CN103524472B - Phenolic compound, and preparation method and application thereof - Google Patents
Phenolic compound, and preparation method and application thereof Download PDFInfo
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- CN103524472B CN103524472B CN201310503209.5A CN201310503209A CN103524472B CN 103524472 B CN103524472 B CN 103524472B CN 201310503209 A CN201310503209 A CN 201310503209A CN 103524472 B CN103524472 B CN 103524472B
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D311/00—Heterocyclic compounds containing six-membered rings having one oxygen atom as the only hetero atom, condensed with other rings
- C07D311/02—Heterocyclic compounds containing six-membered rings having one oxygen atom as the only hetero atom, condensed with other rings ortho- or peri-condensed with carbocyclic rings or ring systems
- C07D311/04—Benzo[b]pyrans, not hydrogenated in the carbocyclic ring
- C07D311/58—Benzo[b]pyrans, not hydrogenated in the carbocyclic ring other than with oxygen or sulphur atoms in position 2 or 4
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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
- A01N43/02—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with one or more oxygen or sulfur atoms as the only ring hetero atoms
- A01N43/04—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with one or more oxygen or sulfur atoms as the only ring hetero atoms with one hetero atom
- A01N43/14—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with one or more oxygen or sulfur atoms as the only ring hetero atoms with one hetero atom six-membered rings
- A01N43/16—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with one or more oxygen or sulfur atoms as the only ring hetero atoms with one hetero atom six-membered rings with oxygen as the ring hetero atom
Abstract
The invention discloses a phenolic compound, and a preparation method and application thereof. The phenolic compound is separated from tobacco roots and stems, and has a molecular formula of C15H20NaO3 and the structure shown in the description. The tobacco roots and stems are taken as raw materials, and the preparation method for the phenolic compound comprises the steps of extract extraction, silica-gel column chromatography and high-pressure liquid chromatographic analysis, and specifically comprises the following steps of performing ethanol ultrasonic extraction after the tobacco roots and stems are crushed, mixing and filtering an extracting solution, and concentrating the extracting solution into extract under reduced pressure; filling the extract into a column for silica-gel column chromatography by using a silica gel dry method; performing gradient elution according to a chloroform-acetone solution in a volume ratio of (1:0)-(1:2); further performing high-pressure liquid chromatographic analysis and purification on the 9:1 part of eluent to obtain the phenolic compound. Tests show that the phenolic compound has higher cell activity to tobacco mosaic viruses; the compound is simple in structure, easy to artificially synthesize and high in activity, and can be used for resisting the tobacco mosaic viruses as a pilot compound.
Description
Technical field
The invention belongs to tobacco chemistry field, be specifically related to a kind of phenolic compound extracted from tobacco rhizome and preparation method thereof and application.
Background technology
Tobacco is one the abundantest containing chemical substance in each kind of plant of being familiar with of the mankind, and through the research of decades, the monomer chemistries material that people identify out at present from tobacco just more than kind more than 3000, and also has many compositions not yet to identify out.Tobacco, except being mainly used in cigarette smoking purposes, also therefrom can extract the multiple chemical composition having utility value, therefrom finds that there is the guiding compound of value of exploiting and utilizing.Particularly for the root of tobacco and stem, general all as the offal treatment in leaf tobacco production process.Therefore, except as except cigarette consumption, the comprehensive utilization strengthening tobacco and waste thereof is significant.
Phenolic compound is ubiquitous compound in a class natural phant, also be the important component in tobacco, this compounds has pharmacological action widely, as antitumor, anti-human immunodeficiency virus (HIV), anti-oxidant, antibacterial, anticoagulation etc.; Existing research simultaneously confirms, its pharmacological action and chemical structure closely related, more phenolic compound can be researched and developed further, therefrom find effective lead compound and active group.The present invention is separated and obtains a kind of new phenolic compound with activity of resisting tobacco mosaic virus from tobacco rhizome, and this compound it is not yet seen relevant report.
Summary of the invention
The first object of the present invention is to provide a kind of phenolic compound; Second object is the preparation method providing described phenolic compound; 3rd object is to provide described phenolic compound preparing the application in resisting tobacco mosaic disease medicine.
The first object of the present invention is achieved in that described compound is separated to obtain from tobacco rhizome, and its molecular formula is C
15h
20naO
3, there is following structure:
This compound is yellow jelly, and chemical name is 1-(5-methoxyl group-2,2-dimethyl-3,4-dihydro-2
h-chromene-7-base)-2-acetone (1-(5-methoxy-2,2-dimethyl-3,4-dihydro-2
h-chromen-7-yl) propan-2-one).
It take tobacco rhizome as raw material that the second object of the present invention is achieved in that the preparation method of described phenolic compound is, through medicinal extract extraction, silica gel column chromatography, high pressure liquid chromatography separating step, is specially:
A, medicinal extract extract: get tobacco rhizome sample, be crushed to 20 ~ 40 orders, with 90 ~ 99% ethanol ultrasonic extraction 3 ~ 5 times, and each 30 ~ 60 min, united extraction liquid, filtration, concentrating under reduced pressure becomes medicinal extract;
B, silica gel column chromatography: 160 ~ 200 order silica gel dry column-packings of medicinal extract weight ratio 2 ~ 3 times amount carry out silica gel column chromatography; Be that the chloroform-acetone solution of 1:0 ~ 1:2 carries out gradient elution with volume proportion, merge identical part, collect each several part elutriant and concentrated;
C, high pressure liquid chromatography are separated: namely the 9:1 part of step B elutriant obtains described phenolic compound with high pressure liquid chromatography separation and purification further.
The structure of the phenolic compound prepared with aforesaid method measures out by the following method:
The compounds of this invention is yellow jelly; UV spectrum (solvent is methyl alcohol),
λ max(log ε) 210 (4.26), 250 (3.76), 330 (2.87); Infrared spectra (pressing potassium bromide troche)
ν max3416,2918,2854,1716,1606,1542,1427,1387,1161,956,815 cm
-1; High resolution mass spectrum (HRESIMS) provides quasi-molecular ion peak m/z 271.1317 [M+Na]
+(calculated value 271.1310).In conjunction with
1h and
13c NMR spectrum provides a molecular formula C
15h
20naO
3, degree of unsaturation is 6.From
1h and
13cNMR compose (attribution data is in Table-1) signal can find out in compound have one 5,7-to replace dihydro chromene parent (
δ c73.2 s, 33.4 t, 21.4 t, 162.9 s, 112.0 d, 134.1 s, 108.9 d, 152.1 s, 115.2 s, 26.8 q (2C);
δ h1.78 2H (t)
j=6.8,2.64 2H (t)
j=6.8,6.62 1H (d)
j=2.2,6.44 (d)
j=1.8,1.62 6H s), acetonyl (
δ c49.2 t, 206.2 s, 31.0 q;
δ h4.15 2H s, 2.43 3H s), and methoxyl group (
δ c56.0 q,
δ h3.80 3H s), according to H-11 and C-6, C-7, C-8, and H-6, H-8 susceptible of proof acetonyl relevant with the HMBC of C-11 is substituted in C-7 position, according to methoxyl group hydrogen susceptible of proof methoxy substitution relevant with the HMBC of C-5 in C-5 position.So far the structure of compound is confirmed.
Table-1. compounds
1h NMR and
13c NMR data (C
5d
5n)
| No. | d C (m) | d H (m, J, Hz) |
| 2 | 73.2 s | |
| 3 | 33.4 t | 1.78 (t) 6.8 |
| 4 | 21.4 t | 2.64 (t) 6.8 |
| 5 | 162.9 s | |
| 6 | 112.0 d | 6.62 (d) 2.2 |
| 7 | 134.1 s | |
| 8 | 108.9 d | 6.44 (d) 2.2 |
| 9 | 152.1 s | |
| 10 | 115.2 s | |
| 11 | 49.2 t | 4.15 s |
| 12 | 206.2 s | |
| 13 | 31.0 q | 2.43 s |
| 14,15 | 26.8 q | 1.62 s |
| 5-OMe | 56.0 q | 3.80 s |
The third object of the present invention is achieved in that the preparation be applied to by described phenolic compound in Tobacco mosaic medicine.
The compounds of this invention is separated first, is determined as phenolic compound by nucleus magnetic resonance and measuring method of mass spectrum, and characterizes its concrete structure.Through the experiment to resisting tobacco mosaic virus, its relative inhibition reaches 38.5%, has good activity of resisting tobacco mosaic virus, higher than the relative inhibition (28.2%) of positive reference substance Nanning mycin.Above result discloses compound of the present invention preparing in resisting tobacco mosaic virus medicine good application prospect.The compounds of this invention structure is simple active good, can be used as the guiding compound of resisting tobacco mosaic virus medicine.
Accompanying drawing explanation
Fig. 1 is the carbon-13 nmr spectra of compound;
Fig. 2 is the proton nmr spectra of compound;
Fig. 3 is that the main HMBC of compound is correlated with.
Embodiment
Below in conjunction with embodiment and accompanying drawing, the present invention is further illustrated, but limited the present invention never in any form, and any conversion done based on training centre of the present invention or improvement, all fall into protection scope of the present invention.
Except as otherwise noted, the percentage ratio adopted in the present invention is mass percent.
Phenolic compound C of the present invention
15h
20naO
3preparation method comprise medicinal extract extraction, silica gel column chromatography, high pressure liquid chromatography separating step, specifically comprise:
A, medicinal extract extract: get tobacco rhizome sample, be crushed to 20 ~ 40 orders, with 90 ~ 99% ethanol ultrasonic extraction 3 ~ 5 times, and each 30 ~ 60 min, united extraction liquid, filtration, concentrating under reduced pressure becomes medicinal extract;
B, silica gel column chromatography: 160 ~ 200 order silica gel dry column-packings of medicinal extract weight ratio 2 ~ 3 times amount carry out silica gel column chromatography; Be that the chloroform-acetone solution of 1:0 ~ 1:2 carries out gradient elution with volume proportion, merge identical part, collect each several part elutriant and concentrated;
C, high pressure liquid chromatography are separated: namely the 9:1 part of step B elutriant obtains described phenolic compound with high pressure liquid chromatography separation and purification further.
The etoh solvent concentration of described step A is 95%.
The medicinal extract of described step B before silica gel column chromatography rough segmentation, with after the pure dissolve with methanol of weight ratio 1.5 ~ 3 times amount with 80 ~ 100 order silica gel mixed samples of weight ratio 0.8 ~ 1.2 times.
The chloroform-acetone solution volume proportion of described step B is 1:0,20:1,9:1,8:2,7:3,6:4,1:1,1:2.
Described step C mesohigh liquid chromatography separation and purification is employing 21.2 mm × 250 mm, 5
μthe C of m
18chromatographic column, flow velocity is 20 mL/min, and moving phase is the methyl alcohol of 65%, and UV-detector determined wavelength is 352 nm, each sample introduction 200
μl, collects the chromatographic peak of 18.6 min, repeatedly cumulative rear evaporate to dryness.
Material after the separation and purification of described step C mesohigh liquid phase chromatography uses pure dissolve with methanol again, then with pure methyl alcohol for moving phase, is separated with gel filtration chromatography, with further separation and purification.
Phenolic compound of the present invention is preparing the application in resisting tobacco mosaic virus medicine.
The present invention is raw materials used not to be limited by area and kind, and all can realize the present invention, to derive from the tobacco rhizome sample of Yunnan Yuxi, the present invention will be further described below:
embodiment 1
Tobacco rhizome sample source is in Yunnan Yuxi, and kind is cloud and mist-85.Tobacco rhizome is sampled 2.2 kg and be crushed to 30 orders, the supersound extraction 3 times of the ethanol with 95%, extracts 30min at every turn, and extracting solution merges, and filter, concentrating under reduced pressure becomes medicinal extract, obtains medicinal extract 105.4 g.With the thick silica gel mixed sample of 100 order of 150 g after the pure dissolve with methanol of medicinal extract weight ratio 2.5 times amount, the 160 order silica gel dress posts of 1.5 kg carry out silica gel column chromatography, be 1:0 with volume proportion, 20:1, 9:1, 8:2, 7:3, 6:4, 1:1, chloroform-acetone the gradient elution of 1:2, TLC monitoring merges identical part, obtain 8 parts, wherein volume proportion is the prompt logical sequence 1,100 half preparative high-performance liquid chromatographic separation of chloroform-acetone elution fraction peace of 9:1, methyl alcohol with 65% is moving phase, Zorbax SB-C18 (21.2 ' 250 mm, 5 mm) preparative column is stationary phase, flow velocity is 20 ml/min, UV-detector determined wavelength is 352 nm, each sample introduction 200 mL, collect the chromatographic peak of 18.6 min, repeatedly cumulative rear evaporate to dryness, products therefrom uses pure dissolve with methanol again, then with pure methyl alcohol for moving phase, is separated, obtains this new compound with Sephadex LH-20 gel filtration chromatography.
embodiment 2
Tobacco rhizome sample source is in Yunnan Yuxi, and kind is cloud and mist-85.Tobacco rhizome is sampled 3.5kg and be crushed to 40 orders, the supersound extraction 5 times of the ethanol with 90%, extract 45 min at every turn, extracting solution merges, and filter, concentrating under reduced pressure becomes medicinal extract, obtains medicinal extract 215 g.With the thick silica gel mixed sample of 80 order of 300 g after the pure dissolve with methanol of medicinal extract weight ratio 2.0 times amount, the 200 order silica gel dress posts of 1.5 kg carry out silica gel column chromatography, be 1:0 with volume proportion, 20:1, 9:1, 8:2, 7:3, 6:4, 1:1, chloroform-acetone the gradient elution of 1:2, TLC monitoring merges identical part, obtain 8 parts, wherein volume proportion is the prompt logical sequence 1,100 half preparative high-performance liquid chromatographic separation of chloroform-acetone elution fraction peace of 9:1, methyl alcohol with 65% is moving phase, Zorbax SB-C18 (21.2 ' 250 mm, 5 mm) preparative column is stationary phase, flow velocity is 20 ml/min, UV-detector determined wavelength is 352 nm, each sample introduction 200 mL, collect the chromatographic peak of 18.6 min, repeatedly cumulative rear evaporate to dryness, products therefrom uses pure dissolve with methanol again, then with pure methyl alcohol for moving phase, is separated, obtains this new compound with Sephadex LH-20 gel filtration chromatography.
embodiment 3
Tobacco rhizome sample source is in Yunnan Yuxi, and kind is cloud and mist-85.Tobacco rhizome is sampled 5 kg and be crushed to 60 orders, the supersound extraction 3 times of the ethanol with 99%, extract 60 min at every turn, extracting solution merges, and filter, concentrating under reduced pressure becomes medicinal extract, obtains medicinal extract 312 g.With the thick silica gel mixed sample of 90 order of 500 g after the pure dissolve with methanol of medicinal extract weight ratio 1.6 times amount, the 180 order silica gel dress posts of 1.8 kg carry out silica gel column chromatography, be 1:0 with volume proportion, 20:1, 9:1, 8:2, 7:3, 6:4, 1:1, chloroform-acetone the gradient elution of 1:2, TLC monitoring merges identical part, obtain 8 parts, wherein volume proportion is the prompt logical sequence 1,100 half preparative high-performance liquid chromatographic separation of chloroform-acetone elution fraction peace of 9:1, methyl alcohol with 65% is moving phase, Zorbax SB-C18 (21.2 ' 250 mm, 5 mm) preparative column is stationary phase, flow velocity is 20 ml/min, UV-detector determined wavelength is 352 nm, each sample introduction 200 mL, collect the chromatographic peak of 18.6 min, repeatedly cumulative rear evaporate to dryness, products therefrom uses pure dissolve with methanol again, then with pure methyl alcohol for moving phase, is separated, obtains this new compound with Sephadex LH-20 gel filtration chromatography.
embodiment 4
Compound prepared by Example 1 is yellow jelly.
Measuring method is: with nucleus magnetic resonance, in conjunction with other spectroscopic technique qualification structure.
The compounds of this invention is yellow jelly; UV spectrum (solvent is methyl alcohol),
λ max(log ε) 210 (4.26), 250 (3.76), 330 (2.87); Infrared spectra (pressing potassium bromide troche)
ν max3416,2918,2854,1716,1606,1542,1427,1387,1161,956,815 cm
-1; High resolution mass spectrum (HRESIMS) provides quasi-molecular ion peak m/z 271.1317 [M+Na]
+(calculated value 271.1310).In conjunction with
1h and
13c NMR spectrum provides a molecular formula C
15h
20naO
3, degree of unsaturation is 6.From
1h and
13cNMR compose (attribution data is in Table-1) signal can find out in compound have one 5,7-to replace dihydro chromene parent (
δ c73.2 s, 33.4 t, 21.4 t, 162.9 s, 112.0 d, 134.1 s, 108.9 d, 152.1 s, 115.2 s, 26.8 q (2C);
δ h1.78 2H (t)
j=6.8,2.64 2H (t)
j=6.8,6.62 1H (d)
j=2.2,6.44 (d)
j=1.8,1.62 6H s), acetonyl (
δ c49.2 t, 206.2 s, 31.0 q;
δ h4.15 2H s, 2.43 3H s), and methoxyl group (
δ c56.0 q,
δ h3.80 3H s), according to H-11 and C-6, C-7, C-8, and H-6, H-8 susceptible of proof acetonyl relevant with the HMBC of C-11 is substituted in C-7 position, according to methoxyl group hydrogen susceptible of proof methoxy substitution relevant with the HMBC of C-5 in C-5 position.So far the structure of compound is confirmed.
embodiment 5
Compound prepared by Example 2 is yellow jelly.Measuring method is identical with embodiment 4, confirms that compound prepared by embodiment 2 is described phenolic compound---1-(5-methoxyl group-2,2-dimethyl-3,4-dihydro-2
h-chromene-7-base)-2-acetone.
embodiment 6
Compound prepared by Example 3 is yellow jelly.Measuring method is identical with embodiment 4, confirms that compound prepared by embodiment 3 is described phenolic compound---1-(5-methoxyl group-2,2-dimethyl-3,4-dihydro-2
h-chromene-7-base)-2-acetone.
embodiment 7
Arbitrary phenolic compound prepared by Example 1 ~ 3 carries out activity of resisting tobacco mosaic virus test, and test situation is as follows:
Adopt half leaf method, when the mass concentration of medicament is 50 mg/L, activity of resisting tobacco mosaic virus mensuration is carried out to the compounds of this invention.5 ~ 6 age flue-cured tobacco plant on, (leaf is capable normal to choose the blade being applicable to test, anosis without worm), first blade is evenly sprinkled fine emery powder, with writing brush, tobacco mosaic virus (TMV) source (3.0 × 10-3) for subsequent use is evenly put on the blade sprinkled with silicon carbide, connect after poison terminates until the blade of all middle choosings, be placed on immediately in the culture dish filling liquid and process 20 min, take out, to spill on defoliation sheet the globule and about liquid, two and half leaves are restored and is emitted on the enamel son of an influential official cover glass being covered with toilet paper moisturizing, temperature control (23 ± 2) DEG C, be placed on greenhouse natural light irradiation, 2 ~ 3 d and visible withered spot. each process sets second half leaf as contrast, be provided with in addition 1 group be the process of commodity Ningnanmycin as a comparison, press formulae discovery relative inhibition.
XI％=(CK-T)／CK×100％
X: relative inhibition (%), CK: be soaked in the withered spot number (individual) that half in clear water connects malicious leaf, T is soaked in the withered spot number (individual) that half in liquid connects malicious leaf.
The relative inhibition of result bright compound is 38.5%, far above the relative inhibition 28.2% of contrast Ningnanmycin, illustrates that compound has good activity of resisting tobacco mosaic virus.
Claims (5)
1. a preparation method for phenolic compound, is characterized in that its molecular formula of described phenolic compound is C
15h
20o
3, there is following structure:
；
Described phenolic compound take tobacco rhizome as raw material, through medicinal extract extraction, silica gel column chromatography, high pressure liquid chromatography separating step, is specially:
A, medicinal extract extract: get tobacco rhizome sample, be crushed to 20 ~ 40 orders, with 90 ~ 99% ethanol ultrasonic extraction 3 ~ 5 times, and each 30 ~ 60 min, united extraction liquid, filtration, concentrating under reduced pressure becomes medicinal extract;
B, silica gel column chromatography: 160 ~ 200 order silica gel dry column-packings of medicinal extract weight ratio 2 ~ 3 times amount carry out silica gel column chromatography; Be that the chloroform-acetone solution of 1:0,20:1,9:1,8:2,7:3,6:4,1:1,1:2 carries out gradient elution with volume proportion, merge identical part, collect each several part elutriant and concentrated;
C, high pressure liquid chromatography are separated: namely the 9:1 part of step B elutriant obtains described phenolic compound with high pressure liquid chromatography separation and purification further.
2. the preparation method of phenolic compound as claimed in claim 1, is characterized in that in described step A, alcohol concn is 95%.
3. the preparation method of phenolic compound as claimed in claim 1, is characterized in that in described step B, medicinal extract is before silica gel column chromatography rough segmentation, with 80 ~ 100 order silica gel mixed samples by weight ratio 0.8 ~ 1.2 times after the pure dissolve with methanol of weight ratio 1.5 ~ 3 times amount.
4. the preparation method of phenolic compound as claimed in claim 1, is characterized in that: described step C mesohigh liquid chromatography separation and purification adopts 21.2mm × 250mm, the C of 5 μm
18chromatographic column, flow velocity is 20mL/min, and moving phase is the methyl alcohol of 65%, and UV-detector determined wavelength is 352nm, each sample introduction 200 μ L, collects the chromatographic peak of 18.6min, repeatedly cumulative rear evaporate to dryness.
5. the preparation method of phenolic compound as claimed in claim 1, it is characterized in that the material after the separation and purification of described step C mesohigh liquid chromatography uses pure dissolve with methanol again, again with pure methyl alcohol for moving phase, with gel filtration chromatography be separated, with further separation and purification.
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| MD4299C1 (en) * | 2013-09-16 | 2015-03-31 | Институт Генетики И Физиологии Растений Академии Наук Молдовы | Process for producing antioxidant compounds from walnut kernel skin (Juglans regia L.) |
| CN104370726B (en) * | 2014-08-06 | 2016-02-24 | 云南中烟工业有限责任公司 | A kind of biphenyl compound with isohexyl side chain and its preparation method and application |
| CN104292203B (en) * | 2014-09-16 | 2016-02-10 | 云南民族大学 | A kind of Isocoumarin compounds and its preparation method and application |
| CN106883243B (en) * | 2017-02-14 | 2018-11-27 | 云南民族大学 | It is a kind of with the isobenzofuran class compound and its tobacco purposes of removing free radical effect in pueraria lobata |
| CN109908228A (en) * | 2019-03-06 | 2019-06-21 | 贵州省烟草科学研究院 | The extracting method and its application of tobacco antitumor component |
| CN114456102A (en) * | 2022-01-27 | 2022-05-10 | 云南中烟工业有限责任公司 | Indole alkaloid compound and preparation method and application thereof |
| CN115677473B (en) * | 2022-11-16 | 2023-12-12 | 广东一方制药有限公司 | Phenolic compound, method for extracting and separating phenolic compound from medulla Tetrapanacis and application of phenolic compound |
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