.5:1.5 is adopted, the n-hexane-ethyl acetate is used as a stationary phase, and the methanol-water is used as a mobile phase.
7. The method according to claim 1, wherein in the separation by high-speed countercurrent chromatography in the step (4), the chromatographic peak containing the aristololactam component is determined based on the ultraviolet spectrum or mass spectrum of the effluent, and the effluent corresponding to the combination is collected.
CN202111606693.5A 2021-12-26 2021-12-26 Preparation method of aristolochia lactam component in houttuynia cordata Pending CN116332825A (en)

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Cited By (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
CN117379420A (en) * 2023-12-12 2024-01-12 中国中医科学院中药研究所 Use of aristololactam BII in preparation of leukocyte-increasing products

Cited By (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
CN117379420A (en) * 2023-12-12 2024-01-12 中国中医科学院中药研究所 Use of aristololactam BII in preparation of leukocyte-increasing products
CN117379420B (en) * 2023-12-12 2024-02-13 中国中医科学院中药研究所 Use of aristololactam BII in preparation of leukocyte-increasing products

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