CN116969945B - Indole alkaloid compound and extraction method and application thereof - Google Patents

Indole alkaloid compound and extraction method and application thereof Download PDF

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CN116969945B
CN116969945B CN202311187661.5A CN202311187661A CN116969945B CN 116969945 B CN116969945 B CN 116969945B CN 202311187661 A CN202311187661 A CN 202311187661A CN 116969945 B CN116969945 B CN 116969945B
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alkaloid compound
indole alkaloid
column chromatography
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CN116969945A (en
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白媛媛
王志伟
夏红旻
王变利
刘月程
王博阳
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Shandong Academy of Chinese Medicine
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    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D471/00—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, at least one ring being a six-membered ring with one nitrogen atom, not provided for by groups C07D451/00 - C07D463/00
    • C07D471/12—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, at least one ring being a six-membered ring with one nitrogen atom, not provided for by groups C07D451/00 - C07D463/00 in which the condensed system contains three hetero rings
    • C07D471/14—Ortho-condensed systems
    • A—HUMAN NECESSITIES
    • A23—FOODS OR FOODSTUFFS; TREATMENT THEREOF, NOT COVERED BY OTHER CLASSES
    • A23L—FOODS, FOODSTUFFS, OR NON-ALCOHOLIC BEVERAGES, NOT COVERED BY SUBCLASSES A21D OR A23B-A23J; THEIR PREPARATION OR TREATMENT, e.g. COOKING, MODIFICATION OF NUTRITIVE QUALITIES, PHYSICAL TREATMENT; PRESERVATION OF FOODS OR FOODSTUFFS, IN GENERAL
    • A23L33/00—Modifying nutritive qualities of foods; Dietetic products; Preparation or treatment thereof
    • A23L33/10—Modifying nutritive qualities of foods; Dietetic products; Preparation or treatment thereof using additives
    • A23L33/105—Plant extracts, their artificial duplicates or their derivatives
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P29/00—Non-central analgesic, antipyretic or antiinflammatory agents, e.g. antirheumatic agents; Non-steroidal antiinflammatory drugs [NSAID]
    • A—HUMAN NECESSITIES
    • A23—FOODS OR FOODSTUFFS; TREATMENT THEREOF, NOT COVERED BY OTHER CLASSES
    • A23V—INDEXING SCHEME RELATING TO FOODS, FOODSTUFFS OR NON-ALCOHOLIC BEVERAGES AND LACTIC OR PROPIONIC ACID BACTERIA USED IN FOODSTUFFS OR FOOD PREPARATION
    • A23V2002/00—Food compositions, function of food ingredients or processes for food or foodstuffs

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  • Pain & Pain Management (AREA)
  • Animal Behavior & Ethology (AREA)
  • General Health & Medical Sciences (AREA)
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Abstract

The application discloses an indole alkaloid compound, and an extraction method and application thereof, and belongs to the technical field of biological medicines. The structural formula of the indole alkaloid compound is shown as follows:and include pharmaceutically acceptable salts and derivatives. The application separates and obtains the anti-inflammatory effect of the rock wool alpha-gin from the rock wool plant, is an indole alkaloid compound, and prepares a series of derivatives or pharmaceutically acceptable salts based on the indole alkaloid compound, which can inhibit the effect of NO release by macrophages, can obviously reduce the generation of COX-2, and has the drug development potential for preventing or treating inflammation.

Description

Indole alkaloid compound and extraction method and application thereof
Technical Field
The application belongs to the technical field of biological medicines, and particularly relates to an indole alkaloid compound, an extraction method and application thereof.
Background
The non-steroidal anti-inflammatory drug generally refers to an anti-inflammatory drug without a steroidal structure, has the effects of relieving fever, easing pain, diminishing inflammation and the like, is widely applied to relieving fever and pain symptoms clinically, and is used for treating rheumatoid arthritis and osteoarthritis, and the drug with the largest dosage is currently prescribed and non-prescribed. However, long-term use of non-steroidal anti-inflammatory drugs is liable to cause adverse reactions of gastrointestinal tract, kidney, liver and blood system, and therefore, searching for and developing non-steroidal anti-inflammatory drugs which are safe, effective and have little adverse reaction from natural plants or animals is an important point in recent years of development of natural anti-inflammatory drugs.
The rock wool (Alstonia rupestris) is a plant of the genus Hedyotis of the family oleander, is mainly distributed in the Guangxi Zhuang nationality of China, is rich in monoterpene indole alkaloid compounds with novel structures, and part of compounds have anti-inflammatory and anti-tumor biological activities. But has important significance in separating and purifying the effective components with anti-inflammatory effect from the rock wool sheep horn cotton.
Disclosure of Invention
Aiming at the problem of large side effect of non-steroidal anti-inflammatory drugs in the prior art, the application provides an indole alkaloid compound, an extraction method and application thereof, wherein the indole alkaloid compound is separated from rock wool and comprises pharmaceutically acceptable salts and derivatives, and has the potential of drug development for preventing or treating inflammation.
The application is realized by the following technical scheme:
an indole alkaloid compound has a structural formula shown in a formula I:
formula I.
Further, pharmaceutically acceptable salts and derivatives thereof are also included, wherein the pharmaceutically acceptable salts are acid addition salts derived from inorganic and organic acids; these salts may be obtained directly in the final isolation and purification of the compounds. The compound may be obtained by mixing the above compound with a predetermined amount of an acid as appropriate (for example, equivalent). These salts may be obtained by precipitation in solution and collected by filtration, or recovered after evaporation of the solvent, or by lyophilization after reaction in an aqueous medium. In some embodiments of the application, the pharmaceutically acceptable salts of the present application may be inorganic or organic acid salts of the compounds described above, such as the inorganic acids including hydrochloric acid, sulfuric acid, phosphoric acid, hydrobromic acid, and hydroiodic acid; the organic acid is selected from the group consisting of citric acid, tartaric acid, formic acid, oxalic acid, methanesulfonic acid, carbonic acid, succinic acid, benzoic acid, acetic acid, oxalic acid, p-toluenesulfonic acid, and p-bromobenzenesulfonic acid.
Further, the extraction method of the indole alkaloid compound comprises the steps of reflux-extracting or leaching the rock wool in an organic solvent I, adding water into the solution after extraction or leaching for suspension, extracting with an organic solvent II under an acidic condition, extracting a water layer with an organic solvent III under an alkaline condition, and separating the extracted organic layer by column chromatography to obtain the indole alkaloid compound.
Further, the pH of the acidic condition is 3, and the pH of the alkaline condition is 10; the organic solvent I, the organic solvent II and the organic solvent III are respectively C 1-6 Alcohols, C 3-6 Ketones, C 2-6 Ethers, C 2-6 Esters and C 1-6 One of the halogenated hydrocarbons.
Further, the C 1-6 The alcohol is one of methanol, ethanol, n-propanol, isopropanol, n-butanol, isobutanol, tertiary butanol, n-amyl alcohol, isoamyl alcohol, n-hexanol and cyclohexanol; the C is 3-6 The ketone is one of acetone, methyl ethyl ketone and methyl isobutyl ketone; the C is 2-6 The ether is methyl ether or diethyl ether; the C is 2- The 6 ester is one of ethyl formate, ethyl acetate and ethyl propionate; the C is 1-6 The halohydrocarbon is one of dichloromethane, chloroform and dichloroethane.
Further, the organic solvent I is C 1-6 The alcohol, the organic solvent II and the organic solvent III are C 1-6 Halogenated hydrocarbons; the eluent of the column chromatography is dichloromethane/methanol or petroleum ether/acetone.
Further, the organic solvent I is ethanol, the organic solvent II and the organic solvent III are methylene dichloride, the volume ratio of the methylene dichloride to the methanol in the eluent is 100:1-1:1, and the volume ratio of the petroleum ether to the acetone is 10:1-1:5.
Further, the method of column chromatography specifically comprises the following steps: sample mixing on silica gel, 200&Separating by 300 mesh silica gel column chromatography, dividing into 10 sections, namely R1-R10 section, R8 section Jing Guijiao column chromatography, performing gradient elution by using petroleum ether-acetone as a washing and dehydrating machine in a volume ratio of 10:1-1:5 to obtain 7 sections R8 a-R8 g, preparing liquid phase by the R8g section, and performing MeOH-H in a volume ratio of 73:27 2 O is eluent, and the indole alkaloid compound is separated.
In the application, the indole alkaloid compound is applied to the preparation of anti-inflammatory preparations, and the rock wool sheep's horn cotton first is an indole alkaloid compound with a novel structure, has good inhibiting effect on release activity of mouse macrophage Raw 264.7 NO induced by LPS, has slightly better effect than dexamethasone, and has good medicinal and health-care prospects; the preparation is a medicine, food or health care product, and can contain auxiliary materials which are consistent with the relevant addition regulations of the medicine, food and health care product, such as excipient, filler and the like, so that the preparation has a certain shape, and the taste of the preparation is good due to the taste correction agent and the like.
The beneficial effects obtained by the application are as follows:
the application separates and obtains the anti-inflammatory effect of the yankee sheep horn cotton from the yankee sheep horn cotton plant, is an indole alkaloid compound, and prepares a series of derivatives or pharmaceutically acceptable salts based on the indole alkaloid compound, which can inhibit the effect of NO release by macrophages and can obviously reduce the generation of COX-2, and the IC of the yankee sheep horn cotton 50 Has the drug development potential of preventing or treating inflammation between 1.0 and 20.0 mu M. IC of rock wool sheep horn cotton element for inhibiting macrophage from releasing NO activity 50 The activity of the dexamethasone is lower than 4.2+/-1.3 mu M, and the dexamethasone has good application prospect.
Drawings
FIG. 1 is a diagram of a rock wool horn cotton 1 H NMR chart;
FIG. 2 is a diagram of a rock wool horn cotton extract A 13 C NMR chart;
FIG. 3 is a graph showing the effect of bergenin on COX-2 protein expression, A is a gel electrophoresis image, and B is a bar graph.
Detailed Description
The application will be further illustrated with reference to specific examples. It is to be understood that these examples are illustrative of the present application and are not intended to limit the scope of the present application. The experimental procedures, which do not address the specific conditions in the examples below, are generally carried out under conventional conditions or under conditions recommended by the manufacturer.
Unless defined otherwise, all technical and scientific terms used herein have the same meaning as commonly understood by one of ordinary skill in the art. The reagents or materials used in the present application may be purchased in conventional manners, and unless otherwise indicated, they may be used in conventional manners in the art or according to the product specifications. In addition, any methods and materials similar or equivalent to those described herein can be used in the methods of the present application. The preferred methods and materials described herein are presented for illustrative purposes only.
Example 1
Taking dried rhizome 10 kg of a rock wool plant, heating and reflux-extracting for 3 times by using 95% ethanol, recovering a solvent until no alcohol smell exists, adding water, suspending, adjusting pH to 2 by using 2% HCl, extracting for 5 times by using dichloromethane, adjusting pH to 10 by using 10% NaOH for a water layer, extracting for 4 times by using dichloromethane, recovering dichloromethane from an organic layer to obtain total alkaloids, stirring by using silica gel, performing 200-300 mesh silica gel column chromatography, dividing into 10 sections (R1-R10), performing R8 by using silica gel column chromatography, using petroleum ether-acetone (10:1-1:5) as a gradient eluent, obtaining 7 sections (R8 a-R8 g), preparing a liquid phase by using MeOH-H in the R8g section 2 O (73:27) is used as an eluent to obtain the bergenin A.
The structural formula of the rock wool horn cotton A is determined by infrared spectrum, mass spectrum, one-dimensional and two-dimensional nuclear magnetic resonance spectrum. Infrared spectral data: IR (max, KBr): 3285, 2947, 2914, 1743, 1711, 1633, 1321 cm –1 The method comprises the steps of carrying out a first treatment on the surface of the Mass spectrometry data: HR-ESI-MS (m/z): 533.2287 [ M+H ]] + (calcd. 533.2288 [M+H] + )； 1 H NMR 13 The C NMR data are shown in Table 1, and the corresponding spectra are shown in FIG. 1 and FIG. 2. The above data combined with 2D NMR analysis confirm that the chemical structural formula (formula I) of the bergenin is shown in the following figure, which is the molecular weight 532.6 of the indole alkaloid compound, molecular formula C 30 H 32 N 2 O 7 The method comprises the steps of carrying out a first treatment on the surface of the A pale yellow powder; is easily dissolved in chloroform, dichloromethane and methanol.
TABLE 1 Keratin A 1 H NMR 13 C NMR data (CDCl) 3 Shown as superimposed signals
Formula I.
Example 2
The bergenin separated in example 1 was added to a 4% hydrochloric acid solution, ph=4 was adjusted, filtered and dried to prepare the bergenin hydrochloride.
Example 3
The crude yankee gossypin a separated in example 1 was added with a 4% sulfuric acid ethanol solution, ph=4 was adjusted, filtered, and dried to prepare the crude yankee gossypin sulfate.
Example 4
The rock wool sheep's horn cotton first separated in example 1 was added with 4% phosphoric acid solution, ph=4 was adjusted, filtered, dried to prepare rock wool sheep horn cotton first phosphate.
Example 5
The bergenin separated in example 1 was added with 4% citric acid solution, ph=4 was adjusted, filtered and dried to prepare citric acid bergenin.
Example 6
The bergenin separated in example 1 was added with 4% tartaric acid solution, ph=4 was adjusted, filtered and dried to produce the bergenin tartrate.
Example 7
The bergenin separated in example 1 was added with a 4% formic acid solution, ph=4 was adjusted, filtered, and dried to prepare a formic acid bergenin.
Example 8
The bergenin separated in example 1 was added with a 4% oxalic acid solution, ph=4 was adjusted, filtered, and dried to prepare the bergenin oxalate.
Application examples
Separating and obtaining compounds 1-6 (compound 1: tetrahydroalstonin, compound 2: beta-yohimbin, compound 3: 3-epi-alpha-yohimbin, compound 4: corynenthine, compound 5: yohimbin, compound 6: 19-dehydroyohimbin) and the yankee cotton methyl in the application, wherein the structural formula of the compounds 1-6 is as follows:
study on the inhibition activity of compound 1-6 and rock wool sheep's horn cotton factor A on LPS-induced macrophage NO release:
the test methods and results are as follows:
(1) Experimental materials
Cell lines: mouse macrophage Raw 264.7 cell line (cell center of university of chinese synergetic medical science).
Materials: DMEM high sugar medium (Hyclone, cat# 09231); trypsin-EDTA digest (Solarbio, cat# T1300); FBS (Biological Industries, cat# 04-121-1); NO kit (Biyun Tian, cat# S0021S); DMSO (Solarbio, cat# 302A 034); penicillin (Solarbio, cat# P1400); streptomycin (Solarbio, cat# 423A 054).
Reagent: the bergenin and compounds 1-6 prepared in example 1.
The positive control was dexamethasone.
(2) Experimental method
Taking cells of 2-5 generations with good growth state, discarding the original culture solution when the growth of the cells is covered to about 90%, replacing a new 10 mL DMEM complete culture medium containing 10% new born calf serum, and resuspending the cells according to a passage method;
the counted cell suspension was diluted to a concentration of 1X 10 in DMEM complete medium with 10% new born calf serum 5 Cell suspension of each mL was prepared by taking 96-well cell culture plates, adding 100. Mu.L of diluted cell suspension to each well, and adding 5% CO at 37 ℃to the wells 2 The culture was carried out in an incubator with adhesion to 24. 24 h.
Cells were divided into four groups: normal control group, LPS model control group, sample group, positive control group. (1) Normal control group:no LPS cell group was added; (2) LPS model control group: preparing LPS solution with complete medium containing 10% FBS to concentration of 200 ng/mL, and arranging six compound holes with 100 μl each; (3) sample group: the sample was dissolved in complete medium with LPS concentration of 200 ng/mL, and final concentrations of 100. Mu.M (C1), 50. Mu.M (C2), 25. Mu.M (C3), 12.5. Mu.M (C4), 6.3. Mu.M (C5) and 3.1. Mu.M (C6) were prepared, respectively, and six duplicate wells were set for each concentration, and 100. Mu.L was added to each well; (4) positive control group: dexamethasone (DEX) was dissolved in complete medium with LPS concentration of 200 ng/mL, final concentration of 10. Mu.M, six duplicate wells were set, and 100. Mu.L was added to each well; normal control group: adding the same amount of complete medium (C0), 37 ℃ and 5% CO 2 Culture 24 h in incubator.
And (3) detection: (1) NaNO 2 Dilution of standard solution: naNO is processed by 2 The standard solution was diluted to 500 ng/mL, 250 ng/mL, 125 ng/mL, 62.5 ng/mL, 31.3 ng/mL, 15.6 ng/mL, and 7.8 ng/mL with complete medium. (2) Respectively taking diluted NaNO 2 50. Mu.L of standard solution and cell culture supernatant from a 96-well cell culture plate were added to a fresh 96-well cell culture plate, 50. Mu.L of room temperature Griess Reagent I was added to each well, and then 50. Mu.L of room temperature Griess Reagent II was added to each well. The absorbance value of each well was measured at the microplate reader 540 nm, and a standard curve was prepared, from which the NO release inhibition rate could be calculated.
Effects on COX-2 protein level expression: cells were collected and lysed with cell lysis buffer. Protein concentration was determined using protein assay reagents. Total cellular proteins (20. Mu.g) were separated by 10% SDS-polyacrylamide gel electrophoresis and transferred onto PVDF membrane; the membrane was blocked with 5% skim milk for 1 hour at room temperature and then incubated with primary antibody overnight at 4 ℃; beta-actin antibodies (1:1000 dilution); COX-2 antibodies (1:2000 dilution). Membranes were then washed with tris buffered saline containing Tween 20 (TBST) and secondary HRP conjugated and incubated for 1 hour at room temperature. The membranes were then visualized using ECL kit.
(3) Experimental results:
LPS-induced macrophage NO release activity inhibiting IC (Low-K) by using rock wool horn cotton 50 4.2 + -1.3 mu M,compounds 1 to 6 did not show significant inhibitory activity under the same conditions, IC 50 IC of positive control dexamethasone with value greater than 50 mu M 50 4.3+/-1.1 mu M, and the effect of the rock wool sheep's horn cotton A is slightly better than that of a positive control medicine.
In addition, the effect diagram of the bergenin on COX-2 protein expression is shown in fig. 3, A is a gel electrophoresis development diagram, B is a histogram, and the concentration of the bergenin gradually increases from left to right, which indicates that the bergenin can obviously inhibit COX-2 protein expression and has concentration dependence.
The foregoing description is only a preferred embodiment of the present application, and the present application is not limited thereto, but it is to be understood that modifications and equivalents of some of the technical features described in the foregoing embodiments may be made by those skilled in the art, although the present application has been described in detail with reference to the foregoing embodiments. Any modification, equivalent replacement, improvement, etc. made within the spirit and principle of the present application should be included in the protection scope of the present application.

Claims (4)

1. The indole alkaloid compound is characterized in that the structural formula of the indole alkaloid compound is shown as a formula I:
formula I.
2. An extraction method of an indole alkaloid compound as defined in claim 1, wherein, the method is characterized in that the rock wool is extracted or leached by reflux in ethanol, the solution after extraction or leaching is suspended by adding water, the solution is extracted by methylene dichloride under an acidic condition, the water layer is extracted by methylene dichloride under an alkaline condition, and the extracted organic layer is separated by column chromatography to obtain the indole alkaloid compound;
the pH of the acidic condition is 3, and the pH of the alkaline condition is 10;
the eluent of the column chromatography is dichloromethane/methanol or petroleum ether/acetone;
the volume ratio of dichloromethane to methanol in the eluent is 100:1-1:1, and the volume ratio of petroleum ether to acetone is 10:1-1:5.
3. The extraction method of the indole alkaloid compound according to claim 2, wherein the column chromatography method is specifically as follows: mixing samples with silica gel, performing 200-300 mesh silica gel column chromatography, dividing into 10 sections, marking as R1-R10 sections, performing R8-Jing Guijiao column chromatography, performing gradient elution by using petroleum ether-acetone as a washing and dehydrating machine in a volume ratio of 10:1-1:5 to obtain 7 sections of R8 a-R8 g, preparing a liquid phase from the R8g sections, and performing MeOH-H in a volume ratio of 73:27 2 O is eluent, and the indole alkaloid compound is separated.
4. Use of an indole alkaloid compound of claim 1 in the preparation of an anti-inflammatory formulation.
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Citations (3)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US2802006A (en) * 1954-06-07 1957-08-06 Ciba Pharm Prod Inc Esters of the yohimbe alkaloids
CN101347475A (en) * 2008-09-05 2009-01-21 中国科学院化学研究所 Use of Alstonia mairei extract in preparing anti-tumor medicament
CN116715703A (en) * 2023-06-02 2023-09-08 山东大学 Method for extracting and purifying total alkaloids of sheep horn cotton

Patent Citations (3)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US2802006A (en) * 1954-06-07 1957-08-06 Ciba Pharm Prod Inc Esters of the yohimbe alkaloids
CN101347475A (en) * 2008-09-05 2009-01-21 中国科学院化学研究所 Use of Alstonia mairei extract in preparing anti-tumor medicament
CN116715703A (en) * 2023-06-02 2023-09-08 山东大学 Method for extracting and purifying total alkaloids of sheep horn cotton

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