CN104262308A - Parallel six-membered ring biphenyl compound, preparation method and application thereof - Google Patents
Parallel six-membered ring biphenyl compound, preparation method and application thereof Download PDFInfo
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- CN104262308A CN104262308A CN201410383508.4A CN201410383508A CN104262308A CN 104262308 A CN104262308 A CN 104262308A CN 201410383508 A CN201410383508 A CN 201410383508A CN 104262308 A CN104262308 A CN 104262308A
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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
- C07D311/22—Benzo[b]pyrans, not hydrogenated in the carbocyclic ring with oxygen or sulfur atoms directly attached in position 4
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Abstract
The present invention discloses a parallel six-membered ring biphenyl compound (I), a preparation method and an application thereof. The preparation method is as follows: adopting tobacco whole plants as raw materials, extracting the raw materials with high-concentration methanol or high-concentration acetone/water or high-concentration ethanol/water, combining extracting solutions, carrying out filtering, concentrating the filtrate under reduced pressure to prepare an extract; loading the extract onto a column with a silica gel dry method for performing silica gel column chromatography; carrying out gradient elution with a chloroform-acetone solution, and further separating and purifying a 9:1 part of the eluent with high-pressure liquid phase chromatography to obtain the biphenyl compound. An activity test shows that the compound in the present invention has good inhibitory effects on tobacco mosaic viruses. The compound is simple in structure, has high activity, and can be taken as a pilot compound for resisting tobacco mosaic viruses.
Description
Technical field
The invention belongs to technical field of tobacco chemistry, be specifically related to a kind ofly from tobacco, extract the parallel six-ring biphenyl compound obtained first.The invention still further relates to the preparation method and application of this compound simultaneously.
Background technology
Tobacco is the plant that chemical composition is the most complicated in the world, and secondary metabolite is very abundant, 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.
Biphenyl compound is ubiquitous compound in a class natural phant, also the bibliographical information that there is this compounds is had in tobacco, biphenyl compound 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 biphenyl compound can be researched and developed further, therefrom find effective guide's chemical combination and active group.The present invention is separated and obtains a kind of parallel six-ring biphenyl compound with activity of resisting tobacco mosaic virus from tobacco, and this compound it is not yet seen relevant report.
Summary of the invention
The object of the present invention is to provide a kind of parallel six-ring biphenyl compound newly.
Another object of the present invention is to provide a kind of method preparing described parallel six-ring biphenyl compound;
The present invention also aims to provide described parallel six-ring biphenyl compound preparing the application in resisting tobacco mosaic disease medicine.
Object of the present invention is achieved by following technical proposals.
Except as otherwise noted, the percentage ratio adopted in the present invention is mass percent.
Parallel six-ring biphenyl compound of the present invention is separated to obtain from tobacco (Nicotiana tabacum), and its molecular formula is C
18h
18o
4, there is following structural formula:
This Compound nomenclature is tobacco biphenyl C, and English name is: Tababiphenyl C; For yellow jelly.
Preparing a method for described parallel six-ring biphenyl compound, take tobacco as raw material, is prepared from, specifically comprises the following steps through medicinal extract extraction, silica gel column chromatography, high pressure liquid chromatography, gel filtration chromatography:
(1) medicinal extract extracts: get tobacco sample complete stool, tobacco is pulverized or is cut into segment, be Extraction solvent with high concentration methanol (w%:80% ~ 100%) or high concentration ethanol (w%:80% ~ 100%) or high density acetone (w%:70% ~ 100%), Extraction solvent: tobacco (weight ratio)=2 ~ 4:1, soak 24h ~ 72h, extract 3 ~ 5 times, united extraction liquid, filtering and concentrating become medicinal extract;
(2) silica gel column chromatography: 80 ~ 100 order silica gel mixed samples of the pure methyl alcohol of medicinal extract weight ratio 1.5 ~ 3 times amount or straight alcohol or pure acetone dissolving rear use weight ratio 0.8 ~ 1.5 times, carries out silica gel column chromatography with 160 ~ 300 order silica gel dry column-packings of weight ratio 2 ~ 5 times amount; Carry out gradient elution with the chloroform-acetone solution that volume proportion is (1:0,9:1,8:2,7:3,6:4,1:1 and 0:1), merge identical part, collect each several part elutriant and concentrate;
(3) high pressure liquid chromatography separation and purification: namely the 9:1 part of column chromatography elutriant obtains described biphenyl compound with high pressure liquid chromatography separation and purification further.
High pressure 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 43%, and UV-detector determined wavelength is 332nm, each sample introduction 200 μ L, collects the chromatographic peak of 31.5min, repeatedly cumulative rear evaporate to dryness.
Wherein, in gel filtration chromatography step, gained compound 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.
The structure of parallel six-ring biphenyl compound of the present invention measures by the following method.This compound is yellow jelly; UV spectrum (solvent is methyl alcohol), λ
max(log ε) 213 (4.26), 267 (3.82), 332 (3.38) nm; Infrared spectra (pressing potassium bromide troche) ν
max3430,2923,2872,1675,1604,1542,1480,1435,1350,1138,962,871cm
-1; High resolution mass spectrum (HRESIMS) provides quasi-molecular ion peak m/z 321.1106 [M+Na]
+(calculated value 321.1103).In conjunction with
1h and
13c NMR spectrum provides a molecular formula C
18h
18o
4, degree of unsaturation is 10.From
1h and
13cNMR composes (attribution data is in Table-1) signal can find out that this compound is biphenyl compound, wherein obviously can find that there is an Isosorbide-5-Nitrae-dibasic phenyl ring, 1,3,4,5-tetra-substituted benzene ring, a methoxyl group.The nuclear magnetic data of the clusiparalicoline C (structure is shown in Fig. 4) of this compound of detailed comparisons and compound is very close, shows that tobacco biphenyl C is a derivative of clusiparalicoline C.
Their main difference is tobacco biphenyl C many a carbonyl, methoxyl group and a methylene radical, and lacked a pair double bond, this may be because the change of C-7 and C-8 causes.H-8 to C-7, C-4, C-9, C-10 are relevant with the HMBC of C-11 further demonstrate that this inference.In addition the HMBC of 4'-OMe to C-4' is relevant shows that methoxyl group is connected with C-4'.So far the structure of this compound is determined.
Table-1. compounds
1h NMR and
13c NMR data (CDCl
3)
Described parallel six-ring biphenyl compound is applied to the medicine preparing resisting tobacco mosaic virus.
Compared with prior art, the present invention has the following advantages:
The compounds of this invention system first from tobacco separation and Extraction obtain, determined as parallel six-ring biphenyl compound by nucleus magnetic resonance and measuring method of mass spectrum, and characterize its concrete structure.Through the experiment to resisting tobacco mosaic virus, its relative inhibition reaches 48.4%, has good activity of resisting tobacco mosaic virus, exceedes the relative inhibition (29.6%) 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 the present invention a pair of horses going side by side six-ring biphenyl compound;
Fig. 2 is the proton nmr spectra of the present invention a pair of horses going side by side six-ring biphenyl compound;
Fig. 3 is the main of the present invention a pair of horses going side by side six-ring biphenyl compound
1h-
1h COSY with HMBC is relevant.
Fig. 4 is the structure of control compounds clusiparalicoline C.
Embodiment
Below in conjunction with drawings and Examples, the present invention is described in further detail, 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.
Embodiment 1
The preparation of------compound, adopts following steps:
1, medicinal extract extracts: get tobacco sample complete stool, tobacco can be pulverized or is cut into segment, be Extraction solvent with high concentration methanol (w%:95%) or high concentration ethanol (w%:95%) or high density acetone (w%:70%), Extraction solvent: tobacco (weight ratio)=2 ~ 4:1, soak 36h, extract 4 times, united extraction liquid, filtering and concentrating become medicinal extract;
2, silica gel column chromatography: 80 ~ 100 order silica gel mixed samples of the pure methyl alcohol of medicinal extract weight ratio 2.5 times amount or straight alcohol or pure acetone dissolving rear use weight ratio 1.5 times, carries out silica gel column chromatography with 160 ~ 300 order silica gel dry column-packings of weight ratio 2.5 times amount; Carry out gradient elution with the chloroform-acetone solution that volume proportion is (1:0,9:1,8:2,7:3,6:4,1:1,0:1), merge identical part, collect each several part elutriant and concentrate;
3, high pressure liquid chromatography is separated: namely the 9:1 part of column chromatography elutriant obtains described biphenyl compound with high pressure liquid chromatography separation and purification further, and high pressure 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 43%, and UV-detector determined wavelength is 332nm, each sample introduction 200 μ L, collects the chromatographic peak of 31.5min, repeatedly cumulative rear evaporate to dryness.
4, gel filtration chromatography: the material after the separation and purification of step 3 mesohigh liquid phase chromatography is after described high performance liquid chromatography separation and purification, gained compound 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.
The present invention is raw materials used not to be limited by area and kind, all can realize the present invention, and to derive from the tobacco material of cigarette industry limited liability company Different sources in Yunnan, the present invention will be further described below:
Embodiment 2
Tobacco sample derives from Kunming, Yunnan, and kind is the large gold dollar of safflower.Tobacco is sampled 2.0kg and pulverize methanol extraction 5 times with 95%, extract 24h, extracting solution merges at every turn, and filter, concentrating under reduced pressure becomes medicinal extract, obtains medicinal extract 100g.With the thick silica gel mixed sample of 100 order of 120g after the pure dissolve with methanol of medicinal extract weight ratio 2.0 times amount, the 160 order silica gel dress posts of 0.6kg carry out silica gel column chromatography, be 1:0 with volume proportion, 9:1, 8:2, 7:3, 6:4, 1:1, chloroform-acetone the gradient elution of 0:1, 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 43% is moving phase, Zorbax SB-C18 (21.2 × 250mm, 5 μm) preparative column is stationary phase, flow velocity is 20ml/min, UV-detector determined wavelength is 332nm, each sample introduction 200 μ L, collect the chromatographic peak of 31.5min, 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 sample derives from Dali, and kind is K326, and tobacco is sampled 4.0kg chopping, the extraction using alcohol with 95% 4 times, extracts 48h at every turn, and extracting solution merges, and filter, concentrating under reduced pressure becomes medicinal extract, obtains medicinal extract 192g.With the thick silica gel mixed sample of 80 order of 200g after the pure dissolve with methanol of medicinal extract weight ratio 2.0 times amount, the 200 order silica gel dress posts of 1.2kg carry out silica gel column chromatography, be 1:0 with volume proportion, 9:1, 8:2, 7:3, 6:4, 1:1, chloroform-acetone the gradient elution of 0:1, 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 43% is moving phase, Zorbax SB-C18 (21.2 × 250mm, 5 μm) preparative column is stationary phase, flow velocity is 20ml/min, UV-detector determined wavelength is 332nm, each sample introduction 200 μ L, collect the chromatographic peak of 31.5min, 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
Tobacco sample derives from Dongzhou Period in Chuxiong, and kind is cloud and mist 200, tobacco is sampled 6kg and pulverizes, and the supersound extraction 3 times of the acetone with 75%, extracts 72h at every turn, and extracting solution merges, and filter, concentrating under reduced pressure becomes medicinal extract, obtains medicinal extract 320g.With the thick silica gel mixed sample of 90 order of 360g after the pure dissolve with methanol of medicinal extract weight ratio 1.6 times amount, the 180 order silica gel dress posts of 2.4kg carry out silica gel column chromatography, be 1:0 with volume proportion, 9:1, 8:2, 7:3, 6:4, 1:1, chloroform-acetone the gradient elution of 0:1, 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 43% is moving phase, Zorbax SB-C18 (21.2 × 250mm, 5 μm) preparative column is stationary phase, flow velocity is 20ml/min, UV-detector determined wavelength is 332nm, each sample introduction 200 μ L, collect the chromatographic peak of 31.5min, 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 5
The qualification of-------compound
Compound prepared by Example 2 is yellow jelly.UV spectrum (solvent is methyl alcohol), λ
max(log ε) 213 (4.26), 267 (3.82), 332 (3.38) nm; Infrared spectra (pressing potassium bromide troche) ν
max3430,2923,2872,1675,1604,1542,1480,1435,1350,1138,962,871cm
-1; High resolution mass spectrum (HRESIMS) provides quasi-molecular ion peak m/z 321.1106 [M+Na]
+(calculated value 321.1103).In conjunction with
1h and
13c NMR spectrum provides a molecular formula C
18h
18o
4, degree of unsaturation is 10.From
1h and
13cNMR composes (attribution data is in Table-1) signal can find out that this compound is biphenyl compound, wherein obviously can find that there is an Isosorbide-5-Nitrae-dibasic phenyl ring, 1,3,4,5-tetra-substituted benzene ring, a methoxyl group.The nuclear magnetic data of the clusiparalicoline C (structure is shown in Fig. 4) of this compound of detailed comparisons and compound is very close, shows that tobacco biphenyl C is a derivative of clusiparalicoline C.
Their main difference is tobacco biphenyl C many a carbonyl, methoxyl group and a methylene radical, and lacked a pair double bond, this may be because the change of C-7 and C-8 causes.H-8 to C-7, C-4, C-9, C-10 are relevant with the HMBC of C-11 further demonstrate that this inference.In addition the HMBC of 4'-OMe to C-4' is relevant shows that methoxyl group and C-4' love.So far the structure of this compound is determined.
Embodiment 6
Compound prepared by Example 3 is yellow jelly.Measuring method is identical with embodiment 5, confirms that compound prepared by embodiment 3 is described biphenyl compound---tobacco biphenyl C.
Embodiment 7
Compound prepared by Example 4 is yellow jelly.Measuring method is identical with embodiment 5, confirms that compound prepared by embodiment 4 is described biphenyl compound---tobacco biphenyl C.
Embodiment 8
The activity test of------resisting tobacco mosaic virus
Arbitrary biphenyl compound prepared by Example 2 ~ 4 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 50mg/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, choose the blade (leaf capable normal, anosis without worm) being applicable to test, first blade evenly sprinkled fine emery powder, with writing brush by tobacco mosaic virus (TMV) source (3.0 × 10 for subsequent use
-3) be evenly put on sprinkled with silicon carbide blade on, connect after poison terminates until the blade of all middle choosings, be placed on immediately in the culture dish filling liquid and process 20min, take out, wipe the globule and liquid on blade, being restored by two and half leaves is emitted in the glass jar being covered with toilet paper moisturizing, and cover glass cover, temperature control (23 ± 2) DEG C, be placed on greenhouse natural light irradiation, 2 ~ 3d and visible withered spot. each process set 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 48.4%, exceedes the relative inhibition 29.6% of contrast Ningnanmycin, illustrates that compound has good activity of resisting tobacco mosaic virus.
Claims (7)
1. one kind has the parallel six-ring biphenyl compound of following structural formula:
This Compound nomenclature is: tobacco biphenyl C.
2. prepare a method for parallel six-ring biphenyl compound according to claim 1, the method comprises the following steps:
(1) medicinal extract extracts: with tobacco complete stool for raw material, or is pulverized by tobacco or be cut into segment; With methyl alcohol or the ethanol of concentration expressed in percentage by weight 80% ~ 100%, or the acetone of concentration expressed in percentage by weight 70% ~ 100% is Extraction solvent, Extraction solvent: the weight ratio=2 ~ 4:1 of tobacco, soaks 24h ~ 72h, extract 3 ~ 5 times, united extraction liquid, filtering and concentrating become medicinal extract;
(2) silica gel column chromatography: 160 ~ 300 order silica gel dry column-packings of medicinal extract weight ratio 2 ~ 5 times amount carry out silica gel column chromatography; Carry out gradient elution with chloroform-acetone, merge same section, collect the elutriant of each several part and concentrate;
(3) high pressure liquid chromatography separation and purification: namely the 9:1 part of elutriant obtains required biphenyl compound with high pressure liquid chromatography separation and purification further.
3. preparation method according to claim 2, it is characterized in that: after the described high pressure liquid chromatography separation and purification of step (3), gained compound uses pure dissolve with methanol again, then with pure methyl alcohol for moving phase, be separated with gel filtration chromatography, with further separation and purification.
4. preparation method according to claim 2, is characterized in that: the high pressure liquid chromatography separation and purification of step (3) adopts 21.2mm × 250mm, the C of 5 μm
18chromatographic column, flow velocity is 20mL/min, and moving phase is the methyl alcohol of 43%, and UV-detector determined wavelength is 332nm, each sample introduction 200 μ L, collects the chromatographic peak of 31.5min, repeatedly cumulative rear evaporate to dryness.
5. preparation method according to claim 2, it is characterized in that: in step (2), described medicinal extract is before silica gel column chromatography rough segmentation, after dissolving with the pure methyl alcohol of weight ratio 1.5 ~ 3 times amount or straight alcohol or pure acetone, with 80 ~ 100 order silica gel mixed samples of weight ratio 0.8 ~ 1.5 times.
6. preparation method according to claim 2, is characterized in that: in step (2), described gradient elution, and chloroform-acetone solution volume proportion is 1:0,9:1,8:2,7:3,6:4,1:1 and 0:1.
7. parallel six-ring biphenyl compound according to claim 1 is preparing the application in resisting tobacco mosaic virus medicine.
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Cited By (2)
| Publication number | Priority date | Publication date | Assignee | Title |
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| CN105175383A (en) * | 2015-08-12 | 2015-12-23 | 云南民族大学 | Biphenyl compound and preparation method and application thereof |
| CN109438464A (en) * | 2018-11-19 | 2019-03-08 | 云南中烟工业有限责任公司 | A kind of chromone derivative and its preparation method and application extracted from short leaf Cassia |
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Cited By (3)
| Publication number | Priority date | Publication date | Assignee | Title |
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| CN105175383A (en) * | 2015-08-12 | 2015-12-23 | 云南民族大学 | Biphenyl compound and preparation method and application thereof |
| CN105175383B (en) * | 2015-08-12 | 2017-04-05 | 云南民族大学 | A kind of biphenyl compound and its preparation method and application |
| CN109438464A (en) * | 2018-11-19 | 2019-03-08 | 云南中烟工业有限责任公司 | A kind of chromone derivative and its preparation method and application extracted from short leaf Cassia |
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