CN109705188A - A kind of new triterpene compound and the preparation method and application thereof in pericarpium juglandis - Google Patents
A kind of new triterpene compound and the preparation method and application thereof in pericarpium juglandis Download PDFInfo
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Abstract
The invention discloses a kind of triterpenoids and its preparation method and application, belong to noval chemical compound and its medicinal usage.The methods of girard reagent processing, column chromatography are combined it is characterized in that extracting by organic solvent, extracting and developing purifies to obtain a kind of new triterpene compound from the fresh peel of pericarpium juglandisαCyclopentanone -21,22- a pair of horses going side by side closes 3,10- epoxy -5- hydroxyl-bis- ring of oleanane -19,22- [2,2,0]-hexane, is named as pericarpium juglandis triterpene ketone A.The compounds of this invention, which is verified by experiments, has preferable inhibition growth of tumour cell effect, the application prospect with anti-tumor aspect.
Description
Technical field
Present invention relates particularly to a kind of new triterpene compounds with inhibition of cancer cell effect.
Background technique
Malignant tumour is to endanger one of three big diseases of human health, morbidity and mortality with higher.Modern west
It cures and treats mainly based on chemotherapy, toxic side effect is larger, and patient survival quality is decreased obviously.Traditional Chinese medicine in anti-cancer and cancer-preventing, subtract
Few adverse reaction etc. has played unique advantage, is the treasure-house for researching and developing new type antineoplastic medicine.At present from Chinese herbal medicine
Anticancer agent, total 30% or more the anticarcinogen of Zhan, such as Japanese yew class, camptothecine, vincristine first choice antitumor as confrontation
Medicine.
Pericarpium juglandis is Juglandaceae walnut Juglans mandshuricaJuglands mandshuricaAnd walnut Maxim.J.ragiaL. the exocarp of immature fruit, on the civil basis that has been widely used in China, be commonly used for acute and chronic stomachache,
Borborygmus diarrhea, scabies etc..Modern pharmacological studies have shown that it has the effects that anti-inflammatory, analgesia, antibacterial and antitumor, it is especially anti-
Function of tumor is especially pronounced, is generally accepted by people.It is reported that pericarpium juglandis is to a variety of evils such as gastric cancer, lung cancer, liver cancer, cervical carcinoma
Property tumour have good curative effect, although the main component type having now been found that --- naphthoquinones class inhibit tumor growth effect
Significantly, but toxicity is big, and stability is poor, and as clinical application, there are biggish security risks.In order to make full use of the medicine resource,
This study group has carried on the chemical constitution study for going deep into system, it is therefore an objective to be screened out from it efficient, less toxic, stable drug effect
Material base.In to pericarpium juglandis triterpenes components separation process, a new triterpene ketone compounds are obtained, have been specified
Chemical structure, pharmacological activity and the purposes of the compound.
Summary of the invention
The object of the present invention is to provide a kind of new triterpene compounds and preparation method thereof and the noval chemical compound to make
Application in standby anti-tumor drug, solves the drawback that main anti-tumor active constituent toxicity is big, stability is poor in current pericarpium juglandis,
Expand the source of tumor.
New triterpene compound of the invention is that extracting and developing, purifying obtain from pericarpium juglandis, and chemical name isαRing penta
Ketone -21,22- a pair of horses going side by side closes 3,10- epoxy -5- hydroxyl-bis- ring of oleanane -19,22- [2,2,0]-hexane, and popular name is pericarpium juglandis three
Terpene ketone A.
Chemical structural formula are as follows:
The present invention also provides the preparation methods of pericarpium juglandis triterpene ketone A: using green peel of walnut as raw material, successively alcohol extracting, big
Hole resin concentration, girard reagent purification process and pillar layer separation etc. are prepared.
Above-mentioned column chromatography successively includes macroporous resin column, normal phase silicagel column, sephadex column.
Specific preparation process is as follows by pericarpium juglandis triterpene ketone A of the present invention:
(1) alcohol extracting: by Juglans mandshuricaJuglans mandshurica40 DEG C of low temperature of Maxim Chinese olive skin fresh goods drying, obtain 5kg's
Dry product is raw material, and using 95% ethyl alcohol 30L refluxing extraction 3 times, each 2h filters and merge ethanol extract, is recovered under reduced pressure molten
Agent, it is dry, obtain ethanol extract；
(2) enriching and purifying: by medicinal extract extract obtained by step (1) it is water-dispersible to relative density be the molten of 1.18 ± 0.05g/mL
Liquid is successively eluted with water, 50% ethyl alcohol, 80% ethyl alcohol respectively through AB-8 or D101 type macroporous resin column chromatography enriching and purifying, is collected
80% ethanol eluate, is recovered under reduced pressure ethyl alcohol, is adjusted to the aqueous solution that density is 1.05g/mL.Aqueous passes through active carbon layer 5 times repeatedly
(layer high 10cm, diameter 30cm) carry out decompression filter removal of impurities, then by aqueous concentration be evaporated after, be separately added into dehydrated alcohol, Ji La
Moral reagent P and 12%(V/V) acetic acid pinch molten, then 50 DEG C of warm 10h of water-bath, and it is diluted with water after reaction, same volume is added
Ether extracts three times, obtains ether medicinal extract；
(3) normal phase silica gel column chromatography: taking ether medicinal extract obtained by step (2) to carry out normal phase silica gel column chromatography separation, successively uses body
Product elutes 3 column volumes than the methylene chloride-methanol mixed solvent gradient elution for 50:1,25:1,15:1, each ratio,
The methylene chloride-methanol mixed solvent elution fraction that wherein volume proportion is 15:1 is recovered under reduced pressure solvent and obtains separation product；
(4) sephadex post separation: the product after step of learning from else's experience (3) separation, by sephadex column, with methanol: water=1:
2(V/V) elute 3 column volumes to discard, again with methanol: water=1:1(V/V) 4 column volumes of elution, it discards first column volume and washes
De- liquid, three column volume eluents, recycling design obtain crude product below for collection；
(5) recrystallization is handled: twice using recrystallizing methanol by crude product obtained by step (4), the pure compounds can be obtained.
The present invention also provides application of the pericarpium juglandis triterpene ketone A in terms of preparing anti-tumor drug.Cell toxicant is real in vitro
It is able to suppress the proliferation of human gastric cancer cells BGC-823, human liver cancer cell HepG-2, human lung cancer cell A549 in testing, there is cell
Toxic action can be used as the application that preparation prevents and treats human gastric cancer, liver cancer and lung-cancer medicament.
Beneficial effects of the present invention and meaning are:, can be efficient by combining girard reagent preconditioning technique
Carbonyl material in purifying and enrichment pericarpium juglandis medicinal material, other kinds of impurity is to such during overcoming traditional solvent extraction
Ingredient interference is big, causes the application limitation that its yield is low；And the present invention searches out the triterpenes with special construction framework characteristic
Compound also provides important effective substance source for further antitumor clinical research.
Detailed description of the invention
Fig. 1 is the chemical structural formula of the compounds of this invention；
Fig. 2 is the positivity HR-ESI-MS spectrogram of the compounds of this invention；
Fig. 3 is the compounds of this invention1H-NMR spectrum；
Fig. 4 is the compounds of this invention13C-NMR spectrogram；
Fig. 5 is the DEPT spectrogram of the compounds of this invention；
Fig. 6 is the hsqc spectrum figure of the compounds of this invention；
Fig. 7 is the HMBC spectrogram of the compounds of this invention；
Fig. 8 is the compounds of this invention1H-1H COSY spectrogram；
Fig. 9 be the compounds of this invention HMBC spectrum and1H-1H COSY composes main correlativity figure；
Figure 10 is the compounds of this invention and cis-platinum to three kinds of different type cancer cell IC50Value compares.
Specific embodiment
Disclosed technology contents, those skilled in the art will be apparent that other embodiments of the invention according to the present invention,
Following embodiments only make example.In the case where not violating present subject matter and range, various adjustment can be carried out to the present invention
And improvement.These variations should be within the scope of the present invention.The present invention is described in detail combined with specific embodiments below.
The preparation method of one the compounds of this invention of case study on implementation:
(1) alcohol extracting: by Juglans mandshuricaJuglans mandshurica40 DEG C of low temperature of Maxim Chinese olive skin fresh goods drying, obtain 5kg's
Dry product is raw material, and using 95% ethyl alcohol 30L refluxing extraction 3 times, each 2h filters and merge ethanol extract, is recovered under reduced pressure molten
Agent, it is dry, obtain ethanol extract 328g；
(2) enriching and purifying: by medicinal extract extract obtained by step (1) it is water-dispersible to relative density be the molten of 1.18 ± 0.05g/mL
Liquid, through AB-8 or D101 type macroporous resin column chromatography enriching and purifying, (chromatographic column specification is internal diameter × length=6.5cm × 1.5m, tree
Rouge effective height m), is successively eluted with water, 50% ethyl alcohol, 80% ethyl alcohol respectively for 1.0, is collected 80% ethanol eluate, is depressurized back
Ethyl alcohol is received, the aqueous solution that density is 1.05g/mL is adjusted to, aqueous passes through active carbon layer (layer high 10cm, diameter 30cm) 5 times repeatedly
Carry out decompression filter removal of impurities, then by aqueous concentration be evaporated after, be separately added into dehydrated alcohol, girard reagent P and 12%(V/V) vinegar
Acid pinch molten, then 50 DEG C of warm 10h of water-bath, is diluted with water after reaction, and the extraction of same volume ether is added three times, obtains second
25.8 g of ethereal extract；
(3) normal phase silica gel column chromatography: ether medicinal extract obtained by step (2) is taken to carry out normal phase silica gel column chromatography separation (chromatographic column specification
For internal diameter × length=3.0cm × 1.5m, silica gel effective height 1.0m), methylene chloride-methanol (50:1, V/V, 3 column is successively used
Volume) → methylene chloride-methanol (25:1, V/V, 3 column volume) → methylene chloride-methanol (15:1, V/V, 3 column volume) is
Solvent is recovered under reduced pressure extremely in the mixed solvent elution fraction that wherein methylene chloride-methanol volume proportion is 15:1 by system gradient elution
Dry, weighing obtains separation product 1.26g；
(4) sephadex post separation: the product after the separation of step of learning from else's experience (3) silica gel, by sephadex column, (chromatographic column is advised
Lattice are internal diameter × length=1.5cm × 1.8m, and gel effective height is 1.2 m), with methanol: water=1:2(V/V) 3 cylinders of elution
Product discards, again with methanol: water=1:1(V/V) 4 column volumes of elution, first column volume eluent is discarded, collects three below
Column volume eluent, recycling design obtain crude product 0.06g to doing；
(5) recrystallization is handled: twice using 30mL recrystallizing methanol by crude product obtained by step (4), it is pure that the compound can be obtained
Product 35.5mg.
The Structural Identification of two the compounds of this invention of case study on implementation:
The compounds of this invention is white amorphous powder (MeOH).In positivity HR-ESI-MS spectrum, as shown in Fig. 2,m/z
494.3498 locating visible [M]+Quasi-molecular ions shows that the molecular weight of the compound is 494.In conjunction with1H-NMR、13C-NMR and DEPT spectrum
Deng supposition, its molecular formula is C33H50O3, calculating its degree of unsaturation is 9.
In the compound1H-NMR (Methanol-d 4, 400MHz) and spectrum, as shown in Figure 1, display 8 methyl protons point
It is notδ H 0.92 (H-26)、0.96 (H-26)、1.04 (H-30)、1.05 (H-27)、1.07 (H-29)、1.12 (H-
24), 1.15 (H-28) and 1.15 (H-23), a methine proton signal being connected with oxygen existδ H3.67 (H-3)。13C-
NMR (Methanol-d 4, 100MHz) and it composes in conjunction in DEPT spectrum, as shown in Figure 4, Figure 5, show 33 carbon signals, including 8
A methyl, 10 methylene, 5 methines, 10 quaternary carbons (wherein comprising 2 oxygen-containing quaternary carbons and 1 carbonyl).
In the HMBC spectrum of the compound, as shown in fig. 7, can obviously observe that 3,24 and 25 constitute3 JIt is remote
Cheng Xiangguan, illustrate hydroxyl on 5, and C-5 and C-4, C-6, C-10 and the compound separated from Kleinia odora
Almost the same (Tori M, Matsuda R, Sono M, the Asakawa Y. 1988. of the spectral data of klodorol A13C
NMR assignment of dammarane triterpenes and dendropanoxide:application of 2D
long-range 13C–lH correlation spectra. Magn Reson Chem. 26:581–590. Estrada S,
Acevedo L, Rodriguez M, Toscano R, Mata R. 2002. New triterpenoids from the
Orchids Scaphyglottis livida and Nidema boothii. Nat Prod Res. 16:81-86.), it says
The bright hydroxyl isαConfiguration.Only part chemical structure is similar to known compound klodorol A for compound in the present invention, the two
There are obvious othernesses for E, F ring.HMBC spectrum in, can be observed and H-18, H-29, H-30 there are the C- of correlativity
19, and changed with the type of the relevant C-22 of H-21, H-28, H-32, H-33, it is changed into respectively by original secondary carbon
Thus tertiary carbon and quaternary carbon speculate that there are C -- C single bonds between C-19 and C-22.Exist simultaneously1H-1In H COSY spectrum, as shown in figure 8, can
Observe 33δ H1.94 and 32δ H2.48 is related, and illustrating 32,33, there are ethyl segments, and have carbonylδ C 220.1 and upper
It states segment and there is long-range correlation, thus it is speculated that the compound presence-CH2-CH2- C=O structure, and with 21,22 form five yuan of F ring,
It is particularly relevant to see Fig. 9.To sum up, the chemical structure of the compounds of this invention is determined asαCyclopentanone -21,22- a pair of horses going side by side closes 3,10- epoxy -
5- hydroxyl-bis- ring of oleanane -19,22- [2,2,0]-hexane, i.e. pericarpium juglandis triterpene ketone A, chemical structural formula are as shown in Figure 1.
1 the compounds of this invention NMR signal of table ownership
Effect example --- extracorporeal suppression tumor cell proliferation function
(1) material and method
1) cell line and reagent Human gastric carcinoma cell line BGC-823, human hepatoma cell strain HepG-2, human lung carcinoma cell line A549 are thin
Born of the same parents' strain, above-mentioned tumor strain are purchased from Sai Er Reagent Company.These above-mentioned tumour cells are placed in the tire ox blood containing 10% L-Glutamine
(separately contain 100 μ g/mL penicillin, 100 μ g/mL streptomysins) in clear RPMI 1640 culture medium, is saturated in 37 DEG C, 5% wet
The CO of degree2It is cultivated in incubator.What the compounds of this invention was obtained from the preparation of case study on implementation one.
2) BGC-823, HepG-2, A549 cell of analysis of cell proliferation logarithmic growth phase, according to the difference of cell strain
It is inoculated in 96 orifice plates by certain density, every hole is the cell suspension of 100 μ L, and various concentration drug is added immediately after inoculating cell
(sample is dissolved in DMSO, is gradually diluted with culture medium, and the DMSO final concentration of cell Chinese medicine liquid is added lower than 1%), makes cell liquid
Final concentration reaches 5,10,20,40,80,160 μM, and the RPMI1640 that blank control group is 100 μ L adds 10 μ L without the conduct pair of medicine solvent
According to group, every group sets 3 multiple holes；After being incubated for 48 h, the 20 μ L of MTT of 5mg/mL is added in every hole, and 37 DEG C are continued to be centrifuged after cultivating 4 h
(2000 rpm, 10 min) carefully suck supernatant, and every hole is added 150 μ L DMSO and mixes, and each group is surveyed at 570nm wavelength
The OD value in fixed every hole calculates inhibitory rate of cell growth only to add the hole DMSO as zeroing hole.Inhibitory rate of cell growth %=[1- (drug
Handle hole mean OD value-zeroing hole OD value)/(cell control well mean OD value-zeroing hole OD value)] × 100%.Use Logit method
Calculate the IC of drug50Value.
(2) result
Linear recurrence calculates IC50Value shows the compound to human gastric cancer, human liver cancer cell HepG-2 and people
Lung cell A549 cytosis IC50Value is respectively 52.96 ± 4.22 μM, 32.15 ± 3.19 μM and 22.95 ± 2.19 μM, suitable
Platinum is as positive control drug to human gastric cancer, human liver cancer cell HepG-2 and human lung cancer cell A549's cytosis
IC50Value is respectively 6.23 ± 1.08 μM, 4.88 ± 0.59 μM and 5.12 ± 2.02 μM, sees Figure 10.
The result shows that the compounds of this invention is to human gastric cancer, human liver cancer cell HepG-2, human lung carcinoma cell
The growth of A549 cell all has a strong inhibitory effect, and has the prospect that clinical tumor prevents and treats drug for preparing.
Claims (4)
1. a kind of triterpenoid and preparation method thereof and anticancer usage, it is characterised in that chemical name are as follows:αCyclopentanone -21,
22- a pair of horses going side by side closes 3,10- epoxy -5- hydroxyl-bis- ring of oleanane -19,22- [2,2,0]-hexane, is named as pericarpium juglandis triterpene ketone A,
With chemical structural formula are as follows:
。
2. the preparation method of compound pericarpium juglandis triterpene ketone A described in claim 1, it is characterised in that: using green peel of walnut as raw material,
By alcohol extracting → macroporous resin enrichment → girard reagent purification process → ether extraction, extract is again through column chromatography repeatedly point
From isolating and purifying to obtain the compound with recrystallization means.
3. preparation method according to claim 2, it is characterised in that: macroreticular resin model is AB-8 or D101；Gerald
Reagent selects girard reagent P, and column chromatography carrier is selected from purification on normal-phase silica gel, sephadex Sephadex LH-20, specific to make
It is standby that steps are as follows:
(1) alcohol extracting: by Juglans mandshuricaJuglans mandshurica40 DEG C of low temperature of Maxim Chinese olive skin fresh goods drying, obtain 5kg's
Dry product is raw material, and using 95% ethyl alcohol 30L refluxing extraction 3 times, each 2h filters and merge ethanol extract, is recovered under reduced pressure molten
Agent, it is dry, obtain ethanol extract；
(2) enriching and purifying: by medicinal extract extract obtained by step (1) it is water-dispersible to relative density be the molten of 1.18 ± 0.05g/mL
Liquid is successively eluted with water, 50% ethyl alcohol, 80% ethyl alcohol respectively through AB-8 or D101 type macroporous resin column chromatography enriching and purifying, is collected
80% ethanol eluate, is recovered under reduced pressure ethyl alcohol, is adjusted to the aqueous solution that density is 1.05g/mL；Aqueous passes through active carbon layer 5 times repeatedly
(layer high 10cm, diameter 30cm) carry out decompression filter removal of impurities, then by aqueous concentration be evaporated after, be separately added into dehydrated alcohol, Ji La
Moral reagent P and 12%(V/V) acetic acid pinch molten, and it in 50 DEG C of warm 10h of water-bath, is diluted with water after reaction, same volume is added
Ether extracts three times, obtains ether medicinal extract；
(3) normal phase silica gel column chromatography: taking ether medicinal extract obtained by step (2) to carry out normal phase silica gel column chromatography separation, successively uses body
Product elutes 3 column volumes than the methylene chloride-methanol mixed solvent gradient elution for 50:1,25:1,15:1, each ratio,
The methylene chloride-methanol mixed solvent elution fraction that wherein volume proportion is 15:1 is recovered under reduced pressure solvent and obtains separation product；
(4) sephadex post separation: the product after step of learning from else's experience (3) separation, by sephadex column, with methanol: water=1:
2(V/V) elute 3 column volumes to discard, again with methanol: water=1:1(V/V) 4 column volumes of elution, it discards first column volume and washes
De- liquid, three column volume eluents, recycling design obtain crude product below for collection；
(5) recrystallization is handled: twice using recrystallizing methanol by crude product obtained by step (4), the pure compounds can be obtained.
4. compound pericarpium juglandis triterpene ketone A is in the application in terms of preparing anti-tumor drug described in claim 1.
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Cited By (4)
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| CN111087441A (en) * | 2020-01-08 | 2020-05-01 | 黑龙江中医药大学 | Preparation method and application of novel triterpene compound in walnut green husk |
| CN113499361A (en) * | 2021-07-28 | 2021-10-15 | 西北农林科技大学 | Method for extracting terpenoid substances in walnut green seedcase |
| CN114835568A (en) * | 2022-04-20 | 2022-08-02 | 黑龙江中医药大学 | Preparation method and application of biphenyl diaryl heptane in walnut green seedcase |
| CN114835668A (en) * | 2022-04-20 | 2022-08-02 | 黑龙江中医药大学 | Preparation method and application of cyclic ether type diaryl heptane in exocarpium Juglandis Immaturum |
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Cited By (6)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN111087441A (en) * | 2020-01-08 | 2020-05-01 | 黑龙江中医药大学 | Preparation method and application of novel triterpene compound in walnut green husk |
| CN111087441B (en) * | 2020-01-08 | 2021-06-22 | 黑龙江中医药大学 | Preparation method and application of triterpene compound in walnut green husk |
| CN113499361A (en) * | 2021-07-28 | 2021-10-15 | 西北农林科技大学 | Method for extracting terpenoid substances in walnut green seedcase |
| CN114835568A (en) * | 2022-04-20 | 2022-08-02 | 黑龙江中医药大学 | Preparation method and application of biphenyl diaryl heptane in walnut green seedcase |
| CN114835668A (en) * | 2022-04-20 | 2022-08-02 | 黑龙江中医药大学 | Preparation method and application of cyclic ether type diaryl heptane in exocarpium Juglandis Immaturum |
| CN114835668B (en) * | 2022-04-20 | 2023-12-19 | 黑龙江中医药大学 | Preparation method and application of cyclic ether diaryl heptane in green dragon clothes |
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