CN107459474A - A kind of alkaloid and its extracting method and application - Google Patents
A kind of alkaloid and its extracting method and application Download PDFInfo
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- CN107459474A CN107459474A CN201710833304.XA CN201710833304A CN107459474A CN 107459474 A CN107459474 A CN 107459474A CN 201710833304 A CN201710833304 A CN 201710833304A CN 107459474 A CN107459474 A CN 107459474A
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D207/00—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom
- C07D207/02—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom with only hydrogen or carbon atoms directly attached to the ring nitrogen atom
- C07D207/30—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having two double bonds between ring members or between ring members and non-ring members
- C07D207/32—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having two double bonds between ring members or between ring members and non-ring members with only hydrogen atoms, hydrocarbon or substituted hydrocarbon radicals, directly attached to ring carbon atoms
- C07D207/33—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having two double bonds between ring members or between ring members and non-ring members with only hydrogen atoms, hydrocarbon or substituted hydrocarbon radicals, directly attached to ring carbon atoms with substituted hydrocarbon radicals, directly attached to ring carbon atoms
- C07D207/333—Radicals substituted by oxygen or sulfur 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
- A01N43/34—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with one nitrogen atom as the only ring hetero atom
- A01N43/36—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with one nitrogen atom as the only ring hetero atom five-membered rings
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07B—GENERAL METHODS OF ORGANIC CHEMISTRY; APPARATUS THEREFOR
- C07B2200/00—Indexing scheme relating to specific properties of organic compounds
- C07B2200/13—Crystalline forms, e.g. polymorphs
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Abstract
The invention discloses a kind of alkaloid and its extracting method and application, by nerville knotweed dried root raw material with alcohol steep several times, merge extract solution and simultaneously filter, reclaim ethanol, obtain ethanol coarse extract；Ethanol coarse extract is air-dried and obtains powdered extract, then water is added to powdered extract, is mixed into uniform solution A, solution A is then used into ethyl acetate and extracting n-butyl alcohol respectively, obtains n-butanol medicinal extract；It is respectively 100 with volume gradient by n-butanol medicinal extract on silica gel chromatographic column:0、100:100、100:30、100:50、100:100、0:100 ethyl acetate/methanol eluant, eluent is eluted, and obtains six components of A F, and component A is again 100 with volume gradient:30、100:50、100:80、100:150、0:100 petrol ether/ethyl acetate eluant, eluent is eluted, and obtains five components of A1 A5, and A1 components are recrystallized with methanol, obtain alkaloid.The novel compound nerville knotweed alkaloid of present invention structure isolated from nerville knotweed dried root, and the alkaloid has certain bacteriostatic activity.
Description
Technical field
The present invention relates to alkaloid preparation field, and in particular to a kind of alkaloid and its extracting method and application.
Background technology
Nerville knotweed (Fallopia multiflora (Thunb.) Harald.var.cillinerve (Nakai) A.J.Li)
For polygonaceae fleece-flower root category medicinal plant, its dried root also makees polygonum cill or Ciliatenerve Knotweed Root in addition to as Girald Pteroxygonum Root, in the Northwest
Medicinal, producing Qinling Mountains in Shaanxi and each county of Daba Mountain, Hubei, Sichuan, Guizhou also has a small amount of distribution.Gas is micro-, bitter, micro-puckery, cool in nature, has
The functions such as clearing heat and detoxicating, cooling blood and hemostasis, wind-damp dispelling, strong waist and knee, for gastroenteritis, bacillary dysentery, tonsillitis, irregular menstruation, function
Property uterine hemorrhage etc..Modern pharmacology research confirms that it has the activity of stronger antibacterial, antiviral etc..
Root mainly contains it is reported that mainly using the dried root of nerville knotweed as research object in nerville knotweed dried root
The compounds such as Anthraquinones, flavonoids, polysaccharide, glycoside, it is respectively provided with certain bioactivity.But having no in plant nerville knotweed has
Close the report of alkaloid.
The content of the invention
It is an object of the invention to provide a kind of alkaloid and its extracting method and application, to overcome above-mentioned prior art to deposit
The defects of, the present invention novel compound nerville knotweed new alkaloids of isolated structure from nerville knotweed dried root, and
The alkaloid has certain bacteriostatic activity.
To reach above-mentioned purpose, the present invention adopts the following technical scheme that：
A kind of alkaloid, the chemical structural formula of the alkaloid are：
A kind of extracting method of alkaloid, comprises the following steps：
(1) by nerville knotweed dried root raw material with alcohol steep several times, merge extract solution simultaneously filter, reclaim ethanol, filter
Liquid is concentrated into no alcohol taste, obtains ethanol coarse extract；
(2) the obtained ethanol coarse extract of step (1) is air-dried, obtains powdered extract, then add water to powdered extract,
Uniform solution A is mixed into, the mass ratio of powdered extract and water is 1 in solution A:3, then solution A is first extracted with ethyl acetate
Take, then with extracting n-butyl alcohol, obtain n-butanol medicinal extract；
(3) the n-butanol medicinal extract for obtaining step (2) is respectively 100 with volume gradient on silica gel chromatographic column:0、100:
100、100:30、100:50、100:100、0:100 ethyl acetate/methanol eluant, eluent is eluted, and obtains six components of A-F,
Component A continues on silica gel chromatographic column, is 100 with volume gradient:30、100:50、100:80、100:150、0:100 oil
Ether/ethyl acetate eluant, eluent is eluted, and obtains five components of A1-A5, and A1 components are recrystallized with methanol, obtain biology
Alkali.
Further, in addition to step (4)：The alkaloid for taking step (3) to obtain is fitted into container A after being dissolved in DMSO, will
Container A is placed in the container B for filling ether solvent, is then sealed the mouth of container B, and standing treats that crystal separates out, and obtains the biology
The monocrystalline of alkali.
Further, the ethanol in step (1) is the industrial alcohol that volume fraction is 95%.
Further, by nerville knotweed dried root raw material alcohol steep 3 times in step (1).
Further, 15mg alkaloids are dissolved in the DMSO in step (4) per 50mL.
Application of the alkaloid on antibacterial.
Further, the antibacterial inhibitory action referred to bacterium or fungi.
Further, the antibacterial inhibitory action referred to Sclerotinia sclerotiorum.
Compared with prior art, the present invention has technique effect beneficial below：
The nerville knotweed alkaloid of the present invention is a kind of novel alkaloid compound of structure, and its molecular formula is
C18H23NO3, it is of the invention by being extracted to nerville knotweed in addition, this alkaloid is obtained, by the antibacterial of alkaloid of the present invention
Active testing, it is found that the compound has certain antifungal activity, especially have good bacteriostatic activity to Sclerotinia sclerotiorum, be
The bacteriostatic active ingredients of nerville knotweed dried root, therefore, can be used for cultural control and Efficacy of Pesticide.
Brief description of the drawings
Fig. 1 is alkaloid of the present invention1H-NMR is composed；
Fig. 2 is alkaloid of the present invention13C-NMR is composed；
Fig. 3 is (135 °) spectrums of DEPT of alkaloid of the present invention；
Fig. 4 is the spectrum COSY of alkaloid of the present invention；
Fig. 5 is the NOESY of alkaloid of the present invention；
Fig. 6 is the spectrum HSQC of alkaloid of the present invention；
Fig. 7 is the HMBC of alkaloid of the present invention；
Fig. 8 is that the HR-ESI-M of alkaloid of the present invention is composed；
Fig. 9 is the x-ray crystal structure figure of alkaloid of the present invention；
Figure 10 is the structure fragment of alkaloid of the present invention；
Figure 11 is the structure chart of alkaloid of the present invention.
Embodiment
Embodiments of the present invention are described in further detail below：
A kind of alkaloid compound, the chemical structural formula of the compound：
The extracting method of the compound is as follows：
(1) extracted 3 times with 95% industrial alcohol from 1.75Kg nervilles knotweed dried root raw medicinal material, merge extract solution simultaneously
Filtering, reclaims ethanol, and filtrate is concentrated into no alcohol taste, obtains ethanol coarse extract 332.56g；
(2) the ethanol coarse extract for obtaining step (1) air-dries and obtains powdered extract, according to the weight of powdered extract and water ratio
1.0:3.0, toward water is added in described powdered extract, are mixed into homogeneous solution A, and solution A is first extracted with ethyl acetate, then with just
Butanol, before immunoassay, obtain ethyl acetate extract 33.72g, n-butanol medicinal extract 169.54g；
(3) to the n-butanol medicinal extract of step (2), on silica gel chromatographic column, eluted with the ethyl acetate/methanol of different gradients
Agent (100:0,100:100,100:30,100:50,100:100,0:100, v/v) eluted, obtain six components of A-F, A groups
Divide and continue on silica gel chromatographic column, with the petrol ether/ethyl acetate eluant, eluent (100 of different gradients:30,100:50,100:80,
100:150,0:100, v/v) eluted, obtain five components of A1-A5, A1 components are recrystallized with methanol, obtained pure
Net alkaloid 1.47g.
(4) the alkaloid 15mg for taking step (3) to obtain, the DMSO for being dissolved in 50mL are fitted into bottle, and bottle is placed on into Sheng
Have in the big bottle of ether solvent, then seal the mouth of big bottle, standing treats that crystal slowly separates out, and 10 groups of parallel laboratory test, is somebody's turn to do
The monocrystalline of compound.
Nerville knotweed alkaloid prepared by the present invention is a kind of novel alkaloid compound of structure, at present from plant nerville
The report for being separated to such compound is yet there are no in the dried root of knotweed, also has no this isolated compound from other plant
Report, the method that more there are no this artificial synthesized compound.We tie using silica gel column chromatography and again to nerville knotweed dried root
Brilliant method separation identifies the novel alkaloid compound of a structure, and the compound is to report first.
Novel compound of present invention nerville knotweed alkaloid is colorless plate crystal, and HR-ESI-MS is at m/z 324.1582
Provide [M+Na]+Peak, it is C to calculate its molecular formula18H23NO3,1H and13C nuclear magnetic resonance datas are as shown in table 1, the crystal of alkaloid
It is as shown in table 2 to learn data.
The nerville knotweed alkaloid of table 11H and13C nuclear magnetic resonance datas
The nerville knotweed new alkaloids A of table 2 crystallographic data
By testing the bacteriostatic activity of the compounds of this invention, it is found that the compound has certain antifungal activity, especially
There is good bacteriostatic activity to Sclerotinia sclerotiorum, be the bacteriostatic active ingredients of nerville knotweed dried root, therefore, can be used for agriculture
Industry is prevented and treated and Efficacy of Pesticide.
As shown in figures 1-8, alkaloid of the present invention1H-NMR、13C-NMR、DEPT、2D NMR (COSY、NOESY、HSQC、
HMBC) compose, and HR-ESI-M spectrums learn compound structure.Specifically：
1H-NMR(400HZ,DMSO-d6) in spectrum, δH9.51 (1H, s) and 9.25 (1H, s), there are two in prompting structure
Active hydrogen；δH6.68 (2H, d, J=8.4Hz) and 6.94 (2H, d, J=8.4Hz), there is AA'XX''s in prompting structure
Phenol is to substituting fragment；δH7.01 (1H, d, J=4.0Hz) and 6.23 (1H, d, J=4.0Hz), there is one in prompting structure
Individual 2,5- disubstituted pyrroles ring plate section；δH4.36 (2H, t, J=15.2Hz), 4.26 (2H, s), 3.38 (2H, t), 2.81
(2H, t, J=15.2Hz, H-2'), 1.49 (2H, m, H-8), 1.31 (2H, m), six methylene substrates be present in prompting structure
Section；δHAn end position methyl-CH in 0.85 (3H, t, J=14.7) prompting structure be present3Fragment.
13C-NMR (100HZ, DMSO-d6) in spectrum, provide 18 carbon signals, wherein δC179.30 be carbonyl carbon signals；δC
69.29th, 63.09 and 47.11, three methylene being connected with electron-withdrawing group be present in prompting structure；DEPT(135°) spectrum, prompt
Six of which methine carbon, respectively δ in structure also be presentC129.58,123.73,115.15 and 110.78, wherein δC
129.58 and 115.15 be the methine on phenyl ring, because the compound is that phenyl ring substitutes to two, therefore has two pairs of chemical environments
Identical hydrogen and carbon, 123.73 and 110.78 be the methine on pyrrole ring.
Hsqc spectrum provides the information that all hydrogen carbon are joined directly together in structure, as shown in table 1.δH4.26 with δC63.09 Hes
δH3.38 with δC- CH is there may be in 69.29 related prompting structures2-O-CH2- fragment；δH436 and δC47.11 correlation prompting
- CH is there may be in structure2- N- fragments；
δ in HMBC spectrumsH4.26 with δC110.78th, 139.43 is related, prompts structure fragment A1 (as shown in Figure 10) be present；
δH4.36 with δC36.20 is related ,-CH be present in prompting structure2-CH2- fragment；δH4.36 with δC128.37 with 131.77,
139.43 is related, prompts structure fragment A2 be present (as shown in Figure 10)；δH9.51 with δC131.77 is related, is deposited in prompting structure
Structure fragment A3 (as shown in Figure 10).
In NOESY spectrums, δH3.38 is related to 1.49,1.31, δH1.49 is related to 1.31,0.85, exists in prompting structure
Structure fragment-O-CH2CH2CH2CH3, the fragment and A1, A2, A3 part are linked together, compound A knot is finally determined
Structure.The compound is to have no the neoformation alkaloid compound of document report, and related NMR data ownership is as shown in table 1.
X-ray crystal structure figure finally determines the stereochemical structure of the compound.
With reference to embodiment, the present invention will be further described：
Nerville knotweed (Fallopia multiflora (Thunb.) Harald.var.cillinerve (Nakai) A.J.Li)
Dried root 1.75Kg, extracted 3 times with 95% industrial alcohol, merge extract solution and filter, reclaim ethanol, filtrate is concentrated into no alcohol
Taste, obtain ethanol coarse extract 332.56g；Obtained above-mentioned ethanol coarse extract is dried to obtain powdered extract, according to powdered extract with
The weight of water is than 1.0:After 3.0 are mixed into homogeneous aqueous solution, the obtained aqueous solution is first extracted with ethyl acetate, then is extracted with n-butanol
Take, obtain the g of ethyl acetate extract 33.72, n-butanol medicinal extract 169.54g；After above-mentioned n-butanol phase medicinal extract is dissolved with methanol
Mixed with bis- silica gel of 170g and mix sample, using silica gel column chromatography, with the ethyl acetate/methanol eluant, eluent (100 of different gradients:0,
100:100,100:30,100:50,100:100,0:100, v/v) eluted, obtain six components of A-F, component A continues
On silica gel chromatographic column, with the petrol ether/ethyl acetate eluant, eluent (100 of different gradients:30, 100:50,100:80,100:150,
0:100, v/v) eluted, obtain five components of A1-A5, A1 components are recrystallized with methanol, obtain pure biology
Alkali cpd 1.47g；Above-mentioned compound 15mg, the DMSO for being dissolved in 50mL is taken to be fitted into bottle, bottle is placed on and fills second
In the big bottle of ether solvents, then the mouth of big bottle is sealed, standing treats that crystal slowly separates out, and 10 groups of parallel laboratory test, obtains the chemical combination
The monocrystalline of thing.
Alkaloid compound nerville knotweed new alkaloids A antibacterial activity experiment：
1st, experiment material
1.1st, given the test agent
Nerville knotweed alkaloid is dissolved with DMSO, is made into 500 μ g/mL solution.
1.2nd, bacterial strain
Two plants of gram-positive bacterias (staphylococcus aureus, streptococcus lactis), two plants of Gram-negative bacteria (large intestine bars
Bacterium, Pseudomonas aeruginosa).
1.3rd, culture medium
Beef extract 3.0g/L, NaCL 5.0g/L, peptone 10.0g/L, pH 7.2-7.4.
1.4th, other materials
96 orifice plates.
2nd, experimental method
96 orifice plates add the 100 above-mentioned culture mediums of μ L per hole, and 100 μ L concentration are 1 × 106CFU/mL cell suspension, first
The μ g/mL of Kong Zhongjia 500 sample solution, sample concentration is set to be followed successively by 500 from the first hole to the tenth hole using doubling dilution,
250,125,62.5,31.2,15.6,7.81,3.91,1.95 and 0.975 μ g/mL, 11-holes and the 12nd hole are separately added into
The above-mentioned culture mediums of 100 μ L and DMSO are as control.From positive control of the Benzylpenicillin sodium salt as Gram positive bacteria, sulfate chain
Mycin is as the positive control that Glan is a negative bacterium.Above-mentioned 3 parallel laboratory tests of every group of carry out, 96 orifice plates are placed in 37 DEG C of cultures
It is incubated one day in case.
3rd, experimental result
3 are the results are shown in Table, is as a result shown, nerville knotweed alkaloid has certain inhibitory activity to Escherichia coli and Pseudomonas aeruginosa,
MIC (minimal inhibitory concentration) is 62.5 μ g/mL.
Alkaloid compound nerville knotweed new alkaloids A antifungal activity experiment：
1st, experiment material
1.1st, given the test agent
Nerville knotweed alkaloid is dissolved with DMSO, is made into 500 μ g/mL solution.
1.2nd, bacterial strain
Seven plants of plant pathogenic fungis (apple rot pathogen, Exserohilum turcicum, botrytis cinerea, Alternaria alternates
Bacterium, Sclerotinia sclerotiorum, Peony Anthracnose, gibberella saubinetii).
1.3rd, culture medium
200g potato leaching juices, glucose 20g, water 1L.
1.4th, other materials
96 orifice plates.
2nd, experimental method
96 orifice plates per hole add the 100 above-mentioned culture mediums of μ L, 100 μ L concentration be 1 × 106CFU/mL cell suspension, first
The μ g/mL of Kong Zhongjia 500 sample solution, sample concentration is set to be followed successively by 500 from the first hole to the tenth hole using doubling dilution,
250,125,62.5,31.2,15.6,7.81,3.91,1.95 and 0.975 μ g/mL, 11-holes and the 12nd hole are separately added into
The above-mentioned culture mediums of 100 μ L and DMSO are as control.From positive control of the carbendazim as plant pathogenic fungi.Above-mentioned every group
3 parallel laboratory tests are carried out, 96 orifice plates are placed in 28 DEG C of incubators and are incubated two days.
3 are the results are shown in Table, is as a result shown, nerville knotweed alkaloid has certain suppression to Exserohilum turcicum and tobacco brown spot pathogen
System activity, MIC (minimal inhibitory concentration) is 62.5 μ g/mL, there is suitable inhibitory activity, MIC (minimum suppressions to Sclerotinia sclerotiorum
Bacteria concentration) it is 31.2 μ g/mL.
The bacteriostatic activity of the nerville knotweed alkaloid of table 3
Wherein：A:Escherichia coli；B:Pseudomonas aeruginosa；C：Staphylococcus aureus；D：Streptococcus lactis； E：Apple tree is rotten
Rotten germ；F：Gibberella saubinetii；G：Exserohilum turcicum；H：Tobacco brown spot pathogen；I：Sclerotinia sclerotiorum；J：Graw mold of tomato
Bacterium；K：Peony Anthracnose；-：It is not provided with testing.
Claims (9)
1. a kind of alkaloid, it is characterised in that the chemical structural formula of the alkaloid is：
2. a kind of extracting method of alkaloid, it is characterised in that comprise the following steps：
(1) by nerville knotweed dried root raw material with alcohol steep several times, merge extract solution and simultaneously filter, reclaim ethanol, filtrate is dense
No alcohol taste is reduced to, obtains ethanol coarse extract；
(2) the obtained ethanol coarse extract of step (1) is air-dried, obtains powdered extract, then add water, mixing to powdered extract
Into uniform solution A, the mass ratio of powdered extract and water is 1 in solution A:3, then solution A is first extracted with ethyl acetate, then
With extracting n-butyl alcohol, n-butanol medicinal extract is obtained；
(3) the n-butanol medicinal extract for obtaining step (2) is respectively 100 with volume gradient on silica gel chromatographic column:0、100:100、
100:30、100:50、100:100、0:100 ethyl acetate/methanol eluant, eluent is eluted, and obtains six components of A-F, A groups
Divide and continue on silica gel chromatographic column, be 100 with volume gradient:30、100:50、100:80、100:150、0:100 petroleum ether/
Ethyl acetate eluant, eluent is eluted, and obtains five components of A1-A5, and A1 components are recrystallized with methanol, obtain alkaloid.
3. the extracting method of a kind of alkaloid according to claim 2, it is characterised in that also including step (4)：Take step
(3) alkaloid obtained is fitted into container A after being dissolved in DMSO, and container A is placed in the container B for filling ether solvent, then will
The mouth of container B is sealed, and standing treats that crystal separates out, and obtains the monocrystalline of the alkaloid.
4. the extracting method of a kind of alkaloid according to claim 2, it is characterised in that the ethanol in step (1) is body
Fraction is 95% industrial alcohol.
5. the extracting method of a kind of alkaloid according to claim 2, it is characterised in that step does nerville knotweed in (1)
Dry root tuber raw material alcohol steep 3 times.
A kind of 6. extracting method of alkaloid according to claim 2, it is characterised in that per 50mL in step (4)
15mg alkaloids are dissolved in DMSO.
7. the alkaloid described in a kind of claim 1, or prepared by the extracting method of any one of claim 2-5 alkaloid
Application of the alkaloid on antibacterial.
8. application according to claim 7, it is characterised in that the antibacterial inhibitory action referred to bacterium or fungi.
9. application according to claim 7, it is characterised in that the antibacterial inhibitory action referred to Sclerotinia sclerotiorum.
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Cited By (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN109700859A (en) * | 2019-03-13 | 2019-05-03 | 陕西科技大学 | Polygonum cill is preparing the application in antifungal drug and its synergist |
| CN112794812A (en) * | 2021-01-15 | 2021-05-14 | 广西壮族自治区农业科学院 | Alkaloid compound extracted from banana flower and extraction method thereof |
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| CN102942516A (en) * | 2012-11-05 | 2013-02-27 | 宁波大学 | Alkaloid compound and preparation method and application of alkaloid compound |
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2017
- 2017-09-15 CN CN201710833304.XA patent/CN107459474A/en active Pending
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| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN102942516A (en) * | 2012-11-05 | 2013-02-27 | 宁波大学 | Alkaloid compound and preparation method and application of alkaloid compound |
| CN103275012A (en) * | 2013-06-08 | 2013-09-04 | 中国科学院过程工程研究所 | Preparation method and application of Maca alkaloid |
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Cited By (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN109700859A (en) * | 2019-03-13 | 2019-05-03 | 陕西科技大学 | Polygonum cill is preparing the application in antifungal drug and its synergist |
| CN109700859B (en) * | 2019-03-13 | 2021-11-16 | 陕西科技大学 | Application of radix notoginseng cinnabaris in preparation of antifungal drugs and synergists thereof |
| CN112794812A (en) * | 2021-01-15 | 2021-05-14 | 广西壮族自治区农业科学院 | Alkaloid compound extracted from banana flower and extraction method thereof |
| CN112794812B (en) * | 2021-01-15 | 2022-06-03 | 广西壮族自治区农业科学院 | Alkaloid compound extracted from banana flower and extraction method thereof |
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