CN115385924B - Cyclopentane benzofuran compound with anti-tumor activity and application thereof - Google Patents
Cyclopentane benzofuran compound with anti-tumor activity and application thereof Download PDFInfo
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Abstract
The invention discloses a cyclopentane benzofuran compound with anti-tumor activity and application thereof, wherein the compound is obtained by separating and extracting from Malus asiatica (Aglaia testicularis C.Y.wu) for the first time, and the structural formula of the compound is shown as formula (1). The preparation method comprises the steps of methanol extraction, alcohol recovery concentration, silica gel column chromatography, gradient elution, reversed phase column chromatography and the like, and the compound has remarkable anti-tumor activity, shows high-strength cytotoxicity on human leukemia HEL cell strains, human leukemia K562 cell strains and human colon cancer HCT116 cell strains, can be developed and applied in preparing medicaments for treating tumors, and provides a new medicament and a new path for comprehensive utilization of Malus asiatica plants in the aspects of preventing and treating cancer development.
Description
Technical Field
The invention belongs to the field of natural medicines, and particularly relates to a cyclopentane benzofuran compound with anti-tumor activity and application thereof.
Background
The cyclopentanecenzofurans are characteristic secondary metabolites of the genus milano (Aglaia), isolated only from this genus, and the other two structurally related compounds cyclopentane benzopyran and benzoxopyran are collectively referred to as "xanthones". Of the "xanthosines", many cyclopentane benzofuran compounds show significant biological activity at nanomolar concentrations, whereas benzoxopyran and cyclopentane benzopyran do not show antiproliferative activity on cancer cell lines, indicating that the cyclopentane benzofuran core is the fundamental unit of such biological activity. And reported data show that cyclopentane benzofurans are active against NF- κB and NF-AT in T lymphocytes by inhibiting protein or DNA synthesis in certain cancer cells. In addition, the cyclopentane benzofuran compounds can also block the cell cycle process in the G2/M transition phase and induce cancer cell lines to undergo apoptosis. Therefore, cyclopentane benzofuran compounds have excellent potential as candidate therapeutic agents against tumors.
The plant resources of China are rich, medicinal plants play an important role as the magnificent of China, and in recent years, due to the characteristics of high efficiency, low toxicity, diversified chemical components, rich resources and the like, the search of antitumor therapeutic agents from the medicinal plants gradually becomes a research hotspot, and various active components for treating tumors are discovered from the medicinal plants. Ma Shenguo it is a tree of the genus Mizalanum (Aglaia) of the family Meliaceae. Is mainly distributed in southeast Asia countries and regions in the south of China. Has effects of promoting blood circulation, dispelling blood stasis, relieving swelling and pain, activating qi-flowing, and resolving stagnation. Can be used for treating rheumatic arthralgia, traumatic injury, carbuncle, and toxic swelling. Modern pharmacology shows that the plant extract has various activities such as anti-tumor, insecticidal, antibacterial, antiviral and the like. The chemical composition research of Ma Shenguo shows that the main chemical composition of the compound comprises cyclopentane benzofuran, bisamide, lignin, triterpene, steroid, flavone, tetranortriterpene and other structural types, and the compound has the diversity of structural types. And the plant is rich in natural cyclopentane benzofuran compounds, and is one of research hotspots of active natural products at present.
Disclosure of Invention
The invention aims to provide the cyclopentane benzofuran compound with anti-tumor activity, and the preparation method of the compound is simple and feasible, raw materials are easy to obtain, and the compound can be applied to preparation of drugs for inhibiting human leukemia HEL cell strain, human leukemia K562 cell strain and human colon cancer HCT116 cell strain.
The aim and the main technical problems are achieved by adopting the following technical scheme: the cyclopentane benzofuran compound with anti-tumor activity is obtained by first separating and extracting from the horsetail fruits, and has a structural formula of (1):
the preparation method of the compound comprises the following steps:
(1) Taking 50 parts of the branches and leaves of the malus asiatica, crushing, adopting 200 parts of 95% industrial methanol, leaching for 3-5 times at room temperature for 4 days each time, recovering methanol and concentrating to obtain 10 parts of extract;
(2) Subjecting the crude extract to silica gel column chromatography, performing gradient elution by using an eluent with the volume ratio of petroleum ether to acetone being 9:1-1:1, detecting different elution fractions by using a silica gel thin layer chromatography technology according to 100 parts of each gradient, combining fractions with the same thin layer chromatography result, and obtaining seven fractions according to the thin layer chromatography expression: fr.1, fr.2, fr.3, fr.4, fr.5, fr.6, fr.7;
(3) Performing reverse phase column chromatography on Fr.6, performing gradient elution by using an eluent with the volume ratio of methanol to water of 1:1-9:1, combining according to the thin layer chromatography performance, and dividing into 9 subfractions: fr.6a, fr.6b, fr.6c, fr.6d, fr.6e, fr.6f, fr.6g, fr.6h, and fr.6i; and performing silica gel column chromatography on Fr.6e, and performing gradient elution on the eluent with the volume ratio of petroleum ether to ethyl acetate of 1:9-1:20 to obtain the compound 1.
The application of the compound in preparing drugs for inhibiting human leukemia HEL cell strain, human leukemia K562 cell strain and human colon cancer HCT116 cell strain.
When the compound is used as a medicament, the compound can be directly used or used in the form of a pharmaceutical composition, wherein the pharmaceutical composition contains 0.1-99% of the compound, and the rest is a medicinal carrier or excipient.
The pharmaceutically acceptable carriers or excipients are one or more solid, semi-solid and liquid diluents, fillers and pharmaceutical formulation adjuvants.
The pharmaceutical composition is used in the form of a unit weight dosage.
The dosage form of the pharmaceutical composition is as follows: injection, suspension, emulsion, solution, syrup, tablet, capsule, granule, spray and aerosol.
The therapeutic administration route of the pharmaceutical composition comprises the following steps: intravenous injection, intravenous drip, intramuscular injection, intraperitoneal injection, subcutaneous injection, oral administration, sublingual administration, and mucosal dialysis.
Compared with the prior art, the method has the advantages that the dried branches and leaves of the equi-kidney fruits are subjected to methanol extraction, extract concentration, silica gel column chromatography and thin layer chromatography, the extraction and separation process is simple, and the raw materials are abundant and can be obtained in a large amount. The MTT method is adopted to test the in vitro anti-tumor effect of cyclopentane benzofuran compounds separated from the branches and leaves of the Malus asiatica on the human leukemia HEL cell strain, and the test result shows that the compounds have remarkable cytotoxicity on the human leukemia HEL cell strain in vitro and IC thereof 50 The value is 0.12+/-0.04 mu M; test the in vitro anti-tumor effect of the compound separated from the fruit branches and leaves of the Malus asiatica on the human leukemia K562 cell strain, and the test result shows that the compound has obvious cytotoxicity on the human leukemia K562 cell strain in vitro and IC thereof 50 The value is 0.12+/-0.01 mu M; test the in vitro anti-tumor effect of the compound separated from the fruit branches and leaves of the Malus asiatica on the human colon cancer HCT116 cell strain, and test results show that the compound has obvious cytotoxicity on the human colon cancer HCT116 cell strain in vitro and IC thereof 50 The value is 0.09+/-0.04 mu M; therefore, the cyclopentane benzofuran compounds separated from the branches and leaves of the malus asiatica have in-vitro anti-tumor activity, so that the cyclopentane benzofuran compounds have the potential of preparing tumor prevention and treatment medicaments, and the cyclopentane benzofuran compounds have the potential of preparing tumor prevention and treatment medicamentsThe obtained compound provides a basis for developing a novel anti-tumor medicament with high efficiency and low toxicity.
Drawings
FIG. 1 is a structural diagram of cyclopentane benzofuran compound 1 with antitumor activity.
FIG. 2 shows that cyclopentane benzofuran type 1 has antitumor activity 1 HNMR spectra.
FIG. 3 Cyclopentane benzofuran type Compound 1 with antitumor Activity 13 CNMR spectra.
Detailed Description
The following describes in detail specific embodiments of a cyclopentane benzofuran compound, its preparation method and application according to the present invention with reference to preferred examples and experimental examples.
Example 1
A preparation method of cyclopentane benzofuran compounds with antitumor activity comprises the following steps:
(1) Taking 50 parts of dried branches and leaves of the synephrine, crushing, adopting 200 parts of 95% industrial methanol, leaching for 3-5 times at room temperature for 4 days each time, recovering alcohol and concentrating to obtain 10 parts of extract;
(2) Subjecting the crude extract to silica gel column chromatography, performing gradient elution by using an eluent with the volume ratio of petroleum ether to acetone being 9:1-1:1, detecting different elution fractions by using a silica gel thin layer chromatography technology according to 100 parts of each gradient, combining fractions with the same thin layer chromatography result, and obtaining seven fractions according to the thin layer chromatography expression: fr.1, fr.2, fr.3, fr.4, fr.5, fr.6, fr.7;
(3) Fr.6 (90 g) was subjected to reverse phase column chromatography using gradient elution with an eluent in a volume ratio of methanol to water of 1:1 to 9:1, each gradient being 25L. Detecting different elution fractions by using silica gel thin layer chromatography, combining fractions with the same thin layer chromatography result, and combining the fractions according to the thin layer chromatography display result to obtain 9 subfractions: fr.6a (1 g), fr.6b (2 g), fr.6c (8 g), fr.6d (21 g), fr.6e (14 g), fr.6f (6 g), fr.6g (6 g), fr.6h (14 g) and fr.6i (2 g); and performing silica gel column chromatography on Fr.6e, and performing gradient elution on the eluent with the volume ratio of petroleum ether to ethyl acetate of 1:9-1:20 to obtain the compound 1.
Structural identification of the compound:
the compound passes through high resolution mass spectrum and nuclear magnetic resonance spectrum 1 HNMR, 13 CNMR, 2D-NMR), ultraviolet spectrum, infrared spectrum, optical rotation, etc., to determine the structural formula of compound 1, as follows:
compound 1: colorless crystals with molecular formula C 31 H 30 O 7 N 2 ，(c2.95MeOH)；UV(MeOH)λ max 206nm；IR(KBr)ν max 3402.32,2929,2851,1622,1599,1453,1428,1218,1200,1147,1120；positiveHR-ESI-MS:m/z565.1945[M+Na] + (calcdfor C 31 H 30 O 7 N 2 Na,565.5880)； 1 HNMR(600MHz,CD 3 OD)δ:7.10(2H,t,J＝10.9Hz,H-3”,5”),7.00(2H,t,J＝15.1Hz,H-2”,6”),6.93(1H,t,J＝14.94Hz,H-4”),6.77(1H,m,H-2'),6.73(1H,m,H-6'),6.55(1H,d,J＝8.6Hz,H-5'),6.33(1H,d,J＝1.9Hz,H-5),6.17(1H,d,J＝1.7Hz,H-7),5.23(1H,t,J＝11.9Hz,H-5”'),4.31(1H,d,J＝5.3Hz,H-3),3.85(3H,d,J＝2.0Hz,OCH 3 -8),3.82(3H,d,J＝2.0Hz,OCH 3 -6),3.68(3H,d,J＝1.6Hz,OCH 3 -4'),3.58(1H,m,H-2”'α),3.41(1H,m,H-2”'β),2.51(1H,s,H-4”'β),2.22(1H,s,H-4”'α),2.04(2H,s,H-3”')。 13 CNMR(150MHz,CD 3 OD)δ:24.0(C-3”'),32.9(C-4”'),45.3(C-2”'),55.8(OCH 3 -8),56.1(OCH 3 -4'),56.2(OCH 3 -6),58.4(C-3),72.0(C-5”'),88.7(C-8b),90.2(C-5),93.4(C-7),103.3(C-2),106.5(C-3a),109.0(C-8a),111.0(C-5'),116.1(C-2'),120.1(C-6'),126.8(C-4”),128.1(C-2”,6”),129.8(C-3”,5”),130.2(C-1'),140.6(C-1”),145.7(C-3'),147.6(4'),159.4(C-8),162.1(C-4a),162.4(C-1),165.39(C-1”'),165.44(C-6). Compound 1 1 HNMR, 13 The CNMR spectra are shown in FIGS. 2 and 3.
In order to further analyze the toxic effect of compound 1 on human leukemia HEL cell line, human leukemia K562 cell line and human colon cancer HCT116 cell line, and better for preparing antitumor drugs, the following experiment was performed on compound 1 obtained in example 1:
(1) Experimental materials
96-well culture plate, 1640 culture solution, fetal bovine serum, 0.25% pancreatin, tetramethyl azoazole blue (3- (4, 5-dimethyl 1-thiozol-2-yl-tetrazolium bromide; MTT), dimethyl sulfoxide (DMSO), centrifuge, biological microscope and enzyme marker instrument.
(2) Test method
Rapidly thawing tumor cells in the frozen tube in a water bath at 37deg.C, centrifuging to collect cells, and collecting cells with a buffer containing antibiotic (100 IUmL) -1 Penicillin and 100IUmL -1 Streptomycin) and 10% fetal bovine serum 1640 complete medium at 37 ℃,5% co 2 Culturing in incubator with constant temperature and saturated humidity. When the cells are mostly pooled, passaging is performed, and the cells in the logarithmic growth phase are selected for experiments. Transferring the cells into a centrifuge tube, centrifuging at 800r/min for 3min, removing supernatant, adding new culture solution, inoculating tumor cells into 96-well plate (regulating cell concentration of human leukemia HEL cells and human leukemia K562 cells to 1×10) 4 Density of individual/ml; human colon carcinoma HCT116 cells regulate cell concentration to 7×10 3 Density per ml), 100 μl of cell fluid was added to each well, and adherent cells were inoculated 12 hours earlier. At 37 ℃,5% CO 2 Culturing for 4 hr, adding compound 1 (fixed concentration 20 μm primary sieve, 5 concentrations of compound with tumor cell growth inhibition rate around 50% at this concentration into gradient multiple sieve), 37 deg.C, 5% CO 2 After 72 hours of conditioning, 10. Mu.LMTT (5 g/L) was added to each well and culture was continued. 100 μl of the triple solution was added overnight for incubation at 570nm using an enzyme-labeled instrumentMeasuring an absorption value; DMSO group was used as a blank control, doxorubicin as positive control, and each experiment was repeated three times.
(3) Test results:
the cytotoxic effects of cyclopentane benzofuran compounds on three human tumor cell lines are shown in the following table:
the results show that the compound 1 shows high-intensity cytotoxicity on partial human tumor cell lines in vitro. Cytotoxic Activity of Compound 1 on human leukemia HEL cell lines (IC 50 0.12.+ -. 0.04) on human leukemia K562 cell line (IC 50 0.12.+ -. 0.01) and cytotoxic activity (IC) against human colon carcinoma HCT116 cell line 50 0.09+ -0.04) is stronger than the cytotoxic activity (IC) of the positive control doxorubicin on the human leukemia HEL cell line 50 0.14.+ -. 0.03) on human leukemia K562 cell line (IC 50 0.65.+ -. 0.08) and cytotoxic activity (IC) against human colon carcinoma HCT116 cell line 50 0.20±0.13). The test results prove that the compound has good in-vitro anti-tumor bioactivity, and provides a new medicament and a new way for the comprehensive utilization of the synephrine horseradish plant and the development of medicaments for preventing and treating cancers.
The foregoing description is only a preferred embodiment of the present invention, and is not intended to limit the invention in any way, and any simple modification, equivalent variation and variation of the above embodiment according to the technical matter of the present invention still fall within the scope of the technical scheme of the present invention.
Claims (8)
1. A cyclopentane benzofuran compound having a structural formula of (1):
2. a process for the preparation of a cyclopentane benzofuran compound according to claim 1 comprising the steps of:
(1) Taking 50 parts of the branches and leaves of the malus asiatica, crushing, adopting 200 parts of 95% industrial methanol, leaching for 3-5 times at room temperature for 4 days each time, recovering methanol and concentrating to obtain 10 parts of extract;
(2) Subjecting the crude extract to silica gel column chromatography, performing gradient elution by using an eluent with the volume ratio of petroleum ether to acetone being 9:1-1:1, detecting different elution fractions by using a silica gel thin layer chromatography technology according to 100 parts of each gradient, combining fractions with the same thin layer chromatography result, and obtaining seven fractions according to the thin layer chromatography expression: fr.1, fr.2, fr.3, fr.4, fr.5, fr.6, fr.7;
(3) Performing reverse phase column chromatography on Fr.6, performing gradient elution by using an eluent with the volume ratio of methanol to water of 1:1-9:1, combining according to the thin layer chromatography performance, and dividing into 9 subfractions: fr.6a, fr.6b, fr.6c, fr.6d, fr.6e, fr.6f, fr.6g, fr.6h, and fr.6i; and performing silica gel column chromatography on Fr.6e, and performing gradient elution on the eluent with the volume ratio of petroleum ether to ethyl acetate of 1:9-1:20 to obtain the compound 1.
3. The use of a cyclopentane benzofuran compound according to claim 1 in the preparation of a medicament for the inhibition of human leukemia HEL cell line, human leukemia K562 cell line and human colon cancer HCT116 cell line.
4. Use of a cyclopentane benzofuran compound according to claim 3, wherein the compound is for use as a medicament, either directly or in the form of a pharmaceutical composition comprising 0.1 to 99% of the compound, the remainder being a pharmaceutically acceptable carrier or excipient.
5. The use of cyclopentane benzofuran compounds according to claim 4, wherein the pharmaceutically acceptable carrier or excipient is one or more of solid, semi-solid and liquid diluents, fillers and pharmaceutical adjuvants.
6. The use of cyclopentane benzofuran compounds according to claim 4, wherein the pharmaceutical composition is in the form of a unit weight dose.
7. The use of cyclopentane benzofuran compounds according to claim 4, wherein the pharmaceutical composition is in the form of: injection, suspension, emulsion, solution, syrup, tablet, capsule, granule, spray and aerosol.
8. The use of cyclopentane benzofuran compounds according to claim 4, wherein the pharmaceutical composition is administered by the therapeutic route: intravenous injection, intravenous drip, intramuscular injection, intraperitoneal injection, subcutaneous injection, oral administration, sublingual administration, and mucosal dialysis.
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Citations (8)
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| JPH0967376A (en) * | 1995-09-05 | 1997-03-11 | Terumo Corp | Suppressant for cancer gene function |
| JPH0967375A (en) * | 1995-08-28 | 1997-03-11 | Terumo Corp | Suppressant for cancer gene function |
| WO2004041812A1 (en) * | 2002-11-08 | 2004-05-21 | The Government Of The State Of Sarawak, Malaysia | Therapeutic compounds and methods |
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2022
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| AU2001268848B2 (en) * | 2000-07-05 | 2005-12-15 | The Government Of The State Of Sarawak, Malaysia | Therapeutic compounds and methods |
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