CN104788416A - Novel flavonol natural product derivative, preparation method and application thereof - Google Patents
Novel flavonol natural product derivative, preparation method and application thereof Download PDFInfo
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- CN104788416A CN104788416A CN201510124533.5A CN201510124533A CN104788416A CN 104788416 A CN104788416 A CN 104788416A CN 201510124533 A CN201510124533 A CN 201510124533A CN 104788416 A CN104788416 A CN 104788416A
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D311/00—Heterocyclic compounds containing six-membered rings having one oxygen atom as the only hetero atom, condensed with other rings
- C07D311/02—Heterocyclic compounds containing six-membered rings having one oxygen atom as the only hetero atom, condensed with other rings ortho- or peri-condensed with carbocyclic rings or ring systems
- C07D311/04—Benzo[b]pyrans, not hydrogenated in the carbocyclic ring
- C07D311/22—Benzo[b]pyrans, not hydrogenated in the carbocyclic ring with oxygen or sulfur atoms directly attached in position 4
- C07D311/26—Benzo[b]pyrans, not hydrogenated in the carbocyclic ring with oxygen or sulfur atoms directly attached in position 4 with aromatic rings attached in position 2 or 3
- C07D311/28—Benzo[b]pyrans, not hydrogenated in the carbocyclic ring with oxygen or sulfur atoms directly attached in position 4 with aromatic rings attached in position 2 or 3 with aromatic rings attached in position 2 only
- C07D311/30—Benzo[b]pyrans, not hydrogenated in the carbocyclic ring with oxygen or sulfur atoms directly attached in position 4 with aromatic rings attached in position 2 or 3 with aromatic rings attached in position 2 only not hydrogenated in the hetero ring, e.g. flavones
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- A01N—PRESERVATION OF BODIES OF HUMANS OR ANIMALS OR PLANTS OR PARTS THEREOF; BIOCIDES, e.g. AS DISINFECTANTS, AS PESTICIDES OR AS HERBICIDES; PEST REPELLANTS OR ATTRACTANTS; PLANT GROWTH REGULATORS
- A01N43/00—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds
- A01N43/02—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with one or more oxygen or sulfur atoms as the only ring hetero atoms
- A01N43/04—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with one or more oxygen or sulfur atoms as the only ring hetero atoms with one hetero atom
- A01N43/14—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with one or more oxygen or sulfur atoms as the only ring hetero atoms with one hetero atom six-membered rings
- A01N43/16—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with one or more oxygen or sulfur atoms as the only ring hetero atoms with one hetero atom six-membered rings with oxygen as the ring hetero atom
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Abstract
The invention discloses a novel flavonol natural product derivative, a preparation method and application thereof. The novel flavonol natural product derivative is HTEMY, the chemical structural formula of which is as shown in the formula (I). According to the novel flavonol natural product derivative disclosed by the invention, on the premise of ensuring the fundamental framework of the flavonol natural product to be invariable, the flavonol natural product myricetin molecule is structurally modified by introducing nitrogenous water soluble groups and playing the single-molecule etherification role, so that the water solubility and the stability of the novel flavonol natural product derivative can be improved, and the anti-phytopathogen activity and the anti-bacterial activity can be improved to a certain extent.
Description
Technical field
The present invention relates to a kind of flavonols natural product derivative, particularly one novel flavonols natural product derivative and its production and use.
Background technology
Along with people are to the raising of health community degree, also more and more higher to the health requirements of food and medicine.Moreover, along with the continuous reinforcement of people's environmental protection consciousness, research and development utilize the natural product of environmental protection to prevent and treat phytopathogen or bacterium develops into one of important subject of numerous scientific worker gradually.
It is reported, ampelopsin (Myricetin, abbreviation MY) as a kind of natural flavone alcohols natural product, safe and effective, and have no side effect, certain anti-microbial activity (reference: Industrial Crops and Products (2014), 59,210-215) is all had to various phytopathogen and bacterium.But water-soluble, the stability of ampelopsin and bioavailability all poor, significantly limit the range of application of ampelopsin.
Summary of the invention
The object of the present invention is to provide a kind of novel flavonols natural product derivative, there is stability and water-soluble preferably, and there is good antibacterial activity and anti-phytopathogen is active.
Present invention also offers the preparation method of novel flavonols natural product derivative, ensureing under the prerequisite that flavonols natural product basic framework is constant, introduce nitrogenous water soluble group, by unit molecule etherification, structure of modification is carried out to flavonols natural product ampelopsin molecule, not only increase it water-soluble, and further increase its anti-phytopathogen activity and antibacterial activity.
The technical solution adopted for the present invention to solve the technical problems is:
A kind of novel flavonols natural product derivative, described novel flavonols natural product derivative be HTEMY, HTEMY chemical structural formula as shown in formula I:
A preparation method for novel flavonols natural product derivative, is dissolved in ampelopsin in DMF, adds catalyzer K
2cO
3, be warming up to 110 DEG C, then slowly add and be dissolved with N, the DMF solution of two [2-(tolysulfonyl oxygen base) the ethyl]-para toluene sulfonamide of N-, isothermal reaction 3-5h; After reaction terminates, poured into by reaction solution in ethyl acetate, suction filtration, obtain thick product after concentrating under reduced pressure, thick product is through silica gel chromatographic column or half preparative HPLC method purifying, dry, obtains novel flavonols natural product derivative product.A purposes for novel flavonols natural product derivative, HTEMY is applied to and prepares novel plant source pesticide.
As preferably, HTEMY is applied to the novel plant source pesticide that preparation suppresses eggplant disease, watermelon disease, pepper diseases, banana disease or wheat diseases.
As preferably, described eggplant disease is the disease that eggplant hyphal cluster germ causes, described watermelon disease is the disease that withered germ of water-melon causes, described pepper diseases is the disease that capsicum miliary damping-off germ causes, described banana disease is the disease that banana blight bacteria causes, and described wheat diseases is the disease that the long compacted spore of wheat causes.
A purposes for novel flavonols natural product derivative, HTEMY is applied to and prepares antimicrobial product.As preferably, described antimicrobial product is the one in antibacterials, antiseptics for natural food, sterilization shampoo, germicidal toilet soap, sterilization shower cream, bactericidal liquid detergent, disinfection hand cleanser, sterilizing toilet cleaning spirit, sterilization cleansing milk.
As preferably, the fungicidal spectrum of described antibacterial products comprises bacillus cereus, streptococcus aureus, subtilis, Erwinia carotorora and colon bacillus.
As preferably, when HTEMY is applied to and prepares antibacterial products, the concentration of HTEMY controls at >=31.25 μ g/mL.
The invention has the beneficial effects as follows:
1, have water-soluble preferably, and there is good antibacterial activity and anti-phytopathogen activity.
2, ensureing under the prerequisite that flavonols natural product basic framework is constant, introduce nitrogenous water soluble group, by unit molecule etherification, structure of modification is carried out to flavonols natural product ampelopsin molecule, not only increase its water-soluble and stability, and further increase its anti-phytopathogen activity and antibacterial activity.
3, the present invention also finds the restraining effect of HTEMY to bacterium, so be applied to prepare antimicrobial product.The range of application of ampelopsin and derivative thereof had both been widened in this measure, again for the exploitation of antimicrobial product provides new approach.
4, the present invention also finds the restraining effect of HTEMY to fungi, so be applied to prepare novel plant source pesticide.The range of application of ampelopsin and derivative thereof had both been widened in this measure, again for the exploitation of novel plant source pesticide provides new approach.
Embodiment
Below by specific embodiment, technical scheme of the present invention is described in further detail.
In the present invention, if not refer in particular to, the raw material adopted and equipment etc. all can be buied from market or this area is conventional.Method in following embodiment, if no special instructions, is the ordinary method of this area.
Raw material ampelopsin (content >=98%) of the present invention by this seminar extraction and isolation from natural phant Ampelopsis grossedentata (Ampelopsis grossedentata) obtain (see document: utilize the dibydro myricetrin in high-speed countercurrent chromatography Simultaneous purification vine tea and ampelopsin. modern chemical industry (2008), 3,44-46); N, two [2-(tolysulfonyl oxygen base) the ethyl]-para toluene sulfonamide of N-, CAS 16695-22-0, reacted by diethanolamine and Tosyl chloride and generate (see document: Organic & BiomolecularChemistry (2007), 5,3651-3656).
Embodiment:
HTEMY building-up process is as follows:
Wherein, Ts represents p-toluenesulfonyl.
Ampelopsin (509mg, 1.6mmol), DMF (15mL), K is added successively in 50ml there-necked flask
2cO
3(276mg, 2.0mmol), be warming up to 110 DEG C, then slowly instillation is dissolved with N, two [2-(the tolysulfonyl oxygen base) ethyl]-para toluene sulfonamide (454mg of N-, DMF solution (15mL) 0.8mmol), (TLC follows the tracks of reaction to constant temperature 110 DEG C reaction 3-5h, developping agent is sherwood oil (PE): ethyl acetate (EA): formic acid (HCOOH)=10:10:1, v/v), reaction solution is poured in ethyl acetate (30-60mL), suction filtration, thick product is obtained after concentrating under reduced pressure, thick product is through silica gel chromatographic column or half preparative HPLC method purifying, dry, obtain compound H TEMY (402mg).It is simple that preparation method of the present invention has synthesis step, the advantages such as cost is low, mild condition.
The Structural Identification of product: pale yellow powder.The appearance time that HPLC records novel flavonols natural product derivative HTEMY is 28.710min, and purity is 98.32% (peak area A%), UV (MeOH) λ
max(log ε): 363.9 (2.56) nm.The HPLC testing conditions selected: chromatographic column: Waters XBridge
tMpost (4.6 × 150mm, 5 μm); Column temperature: 35 DEG C; Moving phase: acetonitrile: 0.05% phosphate aqueous solution=0.4:0.6; Flow velocity 1.0mL/min, determined wavelength: 254nm; The wavelength scanning range of UV-detector is 200-400nm.
Mass spectrum ESI-MS m/z [M-H
2o+H]
+: 542.54, high resolution mass spectrum HRESIMS (positive) m/z 542.1113 [M-H
2o+H]
+(caled.for C
26h
24nO
10s 542.1115), in conjunction with
13c-NMR spectrum can determine that the molecular formula of this compound is C
26h
25nO
11s, degree of unsaturation is 15 Ω.The ν of infrared IR
maxbe worth and belong to as follows: 3397.2cm
-1(OH), 1656.8cm
-1(C=O), 1160.1,1146.5cm
-1(C-O-C), 1384.6,1320.7,1202.4,1084.3cm
-1(S=O), 1599.7,1497.5,952.2,806.7,715.6,546.4cm
-1(Ar).
The nuclear magnetic data of HTEMY sees the following form table 1.Wherein,
1h-NMR (400MHz, DMSO, δ inppm, J in Hz),
13c-NMR (100MHz, DMSO).
HTEMY's
112 peaks are shown, δ in H-NMR spectrum
h12.42 is the proton signal of 5-OH, because itself and carbonyl form hydrogen bond and appear at low field, δ
h9.68 characteristic signals also belonging to hydroxyl; In aromatic district, occur 4 unimodal (s) and 2 bimodal (d), the B ring proton of known flavonoid drugs is generally in lower field, and A ring proton is in high field, therefore known δ
h7.47 and 7.31 corresponding be respectively the proton signal of H-2' and H-6', again because H-8 is subject to the impact of the C ring effect of deshielding, shift to low field, therefore δ
h6.43 and 6.20 corresponding be respectively the proton signal of H-8 and H-2, because 7 " with 9 " were symmetrical, chemical shift is identical, therefore can judge δ by peak area and coupling constant
hthe proton signal that what 7.38 (2H, d, J=8.0Hz) showed is 7 ", 9 ", in like manner δ
hthe nuclear magnetic signal that 7.63 (2H, d, J=8.0Hz) are 6 ", 10 "; In addition, δ in hydrogen spectrum
h8 H representative of 4.41,4.23 and 3.44 be 4 methylene radical, and δ
hwhat 3 H in 2.36 represented is 1 methyl signals.
1324 carbon signals, wherein δ are shown in C-NMR spectrum
cthe carbon signal that the peak height of 129.86 and 126.88 is 2 times of other peaks, and corresponding should be 7 with symmetrical structure ", 9 " and 6 ", 10 ", removing flavonoid drugs ampelopsin
1315 carbon signals (reference: FoodChemistry (2013), 136 (2), 969-974) of C-NMR spectrum, also have 7 carbon signals, 4 methylene radical, 1 methyl and 25 ", the 8 " carbon signals of position.
The nuclear magnetic data of table 1 novel flavonols natural product derivative HTEMY
By above HPLC, UV, HRESIMS, IR,
1h-NMR and
13c-NMR etc. analyze identification of means, finally determine that novel flavonols natural product derivative HTEMY chemistry is as shown in formula I.
Novel flavonols natural product derivative HTEMY comparatively ampelopsin parent has lacked a phenolic hydroxyl group, and many a water-soluble better alcoholic extract hydroxyl group and nitrogenous water-soluble structure fragment, contributes to increasing that it is water-soluble.
The reason of ampelopsin less stable is that ampelopsin molecule 4' position hydroxyl is easy to oxidation and go bad, and main manifestations is that the ampelopsin crystal of yellow is placed in air and is very easily oxidized and turns green.The novel flavonols natural product derivative HTEMY obtained after being replaced with nitrogenous water-soluble structure by 4' position hydroxyl is placed in air equally for a long time and still can keeps intact, and the stability that this shows novel waxberry element derivative comparatively ampelopsin parent has and promotes significantly.
The anti-phytopathogen determination of activity of novel flavonols natural product derivative HTEMY
1. for examination bacterial classification: banana blight bacteria (F.oxysporum f.sp.cubense race 4); Capsicum miliary damping-off germ (R.solani (pepper strain) kuhn Schl); Eggplant hyphal cluster germ (S.sclerotiorum (egg plant strain) (Lib) De Bary); The long compacted spore (H.sporiumtritici-vulgaris Nishik) of wheat; Withered germ of water-melon (F.oxysporum f.sp.Niveum).Above bacterial classification is provided by Agricultural University Of South China.
2. test method:
(1) preparation of substratum and sterilizing
After potato cleans peeling, be cut into block, take about 100g, add 500ml distilled water, boil 30min again after boiling, liquid filtered through gauze will be boiled in beaker, with distilled water, filtered juice benefit is again poured in pot to 500ml, add 20g sucrose, boil and after sucrose is evenly distributed, filtered juice is poured in beaker; Get the Erlenmeyer flask of 20 100mL, respectively add 0.4g agar, then add the above-mentioned filtered juice of 20mL, jam-pack stopper, shakes up; 121 DEG C of autoclaving 15min are for subsequent use.
(2) sample test:
The novel flavonols natural product derivative HTEMY of 6mg dissolves with the DMSO of 300 μ L, the doubling dilution of 150 μ L, general dilution 5 concentration.In 20mL substratum, add the liquid that 100 μ L prepare after preparing concentration again, 5 concentration like this are respectively 100,50,25,12.5,6.25 μ g/ml.Every bottle of substratum is parallel while hot to be poured in the culture dish of 3 60mm, passes bacterium with punch tool, and band mycelia faces substratum, and then back-off culture dish, with water-inlet-proof.Be positioned in incubator by bacterial classification and cultivate, temperature is adjusted to 27 DEG C, cultivates 3-5 days.
Measure colony diameter by right-angled intersection method and correct, calculating antibacterial percentage, and be converted to probability value.With the logarithm of drug concentration for X-coordinate X, the probit value of suppression is ordinate zou Y, through GraphPad computed in software EC
50.
Colony growth diameter (mm)=twice diameter mean value-4.0 (bacterium cake diameter)
3. test-results: novel flavonols natural product HTEMY is to concentration EC in the suppression of capsicum miliary damping-off germ, banana blight bacteria, eggplant hyphal cluster germ, the long compacted spore of wheat, withered germ of water-melon
50test result in table 2, positive control is thiophanate methyl (Methyl thiophanate).
The anti-phytopathogen of table 2 novel flavonols natural product HTEMY is active
Result shows, novel flavonols natural product derivative HTEMY is to capsicum miliary damping-off germ (R.solani (pepper strain) kuhn Schl), banana blight bacteria (F.oxysporumf.sp.cubense race 4), eggplant hyphal cluster germ (S.sclerotiorum (egg plant strain) (Lib) DeBary), the long compacted spore (H.sporium tritici-vulgaris Nishik) of wheat, withered germ of water-melon (F.oxysporum f.sp.Niveum) all has restraining effect in various degree, wherein raw material ampelopsin (MY) and positive control thiophanate methyl (Methyl thiophanate) are even better than to the bacteriostatic activity of eggplant hyphal cluster germ and withered germ of water-melon.Anti-phytopathogen experiment shows, novel flavonols natural product derivative HTEMY may be used for development of new botanical pesticide.
The antibacterial activity of novel flavonols natural product derivative HTEMY measures
1. for examination bacterial classification: bacillus cereus (Bacillus cereus), streptococcus aureus (Staphyloccocus aureus), subtilis (Bacillus subtili), Erwinia carotorora (Erwinia carotovora), colon bacillus (Escherichia coli).Above bacterial classification provides by Xibei Univ. of Agricultural & Forest Science & Technology.
2. test method:
(1) preparation of substratum and sterilizing
Hard extractum carnis substratum: measure 1000mL deionized water, first adds 500mL deionized water, 5g NaCl, 3.0g extractum carnis (adding in boiling water after cold-water solution), 10g peptone (gradation is sprinkled into) in pot.Stir to be mixed evenly after add residue 500mL water, boil and add 20g agar powder, stir and regulate PH to 7.2, finally substratum being settled to 1000mL.With each Erlenmeyer flask 75mL packing, jam-pack stopper, shakes up, for subsequent use after 121 DEG C of high pressure steam sterilization 15min.
LB substratum: measure 1000mL deionized water, first adds 500mL, 5g yeast powder, 10g peptone (gradation is sprinkled into) in pot.Stir to be mixed evenly after add residue 500mL water boil, stir and regulate PH to 7.2, finally substratum being settled to 1000mL.With each Erlenmeyer flask 75mL packing, jam-pack stopper, shakes up, for subsequent use after 121 DEG C of high pressure steam sterilization 15min.
(2) sample test:
The bacteria suspension that takes a morsel measures absorbancy under 660nm, not add the nutrient solution of bacterium for blank, treats the ultraviolet absorptivity OD of bacteria suspension
660during for 1.0Abs, carry out next step operation.
Get 5 μ L concentration and be respectively 250,125,62.5,31.25,15.63,7.81,3.91,1.95,0.98, the sample solution of 0.49 μ g/mL, and get 10 μ L OD
660the bacteria suspension of=1.0 all adds in 96 orifice plates (each 96 orifice plate 3 is parallel) with 85 μ L liquid nutrient mediums (intestinal bacteria are LB substratum), and mixing concussion is evenly placed in 37 DEG C of incubators cultivates 8-12h, observational data MIC value.Wherein, sample well A:5 μ L sample+85 μ L liquid nutrient medium (intestinal bacteria are LB substratum)+10 μ L bacteria suspension; Blank well A
0: 5 μ L sample solvent DMSO+95 μ L liquid nutrient mediums; Positive controls P:5 μ L penbritin+85 μ L liquid nutrient medium (intestinal bacteria are LB substratum)+10 μ L bacteria suspension; Negative control group N:5 μ LDMSO+85 μ L liquid nutrient medium (intestinal bacteria are LB substratum)+10 μ L bacteria suspension, same sample carries out three parallel tests simultaneously.
3. test-results: novel flavonols natural product HTEMY is to the minimum inhibitory concentration MIC test result of bacillus cereus, streptococcus aureus, subtilis, Erwinia carotorora, colon bacillus in table 3, and positive control is penbritin (Ampicillin).
The antibacterial activity of table 3 novel flavonols natural product HTEMY
As shown in Table 3, novel flavonols natural product HTEMY has strong inhibitory activity to bacillus cereus, streptococcus aureus, subtilis, Erwinia carotorora and intestinal bacteria.Be not difficult to find out from MIC value, new compound HTEMY has the bacteriostatic activity of wide spectrum, and its MIC scope is 1.95-31.25 μ g/mL.Relatively find, new compound HTEMY anti-microbial activity is better than parent ampelopsin (MY), or even positive control penbritin (Ampicillin).Antibacterium test shows, novel flavonols natural product HTEMY can for the preparation of antimicrobial product.
Above-described embodiment is one of the present invention preferably scheme, not does any pro forma restriction to the present invention, also has other variant and remodeling under the prerequisite not exceeding the technical scheme described in claim.
Claims (9)
1. a novel flavonols natural product derivative, is characterized in that: described novel flavonols natural product derivative be HTEMY, HTEMY chemical structural formula as shown in formula I:
2. the preparation method of novel flavonols natural product derivative as claimed in claim 1, is characterized in that: be dissolved in by ampelopsin in DMF, adds catalyzer K
2cO
3, be warming up to 110 DEG C, then slowly add and be dissolved with N, the DMF solution of two [2-(tolysulfonyl oxygen base) the ethyl]-para toluene sulfonamide of N-, isothermal reaction 3-5h; After reaction terminates, poured into by reaction solution in ethyl acetate, suction filtration, obtain thick product after concentrating under reduced pressure, thick product is through silica gel chromatographic column or half preparative HPLC method purifying, dry, obtains novel flavonols natural product derivative product.
3. the purposes of novel flavonols natural product derivative as claimed in claim 1, is characterized in that: HTEMY is applied to and prepares novel plant source pesticide.
4. purposes according to claim 3, is characterized in that: HTEMY is applied to the novel plant source pesticide that preparation suppresses eggplant disease, watermelon disease, pepper diseases, banana disease or wheat diseases.
5. purposes according to claim 4, it is characterized in that: described eggplant disease is the disease that eggplant hyphal cluster germ causes, described watermelon disease is the disease that withered germ of water-melon causes, described pepper diseases is the disease that capsicum miliary damping-off germ causes, described banana disease is the disease that banana blight bacteria causes, and described wheat diseases is the disease that the long compacted spore of wheat causes.
6. the purposes of novel flavonols natural product derivative as claimed in claim 1, is characterized in that: HTEMY is applied to and prepares antimicrobial product.
7. purposes according to claim 6, is characterized in that: described antimicrobial product is the one in antibacterials, antiseptics for natural food, sterilization shampoo, germicidal toilet soap, sterilization shower cream, bactericidal liquid detergent, disinfection hand cleanser, sterilizing toilet cleaning spirit, sterilization cleansing milk.
8. purposes according to claim 6, is characterized in that: the fungicidal spectrum of described antibacterial products comprises bacillus cereus, streptococcus aureus, subtilis, Erwinia carotorora and colon bacillus.
9. purposes according to claim 6, is characterized in that: when HTEMY is applied to and prepares antibacterial products, and the concentration of HTEMY controls at >=31.25 μ g/mL.
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| Publication number | Priority date | Publication date | Assignee | Title |
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| CN110029117A (en) * | 2019-04-04 | 2019-07-19 | 中国热带农业科学院南亚热带作物研究所 | Flavonol synthase gene SmFLS and its application and flavonols synzyme |
| CN110183430A (en) * | 2019-06-18 | 2019-08-30 | 贵州大学 | 4-(N- methyl containing sulfonamide) amino piperidine myricetin derivative, Preparation method and use |
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| Publication number | Priority date | Publication date | Assignee | Title |
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| CN101250175A (en) * | 2008-04-01 | 2008-08-27 | 赫玉芳 | Preparation of myricetin, medicinal preparation and new medical usage |
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| KR20100070693A (en) * | 2008-12-18 | 2010-06-28 | 건국대학교 산학협력단 | THE USE OF 3,3',4',5,5',7-HEXA -HYDROXYFLAVONE(MYRICETIN) AS INHIBITORS OF β-KETOACYL ACYL CARRIER PROTEIN SYNTHASE III (KAS III) |
| CN102875620B (en) * | 2012-10-16 | 2015-02-04 | 昆明龙津药业股份有限公司 | New derivatives of myricetin and application of derivatives to medicine preparation |
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| CN101250175A (en) * | 2008-04-01 | 2008-08-27 | 赫玉芳 | Preparation of myricetin, medicinal preparation and new medical usage |
Cited By (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN110029117A (en) * | 2019-04-04 | 2019-07-19 | 中国热带农业科学院南亚热带作物研究所 | Flavonol synthase gene SmFLS and its application and flavonols synzyme |
| CN110029117B (en) * | 2019-04-04 | 2022-11-01 | 怀化学院 | Flavonol synthetase gene SmFLS and application thereof, and flavonol synthetase |
| CN110183430A (en) * | 2019-06-18 | 2019-08-30 | 贵州大学 | 4-(N- methyl containing sulfonamide) amino piperidine myricetin derivative, Preparation method and use |
| CN110183430B (en) * | 2019-06-18 | 2020-06-05 | 贵州大学 | 4- (N-methyl) aminopiperidine myricetin derivative containing sulfamide, preparation method and application |
| WO2020253152A1 (en) * | 2019-06-18 | 2020-12-24 | 贵州大学 | Sulfonamide-containing 4-(n-methyl)aminopiperidine myricetin derivative, preparation method and application |
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| CN105968078B (en) | 2018-03-09 |
| CN104788416B (en) | 2017-01-04 |
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