CN104788416B - A kind of flavonols natural product derivant and application thereof - Google Patents
A kind of flavonols natural product derivant and application thereof Download PDFInfo
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- CN104788416B CN104788416B CN201510124533.5A CN201510124533A CN104788416B CN 104788416 B CN104788416 B CN 104788416B CN 201510124533 A CN201510124533 A CN 201510124533A CN 104788416 B CN104788416 B CN 104788416B
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- 0 CC(C=C(C=C(C12C=C1)O)C(Oc(cc(cc1*)O)c1C1=O)=C1O)=C2OCCN(CCc1ccc(*)cc1)CC(O)=C Chemical compound CC(C=C(C=C(C12C=C1)O)C(Oc(cc(cc1*)O)c1C1=O)=C1O)=C2OCCN(CCc1ccc(*)cc1)CC(O)=C 0.000 description 1
- GSSVZPFRNPJPDW-UHFFFAOYSA-N Cc(cc1)ccc1S(N(CCO)CCOC)(=O)=O Chemical compound Cc(cc1)ccc1S(N(CCO)CCOC)(=O)=O GSSVZPFRNPJPDW-UHFFFAOYSA-N 0.000 description 1
- QHHFGWJKHBSQCD-UHFFFAOYSA-N OCCOc1cc(O)cc(O)c1 Chemical compound OCCOc1cc(O)cc(O)c1 QHHFGWJKHBSQCD-UHFFFAOYSA-N 0.000 description 1
- IKMDFBPHZNJCSN-UHFFFAOYSA-N Oc(cc1O)cc(OC(c(cc2O)cc(O)c2O)=C2O)c1C2=O Chemical compound Oc(cc1O)cc(OC(c(cc2O)cc(O)c2O)=C2O)c1C2=O IKMDFBPHZNJCSN-UHFFFAOYSA-N 0.000 description 1
Classifications
-
- 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
-
- A—HUMAN NECESSITIES
- A01—AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
- A01N—PRESERVATION OF BODIES OF HUMANS OR ANIMALS OR PLANTS OR PARTS THEREOF; BIOCIDES, e.g. AS DISINFECTANTS, AS PESTICIDES OR AS HERBICIDES; PEST REPELLANTS OR ATTRACTANTS; PLANT GROWTH REGULATORS
- A01N43/00—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds
- A01N43/02—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with one or more oxygen or sulfur atoms as the only ring hetero atoms
- A01N43/04—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with one or more oxygen or sulfur atoms as the only ring hetero atoms with one hetero atom
- A01N43/14—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
Abstract
The invention discloses a kind of novel flavonols natural product derivant and its production and use, described novel flavonols natural product derivant is that HTEMY, HTEMY chemical structural formula is as shown in formula I.The present invention is on the premise of ensureing that flavonols natural product basic framework is constant, introduce nitrogenous water soluble group, by unimolecule etherification, flavonols natural product ampelopsin molecule is carried out structure of modification, not only facilitate its water solublity of raising and stability, and improve its anti-phytopathogen activity and antibacterial activity to a certain extent.
Description
Technical field
The present invention relates to a kind of flavonols natural product derivant, particularly to a kind of novel flavonols natural product
Derivant and its production and use.
Background technology
Along with people's raising to health community degree, more and more higher to the health requirements of food and medicine.Moreover, with
The continuous reinforcement of people's environmental protection consciousness, research and development utilize the natural product preventing and treating phytopathogen or thin of environmental protection
Bacterium has been developing progressively one of important subject into numerous scientists.
It is reported, ampelopsin (Myricetin, abridge MY) is as a kind of natural flavone alcohols natural product, safely and effectively,
And have no side effect, various phytopathogens and antibacterial are all had certain antibacterial activity (list of references: Industrial
Crops and Products(2014),59,210-215).But the water solublity of ampelopsin, stability and bioavailability are equal
Poor, significantly limit the range of application of ampelopsin.
Summary of the invention
It is an object of the invention to provide a kind of novel flavonols natural product derivant, have preferably stability and
Water solublity, and there is preferable antibacterial activity and anti-phytopathogen activity.
Present invention also offers the preparation method of novel flavonols natural product derivant, ensureing that flavonols is natural
On the premise of product basic framework is constant, introduce nitrogenous water soluble group, by unimolecule etherification, natural to flavonols
Product ampelopsin molecule carries out structure of modification, not only increases its water solublity, and further increases 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 derivant, described novel flavonols natural product derivant is HTEMY,
HTEMY chemical structural formula is as shown in formula I:
The preparation method of a kind of novel flavonols natural product derivant, is dissolved in ampelopsin in DMF, adds catalyst
K2CO3, it is warming up to 110 DEG C, is then slowly added into dissolved with double [2-(tolysulfonyl epoxide) the ethyl]-para toluene sulfonamide of N, N-
DMF solution, isothermal reaction 3-5h；After reaction terminates, reactant liquor is poured in ethyl acetate, sucking filtration, obtain after concentrating under reduced pressure
Thick product, thick product, through silica gel chromatographic column or half preparation HPLC method purification, is dried, obtains novel flavonols natural product derivant
Product.The purposes of a kind of novel flavonols natural product derivant, HTEMY is applied to prepare novel plant source pesticide.
As preferably, HTEMY is applied to preparation suppression Fructus Solani melongenae disease, Citrullus vulgaris disease, pepper diseases, Fructus Musae disease or Semen Tritici aestivi
The novel plant source pesticide of disease.
As preferably, described Fructus Solani melongenae disease is the disease that Fructus Solani melongenae hyphal cluster germ causes, and described Citrullus vulgaris disease is that Citrullus vulgaris is withered
The disease that pathogenic bacteria causes, described pepper diseases is the disease that Fructus Capsici miliary damping-off pathogenic bacteria causes, and described Fructus Musae disease is that Fructus Musae is withered
The disease that the pathogenic bacteria that withers causes, described wheat diseases is the disease that the compacted spore of Semen Tritici aestivi length causes.
The purposes of a kind of novel flavonols natural product derivant, HTEMY is applied to prepare antimicrobial product.
As preferably, described antimicrobial product is antibacterials, antiseptics for natural food, sterilization shampoo, germicidal toilet soap, kills
One in the spirit of bacterium bath gel, bactericidal liquid detergent, disinfection hand cleanser, sterilizing toilet cleaning, sterilization cleansing milk.
As preferably, the fungicidal spectrum of described antibacterial products includes Bacillus cercus, staphylococcus aureus, hay bud
Spore bacillus, Erwinia carotorora and colon bacillus.
As preferably, when HTEMY is applied to prepare antibacterial products, the concentration of HTEMY controls at >=31.25 μ g/mL.
The invention has the beneficial effects as follows:
1, there is preferably water solublity, and there is preferable antibacterial activity and anti-phytopathogen activity.
2, on the premise of ensureing that flavonols natural product basic framework is constant, introduce nitrogenous water soluble group, pass through
Unimolecule etherification, carries out structure of modification to flavonols natural product ampelopsin molecule, not only increase its water solublity and
Stability, and further increase its anti-phytopathogen activity and antibacterial activity.
3 it has also been found that the HTEMY inhibitory action to antibacterial, so being applied to prepare antimicrobial product.This measure was both
Having widened the range of application of ampelopsin and derivant thereof, the exploitation for antimicrobial product provides new approach again.
4 it has also been found that the HTEMY inhibitory action to fungus, so being applied to prepare novel plant source pesticide.
The range of application of ampelopsin and derivant thereof had both been widened in this measure, and the exploitation for novel plant source pesticide provides new way again
Footpath.
Detailed description of the invention
Below by specific embodiment, technical scheme is described in further detail.
In the present invention, if not refering in particular to, the raw material used and equipment etc. are all commercially available or commonly used in the art.
Method in following embodiment, if no special instructions, is the conventional method of this area.
Raw material ampelopsin (content >=98%) of the present invention by this seminar from natural plants Ampelopsis grossedentata
(Ampelopsis grossedentata) extracts isolated and (sees document: utilize high-speed countercurrent chromatography Simultaneous purification
Dihydromyricetin in Ampelopsis grossedentata and ampelopsin. modern chemical industry (2008), 3,44-46)；Double [the 2-(tolysulfonyl epoxide) of N, N-
Ethyl]-para toluene sulfonamide, CAS 16695-22-0, by diethanolamine and paratoluensulfonyl chloride react generation (see document:
Organic&Biomolecular Chemistry(2007),5,3651-3656)。
Embodiment:
HTEMY building-up process is as follows:
Wherein, Ts represents p-toluenesulfonyl.
Ampelopsin (509mg, 1.6mmol), DMF (15mL), K it is sequentially added in 50ml there-necked flask2CO3(276mg,
2.0mmol), it is warming up to 110 DEG C, is then slowly dropped into dissolved with N, N-double [2-(tolysulfonyl epoxide) ethyl]-to toluene sulphur
The DMF solution (15mL) of amide (454mg, 0.8mmol), (TLC follows the tracks of reaction to constant temperature 110 DEG C reaction 3-5h, and developing solvent is oil
Ether (PE): ethyl acetate (EA): formic acid (HCOOH)=10:10:1, v/v), reactant liquor is poured into ethyl acetate (30-60mL)
In, sucking filtration, obtain thick product after concentrating under reduced pressure, thick product, through silica gel chromatographic column or half preparation HPLC method purification, is dried, is changed
Compound HTEMY (402mg).The advantages such as it is simple that the preparation method of the present invention has synthesis step, low cost, mild condition.
The Structural Identification of product: pale yellow powder.HPLC records going out of novel flavonols natural product derivant HTEMY
Peak time is 28.710min, and purity is 98.32% (peak area A%), UV (MeOH) λmax(log ε): 363.9 (2.56) nm.Choosing
HPLC testing conditions: chromatographic column: Waters XBridgeTMPost (4.6 × 150mm, 5 μm)；Column temperature: 35 DEG C；Flowing phase: second
Nitrile: 0.05% phosphate aqueous solution=0.4:0.6；Flow velocity 1.0mL/min, detects wavelength: 254nm；The wavelength of UV-detector is swept
The scope of retouching is 200-400nm.
Mass spectrum ESI-MS m/z [M-H2O+H]+: 542.54, high resolution mass spectrum HRESIMS (positive) m/z
542.1113[M-H2O+H]+(caled.for C26H24NO10S 542.1115), in conjunction with13C-NMR spectrum can determine that this compound
Molecular formula is C26H25NO11S, degree of unsaturation is 15 Ω.The ν of infrared IRmaxValue and ownership thereof are 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 see table table 1.Wherein,1H-NMR (400MHz, DMSO, δ in ppm, J in Hz),13C-
NMR(100MHz,DMSO)。
HTEMY's1H-NMR spectrum shows 12 peaks, δH12.42 is the proton signal of 5-OH, because it is formed with carbonyl
Hydrogen bond and occur in low field, δH9.68 characteristic signals falling within hydroxyl；In aromatic district, 4 unimodal (s) and 2 occur
Bimodal (d), it is known that the B ring proton of flavonoid drugs is typically in relatively low field, and A ring proton is in high field, therefore understands δH 7.47
Corresponding respectively with 7.31 is the proton signal of H-2' and H-6', is affected by the effect of deshielding of C ring due to H-8 again, shifts to
Low field, therefore δH6.43 and 6.20 corresponding respectively be the proton signal of H-8 and H-2, because 7 " with 9 " are symmetrical, chemical shift
Identical, therefore be can determine that δ by peak area and coupling constantHThe proton signal that 7.38 (2H, d, J=8.0Hz) are shown that 7 ", 9 ",
In like manner δHThe nuclear magnetic signal that 7.63 (2H, d, J=8.0Hz) are 6 ", 10 "；Additionally, δ in hydrogen spectrumH4.41,4.23 and the 8 of 3.44
What individual H represented is 4 methylene, and δHWhat 3 H in 2.36 represented is 1 methyl signals.
13C-NMR spectrum shows 24 carbon signals, wherein δCThe peak height of 129.86 and 126.88 is 2 times of other peaks,
The carbon signal that corresponding should be 7 with symmetrical structure ", 9 " and 6 ", 10 ", removes flavonoid drugs ampelopsin13C-
15 carbon signals (list of references: Food Chemistry (2013), 136 (2), 969-974) of H NMR spectroscopy, also 7 carbon letters
Number, 4 methylene, 1 methyl and 25 ", the 8 " carbon signals of position.
The nuclear magnetic data of table 1 novel flavonols natural product derivant HTEMY
By above HPLC, UV, HRESIMS, IR,1H-NMR and13C-NMR etc. analyze identification of means, finally determine novel
Flavonols natural product derivant HTEMY chemistry is as shown in formula I.
Novel flavonols natural product derivant HTEMY relatively ampelopsin parent has lacked a phenolic hydroxyl group, and many one
The more preferable alcoholic extract hydroxyl group of water solublity and nitrogenous water-soluble structure fragment, contribute to increasing its water solublity.
The reason of ampelopsin less stable is that ampelopsin molecule 4' position hydroxyl is easy to oxidation and goes bad, and mainly shows as
The ampelopsin crystal of yellow is placed in air easily oxidation and turns green.Obtain after 4' position hydroxyl is replaced with nitrogenous water-soluble structure
Novel flavonols natural product derivant HTEMY be placed in the most for a long time in air and still can keep intact, the most permissible
Find out that the stability relatively ampelopsin parent of novel waxberry element derivant has to promote significantly.
The anti-phytopathogen determination of activity of novel flavonols natural product derivant HTEMY
1. for examination strain: banana blight bacteria (F.oxysporum f.sp.cubense race 4)；Fructus Capsici miliary damping-off
Pathogenic bacteria (R.solani (pepper strain) kuhn Schl)；Fructus Solani melongenae hyphal cluster germ (S.sclerotiorum (egg plant
strain)(Lib)De Bary)；The compacted spore of Semen Tritici aestivi length (H.sporium tritici-vulgaris Nishik)；Watermelon blight
Bacterium (F.oxysporum f.sp.Niveum).Above strain is provided by Agricultural University Of South China.
2. test method:
(1) preparation of culture medium and sterilizing
After Rhizoma Solani tuber osi cleans peeling, it is cut into block, weighs about 100g, add 500ml distilled water, after boiling, boil 30min again,
Liquid filtered through gauze will be boiled in beaker, with distilled water filtered juice mended and be re-poured in pot to 500ml, add 20g sucrose, boil
Filtered juice is poured in beaker after sucrose is evenly distributed by boiling；Take the conical flask of 20 100mL, each addition 0.4g agar, add
The above-mentioned filtered juice of 20mL, stoppers stopper, shakes up；121 DEG C of autoclaving 15min are standby.
(2) sample test:
Novel flavonols natural product derivant HTEMY of the 6mg DMSO of 300 μ L dissolves, the doubling dilution of 150 μ L
Method, 5 concentration of general dilution.In 20mL culture medium, the medicinal liquid that 100 μ L prepare, such 5 concentration are added again after preparing concentration
It is respectively 100,50,25,12.5,6.25 μ g/ml.In every bottle of the most parallel culture dish pouring 3 60mm into of culture medium, with punching
Device passes bacterium, and band mycelia faces culture medium, and then back-off culture dish, with water-inlet-proof.Strain is positioned in incubator cultivation, temperature
It is adjusted to 27 DEG C, cultivates 3-5 days.
Measure colony diameter by decussation method and correct, calculating antibacterial percentage rate, and be converted to probability value.Dense with medicament
The logarithm of degree is abscissa X, and the probit value of suppression is vertical coordinate Y, through GraphPad computed in software EC50。
Colony growth diameter (mm)=twice diameter meansigma methods-4.0 (bacterium cake diameter)
3. result of the test: novel flavonols natural product HTEMY to Fructus Capsici miliary damping-off pathogenic bacteria, banana blight bacteria,
Fructus Solani melongenae hyphal cluster germ, the compacted spore of Semen Tritici aestivi length, withered germ of water-melon suppression in concentration EC50Test result be shown in Table 2, positive control is
Thiophanate methyl (Methyl thiophanate).
The anti-phytopathogen activity of table 2 novel flavonols natural product HTEMY
Result shows, novel flavonols natural product derivant HTEMY is to Fructus Capsici miliary damping-off pathogenic bacteria (R.solani
(pepper strain) kuhn Schl), banana blight bacteria (F.oxysporum f.sp.cubense race 4), Fructus Solani melongenae
Hyphal cluster germ (S.sclerotiorum (egg plant strain) (Lib) De Bary), Semen Tritici aestivi length compacted spore (H.sporium
Tritici-vulgaris Nishik), withered germ of water-melon (F.oxysporum f.sp.Niveum) all has in various degree
Inhibitory action, wherein the bacteriostatic activity to Fructus Solani melongenae hyphal cluster germ and withered germ of water-melon is even better than raw material ampelopsin (MY) and sun
Property comparison thiophanate methyl (Methyl thiophanate).The experiment of anti-phytopathogen shows, the natural product of novel flavonols
Thing derivant HTEMY may be used for developing novel plant source pesticide.
The antibacterial activity of novel flavonols natural product derivant HTEMY measures
1. for examination strain: Bacillus cercus (Bacillus cereus), staphylococcus aureus
(Staphyloccocus aureus), bacillus subtilis (Bacillus subtili), Erwinia carotorora (Erwinia
Carotovora), colon bacillus (Escherichia coli).Above strain is provided by Xibei Univ. of Agricultural & Forest Science & Technology.
2. test method:
(1) preparation of culture medium and sterilizing
Hard Carnis Bovis seu Bubali cream culture medium: measure 1000mL deionized water, first toward addition 500mL deionized water in pot, 5g NaCl,
3.0g Carnis Bovis seu Bubali cream (adds in boiled water after cold-water solution), and 10g peptone (is sprinkled into) by several times.Stir to be mixed uniformly after add residue
500mL water, boils addition 20g agar powder, stirs and regulate PH to 7.2, finally culture medium is settled to 1000mL.With each cone
Shape bottle 75mL subpackage, stoppers stopper, shakes up, standby after 121 DEG C of high pressure steam sterilization 15min.
LB culture medium: measure 1000mL deionized water, first adds 500mL, 5g yeast powder in pot, and 10g peptone is (by several times
It is sprinkled into).Stir and remain 500mL water boil rear addition to be mixed, stir and regulate PH to 7.2, finally by culture medium constant volume
To 1000mL.With each conical flask 75mL subpackage, stopper stopper, shake up, standby after 121 DEG C of high pressure steam sterilization 15min.
(2) sample test:
Take a small amount of bacteria suspension under 660nm, measure absorbance, be not added with antibacterial culture fluid as blank, treat bacteria suspension
Ultraviolet absorptivity OD660During for 1.0Abs, carry out next step operation.
Take 5 μ L concentration and be respectively 250,125,62.5,31.25,15.63,7.81,3.91,1.95,0.98,0.49 μ g/mL
Sample solution, and take 10 μ L OD660Bacteria suspension and the 85 μ L fluid mediums (escherichia coli are LB culture medium) of=1.0 all add
Entering in 96 orifice plates (each 96 orifice plate 3 is parallel), mixing concussion is uniformly placed in 37 DEG C of incubators cultivation 8-12h, observation note
Record MIC value.Wherein, sample well A:5 μ L sample+85 μ L fluid medium (escherichia coli are LB culture medium)+10 μ L bacteria suspension；Empty
White hole A0: 5 μ L sample solvent DMSO+95 μ L fluid mediums；Positive controls P:5 μ L ampicillin+85 μ L liquid culture
Base (escherichia coli are LB culture medium)+10 μ L bacteria suspension；Negative control group N:5 μ LDMSO+85 μ L fluid medium (escherichia coli
For LB culture medium)+10 μ L bacteria suspensions, same sample carries out three parallel tests simultaneously.
3. result of the test: novel flavonols natural product HTEMY is to Bacillus cercus, staphylococcus aureus, withered
Grass bacillus cereus, Erwinia carotorora, the minimum inhibitory concentration MIC test result of colon bacillus are shown in Table 3, and positive control is
Ampicillin (Ampicillin).
The antibacterial activity of table 3 novel flavonols natural product HTEMY
As shown in Table 3, novel flavonols natural product HTEMY is to Bacillus cercus, staphylococcus aureus, hay
Bacillus cereus, Erwinia carotorora and escherichia coli have strong inhibitory activity.Being not difficult to find out from MIC value, noval chemical compound HTEMY has
Having the bacteriostatic activity of wide spectrum, its MIC scope is 1.95-31.25 μ g/mL.Relatively finding, noval chemical compound HTEMY antibacterial activity is excellent
In parent ampelopsin (MY), even positive control ampicillin (Ampicillin).Antibacterium test shows, novel flavone
Alcohols natural product HTEMY can be used for preparing antimicrobial product.
Embodiment described above is the one preferably scheme of the present invention, not makees the present invention any pro forma
Limit, on the premise of without departing from the technical scheme described in claim, also have other variant and remodeling.
Claims (2)
1. a flavonols natural product derivant, it is characterised in that: described flavonols natural product derivant is
HTEMY, HTEMY chemical structural formula is as shown in formula I:
2. the purposes of flavonols natural product derivant as claimed in claim 1, it is characterised in that: HTEMY is applied to system
Standby botanical pesticide；HTEMY is applied to preparation suppression Fructus Solani melongenae disease, Citrullus vulgaris disease, pepper diseases, Fructus Musae disease or wheat diseases
Botanical pesticide；Described Fructus Solani melongenae disease is the disease that Fructus Solani melongenae hyphal cluster germ causes, and described Citrullus vulgaris disease is withered germ of water-melon
The disease caused, described pepper diseases is the disease that Fructus Capsici miliary damping-off pathogenic bacteria causes, and described Fructus Musae disease is banana blight
The disease that bacterium causes, described wheat diseases is the disease that the compacted spore of Semen Tritici aestivi length causes.
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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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