CN104804057B - Pregnane alkaloid and preparation method thereof and the purposes in antineoplastic is prepared - Google Patents
Pregnane alkaloid and preparation method thereof and the purposes in antineoplastic is prepared Download PDFInfo
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- CN104804057B CN104804057B CN201410036401.2A CN201410036401A CN104804057B CN 104804057 B CN104804057 B CN 104804057B CN 201410036401 A CN201410036401 A CN 201410036401A CN 104804057 B CN104804057 B CN 104804057B
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07J—STEROIDS
- C07J41/00—Normal steroids containing one or more nitrogen atoms not belonging to a hetero ring
- C07J41/0005—Normal steroids containing one or more nitrogen atoms not belonging to a hetero ring the nitrogen atom being directly linked to the cyclopenta(a)hydro phenanthrene skeleton
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Abstract
Specification digest is related to the monomeric compound and its separation preparation and the purposes for treating tumour of the alkaloid containing pregnane the invention belongs to drug field.The present invention has carried out system research to the chemical composition of the Pachysandra plant stool fruit (pachysandra axillaris) of Sarcococca and its nearly edge and its pharmacological action, isolated class pregnane alkaloid and its monomeric compound, show that the compound of acquisition has good antitumor activity through pharmacology test.The pregnane alkaloid monomeric compound and combination can prepare antineoplastic, whole body or local application be given with carrier or excipient, for treating colon cancer, lung cancer, the cancer of the brain and breast cancer.
Description
Technical field
The invention belongs to drug field, the monomeric compound and its separation for being related to the alkaloid containing pregnane are prepared and are used for
Treat the purposes of tumour.
Background technology
It is reported that malignant tumour is one of major disease of current harm health of people.At present, tumour in clinical practice
Therapeutic scheme has the therapeutic schemes such as operation, radiation and chemotherapy.Chemotherapy is as one of three great tradition means of oncotherapy, in tumour
In occupation of critical role in treatment.The chemicals of known treatment tumour includes chemical synthetic drug and Chinese medical extract etc.,
The focus for finding that active component is always antineoplastic research in the industry is found from natural drug.
Buxaceae Sarcococca various plants are China's Chinese medicines among the people, are mainly used in treatment stomach trouble, bruise internal lesion caused by overexertion, dizziness
Palpitaition, throat swell and ache.Research finds that the plant contains alkaloid component, there is screening operation of the research in Antitumor Natural Products
In, it is found that the ethanol extract of Sarcococca plant fragrance osmanthus (Sarcococca ruscifolia) has to kinds of tumor cells
There is inhibitory activity, further investigation revealed that its antineoplastic main active is pregnane Alkaloid, it is for many years, domestic
Its suppression to acetylcholinesterase and butyrylcholine esterase being confined to the outer correlative study for this kind of pregnane Alkaloid more
System activity aspect.
So far, there is not yet the report of the system research of chemical composition and its pharmacological action about delicate fragrance osmanthus alkaloid position
Road.Present inventor intends providing new class pregnane alkaloid and preparation method thereof and in antineoplastic is prepared
Purposes.
Prior art related to the present invention has：
[1] .Kang He, et al.Two new steroidal alkaloids from the roots of
Sarcococca ruscifolia.Journal of Asian Natural Product Research, 2010,12 (3):
233-238.
[2] .Yun Sun, et al.Pregnane alkaloids from Pachysandra
Axillaris.Streoids, 2010,75:818-824.
[3] an enclosure for storing grains tor, waits the chemical research Acta Pharmaceutica Sinicas of steroid alkaloid in Buxaceaes, 1997,32 (11):
852-856.。
The content of the invention
It is an object of the invention to provide the new natural medicinal plant monomeric compound and drug regimen that are used to treat tumour.
It is specifically related to class pregnane alkaloid and preparation method thereof and the purposes in antineoplastic is prepared.
The present invention is to Sarcococca and its Pachysandra of nearly edge（Also known as Pachysandra terminalis belongs to）Plant stool fruit
The chemical composition of (pachysandra axillaris) and its pharmacological action have carried out system research, isolated including multiple
A class pregnane alkaloid including noval chemical compound, shows through pharmacology test, and there is multiple compounds of acquisition good resisting to swell
Tumor activity.
Natural medicinal plant monomeric compound of the present invention is pregnane Alkaloid compound, with formula（Ⅰ）'s
General structure.
In the present invention, in the skeleton of described pregnane steroid alkaloid, the connection between 2,3 and/or 16,17 it
Between connection can be singly-bound or double bond.
In the present invention, the substituent R on the 3- positions N atoms of described pregnane steroid alkaloid1If acyl group, Ke Yishi
And it is not limited to iso-amylene acyl group, benzoyl, crotonyl, cinnamoyl, substituted or unsubstituted phosphate acyl, sulphonyl
Base, benzenesulfonyl or other organic acid acyl groups.
In the present invention, the substituent R on the 20- positions N atoms of described pregnane steroid alkaloid3And R4Can be hydrogen or
Methyl.
In the present invention, the 4- positions of described pregnane steroid alkaloid and R2Connected key can be singly-bound or double bond.
In the present invention, the R of described pregnane steroid alkaloid 4-2Group can be and be not limited to hydrogen, alkyl, contain
Oxygen groups, nitrogen-containing group, sulfur-containing group or other heteroatom groups.
In the present invention, the R of described pregnane steroid alkaloid 4-2If group oxy radical, then can for hydroxyl or
4- carbonyls.
Pregnane steroid alkaloid compound of the present invention can be fanned by extracting the method for separation from Buxaceae open country
Flower category is isolated with Pachysandra plant or other root of Roundfruit Licorice of category containing similar pregnane alkaloid, especially from open country fan
It is isolated in the delicate fragrance osmanthus of flower category or the stool fruit plant of Pachysandra.
The separation of monomeric compound of the present invention can be prepared by chromatography separating method.
The chromatographic isolation of monomeric compound of the present invention can use positive phase alumina or silica gel chromatograph method, use oil
The organic solvents such as ether, dichloromethane, chloroform, ethyl acetate, acetone, ethanol, methanol are used as eluant, eluent.
The chromatographic isolation of monomeric compound of the present invention can use reverse-phase chromatography method, and reverse-phase chromatography filler can be
But it is not limited to C18Bonded-phase silica, C8Bonded-phase silica, phenyl bonded-phase silica, cyano bonded phase silica gel etc..
The chromatographic isolation of monomeric compound of the present invention can using gel, macroporous absorbent resin, ion exchange resin,
The chromatographic process of methacrylic polymeric resin, is eluted with alcohol-water mixed solvent.
Currently preferred monomeric compound is：
Compound 1
White powder (methanol), bismuth potassium iodide shows orange red, illustrates for alkaloid component；m.p.134-136℃；IR
(KBr)：3384cm-1, 1664cm-1, 1643cm-1, 1511cm-1；[α]D17：+37.50(c:0.064, CHCl3)；HR-ESIMS
m/z427.3312[M+H]+；1H-NMR(CDCl3, 400MHz) and13C-NMR(CDCl3, 100MHz) and data are shown in Table 1.According to wave spectrum
Data, deduction compound 1 is the α -2- pregnene -4- ketone of (20s) -20- methylamino -3- senecioyls amido -5, is a new day
Right pregnane Alkaloid, is named as delicate fragrance osmanthus alkali E (Sarcorucinine E).
Compound 2
White powder (methanol), bismuth potassium iodide shows orange red, illustrates for alkaloid component；m.p.265-267℃；IR
(KBr)：3418cm-1, 1665cm-1, 1641cm-1；[α]D 18：+42.00(c:0.1, CHCl3)；HR-ESI-MS m/
z425.3167[M+H]+；1H-NMR(CDCl3, 400MHz) and13C-NMR(CDCl3, 100MHz) and data are shown in Table 1.According to wave spectrum number
According to deduction compound 2 is α -2, the 16- pregnen diethylene -4- ketone of (20s) -20- methylamino -3- senecioyls amido -5, is one new
Natural pregnane Alkaloid, is named as delicate fragrance osmanthus alkali F (Sarcorucinine F).
Compound 3
White powder (methanol), bismuth potassium iodide shows orange red, illustrates for alkaloid component；m.p.186-188℃；IR
(KBr)：3388cm-1, 1642cm-1, 1603cm-1, 1574cm-1, 1488cm-1, 720cm-1；[α]D 17：-40.63(c:0.064,
CHCl3)；HR-ESI-MS m/z449.3512[M+H]+；1H-NMR(CDCl3, 500MHz) and13C-NMR(CDCl3, 100MHz)
Data are as shown in table 2.According to spectral data, deduction compound 3 is (20s) -20- (N, TMSDMA N dimethylamine base) -3 β-benzamide
α -16- the pregnenes of base -5, are a new natural pregnane Alkaloid, are named as delicate fragrance osmanthus alkali G (Sarcorucinine G).
Compound 4
White powder, bismuth potassium iodide shows orange red, illustrates for alkaloid component；m.p.246-248℃；[α]D 17：+6.84
(c:0.19, CHCl3)；ESI-MS m/z451.5[M+H]+；13C-NMR(CDCl3, 100MHz) and data are shown in Table 2.Compound 4 and text
The yellow amine D controls of table powder stamen for offering report are basically identical, and the structure for determining the compound is：(20S)-20-(N,N-
Dimethylamino) α-the pregnane of -3 β-(benzamido) -5, i.e. table powder stamen Huang amine D (epipachysamine D).
Compound 5
White powder (methanol), bismuth potassium iodide shows orange red, illustrates for alkaloid component；m.p.96-98℃；[α]D 17：+
39.84(c:0.374, CHCl3)；ESI-MS m/z441.3[M+H]+；13C-NMR(CDCl3, 100MHz) and data are shown in Table 3.Chemical combination
Thing 5 compares basically identical with the pachysandrine M of document report, and the structure for determining the compound is：(20s)-20-(N,N-
Dimethylamino) -3 β-senecioylamino-5 α-pregn-2-ene-4-one, i.e. pachysandrine M (pachysamine
M)。
Compound 6
White powder (methanol), bismuth potassium iodide shows orange red, illustrates for alkaloid component；m.p.170-172℃；[α]D 18：
+82.56(c:0.086, CHCl3)；ESI-MS m/z441.2[M+H]+；13C-NMR(CDCl3, 100MHz) and tables of data 3.Compound
6 compare basically identical with the Sarcovagine D of document report, and the structure for determining the compound is：(20s)-20-(N,N-
Dimethylamino) -3 β-tigoylamino-5 α-pregn-2-ene-4-one, i.e. Sarcovagine D.
The NMR data of the compound 1 and 2 of table 1
The NMR data of the compound 3 and 4 of table 2
The NMR data of the compound 5 and 6 of table 3
Pregnane steroid alkaloid of the present invention can further prepare antineoplastic or be made with other drugs and control
Treat the drug regimen of tumour.
Pregnane steroid alkaloid and its monomeric compound and drug regimen of the present invention are mainly used in but not limited to
In treatment colon cancer, lung cancer, the cancer of the brain and breast cancer, the medicine can by suppress A549, H1299, HCT116, HT29,
The growth of the different types of tumour cell such as U87, U251, MCF-7 and BT549, cause Apoptosis to reach treatment tumour
Effect
The pregnane Alkaloid monomeric compound and drug regimen available support or excipient of the present invention give whole body or
Local administration, more specifically can intranasal, it is oral, transdermal, through enteron aisle, vein or administered intramuscular.
Embodiment
The extraction and separation of the compound 1 of embodiment 1
Delicate fragrance osmanthus (Sarcococca ruscifolia) rhizome crushes (635g) afterwards with 95% alcohol diacolation.Be concentrated under reduced pressure for
Alcohol medicinal extract, is suspended in after water and is extracted respectively with petroleum ether, chloroform and ethyl acetate, obtain petroleum ether, chloroform, ethyl acetate and
Water layer totally three positions.
After the oxidized aluminium pillar layer separation of chloroform extract, then use C18Reversed phase chromatography separation, with water-methanol (20:80-10:
90) gradient elution is carried out, compound 1 is obtained：White powder, 10.1mg；mp134-136℃；IR(KBr)：3384cm-1, 1664cm-1, 1643cm-1,1511cm-1；[α]D 16.8：+37.50(c:0.064,CHCl3)；ESI-MS m/z427.3[M+H]+；Nuclear-magnetism is total to
Data of shaking are as shown in table 1.
The extraction and separation of the compound 2 of embodiment 2
Take after the oxidized aluminium pillar layer separation of above-mentioned delicate fragrance osmanthus chloroform extract, then use C18Reversed phase chromatography separation, uses water-methanol
(15:85) eluted, obtain compound 2：White powder, 9.1mg；mp265-267℃；IR(KBr)：3418cm-1, 1665cm-1,1641cm-1；[α]D 17.7：+42.00(c:0.1,CHCl3)；ESI-MSm/z425.4[M+H]+；The nuclear magnetic resonance data such as institute of table 1
Show.
The extraction and separation of the compound 3 of embodiment 3
Take after the oxidized aluminium pillar layer separation of above-mentioned delicate fragrance osmanthus chloroform extract, then use C18Reversed phase chromatography separation, uses water-methanol
(10:90) eluted, obtain compound 3：White powder, 8mg；mp186-188℃；IR(KBr)：3388cm-1, 1642cm-11,
1603cm-1, 1574cm-1, 1488cm-1, 720cm-1；[α]D 17.4：-40.63(c:0.064, CHCl3)；ESI-MS m/z449.4
[M+H]+；Nuclear magnetic resonance data is as shown in table 2.
The extraction and separation of the compound 4 of embodiment 4
Take after the oxidized aluminium pillar layer separation of above-mentioned delicate fragrance osmanthus chloroform extract, then use C18Reversed phase chromatography separation, uses water-methanol
(20:80-10:90) gradient elution is carried out, compound 4 is obtained：White powder, 30.1mg；mp246-248℃；[α]D 17.0：+6.84
(c:0.19,CHCl3)；ESI-MS m/z451.5[M+H]+；Nuclear magnetic resonance data is as shown in table 2.
The extraction and separation (1) of the compound 5 of embodiment 5
Take after the oxidized aluminium pillar layer separation of above-mentioned delicate fragrance osmanthus chloroform extract, then use C18Reversed phase chromatography separation, uses water-methanol
(10:90) eluted, obtain compound 5：White powder, 15mg；mp96-98℃；[α]D 17.4：+39.84(c:0.374,
CHCl3)；ESI-MS m/z441.3[M+H]+；Nuclear magnetic resonance data is as shown in table 3.
The extraction and separation (2) of the compound 5 of embodiment 6
With 95% alcohol diacolation after stool fruit (pachysandra axillaris) rhizome (500g) crushing.Be concentrated under reduced pressure for
Alcohol medicinal extract, is suspended in after water and is extracted respectively with petroleum ether, chloroform and ethyl acetate, obtain petroleum ether, chloroform, ethyl acetate and
Water layer totally three positions.
Take after the oxidized aluminium pillar layer separation of chloroform extract, then use C18Reversed phase chromatography separation, with water-methanol (10:90) enter
Row elution, obtains compound 5：4.2mg.
The extraction and separation (1) of the compound 6 of embodiment 7
Take after the oxidized aluminium pillar layer separation of above-mentioned delicate fragrance osmanthus chloroform extract, then use C18Reversed phase chromatography separation, uses water-methanol
(10:90) eluted, obtain compound 6：White powder, 27.8mg；mp170-172℃；[α]D 17.6：+82.56(c:0.086,
CHCl3)；ESI-MS m/z441.2[M+H]+；Nuclear magnetic resonance data is as shown in table 3.
The extraction and separation (2) of the compound 6 of embodiment 8
Take after the oxidized aluminium pillar layer separation of stool fruit chloroform extract, then use C18Reversed phase chromatography separation, with water-methanol (10:
90) eluted, obtain compound 6：5.5mg.
The anti-tumor activity test of embodiment 9
Human lung carcinoma cell line A549, H1299, Human colorectal cancer cells strain HCT116, HT29, Breast cancer lines MCF-
7th, BT-549 and people's glioblastoma U87, U251 37 °C contain 5%CO2 under the conditions of be incubated at containing 10% hyclone,
In the DMEM nutrient solutions of 50kU/L penicillin and 50mg/L streptomysins, pancreatin digestion again with nutrient solution diluting cells concentration to 5 ×
104Individual/ml, takes 100 μ l to add in the hole of 96 orifice plates, then adds after the cancer therapy drug of various concentrations, culture 68h, per hole
The MTT for adding 10 μ l5mg/ml is further cultured for 4h, then abandons the DMSO that nutrient solution adds 100 μ l per hole, is read with ELIASA in 490nm
Take the light absorption value in every hole.IC is calculated with Bliss methods50Value.As a result it is as shown in table 4.
Anti-tumor activity test (the IC of table 4.50,μM)
Claims (4)
1. purposes of the pregnane alkaloid monomeric compound in antineoplastic is prepared；
Described pregnane alkaloid monomeric compound is made as follows：Spent by chromatography separating method from Buxaceae open country fan
Platymiscium delicate fragrance osmanthus is carried with the stool fruit of Pachysandra plant or in other root of Roundfruit Licorice of category containing similar pregnane alkaloid
Take isolated following monomeric compounds：
Compound 1：α -2- pregnene -4- the ketone of (20s) -20- methylamino -3- senecioyls amido -5；
Compound 2：α -2,16- pregnen diethylene -4- the ketone of (20s) -20- methylamino -3- senecioyls amido -5；
Compound 3：(20s) -20- (N, TMSDMA N dimethylamine base) -3 β-α -16- pregnenes of benzamido -5；
In described chromatography separating method, using positive phase alumina or silica gel chromatograph method, with petroleum ether, dichloromethane, chloroform,
Ethyl acetate, acetone, ethanol or methanol organic solvent are used as eluant, eluent；
Or, reverse-phase chromatography method is used, reverse-phase chromatography filler selects C18Bonded-phase silica, C8Bonded-phase silica, phenyl Bonded Phase
Silica gel or cyano bonded phase silica gel, are eluted with alcohol-water mixed solvent；
Or, using gel, macroporous absorbent resin, ion exchange resin, the chromatographic process of methacrylic polymeric resin, with alcohol-
Water mixed solvent is eluted.
2. the purposes as described in claim 1, it is characterised in that described tumour is colon cancer, lung cancer, the cancer of the brain or breast cancer.
3. the purposes as described in claim 1, it is characterised in that described antineoplastic by suppress A549, H1299,
The growth of HCT116, HT29, U87, U251, MCF-7 or BT549 tumour cell, causes Apoptosis, reaches treatment tumour.
4. the purposes as described in claim 1, it is characterised in that described antineoplastic gives whole body with carrier or excipient
Or local administration.
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| CN109180765B (en) * | 2018-09-06 | 2021-03-23 | 贵阳中医学院 | Pregnane steroid alkaloid and preparation method and application thereof |
| CN109091481A (en) * | 2018-09-29 | 2018-12-28 | 贵阳中医学院 | A kind of application of pregnane type open country fan peanut alkaloids |
| CN109172581A (en) * | 2018-09-29 | 2019-01-11 | 贵阳中医学院 | A kind of application of wild fan peanut alkaloids |
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