CN110092790A - A kind of alkaloid compound and its preparation method and application - Google Patents

A kind of alkaloid compound and its preparation method and application Download PDF

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CN110092790A
CN110092790A CN201910501587.7A CN201910501587A CN110092790A CN 110092790 A CN110092790 A CN 110092790A CN 201910501587 A CN201910501587 A CN 201910501587A CN 110092790 A CN110092790 A CN 110092790A
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alkaloid compound
preparation
compound
alkaloid
powder
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CN110092790B (en
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向文胜
王继栋
张继
李建宋
王相晶
郭晓为
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Northeast Agricultural University
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    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D487/00—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, not provided for by groups C07D451/00 - C07D477/00
    • C07D487/02—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, not provided for by groups C07D451/00 - C07D477/00 in which the condensed system contains two hetero rings
    • C07D487/10—Spiro-condensed systems
    • C—CHEMISTRY; METALLURGY
    • C12—BIOCHEMISTRY; BEER; SPIRITS; WINE; VINEGAR; MICROBIOLOGY; ENZYMOLOGY; MUTATION OR GENETIC ENGINEERING
    • C12P—FERMENTATION OR ENZYME-USING PROCESSES TO SYNTHESISE A DESIRED CHEMICAL COMPOUND OR COMPOSITION OR TO SEPARATE OPTICAL ISOMERS FROM A RACEMIC MIXTURE
    • C12P17/00—Preparation of heterocyclic carbon compounds with only O, N, S, Se or Te as ring hetero atoms
    • C12P17/18—Preparation of heterocyclic carbon compounds with only O, N, S, Se or Te as ring hetero atoms containing at least two hetero rings condensed among themselves or condensed with a common carbocyclic ring system, e.g. rifamycin
    • C12P17/182—Heterocyclic compounds containing nitrogen atoms as the only ring heteroatoms in the condensed system

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Abstract

The invention discloses a kind of alkaloid compounds and its preparation method and application, are related to compound and its preparation method and application, and the alkaloid compound chemical structural formula is shown in formula I:

Description

A kind of alkaloid compound and its preparation method and application
Technical field
The present invention relates to compounds and its preparation method and application, and in particular to a kind of alkaloid compound and its preparation Methods and applications.
Background technique
Viral disease transmission is strong, seriously endangers human health and life.The 1980s, the mankind of discovery exempted from AIDS caused by epidemic disease deficiency disorders (HIV) is that harmfulness is very big, the very high infectious disease of the death rate.Have found one kind again within 2003 Serious acute respiratory syndrome caused by new coronavirus (SARS) has highly infectious, lethality height.It there is no energy at present Effectively treat the drug of the disease.Therefore, the research of antiviral drugs becomes one of the hot spot of current international research.It is clinical at present Mainly there are several types of resisiting influenza virus and respiratory diseases cytotoxic drugs: anti-herpesvirus medicament: anti-giant cell for upper common drug Virus drugs；Anti-hepatitis virus medicament: resisting HIV drug.The treatment of antiviral drugs, which has nearly 30 years, goes through History, after cell entry body, the Biochemical Mechanism for imitating host is replicated and is bred in host cell, therefore, can be pressed down The drug of virus breeding processed has different degrees of damage to host cell or body, so that the development of antiviral agent and antibiotic phase It is slow for comparing.Up to the present, it there is no completely satisfactory antiviral agent.
Plant virus is a kind of important pathogen to harm the crops, because its harm is big, prevention and treatment is difficult, custom have plant cancer it Claim.Since plant virus is to the absolute parasitics of plant cell, substance, energy place required for virus replication etc. is completely by posting Main offer, virus can coerce the Biochemical Mechanism of host cell, be difficult to the Biochemical Mechanism tied up in knots of itself and virus itself Identification causes to study highly selective change so drug is difficult to only carry out targeted attack without injuring host cell to virus It learns anti-virus formulation and faces great difficulty, do not obtain important breakthrough yet so far.
In recent years, the research in relation to antiviral natural drug both at home and abroad is increasing, therefrom screens its effective component and has become For a hot spot of current antiviral new drug development, and make great progress.Currently, the research master of antiviral natural drug Active components of plants is concentrated on, and it is considerably less to the research in terms of the antiviral metabolite of microorganism, therefore, microorganism conduct Natural treasure-house have huge potentiality wait for we go find and study.
Summary of the invention
To improve above-mentioned status, the present invention provides a kind of obtained by streptomycete Streptomyces gamaensis it is new Alkaloid compound and its preparation method and application.
Firstly, the present invention provides a kind of alkaloid compound, chemical structural formula is shown in formula I:
Secondly, the present invention provides the preparation method of above-mentioned alkaloid compound, the described method comprises the following steps:
(1) fermented and cultured streptomycete (Streptomycesgamaensis), prepares fermentation liquid；
(2) fermentation liquid for obtaining step (1) obtains thallus and supernatant by centrifugation, supernatant by resin adsorption, Afford organic solvent eluent；
(3) by organic solvent eluent obtained by step (2), contained by concentration, silica gel column chromatography and gel filtration chromatography There is the flow point sample of alkaloid compound；
(4) it chromatographs the progress reverse phase preparative column of flow point sample obtained in step (3) to obtain the alkaloids chemical combination Object.
Step (1) described fermented and cultured, the carbon source in culture medium includes glucose, soluble starch, cornstarch, paste One of essence, industrial molasses, glycerol, sucrose, sorbierite, mannitol, lactose, maltose or xylan or two kinds or more；Training Supporting the nitrogen source in base includes yeast powder, yeast pumping object, soybean cake powder, soy meal, peptone, beef extract, yeast extract, corn One of paste dry powder, wheat bran, seitan powder, urea or ammonium salt or two kinds or more.
Preferably, step (1) fermented and cultured, the carbon source in culture medium are the mixture of glucose and soluble starch Or the mixture of glucose and cornstarch；Nitrogen source in culture medium is the mixture of yeast powder and soybean cake powder.
The bacterial strain Streptomycesgamaensis that step (1) is related to is isolated generation bases from soil The streptomycete of compound.Registration number of the 16S rRNA of the bacterial strain on Genbank is KT963951.The bacterium is big by northeast agricultural It learns biochemical industry laboratory to provide, is preserved in " China General Microbiological culture presevation administrative center ", deposit number are as follows: CGMCC (bacterial strain discloses in periodical No.4.7304: Antonie Van Leeuwenhoek.2017；110(4):471- 477.Streptomyces gamaensis sp.nov.,a novel actinomycete with antifungal activity isolated from soil in Gama,Chad.Shanshan Zhao,Lan Ye,Chongxi Liu, Adam Yacoub Abagana,Weiwei Zheng,Pengyu Sun,Jiansong Li,Wensheng Xiang, Xiangjing Wang)。
Step (2) resin is macroporous absorbent resin, preferably HP-20 macroporous absorbent resin；Have used in the elution Solvent includes one of acetone, methanol, ethyl alcohol or two kinds or three kinds.
Silica gel column chromatography described in step (3) uses the silica gel of partial size 100-200 mesh, uses acetone: n-hexane (V/V)= The solution of 0:100-50:50 is that elution solution is eluted；The gel filtration chromatography uses gel column SephadexLH-20, Use chloroform: methanol (V/V)=1:1 solution is that elution solution is eluted.
The chromatography of reverse phase preparative column described in step (4) uses C18 reverse phase filler, and the eluting solvent used is the water-soluble of acetonitrile The mixed liquor of liquid, the aqueous solution of methanol or methanol, acetonitrile and water.
Third, the present invention also provides above-mentioned alkaloid compounds in preparing antiviral composition or antiviral drugs Using.
The virus is tobacco mosaic virus (TMV), cucumber mosaic virus etc..
Beneficial effect
The present invention obtains new bio alkaloid compound HX117A, right compared with antiviral drugs Ningnanmycin is commercialized Cucumber mosaic virus and tobacco mosaic virus (TMV) are shown quite or stronger antiviral activity, can be used for opening for antiviral agent Hair.
Specific embodiment
The fermented and cultured of alkaloid compound producing strains Streptomycesgamaensis and alkaloid compound It extracts, the specific embodiment that separation and activity experiment are seen below.It is the following examples are further illustrations of the invention but unlimited The system present invention.
Embodiment 1
(1) fermented and cultured streptomycete (Streptomycesgamaensis), prepares fermentation liquid:
1) fermenting microbe: fermenting microbe is streptomycete Streptomycesgamaensis.
2) ISP2 culture medium (yeast extract 4.0g, brewer's wort 10.0g, glucose 4.0g, agar inclined-plane culture: are used 20.0g, distilled water 1000ml, pH value 7.0-7.2) sterilize 20min at 121 DEG C, it is cultivated 6-8 days at 28 DEG C after connecing bacterium.
3) seed culture: seed culture medium composition: glucose 4.0g/L, malt leach powder 10.0g/L, yeast powder 4.0g/ L, CaCO30.2g/L, distilled water 1000ml, pH value 7.0, with every bottle of packing 250ml of triangular flask of 1000ml, then with 12ml without Spore suspension is washed down and be made to the streptomycete spore on inclined-plane by bacterium water, makes its concentration 1 × 107-1×108A/mL.Every bottle adds 2ml spore suspension, is placed on shaking table, and revolving speed 250r/min, 28 DEG C of cultures are for 24 hours.
4) fermented and cultured: fermentation medium composition: yeast powder 0.5g/L, cornstarch 3.0g/L, glucose 1.0g/L are yellow Beancake powder 2.0g/L, NaCl 0.1g/L, K2HPO40.2g/L, MgSO4·7H2O 0.1g/L, CaCO30.2g/L, pH value 7.2- 7.4, distilled water configuration, sterilize 20min at 121 DEG C.By 8%vol inoculum concentration, seed liquor is accessed in 50L fermentor (the 30L amount of containing) is cultivated under the conditions of 28 DEG C, and stirring rate is 100r/min, ventilation rate 120m3/ h is cultivated 6-7 days.
(2) fermentation liquid for obtaining step (1) obtains thallus and supernatant by centrifugation, and supernatant passes through HP-20 macropore Resin adsorption is first rinsed with water, then obtains ethanol eluate with 80% ethanol elution.
(3) by organic solvent eluent obtained by step (2), contained by concentration, silica gel column chromatography and gel filtration chromatography Have the flow point sample of alkaloid compound: by the ethanol eluate being collected into 50 DEG C of reduced pressures removal ethyl alcohol mutually until It is dry, obtain 69g oily mater.By silicagel column on resulting oily mater (partial size 100-200 mesh) carry out column chromatography, use just oneself Alkane: acetone=50:50 (V/V) is eluted, and is detected by TLC, obtains 3 components (1-3).By component 2 through gel LH-20 column Chromatography (chloroform/methanol=1:1, V/V) obtains component 2-2.
(4) it chromatographs the progress reverse phase preparative column of flow point sample obtained in step (3) to obtain biology described in claim 1 Alkaloid compound:
Condition is as follows:
Liquid phase systems: Agilent 1,100 half prepares high pressure liquid chromatograph；
Chromatographic column: SepaxAmethyst C18-H (4.6mm × 250mm)；
Eluant, eluent: acetonitrile/water=18:82 (V/V)；Flow velocity: 1.0mL/min；
Detection wavelength: λ=220nm；
It collects the peak that retention time is 9.9min and obtains the alkaloid compound, be named as compound HX117A.
The Structural Identification of compound HX117A
Determine that the structure of compound HX117A is as follows by Spectrum Analysis such as 1D and 2D NMR, MS:
The physicochemical property of compound HX117A is as follows:
Character: white powder
Dissolubility: being soluble in methanol, acetone, be slightly soluble in water, does not dissolve in petroleum ether
Molecular formula: C9H13N5O4
Specific rotation:
High resolution mass spectrum (HRESI-MS): 278.0874 [M+Na]+(calcd for C9H13N5O4Na 278.0870)
Ultra-violet absorption spectrum (UV absorption spectrum) λmax(EtOH) nm (log ε): 209 (4.72)
Infrared absorption spectrum (IR absorption spectrum) Vmaxcm-1: 3409,3222,2953,1730,1459, 1391,1329,1025,911
Fusing point (DEG C): 189-192
Compound HX117A's1H and13C NMR(CDCl3) data are shown in Table 1.
Nuclear magnetic data (the hydrogen spectrum: 400MHz of 1 compound HX117A of table；Carbon spectrum: 100MHz)
Embodiment 2
The antiviral activity of compound HX117A
Withered spot host of 4~6 leaf phase Nicotiana glutinosas as tobacco mosaic virus (TMV) TMV or cucumber mosaic virus CMV is selected, is used Conventional juice rubbing manipulation is inoculated with the whole leaf of Nicotiana glutinosa, 2 days progress HX117A medicine liquid spray processing (control group treatment process phases after inoculation Together), incidence is checked after 14 days, calculates compound HX117A to the inhibitory activity of tobacco mosaic virus (TMV) (TMV), and with thiophene acyl Bacterium amine (TDL), diazosulfide (BTH) and Ningnanmycin (Ningnanmycin) are control group, as a result see the table below (table 2).Table 2 Inhibiting effect of the compound HX117A to tobacco mosaic virus (TMV) (TMV) and cucumber mosaic virus (CMV)
As can be seen from the results, compound HX117A is shown when concentration is 100mg/L to the extremely strong suppression of cucumber mosaic virus System activity, inhibiting rate 72.34%, higher than the antiviral activity (inhibiting rate 57.11%) of the Ningnanmycin of comparable sodium；? When concentration is 400mg/L, compound HX117A has an extremely strong inhibitory activity to tobacco mosaic virus (TMV), inhibiting rate 80.06%, but When concentration is 100mg/L, the anti-of comparable sodium Ningnanmycin is slightly lower than to the inhibiting rate (62.09%) of tobacco mosaic virus (TMV) Virus activity (67.56%).

Claims (10)

1. a kind of alkaloid compound, it is characterised in that: its chemical structural formula is shown in formula I:
2. a kind of preparation method of alkaloid compound as described in claim 1, it is characterised in that: the method includes with Lower step:
(1) fermented and cultured streptomycete (Streptomycesgamaensis), prepares fermentation liquid；
(2) fermentation liquid for obtaining step (1) obtains thallus and supernatant by centrifugation, and supernatant is by resin adsorption, elution Obtain organic solvent eluent；
(3) it by organic solvent eluent obtained by step (2), obtains by concentration, silica gel column chromatography and gel filtration chromatography containing life The flow point sample of object alkaloid compound；
(4) it chromatographs the progress reverse phase preparative column of flow point sample obtained in step (3) to obtain alkaloids described in claim 1 Compound.
3. the preparation method of alkaloid compound as claimed in claim 2, it is characterised in that: step (1) the fermentation training It supports, the carbon source in culture medium includes glucose, soluble starch, cornstarch, dextrin, industrial molasses, glycerol, sucrose, sorb One of alcohol, mannitol, lactose, maltose or xylan or two kinds or more；Nitrogen source in culture medium includes yeast powder, yeast Take out object, soybean cake powder, soy meal, peptone, beef extract, yeast extract, Dried Corn Steep Liquor Powder, wheat bran, seitan powder, urea or ammonium One of salt or two kinds or more.
4. the preparation method of alkaloid compound as claimed in claim 2, it is characterised in that: step (1) the fermentation training It supports, the carbon source in culture medium is the mixture or glucose of glucose and soluble starch and the mixture of cornstarch；Culture Nitrogen source in base is the mixture of yeast powder and soybean cake powder.
5. the preparation method of alkaloid compound as claimed in claim 2, it is characterised in that: step (2) described resin is Macroporous absorbent resin, preferably HP-20 macroporous absorbent resin；Organic solvent used in the elution includes acetone, methanol, in ethyl alcohol One kind or two kinds or three kinds.
6. the preparation method of alkaloid compound as claimed in claim 2, it is characterised in that: silica gel described in step (3) Column chromatography uses the silica gel of partial size 100-200 mesh, uses acetone: n-hexane (V/V)=0:100-50:50 solution is that elution is molten Liquid is eluted.
7. the preparation method of alkaloid compound as claimed in claim 2, it is characterised in that: gel described in step (3) Column chromatography uses gel column Sephadex LH-20, uses chloroform: methanol (V/V)=1:1 solution is that elution solution is washed It is de-.
8. the preparation method of alkaloid compound as claimed in claim 2, it is characterised in that: reverse phase described in step (4) Column chromatography is prepared using C18 reverse phase filler, the eluting solvent used be the aqueous solution of acetonitrile, the aqueous solution of methanol or methanol, The mixed liquor of acetonitrile and water.
9. alkaloid compound as described in claim 1 is preparing the application in antiviral composition or antiviral drugs.
10. alkaloid compound as claimed in claim 9 is preparing the application in antiviral composition or antiviral drugs, It is characterized by: the virus is one of tobacco mosaic virus (TMV) or cucumber mosaic virus or two kinds.
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