CN109438195A - A kind of new naphthalene compounds and preparation method thereof - Google Patents
A kind of new naphthalene compounds and preparation method thereof Download PDFInfo
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Abstract
The invention discloses a kind of naphthalene compounds and preparation method thereof, the compound is isolated from the fresh bamboo sap that gramineae plant moso bamboo prepares through destructive distillation, referred to as fresh bamboo sap element A, and through superconduction NMR spectrum, the detection of the multiple means such as mass spectrum determines its C20H20O6Molecular weight is 356, chemical structural formula is formula (I), the present invention has carried out external activity screening to fresh bamboo sap element A, the result shows that the compound has apparent inhibiting effect to gastric carcinoma cells and human colon cancer cell, it can be used as the lead compound of the anti-tumor drug of development of new, also can be used as the drug developed and treat the various common multiple cancers of clinic.
Description
Technical field
The present invention relates to pharmaceutical technology field, in particular to a kind of one kind isolated and purified from fresh bamboo sap it is new to
Naphthalene compounds fresh bamboo sap element A and preparation method thereof.Above compound significantly inhibits tumor cell line, can
As the lead compound for developing new anti-tumor drug, the medicine developed and treat the various common multiple cancers of clinic can also be used as
Object.
Background technique
Fresh bamboo sap is gramineae plant phyllostachys glauca McClure (Phyllostachys glauca McCluve), net bamboo
The liquid leached naturally after (Phyllostachys nuda McClure) and the fresh pole for belonging to several plants are heated, boils
Afterwards, appropriate preservative is added to be made.There is the effect of clearing heat and eliminating phlegm, be used for cough with lung heat's abundant expectoration, pant uncomfortable in chest, apoplexy tongue is strong, small
The hot infantile convulsion of youngster's phlegm, for the key medicine for treating cough with lung heat.Fresh bamboo sap is curative for effect as a kind of traditional antibechic, eliminating the phlegm Chinese medicine, most
It early records in " Chinese Pharmacopoeia " version in 1977, because its cultivar origin is unstable, the reasons such as material base is indefinite cause its quality
Standard is difficult to formulate, and version in 1985 later " Chinese Pharmacopoeia " is not recorded individually using fresh bamboo sap as medicinal material.Fresh bamboo sap at present
Record in 1992 version " Drug Standard of Ministry of Public Health of the Peoples Republic of China " Chinese medicine first, only 1 ammonia under the normal term
Base acid thin layer identifies and pH value, total solid, relative density check item.
Modern research shows that mainly contained in fresh bamboo sap amino acids, phenolic constituent, inorganic elements and organic acid at
Point.Currently, the compound separated from fresh bamboo sap mainly has: przewaquinone A, Przewatanshinquinone B, guaiacol,
Remove first silk floss cresols etc..
The present invention studies the ingredient of fresh bamboo sap, obtains a variety of new compounds by isolating and purifying, therein
One naphthalene compounds is the naphthalene compounds that separation and Extraction obtains from fresh bamboo sap for the first time, is not appeared in the newspapers in existing document
Road, Kaiho A., et al.Green Chem., 2016,18 (24), 6526-6535, the document discloses a kind of and present invention
The compound a nnulated HV of compound similar structures, but the structure of the compound is in terms of benzene the position of substitution and the present inventionization
Closing object has larger difference, and the present invention has made intensive studies the compound for this, in terms of existing technologies, the chemical combination
Object has the more obvious antitumor action better than the prior art, while reducing side effect, can be in preparation treating cancer
Or it is applied in the drug of tumour.
Summary of the invention
Goal of the invention:
It is an object of the present invention to provide extract to obtain a new naphthalene compounds fresh bamboo sap element from fresh bamboo sap
A。
It is a further object to provide the preparation methods of above-mentioned naphthalenes noval chemical compound fresh bamboo sap element A.
A further object of the present invention is to provide above-mentioned naphthalene compounds fresh bamboo sap element A in preparation cancer and/or antitumor
Application in drug.
Technical solution: the present inventor has done further research again on the basis of existing technology, finds Jiangxi Province Yichuan
The active constituent of its anticancer is mainly the compound in the present invention in the fresh bamboo sap for the moso bamboo that is produced from city, and is gone back at present through data consultation
There is no treatment of the document report fresh bamboo sap element A for cancer and/or tumour.
For this purpose, the present invention provides the naphthalene compounds fresh bamboo sap element A or its pharmaceutically acceptable salt of a kind of structure formula (I)
The wherein pharmaceutically acceptable salt, naphthalene compounds fresh bamboo sap element A selected from structure formula (I) and inorganic acid,
The salt that organic acid is formed, or the salt formed with alkali metal, alkaline-earth metal.
The preparation step of naphthalene compounds fresh bamboo sap element A is successively as follows:
(1) destructive distillation is extracted: after moso bamboo cutting, obtaining fresh bamboo sap through destructive distillation；
(2) medicinal extract concentrated extracting solution: is concentrated under reduced pressure to obtain in fresh bamboo sap；
(3) it extracts: taking fresh bamboo sap medicinal extract (37.8kg), purified water 40L is added to dissolve, then extract three with 160L ethyl acetate
It is secondary, acetic acid ethyl acetate extract；
(4) acetic acid ethyl acetate extract is concentrated: acetic acid ethyl acetate extract being concentrated under reduced pressure, ethyl acetate extract (310g) is obtained；
(5) column chromatography for separation: after ethyl acetate extract is dissolved with proper amount of methanol, with 1: 1.5 silica gel mixed sample, sample is dry
Method is packed into silica gel column chromatography (internal diameter 14cm, pillar height 90cm, 100~200 mesh of column filling gel granularity), with chloroform-methanol
(15:1) is elution 3h, and eluent is collected with every part of 3L, collects 49 parts altogether, is concentrated to dryness respectively, is passed through
Thin layer detection, merges 18-28 parts of eluting fractions (111.9 g), and by itself and 120g silica gel mixed sample, sample wet process is packed into layer of silica gel
Analyse column (internal diameter 10cm, pillar height 124cm, 100~200 mesh of column filling gel granularity), with chloroform-methanol (80:1~20:
1) 8 h of gradient elution, every part is collected by 2L, is collected 145 parts altogether, is inspected through thin-layer chromatography, is merged 50-57 parts of elutions and is evaporated
Divide (23g), above-mentioned fraction is through C18Middle pressure reversed phase column chromatography (40cm × 7cm, 5 μm), with methanol-water (32:68~86:14) gradient
It elutes (20ml/ minutes), every part is collected by 400mL, is collected 79 parts altogether, is inspected through thin-layer chromatography, is merged 27-30 parts and is washed
De- fraction (20mg), the fraction are fresh bamboo sap element A crude product.
(6) purifying of monomeric compound: fresh bamboo sap element A crude product inverted high performance preparative liquid chromatography (chromatographic column: C18 5μ
M, 250mm × 20mm, Detection wavelength: 210nm), with methanol-water (55: 45, v/v, 7mL/min) for eluent, through preparation solution
Mutually preparation at 146min fresh bamboo sap element A (6mg) of the invention.Fresh bamboo sap element A is through high performance liquid chromatography detection, chromatographic condition
For chromatographic column: C18(250mm × 4.6mm, 5 μm)；Mobile phase: methanol-water (55: 45)；Detection wavelength: 210nm；Column temperature: 30
℃；Sample volume: 10 μ l.It is calculated through area normalization method, fresh bamboo sap element A purity >=99%.
Wherein, eluant, eluent is chloroform-methanol, chloroform and methanol volume proportion in step (5) are as follows: 25: 1 or 10: 1 or 8: 1
Or 7: 1 or 5: 1；Gradient elution agent is methanol-water, and methanol volumetric concentration is 20%~80%.
Wherein, eluant, eluent is methanol-water in step (6), and methanol and water volume concentration are 40%~70%.
The present invention further provides naphthalene compounds fresh bamboo sap element A or its pharmaceutically acceptable salt to prepare antineoplastic
Application in object.The tumour is selected from: gastric cancer, liver cancer, colon cancer, bladder cancer.
The invention also includes containing naphthalene compounds fresh bamboo sap element A of the present invention or its pharmaceutically acceptable salt
Pharmaceutical composition.The pharmaceutical composition, wherein further including pharmaceutically acceptable carrier.Described pharmaceutical composition is to be suitble to medicine
Dosage form, the pharmaceutical formulation are selected from: tablet, capsule, granule, pill, powder, paste, suspension, injection
Agent, suppository, drops, pill, oral solution, patch.
Product of the present invention is detected through multiple means such as superconduction NMR spectrum, mass spectrums, it is determined that point of fresh bamboo sap element A
Minor C20H20O6, molecular weight 356, chemical structure are formula (I).
The present invention produces in fresh bamboo sap prepared by moso bamboo from Jiangxi Province's Yichun City and extracts an isolated new naphthalenes for the first time
Compound, entitled fresh bamboo sap element A, entitled 8- (4- hydroxyl -3,5- Dimethoxyphenyl) -2, the 4- dimethoxy -3- naphthalene of chemistry
Phenol, fresh bamboo sap element A are white powder, are soluble in the organic reagents such as acetone, propylene glycol, pyridine, methanol, and fusing point is 192-193 DEG C,
UV (CH3OH) λ max 204nm and 295nm.
Test proves fresh bamboo sap element A 1 × 10-8mol/L→1×10-5To gastric carcinoma cells and human colon carcinoma when mol/L
Cell has apparent inhibiting effect, and IC50 is respectively 2.5 μM and 2.9 μM.
Detailed description of the invention
Fig. 1 is the preparation process flow schematic diagram of fresh bamboo sap element A, the Detailed description of the invention preparation step of fresh bamboo sap element A are as follows:
(1) destructive distillation is extracted；(2) concentrated extracting solution；(3) ethyl acetate, n-butanol successively extract；(4) acetic acid ethyl acetate extract is concentrated；
(5) column chromatography for separation；(6) it purifies.
Fig. 2 is high resolution mass spectrum figure, illustrates the molecular weight of fresh bamboo sap element A；
Fig. 3 is nuclear magnetic resonance1H NMR spectra illustrates hydrogen (- C=C-H ,-OCH in fresh bamboo sap element A structure3Deng) return
Belong to；
Fig. 4 is nuclear magnetic resonance13C NMR spectra illustrates carbon (- C=C- ,-OCH in fresh bamboo sap element A structure3Deng) return
Belong to；
Fig. 5 is nuclear magnetic resonance hsqc spectrum figure, illustrates the ownership of relevant carbon and hydrogen in fresh bamboo sap element A structure；
Fig. 6 is nuclear magnetic resonance HMBC spectrogram, illustrates the position of methoxyl group and fragrant hydrogen in fresh bamboo sap element A structure；
Specific embodiment
Below with reference to embodiment, the present invention is further elaborated.The following embodiments of mandatory declaration are for illustrating the present invention
Rather than limiting the invention.Essence according to the present invention belongs to that the present invention claims guarantors to the simple modifications that carry out of the present invention
The range of shield.
2010 series of high efficiency liquid chromatograph of Shimadzu (Japanese Shimadzu Corporation), hydraulic fluid phase preparative chromatograph (Switzerland in BUCHi
BUCHI Labortechnik AG), Waters series of high efficiency liquid chromatograph (including Waters 600 Control, PAA2996 type diode battle array
Column detector, 717 Plus autosampler of Waters, Empower chem workstation) (Waters, US), Agilent
1200 type, half preparative high-performance liquid chromatographic instrument, Sartoris BP211A type electronic balance (German Sai Tuolisi group), EYELA
SB-1000 Rotary Evaporators (Japanese EYELA company), electric-heated thermostatic water bath (Shanghai leap medical apparatus and instruments factory), UV-260 points
Light photometer (Japanese Shimadzu Corporation), 600 NMR spectrometer with superconducting magnet of Varian UNITY INOVA (Varian company, the U.S.),
Xevo G2Q-Tof time of-flight mass spectrometer (Waters, US), (U.S. AKSH is public for Autopol IV-T/V polarimeter
Department), RY-1G melting point detector (Chinese Tianjin daylight optical instrument Co., Ltd), C18Reverse phase filler is YMC production, column chromatography
Silica gel, tlc silica gel are Haiyang Chemical Plant, Qingdao's production.
Methanol is chromatographically pure, and water is Wahaha Pure Water, other reagents are that analysis is pure.
Embodiment 1: the extraction separation method of naphthalene compounds fresh bamboo sap element A in fresh bamboo sap:
Moso bamboo picks up from Jiangxi Province Yichun City Tonggu County, reflects through Tonggu County Wei Sheng Industrial Co., Ltd. Wu Ziping senior experimentalist
It is set to the fresh bar stem of grass family Phyllostachys plant moso bamboo Phyllostachys edulis (Carr.) H.de Lehaie.Sample
It is retained in Jiangxi Province's drug inspection detection research institute's Specimen Room.
The preparation step of fresh bamboo sap element A is successively as follows:
(1) destructive distillation is extracted: after moso bamboo cutting, obtaining fresh bamboo sap through destructive distillation；
(2) medicinal extract concentrated extracting solution: is concentrated under reduced pressure to obtain in fresh bamboo sap；
(3) it extracts: taking fresh bamboo sap medicinal extract (37.8kg), purified water 40L is added to dissolve, then extract three with 160L ethyl acetate
It is secondary, acetic acid ethyl acetate extract；
(4) acetic acid ethyl acetate extract is concentrated: acetic acid ethyl acetate extract being concentrated under reduced pressure, ethyl acetate extract (310g) is obtained；
(5) column chromatography for separation: after ethyl acetate extract is dissolved with proper amount of methanol, with 1: 1.5 silica gel mixed sample, sample is dry
Method is packed into silica gel column chromatography (internal diameter 14cm, pillar height 90cm, 100~200 mesh of column filling gel granularity), with chloroform-methanol
(15:1) is elution 3h, and eluent is collected with every part of 3L, collects 49 parts altogether, is concentrated to dryness respectively, is passed through
Thin layer detection, merges 18-28 parts of eluting fractions (111.9 g), and by itself and 120g silica gel mixed sample, sample wet process is packed into layer of silica gel
Analyse column (internal diameter 10cm, pillar height 124cm, 100~200 mesh of column filling gel granularity), with chloroform-methanol (80:1~20:
1) 8 h of gradient elution, every part is collected by 2L, is collected 145 parts altogether, is inspected through thin-layer chromatography, is merged 50-57 parts of elutions and is evaporated
Divide (23g), above-mentioned fraction is through C18Middle pressure reversed phase column chromatography (40cm × 7cm, 5 μm), with methanol-water (32:68~86:14) gradient
It elutes (20ml/ minutes), every part is collected by 400mL, is collected 79 parts altogether, is inspected through thin-layer chromatography, is merged 27-30 parts and is washed
De- fraction (20mg), the fraction are fresh bamboo sap element A crude product.
(6) purifying of monomeric compound: fresh bamboo sap element A crude product inverted high performance preparative liquid chromatography (chromatographic column: C18 5μ
M, 250mm × 20mm, Detection wavelength: 210nm), with methanol-water (55: 45, v/v, 7mL/min) for eluent, through preparation solution
Mutually preparation at 146min fresh bamboo sap element A (6mg) of the invention.Fresh bamboo sap element A is through high performance liquid chromatography detection, chromatographic condition
For chromatographic column: C18(250mm × 4.6mm, 5 μm)；Mobile phase: methanol-water (55: 45)；Detection wavelength: 210nm；Column temperature: 30
℃；Sample volume: 10 μ l.It is calculated through area normalization method, fresh bamboo sap element A purity >=99%.
Embodiment 2: naphthalene compounds fresh bamboo sap element A Structural Identification
The physicochemical property of fresh bamboo sap element A is as follows: white powder is soluble in organic examination such as acetone, propylene glycol, pyridine, methanol
Agent, fusing point are 192~193 DEG C, UV (CH3OH)λmax204nm and 295nm.Ultra performance liquid chromatography-quadrupole rod-flight time
Mass spectrum provides quasi-molecular ion peak m/z 355.1164 [M-H]— (calcd for C20H19O6, 355.1182), in conjunction with1H-
NMR and13C-NMR, which is composed, determines that its molecular formula is C20H20O6。1H with13C NMR data is shown in Table 1, meanwhile, pass through measurement two dimension H-C
Correlated Spectroscopy (HSQC), the long-range Correlated Spectroscopy of H-C (HMBC), it is determined that the signals assignment and the chemical combination of all carbon atoms and hydrogen atom
The chemical structure of object.Chemical structural formula is as follows:
The hydrogen spectrum and carbon modal data table (δ in ppm, J in Hz) of 1 fresh bamboo sap element A of table
Note: INOVA 600MHz；δ chemical shift unit ppm,1H-NMR and13C-NMR test solvent is DMSO；Nuclear-magnetism is total
The ownership of vibration signal is completed on the basis of HSQC, HMBC two-dimensional spectrum.
Embodiment 3: the anti tumor activity in vitro test of naphthalene compounds fresh bamboo sap element A
Growth of tumour cell inhibiting rate (%)=(1- experimental port measured value/control wells measured value) × 100%
Test philosophy: mtt assay: in the mitochondria of living cells there is with NAAP (nicotinamide-adenine dinucleotide phosphate,
Codehydrogenase Ⅱ) relevant dehydrogenase, it can be by the thiazolyl blue MTT (3- (4,5-Aimethylthiazo-2-yl) -2,5- of yellow
Aiphenyl tetrazolium bromiAe) it is reduced to insoluble bluish violet formazan (Formanzan), this enzyme in dead cell
It disappears, MTT is not reduced.Optical density can be detected at 570nm with microplate reader with after the molten solution formazan of AMSO (dimethyl sulfoxide)
(OA), OD value is directly proportional to viable count.
Cell strain used are as follows: BGC-823 (gastric carcinoma cells) and HCT-8 (human colon cancer cell).
Test method: mtt assay: logarithmic growth phase cell, sufficiently piping and druming dilutes after counting at single cell suspension after digestion
At 1 × 104Cell/mL is inoculated in 96 well culture plates, 100 holes μ L/.4-5 concentration rank of each sample design, then exists
It is added the culture medium of 100 μ L various concentration rank samples in experimental port, parallel 3 hole of each concentration rank.The bodies such as control group addition
Product solvent.96 well culture plates are placed in 37 DEG C, 5%CO2After cultivating 96 hours in saturated humidity incubator, culture solution is discarded, often
The serum free medium containing 0.20 mg/mL MTT of fresh configuration is added in hole, and after continuing culture at 37 DEG C 4 hours, centrifugation is removed
Remove supernatant.150 μ L AMSO dissolution Formazan precipitating is added in every hole, and setting to shake on micro oscillator makes it sufficiently molten for 5 minutes
Solution.Rate processed at 570nm is measured in 550 type microplate reader of BIORAA to map to obtain metering curve, and the plate of drug is read from curve
Book inhibition concentration (IC50) value.
Inhibiting effect of the 2 fresh bamboo sap element A of table to BGC-823 (gastric carcinoma cells)
Inhibiting effect of the 2 fresh bamboo sap element A of table to HCT-8 (human colon cancer cell)
| Sample | Concentration (mol/L) | Inhibiting rate (%) | IC50(μM) |
| Physiological saline (feminine gender) | 0 | 0 | 0 |
| Fresh bamboo sap element A | 1×10-5 | 70.4 | 2.9 |
| 1×10-6 | 42.2 | ||
| 1×10-7 | 20.3 | ||
| 1×10-8 | 8.9 |
Summarize: fresh bamboo sap element A has inhibiting effect to gastric carcinoma cells and human colon cancer cell, can be used for developing treatment cancer
The drug of disease or tumour.
Claims (10)
1. the naphthalene compounds fresh bamboo sap element A of structure formula (I) or its pharmaceutically acceptable salt
2. naphthalene compounds fresh bamboo sap element A described in accordance with the claim 1 or its pharmaceutically acceptable salt, wherein the pharmacy
Upper acceptable salt, the salt that naphthalene compounds fresh bamboo sap element A and inorganic acid, organic acid selected from structure formula (I) are formed, Huo Zheyu
The salt that alkali metal, alkaline-earth metal are formed.
3. the preparation method of naphthalene compounds fresh bamboo sap element A described in claim 1 or its pharmaceutically acceptable salt, feature
It is that the preparation step of naphthalene compounds fresh bamboo sap element A is successively as follows:
(1) destructive distillation is extracted: after moso bamboo cutting, obtaining fresh bamboo sap through destructive distillation；
(2) medicinal extract concentrated extracting solution: is concentrated under reduced pressure to obtain in fresh bamboo sap；
(3) it extracts: taking fresh bamboo sap medicinal extract (37.8kg), purified water 40L is added to dissolve, then three times with the extraction of 160L ethyl acetate, second
Acetoacetic ester extract liquor；
(4) acetic acid ethyl acetate extract is concentrated: acetic acid ethyl acetate extract being concentrated under reduced pressure, ethyl acetate extract (310g) is obtained；
(5) column chromatography for separation: after ethyl acetate extract is dissolved with proper amount of methanol, with 1: 1.5 silica gel mixed sample, sample dry method dress
Enter silica gel column chromatography (internal diameter 14cm, pillar height 90cm, 100~200 mesh of column filling gel granularity), with chloroform-methanol (15:
1) it is elution 3h, eluent is collected with every part of 3L, collects 49 parts altogether, be concentrated to dryness respectively, through thin layer
Detection merges 18-28 parts of eluting fractions (111.9g), and by itself and 120g silica gel mixed sample, sample wet process is packed into silica gel column chromatography
(internal diameter 10cm, pillar height 124cm, 100~200 mesh of column filling gel granularity), with chloroform-methanol (80: 1~20: 1) gradient
8h is eluted, every part is collected by 2L, is collected 145 parts altogether, is inspected through thin-layer chromatography, and 50-57 parts of eluting fractions are merged
(23g), above-mentioned fraction is through C18Middle pressure reversed phase column chromatography (40cm × 7cm, 5 μm), is washed with methanol-water (32: 68~86: 14) gradient
De- (20ml/ minutes), every part is collected by 400mL, is collected 79 parts altogether, is inspected through thin-layer chromatography, and 27-30 parts of elutions are merged
Fraction (20mg), the fraction are fresh bamboo sap element A crude product；
(6) purifying of monomeric compound: fresh bamboo sap element A crude product inverted high performance preparative liquid chromatography (chromatographic column: C18 5μm,
250mm × 20mm, Detection wavelength: 210nm), with methanol-water (55: 45, v/v, 7mL/min) for eluent, through preparing liquid phase system
It is standby at 146min fresh bamboo sap element A (6mg) of the invention, fresh bamboo sap element A are through high performance liquid chromatography detection, chromatographic condition,
Chromatographic column: C18(250mm × 4.6mm, 5 μm)；Mobile phase: methanol-water (55: 45)；Detection wavelength: 210nm；Column temperature: 30 DEG C；Into
Sample amount: 10 μ l are calculated through area normalization method, fresh bamboo sap element A purity >=99%.
4. preparation method according to claim 3, it is characterized in that eluant, eluent is chloroform-methanol, chloroform and first in step (5)
Alcohol volume proportion are as follows: 25: 1 or 10: 1 or 8: 1 or 7: 1 or 5: 1；Gradient elution agent is methanol-water, and methanol volumetric concentration is 20%
~80%.
5. preparation method according to claim 3, it is characterized in that eluant, eluent is methanol-water, methanol and water body in step (6)
Product concentration is 40%~70%.
6. naphthalene compounds fresh bamboo sap element A described in claim 1 or its pharmaceutically acceptable salt exist
Prepare the application in anti-tumor drug.
7. application according to claim 6, the tumour is selected from: gastric cancer, liver cancer, colon cancer, bladder cancer.
8. a kind of Pharmaceutical composition, containing the naphthalene compounds fresh bamboo sap element A described in claim 1 or its pharmaceutically may be used
The salt of receiving.
9. pharmaceutical composition according to claim 8, wherein further including pharmaceutically acceptable carrier.
10. pharmaceutical composition according to claim 9, described pharmaceutical composition is to be suitble to medicinal dosage form, described
Pharmaceutical formulation is selected from: tablet, capsule, granule, pill, powder, paste, suspension, injection, suppository, drops, dripping pill
Agent, oral solution, patch.
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2018
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Non-Patent Citations (1)
| Title |
|---|
| ATSUSHI KAIHO ET AL: ""Construction of the di(trimethylolpropane) cross linkage and the phenylnaphthalene structure coupled with selective β-O-4 bond cleavage for synthesizing lignin-based epoxy resins with a controlled glass transition temperature"", 《GREEN CHEMISTRY》 * |
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