CN112159376B - Sesterterpene compound and application thereof in preparing anti-inflammatory drugs - Google Patents

Sesterterpene compound and application thereof in preparing anti-inflammatory drugs Download PDF

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CN112159376B
CN112159376B CN202011013888.4A CN202011013888A CN112159376B CN 112159376 B CN112159376 B CN 112159376B CN 202011013888 A CN202011013888 A CN 202011013888A CN 112159376 B CN112159376 B CN 112159376B
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dichloromethane
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sesterterpene
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于豪冰
林厚文
杨帆
姜文丽
顾斌斌
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Chinese Peoples Liberation Army Naval Characteristic Medical Center
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    • C07D307/00—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom
    • C07D307/02—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom not condensed with other rings
    • C07D307/34—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members
    • C07D307/56—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
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    • A61P29/00—Non-central analgesic, antipyretic or antiinflammatory agents, e.g. antirheumatic agents; Non-steroidal antiinflammatory drugs [NSAID]

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Abstract

The invention relates to the technical field of marine organisms and medicines, in particular to a sesterterpene compound obtained by extraction, separation and purification from marine animal armature sponge Dactylosospongia elegans produced in the sea area near Hsisha Islands, the chemical structure of which is shown as formula (I).

Description

Sesterterpene compound and application thereof in preparing anti-inflammatory drugs
Technical Field
The invention relates to the technical field of marine organisms and medicines, in particular to a novel sesterterpene compound obtained by extraction, separation and purification from marine animal armature sponge Dactylosopongia elegans produced in the sea area near the Xisha Tandong and application thereof in preparing anti-inflammatory drugs.
Background
The sponge is a low and old marine benthonic animal, resists predators or competes resources and living spaces by means of chemical defense, can generate a plurality of secondary metabolites with unique structures and remarkable activities, and is always the research object of marine natural pharmacologists.
The medicinal source material of the present invention is selected from the group consisting of sponges Dactyllospora elegans of the class Demospongiae, subclass Cunningosivia, and order Ceratospongiales(Dictyocetida), sponges of the family Boseudoiidae (Thorectidae), collected in the sea area around the Islands of Western Sand in China. The Dactylospunia sponge contains abundant active secondary metabolites, and alkaloid compounds are separated from the sponge, and chemical components reported in the literature mainly comprise sesquiterpene quinone/hydroquinone, sesquiterpene acids, macrolides, sesterterpenes and other types of compounds. These compounds show significant biological activities such as anticancer, anti-inflammatory, antimalarial and antiviral activities, such as the compounds, which are isolated from Dactyloponia sp, Dactyloponin A, B, D, ent-melemetone B and dysSDamine N, showing strong inhibitory activities against 4 inflammatory cytokines IL-6, IL-1 beta, IL-8 and PEG2 of LPS-induced THP-1 cells, IC50The range of values is 5.1-9.2. mu.M (see, J.Li; F.Yang; Z.Wang; W.Wu; L.Liu; S.P.Wang; B.X.ZHao; W.H.Jiano; S.H.Xu; H.W.Lin, U.NUAL anti-inflammatory polymeric peptides from the marine sponge Dactylosaponia sp.Org.Biomol.Chem.2018,16, (36), 6773-.
Chinese patent document CN102617526A discloses a sesterterpene compound Hippolide J separated from marine animal sponge, its preparation method and application25H36O3The compound shows inhibitory activity to human lung cancer cell A549 and human cervical carcinoma cell Hela, and can be used for preparing antitumor drugs. Chinese patent document CN102617596A discloses a sesterterpene compound Hippolide I separated from marine animal sponge, its preparation method and application, its molecular formula is C24H35NO2The compound has strong pharmacological action, and can be used for resisting tumor, diabetes and obesity.
However, it has not been found that sesterterpenoids C having anti-inflammatory activity are isolated from marine animal armature sponges Dactydospogonis elegans produced in the sea area near the Hsisha Islands26H40O3The report of (1).
Disclosure of Invention
The invention aims to provide a novel sesterterpene compound obtained by extraction, separation and purification from the armature sponge Dactylosoponia elegans, and a preparation method and application thereof.
In order to achieve the purpose, the invention adopts the following technical scheme:
in a first aspect of the present invention, a sesterterpene compound is provided, which has a chemical structure represented by formula (I):
Figure BDA0002698408750000021
furthermore, the sesterterpene compound is a new sesterterpene compound with anti-inflammatory activity, which is obtained by extracting, separating and purifying from marine animal armature sponge Dactylosospongia elegans produced in the sea area near the Xisha island.
In a second aspect of the present invention, there is provided a method for preparing the sesterterpene compounds, which comprises the following steps:
A. preparing a total extract:
pulverizing dried sponge Dactylosopongia elegans, cold-soaking and extracting with 95% ethanol to obtain extractive solution, concentrating the extractive solution until no alcohol smell exists, and extracting with dichloromethane to obtain dichloromethane total extract;
B. separation and purification:
a) preparing a crude extract: suspending the dichloromethane total extract with 90% methanol, extracting with petroleum ether for degreasing, adding water to adjust the methanol concentration of the suspension to 60%, extracting with dichloromethane, and concentrating the extract to obtain dichloromethane crude extract;
b) separation and purification: subjecting the dichloromethane crude extract to reduced pressure liquid column chromatography (VLC), performing gradient elution with petroleum ether and ethyl acetate as solvents, wherein the petroleum ether and ethyl acetate are 50:1, 30:1, 20:1, 10:1, 8:1, 5:1, 3:1, 1:1 and 0:1, developing according to TLC thin layer chromatography, and combining similar fractions to obtain 10 fractions Fr.A-J;
c) subjecting fraction Fr.D to reverse phase column chromatography, gradient eluting with methanol and water at ratio of 1:4, 2:3, 3:2, 4:1, and 1:0, and combining similar fractions by TLC thin layer chromatography to obtain 11 fractions Fr.D 1-D11;
d) subjecting the fraction Fr.D10 to gel column chromatography (Sephadex LH-20), performing gradient elution with methanol and water at ratio of 1:1 as solvent, and performing TLC thin layer chromatography to develop color and combine similar fractions to obtain 3 fractions Fr.D10a-D10 c;
e) and (3) performing silica gel normal phase column chromatography on the component Fr.D10b, and performing gradient elution by using n-hexane and acetone in a ratio of 15:1 as a solvent to obtain the compound.
In a third aspect of the present invention, there is provided a use of the sesterterpene compounds or pharmaceutically acceptable salts thereof as described above, alone or in combination, for the preparation of an anti-inflammatory agent.
Further, the application is the application in preparing a medicament for preventing or treating inflammation.
Further, the inflammation is an inflammatory response mediated by Nitric Oxide (NO).
In a fourth aspect of the present invention, there is provided a use of a sesterterpene compound or a pharmaceutically acceptable salt thereof as described above, alone or in combination, for the manufacture of a medicament for inhibiting Nitric Oxide (NO) release from macrophages.
The invention has the advantages that:
1. in vitro activity tests prove that the compound has a remarkable inhibition effect on the release of Nitric Oxide (NO) by RAW264.7 cells induced by LPS under the action concentration of 10 mu M, and the inhibition rate is 70.47%. The compound of the invention does not show cytotoxicity and inhibition effect on RAW264.7 cells under 10 mu M action concentration tested by a CCK-8 method, and the inhibition rate is 151.23%. The experimental results show that the compound of the invention has significant anti-inflammatory activity, and the anti-inflammatory activity is not realized by inhibiting cell proliferation or toxicity. Therefore, the compound can be used for developing and preparing novel anti-inflammatory drugs for treating inflammatory diseases;
2. the invention provides a new lead compound for researching and developing new anti-inflammatory drugs and provides scientific basis for developing and utilizing marine medicinal resources in China.
Detailed Description
The following examples are provided to illustrate specific embodiments of the present invention.
The armature sponge Dactylospogonis elegans used in the invention is collected from the sea area near the west sand Islands in 2018 in 3 months, is identified by professor Lin Thick Wen, and the sample is stored in a special medical center marine biomedical and polar region medical research room of the second military medical university, and the sample number is YC-3-2018.
Example 1: preparation of the Compounds of the invention
1. Preparing a total extract:
pulverizing dried sponge Dactylosopongia elegans, cold-soaking and extracting with 95% ethanol to obtain extractive solution, concentrating the extractive solution until no alcohol smell exists, and extracting with dichloromethane to obtain dichloromethane total extract;
2. separation and purification:
preparing a crude extract: suspending the dichloromethane total extract with 90% methanol, extracting with petroleum ether for degreasing, adding water to adjust the methanol concentration of the suspension to 60%, extracting with dichloromethane, and concentrating the extract to obtain dichloromethane crude extract;
separating and purifying: subjecting the dichloromethane crude extract to reduced pressure liquid column chromatography (VLC), performing gradient elution with petroleum ether and ethyl acetate as solvents, wherein the petroleum ether and ethyl acetate are 50:1, 30:1, 20:1, 10:1, 8:1, 5:1, 3:1, 1:1 and 0:1, developing according to TLC thin layer chromatography, and combining similar fractions to obtain 10 fractions Fr.A-J;
③ carrying out reverse phase column chromatography on the component Fr.D, carrying out gradient elution by using methanol and water as solvents, wherein the ratio of methanol to water is 1:4, 2:3, 3:2, 4:1 and 1:0, and carrying out Thin Layer Chromatography (TLC) to develop color and combine similar fractions to obtain 11 components Fr.D 1-D11;
fourthly, subjecting the Fr.D10 fraction to gel column chromatography (Sephadex LH-20), performing gradient elution by using methanol and water as a solvent in a ratio of 1:1, and combining similar fractions according to TLC (thin layer chromatography) color development to obtain 3 Fr.D10a-D10 c;
fifthly, performing silica gel normal phase column chromatography on the component Fr.D10b, and performing gradient elution by using n-hexane and acetone in a ratio of 15:1 as solvents to obtain the compound C26H40O3。
3. Structural identification
Compound C of the invention26H40O3Through various modern spectral techniques such as NMR, HRESIMS, IR, UV and the like, the compound C is determined26H40O3The chemical structure of (1).
Compound C of the invention26H40O3: an orange solid;
Figure BDA0002698408750000041
(c 0.20,MeOH)；UV(MeOH)(logε)λmax 201(4.47),258(4.02)；IR(KBr)νmax 3465,2959,2925,2858,1795,1766,1652,1454,1375,1309,1120,959,897,860cm–1；1H and 13C NMR data,see Table 3-3；HRESIMS m/z 418.3308[M+NH4]+(calcd for C26H44NO3,418.3316).1h and3the C NMR data are shown in Table 1.
TABLE 1 Compound C26H40O3Nuclear magnetic resonance spectroscopy data of
Figure BDA0002698408750000051
aMeasured at 600MHz in CDCl3；bMeasured at 150MHz in CDCl3.
Example 2: in vitro anti-inflammatory activity assay of compounds of the invention:
for the compound C of the present invention26H40O3In vitro anti-inflammatory experiments were performed using mouse macrophage RAW264.7 purchased from ATCC under the number TIB-71.
1. Detection of influence of compound on LPS-induced NO release of RAW264.7 cells
The inhibition effect of the compound on LPS-induced mouse macrophage RAW264.7 cell NO release is detected by adopting a Griess method. Making RAW264.7 cells into 5 × 10 cells4A cell suspension of/mL, 100 μ L per well seeded in 96-well plates; after the cells adhered to the surface, LPS (1. mu.g/mL) was added to the LPS group, 10. mu.M of the compound of the present invention was added to the experimental group, 0.1. mu.L of DMSO was added to each well of the blank control group, and after incubation at 37 ℃ for 1 hour, the mixture was addedLPS (1. mu.g/mL) is added, and the culture is continued for 24 h; cell supernatants were harvested, assayed with the NO detection kit, and absorbance values (OD values) at 540nm were recorded for each well. According to the formula Inhibition Rate (IR)% (OD)Sample (I)–ODBlank space)/(ODLPS–ODBlank space) X 100%, the NO production inhibition ratio (IR%) was calculated.
2. Detecting the influence of the compound on the viability of Raw264.7 cells
The toxicity of the compound on Raw264.7 cells is detected by a CCK-8 method. 100 μ L of the supernatant was taken for NO detection, 10 μ L of the prepared CCK-8 solution was added to each of the remaining wells, incubated at 37 ℃ for 1h, and when a significant change occurred, the OD value at 450nm was measured in each well, according to the formula Proliferation Rate (PR)% (OD)%)Sample (I)-ODBlank space)/(ODLPS-ODBlank space) X 100%, the effect on cell proliferation (PR%) was calculated.
3. Results of the experiment
Results of Griess experiments show that the compound has a remarkable inhibition effect on NO release of RAW264.7 cells induced by LPS under the action concentration of 10 mu M, and the inhibition rate (IR%) is 70.47%. The CCK-8 method test result shows that the compound of the invention does not show cytotoxicity and inhibition effect on RAW264.7 cells under the action concentration of 10 mu M, and the cell proliferation rate (PR%) is 151.23%.
4. Conclusion
The compound has obvious inhibition effect on NO release of RAW264.7 cells induced by LPS under the action concentration of 10 mu M, and the effect is not realized through cytotoxic activity, which shows that the compound has anti-inflammatory activity, so the compound can be used as a lead compound of anti-inflammatory drugs.
While the preferred embodiments of the present invention have been described in detail, it will be understood by those skilled in the art that the invention is not limited thereto, and that various changes and modifications may be made without departing from the spirit of the invention, and the scope of the appended claims is to be accorded the full range of equivalents.

Claims (6)

1. A sesterterpene compound has a chemical structure shown in formula (I):
Figure FDA0002698408740000011
2. a process for the preparation of a sesterterpene compound according to claim 1, comprising the steps of:
A. preparing a total extract:
pulverizing dried sponge Dactylosopongia elegans, cold-soaking and extracting with 95% ethanol to obtain extractive solution, concentrating the extractive solution until no alcohol smell exists, and extracting with dichloromethane to obtain dichloromethane total extract;
B. separation and purification:
a) preparing a crude extract: suspending the dichloromethane total extract with 90% methanol, extracting with petroleum ether for degreasing, adding water to adjust the methanol concentration of the suspension to 60%, extracting with dichloromethane, and concentrating the extract to obtain dichloromethane crude extract;
b) separation and purification: subjecting the dichloromethane crude extract to reduced pressure liquid column chromatography, performing gradient elution with petroleum ether and ethyl acetate as solvents, and performing TLC thin layer chromatography to develop color and combine similar fractions to obtain 10 fractions Fr.A-J;
c) subjecting fraction Fr.D to reverse phase column chromatography, gradient eluting with methanol and water at ratio of 1:4, 2:3, 3:2, 4:1, and 1:0, and combining similar fractions by TLC thin layer chromatography to obtain 11 fractions Fr.D 1-D11;
d) subjecting the Fr.D10 fraction to gel column chromatography, performing gradient elution with methanol and water at ratio of 1:1 as solvent, and combining similar fractions according to TLC thin layer chromatography to obtain 3 Fr.D10a-D10 c;
e) and (3) performing silica gel normal phase column chromatography on the component Fr.D10b, and performing gradient elution by using n-hexane and acetone in a ratio of 15:1 as a solvent to obtain the compound.
3. Use of a sesterterpene compound or a pharmaceutically acceptable salt thereof according to claim 1, alone or in combination, for the preparation of an anti-inflammatory agent.
4. The use of sesterterpenoids or pharmaceutically acceptable salts thereof, alone or in combination, according to claim 3, for the preparation of an anti-inflammatory agent, for the prevention or treatment of inflammation.
5. Use of a sesterterpene compound or a pharmaceutically acceptable salt thereof, alone or in combination, as claimed in claim 4, for the manufacture of an anti-inflammatory medicament, wherein the inflammation is a nitric oxide mediated inflammatory response.
6. Use of a sesterterpene compound or a pharmaceutically acceptable salt thereof according to claim 1, alone or in combination, for the manufacture of a medicament for inhibiting nitric oxide release from macrophages.
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CN115197188B (en) * 2021-04-12 2023-12-26 南开大学 Sesquiterpene hydroquinone compound with pentacyclic skeleton and preparation method thereof
CN113563359B (en) * 2021-06-10 2022-06-21 湖南中医药大学 Sesquiterpene dimer compound and preparation method and application thereof
CN115710172B (en) * 2022-09-19 2024-01-30 沈阳药科大学 Diterpenoid compound in euphorbia pekinensis, and extraction method and application thereof
CN115583981B (en) * 2022-10-10 2024-04-12 西北农林科技大学 Eucalyptus alkane type sesquiterpene glycoside compound, erythrina ovalifolia extract containing compound and application of compound

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