CN115385924A - Cyclopentanepenzofuran compound with anti-tumor activity and application thereof - Google Patents
Cyclopentanepenzofuran 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 horse kidney fruits (Agaia testicularis C.Y.Wu) for the first time, and the structural formula of the compound is shown as a formula (1). The preparation method comprises the steps of methanol extraction, alcohol recovery and concentration, silica gel column chromatography, gradient elution, reversed phase column chromatography and the like, the compound has obvious antitumor activity, shows higher-strength cytotoxic effect on human leukemia HEL cell strains, human leukemia K562 cell strains and human colon cancer HCT116 cell strains, can be developed and applied in the preparation of medicaments for treating tumors, and provides a new medicament and a new way for the comprehensive utilization of Malus asiatica plants in the development of medicaments for preventing and treating cancers.
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
Cyclopentane benzofuran compounds are characteristic secondary metabolites of the genus aglaria, isolated only from this genus, and the other two structurally related compounds cyclopentane benzopyran and benzoxapyran are collectively referred to as "xanthosides". Among the "xanthosine" class of compounds, many of the cyclopentane benzofuran classes exhibit significant biological activity at nanomolar concentrations, whereas the benzoxapyrans and cyclopentane benzopyrans do not exhibit antiproliferative activity against cancer cell lines, suggesting that the cyclopentane benzofuran nucleus is the basic unit of the above biological activity. And reported data show that the cyclopentanofuran compounds inhibit protein or DNA synthesis in certain cancer cells and have activity against NF-. Kappa.B and NF-. Kappa.AT in T lymphocytes. In addition, the compound of the cyclopentane benzofuran class can block the cell cycle process in the G2/M transition phase and induce the cancer cell line to be apoptotic. Therefore, the compound of the cyclopentane benzofuran class has excellent potential as a candidate therapeutic agent for resisting tumors.
The Chinese plant resource is rich, the medicinal plant has been used as the treasure in China to play an important role all the time, in recent years, due to the characteristics of high efficiency, low toxicity, diversified chemical components, rich resources and the like, the search of the anti-tumor therapeutic agent from medicinal plants gradually becomes a research hotspot, and various active ingredients with the function of treating tumors are found from the research hotspot. Mallotus philippinensis (Meliaceae) Saylaria (Aglaia) arbor. Mainly distributed in southeast Asia countries and south China. Has effects in treating cough, dizziness, fever, asthma, and dermatitis, promoting blood circulation, dispelling blood stasis, relieving swelling and pain, promoting qi circulation, and relieving depression. Can be used for treating rheumatic arthralgia, traumatic injury, superficial infection, and toxic swelling. Modern pharmacology indicates that the plant extract has various activities of resisting tumor, killing insects, resisting bacteria, resisting viruses and the like. The chemical composition research of the horsekidney fruit shows that the major chemical compositions of the horsekidney fruit comprise various structural types such as cyclopentane benzofuran, bisamide, lignin, triterpene, steroid, flavone, tetranortriterpene and the like, and the horsekidney fruit shows diversity of the structural types. The plants are rich in natural cyclopentane benzofuran compounds, and the natural cyclopentane benzofuran compounds are one of the research hotspots of active natural products.
Disclosure of Invention
The invention aims to provide the cyclopentane benzofuran compound with anti-tumor activity, the preparation method of the compound is simple and easy to implement, 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 purpose of the invention and the main technical problem of solving the invention are realized by adopting the following technical scheme: the compound is obtained by separating and extracting from horse kidney fruits for the first time, and has a structural formula shown as a formula (1):
the preparation method of the compound comprises the following steps:
(1) Taking 50 parts of Malus asiatica branches and leaves, crushing, leaching for 3-5 times at room temperature by adopting 200 parts of 95% industrial methanol, each time for 4 days, recovering methanol, and concentrating to obtain 10 parts of extract;
(2) Performing silica gel column chromatography on the crude extract, performing gradient elution by using an eluent with the volume ratio of petroleum ether to acetone being 9-1, wherein the eluent is prepared from the following raw materials in a ratio of 1-1, each gradient is 100 parts, detecting different elution fractions by using a silica gel thin-layer chromatography technology, merging fractions with the same thin-layer chromatography result, and performing thin-layer chromatography to obtain seven fractions: 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 being 1-9, combining according to the thin-layer chromatography performance, and dividing into 9 sub-fractions: 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 the Fr.6e, and performing gradient elution by using an eluent with the volume ratio of petroleum ether to ethyl acetate being 1.
The compound is applied to the preparation of human leukemia HEL cell strain, human leukemia K562 cell strain and human colon cancer HCT116 cell strain inhibiting drugs.
When used as a medicament, the compounds may be used as such 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.
The pharmaceutically acceptable carrier or excipient is one or more of solid, semi-solid and liquid diluents, fillers and pharmaceutical adjuvants.
The pharmaceutical composition is used in the form of a dosage per unit body weight.
The dosage form of the pharmaceutical composition comprises: injection, suspension, emulsion, solution, syrup, tablet, capsule, granule, spray, and aerosol.
The therapeutic administration routes of the pharmaceutical composition are as follows: 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 horse 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 large quantity. The MTT method is adopted to test the in vitro anti-tumor effect of the cyclopentane benzofuran compound separated from the branches and leaves of the equine kidney on the human leukemia HEL cell strain, and the test result shows that the compound has significant cytotoxic effect on the human leukemia HEL cell strain in vitro and IC thereof 50 The value was 0.12. + -. 0.04. Mu.M; the in vitro anti-tumor effect of the compound separated from the Malus asiatica fruit branches and leaves on the human leukemia K562 cell line is tested, and the test result shows that the compound has obvious cytotoxic effect on the human leukemia K562 cell line in vitro and the IC of the compound 50 The value was 0.12. + -. 0.01. Mu.M; testing in vitro anti-tumor effect of compound separated from Malus asiatica branches and leaves on human colon cancer HCT116 cell lineThe test result shows that the compound has obvious cytotoxic effect on human colon cancer HCT116 cell strain in vitro, and the IC of the compound is 50 The value was 0.09. + -. 0.04. Mu.M; therefore, the cyclopentane benzofuran compound separated from the branches and leaves of the equine kidney has in vitro anti-tumor activity and potential for preparing drugs for preventing and treating tumors, and the obtained compound provides a foundation for developing novel high-efficiency and low-toxicity anti-tumor drugs.
Drawings
FIG. 1 is a structural formula diagram of a cyclopentane benzofuran compound 1 with anti-tumor activity.
FIG. 2 Process for preparing cyclopentane benzofuran compound 1 with antitumor activity 1 HNMR spectrogram.
FIG. 3 shows the preparation of cyclopentane benzofuran compound 1 having antitumor activity 13 CNMR spectrogram.
Detailed Description
The following detailed description of the cyclopentane benzofuran compound, its preparation method and application according to the present invention is provided in connection with the preferred embodiments and experimental examples.
Example 1
A preparation method of a cyclopentane benzofuran compound with anti-tumor activity comprises the following steps:
(1) Taking 50 parts of dried branches and leaves of Malus asiatica, crushing, leaching for 3-5 times at room temperature by adopting 200 parts of 95% industrial methanol, extracting for 4 days each time, recovering alcohol, and concentrating to obtain 10 parts of extract;
(2) Performing silica gel column chromatography on the crude extract, performing gradient elution by using an eluent with the volume ratio of petroleum ether to acetone being 9-1, wherein the eluent is prepared from the following raw materials in a ratio of 1-1, each gradient is 100 parts, detecting different elution fractions by using a silica gel thin-layer chromatography technology, merging fractions with the same thin-layer chromatography result, and performing thin-layer chromatography to obtain seven fractions: 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 eluting with 25L gradients of eluent at a methanol to water volume ratio of 1. Detecting different elution fractions by using silica gel thin-layer chromatography, combining the fractions with the same thin-layer chromatography result, and combining the results displayed by the thin-layer chromatography to obtain 9 sub-fractions: 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); fr.6e is subjected to silica gel column chromatography, and the eluent with the volume ratio of petroleum ether to ethyl acetate of 1.
Structural identification of the compounds:
the compound is prepared by high resolution mass spectrometry and nuclear magnetic resonance spectroscopy ( 1 HNMR, 13 CNMR, 2D-NMR), ultraviolet spectrum, infrared spectrum, optical rotation, etc., to determine the structural formula of compound 1, as shown below:
compound 1: colorless crystal of 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-8 b), 90.2 (C-5), 93.4 (C-7), 103.3 (C-2), 106.5 (C-3 a), 109.0 (C-8 a), 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-4 a), 162.4 (C-1), 165.39 (C-1'), 165.44 (C-6). Process for preparation of Compound 1 1 HNMR, 13 The CNMR spectra are shown in FIGS. 2 and 3.
To further analyze the toxic inhibitory effect of compound 1 on human leukemia HEL cell line, human leukemia K562 cell line and human colon cancer HCT116 cell line, and to better use it in the preparation of antitumor drugs, compound 1 obtained in example 1 was subjected to the following experiment:
(1) Experimental materials
96-well culture plate, 1640 culture solution, fetal calf serum, 0.25% pancreatin, tetramethyl azo blue (3- (4, 5-dimethyl 1-thiazole-2-yl-tetrazolium bromide; MTT), dimethyl sulfoxide (dimethyl sulfoxide: DMSO), a centrifuge, a biological microscope and a microplate reader, wherein the selected tumor cell strains are human leukemia HEL cell strain, human leukemia K562 cell strain and human colon cancer HCT116 cell strain, the medicament is dissolved by DMS0 (dimethyl sulfoxide) to prepare storage solution, and the storage solution is stored at the temperature of 20 ℃ below zero for later use.
(2) Test method
Rapidly thawing tumor cells in the frozen tube in 37 deg.C water bath, centrifuging to collect cells, and adding antibiotic (100 IUmL) -1 Penicillin and 100IUmL -1 Streptomycin) and 10% fetal bovine serum in 1640 complete medium at 37 deg.C, 5% 2 Culturing in incubator with constant temperature and saturated humidity. When most of the cells are confluent, passage is carried out, and cells in logarithmic growth phase are selected for experiment. Transferring the cells into a centrifuge tube, centrifuging at 800r/min for 3min, discarding supernatant, adding new culture solution, inoculating tumor cells into 96-well plate (human leukemia HEL cells and human leukemia K562 cells adjusting cell concentration to 1 × 10) 4 Density per ml; human colon carcinoma HCT116 cells adjusted cell concentration to 7X 10 3 Density per ml), 100. Mu.L of cell broth was added per well, and adherent cells were inoculated and cultured 12 hours in advance. At 37 ℃ C, 5% CO 2 Cultured for 4 hours, and thenAdding different concentrations of compound 1 (fixed concentration 20 μ M primary sieve, in which the concentration of compounds with tumor cell growth inhibition rate of about 50% is set to 5 concentrations and then graded), at 37 deg.C, 5% 2 After the conditioning for 72 hours, 10. Mu.L of LMTT (5 g/L) was added to each well, and the culture was continued. Adding 100 mu L of triple solution for overnight culture, and measuring an absorption value at 570nm by using an enzyme-labeling instrument; the DMSO group was used as a blank control, and doxorubicin was used as a positive control, and each experiment was repeated three times.
(3) And (3) test results:
the cytotoxic effects of the cyclopentanoperhydropyran compounds on three human tumor cell lines are shown in the following table:
the results show that the compound 1 shows high-intensity cytotoxic effect on part of human tumor cell lines in vitro. Cytotoxic Activity of Compound 1 against human leukemia HEL cell line (IC) 50 0.12. + -. 0.04), cytotoxic activity (IC) against human leukemia K562 cell line 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 adriamycin to the human leukemia HEL cell line 50 0.14. + -. 0.03), cytotoxic activity (IC) against the human leukemia K562 cell line 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 biological activity, and provides a new medicament and a new way for the aspects of comprehensive utilization of Malus asiatica and development of medicaments for preventing and treating cancers.
The above description is only a preferred embodiment of the present invention, and is not intended to limit the present invention in any way, and any simple modification, equivalent change and modification made to the above embodiment according to the technical spirit of the present invention are within the scope of the present invention without departing from the technical spirit of the present invention.
Claims (8)
1. The compound is obtained by separating and extracting from horse kidney fruits for the first time, and the structural formula of the compound is (1):
2. the compound of cyclopentane benzofuran class with antineoplastic activity of claim 1, wherein the preparation method of said compound comprises the following steps:
(1) Taking 50 parts of Malus asiatica branches and leaves, crushing, leaching for 3-5 times at room temperature by adopting 200 parts of 95% industrial methanol, each time for 4 days, recovering methanol, and concentrating to obtain 10 parts of extract;
(2) And (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, wherein each gradient is 100 parts, detecting different elution fractions by using a silica gel thin-layer chromatography technology, combining fractions with the same thin-layer chromatography result, and performing thin-layer chromatography to obtain seven fractions: fr.1, fr.2, fr.3, fr.4, fr.5, fr.6 and 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 being 1-9, combining according to the thin-layer chromatography performance, and dividing into 9 sub-fractions: 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 the Fr.6e, and performing gradient elution by using an eluent with the volume ratio of petroleum ether to ethyl acetate being 1.
3. Use of the cyclopentanofuran compounds of claim 1 or claim 2, in the preparation of a medicament for inhibiting the activity of the HEL cell line of human leukaemia, the K562 cell line of human leukaemia and the HCT116 cell line of human colon cancer.
4. The use of a compound of the cyclopentafuran class having antitumor activity according to claim 3, wherein said compound, when used as a medicament, is administered directly or in the form of a pharmaceutical composition comprising from 0.1% to 99% of said compound with the remainder being pharmaceutically acceptable carriers or excipients.
5. The use of cyclopentaphenofurans having antitumor activity 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 product adjuvants.
6. The use of a cyclopentane benzofuran compound with anti-tumor activity according to claim 4, wherein said pharmaceutical composition is administered in the form of a unit weight dose.
7. The use of a compound of the cyclopentane benzofuran type having an antitumor activity according to claim 4, wherein the pharmaceutical composition is in a dosage form comprising: injection, suspension, emulsion, solution, syrup, tablet, capsule, granule, spray, and aerosol.
8. The use of the compound of formula i having anti-tumor activity according to claim 4, wherein the pharmaceutical composition is administered by the following routes: intravenous injection, intravenous drip, intramuscular injection, intraperitoneal injection, subcutaneous injection, oral administration, sublingual administration, and mucosal dialysis.
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| WO2004041812A1 (en) * | 2002-11-08 | 2004-05-21 | The Government Of The State Of Sarawak, Malaysia | Therapeutic compounds and methods |
| AU2001268848B2 (en) * | 2000-07-05 | 2005-12-15 | The Government Of The State Of Sarawak, Malaysia | Therapeutic compounds and methods |
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| WO2020086562A1 (en) * | 2018-10-22 | 2020-04-30 | Trustees Of Boston University | Compositions and methods for inhibiting viral infection |
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| CN115073407A (en) * | 2021-03-10 | 2022-09-20 | 上海中医药大学 | Medicinal composition with synthetic lethality and application thereof |
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2022
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| JPH0967375A (en) * | 1995-08-28 | 1997-03-11 | Terumo Corp | Suppressant for cancer gene function |
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| AU2001268848B2 (en) * | 2000-07-05 | 2005-12-15 | The Government Of The State Of Sarawak, Malaysia | Therapeutic compounds and methods |
| WO2004041812A1 (en) * | 2002-11-08 | 2004-05-21 | The Government Of The State Of Sarawak, Malaysia | Therapeutic compounds and methods |
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