CN105906566A - Alkaloid compound with antibacterial activity in tobaccos as well as preparation method and use of alkaloid compound - Google Patents
Alkaloid compound with antibacterial activity in tobaccos as well as preparation method and use of alkaloid compound Download PDFInfo
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- CN105906566A CN105906566A CN201610338953.8A CN201610338953A CN105906566A CN 105906566 A CN105906566 A CN 105906566A CN 201610338953 A CN201610338953 A CN 201610338953A CN 105906566 A CN105906566 A CN 105906566A
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D221/00—Heterocyclic compounds containing six-membered rings having one nitrogen atom as the only ring hetero atom, not provided for by groups C07D211/00 - C07D219/00
- C07D221/02—Heterocyclic compounds containing six-membered rings having one nitrogen atom as the only ring hetero atom, not provided for by groups C07D211/00 - C07D219/00 condensed with carbocyclic rings or ring systems
- C07D221/04—Ortho- or peri-condensed ring systems
- C07D221/06—Ring systems of three rings
- C07D221/14—Aza-phenalenes, e.g. 1,8-naphthalimide
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- A—HUMAN NECESSITIES
- A01—AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
- A01N—PRESERVATION OF BODIES OF HUMANS OR ANIMALS OR PLANTS OR PARTS THEREOF; BIOCIDES, e.g. AS DISINFECTANTS, AS PESTICIDES OR AS HERBICIDES; PEST REPELLANTS OR ATTRACTANTS; PLANT GROWTH REGULATORS
- A01N43/00—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds
- A01N43/34—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with one nitrogen atom as the only ring hetero atom
- A01N43/40—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with one nitrogen atom as the only ring hetero atom six-membered rings
- A01N43/42—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with one nitrogen atom as the only ring hetero atom six-membered rings condensed with carbocyclic rings
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- D—TEXTILES; PAPER
- D21—PAPER-MAKING; PRODUCTION OF CELLULOSE
- D21H—PULP COMPOSITIONS; PREPARATION THEREOF NOT COVERED BY SUBCLASSES D21C OR D21D; IMPREGNATING OR COATING OF PAPER; TREATMENT OF FINISHED PAPER NOT COVERED BY CLASS B31 OR SUBCLASS D21G; PAPER NOT OTHERWISE PROVIDED FOR
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Abstract
The invention discloses an alkaloid compound. The alkaloid compound is chemically named as 8-hydroxy-3-hydroxymethyl-6,9-dimethyl-7H-benzo[de]isoquinoline-7-one and has a chemical formula C15H13NO3 and the structure shown in the specification. The invention further discloses a method for preparing the alkaloid compound from tobaccos. The invention further discloses use of the alkaloid compound. Activity tests prove that the alkaloid compound has a relatively good bacteriostatic action. The alkaloid compound is of a novel structure and has relatively good antibacterial activity. By applying the alkaloid compound to tipping paper of cigarettes, the possibilities of breeding and reproduction of bacteria in the tipping paper of the cigarettes can be eliminated or reduced.
Description
Technical field
The invention belongs to technical field of tobacco chemistry, be specifically related to a kind of extraction first from Nicotiana tabacum L. and obtain
Alkaloid compound.Meanwhile, the invention still further relates to the preparation method of this compound and connect antibacterial
Application in dress paper.
Background technology
Nicotiana tabacum L. is the plant that chemical composition is the most complicated in the world, and secondary metabolite is the abundantest, according to
Nineteen eighty-two Dube and Green etc. report, the chemical composition identified in Nicotiana tabacum L. is just more than 2549
Kind, by 2008, Rodgman and perfetti reported, Nicotiana tabacum L., tobacco and volume
The compound sum found in cigarette flue gas is about 8700 kinds.At present, people identify out from Nicotiana tabacum L.
Monomer chemistries material just more than kind more than 3000, and also have many compositions not yet to identify out.Nicotiana tabacum L.
In addition to being mainly used in cigarette smoking purposes, also can therefrom extract the multiple chemical composition having value,
Therefrom it is found to have the guiding compound of value of exploiting and utilizing.Alkaloid (alkaloid) is present in organism
The alkaline organic compound that a class in (predominantly plant) is nitrogenous, great majority have the circulus of complexity,
Nitrogen is included in ring more, has significant biological activity, is the important sources of medicine and biological pesticide.
For making full use of our province Nicotiana tabacum L. resources advantage, finding new bioactive natural product further, we are to cigarette
Grass chemical composition is studied, and a kind of new alkaloid of isolated from Yunnan Flue-cured Tobacco Nicotiana tabacum L.
Compounds, this compound it is not yet seen relevant report, it is worth mentioning at this point that this compound has
Significantly antibacterial activity.
Summary of the invention
It is an object of the invention to provide a kind of new alkaloid compound.
It is a further object to provide a kind of method preparing described alkaloid compound.
The present invention also aims to the application providing described alkaloid compound in antibiotic package paper.
Except as otherwise noted, the percent employed in the present invention is mass percent.
The present invention isolates a kind of new alkaloid compound from Nicotiana tabacum L., and its molecular formula is
C15H13NO3, there is following structural formula:
This compound named: 8-hydroxyl-3-methylol-6,9-dimethyl-7H-benzo [de] isoquinolin-7-
Ketone, English entitled: 8-hydroxy-3-(hydroxymethyl)-6,9-dimethyl-7H-benzo [de]
quinolin-7-one。
The method preparing described alkaloid compound, the method comprises the following steps:
(1) extractum extracts: pulverized by tobacco sample, with high concentration methanol (w%:80%～100%)
Or high concentration ethanol (w%:80%～100%) or high concentration acetone (w%:60%～90%) are
Extraction solvent, Extraction solvent: Nicotiana tabacum L. (weight ratio)=2～4:1, soak 24h～72h, extract 3～
5 times, united extraction liquid, filtering and concentrating become extractum；
(2) silica gel column chromatography: the pure methanol of extractum weight ratio 1.5～3 times amount or straight alcohol or pure third
Ketone uses weight ratio 0.8～the 80 of 1.2 times～100 mesh silica gel mixed sample, by weight ratio 2～4 times amount after dissolving
160～300 mesh silica gel dry column-packings carry out silica gel column chromatography；With volume proportion for (1:0,20:1,
9:1,8:2,7:3,6:4,1:1 and 1:2) chloroform-acetone solution carry out gradient elution, merge identical
Part, collect each several part eluent and also concentrate；
(3) high pressure liquid chromatography is isolated and purified: the 8:2 part of column chromatography eluent uses high pressure further
Liquid chromatograph is isolated and purified i.e. obtains described alkaloid compound.
High pressure liquid chromatography is isolated and purified is to use 21.2mm × 250mm, the C of 5 μm18Chromatographic column,
Flow velocity is 20mL/min, and flowing is the methanol of 52% mutually, and UV-detector detection wavelength is 342nm,
Sample introduction 200 μ L every time, collects the chromatographic peak of 31.5min, is evaporated after repeatedly adding up.
After described high performance liquid chromatography is isolated and purified, a preferred subsequent process scheme is, gained
Compound dissolves with pure methanol again, then with pure methanol for flowing phase, separates with gel filtration chromatography, with
The most isolated and purified.
Table 1 compound 11H-NMR and13C-NMR data (500/125MHz, C5D5N)
The structure of the alkaloid compound that method described above prepares is measured by the following method.
The compounds of this invention is orange red jelly, and HR-ESI-MS shows that its quasi-molecular ion peak is 278.0798
[M+Na]+, in conjunction with1H-and13C-NMR spectrum determines that molecular formula is C15H13NO3.Its infrared light
Spectrum display compound there is hydroxyl (3412cm-1), carbonyl (1650cm-1), and aromatic ring (1610,1567,
1462cm-1) signal, ultraviolet spectra has absorption maximum to also confirm that in compound 246 and 342nm
There is aromatic ring structure.From1Signal can be seen that in compound H H NMR spectroscopy (attribution data is shown in Table-1) has
3 aromatic series hydrogen signal (δH8.48s, 8.01 (d) 8.1,7.67 (d) 8.1)；2 methyl signals (δH
2.51s and 2.80s)；Methylene (the δ of 1 oxidationH4.62)；And 1 phenolic hydroxyl group (δH 10.42)。
Compound13C NMR and DEPT spectrum display compound there are 8 fragrant quaternary carbon (δC 125.3s、
131.6s、146.6s、124.7s、151.2s、123.0s、158.7s、120.2s)；3 fragrance
Methyl (δC142.6d、128.0d、134.3d)；1 alpha, beta-unsaturated carbonyl (δC181.1s)；2
Methyl (δC10.5q and 24.8q)；And the methylene (δ of 1 oxidationC66.9t).According to HSQC
Spectrum has belonged to the carbon signal that all hydrogen is corresponding.Pass through H3-13 and C-5, C-6, C-6a, H-5 and C-3a,
C-6a, C-14, H-4 and C-3, C-3a, C-11, H2-12 and C-2, C-3, C-3a, and H-2
Relevant with the HMBC of C-3, C-3a, C-12, C-10, it can be verified that compound exists 3-methylol
The structure fragment of-6-methyl different Kui quinoline.Degree of unsaturation 10 according to compound, also should have in this compound
1 ring.According to H3-14 is relevant with the HMBC of C-8, C-9, C-10, can speculate α, β-unsaturation
β-carbon (C-9) and the C-10 position of isoquinolin ring in carbonyl are connected, and carbonyl (C-7) should be with C-6a phase
Connect and form 1 hexatomic ring.Another 1 methyl (C-14) is substituted in C-9 position by H3-14 and C-8, C-9,
The HMBC of C-10 is relevant to be determined.Phenolic hydroxyl group is substituted in C-8 position can be according to the chemical shift of C-8
Value (δC151.2) in low field, and phenolic hydroxyl group signal (δH10.42) and C-7, C-8, C-9 HMBC
It is correlated with and determines.So far the structure of this compound is determined.This Compound nomenclature is: 8-hydroxyl-3-hydroxyl first
Base-6,9-dimethyl-7H-benzo [de] isoquinolin-7-ketone.
This compound has been carried out Antimicrobial Screening, its to staphylococcus aureus, escherichia coli,
Angstrom uncommon bacterium, bacillus subtilis, Bacillus proteus etc. have significant activity.
This compound is applied in cigarette tipping paper, compares with comparison, adds connecing of this compound
Dress paper detection total number of bacteria, coliform, staphylococcus aureus, bacillus pyocyaneus, hemolytic hammer
Bacterium, total number of fungi substantially reduce；To escherichia coli (ATCC25922), staphylococcus aureus
(ATCC6538) bacteriostasis rate entirely reaches more than 96%, it is possible to reduce or eliminate cigarette tipping paper and
Bacteria breed and the probability of breeding in storage process, it addition, in smoking property of cigarette, transmittance process,
This antibacterial action also is able to microorganism contaminated to the tipping paper on Cigarette and plays inhibitory action.
Compared with prior art, the present invention has an advantage highlighted below: the raw materials of compound of (1) present invention
Being easy to get, extracting method is simple, can be easily separated and obtains；Molecular structure is also simple, easily realizes artificial conjunction
Become.(2) have employed conventional column chromatography and the preparation method of high performance liquid chromatography combination, compound preparation behaviour
Making flow process simple, the compounds of this invention purity obtained is high, and follow-up industrialized production easily realizes.
(3) the compounds of this invention is nontoxic to animal, uses safety, shows good antibacterial activity, to large intestine
The bacteriostasis rate of bacillus, staphylococcus aureus etc. entirely reaches more than 96%；It is applied to cigarette tipping paper,
Microorganism contaminated to cigarette tipping paper can play inhibitory action.Cigarette tipping paper is directly and oral cavity
Contact, the use in cigarette tipping paper of this compound can be avoided at Medicated cigarette sucking, in transmittance process
Microbial contamination, is effectively increased health and the safety of Medicated cigarette.
Accompanying drawing explanation
Fig. 1 is the carbon-13 nmr spectra of alkaloid compound of the present invention；
Fig. 2 is the proton nmr spectra of alkaloid compound of the present invention；
Fig. 3 is that the main HMBC of alkaloid compound of the present invention is correlated with.
Detailed description of the invention
The present invention is described in further detail with embodiment below in conjunction with the accompanying drawings, but not with any side
The present invention is any limitation as by formula, based on present invention teach that any conversion or improvement made, each falls within this
The protection domain of invention.
Embodiment 1
Prepare alkaloid compound C15H13NO3, including extractum extraction, silica gel column chromatography, high pressure liquid
Phase chromatographic isolation, specifically uses following steps:
1. extractum extracts: takes Nicotiana tabacum L. and pulverizes, with high concentration methanol (w%:95%) or high concentration ethanol
(w%:95%) or high concentration acetone (w%:70%) is Extraction solvent, Extraction solvent: Nicotiana tabacum L. (weight
Amount ratio)=3:5, to soak 54h, extract 4 times, united extraction liquid, filtering and concentrating become extractum.
2. silica gel column chromatography: the pure methanol of extractum weight ratio 2.5 times amount or straight alcohol or pure acetone dissolve
Afterwards with 80～100 mesh silica gel mixed samples of weight ratio 1.2 times, do with 250 mesh silica gel of weight ratio 3 times amount
Method dress post carries out silica gel column chromatography；With volume proportion for (1:0,20:1,9:1,8:2,7:3,6:4,
1:1 and 1:2) chloroform-acetone solution carry out gradient elution, merge identical part, collect each several part
Eluent also concentrates.
3. high pressure liquid chromatography separates: the 8:2 part of column chromatography eluent uses high pressure liquid chromatography further
Isolated and purified i.e. obtaining described alkaloid compound, high pressure liquid chromatography is isolated and purified is employing 21.2
Mm × 250mm, the C of 5 μm18Chromatographic column, flow velocity is 20mL/min, and flowing is the first of 52% mutually
Alcohol, UV-detector detection wavelength is 342nm, and each sample introduction 200 μ L collects the color of 31.5min
Spectral peak, is evaporated after repeatedly adding up.
Material after high pressure lipuid chromatography (HPLC) is isolated and purified, a preferred post processing scheme is, gained
Compound dissolves with pure methanol again, then with pure methanol for flowing phase, separates with gel filtration chromatography, with
The most isolated and purified.
Raw tobacco material used by the present invention is not limited by area and kind, all can realize the present invention, below
To derive from the raw tobacco material of Yunnan different sources, the present invention will be further described:
Embodiment 2
Tobacco sample derives from Yunnan Yuxi, and kind is Yuxi K326.Nicotiana tabacum L. samples 2.0kg pulverize
Methanol extraction with 95% 5 times, extracts 24h every time, and extracting solution merges, and filters, and concentrating under reduced pressure becomes
Extractum, obtains extractum 105g.The pure methanol of extractum weight ratio 2.0 times amount uses the 100 of 120g after dissolving
The thick silica gel mixed sample of mesh, the 160 mesh silica gel dress posts of 0.6kg carry out silica gel column chromatography, with volume proportion are
The chloroform of 1:0,20:1,9:1,8:2,7:3,6:4,1:1,1:2-acetone gradient elution, TLC monitors
Merging identical part, obtain 8 parts, wherein volume proportion is the chloroform-acetone eluting portion of 8:2
Prompt logical sequence 1,100 half preparative high-performance liquid chromatographic of demultiplexing peace separates, and the methanol with 52% is flowing phase, Zorbax
It is fixing phase that SB-C18 (21.2 × 250mm, 5 μm) prepares post, and flow velocity is 20ml/min, and ultraviolet is examined
Surveying device detection wavelength is 342nm, and each sample introduction 200 μ L collects the chromatographic peak of 31.5min, repeatedly
It is evaporated after Lei Jia；Products therefrom dissolves with pure methanol again, then with pure methanol for flowing phase, uses
Sephadex LH-20 gel filtration chromatography separates, and obtains this noval chemical compound.
Embodiment 3
Tobacco sample derives from Dali, and kind is cloud and mist 200, and Nicotiana tabacum L. samples 3.5kg chopping,
Ethanol extraction with 95% 4 times, extracts 48h every time, and extracting solution merges, and filters, and concentrating under reduced pressure becomes
Extractum, obtains extractum 250g.The pure methanol of extractum weight ratio 2.0 times amount uses the 80 of 250g after dissolving
The thick silica gel mixed sample of mesh, the 200 mesh silica gel dress posts of 1.2kg carry out silica gel column chromatography, with volume proportion are
The chloroform of 1:0,20:1,9:1,8:2,7:3,6:4,1:1,1:2-acetone gradient elution, TLC monitors
Merging identical part, obtain 8 parts, wherein volume proportion is the chloroform-acetone eluting portion of 8:2
Prompt logical sequence 1,100 half preparative high-performance liquid chromatographic of demultiplexing peace separates, and the methanol with 52% is flowing phase, Zorbax
It is fixing phase that SB-C18 (21.2 × 250mm, 5 μm) prepares post, and flow velocity is 20ml/min, and ultraviolet is examined
Surveying device detection wavelength is 342nm, and each sample introduction 200 μ L collects the chromatographic peak of 31.5min, repeatedly
It is evaporated after Lei Jia；Products therefrom dissolves with pure methanol again, then with pure methanol for flowing phase, uses
Sephadex LH-20 gel filtration chromatography separates, and obtains this noval chemical compound.
Embodiment 4
Tobacco sample derives from Kunming, Yunnan, and kind is the big gold dollar of Flos Carthami, Nicotiana tabacum L. samples 5kg and pulverizes,
Acetone with 75% supersound extraction 3 times, extracts 72h every time, and extracting solution merges, and filters, reduces pressure dense
Shorten extractum into, obtain extractum 380g.The pure methanol of extractum weight ratio 1.6 times amount uses 400g after dissolving
The 90 thick silica gel mixed samples of mesh, 2.4kg 180 mesh silica gel dress posts carry out silica gel column chromatography, join with volume
Than the chloroform-acetone gradient elution for 1:0,20:1,9:1,8:2,7:3,6:4,1:1,1:2, TLC
Monitoring merges identical part, obtains 8 parts, and wherein volume proportion is that the chloroform-acetone of 8:2 is washed
De-part prompt logical sequence 1,100 half preparative high-performance liquid chromatographic of peace separates, and the methanol with 52% is flowing phase,
It is fixing phase that Zorbax SB-C18 (21.2 × 250mm, 5 μm) prepares post, and flow velocity is 20ml/min,
UV-detector detection wavelength is 342nm, and each sample introduction 200 μ L collects the chromatographic peak of 31.5min,
It is evaporated after repeatedly adding up；Products therefrom dissolves with pure methanol again, then with pure methanol for flowing phase, uses
Sephadex LH-20 gel filtration chromatography separates, and obtains this noval chemical compound.
Embodiment 5
The qualification of------compound structure
Compound prepared by Example 1-4, the alkaloid compound that method described above prepares
Structure is measured by the following method.Compound is orange red jelly, and HR-ESI-MS shows it
Quasi-molecular ion peak is 278.0798 [M+Na]+, in conjunction with1H-and13C-NMR spectrum determines molecular formula
For C15H13NO3.Its infrared spectrum display compound there is hydroxyl (3412cm-1), carbonyl (1650
cm-1), and aromatic ring (1610,1567,1462cm-1) signal, ultraviolet spectra is 246 and 342nm
There is absorption maximum to also confirm that in compound and there is aromatic ring structure.From1H H NMR spectroscopy (attribution data is shown in Table-1)
Signal can be seen that 3 aromatic series hydrogen signal (δ in compoundH8.48s, 8.01 (d) 8.1,7.67 (d)
8.1)；2 methyl signals (δH2.51s and 2.80s)；Methylene (the δ of 1 oxidationH4.62)；And
1 phenolic hydroxyl group (δH10.42).Compound13C NMR and DEPT spectrum display compound there are 8
Fragrance quaternary carbon (δC 125.3s、131.6s、146.6s、124.7s、151.2s、123.0s、158.7s、
120.2s)；3 fragrant methine (δC142.6d、128.0d、134.3d)；1 α, β-unsaturation carbonyl
Base (δC181.1s)；2 methyl (δC10.5q and 24.8q)；And the methylene (δ of 1 oxidationC
66.9t).The carbon signal that all hydrogen is corresponding has been belonged to according to hsqc spectrum.Pass through H3-13 and C-5, C-6,
C-6a, H-5 and C-3a, C-6a, C-14, H-4 and C-3, C-3a, C-11, H2-12 and C-2,
C-3, C-3a, and the HMBC of H-2 with C-3, C-3a, C-12, C-10 is relevant, it can be verified that
Compound exists the structure fragment of 3-methylol-6-methyl different Kui quinoline.Degree of unsaturation according to compound
10, this compound also should have 1 ring.According to H3-14 and the HMBC phase of C-8, C-9, C-10
Closing, can speculate α, β-carbon (C-9) and the C-10 position of isoquinolin ring in beta-unsaturated carbonyl are connected, and
Carbonyl (C-7) should be connected with C-6a and form 1 hexatomic ring.Another 1 methyl (C-14) is substituted in C-9
Position is by H3-14 relevant with the HMBC of C-8, C-9, C-10 are determined.Phenolic hydroxyl group is substituted in C-8
Position can be according to the chemical displacement value (δ of C-8C151.2) in low field, and phenolic hydroxyl group signal (δH10.42) and
C-7, C-8, C-9 HMBC relevant determine.So far the structure of this compound is determined.Should
Compound nomenclature is: 8-hydroxyl-3-methylol-6,9-dimethyl-7H-benzo [de] isoquinolin-7-ketone.
Embodiment 6
The compound of Example 3 preparation, for yellow jelly.Assay method is same as in Example 5,
Confirm that compound prepared by embodiment 3 is described alkaloid compound 8-hydroxyl-3-methylol
-6,9-dimethyl-7H-benzo [de] isoquinolin-7-ketone.
Embodiment 7
The compound of Example 4 preparation, for yellow jelly.Assay method is same as in Example 5,
Confirm that compound prepared by embodiment 4 is described 8-hydroxyl-3-methylol-6,9-dimethyl-7H-benzo
[de] isoquinolin-7-ketone.
Embodiment 8
Prepared by Example 1-4 appoints alkaloid compound to carry out antibacterial activity test, and test situation is such as
Under:
Antimicrobial test agar diffusion method is carried out, and first tested bacterium is coated in plain agar equably
On the flat board of culture medium (Carnis Bovis seu Bubali cream, peptone, sodium chloride, serum, agar), then by testing compound
(alkaloid compound 10mL DMSO dissolves, and dilute becomes the solution of 50 μ g/mL) soaks
Tablet (diameter 5mm) be placed in the culture medium carried disease germs, put into calorstat, hatch 24-72 in 25 DEG C
Inhibition zone size is observed after h.Result shows: the compounds of this invention is to staphylococcus aureus, large intestine bar
Bacterium, angstrom uncommon bacterium, bacillus subtilis, a Bacillus proteus etc. have the strongest activity；Suppression ratio is more than 96%.
Embodiment 9
The compounds of this invention is carried out safety evaluatio, by Micronuclei In The Mouse Bone Marrow experiment, Ames in fact
Test and test with TK gene mutation, it was demonstrated that the compounds of this invention is nontoxic to animal, uses safety.This chemical combination
Thing is added on cigarette tipping paper with the concentration of 50 μ g/mL；" disposably make by the People's Republic of China (PRC)
Use hygienic article sanitary standard " detection method of GB15979-2002, take and added the compounds of this invention
Volume cigarette tipping paper, 2.0 × 3.0mm size, detection total number of bacteria, coliform, golden yellow Fructus Vitis viniferae
Coccus, bacillus pyocyaneus, Hemolytic streptococcus, total number of fungi.Result shows, adds of the present inventionization
The tipping paper total plate count of compound significantly reduces, and the antibacterial of several tests is had and substantially presses down by this compound
Make use, the bacteriostasis rate of escherichia coli, staphylococcus aureus etc. is entirely reached more than 96%.
Claims (8)
1. an alkaloid compound with following structural formula:
This compound named: 8-hydroxyl-3-methylol-6,9-dimethyl-7H-benzo [de] isoquinolin-7-ketone, English
Literary fame is: 8-hydroxy-3-(hydroxymethyl)-6,9-dimethyl-7H-benzo [de] quinolin-7-one.
2. the method preparing alkaloid compound described in claim 1, the method comprises the following steps:
(1) extractum extracts: with Nicotiana tabacum L. as raw material, is pulverized by Nicotiana tabacum L. or is cut into segment, using concentration expressed in percentage by weight
The methanol of 80%～100% or ethanol, or the acetone of concentration expressed in percentage by weight 60%～90% is Extraction solvent, carries
Take solvent: weight ratio=2 of Nicotiana tabacum L.～4:1, soak 24h～72h, extract 3～5 times, united extraction liquid,
Filtering and concentrating becomes extractum；
(2) silica gel column chromatography: 160～300 mesh silica gel dry column-packings of extractum weight ratio 2～4 times amount enter
Row silica gel column chromatography；Carry out gradient elution with chloroform-acetone solution, merge identical part, collect each several part
Eluent also concentrates；
(3) high pressure liquid chromatography is isolated and purified: the 8:2 part of eluent is divided by high pressure liquid chromatography further
Required alkaloid compound is i.e. obtained from purification.
Preparation method the most according to claim 2, it is characterised in that: in step (3), high pressure liquid
Compound after phase chromatographic separation and purification dissolves with pure methanol again, then with pure methanol for flowing phase, uses gel
Column chromatography for separation, with the most isolated and purified.
Preparation method the most according to claim 2, it is characterised in that: in step (3), described
High pressure liquid chromatography is isolated and purified is to use 21.2mm × 250mm, the C of 5 μm18Chromatographic column, flow velocity is
20mL/min, flowing is the methanol of 52% mutually, and UV-detector detection wavelength is 342nm, each sample introduction
200 μ L, collect the chromatographic peak of 31.5min, are evaporated after repeatedly adding up.
Preparation method the most according to claim 2, it is characterised in that: in step (2), described
Extractum is before silica gel column chromatography rough segmentation, with the pure methanol of weight ratio 1.5～3 times amount or straight alcohol or pure acetone
After dissolving, with weight ratio 0.8～the 80 of 1.2 times～100 mesh silica gel mixed sample.
Preparation method the most according to claim 2, it is characterised in that: in step (2), described
Gradient elution, chloroform-acetone solution volume proportion is 1:0,20:1,9:1,8:2,7:3,6:4,1:1 and 1:2.
Alkaloid compound the most according to claim 1 is for killing the purposes of antibacterial and fungus.
Purposes the most according to claim 7, is wherein applied to cigarette tipping by this alkaloid compound
On paper.
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Cited By (1)
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| CN111018822A (en) * | 2019-12-11 | 2020-04-17 | 云南中烟工业有限责任公司 | Compound with bacteriostatic action, preparation method thereof and application thereof in cigarettes |
| CN111018822B (en) * | 2019-12-11 | 2022-05-24 | 云南中烟工业有限责任公司 | Compound with bacteriostatic action, preparation method thereof and application thereof in cigarettes |
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| Publication number | Publication date |
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| CN105906566B (en) | 2018-08-03 |
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