CN105622686A - Alkaloid compound and preparation method as well as application thereof - Google Patents

Alkaloid compound and preparation method as well as application thereof Download PDF

Info

Publication number
CN105622686A
CN105622686A CN201610014222.8A CN201610014222A CN105622686A CN 105622686 A CN105622686 A CN 105622686A CN 201610014222 A CN201610014222 A CN 201610014222A CN 105622686 A CN105622686 A CN 105622686A
Authority
CN
China
Prior art keywords
compound
column chromatography
alkaloid
alkaloid compound
preparation
Prior art date
Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
Granted
Application number
CN201610014222.8A
Other languages
Chinese (zh)
Other versions
CN105622686B (en
Inventor
印敏
徐曙
杨简赛
冯煦
王鸣
单宇
管福琴
王奇志
王碧
刘飞
陈雨
赵兴增
Current Assignee (The listed assignees may be inaccurate. Google has not performed a legal analysis and makes no representation or warranty as to the accuracy of the list.)
Institute of Botany of CAS
Original Assignee
Institute of Botany of CAS
Priority date (The priority date is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the date listed.)
Filing date
Publication date
Application filed by Institute of Botany of CAS filed Critical Institute of Botany of CAS
Priority to CN201610014222.8A priority Critical patent/CN105622686B/en
Publication of CN105622686A publication Critical patent/CN105622686A/en
Application granted granted Critical
Publication of CN105622686B publication Critical patent/CN105622686B/en
Active legal-status Critical Current
Anticipated expiration legal-status Critical

Links

Classifications

    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07H—SUGARS; DERIVATIVES THEREOF; NUCLEOSIDES; NUCLEOTIDES; NUCLEIC ACIDS
    • C07H17/00—Compounds containing heterocyclic radicals directly attached to hetero atoms of saccharide radicals
    • 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
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07H—SUGARS; DERIVATIVES THEREOF; NUCLEOSIDES; NUCLEOTIDES; NUCLEIC ACIDS
    • C07H1/00—Processes for the preparation of sugar derivatives
    • C07H1/06—Separation; Purification
    • C07H1/08—Separation; Purification from natural products

Landscapes

  • Chemical & Material Sciences (AREA)
  • Life Sciences & Earth Sciences (AREA)
  • Organic Chemistry (AREA)
  • General Health & Medical Sciences (AREA)
  • Health & Medical Sciences (AREA)
  • Engineering & Computer Science (AREA)
  • Biochemistry (AREA)
  • Biotechnology (AREA)
  • Genetics & Genomics (AREA)
  • Molecular Biology (AREA)
  • Dentistry (AREA)
  • Wood Science & Technology (AREA)
  • Zoology (AREA)
  • Environmental Sciences (AREA)
  • Plant Pathology (AREA)
  • Pest Control & Pesticides (AREA)
  • Agronomy & Crop Science (AREA)
  • Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
  • Medicines Containing Plant Substances (AREA)

Abstract

The invention relates to the natural pharmaceutical chemistry field and the technical field of biopesticides, and discloses a new alkaloid compound, a preparation method thereof and application in preparing antimicrobial pesticides. The alkaloid compound has a structure as shown in a drawing of the abstract, and has a chemical name of dihydronarciclasine-4-O-alpha-L-arabinopyranoside. The preparation method is characterized by comprising the following steps: by taking Amaryllidaceae plants as raw materials, extracting by methyl alcohol, ethyl alcohol or water-containing alcohol, filtering, concentrating to a small volume, dispersing by using water, then performing macroporous resin column chromatography, collecting at a part eluted by 30 percent of the ethyl alcohol, and then performing column chromatography repeatedly with column chromatography filler being silica gel or reverse phase silica gel, thus obtaining a new alkaloid. The Amaryllidaceae plants are Zephyranthescandida, Lycorisradiata, Lycorislongituba and Lycorisaurea. As a natural plant bactericide, the compound has remarkable effects of resisting Magnaporthe orythae and Verticillium dahliae, can be singly used, and also can be compounded with other bactericides to be prepared into a compounded bactericidal pesticide.

Description

A kind of alkaloid compound and its production and use
Technical field
The present invention relates to field of natural medicinal chemistry and biological pesticide technical field, disclose a kind of new alkaloid compound and preparation method thereof and the purposes in preparing antibacterial pesticide.
Background technology
21 century, the enhancing along with people's environmental protection consciousness and the concern to food safety, the negative effect of chemical pesticide is increasingly subject to the attention of people, and development biological pesticide becomes the important trend ensureing human health and agricultural sustainable development. Containing abundant secondary metabolite in plant, some secondary metabolites have the effects such as certain prevention and elimination of disease and pests because of it, become the focus of Recent study. The kind of Plant Secondary Metabolites has alkaloids, aldehydes matter, terpenoid, flavonoid, quintessence oil class, light-activated toxin class etc. Wherein alkaloid is the class that content is maximum, and insecticide is not only had the effects such as poisoning, deterrent, refusing to eat, Developing restraint growth by alkaloid, and various plants pathogenic bacteria has very strong antibacterial and bactericidal action simultaneously[1]��
The alkaloids botanical pesticide developed is mostly based on insecticide pesticide, and such as nicotine, matrine etc., in recent years, domestic and international many scholars begin one's study antibacterial, the bactericidal activity of some plant alkaloid extracts. Such as scholars such as Zhang Xiyan, adopt PDA plate growth rate method, determine Cynanchum Komarovii alkaloids extract to rice blast, the inhibitory action of gray mold and virulence. Result shows: two kinds of pathogenic bacterias are all had inhibitory action by extracting solution, and along with the rising of extract concentration, the inhibitory action of pathogenic bacteria mycelial growth are also strengthened therewith; Add the Cynanchum Komarovii extracting solution of adhesive agent without being remarkably reinforced its effect suppressing Growth of Magnaporthe Grisea. The Emulsion that Hunan is prepared with fruit of cubeb litsea tree oil, has good prevention effect to Camellia sinensis Major Diseases congo red rust, tea verticillium wilt, tea moire blight and Fusarium and Verticillium wilts etc. The ground product such as Herba Menthae weigh the consumption of 0.5%��0.1% with soil and process the soil of severe infections cotton wilt, to the preventive effect of droop up to 43.9%��74.3%[2]. Also do not have been reported that rice blast fungus (Magnaportheorythae) and verticillium dahliae (Verticilliumdahliae) are had antibacterial, bactericidal action by the alkaloid component of certain concrete structure.
Amaryllidaceae (Amaryllidaceae) plant is famous with its rich and varied alkaloids composition[3], isoquinolone Alkaloid (isocarbostyril) is the compound that one type is special, is mainly distributed in amrallid[4], learn through retrieval, separate and obtain such natural product compound amounts and only have 12 that there is good antitumor, antiviral and antifungal pharmacological action. According to document[5]Report antifungic action: small intestinal encephalitis microsporidian is had resistance, IC by pancratistatin, 7-deoxynarciclasine50Being 0.18 ��M and 0.20 ��M respectively, this concentration is the compound cell toxicant IC to host cell501/8. Also do not have been reported that rice blast fungus and verticillium dahliae are had antibacterial, bactericidal action by amrallid. The strange quinolone alkaloid that we find first from amrallid has well suppression rice blast fungus and verticillium dahliae activity.
Rice blast is global rice disease, is first of the big disease of Oryza sativa L. three, and ten thousand mu of Anhui super hybridization rice in 2014 causes society's extensive concern because of the rice blast underproduction event that has no harvest. Owing to this pathogen is variable, new cause a disease and the generation of drug-resistant populations is easily caused the disease-resistant variety of new selection-breeding respectively and medicament loses value, therefore, the research and development of new rice blast fungus antibacterial and apply in widespread attention. Cotton verticillium wilt is the worldwide disease of serious restriction Cotton Production at present, and its harm is extremely serious, is referred to as " cancer " of Cotton Gossypii, it does not have specific drug. Therefore, bacterium, fertilizer, medicine integrated control supporting technology work indispensable with the selection-breeding of disease-resistant varieties. In sum, the development of strange quinolone alkaloid bactericide is significant to preventing and treating rice blast and cotton verticillium wilt.
The prior art relevant with the present invention has.
[1] Xue Guanghou, Fan Haiyan, Li Hang, Gao Lu, Li Yifu. Alkaloid applied research in botanical pesticide. North gardening, 2009,6:131-134.
[2] Lv Meixiang, once peace, Wang Xiaojuan, Xie Yan, Wang Hui. The alkaloidal progress of pesticide. Pesticide, 2004,43(6): 249-253.
[3] Li Jian, Yu Miao, Gao Shiyong, Yuan Hongliang, Chen Wenqiang. Alkaloidal pharmacological research in amrallid. Harbin University of Commerce's journal: natural science edition, 2014,30(2): 168-171.
[4] Chen Ning, Dong Yan, Ling Na, Ji Yubin. The structure activity relationship of the typical isoquinolone Alkaloid of Amaryllidaceae two kinds and derivant thereof. Food and medicine, 2014,16(1): 52-54.
[5] Quarzane-AmaraM, FranetichJF, MazierD, etal.InVitroActivitiesofTwoAntimitoticCompounds, Pancratistatinand7-Deoxynarciclasine, againstEncephalitozoonintestinalis, aMicrosporidiumCausingInfectionsinHumans [J] .AntimicrobAgentsChemother, 2001,45 (12): 3409-3415.
Summary of the invention
It is desirable to provide a kind of new alkaloid compound and preparation method thereof and the purposes in preparing antibacterial pesticide.
The invention discloses a kind of alkaloid compound, it is characterised in that: chemistry dihydro Narciclasine-4-O-��-L-arabinose glycosides (dihydronarciclasine-4-O-��-L-arabinopyranoside) by name, molecular weight is 441, and molecular formula is C19H23NO11, structure is shown in Formulas I.
Formulas I.
Above-mentioned alkaloidal preparation method, it is characterized in that: with amrallid for raw material, methanol, ethanol or aqueous alcohols are extracted, filter, be concentrated into small size, through macroporous resin column chromatography after dissipating with moisture, collect 30% alcohol eluting position, then through column chromatography repeatedly, column chromatography filler is silica gel or reverse phase silica gel, obtains new alkaloids.
According to the alkaloidal preparation method of claim 2, it is characterized in that: described amrallid is Herba Alii fistulosi lotus (Zephyranthescandida), Bulbus Lycoridis Radiatae (Lycorisradiata), Bulbus Lycoridis longitubae (Lycorislongituba) and Lycoris aurea (Lycorisaurea).
This alkaloid can extract separation preparation from plant and obtain, it is also possible to obtain by chemosynthesis mode.
A kind of natural plants antibacterial, it is characterised in that using the alkaloid compound of claim 1 as bactericidal component.
Application according to claim 4, it is characterised in that: described crop disease fungal pathogens is rice blast fungus (Magnaportheorythae) and verticillium dahliae (Verticilliumdahliae).
Application according to claim 4, it is characterised in that: described alkaloid compound is bactericide compounded with other, makes compound sterilizing pesticide.
Alkaloid has efficiently, low toxicity, pollution-free, to person poultry safety, model of action is unique, selectivity high, natural enemy and beneficial organism safety and insect pathogen are not likely to produce the natural product of the advantages such as Drug resistance; meet people's requirement to desirable pesticide, but only minority plant alkaloid is used widely in plant protection at present. Narciclasine has the effects such as good antiviral, antitumor, but the effect of rice blast fungus (Magnaportheorythae) and verticillium dahliae (Verticilliumdahliae) is general, dihydro Narciclasine-4-O-��-L-arabinose glycosides connects arabinose artifact activity on mother nucleus structure and is greatly increased, and has the value well used as disinfectant use in agriculture.
For delaying Drug resistance and double worm of curing the disease, weeds to improve pesticide control effect, according to the principle that a medicine is controlled more, the pesticide that compound compound method is made into is adopted to be called Recompounded pesticide according to the mixed proportion that pesticide is certain. In the prevention and control of plant diseases, pest control, single dose is faded out the stage of history gradually, reaches the double effect controlled for increasing preventive effect, and the composite of pesticide is promoted and applies. Dihydro Narciclasine-4-O-��-L-arabinose glycosides, as a kind of new natural biological pesticide, has new Antibacterial Mechanism, and can delay pathogenic bacteria drug resistance after existing agriculture chemical compounding, reduces accidental loss.
Accompanying drawing explanation
Can report as APPENDIX MATERIALSThe using figure below.
Fig. 1, the embodiment of the present invention 1 gained structural formula of compound.
Fig. 2, the embodiment of the present invention 1 gained compound mass spectrum (ESIMS) spectrogram.
Fig. 3, the embodiment of the present invention 1 gained compound proton nmr spectra (1H-NMR) spectrogram.
Fig. 4, the embodiment of the present invention 1 gained compound carbon-13 nmr spectra (13C-NMR) spectrogram.
Fig. 5, the embodiment of the present invention 1 gained compound two dimensional NMR (HSQC) spectrogram.
Fig. 6, the embodiment of the present invention 1 gained compound two dimensional NMR (HMBC) spectrogram.
Fig. 7, the embodiment of the present invention 1 gained compound two dimensional NMR (H-HCOSY) spectrogram.
Detailed description of the invention
In conjunction with detailed description of the invention, the present invention is described in further detail, but present disclosure is not restricted to listed illustrative embodiments.
Embodiment 1.
Fresh Herba Alii fistulosi lotus bulb, chopping, dry and obtain 40kg, extract 3 times with 95% ethanol merceration, each 10 days, being filtrated to get merceration extracting solution, filtering residue extracts 4 times with 95% alcohol heat reflux, 2h/ time, merging the lixiviating solution of merceration and Re Ti, concentrating under reduced pressure obtains extractum, is dissolved in water. Water liquid is through macroporous resin D101 post, and with the ethanol elution of variable concentrations, wherein 30% ethanol position obtains 147g extract. By silicagel column on the 147g extract that obtains, carrying out segmentation and column chromatography repeatedly with chloroform-methanol-water system eluting, obtain compound Yzec-3, purity detects more than 98% through HPLC-MS. After structure is resolved by mass spectrum and nuclear magnetic resonance, NMR, called after dihydro Narciclasine-4-O-��-L-arabinose glycosides (dihydronarciclasine-4-O-��-L-arabinopyranoside), finding after SCIfinder retrieves, this compound is noval chemical compound.
Structure elucidation: compound Yzec-3, white solid, [��]D 26.7+ 18 �� (c0.17, pyridine), is insoluble in chloroform, water, methanol; It is slightly soluble in DMSO, pyridine. TLC meets the aobvious purple of ferric chloride, thus it is speculated that be likely in molecule containing phenolic hydroxyl group; Molish reacting positive, thus it is speculated that sugary in structure; Improvement bismuth potassium iodide is negative. ES-TOF-MS:m/z440.1 [M-H]-, 442.1 [M+H]+, thus it is speculated that the molecular weight of this compound is 441.1; HR-ES-TOF-MS:442.1351 (calc.for [C19H23NO11+H]+442.1349), in conjunction with1H-NMR and13C-NMR, infers that the molecular formula of compound is C19H23NO11, degree of unsaturation is 9.1In H-NMR, �� 6.02 and �� 6.04 (each1H, s ,-OCH2O-) and13In C-NMR, �� 101.9 (-OCH2O-) carbon signal, is the (methylenedioxy) based structures being connected with phenyl ring in amaryllidaceae alkaloid structure. The hydrogen signal of �� 12.82 (1H, s, 7-OH), in conjunction with the character that this compound and ferric chloride develop the color, illustrate structure exists phenolic hydroxyl group, and this phenolic hydroxyl group signal occurs in relatively low field, thus it is speculated that the carbonyl (C-6) being connected with phenyl ring has association. The hydrogen signal of �� 7.10 (1H, s, H-5), fails to find associated carbon signal in hsqc spectrum, thus it is speculated that this hydrogen is likely to be connected with N. �� 6.52 (1H, s, H-10), by hsqc spectrum, is be connected with �� 96.7 (C-10) carbon, it was shown that compound contains 1 unsubstituted fragrance hydrogen. �� 2.94 (1H, dt, J=14.1Hz, 3.2Hz, H-10b), splits a point situation according to peak, illustrates that this hydrogen and a secondary carbon (C-1) and a tertiary carbon (C-4a) are adjacent. In HMBC composes, the hydrogen signal of �� 3.42 (1H, m, H-4a) is relevant with the carbon signal of �� 52.7 (C-4a), infers that the carbon of �� 52.7 (C-4a) is connected with N.
13In C-NMR, there is carbon signal at �� 169.2, illustrate that structure exists carbonyl (C-6).13C-NMR collection of illustrative plates shows, this compound carbon signal in low field has 9, including, the carbon signal of 1 methylene-dioxy and 1 carbonyl carbon signals, carbon signal on 6 phenyl ring, does not contain carbon-carbon double bond except benzene ring structure fragment, possibly together with 1 end group carbon in molecule. It addition, be 9 according to degree of unsaturation in molecular structure, which includes 1 phenyl ring and the (methylenedioxy) based structures being connected with phenyl ring thereof, 1 carbonyl, therefore, structure can only also have 3 rings. Oxygen-containing in molecule more have 11, it should is 1 ketonic oxygen, 2 oxygen of methylene-dioxy, 1 phenolic hydroxyl group, and according to remaining carbon signal displacement, other oxygen belongs to hydroxyl oxygen and sugar hydroxyl.
Middle growing stage and physicochemical property in conjunction with pertinent literature and plant chemical ingredient, thus it is speculated that compound is Amaryllidaceae isoquinolone Alkaloid, and its mother nucleus structure is dihydronarciclasine. In H-HCOSY composes, �� 2.94 (1H, dt, J=14.1Hz, 3.2Hz, and �� 3.42 (1H H-10b), m, H-4a) without coherent signal, and the coupling constant J=3.2Hz of the two hydrogen, speculate that the two hydrogen is in trans position, infer that mother nucleus structure is: trans-dihydronarciclasin.
In hsqc spectrum, the carbon signal of �� 103.5 (C-1 ') and �� 4.23 (1H, J=7.4Hz, H-1 ') hydrogen signal be correlated with, thus it is speculated that be end group carbon signal and the terminal hydrogen signal at bglii fragment position, in conjunction with HMBC compose, learn that in molecular structure of compounds, other carbon signals of bglii fragment are: 72.9 (C-2 '), 75.6 (C-3 '), 69.7 (C-4 '), 66.0 (C-5 '). Speculate containing a pentose. The monosaccharide that hydrolysis generates is arabinose, its optical value infer that it is L-arabinose, by the coupling constant J=7.4Hz of terminal hydrogen, therefore conclude that for being connected to ��-L-arabinose. In HMBC spectrum, the carbon of �� 4.23 (1H, d, J=7.4Hz) hydrogen and �� 79.4 (C-4) is relevant, infers that, in compound Yzec-3 structure, the link position of sugar is on �� 79.4 (C-4) position.
Comprehensive above analysis, Yzec-3 identifies that this compound is: trans-dihydronarciclasine-4-O-��-L-arabinopyranoside. Finding after SCIfinder retrieves, this compound is noval chemical compound.
Embodiment 2.
Bulbus Lycoridis Radiatae bulb extracts 3 times with 80% alcohol heat reflux, 2h/ time, filters united extraction liquid, is concentrated into small size, through macroporous resin AB-8 column chromatography after dissipating with moisture, collects 30% alcohol eluting position, then uses anti-phase C18Silica gel column chromatography, 60% ethanol elution, 3 times repeatedly, to obtain final product. Purity detects more than 90% through HPLC.
Embodiment 3.
Bulbus Lycoridis longitubae bulb extracts 3 times with 75% alcohol heat reflux, 2h/ time, filters united extraction liquid, it is concentrated into small size, through macroporous resin D101 column chromatography after dissipating with moisture, collects 30% alcohol eluting position, recycle silicon plastic column chromatography, chloroform-methanol-water system eluting, then use anti-phase C18Silica gel column chromatography, 60% ethanol elution and get final product. Purity detects more than 85% through HPLC.
Embodiment 4.
Lycoris aurea bulb 80% methanol circumfluence distillation 3 times, 2h/ time, filters united extraction liquid, is concentrated into small size, through macroporous resin D101 column chromatography after dissipating with moisture, collect 30% methanol-eluted fractions position, use anti-phase C18Silica gel column chromatography, 60% methanol-eluted fractions, then use gel LH20Column chromatography, 60% methanol-eluted fractions and get final product. Purity detects more than 90% through HPLC.
Embodiment 5.
Bactericide bacteriostasis circle algoscopy.
(1), for reagent liquid: new alkaloids 10 �� g/mL, Narciclasine 10 �� g/mL.
(2), heating PDA culture medium, add medicinal liquid to be measured when being cooled to about 50 DEG C, blank solvent DMSO is comparison.
(3), rice blast fungus (Magnaportheorythae) and verticillium dahliae (Verticilliumdahliae) were cultivated for two generations continuously, then take the bacterium dish of 5mm diameter at colony edge card punch.
(4), by bacterium dish being inoculated on the flat board of pastille and not pastille respectively, 25 DEG C are cultured to comparison close to covering with plate.
(5), adopt decussation method to measure colony diameter, and calculate suppression ratio.
(6), experimental result.
As shown in Table 2, by the new alkaloids compound of the technology of the present invention production owing to structure increasing arabinose group, the inhibitory activity of rice blast fungus and verticillium dahliae is greatly enhanced. And parent nucleus Narciclasine is general to rice blast fungus and verticillium dahliae effect.
In addition, fusarium graminearum, grape anthracnose, southern corn leaf blight, Botrytis cinerea pathogenic bacteria, rhizoctonia cerealis are also had activity by the new alkaloids compound produced by the technology of the present invention, but be not as rice blast fungus and verticillium dahliae activity is notable as it, so not being described in detail.
A kind of alkaloid compound of the present invention is described already by concrete example for the purposes preparing disinfectant use in agriculture, those skilled in the art can use for reference present invention, the links such as suitable feed change, process conditions realize other purpose corresponding, its relevant change is all without departing from present disclosure, all similar replacements and change will become apparent to those skilled in the art that and be considered as being included within the scope of the present invention.

Claims (6)

1. an alkaloid compound, it is characterised in that: chemistry dihydro Narciclasine-4-O-��-L-arabinose glycosides (dihydronarciclasine-4-O-��-L-arabinopyranoside) by name, molecular weight is 441, and molecular formula is C19H23NO11, structure is shown in Formulas I
��
2. the preparation method of alkaloid compound according to claim 1, it is characterized in that: with amrallid for raw material, methanol, ethanol or aqueous alcohols are extracted, filter, be concentrated into small size, through macroporous resin column chromatography after dissipating with moisture, collect 30% alcohol eluting position, then through column chromatography repeatedly, column chromatography filler is silica gel or reverse phase silica gel, obtains new alkaloids.
3. according to the alkaloidal preparation method of claim 2, it is characterized in that: described amrallid is Herba Alii fistulosi lotus (Zephyranthescandida), Bulbus Lycoridis Radiatae (Lycorisradiata), Bulbus Lycoridis longitubae (Lycorislongituba) and Lycoris aurea (Lycorisaurea).
4. a natural plants antibacterial, it is characterised in that using the alkaloid compound of claim 1 as bactericidal component.
5. application according to claim 4, it is characterised in that: described crop disease fungal pathogens is rice blast fungus (Magnaportheorythae) and verticillium dahliae (Verticilliumdahliae).
6. application according to claim 4, it is characterised in that: described alkaloid compound is bactericide compounded with other, makes compound sterilizing pesticide.
CN201610014222.8A 2016-01-11 2016-01-11 Alkaloid compound and preparation method and application thereof Active CN105622686B (en)

Priority Applications (1)

Application Number Priority Date Filing Date Title
CN201610014222.8A CN105622686B (en) 2016-01-11 2016-01-11 Alkaloid compound and preparation method and application thereof

Applications Claiming Priority (1)

Application Number Priority Date Filing Date Title
CN201610014222.8A CN105622686B (en) 2016-01-11 2016-01-11 Alkaloid compound and preparation method and application thereof

Publications (2)

Publication Number Publication Date
CN105622686A true CN105622686A (en) 2016-06-01
CN105622686B CN105622686B (en) 2021-01-01

Family

ID=56038068

Family Applications (1)

Application Number Title Priority Date Filing Date
CN201610014222.8A Active CN105622686B (en) 2016-01-11 2016-01-11 Alkaloid compound and preparation method and application thereof

Country Status (1)

Country Link
CN (1) CN105622686B (en)

Cited By (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
CN106035417A (en) * 2016-06-29 2016-10-26 安徽省固镇县谷阳有机蔬菜专业合作社 Pesticide for preventing and treating yellow tea mites of capsicum annuum
CN110074145A (en) * 2018-01-26 2019-08-02 南开大学 Application of the Lycoris aurea ethanol extract on pesticide

Citations (3)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
WO1996025415A1 (en) * 1995-02-16 1996-08-22 Virginia Tech Intellectual Properties, Inc. Synthesis of (+)-pancratistatin
CN101805384A (en) * 2010-04-26 2010-08-18 江苏省中国科学院植物研究所 A kind of new short-tube lycoris isoquinolone Alkaloid and its production and use
CN103204860A (en) * 2013-03-11 2013-07-17 华中科技大学 Amaryllidaceae alkaloids compound with neuroprotective effect

Patent Citations (3)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
WO1996025415A1 (en) * 1995-02-16 1996-08-22 Virginia Tech Intellectual Properties, Inc. Synthesis of (+)-pancratistatin
CN101805384A (en) * 2010-04-26 2010-08-18 江苏省中国科学院植物研究所 A kind of new short-tube lycoris isoquinolone Alkaloid and its production and use
CN103204860A (en) * 2013-03-11 2013-07-17 华中科技大学 Amaryllidaceae alkaloids compound with neuroprotective effect

Non-Patent Citations (1)

* Cited by examiner, † Cited by third party
Title
陈宁: ""异喹诺酮生物碱及其衍生物抗肿瘤活性研究进展"", 《广州化工》 *

Cited By (3)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
CN106035417A (en) * 2016-06-29 2016-10-26 安徽省固镇县谷阳有机蔬菜专业合作社 Pesticide for preventing and treating yellow tea mites of capsicum annuum
CN110074145A (en) * 2018-01-26 2019-08-02 南开大学 Application of the Lycoris aurea ethanol extract on pesticide
CN110074145B (en) * 2018-01-26 2022-01-28 南开大学 Application of michelia figo ethanol extract in pesticide

Also Published As

Publication number Publication date
CN105622686B (en) 2021-01-01

Similar Documents

Publication Publication Date Title
Hussain et al. The chemistry and biology of bicoumarins
Javaid et al. Bioassays guided fractionation of Senna occidentalis for identification of natural antifungal constituents against Macrophomina phaseolina
Emam et al. A new furoquinoline alkaloid with antifungal activity from the leaves of Ruta chalepensis L
CN103222486B (en) Plant extract with inhibiting effect on orange pathogenic bacteria as well as preparation method and application thereof
CN105622686A (en) Alkaloid compound and preparation method as well as application thereof
CN109456294A (en) A kind of phenolic compound and application thereof extracted from Radix Glycyrrhizae
CN101223888B (en) Preparing method and application of narrow leaf Chloranthus spicatus extractive
CN101693705B (en) Phenol compound as well as preparation method and applications thereof
CN101857842B (en) Metarhizium GYYA0601 strain capable of producing broad-spectrum antibiotics and application thereof
CN107771866A (en) A kind of crowndaisy chrysanthemum bacteriostatic activity monomer and its application method
CN101744856A (en) Application of jerusalem artichoke extract in preparing anti-tumor medicine or anti-tumor health care product
CN101434581A (en) Preparation of aconite primary diterpene alkaloid component and use in disinsection
CN101219932B (en) Use of bakuchiol for preventing and controlling plant disease
CN111116535A (en) Pseudo-osbeckia chinensis flower extract and application thereof
CN112778262B (en) Plant-derived quassin and preparation method and application thereof
Campos Portela et al. Phytochemistry, Pharmacology and Botanical Aspects of Hortia Species in the Search for Molecules with Bioactive Potential-A Review.
CN1380298A (en) Method for separating and extracting total flavone from goldenrain tree plant and its application
CN110583659A (en) Pesticide composition and preparation method thereof
CN113200903B (en) Pyrrole alkaloid compound with antifeedant and defensive functions on coccinella twenty-eight star in Solanum septemlobum and separation and extraction method thereof
Afrin et al. Antioxidant, thrombolytic, antimicrobial and cytotoxic activities of flavonoids isolated from the root bark of pongamia pinnata
AU2021104334A4 (en) Phenanthroindolizidine alkaloid and preparation method thereof
CN114208855B (en) Botanical bactericidal composition for preventing and treating rice sheath blight disease, preparation and application thereof
CN102050731B (en) Diterpene compound extracted from branches and leaves of croton and use thereof
Cherigo et al. Diversity and allelopathic potential of weeds among Panamanian coffee crops
CN116508787A (en) Urtica thunbergii leaf extract and preparation method and application thereof

Legal Events

Date Code Title Description
C06 Publication
PB01 Publication
SE01 Entry into force of request for substantive examination
SE01 Entry into force of request for substantive examination
GR01 Patent grant
GR01 Patent grant