CN102977059B - Phenylpropanoid compound, and preparation method and application thereof - Google Patents
Phenylpropanoid compound, and preparation method and application thereof Download PDFInfo
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- CN102977059B CN102977059B CN201210518939.8A CN201210518939A CN102977059B CN 102977059 B CN102977059 B CN 102977059B CN 201210518939 A CN201210518939 A CN 201210518939A CN 102977059 B CN102977059 B CN 102977059B
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Abstract
The invention discloses a phenylpropanoid compound, and a preparation method and application thereof. The phenylpropanoid compound is separated from tobacco and has a structure shown in the specification, wherein R represents hydrogen or methyl. The preparation method of the phenylpropanoid compound comprises the steps of extraction, silica gel column chromatography and separation through high-pressure liquid chromatography, and comprises the following specific steps: pulverizing a plant sample, extracting, filtering, concentrating to obtain an extract, performing chromatography, eluting, concentrating, and performing further separation and purification on the (8:2) part to obtain the phenylpropanoid compound. The phenylpropanoid compound can be applied in the preparation of antitumor drugs for inhibiting human bone marrow neuroblastoma cell strains SHSY5Y. According to the invention, the compound is simple in structure and favorable in antitumor activity and can be artificially synthesized easily; and the compounds 1 and 2 show remarkable inhibition activity on SHSY5Y tumor cell strains, and the corresponding IC50 (half maximal inhibitory concentration) values are respectively 1.5 and 2.2 mu M.
Description
Technical field
The invention belongs to vegetable chemistry technical field, be specifically related to a kind of plant that derives from, especially derive from the Phenylpropanoid Glycosides compound and preparation method thereof and application of tobacco.
Background technology
Tobacco be in each kind of plant of being familiar with of the mankind containing maximum a kind of of chemical substance, through the research of decades, people identify that monomer chemical substance out just surpasses kind more than 3000 at present from tobacco, and also have many compositions not yet to identify out.Tobacco, except supplying to suck mainly for the production of cigarette, also can therefrom be extracted the multiple chemical composition that has utility value, therefrom finds that there is the guiding compound of value of exploiting and utilizing.Therefore, except as cigarette consumption, the research of strengthening other purposes of tobacco is also significant.
Turkish tobaccos You Cheng Turkey cigarette, east type cigarette, originate in Mediterranean country, be safflower tobacco (
nicotiana tobacum) a kind of special tobacco type.Because Turkish tobaccos have strong fragrance and pure jealous quality characteristic, it is one of important source material of production mixed type, outer odor type and oriental type cigarette and pipe tobacco.In China, Turkish tobaccos have establishing in large scale at Baoshan, Yunnan at present.
Phenylpropanoid Glycosides is the biologically active substance that a class occurring in nature extensively exists.Because plant Phenylpropanoid Glycosides constituent structure type is many, stereochemistry is complicated, has multiple biological activity, very active to the research in this field both at home and abroad; No matter be naturally occurring, or the phenylpropanoids that obtains of synthetic, chemist's extensive concern all caused.
Summary of the invention
The object of the present invention is to provide a kind of Phenylpropanoid Glycosides compound; The second object is to provide the preparation method of described Phenylpropanoid Glycosides compound; The 3rd object is to provide described Phenylpropanoid Glycosides compound preparing the application in the antitumor drug of people's marrow neuroblastoma cell line SHSY5Y.
The first object of the present invention is achieved in that the separation from tobacco of described Phenylpropanoid Glycosides compound obtains, and has following structure:
Wherein, R represents hydrogen, methyl.
The present invention's the second object is achieved in that and comprises extraction, silica gel column chromatography, high pressure liquid chromatography separating step, specifically comprises:
A, extraction: plant sample is crushed to 20 ~ 40 orders, the methyl alcohol supersound extraction with 70 ~ 99% 3 ~ 5 times, extracting solution merges, and filters, and concentrating under reduced pressure becomes medicinal extract;
B, silica gel column chromatography: medicinal extract carries out silica gel column chromatography with 200 ~ 300 order silica gel dress posts of 5 ~ 10 times of amounts of weight ratio, and the chloroform-methanol solution that the volume proportion of take is 20:1 ~ 1:1 carries out gradient elution, merges identical part, collects each several part elutriant concentrated;
C, high pressure liquid chromatography separation: the 8:2 part of B step further obtains described Phenylpropanoid Glycosides compound with high pressure liquid chromatography separation and purification.
The structure of the Phenylpropanoid Glycosides compound of preparing with aforesaid method is to measure out by the following method:
The compounds of this invention
1for yellow jelly end; UV spectrum (solvent is methyl alcohol), λ
max(log
ε) 312 (3.88), 260 (4.02), 250 (4.46) nm; Infrared spectra (pressing potassium bromide troche) ν
max3365,2958,2876,1720,1708,1625,1510,1455,1420,1258,1172,1040,955,870 cm
-1; High resolution mass spectrum (HRESIMS) provides quasi-molecular ion peak m/z 377.0879 [M-H]
-(calculated value 377.0873).In conjunction with
1h and
13c NMR spectrum provides a molecular formula C
18h
18o
9, degree of unsaturation is 10.From
1h and
13cNMR spectrum (figure-1 and figure-2, attribution data is in Table-1) signal can be found out compound
1have outside the parent nucleus of a furans cinnamic acid, also have the substituting group of 1 shikimic acid.This compound
1be named as
nicotfuranA, molecular formula is C
18h
18o
9, its structure is:
The compounds of this invention
2for yellow jelly end; UV spectrum (solvent is methyl alcohol),
λ max(log
ε) 328 (3.82), 262 (3.97), 210 (4.48) (4.15) nm; Infrared spectra (pressing potassium bromide troche)
ν max3362 2955,2872,1722,1705,1623,1510,1458,1422,1263,1174,1054,953,875 cm
-1; High resolution mass spectrum (HRESIMS) provides quasi-molecular ion peak m/z 391.1029 [M-H]
-(calculated value 391.1022).In conjunction with
1h and
13c NMR spectrum provides a molecular formula C
19h
20o
9, degree of unsaturation is 10.From
1h and
13cNMR spectrum (figure-3 and figure-4, attribution data is in Table-1) signal can find out that compound 2 and compound 1 are similar, compound 2 just how a methoxyl group signal.This compound
2be named as
nicotfuranB,molecular formula is C
19h
20o
9, its structure is:
table-1 compound 1,2
1
h and
13
c NMR data
Phenylpropanoid Glycosides compound described in the present invention's the 3rd object is achieved in that is being prepared the application in the antitumor drug of people's marrow neuroblastoma cell line SHSY5Y.
Phenylpropanoid Glycosides compound of the present invention is separated first from tobacco, has determined for Phenylpropanoid Glycosides compound, and characterized its concrete mechanism by nucleus magnetic resonance and measuring method of mass spectrum.The compounds of this invention is simple in structure, and synthetic is easily realized, and anti-tumor activity is good, compound
1,
2sHSY5Y tumor cell line is demonstrated to obvious inhibition active, corresponding IC
50value is respectively 1.5 and 2.2
μm.
Accompanying drawing explanation
Fig. 1 be the compounds of this invention 1 proton nmr spectra (
1h NMR) figure;
Fig. 2 be the compounds of this invention 1 carbon-13 nmr spectra (
13c NMR) figure;
Fig. 3 is the hsqc spectrum figure of the compounds of this invention 1;
Fig. 4 is the HMBC spectrogram of the compounds of this invention 1;
Fig. 5 is the high resolution mass spectrum figure of the compounds of this invention 1;
Fig. 6 be the compounds of this invention 2 proton nmr spectra (
1h NMR) figure;
Fig. 7 be the compounds of this invention 2 carbon-13 nmr spectra (
13c NMR) figure;
Fig. 8 is the main HMBC correlogram of the compounds of this invention 1 and 2.
Embodiment
Below in conjunction with accompanying drawing, the present invention is further illustrated, but never in any form the present invention is limited, and any conversion or the replacement based on training centre of the present invention, done, all belong to protection scope of the present invention.
Phenylpropanoid Glycosides Compound C of the present invention
18h
18o
9, C
19h
20o
9preparation method, comprise extraction, silica gel column chromatography, high pressure liquid chromatography separating step, specifically comprise:
Extraction is that plant sample is crushed to 20 ~ 40 orders, the methyl alcohol supersound extraction with 70 ~ 99% 3 ~ 5 times, and extracting solution merges, and filters, and concentrating under reduced pressure becomes medicinal extract;
Silica gel column chromatography is that medicinal extract carries out silica gel column chromatography with 200 ~ 300 order silica gel dress posts of 5 ~ 10 times of amounts of weight ratio, and the chloroform-methanol solution that the volume proportion of take is 20:1 ~ 1:1 carries out gradient elution, merges identical part, collects each several part elutriant concentrated;
The 8:2 part that high pressure liquid chromatography is separated into silica gel column chromatography step further obtains described Phenylpropanoid Glycosides compound with high pressure liquid chromatography separation and purification.
In described extraction step, methanol concentration is 85 ~ 95%.
In described extraction step, the supersound extraction time is 30 ~ 60 min.
In described silica gel column chromatography step, medicinal extract is before silica gel column chromatography rough segmentation, with 90 ~ 99% dissolve with methanol of 1.5 ~ 3 times of amounts of weight ratio, with weight ratio be the thick silica gel mix and blend of 80 ~ 100 order of 0.25 ~ 0.5 times, further remove impurity.
In described silica gel column chromatography step, chloroform-methanol liquor capacity proportioning is 20:1,9:1,8:2,7:3,6:4,5:5.
Described high pressure liquid chromatography separating step mesohigh liquid chromatography separation and purification is to adopt 20 mm * 250 mm, the C of 5 μ m
18chromatographic column, flow velocity is 12 mL/min, the methanol-water that the volume proportion of take is 40:60 ~ 50:50 is moving phase.
Described moving phase is the methanol-water solution of volume proportion 50:50.
Material after described high pressure liquid chromatography separating step mesohigh liquid phase chromatography separation and purification is used pure dissolve with methanol again, take pure methyl alcohol as moving phase, separated with Sephadex LH-20 gel filtration chromatography, with further separation and purification.
The described Phenylpropanoid Glycosides compound that is applied as of Phenylpropanoid Glycosides compound of the present invention is being prepared the application in the antitumor drug of people's marrow neuroblastoma cell line SHSY5Y.
Raw materials used area and the kind of not being subject to of tobacco of the present invention limits, and all can realize the present invention, and to derive from the Turkish tobaccos sample of Baoshan, Yunnan, the present invention will be further described below:
Embodiment 1
Turkish tobaccos sample is adopted in Baoshan, Yunnan, and kind is Bath horse.Turkish tobaccos complete stool sampling 1.5kg is crushed to 20 orders, the methyl alcohol supersound extraction with 70% 5 times, each 30 minutes, extracting solution merged, filters, and concentrating under reduced pressure becomes medicinal extract, obtains medicinal extract 160 g.After 90% dissolve with methanol that medicinal extract use weight ratio is 1.5 times, with the thick silica gel mixed sample of 100 order of 80 g, the 300 order silica gel dress posts of 1.5 kg carry out silica gel column chromatography.Chloroform-methanol is pressed respectively 20:1,9:1, and 8:2,7:3,6:4, the volume proportion of 5:5, carries out gradient elution, collects various piece elutriant concentrated; The 8:2 part of elutriant is further used high pressure lipuid chromatography (HPLC) separation and purification, and the methanol-water of 40:60 of take is moving phase, adopts 20 mm * 250 mm, the C of 5 μ m
18preparative column is stationary phase, and flow velocity is 10 mL/min, and it is 254 nm that UV-detector detects wavelength, each sample introduction 200 μ L, the chromatographic peak of collection 15.5 min, repeatedly cumulative rear evaporate to dryness; Gained material is used pure dissolve with methanol again, then take pure methyl alcohol as moving phase, separated with Sephadex LH-20 gel filtration chromatography, gets final product to obtain target compound.
Embodiment 2
Turkish tobaccos sample is adopted in Baoshan, Yunnan, and kind is Bath horse.Turkish tobaccos complete stool is sampled to 2.5 kg and be crushed to 40 orders, the methyl alcohol supersound extraction with 85% 5 times, each 40 minutes, extracting solution merged, filters, and concentrating under reduced pressure becomes medicinal extract, obtains medicinal extract 220 g.After 99% dissolve with methanol that medicinal extract use weight ratio is 3 times, with the thick silica gel mixed sample of 80 order of 100 g, the 200 order silica gel dress posts of 2.0 kg carry out silica gel column chromatography.Chloroform-methanol is pressed respectively 20:1,9:1, and 8:2,7:3,6:4, the volume proportion of 5:5, carries out gradient elution, collects various piece elutriant concentrated; The 8:2 part of elutriant is further used high pressure lipuid chromatography (HPLC) separation and purification, and the methanol-water of 50:50 of take is moving phase, adopts 20 mm * 250 mm, the C of 5 μ m
18preparative column is stationary phase, and flow velocity is 12 mL/min, and it is 254 nm that UV-detector detects wavelength, each sample introduction 200 μ L, the chromatographic peak of collection 14.5 min, repeatedly cumulative rear evaporate to dryness; Gained material is used pure dissolve with methanol again, then take pure methyl alcohol as moving phase, separated with Sephadex LH-20 gel filtration chromatography, gets final product to obtain target compound.
Embodiment 3
Turkish tobaccos sample is adopted in Baoshan, Yunnan, and kind is Bath horse.Turkish tobaccos complete stool is sampled to 2.0 kg and be crushed to 30 orders, the methyl alcohol supersound extraction with 90% 4 times, each 60 minutes, extracting solution merged, filters, and concentrating under reduced pressure becomes medicinal extract, obtains medicinal extract 195 g.After 95% dissolve with methanol that medicinal extract use weight ratio is 2.5 times, with the thick silica gel mixed sample of 90 order of 90 g, the 300 order silica gel dress posts of 1.8 kg carry out silica gel column chromatography.Chloroform-methanol is pressed respectively 20:1,9:1, and 8:2,7:3,6:4, the volume proportion of 5:5, carries out gradient elution, collects various piece elutriant concentrated; The 8:2 part of elutriant is further used high pressure lipuid chromatography (HPLC) separation and purification, and the methanol-water of 40:60 of take is moving phase, adopts 20 mm * 250 mm, the C of 5 μ m
18preparative column is stationary phase, and flow velocity is 14 mL/min, and it is 254 nm that UV-detector detects wavelength, each sample introduction 200 μ L, the chromatographic peak of collection 14.9 min, repeatedly cumulative rear evaporate to dryness; Gained material is used pure dissolve with methanol again, then take pure methyl alcohol as moving phase, separated with Sephadex LH-20 gel filtration chromatography, gets final product to obtain target compound.
Embodiment 4
Turkish tobaccos sample is adopted in Baoshan, Yunnan, and kind is Bath horse.Turkish tobaccos complete stool is sampled to 2.5 kg and be crushed to 40 orders, the methyl alcohol supersound extraction with 95% 4 times, each 50 minutes, extracting solution merged, filters, and concentrating under reduced pressure becomes medicinal extract, obtains medicinal extract 210 g.After 99% dissolve with methanol that medicinal extract use weight ratio is 1.5 ~ 3 times, with the thick silica gel mixed sample of 80 order of 100 g, the 300 order silica gel dress posts of 1.8 kg carry out silica gel column chromatography.Chloroform-methanol is pressed respectively 20:1,9:1, and 8:2,7:3,6:4, the volume proportion of 5:5, carries out gradient elution, collects various piece elutriant concentrated; The 8:2 part of elutriant is further used high pressure lipuid chromatography (HPLC) separation and purification, and the methanol-water of 40:60 ~ 50:50 of take is moving phase, adopts 20 mm * 250 mm, the C of 5 μ m
18preparative column is stationary phase, and flow velocity is 15 mL/min, and it is 254 nm that UV-detector detects wavelength, each sample introduction 200 μ L, the chromatographic peak of collection 14.1 ~ 14.7 min, repeatedly cumulative rear evaporate to dryness; Gained material is used pure dissolve with methanol again, then take pure methyl alcohol as moving phase, separated with Sephadex LH-20 gel filtration chromatography, gets final product to obtain target compound.
Embodiment 5
Turkish tobaccos sample is adopted in Baoshan, Yunnan, and kind is Bath horse.Turkish tobaccos complete stool is sampled to 2.3 kg and be crushed to 30 orders, the methyl alcohol supersound extraction with 99% 5 times, each 50 minutes, extracting solution merged, filters, and concentrating under reduced pressure becomes medicinal extract, obtains medicinal extract 200 g.After 95% dissolve with methanol that medicinal extract use weight ratio is 2.5 times, with the thick silica gel mixed sample of 100 order of 100 g, the 300 order silica gel dress posts of 1.7 kg carry out silica gel column chromatography.Chloroform-methanol is pressed respectively 20:1,9:1, and 8:2,7:3,6:4, the volume proportion of 5:5, carries out gradient elution, collects various piece elutriant concentrated; The 8:2 part of elutriant is further used high pressure lipuid chromatography (HPLC) separation and purification, and the methanol-water of 50:50 of take is moving phase, adopts 20 mm * 250 mm, the C of 5 μ m
18preparative column is stationary phase, and flow velocity is 15 mL/min, and it is 254 nm that UV-detector detects wavelength, each sample introduction 200 μ L, the chromatographic peak of collection 13.9 min, repeatedly cumulative rear evaporate to dryness; Gained material is used pure dissolve with methanol again, then take pure methyl alcohol as moving phase, separated with Sephadex LH-20 gel filtration chromatography, gets final product to obtain target compound.
Embodiment 6
Getting the compound of embodiment 1 preparation, is yellow jelly end.
Measuring method is: with nucleus magnetic resonance, in conjunction with other spectroscopic technique, identify structure.
One, invention compound 1
1) UV spectrum (solvent is methyl alcohol),
λ max(log
ε) 312 (3.88), 260 (4.02), 250 (4.46) nm;
2) infrared spectra (pressing potassium bromide troche)
ν max3365,2958,2876,1720,1708,1625,1510,1455,1420,1258,1172,1040,955,870 cm
-1;
3) high resolution mass spectrum (HRESIMS) provides quasi-molecular ion peak m/z 377.0879 [M-H]
-(calculated value 377.0873).In conjunction with
1h and
13c NMR spectrum provides a molecular formula C
18h
18o
9, degree of unsaturation is 10.
From
1h and
13cNMR spectrum (figure-1 and figure-2, attribution data is in Table-1) signal can be found out compound
1have outside the parent nucleus of a furans cinnamic acid, also have the substituting group of 1 shikimic acid.This compound
1be named as Nicotfuran A.
Two. invention compound 2
1) UV spectrum (solvent is methyl alcohol),
λ max(log
ε) 328 (3.82), 262 (3.97), 210 (4.48) (4.15) nm;
2) infrared spectra (pressing potassium bromide troche)
ν max3362 2955,2872,1722,1705,1623,1510,1458,1422,1263,1174,1054,953,875 cm
-1;
3) high resolution mass spectrum (HRESIMS) provides quasi-molecular ion peak m/z 391.1029 [M-H]
-(calculated value 391.1022).In conjunction with
1h and
13c NMR spectrum provides a molecular formula C
19h
20o
9, degree of unsaturation is 10.
From
1h and
13cNMR spectrum (figure-3 and figure-4, attribution data is in Table-1) signal can find out that compound 2 and compound 1 are similar, compound 2 just how a methoxyl group signal.This compound
2be named as
nicotfuranB.
Embodiment 7
Getting the compound of embodiment 2 preparations, is yellow jelly end.Measuring method is identical with embodiment 6, confirms that the compound of embodiment 2 preparations is described Phenylpropanoid Glycosides compound---Nicotfuran A and Nicotfuran B.
Embodiment 8
Getting the compound of embodiment 3 preparations, is yellow jelly end.Measuring method is identical with embodiment 6, confirms that the compound of embodiment 3 preparations is described Phenylpropanoid Glycosides compound---Nicotfuran A and Nicotfuran B.
Embodiment 9
Getting the compound of embodiment 4 preparations, is yellow jelly end.Measuring method is identical with embodiment 6, confirms that the compound of embodiment 4 preparations is described Phenylpropanoid Glycosides compound---Nicotfuran A and Nicotfuran B.
Embodiment 10
Getting the compound of embodiment 5 preparations, is yellow jelly end.Measuring method is identical with embodiment 6, confirms that the compound of embodiment 5 preparations is described Phenylpropanoid Glycosides compound---Nicotfuran A and Nicotfuran B.
Embodiment 11
The anti-tumor activity of arbitrary Phenylpropanoid Glycosides compound that embodiment 1 ~ 5 is prepared detects:
Anticancer experiment in vitro mtt assay, subject cell strain has NB4, A549, SHSY5Y, PC3, MCF7 totally 5 kinds of tumor cell lines.
Experimental technique:
1. inoculating cell: with the nutrient solution (DMEM or RMPI1640) containing 10% foetal calf serum, be made into individual cells suspension, with every hole 5000-10000 cell, be inoculated into 96 orifice plates, every pore volume 100 μ l, attached cell shifts to an earlier date 12 hours inoculation culture.
2. add testing compound solution (fixed concentration 40 μ M primary dcreening operations are suppressed near compound 50% in this concentration to growth of tumour cell and establish 5 concentration and enter gradient and sieve again), every hole final volume 200 μ l, 3 multiple holes are all established in every kind of processing.
3. colour developing: cultivate after 48 hours for 37 degrees Celsius, every hole adds MTT solution 20 μ l.Continue to hatch 4 hours, stop cultivating, inhale and abandon culture supernatant in hole, every hole adds the SDS solution (10%) of 200 μ l, and night incubation (37 ℃ of temperature), fully melts crystallisate.
4. colorimetric: select 595nm wavelength, enzyme-linked immunosorbent assay instrument (Bio-Rad 680) reads each hole absorbance value, records result, take concentration as X-coordinate, cell survival rate is that ordinate zou is drawn cell growth curve, the IC of application two-point method (Reed and Muench method) computerized compound
50value.
Result shows: the compounds of this invention
1,
2sHSY5Y tumor cell line is demonstrated to obvious inhibition active, corresponding IC
50value is respectively 1.5 and 2.2
μm.
The compounds of this invention has been carried out to safety evaluation, by Micronuclei In The Mouse Bone Marrow test, Ames experiment and TK transgenation test, and prove that the compounds of this invention is nontoxic to animal, use safety.
This compound is added in corresponding tumor cell culture liquid with the concentration of 10 μ M, the inhibiting rate of observation period to tumour cell.Result shows, under 10 μ M concentration, and the compounds of this invention
1,2to SHSY5Y tumor cell line inhibiting rate all higher than 50%.
Claims (3)
1. a preparation method for Phenylpropanoid Glycosides compound, is characterized in that described Phenylpropanoid Glycosides compound is that separation obtains from tobacco, has following structure:
Wherein, R represents hydrogen, methyl; Described tobacco is that adopting in Baoshan, Yunnan, kind is the Turkish tobaccos of Bath horse; Its preparation method comprises extraction, silica gel column chromatography, high pressure liquid chromatography separating step, specifically comprises:
A, extraction: plant sample is crushed to 20 ~ 40 orders, the methyl alcohol supersound extraction with 70 ~ 99% 3 ~ 5 times, the supersound extraction time is 30 ~ 60 min, and extracting solution merges, and filters, and concentrating under reduced pressure becomes medicinal extract;
B, silica gel column chromatography: medicinal extract is before silica gel column chromatography rough segmentation, with 90 ~ 99% dissolve with methanol of 1.5 ~ 3 times of amounts of weight ratio, with weight ratio be the thick silica gel mix and blend of 80 ~ 100 order of 0.25 ~ 0.5 times, further remove impurity; Then medicinal extract carries out silica gel column chromatography with 200 ~ 300 order silica gel dress posts of 5 ~ 10 times of amounts of weight ratio, the chloroform-methanol solution that the volume proportion of take is 20:1,9:1,8:2,7:3,6:4,5:5 carries out gradient elution, merge identical part, collect each several part elutriant concentrated;
C, high pressure liquid chromatography separation: the 8:2 part of B step further obtains described Phenylpropanoid Glycosides compound with high pressure liquid chromatography separation and purification; Described high pressure liquid chromatography separation and purification is to adopt 20mm * 250mm, the C of 5 μ m
18chromatographic column, flow velocity is 10 ~ 15mL/min, the methanol-water that the volume proportion of take is 40:60 ~ 50:50 is moving phase; Material after high pressure lipuid chromatography (HPLC) separation and purification is used pure dissolve with methanol again, take pure methyl alcohol as moving phase, separated with Sephadex LH-20 gel filtration chromatography, with further separation and purification.
2. the preparation method of Phenylpropanoid Glycosides compound according to claim 1, is characterized in that in described A step, methanol concentration is 85 ~ 95
%.
3. the preparation method of Phenylpropanoid Glycosides compound according to claim 1, the mobile phase methanol-water that it is characterized in that described C step is the solution of volume proportion 50:50.
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| CN104945360B (en) * | 2015-06-25 | 2017-05-10 | 云南中烟工业有限责任公司 | Preparation method and application of phenylpropanoid compound in tobacco |
| CN105001186B (en) * | 2015-06-25 | 2017-07-18 | 云南中烟工业有限责任公司 | A kind of preparation method and application of isopentene group benzo lactone compound in tobacco |
| CN105777677B (en) * | 2016-03-25 | 2017-09-29 | 云南省烟草农业科学研究院 | A kind of furancarboxylic acid class compound and its preparation method and application |
| CN111072608B (en) * | 2019-12-23 | 2023-04-07 | 河南理工大学 | Preparation method of phenylpropanoid compound |
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