CN113801000A - Compound with anti-tumor activity and preparation method and application thereof - Google Patents
Compound with anti-tumor activity and preparation method and application thereof Download PDFInfo
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Abstract
The invention discloses an anti-tumor compound and a preparation method and application thereof. The compound disclosed by the invention is an enantiomer-kaurane diterpene new compound, is identified as 16 beta-17-hydroxy-18-nor-ent-kaurane-4 beta-ol, and has a molecular formula of C19H32O2. The invention carries out deep research on the effective components of the cherimoya pericarp through a large amount of experimental screening, and obtains the novel enantiomer-kaurene diterpenoid compound with obvious anticancer activity through percolation extraction and normal phase silica gel column chromatographic separation. The preparation process and design provided by the inventionReasonable, strong operability, can realize the resource utilization of the waste sweetsop peels, and has important application value.
Description
Technical Field
The invention relates to a method for extracting and separating traditional Chinese medicines and application thereof, in particular to an enantiomorph-kaurane diterpenoid compound with anti-tumor activity, which is separated from cherimoya pericarp.
Background
Liver cancer is the cancer species with the highest incidence in China, and has the characteristics of high mortality rate due to high hiding property and high probability of late stage discovery. Interventional therapy (local chemotherapy) is an important means for treating middle and late-stage liver cancer, but the toxic and side effects of chemotherapeutic drugs seriously harm the health of patients, so that the development of natural drugs with anti-liver cancer activity becomes an important direction for liver cancer research.
Tropical famous fruit Annona squamosa, also named Sakya and Froude, is documented to be capable of treating sore and swelling pain. The sweetsop seeds are used as a local traditional Chinese medicine in Guangdong province and are widely used for treating tumors including liver cancer. Earlier researches find that the annona squamosa peel extract has good anti-liver cancer activity, and active ingredients of the annona squamosa peel extract are mainly concentrated on small polar parts.
The cherimoya pericarp is used as a potential anti-liver cancer drug and is discarded as waste all the time, and in order to change waste into valuable, the invention separates the small polar components of the cherimoya pericarp and screens out the anti-liver cancer active components thereof.
Disclosure of Invention
The purpose of the invention is as follows: the first purpose of the invention is to separate a new enantiomer-kaurane diterpenoid compound 16 beta-17-hydroxy-18-nor-ent-kaurane-4 beta-ol with molecular formula C from annona squamosa peel19H32O2The structural formula is as follows:
the second purpose of the invention is to provide a preparation method for extracting and separating a new compound 16 beta-17-hydroxy-18-nor-ent-kaurane-4 beta-ol from annona squamosa pericarp, which comprises the following steps:
(1) pulverizing air-dried sweetsop pericarp into coarse powder, wetting, transferring into a percolating cylinder, percolating with ethanol at room temperature, mixing the percolate, placing in a rotary evaporator, and concentrating under reduced pressure to obtain extract;
(2) dissolving the ethanol extract with ethyl acetate, mixing the sample with silica gel to obtain dry fine powder, filling the dry fine powder into a column by using a silica gel wet method, loading the sample, performing gradient elution by using petroleum ether-ethyl acetate and ethyl acetate-methanol, detecting by using a thin-layer analysis panel, merging the same fractions to obtain 15 parts, and sequentially numbering the parts as F1-F15;
(3) taking the F5 part, mixing the sample by a dry method, loading the sample into a silica gel column, mixing the mixture with petroleum ether: eluting with acetone system, and dividing into 5 segments, F5-1, F5-2, F5-3, F5-4 and F5-5; combining F5-1 and F5-2, and performing gradient elution with petroleum ether-acetone to obtain the ent-kaurane diterpene compound.
As a preferred scheme, the preparation method for extracting and separating the new compound 16 beta-17-hydroxy-18-nor-ent-kaurane-4 beta-ol from the cherimoya pericarp comprises the following steps:
(1) taking 8kg of air-dried sweetsop pericarp, crushing into coarse powder, transferring the coarse powder into a percolation cylinder after being properly wetted, and percolating and extracting for three times at room temperature by adopting 10 times volume of 95% EtOH. Mixing extractive solutions, and concentrating the extractive solution under reduced pressure in rotary evaporator to obtain 400g ethanol extract.
(2) Dissolving 400g of ethanol extract with ethyl acetate, stirring the mixture with 400g of silica gel (200 meshes) to obtain dry fine powder, carrying out wet column packing by adopting 2kg of silica gel (200 meshes) and 300 meshes), carrying out gradient elution by using petroleum ether-ethyl acetate (1:0, 50:1, 25:1, 10:1, 5:1, 2:1, 1:1, 1:2, 1:5, 0:1) and ethyl acetate-methanol (100:1, 50:1, 10:1, 0:1) after sample loading, taking each 1L of the mixture as a fraction, merging the same fractions by thin layer analysis panel detection to obtain 15 fractions which are sequentially numbered from F1 to F15.
(3) Taking the F5 part, mixing the sample by a dry method, loading the sample into a silica gel column, mixing the mixture with petroleum ether: the acetone system elutes, and the eluate is divided into 5 segments, namely F5-1, F5-2, F5-3, F5-4 and F5-5. The F5-1 and F5-2 sections have relatively small amount and more overlap, so that the sections are combined and are subjected to gradient elution by petroleum ether-acetone (100: 1-20: 1) to obtain the enantiomer-kaurane diterpenoid new compound 6 beta-17-hydroxy-18-nor-ent-kaurane-4 beta-ol.
The third purpose of the invention is to prepare the compound and a pharmaceutically acceptable carrier into tablets, capsules, sprays, injections or transdermal controlled release patches for oral or external use, thereby realizing the medicinal application of the novel compound in the aspect of preventing and treating liver cancer.
Has the advantages that:
the invention carries out deep research on the effective components of the cherimoya pericarp through a large number of experimental screenings, and obtains the enantiomorph-kaurane diterpenoid new compound 6 beta-17-hydroxy-18-nor-ent-kaurane-4 beta-ol with obvious anticancer activity through percolation extraction and normal phase silica gel column chromatographic separation. The preparation process provided by the invention has the advantages of reasonable design and strong operability, can realize the resource utilization of the waste sweetsop peels, and has important application value.
Drawings
FIG. 1 is a diagram of HMBC of the novel compound;
FIG. 2 is a NOESY diagram of the novel compounds;
FIG. 3 is a HRESI-MS plot of the novel compounds;
FIG. 4 is a drawing showing the preparation of the novel compound1H NMR chart;
FIG. 5 is a drawing showing the preparation of the novel compound13C NMR chart;
FIG. 6 is a HSQC graph of the novel compounds;
FIG. 7 is a HMBC diagram of the novel compound;
FIG. 8 is a NOESY plot of the novel compounds.
DETAILED DESCRIPTION OF EMBODIMENT (S) OF INVENTION
The following examples are presented to enable one of ordinary skill in the art to more fully understand the present invention and are not intended to limit the invention in any way.
Example 1
The method for extracting and separating the enantiomer-kaurane diterpenoid new compound 6 beta-17-hydroxy-18-nor-ent-kaurane-4 beta-ol from the cherimoya pericarp comprises the following steps:
(1) taking 8kg of air-dried sweetsop pericarp, crushing into coarse powder, transferring the coarse powder into a percolation cylinder after being properly wetted, and percolating and extracting for three times at room temperature by adopting 10 times volume of 95% EtOH. Mixing extractive solutions, and concentrating the extractive solution under reduced pressure in rotary evaporator to obtain 400g ethanol extract.
(2) Dissolving 400g of ethanol extract with ethyl acetate, stirring the mixture with 400g of silica gel (200 meshes) to obtain dry fine powder, carrying out wet column packing by adopting 2kg of silica gel (200 meshes) and 300 meshes), carrying out gradient elution by using petroleum ether-ethyl acetate (volume ratio of 1:0, 50:1, 25:1, 10:1, 5:1, 2:1, 1:1, 1:2, 1:5, 0:1) and ethyl acetate-methanol (volume ratio of 100:1, 50:1, 10:1, 0:1), taking each 1L as one fraction, detecting and merging the same fractions by using a thin layer analysis panel to obtain 15 fractions, wherein the fractions are sequentially numbered as F1-F15.
(3) Taking the F5 part, mixing the sample by a dry method, loading the sample into a silica gel column, mixing the mixture with petroleum ether: the acetone system elutes, and the eluate is divided into 5 segments, namely F5-1, F5-2, F5-3, F5-4 and F5-5. F5-1 and F5-2 are relatively less in amount and more in overlap, so that the two sections are combined and subjected to gradient elution by petroleum ether-acetone (the volume ratio is 100: 1-20: 1) to obtain the ent-kaurane diterpenoid new compound 6 beta-17-hydroxy-18-nor-ent-kaurane-4 beta-ol.
Using nuclear magnetic resonance spectroscopy (1H NMR、13C NMR, HSQC, HMBC, NOESY) and high resolution mass spectrometry.
The compound is white powder, is easily dissolved in methanol and is mp.223-224 ℃. HRESI-MS M/z 293.2480 ([ M + H)]+，Calcd.For C19H33O2293.2481), from which it is concluded that its formula is C19H32O2The unsaturation degree Ω is 4. As shown in FIGS. 1-8,1H NMR(400MHz,DMSO-d6) Shows two methyl groups deltaH0.92(s,3H, H-20),0.96(s,3H, H-19). Bonding of13C NMR(100MHz,DMSO-d6) And HSQC confirmed 19 carbon signals including 2 methyl groups, 10 methylene groups, 4 methine groups and 3 quaternary carbons. HMBC spectra according to OH (. delta.)H3.89) to C-3 (. delta.)C43.0)、C-4(δC70.4)、C-5(δC57.2) and C-19 (. delta.))C22.9) can conclude that OH is located on C-4; OH (. delta.) ofH4.28) and C-17 (. delta.))C62.4) can infer CH2The presence of OH; h-13 (delta)H2.08) and H-15 (. delta.))H1.00) to C-17 (. delta.))C62.4) can infer CH2OH is 17 position. Similarly, values for each carbon of the compound can be assigned based on correlations between other data in the HMBC spectrum. From the NOESY spectrum, OH (. delta.) is shownH3.89)/H-3(δH1.46,1.59) indicates that the OH at the C-4 position is above the plane, beta-type, CH3In position 19, alpha-form; h-17 (delta)H3.45)/H-13(δH2.08)，H-17(δH3.45)/H-14(δH2.04) indicates that C-17 is in the alpha form under the plane. By combining the analysis, the compound is identified as 16 beta-17-hydroxy-18-nor-ent-kaurane-4 beta-ol, and is searched by a SciFinder database system and converted into the compoundThe compound is not reported in relevant documents, and the compound is shown to be a new enantiomer-kaurane diterpene.
TABLE 1 Hydrogen and carbon nuclear magnetic resonance spectroscopy data for compounds
| Carbon position | δH | δC | Carbon position | δH | δC |
| C-1 | CH2,0.70,1.69,m | 39.57 | C-11 | CH2,1.60,m | 19.60 |
| C-2 | CH2,1.79,m | 18.97 | C-12 | CH2,1.39,1.54,m | 25.90 |
| C-3 | CH2,1.46,1.59,m | 43.02 | C-13 | CH,2.08,m | 36.95 |
| C-4 | 70.45 | C-14 | CH2,1.25,2.04,m | 42.84 | |
| C-5 | CH,0.79,m | 57.20 | C-15 | CH2,1.00,1.44,m | 44.16 |
| C-6 | CH2,1.17,m | 19.15 | C-16 | CH,0.84,m | 43.94 |
| C-7 | CH2,0.93,m | 40.41 | C-17 | CH2,3.45,m | 62.35 |
| C-8 | - | 41.67 | C-18 | OH,3.89,s | - |
| C-9 | CH,1.00,m | 57.07 | C-19 | CH3,0.96,s | 22.91 |
| C-10 | - | 39.79 | C-20 | CH3,0.92,s | 17.48 |
。
Example 2: cytotoxic activity of the compound 6 beta-17-hydroxy-18-nor-ent-kaurane-4 beta-ol on SMMC-7721 cells.
Uniformly inoculating SMMC-7721 liver cancer cells in exponential division period into a 96-well plate, inoculating 8000 cells per well, after 24h, administering a new compound 6 beta-17-hydroxy-18-nor-ent-kaurane-4 beta-ol (with the highest concentration of 200 mu g/mL) with different concentrations, setting a blank control, after 48h, adding 20 mu L of MTT solution into each well, after incubating for 4h, removing culture solution, adding 150 mu L of DMSO, shaking uniformly, detecting absorbance value at 490nm on an enzyme labeling instrument, and calculating IC (integrated Circuit) value50The value is obtained. The above experiment is repeated three times to finally obtain the IC50It was 382.17. mu. mol/L. Shows better anti-tumor activity.
The foregoing is only a preferred embodiment of the present invention, and it should be noted that, for those skilled in the art, various modifications and decorations can be made without departing from the principle of the present invention, and these modifications and decorations should also be regarded as the protection scope of the present invention.
Claims (6)
1. An ent-kaurane-type diterpene compound having an antitumor activity, characterized in that: the molecular formula of the compound is C19H32O2The structural formula is as follows:
2. the method for extracting and separating an ent-kaurane diterpene compound having an antitumor activity according to claim 1, which comprises the steps of,
(1) pulverizing air-dried sweetsop pericarp into coarse powder, wetting, transferring into a percolating cylinder, percolating with ethanol at room temperature, mixing the percolate, placing in a rotary evaporator, and concentrating under reduced pressure to obtain extract;
(2) dissolving the ethanol extract with ethyl acetate, mixing the sample with silica gel to obtain dry fine powder, filling the dry fine powder into a column by using a silica gel wet method, loading the sample, performing gradient elution by using petroleum ether-ethyl acetate and ethyl acetate-methanol, detecting by using a thin-layer analysis panel, merging the same fractions to obtain 15 parts, and sequentially numbering the parts as F1-F15;
(3) taking the F5 part, mixing the sample by a dry method, loading the sample into a silica gel column, mixing the mixture with petroleum ether: eluting with acetone system, and dividing into 5 segments, F5-1, F5-2, F5-3, F5-4 and F5-5; combining F5-1 and F5-2, and performing gradient elution with petroleum ether-acetone to obtain the ent-kaurane diterpene compound.
3. The method for extracting and separating ent-kaurane diterpene compounds having antitumor activity according to claim 2, comprising the steps of,
(1) taking air-dried cherimoya peels, crushing the cherimoya peels into coarse powder, transferring the coarse powder into a percolation cylinder after wetting, carrying out percolation extraction for 1-3 times by adopting 10 times volume of 95% ethanol at room temperature, combining percolation extraction solutions, placing the percolation extraction solutions in a rotary evaporator, and carrying out reduced pressure concentration to obtain an extract;
(2) dissolving the ethanol extract with ethyl acetate, mixing the ethanol extract with silica gel to obtain dry fine powder, filling the dry fine powder into a column by using a silica gel wet method, performing gradient elution on petroleum ether-ethyl acetate with the volume ratio of 1:0, 50:1, 25:1, 10:1, 5:1, 2:1, 1:1, 1:2, 1:5 and 0:1 and ethyl acetate-methanol with the volume ratio of 100:1, 50:1, 10:1 and 0:1 after loading the sample, taking each 1L of the ethyl acetate-methanol as a fraction, and merging the same fractions by using a thin-layer analysis display board to obtain 15 parts, wherein the parts are sequentially numbered as F1-F15;
(3) taking an F5 part, mixing the part by a dry method, filling the mixture into a silica gel column, and mixing the mixture with petroleum ether in a volume ratio of 50: 1-1: eluting with acetone system, and dividing into 5 segments, F5-1, F5-2, F5-3, F5-4 and F5-5; and combining the F5-1 and the F5-2, and performing gradient elution by petroleum ether-acetone according to the volume ratio of 100: 1-20: 1 to obtain the ent-kaurane diterpenoid compound.
4. Use of the ent-kaurane diterpene compound having an antitumor activity according to claim 1 for the preparation of a medicament for the treatment of tumors.
5. The use of the ent-kaurane diterpene compound having an antitumor activity according to claim 1 for the preparation of a medicament for treating liver cancer.
6. Use according to claim 4 or 5, wherein the compound and the pharmaceutically acceptable carrier are formulated as a tablet, capsule, spray, injection or transdermal controlled release patch.
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| CN114671759A (en) * | 2022-03-28 | 2022-06-28 | 泰州职业技术学院 | Ent-kaurane diterpenoid compound with anti-tumor activity and preparation method and application thereof |
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| CN112110819A (en) * | 2020-09-30 | 2020-12-22 | 黑龙江省中医药科学院 | Diterpenoid compounds in corn stigma ethyl acetate extract, extraction method and application |
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| CN112110819A (en) * | 2020-09-30 | 2020-12-22 | 黑龙江省中医药科学院 | Diterpenoid compounds in corn stigma ethyl acetate extract, extraction method and application |
Non-Patent Citations (3)
| Title |
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| CHANG-XIN ZHOU，ET AL.: "Cytotoxic Diterpenoids from the Stem Bark of Annona squamosa L.", 《HELVETICA CHIMICA ACTA》 * |
| YU-LIANG YANG，ET AL.: "New ent-Kaurane Diterpenoids with Anti-Platelet Aggregation Activity from Annona squamosa", 《J. NAT. PROD.》 * |
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| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN114671759A (en) * | 2022-03-28 | 2022-06-28 | 泰州职业技术学院 | Ent-kaurane diterpenoid compound with anti-tumor activity and preparation method and application thereof |
| CN114671759B (en) * | 2022-03-28 | 2024-04-12 | 泰州职业技术学院 | Enantiomer-kaurane diterpenoid compound with anti-tumor activity and preparation method and application thereof |
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