CN113264826B - Chain sesquiterpene compound and application thereof in preparation of drugs for preventing or treating inflammatory bowel diseases - Google Patents

Chain sesquiterpene compound and application thereof in preparation of drugs for preventing or treating inflammatory bowel diseases Download PDF

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CN113264826B
CN113264826B CN202110599137.3A CN202110599137A CN113264826B CN 113264826 B CN113264826 B CN 113264826B CN 202110599137 A CN202110599137 A CN 202110599137A CN 113264826 B CN113264826 B CN 113264826B
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inflammatory bowel
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CN113264826A (en
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王超
马骁驰
霍晓奎
李大伟
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    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C59/00—Compounds having carboxyl groups bound to acyclic carbon atoms and containing any of the groups OH, O—metal, —CHO, keto, ether, groups, groups, or groups
    • C07C59/40—Unsaturated compounds
    • C07C59/42—Unsaturated compounds containing hydroxy or O-metal groups
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P1/00—Drugs for disorders of the alimentary tract or the digestive system
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P1/00—Drugs for disorders of the alimentary tract or the digestive system
    • A61P1/04—Drugs for disorders of the alimentary tract or the digestive system for ulcers, gastritis or reflux esophagitis, e.g. antacids, inhibitors of acid secretion, mucosal protectants
    • 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]
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C57/00—Unsaturated compounds having carboxyl groups bound to acyclic carbon atoms
    • C07C57/02—Unsaturated compounds having carboxyl groups bound to acyclic carbon atoms with only carbon-to-carbon double bonds as unsaturation
    • C07C57/13—Dicarboxylic acids
    • Y—GENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
    • Y02—TECHNOLOGIES OR APPLICATIONS FOR MITIGATION OR ADAPTATION AGAINST CLIMATE CHANGE
    • Y02A—TECHNOLOGIES FOR ADAPTATION TO CLIMATE CHANGE
    • Y02A50/00—TECHNOLOGIES FOR ADAPTATION TO CLIMATE CHANGE in human health protection, e.g. against extreme weather
    • Y02A50/30—Against vector-borne diseases, e.g. mosquito-borne, fly-borne, tick-borne or waterborne diseases whose impact is exacerbated by climate change

Abstract

The invention discloses a chain sesquiterpene compound and application thereof in preparing a medicament for preventing or treating inflammatory bowel diseases, belonging to the technical field of biological medicine, wherein the chain sesquiterpene compound has the following structural general formula:
Figure DDA0003092275120000011
or
Figure DDA0003092275120000012
Or
Figure DDA0003092275120000013
Or
Figure DDA0003092275120000014
R 1 Selected from alkyl or carboxyl, R 2 、R 3 Or R 4 Use of chain sesquiterpene compounds selected from hydrogen or hydroxy for preventing or treating diseasesThe medicine for treating inflammatory bowel diseases has obvious anti-inflammatory effect.

Description

Chain sesquiterpene compound and application thereof in preparation of drugs for preventing or treating inflammatory bowel diseases
Technical Field
The invention relates to the technical field of biomedicine, in particular to chain sesquiterpene and application thereof in preparing a medicament for preventing or treating inflammatory bowel diseases.
Background
Inflammatory Bowel Disease (IBD) is an idiopathic inflammatory disease of the intestinal tract involving the ileum, rectum and colon. The clinical manifestations include diarrhea, abdominal pain, bloody stool, etc. The pathological features are mainly classified into Ulcerative Colitis (UC) and Crohn's disease. The disease becomes a common disease of the digestive department gradually and seriously affects the health of people. At present, the disease is mainly treated by medicines. The development of new active ingredients, even drugs, has important social benefits for the treatment of inflammatory bowel disease.
Disclosure of Invention
The invention aims to provide a chain sesquiterpene compound capable of preventing or treating inflammatory bowel diseases and application thereof.
In order to achieve the purpose, the invention provides the following scheme:
the invention provides a chain sesquiterpene compound, the structure of which conforms to the formula I-formula IV, wherein R 1 Selected from alkyl or carboxyl, R 2 、R 3 Or R 4 Are independently selected from the group consisting of hydrogen or hydroxy,
Figure BDA0003092275100000011
Figure BDA0003092275100000021
further, the alkyl is C1-C3 alkyl, preferably methane.
Further, the chain sesquiterpene compound is preferably the following compound:
Figure BDA0003092275100000022
compound 1: r 1 ＝CH 3 ，R 2 ＝OH，R 3 ＝OH，Δ 2,3 ；
Compound 2: r is 1 ＝COOH，R 2 ＝H，R 3 ＝H，R 4 ＝OH；
Compound 3: r 1 ＝COOH，R 3 ＝H，R 4 ＝OH，Δ 10,11 ；
Compound 4: r 1 ＝COOH，R 2 ＝H，R 3 ＝H，R 4 ＝H；
Compound 5: r 1 ＝COOH，R 2 ＝H，R 3 ＝H，Δ 2,3 ；
Compound 6: r 1 ＝COOH，R 3 ＝H，R 4 ＝H，Δ 10,11 ；
Compound 7: r 1 ＝COOH，R 3 ＝H，Δ 2,3 ，Δ 10,11 。
The chain sesquiterpene compound is more preferably compounds 2-3 and 4-6.
The invention also provides a pharmaceutical composition which takes the chain sesquiterpene compound as an active ingredient.
Further, the pharmaceutical composition also comprises pharmaceutically acceptable salts.
Furthermore, the pharmaceutical composition also comprises pharmaceutically acceptable auxiliary materials.
Furthermore, the pharmaceutical composition can be prepared into tablets, capsules, granules or injections.
The invention also provides application of the chain sesquiterpene compound in preparation of a medicament for preventing or treating inflammatory bowel diseases.
The invention also provides application of the pharmaceutical composition in preparing a medicament for preventing or treating inflammatory bowel diseases.
The inflammatory enteritis of the invention can be chronic superficial gastritis, chronic atrophic gastritis, acute and chronic enteritis or colitis, etc.
The invention discloses the following technical effects:
the invention provides chain sesquiterpene and application thereof in preparation of medicines for treating inflammatory bowel diseases, and widens the types of medicines for treating inflammatory bowel diseases.
Drawings
In order to more clearly illustrate the embodiments of the present invention or the technical solutions in the prior art, the drawings needed to be used in the embodiments will be briefly described below, and it is obvious that the drawings in the following description are only some embodiments of the present invention, and it is obvious for those skilled in the art to obtain other drawings without inventive exercise.
FIG. 1 shows a scheme for preparing Compound 1 1 H NMR spectrum;
FIG. 2 is a drawing of Compound 1 13 A C NMR spectrum;
FIG. 3 is an HR-MS profile for Compound 1;
FIG. 4 is a drawing of Compound 2 1 H NMR spectrum;
FIG. 5 is a drawing of Compound 2 13 A C NMR spectrum;
FIG. 6 is an HR-MS profile for Compound 2;
FIG. 7 is a drawing of Compound 3 1 H NMR spectrum;
FIG. 8 is a drawing of Compound 3 13 A C NMR spectrum;
FIG. 9 is a HR-MS profile for Compound 3;
FIG. 10 is a drawing of Compound 4 1 An H NMR spectrum;
FIG. 11 is a drawing of Compound 4 13 A C NMR spectrum;
FIG. 12 is an HR-MS profile for Compound 4;
FIG. 13 is a drawing of Compound 5 1 H NMR spectrum;
FIG. 14 is a drawing of Compound 5 13 A C NMR spectrum;
FIG. 15 is an HR-MS profile for Compound 5;
FIG. 16 is a drawing of Compound 6 1 H NMR spectrum;
FIG. 17 is a drawing of Compound 6 13 A C NMR spectrum;
FIG. 18 is an HR-MS profile for Compound 6;
FIG. 19 is a drawing of Compound 7 1 H NMR spectrum;
FIG. 20 is a photograph of Compound 7 13 A C NMR spectrum;
FIG. 21 is a HR-MS profile for Compound 7;
FIG. 22 is a graph of the therapeutic effect of compounds 4 and 5 on dextran sulfate sodium induced inflammatory bowel disease mice, wherein (1) the body weight of the mice changes; (2) a mouse diarrhea score; (3) extent of rectal bleeding in mice;
FIG. 23 is a graph of the improvement in colon length in inflammatory bowel disease mice by compounds 4 and 5, wherein (1) is the colon length in each group of mice and (2) is the colon length in each group of mice;
FIG. 24 shows the therapeutic effects of compounds 4 and 5 on colon inflammation in mice with inflammatory bowel disease, wherein (1) is the expression of IL-1 in the colon of each group of mice, (2) is the expression of IL-6 in the colon of each group of mice, (3) is the expression of TNF-. alpha.in the colon of each group of mice, and (4) is the expression of INF-. gamma.in the colon of each group of mice.
Detailed Description
Reference will now be made in detail to various exemplary embodiments of the invention, the detailed description should not be construed as limiting the invention but as a more detailed description of certain aspects, features and embodiments of the invention.
It is to be understood that the terminology used herein is for the purpose of describing particular embodiments only and is not intended to be limiting of the invention. Further, for numerical ranges in this disclosure, it is understood that each intervening value, between the upper and lower limit of that range, is also specifically disclosed. Every smaller range between any stated value or intervening value in a stated range and any other stated or intervening value in a stated range is encompassed within the invention. The upper and lower limits of these smaller ranges may independently be included or excluded in the range.
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 to which this invention belongs. Although only preferred methods and materials are described herein, any methods and materials similar or equivalent to those described herein can be used in the practice or testing of the present invention. All documents mentioned in this specification are incorporated by reference herein for the purpose of disclosing and describing the methods and/or materials associated with the documents. In case of conflict with any incorporated document, the present specification will control.
It will be apparent to those skilled in the art that various modifications and variations can be made in the specific embodiments of the present disclosure without departing from the scope or spirit of the disclosure. Other embodiments will be apparent to those skilled in the art from consideration of the specification. The description and examples are intended to be illustrative only.
As used herein, the terms "comprising," "including," "having," "containing," and the like are open-ended terms that mean including, but not limited to.
The fungus Candida albicans of the examples of the present invention was purchased commercially.
EXAMPLE 1 structural characterization of Compounds
The fungus Candida albicans was inoculated under aseptic conditions into potato medium (200g of potato aqueous extract prepared at 1L volume, 20g of glucose), 500 mL/bottle, for a total of 600 bottles. After the fungus culture medium is subjected to constant-temperature shaking culture for 5 days (140r/min) at 32 ℃, the fungus culture medium is extracted by using ethyl acetate (3 times), and ethyl acetate extract is concentrated by a rotary evaporator to obtain the metabolite extract of the fungus Candida albicans. Separating the extract by silica gel column chromatography with petroleum ether-ethyl acetate system as eluent to obtain silica gel column chromatography fraction. The fractions were further purified for chemical composition using preparative liquid chromatography in combination with high performance liquid chromatography. Using 55% methanol- (0.3%, v/v) trifluoroacetic acid aqueous solution as a mobile phase, preparing a liquid phase with the flow rate of 8mL/min and the detection wavelength of 210nm, respectively collecting liquid phase chromatographic peaks, and evaporating the solvent under reduced pressure to obtain solid substances, namely the compounds 1-7 respectively.
EXAMPLE 2 spectroscopic data for Compounds 1-7
Compound 1, colorless oilSubstance like, HR-ESI-MS M/z 293.1721[ M + Na ]] + Calculated value of 293.1723 and molecular formula of C 15 H 26 O 4 。 1 H NMR(CD 3 OD,400MHz)δ H 5.64(d,J＝1.2Hz)，2.20(m)，2.21(m)，5.17(td,J＝6.8,0.8Hz)，2.24(m)，2.01(m)，1.70(m)，1.33(m)，3.22(dd,J＝10.4,1.6Hz)，1.15(s)，2.13(d,J＝1.2Hz)，1.63(d,J＝0.8Hz)，1.12(s)。 13 C NMR(CD 3 OD,100MHz)δ C 170.2，117.0，161.2，41.9，27.0，124.4，137.3，37.9，30.8，79.0，73.8，25.6，18.9，16.2，24.9。
Compound 2, a colorless oily substance, HR-ESI-MS M/z 285.1704[ M-H] - Calculated value of 285.1707, molecular formula of C 15 H 26 O 5 。 1 H NMR(CD 3 OD,400MHz)δ H 2.46(s)，1.55(m)，2.08(m)，5.13(t,J＝7.2Hz)，1.98(t,J＝7.2Hz)，1.41(m)，1.57(m)，1.35(m)，2.39(m)，1.27(s)，1.60(s)，1.12(d,J＝6.8Hz)。 13 C NMR(CD 3 OD,100MHz)δ C 175.4，46.4，72.1，42.8，23.5，125.7，135.9，40.6，26.5，34.5，40.5，180.7，27.1，15.8，17.6。
Compound 3, a colorless oily substance, HR-ESI-MS M/z 283.1548[ M-H] - Calculated value of 283.1551 and molecular formula of C 15 H 24 O 5 。 1 H NMR(CD 3 OD,400MHz)δ H 2.45(s)，1.57(m)，2.30(m)，5.17(t,J＝7.2Hz)，2.11(t,J＝7.2Hz)，2.08(m)，6.71(td,J＝7.2,1.2Hz)，1.27(s)，1.64(s)，1.79(d,J＝1.2Hz)。 13 C NMR(CD 3 OD,100MHz)δ C 175.3，46.3，72.1，42.7，23.5，126.4，135.2，39.3，28.2，143.6，128.9，171.6，27.1，15.9，12.4。
Compound 4, a colorless oily substance, HR-ESI-MS M/z 269.1755[ M-H] - Calculated value of 269.1758 and molecular formula of C 15 H 26 O 4 。 1 H NMR(CD 3 OD,600MHz)δ H 2.29(dd,J＝14.4,6.0Hz)，2.07(dd,J＝14.4,8.0Hz)，1.92(m)，1.40(m)，1.23(m)，2.02(m)，5.12(t,J＝6.6Hz)，1.99(t,J＝6.6Hz)，1.42(m)，1.58(m)，1.36(m)，2.39(m)，0.95(d,J＝6.6Hz)，1.59(s)，1.12(d,J＝7.2Hz)。 13 C NMR(CD 3 OD,150MHz)δ C 177.1，42.6，31.1，37.8，26.3，125.7，135.9，40.5，26.5，34.4，40.5，180.8，20.0，15.8，17.6。
Compound 5, a colorless oily substance, HR-ESI-MS M/z 267.1599[ M-H] - Calculated value of 267.1602, molecular formula of C 15 H 24 O 4 。 1 H NMR(DMSO-d 6 ,600MHz)δ H 5.64(s)，2.19(m)，2.19(m)，5.12(d,J＝6.6Hz)，1.99(t,J＝6.6Hz)，1.42(m)，1.56(m)，1.36(m)，2.39(m)，2.13(s)，1.60(s)，1.12(d,J＝6.6Hz)。 13 C NMR(DMSO-d 6 ,150MHz)δ C 170.2，117.0，161.2，41.9，27.0，124.5，136.9，40.6，26.5，34.4，40.5，180.8，18.9，15.9，17.6。
Compound 6, a colorless oily substance, HR-ESI-MS M/z 267.1611[ M-H] - Calculated value of 267.1602 and molecular formula of C 15 H 24 O 4 。 1 H NMR(DMSO-d 6 ,600MHz)δ H 2.21(m)，2.00(m)，1.82(m)，1.23(m)，1.30(m)，1.16(m)，1.96(m)，5.11(t,J＝6.6Hz)，2.24(m)，2.05(t,J＝7.8Hz)，2.24(m)，6.61(t,J＝6.6Hz)，0.88(d,J＝6.6Hz)，1.58(s)，1.72(s)。 13 C NMR(DMSO-d 6 ,150MHz)δ C 1174.0，41.2，29.4，36.1，24.9，124.8，133.8，37.8，26.7，141.1，127.8，168.9，19.5，15.7，12.3。
Compound 7, a colorless oily substance, HR-ESI-MS M/z 265.1441[ M-H] - Calculated value of 265.1445 and molecular formula of C 15 H 22 O 4 。 1 H NMR(CD 3 OD,600MHz)δ H 5.58(s)，2.11(m)，2.11(m)，5.11(br s)，2.05(t,J＝7.2Hz)，2.22(dd,J＝14.4,7.2Hz)，6.61(t,J＝6.6Hz)，2.07(s)，1.59(s)，1.72(s)。 13 C NMR(CD 3 OD,150MHz)δ C 167.5，116.2，158.3，40.0，25.5，123.6，134.7，37.7，26.8，141.1，127.8，168.9，18.2，15.8，12.3。
EXAMPLE 3 evaluation of anti-inflammatory action of Compounds 1-7
Mouse macrophage RAW264.7 was seeded at 4 × 105 in 96-well plates and cultured overnight. The culture medium comprises DMEM culture solution containing 10% fetal calf serum, 50U/mL penicillin and streptomycin. Thereafter, LPS was added at a concentration of 5. mu.g/mL for 2 hours, and then compounds 1 to 7 (0.1. mu.M) were added, respectively, and after 12 hours, the levels of inflammatory factors IL-1. beta. and IL-6 were measured by ELISA kits, respectively.
TABLE 1 protective Effect of Compounds 1-7 on LPS-induced cellular inflammation
Figure BDA0003092275100000071
According to the content of the inflammatory factors IL-1 beta and IL-6 in the table 1, the compounds 1-7 can effectively relieve the cell inflammation induced by LPS, and have significant difference compared with a control group.
Example 4 evaluation of therapeutic Effect of inflammatory bowel disease
C57BL/6J male mice were bred for 6-8 weeks, after 1 week of acclimatization, and randomized into four groups (inflammatory bowel disease model control group, compound 4-treated group, compound 5-treated group, obeticholic acid control group) of 6 mice each. In the first week, the compounds 4 and 5 and obeticholic acid were prepared into hydroxymethylcyclodextrin solutions, and the solutions were gavaged to mice at a dose of 5 mg/kg. One week after dosing, dextran sodium sulfate was formulated into a 2.5% aqueous solution and placed in the four groups of mouse drinking bottles described above to initiate inflammatory bowel disease molding. The body weight of the mice was recorded daily and observed for activity, diarrhea, bloody stool, and rectal bleeding. Compared with the mice of inflammatory bowel disease molding group, the compounds 4 and 5 can improve the health state of the mice, relieve the weight reduction trend, improve diarrhea and reduce colorectal hemorrhage (figure 22). When the model is made for 8 days, the diarrhea and the hematochezia of the mice are serious, and the weight is obviously reduced. After 4 groups of mice were sacrificed, the colons were intercepted and photographed on a piece of coordinate paper to count the length of the colons. As shown in fig. 23, compounds 4 and 5 were able to protect the colon of mice, which is substantially the same length as the positive control drug obeticholic acid-treated group.
Taking fresh colon tissue, storing at-80 ℃, taking part of tissue sample, extracting RNA by a tissue grinder, performing reverse transcription, and measuring the expression conditions of inflammatory factors such as IL-1 beta, IL-6, TNF-alpha, INF-gamma and the like by using an RT-PCR technology to evaluate the inflammatory reaction condition of the intestinal tract of the mouse. As shown in figure 24, compounds 4 and 5, when administered to mice, had a significant relief of colonic inflammation, similar to that of the positive drug obeticholic acid treated mice.
The above-described embodiments are merely illustrative of the preferred embodiments of the present invention, and do not limit the scope of the present invention, and various modifications and improvements of the technical solutions of the present invention can be made by those skilled in the art without departing from the spirit of the present invention, and the technical solutions of the present invention are within the scope of the present invention defined by the claims.

Claims (6)

1. A pharmaceutical composition is characterized in that chain sesquiterpene compounds are used as active ingredients, and the structure of the chain sesquiterpene compounds conforms to the formula I-formula IV, wherein R 1 Selected from methyl or carboxyl, R 2 、R 3 Or R 4 Are independently selected from the group consisting of hydrogen or hydroxy,
Figure FDA0003596196500000011
2. the pharmaceutical composition of claim 1, further comprising a pharmaceutically acceptable salt.
3. The pharmaceutical composition of claim 1, further comprising a pharmaceutically acceptable excipient.
4. The pharmaceutical composition according to claim 1, which is prepared into tablets, capsules, granules or injections.
5. Use of the chain sesquiterpene compound of claim 1 in the preparation of a medicament for the prevention or treatment of inflammatory bowel disease.
6. Use of the pharmaceutical composition of claim 1 for the preparation of a medicament for the prevention or treatment of inflammatory bowel disease.
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Citations (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
GB1501885A (en) * 1974-10-31 1978-02-22 Hoffmann La Roche Process for the manufacture of carboxylic acids
JPS6396149A (en) * 1986-10-13 1988-04-27 Kuraray Co Ltd Novel terpene compound and anti-inflammatory agent containing the same

Patent Citations (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
GB1501885A (en) * 1974-10-31 1978-02-22 Hoffmann La Roche Process for the manufacture of carboxylic acids
JPS6396149A (en) * 1986-10-13 1988-04-27 Kuraray Co Ltd Novel terpene compound and anti-inflammatory agent containing the same

Non-Patent Citations (4)

* Cited by examiner, † Cited by third party
Title
《Isopentenoid synthesis in isolated embryonic Drosophila cells. Farnesol catabolism and ω-oxidation》;Dolores Gonzalez-Pacanowska等;《Journal of Biological Chemistry》;19881231;第263卷(第3期);第1301-1306页 *
《Metabolism of the juvenile hormone analog methyl farnesoate 10,11-epoxide in two insect species》;A.F.White;《Life Sciences》;19720222;第11卷(第4期);第201-210页 *
《Oxidation of acyclic terpenoids by Corynebacterium sp》;YASUHIRO YAMADA等;《Applied and Environmental Microbiology》;19850401;第49卷(第4期);第960-963页 *
《Two new compounds from a marine-derived Streptomyces sp》;Si-Yu Zhou等;《Journal of Asian Natural Products Research》;20170401;第19卷(第12期);第1172-1176页 *

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