CN108948040B - Gilmaxane type sesquiterpene compound extracted from herba Centellae and application thereof - Google Patents

Gilmaxane type sesquiterpene compound extracted from herba Centellae and application thereof Download PDF

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CN108948040B
CN108948040B CN201810733042.4A CN201810733042A CN108948040B CN 108948040 B CN108948040 B CN 108948040B CN 201810733042 A CN201810733042 A CN 201810733042A CN 108948040 B CN108948040 B CN 108948040B
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germacrane
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晏晨
张云东
孙茂
张卫青
梁伟
王天元
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Anshun people's hospital
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Abstract

A germacrane type sesquiterpene Carpescernolides A compound extracted from herba Centellae is obtained by separating and extracting whole plant of herba Centellae with structural formula of (І), and its preparation method comprises ethanol extraction, extract concentration, silica gel column chromatography, gradient elution, gel column chromatography, and semi-preparative high performance liquid chromatography purification. The invention discloses a gemmarane type sesquiterpene Carpeschernolides A compound which is extracted and separated from Bidens pinnatifida (Bidens pinnatifida) of Anshuzhen in Guizhou for the first time, the structural formula of the compound is determined, the compound has a treatment effect on cells of human liver cancer cells SMMC-7721, can induce apoptosis of the SMMC-7721 cells, promotes generation and accumulation of endogenous ROS in a dose-dependent manner, inhibits migration of tumor cells, inhibits formation of tumor cell clone, can be applied to preparation of a medicament for treating liver cancer, and can be used as a leading compound of the medicament for treating liver cancer.

Description

Gilmaxane type sesquiterpene compound extracted from herba Centellae and application thereof
Technical Field
The invention belongs to the field of medicines, and particularly relates to a germacrane type sesquiterpene Carpescernolides A compound extracted from herba leontici, and a preparation method and application thereof.
Background
The herba Centipedae (Carpesium cernuum) is plant of Carpesium of Compositae (Comosidae). The part used as the medicine is full grass, pungent, cool and bitter. Has little toxicity. Mainly survives in the area with the altitude of about 60-3,000 meters, mainly grows in hills, wastelands and ditches, and is distributed in Asia and Europe and the like. The southwest area, the central area and the north China are all rich in species. The tobacco pipe head is often prepared as an essence raw material by a method of extracting aromatic oil. Used as Yi medicine of national medicine for treating toothache, parotitis, bronchitis, asthma, urinary tract infection, mastitis, venomous snake bite, etc.; the white drug is used for treating dysentery, excessive damp-heat, pneumonia, pharyngolaryngitis, diarrhea, malaria and the like; lisuzu nationality Lisuzu nationality can be used for treating acute enteritis, common cold, fever, sore, furuncle, toxic swelling, and lymphoid tuberculosis; dong people mainly treat furuncle and swelling and Jiuzi sheep. Miao ethnomedicine can treat facial wind syndrome, stranguria and various inflammations, is used as wild tobacco leaf in Guizhou, and is a monarch drug in the patent prescription of Shuang Yang Hou bitong Tong Ke (Shuang Yang Hou Tong granule for treating pharyngitis) with the effects of resisting bacteria and diminishing inflammation. At present, the main chemical components of the herba epilaginellae reported in related documents comprise flavone, phenol, steroid, lignin, triterpene and sesquiterpene, and the coumarin is a fresh report, wherein the sesquiterpene with alpha, beta-unsaturated five-membered lactone ring is the main component of the herba epilaginellae, and the documents report that the herba epilaginellae have wide antitumor activity, but the action mechanism of the herba epilaginellae is not clear at present.
In the reports of the literature, the carpesium plant has a complex structure, and in the Guizhou carpesium of the same genus with Qian medicinal tobacco pipe, a novel structure, sesquiterpene lactone and sesquiterpene lactone dimer components are found, and the components have certain selective effects on leukemia. So far, no research report on extracting gemma alkane type sesquiterpene Carpescernolides A from natural plants and activity thereof exists in the prior art.
Disclosure of Invention
The invention aims to provide a germacrane type sesquiterpene Carpeschernolides A compound extracted from herba Clausenae Lansii, a preparation method thereof and application of the compound in preparing a medicament for treating liver cancer.
The purpose of the invention and the main technical problem of solving the invention are realized by adopting the following technical scheme: a germacrane type sesquiterpene Carpeschernolides A compound extracted from the herb of Ficus simplicissima, which is characterized in that: the germacrane type sesquiterpene Carpeschernolides A compound is separated and extracted from the herba Clausenae Lansii, and the structural formula is shown as the formula (I):
Figure BDA0001721367930000011
the preparation method comprises the steps of ethanol extraction, extract concentration, silica gel column chromatography, gradient elution and semi-preparative high performance liquid chromatography purification, and specifically comprises the following steps:
(1) taking 20kg of dry branches and leaves in the herba Centellae, performing reflux extraction for 3 times at 80 ℃ by adopting 95% industrial ethanol, recovering ethanol, concentrating to obtain an extract, mixing the extract with water to obtain a turbid substance, and performing equal-volume extraction and concentration by using ethyl acetate to obtain 0.960kg of ethyl acetate layer extract;
(2) subjecting the ethyl acetate layer extract to 300-sand 400-mesh silica gel column chromatography, performing gradient elution by using an eluent with the volume ratio of petroleum ether to acetone being 60: 1-0: 1, and combining point-thin layer plates into 7 parts: fr 1-7;
(3) performing MCI column chromatography on Fr 6 in the step (2), performing gradient elution by using an eluent with the volume ratio of methanol to water of 4: 6-10: 0, and dividing into 4 sub-parts: fr 6a, Fr 6b, Fr 6c and Fr 6d, Fr 6b are purified by semi-preparative high performance liquid chromatography to obtain the compound 1, wherein the mobile phase of the semi-preparative high performance liquid chromatography is acetonitrile to water in a volume ratio of 50: 50.
The tobacco pipe head is produced by Guizhou Zhenning.
The application of the germacrane sesquiterpene compound Carpescernolides A in preparing a medicament for treating liver cancer.
When the compounds are used as medicaments, they may be used separately 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 product adjuvants.
The pharmaceutical composition is used in the form of an amount to be administered per unit body weight.
The dosage form of the pharmaceutical composition comprises: injection, suspension, emulsion, solution, syrup, tablet, capsule, granule, spray, and aerosol.
The administration routes of the pharmaceutical composition for treating liver cancer comprise: intravenous injection, intravenous.
The invention discloses a gemmarane type sesquiterpene Carpeschernolides A compound which is extracted and separated from Bidens pinnatifida (Bidens pinnatifida) of Anshuzhen in Guizhou for the first time, the structural formula of the compound is determined, the compound has a treatment effect on cells of human liver cancer cells SMMC-7721, can induce apoptosis of the SMMC-7721 cells, promotes generation and accumulation of endogenous ROS in a dose-dependent manner, inhibits migration of tumor cells, inhibits formation of tumor cell clone, can be applied to preparation of a medicament for treating liver cancer, and can be used as a leading compound of the medicament for treating liver cancer.
Drawings
FIG. 1 is a formula of the structural formula (I) of the present invention.
FIG. 2 is a diagram corresponding to the present invention1H-NMR。
FIG. 3 is a diagram corresponding to the present invention13C-NMR。
FIG. 4 is a graph showing the effect of Carpescenolides A on the inhibition of SMMC-7721 cell viability.
FIG. 5 is a graph of the effect of Carpescernolides A on promoting the accumulation of ROS endogenous to SMMC-7721 cells.
FIG. 6 shows that Carpescenolides A inhibits the formation of SMMC-7721 cell clones.
FIG. 7 shows that Carpescenolides A inhibits migration of SMMC-7721 cells.
Detailed Description
Example 1:
(1) taking 20kg of dry branches and leaves in the herba Centellae, performing reflux extraction for 3 times at 80 ℃ by adopting 95% industrial ethanol, recovering ethanol, concentrating to obtain an extract, mixing the extract with water to obtain a turbid substance, and performing equal-volume extraction and concentration by using ethyl acetate to obtain 0.960kg of ethyl acetate layer extract;
(2) subjecting the ethyl acetate layer extract to 300-sand 400-mesh silica gel column chromatography, performing gradient elution by using an eluent with the volume ratio of petroleum ether to acetone being 60: 1-0: 1, and combining point-thin layer plates into 7 parts: fr 1-7;
(3) performing MCI column chromatography on Fr 6 in the step 2, performing gradient elution by using an eluent with the volume ratio of methanol to water of 4: 6-10: 0, and dividing into 4 sub-parts: fr 6a, Fr 6b, Fr 6c and Fr 6d, Fr 6b are purified by semi-preparative high performance liquid chromatography to obtain the compound 1, wherein the mobile phase of the semi-preparative high performance liquid chromatography is acetonitrile to water in a volume ratio of 50: 50.
Compound 1 data was analyzed using nuclear magnetic mass spectrometry as follows: colorless square crystals, m.p.306-308 ℃,
Figure BDA0001721367930000021
-286.98(c 0.00210g/ml,MeOH)，UV(MeOH)λmax(logε)195(0.30)nm,IR(KBr)vmax3426，29.57，1756，1632，1456，1099cm-1，HREIMS m/z 311.1488[M+H]+,calculated for C16H22O6,311.1489)，1H-NMR(400MHz,CDCl3)δ:1.25(1H,m,H-1β),2.01(1H,m,H-1α),4.39(1H,m,H-2),2.10(1H,dd,J＝2.0,11.6Hz,H-3β),2.56(1H,dd,J＝2.0,11.6Hz,H-3α),4.06(1H,s,H-5),1.86(1H,dd,J＝11.2,15.4Hz,H-9β),2.23(1H,dt,J＝1.2,15.4Hz,H-9α),1.72(1H,m,H-10),1.84(3H,s,H-13),0.93(3H,d,J＝5.6Hz,H-14),1.52(3H,s,H-15).13C NMR(100MHz,CDCl3)δ:45.06(C-1),77.97(C-2),50.45(C-3),86.53(C-4),83.39(C-5),106.17(C-6),156.39(C-7),104.02(C-8),51.08(C-9),27.86(C-10),129.82(C-11),174.20(C-12),10.60(C-13),26.50(C-14),27.29(C-15),52.89(C-OCH3). Structure thereof and corresponding1H-NMR，13C-NMR is shown in FIGS. 1 to 3.
And (3) tablet preparation: taking 10mg of the obtained gemma alkane type sesquiterpene Carpescenolides A, 180mg of lactose, 55mg of starch and 5mg of magnesium stearate;
the preparation method comprises the following steps: the compound, lactose and starch were mixed, uniformly moistened with water, the moistened mixture was sieved and dried, sieved again, magnesium stearate was added, and the mixture was compressed into tablets weighing 250mg each, the compound content being 10 mg.
Example 2:
an ampoule agent: carpescenolide A2 mg, sodium chloride 10mg, of the compound obtained in example 1;
the preparation method comprises the following steps: the compound and sodium chloride are dissolved in an appropriate amount of water for injection, and the resulting solution is filtered and filled into an ampoule under aseptic conditions.
Example 3:
and (3) capsule preparation: 10mg of Carpescenolide A obtained in example 1, 187mg of lactose, 3mg of magnesium stearate;
the preparation method comprises the following steps: mixing Carpescenolides A with adjuvants, sieving, mixing, and encapsulating the obtained mixture into hard gelatin capsules with weight of 200mg each and active ingredient content of 10 mg.
In order to further analyze that the germacrane type sesquiterpene Carpescenolides A has a therapeutic effect on cells of a human liver cancer cell line (SMMC-7721), can induce apoptosis of cells of the human liver cancer cell line (SMMC-7721) and is better used for preparing a medicament for treating liver cancer, the following experiment is carried out on the inhibition effect of the obtained germacrane type sesquiterpene Carpescenolides A on hepatoma cells SMMC-7721:
1. experimental materials:
96-well culture plate (NEST), DEME culture solution (BI), fetal bovine serum (BI), 0.25% Trypsin (Trypsin) is Hyclone product, tetramethyltetrazolium blue (3- (4, 5-dimethyltetrazolium-2-yl-tetrazolium bromide; MTT) is purchased from Sigma, dimethyl sulfoxide (DMSO) is Guangzhou chemical reagent, Allegra X-15R desktop centrifuge (Beckmann, USA), confocal microscope (GE Healthcare), TS100 binocular phase contrast biomicroscope (Nikon), microplate reader (Thermo), selected tumor cell strain is human hepatoma cell strain (SMMC-7721), drug is dissolved in DMSO to prepare a stock solution, and the stock solution is stored at-20 ℃ for later use.
SMMC-7721 is cultured in DMEM medium containing 10% fetal calf serum and mixed with 100U/mL penicillin and 100mg/mL streptomycin at 37 deg.C and 5% CO2 at constant temperature and saturated humidity. When the cell density reaches about 80%, passage is carried out, and the cells in the logarithmic growth phase are selected for experiment. Digesting tumor cells, transferring the tumor cells to a centrifuge tube, centrifuging the cells for 5min at 1000r/min, removing supernatant, adding a new culture solution, adding 5 multiplied by 104 cells into each hole of a 96-hole culture plate, respectively arranging 4 compound holes for each drug, arranging a blank group and a control group, culturing the cells overnight at 37 ℃ under 5% CO2 constant temperature saturated humidity, adding compounds with different concentrations for treatment, taking a DMSO treatment group as a negative control, continuously culturing the cells for 72h, adding MTT with the final concentration of 1mg/mL, incubating the cells for 4h, measuring the OD value by using a multifunctional microplate reader at 490 wavelength, and calculating IC 50. The inhibition rate of cell proliferation was calculated according to the following formula (this experiment was repeated 3 times):
growth inhibition (%) - (blank absorbance average-dosing absorbance average)/blank absorbance average × 100%
3. Experiment for inhibiting tumor cell clone formation
200 evenly dispersed SMMC-7721 cells are added into each well of a 6-well plate, and after overnight culture and cell adherence, compounds with different concentrations are added to treat the cells. After 16 days of incubation at 37C, when visible negative control colonies were evident, the medium was removed and 1mL of R250 dye was added. After staining for 1h at room temperature, the number of clones can be counted by taking a picture by washing with PBS three times.
Tanswell cell assay for in vitro invasion
SMMC-7721 cells were digested. After termination of digestion, the medium was discarded by centrifugation, (1-2 washes with PBS) and resuspended in serum-free medium. Cell density was adjusted to 5X 105/mL. 100L of cell suspension was taken and added to a Transwell chamber. The cells were cultured in a 37 ℃ cell culture chamber for 24 hours. Note that the cells should be seeded at the same time as the chamber is placed, avoiding seeding after placing the chamber in a sub-culture session. DMEM containing FBS is used as the lower layer culture solution, and DMEM without FBS is used as the culture solution in the small chamber. After overnight incubation, the Transwell chamber was removed, the medium from the wells was discarded, washed 2 times with calcium-free PBS and fixed in methanol for 15 minutes. Staining with Coomassie Brilliant blue R250 for 30min at room temperature. After that, the cells were washed 3 times with PBS, observed to migrate to the lower side of the membrane of the chamber, counted in five fields, upper, lower, left, right, and middle, respectively, and photographed for statistical data.
5. Test results
The results of FIGS. 4-7 show that Carpescenolides A can inhibit the activity of human hepatoma cell line (SMMC-7721) cells in a dose-dependent manner, promote the generation and accumulation of endogenous ROS in a dose-dependent manner, inhibit the migration of tumor cells, and inhibit the formation of tumor cell clones. And (5) drawing a conclusion that: the Carpescenolide A has strong inhibiting effect on human liver cancer cell strain (SMMC-7721) and can induce apoptosis of SMMC-7721 cells.
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. A germacrane type sesquiterpene compound extracted from the herba leonuri, which is characterized in that: the germacrane type sesquiterpene compound is named as Carpeschernolides A, is extracted and separated from the herba Clausenae Lansii, and has a structural formula shown as the formula (I):
Figure FDA0002591266930000011
the preparation method comprises the steps of ethanol extraction, extract concentration, silica gel column chromatography, gradient elution and semi-preparative high performance liquid chromatography purification, and specifically comprises the following steps:
(1) taking 20kg of dry branches and leaves in the herba Centellae, performing reflux extraction for 3 times at 80 ℃ by adopting 95% industrial ethanol, recovering ethanol, concentrating to obtain an extract, mixing the extract with water to obtain a turbid substance, and performing equal-volume extraction and concentration by using ethyl acetate to obtain 0.960kg of ethyl acetate layer extract;
(2) subjecting the ethyl acetate layer extract to 300-sand 400-mesh silica gel column chromatography, performing gradient elution by using an eluent with the volume ratio of petroleum ether to acetone being 60: 1-0: 1, and combining point-thin layer plates into 7 parts: fr 1-7;
(3) performing MCI column chromatography on Fr 6 in the step (2), performing gradient elution by using an eluent with the volume ratio of methanol to water of 4: 6-10: 0, and dividing into 4 sub-parts: fr 6a, Fr 6b, Fr 6c and Fr 6d, Fr 6b are purified by semi-preparative high performance liquid chromatography to obtain a compound 1, wherein the mobile phase of the semi-preparative high performance liquid chromatography is acetonitrile to water in a volume ratio of 50: 50; the structural formula of the compound 1 is shown as the formula (I).
2. The germacrane-type sesquiterpene compound extracted from the herb of centella asiatica according to claim 1, wherein: the tobacco pipe head is produced by Guizhou Zhenning.
3. The use of the germacrane-type sesquiterpene compounds extracted from the herb of Ficus simplicissima lour of claim 1, wherein: application in preparing medicine for treating liver cancer.
4. The use of the germacrane-type sesquiterpene compounds extracted from the herb of the genus Ribes nigrum of claim 3, wherein the extract comprises: 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.
5. The use of the germacrane-type sesquiterpene compounds extracted from the herb of Ficus simplicissima lour of 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 the germacrane-type sesquiterpene compounds extracted from the herb of Ficus simplicissima lour of claim 4, wherein: the pharmaceutical composition is used in the form of an amount to be administered per unit body weight.
7. The use of the germacrane-type sesquiterpene compounds extracted from the herb of Ficus simplicissima lour of claim 4, wherein: the dosage form of the pharmaceutical composition comprises: injection, suspension, emulsion, solution, syrup, tablet, capsule, granule, spray, and aerosol.
8. The use of the germacrane-type sesquiterpene compounds extracted from the herb of Ficus simplicissima lour of claim 4, wherein: the administration route of the pharmaceutical composition for treating the liver cancer is intravenous administration.
CN201810733042.4A 2018-07-06 2018-07-06 Gilmaxane type sesquiterpene compound extracted from herba Centellae and application thereof Expired - Fee Related CN108948040B (en)

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CN104945361A (en) * 2015-06-19 2015-09-30 中国医学科学院药用植物研究所 Germacrane sesquiterpenoid derivative and preparation method and application thereof
CN106117294A (en) * 2016-06-15 2016-11-16 安顺市人民医院 The Radix Kansui alkane type triterpenoid Phellochin F compound extracted in a kind of Cortex Phellodendri fruit and application thereof

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CN106117294A (en) * 2016-06-15 2016-11-16 安顺市人民医院 The Radix Kansui alkane type triterpenoid Phellochin F compound extracted in a kind of Cortex Phellodendri fruit and application thereof

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