CN106565724B - Favus of the scalp flower extract and its extracting method and application - Google Patents
Favus of the scalp flower extract and its extracting method and application Download PDFInfo
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D491/00—Heterocyclic compounds containing in the condensed ring system both one or more rings having oxygen atoms as the only ring hetero atoms and one or more rings having nitrogen atoms as the only ring hetero atoms, not provided for by groups C07D451/00 - C07D459/00, C07D463/00, C07D477/00 or C07D489/00
- C07D491/02—Heterocyclic compounds containing in the condensed ring system both one or more rings having oxygen atoms as the only ring hetero atoms and one or more rings having nitrogen atoms as the only ring hetero atoms, not provided for by groups C07D451/00 - C07D459/00, C07D463/00, C07D477/00 or C07D489/00 in which the condensed system contains two hetero rings
- C07D491/04—Ortho-condensed systems
- C07D491/056—Ortho-condensed systems with two or more oxygen atoms as ring hetero atoms in the oxygen-containing ring
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- A—HUMAN NECESSITIES
- A01—AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
- A01N—PRESERVATION OF BODIES OF HUMANS OR ANIMALS OR PLANTS OR PARTS THEREOF; BIOCIDES, e.g. AS DISINFECTANTS, AS PESTICIDES OR AS HERBICIDES; PEST REPELLANTS OR ATTRACTANTS; PLANT GROWTH REGULATORS
- A01N43/00—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds
- A01N43/34—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with one nitrogen atom as the only ring hetero atom
- A01N43/40—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with one nitrogen atom as the only ring hetero atom six-membered rings
- A01N43/42—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with one nitrogen atom as the only ring hetero atom six-membered rings condensed with carbocyclic rings
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- 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
- A01N43/90—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having two or more relevant hetero rings, condensed among themselves or with a common carbocyclic ring system
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- C07D221/02—Heterocyclic compounds containing six-membered rings having one nitrogen atom as the only ring hetero atom, not provided for by groups C07D211/00 - C07D219/00 condensed with carbocyclic rings or ring systems
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- C07D455/03—Heterocyclic compounds containing quinolizine ring systems, e.g. emetine alkaloids, protoberberine; Alkylenedioxy derivatives of dibenzo [a, g] quinolizines, e.g. berberine containing quinolizine ring systems directly condensed with at least one six-membered carbocyclic ring, e.g. protoberberine; Alkylenedioxy derivatives of dibenzo [a, g] quinolizines, e.g. berberine
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D491/00—Heterocyclic compounds containing in the condensed ring system both one or more rings having oxygen atoms as the only ring hetero atoms and one or more rings having nitrogen atoms as the only ring hetero atoms, not provided for by groups C07D451/00 - C07D459/00, C07D463/00, C07D477/00 or C07D489/00
- C07D491/12—Heterocyclic compounds containing in the condensed ring system both one or more rings having oxygen atoms as the only ring hetero atoms and one or more rings having nitrogen atoms as the only ring hetero atoms, not provided for by groups C07D451/00 - C07D459/00, C07D463/00, C07D477/00 or C07D489/00 in which the condensed system contains three hetero rings
- C07D491/14—Ortho-condensed systems
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Abstract
The present invention relates to a kind of favus of the scalp flower extract and its extracting method and applications.The present invention is based on the research to slenderstalk dicranostigma herb antibacterial activity and its active constituent, it is found that favus of the scalp flower extract has significant inhibitory activity to various plants cause of disease, there are the potentiality for being used to prepare plant antimicrobial as effective component.Meanwhile the invention also found containing multiple effective components based on magnoflorine in favus of the scalp flower extract, and provide the method and technique of effective component in a kind of fast enriching slenderstalk dicranostigma herb.
Description
Technical field
The present invention relates to the drugs of the anti-phytopathogen of plant source, and in particular to a kind of favus of the scalp flower extract and its extraction side
Method and application.
Background technique
Phytopathogen has shadow very serious to the yield and quality of the healthy growth of plant and development, crops
It rings.Therefore, applying for bactericide has great importance in modern agriculture.But the long-term weight of same fungicide
Multiple use already leads to phytopathogen and produces very strong drug resistance to many existing bactericides.In addition, many countries
Being forbidden to use some pairs of environment, people or ecology has dysgenic disinfectant use in agriculture.Therefore, research and development is efficiently low
Malicious and environmental protection Huang Dezhi has great importance.
Biological pesticide is that current novel pesticide studies most popular field, and botanical pesticide is one of biological pesticide important
Aspect.Slenderstalk dicranostigma herb (Dicranostigma leptopodum (maxim.) fedde) also known as baldhead spend, rein in the horse back in (Shaanxi), rabbit
Son is spent, and one of Papaveraceae (Papaveraceae) convex combination algorithm plant is belonged to.The plant is distributed widely in northwestern Yunnan Province, four
River western part, southern Tibet, East of Qinghai Province, SOUTH OF GANSU to the southeast, Qinling Mountains in Shaanxi north slope, Southern Shanxi Province, the Hebei west and south and
The Henan northwestward, is born in height above sea level 400-2900(-3700) the careless slope or roadside of rice, ridge, the top of a wall, roof are also common.Its root or
Herb can be made medicinal, have clearing heat and detoxicating, Repercusion analgesia, desinsection and other effects, control acute toothache, sore-throat, tonsillitis, lymph node
Core, the favus of the scalp, boil scabies, ulcer.The plant is rich in a variety of alkaloids, has been demonstrated with sedation-analgesia, antitumor, antibacterial etc.
Multiple biological activities.But up to the present, there is not yet any grind about the anti-phytopathogen of favus of the scalp flower extract is active
Study carefully report.
Although slenderstalk dicranostigma herb has natural resources abundant in China, fail to be utilized effectively for a long time.This may lead
It is related the plant is not eaten with humans and animals.Therefore, the present invention both provides one effectively for the development and utilization of slenderstalk dicranostigma herb
Approach, also provide a kind of agricultural antibacterial agent in novel plant source for China, at the same also for vast farmers provide one it is new
It gets rich approach.
Summary of the invention
The object of the present invention is to provide a kind of favus of the scalp flower extract and its extracting method and applications, and such drug is to a variety of plants
Object pathogen has good inhibitory activity.
The technical scheme adopted by the invention is as follows:
Favus of the scalp flower extract, it is characterised in that:
The extract is that Papaveraceae (Papaveraceae) convex combination algorithm (Dicranostigma) herbaceos perennial is bald
The herb of sore flower (Dicranostigma leptopodum (maxim.) fedde) or the alcohol extract or water extract of aerial part.
It include antimicrobial component, including magnoflorine, Chelerythrine, sanguinarine, corydalis in the favus of the scalp flower extract
Determine alkali, isocorydine, coptisine and Biflorine.
The application of favus of the scalp flower extract as mentioned, it is characterised in that:
The extract is as the application for preparing plants antimicrobial drug.
The extract has significant inhibitory activity to following phytopathogen:
Apple decay pathogen；Gibberella saubinetii pathogen；Early blight of tomato opportunistic pathogen；Curvularia pathogen；Pumpkin is withered
Pathogen；Cotton is withered, withered germ of water-melon；Dry rot of potato opportunistic pathogen；Alternaria brassicae；Tobacco brown spot pathogen；Apple
Anthrax bacteria；Rice blast fungus；Botryosphaeria berengeriana f. sp；Tomato Cercospora Sojina Hara.
The extracting method of favus of the scalp flower extract as mentioned, it is characterised in that:
The following steps are included:
Step 1: using ethyl alcohol, methanol or water as solvent, heating extraction is carried out to slenderstalk dicranostigma herb vegetable material, merging repeatedly mentions
The extracting solution taken is stored at room temperature overnight, and decompression filters out sediment, and solvent is evaporated off in gained filtrate decompression, obtains extract；
Step 2: it is dissolved in methanol aqueous solution by extract obtained, stone is successively used with petroleum ether, chloroform and n-butanol or successively
Oily ether, n-butanol are extracted；The resulting chloroform extract of preceding method and n-butyl alcohol extract or the resulting extracting n-butyl alcohol of rear method
Object is favus of the scalp flower extract.
In step 1:
The solid-liquid mixing ratio of slenderstalk dicranostigma herb vegetable material and solvent is 1 g:15 mL, and solution temperature is 50-80 DEG C, when dissolution
Stirring or ultrasonic wave auxiliary；
Temperature when extracting solution evaporating solvent under reduced pressure is 30~40 DEG C.
In step 2:
The extract of slenderstalk dicranostigma herb vegetable material is dissolved in and vegetable material is identical in quality, volume fraction is 10%~25% first
In alcohol solution, petroleum ether, chloroform and n-butanol or petroleum ether, extracting n-butyl alcohol are then successively used, every kind of solvent extraction is three times；
When petroleum ether extraction, each solvent usage is identical as the volume for being extracted liquid；
When chloroform extracts, each solvent usage is to be extracted the half of liquid product；
When extracting n-butyl alcohol, solvent usage, which is followed successively by, three times is extracted 50%, 40% and the 30% of liquid product.
The invention has the following advantages that
Plants antimicrobial drug according to the present invention using favus of the scalp flower extract as effective component is a kind of plant source agriculture
Medicine belongs to one kind of bio-pharmaceutical, meets requirement of the modern society to novel pesticide.Secondly, the drug has antibacterial activity strong, anti-
Bacterium spectrum is wide, environmental-friendly, the features such as being not easy to produce resistance, is lower to humans and animals toxicity.Third, plant involved in the drug
Slenderstalk dicranostigma herb has resourceful, the low feature of development cost.Fourth, slenderstalk dicranostigma herb extraction and separation technology involved in the invention has
The advantages of simple production process, low production cost, environmental pollution are small and are suitable for large-scale production.
Detailed description of the invention
Fig. 1 is the high-efficient liquid phase chromatogram of slenderstalk dicranostigma herb alcohol extracts.
Specific embodiment
The present invention will be described in detail With reference to embodiment.
Drug and application the present invention relates to a kind of favus of the scalp flower extract and its containing the extract or effective component, simultaneously
It is related to the extraction separation method of slenderstalk dicranostigma herb effective component.The present invention is based on to favus of the scalp flower extract antibacterial activity and active constituent
Research, discovery favus of the scalp flower extract have significant inhibitory activity to various plants pathogen, have and are used for as effective component
Prepare the potentiality of plant antimicrobial.Meanwhile the invention also found in favus of the scalp flower extract containing multiple based on magnoflorine
Effective component, and provide the method and technique of effective component in a kind of fast separating concentration slenderstalk dicranostigma herb.
Above-mentioned favus of the scalp flower extract has the feature that
The extract is Papaveraceae convex combination algorithm herbaceos perennial slenderstalk dicranostigma herb (Dicranostigma
Leptopodum (maxim.) fedde) herb alcohol extract or water extract.
Application of the above favus of the scalp flower extract as plant antimicrobial, it is characterised in that: favus of the scalp flower extract contains with wood
Based on magnoflorine, with Chelerythrine, sanguinarine, (6aS)-2,10,11-Trimethoxy-6-methyl-5,6,6a,7-tetrahydro-4H-dibenzo[de,g, isocorydine, coptisine and Biflorine etc. are time more
Kind effective component.
The extraction and separation technology of the above slenderstalk dicranostigma herb antibiotic effective ingredient, it is characterised in that:
The extractive technique is related to extracting slenderstalk dicranostigma herb vegetable material with alcohols solvent such as ethyl alcohol, methanol etc., using more
Kind solvent extracts the effective component in crude extract, and chromatographic technique is utilized to carry out the separation of monomer effective component.
Antibacterial activity in vitro is carried out to favus of the scalp flower extract, extract and monomeric compound using mycelial growth rate method to comment
Valence.By being compared with positive drug, it was demonstrated that favus of the scalp flower extract and its active constituent according to the present invention are to a variety of plants
There are significant inhibitory activity for object pathogen, have the great potential that plant antimicrobial drug is used to prepare as effective component.
Favus of the scalp flower extract and its active constituent have following phytopathogen significant as the application for preparing plants antimicrobial drug
Inhibitory activity:
Apple decay pathogen；Gibberella saubinetii pathogen；Early blight of tomato opportunistic pathogen；Curvularia pathogen；Pumpkin is withered
Pathogen；Cotton is withered, withered germ of water-melon；Dry rot of potato opportunistic pathogen；Alternaria brassicae；Tobacco brown spot pathogen；Apple
Anthrax bacteria；Rice blast fungus；Botryosphaeria berengeriana f. sp, tomato Cercospora Sojina Hara, etc..
Below in conjunction with subordinate list, extracting separation, Structural Identification and determination of activity, invention is further described in detail:
One, the preparation of favus of the scalp flower extract and its enrichment of active constituent:
Using 95% industrial alcohol, methanol or water as solvent, according to 1:15(g/mL) solid-to-liquid ratio, to bald at 50-80 DEG C
Sore flower herb dry powder (by taking 100 g as an example) is stirred or ultrasonic wave assisted extraction, continuous extraction 3-5 times, every time 2 h.Every time
After extraction, extracting solution is filtered out while hot, and then plant residue is carried out again to repeat extraction with fresh solvent.Merge all extractions
Liquid is stored at room temperature overnight, and decompression filters out sediment.By gained filtrate at 40 DEG C evaporating solvent under reduced pressure, to obtain bottle green paste
24 g(A of extract), recovery rate 24%.
Extract A is dissolved in the methanol aqueous solution of 100 mL 25%, successively uses petroleum ether, chloroform and extracting n-butyl alcohol,
Every kind of solvent continuous extraction is three times.The each dosage of petroleum ether is 100 mL, and dosage is 50 mL, n-butanol three to chloroform three times
Secondary dosage is followed successively by 50,40,30 mL.Merge the extract liquor of each same solvent, and evaporating solvent under reduced pressure respectively, successively obtains petroleum
2.4 g(P of ether extract), 2.1 g(C of chloroform extract) and 9.8 g(B of n-butyl alcohol extract).By the water after extracting n-butyl alcohol
Phase evaporated under reduced pressure obtains 9.7 g(H of the hydrotrope).
Two, in the favus of the scalp flower extract effective component separation and identification:
1. the separation of effective component in chloroform extract
1.3 g chloroform extract C are taken, using 3.5 × 28 cm chromatographic columns, 200-300 mesh silica gel, dry method loading carries out column
Chromatography.Eluant, eluent is followed successively by chloroform-methanol (10:1; 9:1;8:1).Successively obtain F1, F2(1.05 g), F3(45.2
Mg), F4(29.4 mg) and F5(90.8 mg) part.
Using identical chromatographic column and silica gel, column chromatography for separation is carried out to the part F1.Eluant, eluent is chlorofonn-ethylacetate
(7:1; 5:1; 3:1;2:1), SF1(41 mg is obtained) part.Silica gel thin-layer chromatography separation is carried out to SF1, solvent is chloroform-
Ethyl acetate (6:1) obtains monomeric compound TCH-12(Chelerythrine) (3.3 mg), TCH-13(sanguinarine alkali) (2.8
Mg).
F3-F5 is merged, silica gel thin-layer chromatography preparative separation is carried out, solvent is chloroform-methanol (20:1), obtains list
Body compound TCH-7((6aS)-2,10,11-Trimethoxy-6-methyl-5,6,6a,7-tetrahydro-4H-dibenzo[de,g) (7.3 mg) and TCH-8(isocorydine) (6.8 mg).
2. the separation of effective component in n-butyl alcohol extract
1 g n-butyl alcohol extract B is taken, with 5 mL methylene chloride, after 5 min of ultrasonication, filtering.Insoluble matter is collected,
And 5 mL methanol are added thereto, after 5 min of ultrasonication, filter out insoluble matter.Filtrate is with 0.22 micron of ultrafiltration membrance filter, institute
It obtains filtrate and carries out C18 reversed-phase column column chromatography, wet process loading.With polarity be incremented by methanol-water (10%, 20%, 30%, 40%, 50%,
60%, 70%, 80%, 90%) carry out gradient elution, about 100 mL of each gradient of 10% -60% eluent, 70% -90% eluent
About 500 mL of each gradient.By 70% methanol-eluted fractions (UV365Down it is in yellow fluorescence) evaporated under reduced pressure, obtain monomeric compound TCH-
11(coptisine).
2.4 g n-butyl alcohol extract B are taken, silica gel (110 g) pillar layer separation is carried out.Chromatographic column specification is 3.5 × 28
Cm, dry method loading.Eluant, eluent is chloroform-methanol (6:1; 4:1; 1:1;1:2), the part BF1-F9 is obtained.Wherein BF2, BF4,
The quality of BF6, BF7, BF8, BF9 point is than being 91,82,119,509,32,340 mg.
BF6(119.4 mg) and BF7(509.5 mg) is merged, column chromatography is carried out with LH-20 column, is eluted with methanol, according to
It is secondary to obtain BF6-1(298 mg) and BF6-2(172 mg) part.BF6-1 and BF6-2 is merged, silica gel column chromatography, chromatographic column are carried out
Specification is 3.5 × 28 cm, and silica gel is 200-300 mesh, and eluant, eluent is followed successively by chloroform-methanol (6:1; 4:1; 3:1;2:1),
It obtains 117 mg white solids (TCH-3, Biflorine).
Thin-layer chromatography preparative separation is carried out to the part BF8 (32.3 mg), solvent is methanol-water (1:1), is collected 365
It is in the substance of sky blue spot under nm, obtains 7.6 mg pale yellow powder shape solids (TCH-4, magnoflorine).
Two, the physicochemical property of monomeric compound and Spectrum Analysis in slenderstalk dicranostigma herb:
Chelerythrine (TCH-12), yellow powder are dissolved in chloroform, are soluble in methanol.It meets Dragendorff's reagent and shows orange red
Color.m.p. 199–200 ℃ (H2O–MeOH); 13C-NMR (125 MHz, CD3OD) δ107.3,151.0,150.9,
105.3,121.8,133.5,152.1,120.1,147.6,151.8,127.6,120.9,130.1,127.2,119.7,63.2,
57.8,132.8,134.3,104.5,53.2.1H-NMR (CDOD3, TMS) δ9.92 (1H, s), 8.60 (1H, d, J
=9.0 Hz), 8.56 (Hz of 1H, d, J=9.0), 8.10 (Hz of 1H, d, J=9.0), 8.08 (1H, s), 8.10
(Hz of 1H, d, J=9.0), 7.49 (1H, s), 6.26 (2H, s), 4.97 (3H, s), 4.27 (3H, s), 4.12 (3H,
s); ESI–MS m/z 348 [M]+.
Sanguinarine (TCH-13), blood red powder meet Dragendorff's reagent and show orange red.m.p. 244–245 ℃
(H2O–MeOH); 13C-NMR (125 MHz, CD3OD) δ107.2,150.6,150.6,105.2,121.8,133.0,
150.7,111.1,148.1,149.3,121.4,118.4,128.9,127.4,119.8,133.0,133.9,104.3,
106.5,53.2.1H-NMR (CDOD3) δ9.95 (1H, s), 8.57 (Hz of 1H, d, J=8.9), 8.48 (1H, d,
The Hz of J=8.8), 8.19 (Hz of 1H, d, J=8.9), 8.13 (1H, s), 7.95 (Hz of 1H, d, J=8.8),
7.55 (1H, s), 6.54 (2H, s), 6.30 (2H, s), 4.49 (3H, s); ESI–MSm/z 332[M]+.
Coptisine (TCH-11), yellow powder dissolve in DMSO and 50 DEG C of methanol.In UV365Lower displaing yellow fluorescence meets iodine
Change bismuth potassium reagent and shows orange red.13C-NMR (125 MHz, CD3OD) δ150.2,148.1,147.5,145.0,144.2,
137.2,132.7,131.0,122.2,121.5,121.4,120.9,112.0,108.8,105.7,104.9,102.5,55.8,
26.7；1H-NMR (CDOD3) δ9.81 (1H, s), 8.83 (1H, s), 7.97 (1H, d,J=8.4), 7.84
(1H, d, J=8.2 Hz), 7.71 (1H, s), 7.06 (1H, s), 6.49 (2H, s), 6.14 (2H, s), 4.85
(2H, brs), 3.19 (2H, brs).
Corydaline (TCH-7), white powder dissolve in chloroform and methanol and acetone.It meets Dragendorff's reagent and shows orange red
。13C-NMR (125 MHz, CDCl3) δ151.8,149.2,143.8,142.3,130.7,127.9,126.4,124.4,
123.9,119.2,111.3,110.8,62.7,62.0,56.0,52.7,43.9,35.4,28.9；1H-NMR (CDCl3) δ
8.72 (1H, s), 7.09 (1H, d,J=8.2 Hz), 6.88 (1H, d,J=8.2 Hz), 6.70 (1H, s),
3.92 (3H, s), 3.91 (3H, s), 3.74 (3H, s), 3.18 (1H, m), 3.06 (1H, d-like,J =
13.3 Hz), 3.04 (1H, d-like,J=13.3 Hz), 2.98 (Hz of 1H, d-like, J=12.8), 2.68
(Hz of 1H, d-like, J=16.0), 2.56 (3H, s), 2.55 (1H, m), 2.44 (1H, t,J = 13.0
Hz)。
Isocorydine (TCH-10), colourless powder dissolve in chloroform, methanol, in UV365Aobvious blue-fluorescence down.Meet iodate
Bismuth potassium reagent shows orange red.13C-NMR (125 MHz, CD3OD) δ151.7,149.1,143.3,142.4,129.8,
129.7,128.0,125.3,119.8,119.1,111.5,111.2,62.9,60.9,55.3,55.0,52.3,42.4,
34.9 28.2；1H-NMR (CDOD3) δ 6.93 (1H, d, J = 8.1), 6.87 (1H, d,J = 8.1), 6.86
(1H, s), 3.89 (3H, s), 3.87 (3H, s), 3.65 (3H, s), 3.10 (1H, dd, J=3.5,13.0,
Hz), 3.10 (1H, dd,J = 13.2,3.4, Hz), 3.06 (1H, dd, J=6.0,11.5 Hz), 2.85
(Hz of 1H, d-like, J=13.0), 2.76 (1H, dd,J = 16.6,3.6 Hz), 2.54 (3H, s), 2.51
(1H, 2 × t, J=4.0,12.0 Hz), 2.38 (Hz of 1H, t, J=13.0).
Biflorine (TCH-3), white powder dissolve in chloroform, methanol.It meets Dragendorff's reagent and shows orange red.1H
NMR (400 MHz,CDCl3)δ6.91 (s, 1H), 6.65 (1H, s), 2.56(4H, br s), 1.92 (3H, s),
3.59 (2H, br s), 6.67 (1H, d, J = 8.0 Hz), 6.68 (1H, d, J = 8.0 Hz), 3.92
(2H, br s), 5.95 (2H, s), 5.93 (2H, s); 13C NMR (100 MHz, CDCl3)δ194.9, 148.0,
146.3, 146.0, 145.9, 136.1 132.7, 128.9, 125.0, 117.8, 110.5, 108.1, 106.7,
100.8, 101.2, 57.7, 50.8, 46.4, 41.4, 31.8. EI-MS m/z 353 [M]+, 338, 309,
281, 267, 252, 223, 209, 190, 163, 148, 134, 91.
Magnoflorine (TCH-4), pale yellow powder is dissolved in chloroform, is slightly soluble in methanol, in UV365Aobvious blue-fluorescence down, with
Dragendorff's reagent shows punctation.
1H NMR (500 MHz, CDOD3)δ6.64 (1H, d, J=8.0 Hz), 6.35 (1H, s), 6.42
(1H, d, J=8.0 Hz), 3.85 (3H, s), 3.75 (3H, s), 3.62 (1H, br d, J=14.3 Hz),
3.20 (1H, m), 3.11 (3H, s), 3.02 (2H, m), 2.82 (Hz of 1H, d, J=10.0), 2.65 (3H,
S), 2.43 (Hz of 1H, d-like, J=13.0), 2.25 (Hz of 1H, t, J=13.0);13C NMR (125 MHz,
CDOD3)δ152.8,151.6,150.7,149.8,126.1,123.4,123.3,117.0,115.8,121.1,110.4,
109.3,70.8,62.1,55.0,54.7,53.8,43.6,31.6,24.6；
Three, (EThe antibacterial activity of)-cinnamate derivative compound:
1, for trying bacterium:
Fusarium graminearum (Fusariumg graminearum), rice blast fungus (Pyricularia grisea),
Maize Curvularia leaf spot fungi (Curvularia lunata), Valsa mali (Valsa mali), tomato early blight bacterium
(Alternaria solani), cotton-wilt fusarium (Fusarium oxysporium f. sp. Vasinfectum), watermelon
Wilt (Fusarium oxysporium f. sp. Niveum), dry rot of potato bacterium (Fusarium solani),
Alternaria brassicae (Alternaria brassicae), tobacco brown spot pathogen (Alternaria alternate), pumpkin it is withered
Wither germ (Mycosphaerella melonis), botrytis cinerea (Botrytis cinerea)
2, sample preparation:
The monomeric compound for weighing 40 mg crude extracts or extract or 10.0 mg is dissolved in the DMSO (v/ of 10 mL 5%
V), spare after using ultraviolet lamp radiation sterilization 30 minutes on the super-clean bench.
3, the preparation of PDA culture medium:
200.0 g of peeled potatoes is shredded, 1000 mL water are added, boil 30 min, filtered through gauze, filtrate water constant volume
To 1000 mL, 20.0 g glucose are added, 15.0 g agar powders are divided in triangular flask after heating dissolves it all.
4, the measurement of antibacterial activity:
Antibacterial activity is carried out using inhibition mycelial growth rate method.By 10 mL test liquids of above-mentioned preparation, 190 mL are poured into
In in the PDA culture medium of molten state after sterilizing, quickly poured into while hot after mixing in 13 sterile petri dish to get containing 50μg/
ML is for examination monomeric compound or the culture medium of 2.0 mg/mL extracts；Using the PDA culture medium containing 0.25% DMSO as blank pair
According to.After culture medium solidification, made with the punch that diameter is 0.5 cm from for the eugonic place of examination bacterium colony edge mycelia
Bacteria cake is taken, carefully bacteria cake is placed in above pastille culture medium with transfer needle.The mycelia of bacteria cake is face-down.Three bacteria cakes of every ware,
It point is put in the center of culture dish with triangle, after then covering and mark, is placed in the incubator of 25 DEG C and 80% humidity and cultivates.
Each processing is in triplicate.After cultivating 72 h, takes crossing method to measure colony diameter, its average value is taken, by following formula
Calculate the bacteriostasis rate of each test compound.
Bacterium colony extends diameter/cm=colony diameter average value 0.5(bacteria cake diameter)
The test result of slenderstalk dicranostigma herb alcohol extracts and each solvent extract (2 mg/mL) is listed in the table below.The result shows that bald
Sore flower alcohol extracts show different degrees of inhibitory activity for examination bacterium to all, and active constituent is concentrated mainly on chlorine
In imitative extract and n-butyl alcohol extract.
7 kinds of monomeric compounds (50 in slenderstalk dicranostigma herbμG/mL) test result of 12 kinds of plant pathogenic fungis is listed in the table below.
The title and number of each compound are respectively as follows: Chelerythrine (TCH-12), sanguinarine (TCH-13), coptisine (TCH-11),
(6aS)-2,10,11-Trimethoxy-6-methyl-5,6,6a,7-tetrahydro-4H-dibenzo[de,g (TCH-7), isocorydine (TCH-10), Biflorine (TCH-3), magnoflorine (TCH-4).
The result shows that Chelerythrine (TCH-12), sanguinarine (TCH-13) and magnoflorine (TCH-4) are to 12 kinds of plants
Disease fungus all has stronger inhibitory activity, is better than positive drug probenazole to the activity of individual bacterium.
Toxicity equation and medium effective concentration (EC of the magnoflorine to 7 kinds of phytopathogens50) value is listed in the table below.As a result table
It is bright, EC of the magnoflorine to 7 kinds of phytopathogens50For 10-38 μ g/ml, average EC50For 23.4 μ g/ml, have directly as
Plants antimicrobial effective component is used to prepare the potentiality of plants antimicrobial drug.
Fig. 1 is the high-efficient liquid phase chromatogram of slenderstalk dicranostigma herb alcohol extracts.The result shows that slenderstalk dicranostigma herb alcohol extracts is main
Ingredient is isocorydine, magnoflorine and coptisine, content of the three in slenderstalk dicranostigma herb be respectively 1.14%, 0.2%,
0.095%.The content of other compositions is less.
The activity and its content in slenderstalk dicranostigma herb of comprehensive each monomeric compound, can determine main antibacterial in slenderstalk dicranostigma herb
Referred to as magnoflorine.
It can be seen that favus of the scalp flower extract of the present invention and its effective component have wider resist to phytopathogen
Bacterium spectrum and stronger antibacterial activity, have the potential use for being used to prepare plants antimicrobial drug, can be used as plants antimicrobial drug
Effective component.
The contents of the present invention are not limited to cited by embodiment, and those of ordinary skill in the art are by reading description of the invention
And to any equivalent transformation that technical solution of the present invention is taken, all are covered by the claims of the invention.
Claims (2)
1. the application of favus of the scalp flower extract, it is characterised in that:
The extract is as the application for preparing plants antimicrobial drug；
The slenderstalk dicranostigma herb is Papaveraceae (Papaveraceae) convex combination algorithm (Dicranostigma) herbaceos perennial favus of the scalp
Flower (Dicranostigma leptopodum (maxim.) fedde), the favus of the scalp flower extract are slenderstalk dicranostigma herb herb or ground
Partial alcohol extract or water extract；
The antimicrobial component for including in the favus of the scalp flower extract be magnoflorine, molecular characterization:
。
2. the application of favus of the scalp flower extract according to claim 1, it is characterised in that:
The extract has inhibitory activity to following phytopathogen:
Apple decay pathogen；Gibberella saubinetii pathogen；Early blight of tomato opportunistic pathogen；Curvularia pathogen；Pumpkin is withered cause of disease
Bacterium；Cotton is withered, withered germ of water-melon；Dry rot of potato opportunistic pathogen；Alternaria brassicae；Tobacco brown spot pathogen；Apple anthrax
Germ；Rice blast fungus；Botryosphaeria berengeriana f. sp；Tomato Cercospora Sojina Hara.
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| RU2821582C1 (en) * | 2023-11-02 | 2024-06-25 | Федеральное государственное бюджетное научное учреждение "Федеральный научный центр агробиотехнологий Дальнего Востока им. А.К. Чайки" (ФГБНУ "ФНЦ агробиотехнологий Дальнего Востока им. А.К. Чайки") | Method of potato late blight control |
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| CN108693289B (en) * | 2018-05-28 | 2020-07-14 | 贵阳中医学院 | Method for determining content of magnoflorine in herringbone fruit medicinal material |
| CN110437152A (en) * | 2019-09-03 | 2019-11-12 | 郑州铁路职业技术学院 | The extraction separation method of magnoflorine in a kind of slenderstalk dicranostigma herb |
| CN110372591A (en) * | 2019-09-03 | 2019-10-25 | 郑州铁路职业技术学院 | The extraction separation method of corydaline and allopurine base in a kind of slenderstalk dicranostigma herb |
| CN110780020A (en) * | 2019-12-06 | 2020-02-11 | 郑州铁路职业技术学院 | Detection method for simultaneously determining ten alkaloids in tinea capitis flowers by HPLC |
| CN111560016A (en) * | 2020-05-11 | 2020-08-21 | 郑州铁路职业技术学院 | Method for extracting and separating coptisine from celandine |
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Citations (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN102000158A (en) * | 2010-10-29 | 2011-04-06 | 王廷璞 | Extraction method of Dicranostigma leptodum (Maxim.) Fedde alkaloid and extract obtained by same |
| CN102731398A (en) * | 2011-04-02 | 2012-10-17 | 中国科学院兰州化学物理研究所 | Extraction separation preparation method of isocorydione having anticancer activity |
| CN103977082A (en) * | 2014-05-16 | 2014-08-13 | 中国农业科学院兰州畜牧与兽药研究所 | Medicinal composition as well as preparation method and application thereof |
| CN104072418A (en) * | 2013-03-29 | 2014-10-01 | 中国科学院兰州化学物理研究所 | Preparation technique for separating and purifying isocorydine from macroporous resin |
| CN105250391A (en) * | 2014-07-17 | 2016-01-20 | 中国科学院兰州化学物理研究所 | Dicranostigma leptopodum (maxim) fedde alkaloid effective part preparation method |
-
2016
- 2016-11-01 CN CN201610935462.1A patent/CN106565724B/en active Active
Patent Citations (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN102000158A (en) * | 2010-10-29 | 2011-04-06 | 王廷璞 | Extraction method of Dicranostigma leptodum (Maxim.) Fedde alkaloid and extract obtained by same |
| CN102731398A (en) * | 2011-04-02 | 2012-10-17 | 中国科学院兰州化学物理研究所 | Extraction separation preparation method of isocorydione having anticancer activity |
| CN104072418A (en) * | 2013-03-29 | 2014-10-01 | 中国科学院兰州化学物理研究所 | Preparation technique for separating and purifying isocorydine from macroporous resin |
| CN103977082A (en) * | 2014-05-16 | 2014-08-13 | 中国农业科学院兰州畜牧与兽药研究所 | Medicinal composition as well as preparation method and application thereof |
| CN105250391A (en) * | 2014-07-17 | 2016-01-20 | 中国科学院兰州化学物理研究所 | Dicranostigma leptopodum (maxim) fedde alkaloid effective part preparation method |
Non-Patent Citations (3)
| Title |
|---|
| 甘肃省陇东南地区特色药用植物红茂草资源的研究与利用;赵强;《甘肃农业大学博士学位论文》;20140215;第6-12、37、62-63、69、79页 |
| 秃疮花中异喹啉类生物碱的分离与分析方法研究;李敏;《兰州理工大学硕士学位论文》;20131215;第13、16-20页 |
| 红茂草生物碱抑菌活性的测定;赵强;《中国兽医科学》;20081231;第38卷(第12期);第1098-1101页，尤其第1098页右栏末段，第1099页左栏末段 |
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| RU2821582C1 (en) * | 2023-11-02 | 2024-06-25 | Федеральное государственное бюджетное научное учреждение "Федеральный научный центр агробиотехнологий Дальнего Востока им. А.К. Чайки" (ФГБНУ "ФНЦ агробиотехнологий Дальнего Востока им. А.К. Чайки") | Method of potato late blight control |
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