CN106220595B - A kind of benzofuran compounds, preparation method and use - Google Patents
A kind of benzofuran compounds, preparation method and use Download PDFInfo
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- CN106220595B CN106220595B CN201610628723.5A CN201610628723A CN106220595B CN 106220595 B CN106220595 B CN 106220595B CN 201610628723 A CN201610628723 A CN 201610628723A CN 106220595 B CN106220595 B CN 106220595B
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D307/00—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom
- C07D307/77—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom ortho- or peri-condensed with carbocyclic rings or ring systems
- C07D307/78—Benzo [b] furans; Hydrogenated benzo [b] furans
- C07D307/79—Benzo [b] furans; Hydrogenated benzo [b] furans with only hydrogen atoms, hydrocarbon or substituted hydrocarbon radicals, directly attached to carbon atoms of the hetero ring
- C07D307/80—Radicals substituted by oxygen atoms
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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
- A01N43/06—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 five-membered rings
- A01N43/12—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 five-membered rings condensed with a carbocyclic ring
Abstract
The invention discloses a kind of benzofuran compounds；With following structure：The compound is named as：4 (base of 53 methyl benzofuran of (2 ethoxy) 6 methoxyl group 2) phenol；The invention also discloses its preparation method of the benzofuran compounds and the application in resisting tobacco mosaic virus medicine is prepared.
Description
Technical field
The invention belongs to technical field of tobacco chemistry, and in particular to a kind of benzofuran for extracting to obtain first from tobacco
Class compound.Meanwhile the application the invention further relates to the preparation method of the compound and in resisting tobacco mosaic virus.
Background technology
Tobacco is the plant that chemical composition is the most complicated in the world, and secondary metabolite is very abundant, according to nineteen eighty-two Dube
To be reported with Green etc., the chemical composition identified in tobacco is just more than 2549 kinds, by 2008, Rodgman and perfetti
Report, the compound that is found in tobacco, tobacco and cigarette smoke sum is about 8700 kinds.At present, people
The monomer chemistries material come the just kind more than 3000 is identified from tobacco, and also many compositions are not yet identified and.Cigarette
Grass can also therefrom extract a variety of chemical compositions for having value in addition to cigarette smoking purposes is mainly used in, and therefrom find have out
Send out the guiding compound of value.
Furfuran compound exists in many natural plants, and has multiple biological activities.According to the literature, such
Compound have it is antitumor, it is anti-oxidant, Ca2+ influx retardance, angiotensin-ii receptor antagonism, adenosine A l receptor antagonists, resist true
The pharmacological actions such as bacterium, antibacterial activity and platelet aggregation antagonism.Because Benzofurans compound has the pharmacology of such wide spectrum
Activity, domestic and international researcher conduct in-depth research to such compound, in addition to such compound is found from natural products,
The compound with more excellent pharmacological activity is also obtained by structural modification., can in order to study the structure-activity relationship of this kind of compound
More furfuran compounds are further researched and developed, therefrom find effective lead compound and active group.The present invention
Related report is not yet seen in isolated a kind of new benzofuran compounds, the compound from Yunnan Flue-cured Tobacco tobacco leaf
Road, it is worth mentioning at this point that the compound has significant resisting tobacco mosaic disease virus activity.
The content of the invention
It is an object of the invention to provide a kind of new benzofuran compounds；It is a further object to provide
A kind of method for preparing the benzofuran compounds；The present invention also aims to provide the benzofuran compound to exist
Application in resisting tobacco mosaic virus.
Unless otherwise indicated, the percentage employed in the present invention is mass percent.
First aspect present invention isolates a kind of new benzofuran compounds from tobacco, and its molecular formula is
C18H10O4, there is following structural formula：
The compound is named as：4- (5- (2- ethoxys) -6- methoxyl group -3- methyl benzofuran -2- bases) phenol, it is
Light yellow gum thing.
The method for preparing the benzofuran compounds, this method comprise the following steps：
(1) medicinal extract extracts：Tobacco sample is crushed, with high concentration methanol (wt%：80%~100%) or high concentration ethanol
(wt%：80%~100%) or high concentration acetone (wt%：60%~90%) it is Extraction solvent, Extraction solvent：Tobacco (weight
Than)=2~4:1,24h~72h is soaked, is extracted 3~5 times, merges extract solution, filtering and concentrating into medicinal extract；
(2) silica gel column chromatography：Medicinal extract is used after being dissolved with weight than the pure methanol or straight alcohol or pure acetone of 1.5~3 times of amounts
80~100 mesh silica gel mixed samples of the weight than 0.8~1.2 times, with 160~300 mesh silica gel dry column-packings of the weight than 2~4 times of amounts
Carry out silica gel column chromatography；Using volume proportion as (1:0、20:1、9:1、8:2、7:3、6:4、1:1 and 1:2) chloroform-acetone solution
Gradient elution is carried out, merges identical part, each several part eluent is collected and concentrates；
(3) high pressure liquid chromatography isolates and purifies：The 7 of column chromatography eluent:3 parts are further separated with high pressure liquid chromatography
Purify and produce described benzofuran compounds.
It is to use 21.2mm × 250mm, 5 μm of C that high pressure liquid chromatography, which isolates and purifies,18Chromatographic column, flow velocity 20mL/min,
Mobile phase is 54wt% methanol, and UV-detector Detection wavelength is 312nm, each μ L of sample introduction 200, collects 26.2min color
Spectral peak, it is evaporated after repeatedly adding up.
Through the high performance liquid chromatography separation after purification, a preferable subsequent process scheme is that gained compound is again
Dissolved with pure methanol, then using pure methanol as mobile phase, separated with gel filtration chromatography, further to isolate and purify.
The compound of table 1.1H NMR and13C NMR datas (C5D5N)
The structure for the benzofuran compounds that method described above is prepared is measured by the following method.The present invention
Compound is light yellow gum thing；High resolution mass spectrum (HRESIMS) provides quasi-molecular ion peak m/z 321.1109 [M+Na]+
(calculated value 321.1103).With reference to1H and13C H NMR spectroscopies provide a molecular formula C18H18O4, degree of unsaturation 11.Its infrared spectrum
Show hydroxyl (3436cm-1) and aromatic ring (1612,1518,1457cm-1) structure, ultraviolet spectra has most in 210,272,312nm
Big absorb confirms aromatic ring structure be present in compound.Compound1H and13C NMR and DEPT data (table -1) are shown in compound
In the presence of 17 carbon and 16 hydrogen, comprising 11,2,4,5- quaternary phenyl ring (C-1~C-6, H-3 and H-6), 1 Isosorbide-5-Nitrae-four takes
Phenyl ring (C-1'~C-6', the H in generation2- 3', 5'), 1 ethoxy (C-7 and C-8, H2- 7 and H-8), 1 methyl (C-9', H3-
9'), one group of double bond (C-7 and C-8), 1 methoxyl group (δC56.2q δH3.84s), 1 phenolic hydroxyl group (δH10.77s).According to
Nuclear magnetic resonance data (two phenyl ring, C-7 '~C-9 ', and H in compound3- 9 ') and known compound methoxyl group -4 '-hydroxyl -
Aryl -3- methyl -6- hydroxyl benzofurans are similar, can initial guess compound (1) may be 3- methyl -2- aryl benzo furans
Mutter.In addition, pass through H3- 9 ' and C-1, C-7 ' and C-8 ', H2- 2 ', 6 ' and C-7 ', H-6 and C-1, C-2, C-8 '；And H-3 and C-
1st, it is 3- methyl -2- arylbenzofurans that C-2 HMBC related (figure -2), which can further confirm compound (1),.The bone of compound
After frame is confirmed, remaining substituted radical, ethoxy, which is substituted in C-5 positions, can pass through H2- 7 and C-4, C-5 and C-6, H-8 and C-
5, and H-6 determinations related to C-7 HMBC；Methoxy substitution can lead to methoxyl group hydrogen (δ in C-4HAnd C-4 (δ C 3.84)
152.8) HMBC is related to be confirmed；Phenolic hydroxyl group be substituted in C-4 ' positions can by phenolic hydroxyl group hydrogen (δ H 10.77) and with C-4 ' (δ C
157.4), C-3 ', the HMBC of 5 ' (116.3) is related to be determined.So far, the structure of this compound is determined, and is named as 4- (5-
(2- ethoxys) -6- methoxyl group -3- methyl benzofuran -2- bases) phenol.
Infrared, the ultraviolet and mass spectrometric data of compound：UV(MeOH)λmax(logε)：210(4.08)、272(3.35)、312
(3.64)nm；IR(KBr)νmax3436、2965、1612、1518、1457、1379、1145、1082、870、812；1H and13C
NMR data(C5D5N, 500 and 125MHz), it is shown in Table 1. positive ion mode ESIMS m/z 321 [M+Na]+；Positive ion mode
HRESIMS m/z 321.1109[M+Na]+(calculated value 321.1103, C18H18NaO4)。
The activity of resisting tobacco mosaic virus that the compounds of this invention has been carried out using half leaf method is tested, as a result bright compound
Relative inhibition is 43.5%, more than the relative inhibition 31.5% of control Ningnanmycin, illustrates that compound has good anti-cigarette
Showy flowers of herbaceous plants leaf disease cytotoxic activity.
Beneficial effects of the present invention：
The compounds of this invention is separated first, is defined as benzene by above-mentioned nuclear magnetic resonance and measuring method of mass spectrum
Benzofuran compound, and characterize its concrete structure.The compound that Activity determination result discloses the present invention is preparing anti-wheel
There is good application prospect in shape virus drugs.The compounds of this invention activity simple in construction preferably, can be used as mosaic disease resisting poison
The guiding compound of thing research and development is researched and developed for mosaic disease resisting cytotoxic drug preparation.
Brief description of the drawings
Fig. 1 is the carbon-13 nmr spectra of benzofuran compounds of the present invention；
Fig. 2 is the proton nmr spectra of benzofuran compounds of the present invention；
Fig. 3 is that the main HMBC of benzofuran compounds of the present invention is related.
Embodiment
The present invention is described in further detail with reference to the accompanying drawings and examples, but not in any way to the present invention
It is any limitation as, based on present invention teach that any conversion or improvement made, each fall within protection scope of the present invention.
Embodiment 1
Prepare benzofuran compounds C18H18O4, including medicinal extract extraction, silica gel column chromatography, high pressure liquid chromatography separation,
Specifically use following steps：
1. medicinal extract extracts：Tobacco leaf is taken to crush, with high concentration methanol (wt%：Or high concentration ethanol (wt% 95%)：95%)
Or high concentration acetone (wt%：70%) it is Extraction solvent, Extraction solvent：Tobacco (weight ratio)=3:5,54h is soaked, is extracted 4 times,
Merge extract solution, filtering and concentrating into medicinal extract.
2. silica gel column chromatography：Medicinal extract uses weight after being dissolved with weight than the pure methanol or straight alcohol or pure acetone of 2.5 times of amounts
80~100 mesh silica gel mixed samples than 1.2 times, silica gel column chromatography is carried out with 250 mesh silica gel dry column-packings of the weight than 3 times of amounts；With
Volume proportion is (1:0、20:1、9:1、8:2、7:3、6:4、1:1 and 1:2) chloroform-acetone solution carries out gradient elution, merges
Identical part, collect each several part eluent and concentrate.
3. high pressure liquid chromatography separates：The 7 of column chromatography eluent:3 parts are further isolated and purified with high pressure liquid chromatography
Described benzofuran compounds are produced, it is to use 21.2mm × 250mm, 5 μm of C that high pressure liquid chromatography, which isolates and purifies,18Color
Post, flow velocity 20mL/min are composed, mobile phase is 54wt% methanol, and UV-detector Detection wavelength is 312nm, each sample introduction
200 μ L, 26.2min chromatographic peak is collected, be evaporated after repeatedly adding up.
High pressure lipuid chromatography (HPLC) isolate and purify after material, a preferable post processing scheme is that gained compound is again
Dissolved with pure methanol, then using pure methanol as mobile phase, separated with gel filtration chromatography, further to isolate and purify.
Raw tobacco material used in the present invention is not limited by area and kind, the present invention can be realized, below with from cloud
The raw tobacco material of cigarette industry Co., Ltd different sources in south, the present invention will be further described.
Embodiment 2
Tobacco sample derives from Yunnan Yuxi, and kind is Yuxi K326.Tobacco sampling 2.0kg is crushed with 95% methanol
Extraction 5 times, 24h is extracted every time, extract solution merges, and filtering, is concentrated under reduced pressure into medicinal extract, obtains medicinal extract 105g.Medicinal extract is with weight than 2.0
The 120g thick silica gel mixed sample of 100 mesh is used after the pure methanol dissolving of amount again, 0.6kg 160 mesh silica gel fill post progress silica gel column chromatography,
It is 1 with volume proportion:0、20:1、9:1、8:2、7:3、6:4、1:1、1:2 chloroform-acetone gradient elution, TLC monitorings merge phase
Same part, 8 parts are obtained, wherein volume proportion is 7:3 chloroform-acetone elution fraction pacifies prompt logical sequence 1,100 half and prepares height
Effect liquid phase chromatogram separates, and using 54wt% methanol as mobile phase, Zorbax SB-C18 (21.2 × 250mm, 5 μm) prepare post and are
Stationary phase, flow velocity 20ml/min, UV-detector Detection wavelength are 312nm, each μ L of sample introduction 200, collect 26.2min color
Spectral peak, it is evaporated after repeatedly adding up；Products therefrom is dissolved with pure methanol again, then using pure methanol as mobile phase, uses Sephadex
LH-20 gel filtration chromatographies separate, and produce the noval chemical compound.
Embodiment 3
Tobacco sample derives from Dali, and kind is cloud and mist 200, tobacco sampling 3.5kg is shredded, with 95% ethanol
Extraction 4 times, 48h is extracted every time, extract solution merges, and filtering, is concentrated under reduced pressure into medicinal extract, obtains medicinal extract 250g.Medicinal extract is with weight than 2.0
The 250g thick silica gel mixed sample of 80 mesh is used after the pure methanol dissolving of amount again, 1.2kg 200 mesh silica gel fill post progress silica gel column chromatography,
It is 1 with volume proportion:0、20:1、9:1、8:2、7:3、6:4、1:1、1:2 chloroform-acetone gradient elution, TLC monitorings merge phase
Same part, 8 parts are obtained, wherein volume proportion is 7:3 chloroform-acetone elution fraction pacifies prompt logical sequence 1,100 half and prepares height
Effect liquid phase chromatogram separates, and using 54% methanol as mobile phase, it is solid that Zorbax SB-C18 (21.2 × 250mm, 5 μm), which prepare post,
Determine phase, flow velocity 20ml/min, UV-detector Detection wavelength is 312nm, each μ L of sample introduction 200, collects 26.2min chromatogram
Peak, it is evaporated after repeatedly adding up；Products therefrom is dissolved with pure methanol again, then using pure methanol as mobile phase, with Sephadex LH-
20 gel filtration chromatographies separate, and produce the noval chemical compound.
Embodiment 4
Tobacco sample derives from Kunming, Yunnan, and kind is the big gold dollar of safflower, tobacco sampling 5kg is crushed, with 75wt%'s
Acetone ultrasonic extraction 3 times, 72h is extracted every time, extract solution merges, and filtering, is concentrated under reduced pressure into medicinal extract, obtains medicinal extract 380g.Medicinal extract
With the thick silica gel mixed sample of 90 mesh that 400g is used after pure methanol dissolving of the weight than 1.6 times of amounts, 2.4kg 180 mesh silica gel dress post is carried out
Silica gel column chromatography, it is 1 with volume proportion:0、20:1、9:1、8:2、7:3、6:4、1:1、1:2 chloroform-acetone gradient elution,
TLC monitorings merge identical part, obtain 8 parts, and wherein volume proportion is 7:3 chloroform-acetone elution fraction is prompt with peace
The preparative high-performance liquid chromatographic of logical sequence 1,100 half separates, using 54wt% methanol as mobile phase, Zorbax SB-C18 (21.2 ×
250mm, 5 μm) to prepare post be stationary phase, flow velocity 20ml/min, UV-detector Detection wavelength is 312nm, each sample introduction 200
μ L, 26.2min chromatographic peak is collected, be evaporated after repeatedly adding up；Products therefrom is dissolved with pure methanol again, then using pure methanol as stream
Dynamic phase, is separated with Sephadex LH-20 gel filtration chromatographies, produces the noval chemical compound.
Embodiment 5
The identification of --- --- compound structure
Compound prepared by Example 1-4, the structure for the benzofuran compounds that method described above is prepared are led to
Following methods are crossed to be measured.The compounds of this invention is light yellow gum thing；High resolution mass spectrum (HRESIMS) provide quasi-molecule from
Sub- peak m/z321.1109 [M+Na]+(calculated value 321.1103).With reference to1H and13C H NMR spectroscopies provide a molecular formula C18H18O4,
Degree of unsaturation is 11.Its infrared spectrum shows hydroxyl (3436cm-1) and aromatic ring (1612,1518,1457cm-1) structure, it is ultraviolet
Spectrum has absorption maximum to confirm aromatic ring structure be present in compound in 210,272,312nm.Compound1H and13C NMR and
DEPT data (table -1) show in compound 17 carbon and 16 hydrogen be present, comprising 11,2,4,5- quaternary phenyl ring (C-1
~C-6, H-3 and H-6), 1 Isosorbide-5-Nitrae-quaternary phenyl ring (C-1'~C-6', H2- 3', 5'), 1 ethoxy (C-7 and C-8,
H2- 7 and H-8), 1 methyl (C-9', H3- 9'), one group of double bond (C-7 and C-8), 1 methoxyl group (δC56.2q δH
3.84s), 1 phenolic hydroxyl group (δH10.77s).According to nuclear magnetic resonance data in compound (two phenyl ring, C-7 '~C-9 ', and H3-
9 ') it is similar with known compound methoxyl group -4 '-bis (hydroxy-aromatic) base -3- methyl -6- hydroxyl benzofurans, can initial guess compound
(1) it may be 3- methyl -2- arylbenzofurans.In addition, pass through H3- 9 ' and C-1, C-7 ' and C-8 ', H2- 2 ', 6 ' and C-7 ',
H-6 and C-1, C-2, C-8 '；And it is 3- first that H-3 (figure -2) related to C-1, C-2 HMBC, which can further confirm compound (1),
Base -2- arylbenzofurans.After the skeleton of compound is confirmed, remaining substituted radical, ethoxy, which is substituted in C-5 positions, to be led to
Cross H2- 7 and C-4, C-5 and C-6, H-8 and C-5, and H-6 is related to C-7 HMBC determines；Methoxy substitution can lead in C-4
Methoxyl group hydrogen (δH3.84) it is related to C-4 (δ C 152.8) HMBC to confirm；Phenolic hydroxyl group is substituted in C-4 ' positions can be by phenolic hydroxyl group hydrogen
(δ H 10.77) and determined with C-4 ' (δ C 157.4), C-3 ', the HMBC correlations of 5 ' (116.3).So far, the structure of this compound
Determined, and be named as 4- (5- (2- ethoxys) -6- methoxyl group -3- methyl benzofuran -2- bases) phenol.
Embodiment 6
Compound prepared by Example 3, is yellow jelly.Assay method is same as Example 5, confirms embodiment 3
The compound of preparation is described benzofuran compounds --- 4- (5- (2- ethoxys) -6- methoxyl group -3- methyl benzo furans
Mutter -2- bases) phenol.
Embodiment 7
Compound prepared by Example 4, is yellow jelly.Assay method is same as Example 5, confirms embodiment 4
The compound of preparation is described 4- (5- (2- ethoxys) -6- methoxyl group -3- methyl benzofuran -2- bases) phenol.
Embodiment 8
Prepared by Example 1-4 appoints benzofuran compounds to carry out activity of resisting tobacco mosaic virus experiment, tests feelings
Condition is as follows：
Using half leaf method, resisting tobacco mosaic disease is carried out to the compounds of this invention when the mass concentration of medicament is 50mg/L
Cytotoxic activity determines.On the plant of 5~6 age flue-cured tobaccos, the blade (leaf row is normal, disease-free no worm) suitable for test is chosen, first will
Blade uniformly sprinkles fine emery powder, with writing brush by standby tobacco mosaic virus (TMV) source (3.0 × 10-3) be uniformly put on sprinkled with diamond dust
Blade on, connect after the blade of all middle choosings after poison terminates, be immediately placed in the culture dish for fill decoction and handle 20min, take out,
The globule and decoction on blade are wiped, the recovery of two and half leaves is emitted on and is covered with the glass jar of toilet paper moisturizing, and covers glass
Lid, temperature control (23 ± 2) DEG C are placed on greenhouse natural light irradiation, 2~3d be visible withered spot each processing set second half leaf as pair
According to, be additionally provided with 1 group be commodity Ningnanmycin processing as a comparison, press formula calculate relative inhibition.
XI%=(CK-T)/CK × 100%
X：Relative inhibition (%), CK：The withered spot number (individual) that half in clear water connects malicious leaf is soaked in, T is soaked in decoction
Half connects the withered spot number (individual) of malicious leaf.
As a result the relative inhibition of bright compound is 43.5%, more than the relative inhibition of control Ningnanmycin
31.5%, illustrate that compound has good activity of resisting tobacco mosaic virus.
Claims (4)
- A kind of 1. preparation method of benzofuran compounds, wherein the benzofuran compounds have following structures：Characterized in that, this method comprises the following steps：(1) medicinal extract extracts:Using tobacco leaf as raw material, tobacco leaf is crushed or is cut into segment, with concentration expressed in percentage by weight 80%~100% Methanol or ethanol, or the acetone of concentration expressed in percentage by weight 60%~90% is Extraction solvent, Extraction solvent：Weight ratio=2 of tobacco leaf ~4:1,24h~72h is soaked, is extracted 3~5 times, merges extract solution, filtering and concentrating into medicinal extract；(2) silica gel column chromatography：The medicinal extract that step (1) obtains is filled with 160~300 mesh silica gel dry method of its weight than 2~4 times of amounts Post carries out silica gel column chromatography；Using volume proportion as 1:0、20:1、9:1、8:2、7:3、6:4、1:1 and 1:2 chloroform-acetone solution Gradient elution is carried out, merges identical part, each several part eluent is collected and concentrates；(3) high pressure liquid chromatography isolates and purifies：The 7 of eluent after step (2) is concentrated:Further use high pressure liquid phase color in 3 parts Spectrum, which isolates and purifies, produces required benzofuran compounds.
- 2. preparation method according to claim 1, it is characterised in that in step (3), after high pressure liquid chromatography isolates and purifies Compound dissolved again with pure methanol, then using pure methanol as mobile phase, separated with gel filtration chromatography, it is pure further to separate Change.
- 3. preparation method according to claim 1, it is characterised in that in step (3), the separation of described high pressure liquid chromatography Purifying is to use 21.2mm × 250mm, 5 μm of C18Chromatographic column, flow velocity 20mL/min, mobile phase is 54wt% methanol, purple External detector Detection wavelength is 312nm, each μ L of sample introduction 200, collects 26.2min chromatographic peak, is evaporated after repeatedly adding up.
- 4. preparation method according to claim 1, it is characterised in that：In step (2), described medicinal extract is through silica gel column layer Before analysing rough segmentation, after pure methanol or straight alcohol or pure acetone dissolving of the weight than 1.5~3 times of amounts, with weight than 0.8~1.2 times 80~100 mesh silica gel mixed samples.
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Non-Patent Citations (2)
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| Antiviral Phenolic Compounds from Arundina gramnifolia;Qiu-Fen Hu 等;《J. Nat. Prod.》;20130131;第76卷;第292?296页 * |
| Two new 2-arylbenzofurans from the stems of Nicotiana tabacum and their bioactivities;Pei-Song Yang 等;《Heterocycles》;20160620;第92卷(第8期);第1462-1467页 * |
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