CN106632545B - (Z, E) 5-OH-3- (phenyl derivatives-methine)-flavanone -7-O- glucosides and its preparation and its application - Google Patents
(Z, E) 5-OH-3- (phenyl derivatives-methine)-flavanone -7-O- glucosides and its preparation and its application Download PDFInfo
- Publication number
- CN106632545B CN106632545B CN201610821025.7A CN201610821025A CN106632545B CN 106632545 B CN106632545 B CN 106632545B CN 201610821025 A CN201610821025 A CN 201610821025A CN 106632545 B CN106632545 B CN 106632545B
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- China
- Prior art keywords
- acid
- flavanone
- glucosides
- group
- methine
- Prior art date
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- 238000002360 preparation method Methods 0.000 title claims abstract description 28
- 229930182478 glucoside Natural products 0.000 title claims abstract description 25
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- -1 methylene-dioxy Chemical group 0.000 claims abstract description 41
- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 claims abstract description 20
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- 229940079593 drug Drugs 0.000 claims abstract description 9
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- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims abstract description 4
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- 125000002791 glucosyl group Chemical group C1([C@H](O)[C@@H](O)[C@H](O)[C@H](O1)CO)* 0.000 claims abstract description 3
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- SBHXYTNGIZCORC-ZDUSSCGKSA-N eriodictyol Chemical compound C1([C@@H]2CC(=O)C3=C(O)C=C(C=C3O2)O)=CC=C(O)C(O)=C1 SBHXYTNGIZCORC-ZDUSSCGKSA-N 0.000 description 1
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- 150000002213 flavones Chemical class 0.000 description 1
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- 229910052736 halogen Inorganic materials 0.000 description 1
- 150000002367 halogens Chemical class 0.000 description 1
- QUQPHWDTPGMPEX-QJBIFVCTSA-N hesperidin Chemical compound C1=C(O)C(OC)=CC=C1[C@H]1OC2=CC(O[C@H]3[C@@H]([C@@H](O)[C@H](O)[C@@H](CO[C@H]4[C@@H]([C@H](O)[C@@H](O)[C@H](C)O4)O)O3)O)=CC(O)=C2C(=O)C1 QUQPHWDTPGMPEX-QJBIFVCTSA-N 0.000 description 1
- 239000001257 hydrogen Substances 0.000 description 1
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- 230000002401 inhibitory effect Effects 0.000 description 1
- 150000007529 inorganic bases Chemical class 0.000 description 1
- 229910000359 iron(II) sulfate Inorganic materials 0.000 description 1
- 230000031700 light absorption Effects 0.000 description 1
- 238000004519 manufacturing process Methods 0.000 description 1
- 238000001819 mass spectrum Methods 0.000 description 1
- OGXRXFRHDCIXDS-UHFFFAOYSA-N methanol;propane-1,2,3-triol Chemical compound OC.OCC(O)CO OGXRXFRHDCIXDS-UHFFFAOYSA-N 0.000 description 1
- UZKWTJUDCOPSNM-UHFFFAOYSA-N methoxybenzene Substances CCCCOC=C UZKWTJUDCOPSNM-UHFFFAOYSA-N 0.000 description 1
- STZCRXQWRGQSJD-GEEYTBSJSA-M methyl orange Chemical compound [Na+].C1=CC(N(C)C)=CC=C1\N=N\C1=CC=C(S([O-])(=O)=O)C=C1 STZCRXQWRGQSJD-GEEYTBSJSA-M 0.000 description 1
- 229940012189 methyl orange Drugs 0.000 description 1
- RDOXTESZEPMUJZ-UHFFFAOYSA-N methyl phenyl ether Natural products COC1=CC=CC=C1 RDOXTESZEPMUJZ-UHFFFAOYSA-N 0.000 description 1
- 239000011259 mixed solution Substances 0.000 description 1
- 230000004048 modification Effects 0.000 description 1
- 238000012986 modification Methods 0.000 description 1
- SYSQUGFVNFXIIT-UHFFFAOYSA-N n-[4-(1,3-benzoxazol-2-yl)phenyl]-4-nitrobenzenesulfonamide Chemical class C1=CC([N+](=O)[O-])=CC=C1S(=O)(=O)NC1=CC=C(C=2OC3=CC=CC=C3N=2)C=C1 SYSQUGFVNFXIIT-UHFFFAOYSA-N 0.000 description 1
- CMWTZPSULFXXJA-VIFPVBQESA-N naproxen Chemical compound C1=C([C@H](C)C(O)=O)C=CC2=CC(OC)=CC=C21 CMWTZPSULFXXJA-VIFPVBQESA-N 0.000 description 1
- 229960002009 naproxen Drugs 0.000 description 1
- 150000002926 oxygen Chemical class 0.000 description 1
- 239000001301 oxygen Substances 0.000 description 1
- 229910052760 oxygen Inorganic materials 0.000 description 1
- QNGNSVIICDLXHT-UHFFFAOYSA-N para-ethylbenzaldehyde Natural products CCC1=CC=C(C=O)C=C1 QNGNSVIICDLXHT-UHFFFAOYSA-N 0.000 description 1
- 239000008194 pharmaceutical composition Substances 0.000 description 1
- 239000002574 poison Substances 0.000 description 1
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- 125000000168 pyrrolyl group Chemical group 0.000 description 1
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- 230000003252 repetitive effect Effects 0.000 description 1
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- 230000007017 scission Effects 0.000 description 1
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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
- C07H17/04—Heterocyclic radicals containing only oxygen as ring hetero atoms
- C07H17/06—Benzopyran radicals
- C07H17/065—Benzo[b]pyrans
- C07H17/07—Benzo[b]pyran-4-ones
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K8/00—Cosmetics or similar toiletry preparations
- A61K8/18—Cosmetics or similar toiletry preparations characterised by the composition
- A61K8/30—Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds
- A61K8/60—Sugars; Derivatives thereof
- A61K8/602—Glycosides, e.g. rutin
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61Q—SPECIFIC USE OF COSMETICS OR SIMILAR TOILETRY PREPARATIONS
- A61Q19/00—Preparations for care of the skin
- A61Q19/08—Anti-ageing preparations
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07H—SUGARS; DERIVATIVES THEREOF; NUCLEOSIDES; NUCLEOTIDES; NUCLEIC ACIDS
- C07H1/00—Processes for the preparation of sugar derivatives
-
- A—HUMAN NECESSITIES
- A23—FOODS OR FOODSTUFFS; TREATMENT THEREOF, NOT COVERED BY OTHER CLASSES
- A23V—INDEXING SCHEME RELATING TO FOODS, FOODSTUFFS OR NON-ALCOHOLIC BEVERAGES AND LACTIC OR PROPIONIC ACID BACTERIA USED IN FOODSTUFFS OR FOOD PREPARATION
- A23V2002/00—Food compositions, function of food ingredients or processes for food or foodstuffs
Landscapes
- Health & Medical Sciences (AREA)
- Chemical & Material Sciences (AREA)
- Life Sciences & Earth Sciences (AREA)
- Organic Chemistry (AREA)
- General Health & Medical Sciences (AREA)
- Biochemistry (AREA)
- Biotechnology (AREA)
- Genetics & Genomics (AREA)
- Molecular Biology (AREA)
- Public Health (AREA)
- Engineering & Computer Science (AREA)
- Veterinary Medicine (AREA)
- Animal Behavior & Ethology (AREA)
- Birds (AREA)
- Epidemiology (AREA)
- Gerontology & Geriatric Medicine (AREA)
- Dermatology (AREA)
- Cosmetics (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Saccharide Compounds (AREA)
Abstract
The present invention provides one kind (Z, E) 5-OH-3-(phenyl derivatives-methine)-flavanone -7-O- glucosides and preparation method and application；(Z, E) -5-OH-3-(phenyl derivatives-methine)-flavanone -7-O- glucosides, general structure is shown in shown in (I),Wherein: R1It can be glucosyl group (- glucose), rue glycosyl (- [[6-O- (6-Deoxy-alpha-L-mannopyranosyl)-beta-D-glucopyranosyl] oxy]), neohesperidose base (- [[2-O- (6-Deoxy-alpha-L-mannopyranosyl)-beta-D-glucopyranosyl] oxy]), glucuronic acid base (7-beta-D-glucopyranose acid)；R2It can be-H ,-OH ,-OCH3；R3It can be-H ,-OH ,-OCH3,-O-glucose ,-O-glucuronic ,-O-neohesperidose ,-F ,-Cl, Dan Jituan or more group in-Br；R4It can be-H ,-OH ,-OCH3,-Cl ,-Br ,-NO2,-COOH, Dan Jituan or more group in methylene-dioxy；With the compound that preferable anti-oxidant, anti-inflammatory, antibacterial, antiviral, anticancer, antibacterial, cardiovascular and cerebrovascular are protected, can be widely used in the industry such as food, cosmetics, drug.
Description
Technical field:
The invention belongs to chemistry, cosmetics and field of medicaments, be related to a kind of flavone compound and preparation method thereof and its
Using especially one kind (Z, E) 5-OH-3- (phenyl derivatives-methine)-flavanone -7-O- glucosides and preparation method thereof
And its application.
Background technique:
Flavone compound is many kinds of in nature, and rich content, extraction and preparation technique is simple, cheap.By
In the secondary metabolite of natural flavone system plant enzyme, contain phenolic hydroxyl group more.Since phenolic hydroxyl group is unevenly distributed, it is divided to and accounts for two benzene
Ring, not formed neighbour diphenol OH, inoxidizability effect is weaker, representative compound as aurantiamarin, aurantiin, neohesperidin,
Ao Siming, Rhoifolin, apiolin, hesperetin, naringenin, hesperidin methyl.Even if containing adjacent two phenolic hydroxyl groups, due to two benzene
Ring has preferable coplanarity, and molecule is easy to arrange layer by layer with molecule, forms crystallization, and water-soluble low, bioavilability is low,
Oxidation resistance is limited.Representative compound has scutelloside, rutin, Breviscapinun, honeysuckle glycosides, baicalein, luteolin.Tea
The mixture of catechin in polyphenol, structure proximate, physicochemical properties are close, and separation is more difficult.And the stronger catechu of activity
Epigallo-catechin gallate (EGCG) (EGCG), L-Epicatechin gallate (ECG) in phenol, because containing ester bond in molecule,
Property is unstable, using being restricted.
Aurantiamarin, aurantiin, neohesperidin, diosmin, Rhoifolin, apiolin, hesperetin, naringenin, methyl orange
The flavone compounds such as skin glycosides, scutelloside, rutin, Breviscapinun, honeysuckle glycosides, baicalein, luteolin, in anti-inflammatory, antioxygen
The power of the effects of change, antibacterial, antiviral and antitumor, expansion cardiovascular and cerebrovascular, depends on water-soluble and scavenging activated oxygen
Ability.Therefore, how its application efficiency in above-mentioned each field is improved.Firstly, introducing big group, increase space bit
The coplanarity of two phenyl ring in toroidal molecule is broken in resistance, and then is increased water-soluble；Secondly, increasing the group and double key number of phenolic hydroxyl group
Inoxidizability can be improved in mesh；Furthermore increases phenolic hydroxyl group and other polar groups, can also propose high molecular polarity, increase water-soluble
Property；Finally, introducing methoxyl group, the small polar group such as chlorine element can delay to be metabolized, and extend action time.
Summary of the invention:
The present invention seeks to provide one kind (Z, E) 5-OH-3- (phenyl derivatives-methine)-flavanone -7-O- glucosides
And preparation method thereof and its application；Be using 5-OH flavanone -7-O- glucosides as raw material, it is anti-by aldol condensation
It answers, introduces biggish group at 3-, break the flatness of toroidal molecule, obtain water-soluble preferable or more phenolic hydroxyl group compound,
Flavone compound water solubility and inoxidizability are improved, the compound high compared with ester bond stability in EGCG, ECG improves and remove oxygen
The ability of free radical or better bioavilability have preferable anti-oxidant, anti-inflammatory, antibacterial with it, antiviral, anticancer, resist
The compound that bacterium, cardiovascular and cerebrovascular are protected can be widely used in the industry such as food, cosmetics, drug.
Inventing the technical solution is,
The present invention (Z, E) 5-OH-3- (phenyl derivatives-methine)-flavanone -7-O- glucosides, general structure is such as
(I) shown in,
Wherein: R1It can be glucosyl group (- glucose), rue glycosyl (- [[6-O- (6-Deoxy-alpha-L-
Mannopyranosyl)-beta-D-glucopyranosyl] oxy]), neohesperidose base (- [[2-O- (6-Deoxy-alpha-
L-mannopyranosyl)-beta-D-glucopyranosyl] oxy]), glucuronic acid base (7-beta-D-
glucopyranose acid)；R2It can be-H ,-OH ,-OCH3；R3It can be-OH ,-OCH3、-O-glucose、-O-
Glucuronic ,-O-neohesperidose ,-F ,-Cl, Dan Jituan or more group in-Br；R4It can be-H ,-OH ,-OCH3,-
Cl、-Br、-NO2,-COOH, Dan Jituan or more group in methylene-dioxy.
The present invention (Z, E) 5-OH-3- (phenyl derivatives-methine)-flavanone -7-O- glucosides preparation method,
It is using 5-OH flavanone -7-O- glucosides as raw material, in polar solvent, using organic base and organic acid as catalyst, with benzene first
Aldehyde derivatives are made by aldol condensation reaction, wherein 5-OH flavanone -7-O- glucosides and benzaldehyde-derivative
The quality molar ratio of object is 3:1-1:3.
The further control reaction temperature is in room temperature to 120 DEG C.
5-OH flavanone -7-O- glucosides of the present invention, structural formula are shown in (II),
Wherein: R1、R2、R3With the R in structure (I)1、R2、R3Group meaning is identical, and representative compound has aurantiamarin
(Cas:520-26-3), aurantiin (CAS:10236-47-2), neohesperidin (CAS:13241-33-3), hesperidin methyl, two
Hydrogen scutelloside, dihydro Breviscapinun, eriodictyol -7-O-glucose, hesperetin -7-O-glucose, naringenin -7-O-
Glucose, dihydro scutellarin, dihydro wogonoside.
Benzaldehyde derivative of the present invention is shown in structure formula (III)
Wherein: R4With the R in structure (I)4Group meaning is identical.
Polar solvent of the present invention is DMSO, DMF, THF, any one or a few in alcohols；The alcohols is
Methanol, ethyl alcohol, propyl alcohol, isopropanol, ethylene glycol, propylene glycol, any one in glycerine.
Organic base of the present invention is dimethylamine, diethylamine, nafoxidine, piperidines, piperazine, any one in morpholine；
It is further preferably nafoxidine.
Organic acid of the present invention is formic acid, acetic acid, propionic acid, butyric acid, valeric acid, caproic acid, benzoic acid, phenylacetic acid, phenylpropyl alcohol
Acid, lactic acid, succinic acid, any one in tartaric acid, further preferably glacial acetic acid.
Present invention one kind (Z, E) 5-OH-3- (phenyl derivatives-methine)-flavanone -7-O- glucosides is applied to anti-
The composition of inflammation, antioxidant food, cosmetic composition and antibacterial, antitumor, cardiovascular and cerebrovascular protection drug.
(Z, E) -5-OH-3- (phenyl derivatives-methine)-flavanone -7-O- glucosides of the present invention is one kind
Pharmaceutical composition.
Reaction condition of the present invention is mild, can carry out in alcohol, THF, DMSO, DMF, aldol condensation reacting part
Position is single, and product is easy to purify, and entire preparation process is simple, is conducive to industrialized production.
Compound of the present invention, water solubility, alcohol-soluble, it is anti-oxidant can increase, in antibacterial, anti-inflammatory, anti-oxidant, disease-resistant
Protection, more original flavones such as poison, cardiovascular and cerebrovascular protection have innate advantage, are easier to be prepared into suitable preparation, make it have
Food, drug, cosmetic field are further applied, there is potential potential applicability in clinical practice and potential economic benefit and society
Benefit.
If containing halogen in benzaldehyde derivative, lipophilicity is favorably improved, is enhanced into maincenter ability, is sent out in cental system
The effect of waving will also increase；If benzaldehyde derivative contains-COOH ,-CH2-N(CH3)2、-SO3H、-OSO3Polarity can be improved in H,
And corresponding salt is prepared by acid or alkali, further increases water solubility；If-the NH on benzaldehyde2,-OH it is previously prepared at
Acylate contains these acyl group groups in condensation product, can delay accretion rate, be conducive to the increasing action time.
The principle of the present invention:
It should be pointed out that theoretically generate trans- (E), but due in flavanone molecule 2- be phenyl or phenyl
Derivative, 4- are pyrrole group, and group is larger, are introduced when at flavanone 3- compared with macoradical, the spy of steric hindrance
It is unobvious, cause new bonding to be difficult to rotate freely, generate two kinds of midbody products, reaction molecular formula is as follows:
Two kinds of midbody product dehydrations are also formed along anti-two kinds of isomers, and reaction equation is as follows:
Since glucosides polarity is larger, it is not easy to separate above two compound using silicagel column；It is last it may be noted that
Aldehyde radical electropositive it is higher, easier participation reaction；When with inorganic base, easily causing flavanone open loop, chalcone is generated,
Chalcone is difficult to carry out above-mentioned reaction.
Specific embodiment:
The embodiment of the invention discloses the preparations of (Z, E) 5-OH- flavanone 7-O- glucosides -3- methine benzene derivative
Method；Those skilled in the art can use for reference present disclosure, be suitably modified realization of process parameters.In particular, it should be pointed out that institute
There are similar replacement and change apparent to those skilled in the art, they are considered as being included in the present invention.
Application of the invention is described by preferred embodiment, and related personnel can obviously not depart from the content of present invention, essence
Application as described herein is modified or appropriate changes and combinations in mind and range, carrys out implementation and application the technology of the present invention.
For a further understanding of the present invention, the following describes the present invention in detail with reference to examples.
The preparation of embodiment 1:3- (4- hydroxyl benzenyl)-aurantiamarin:
1.0 g of aurantiamarin, 0.20 g of parahydroxyben-zaldehyde that content is 95% are weighed, 3.0 mL tetrahydro pyrrole of DMSO is added
137 μ L are coughed up, 100 μ L of glacial acetic acid, 70 DEG C are stirred to react for 24 hours, and silica gel mixed sample is added with chloroform-methanol gradient elution and obtains yellow powder
775 mg of end are 3- (4- hydroxyl benzenyl)-aurantiamarin (cpd 1).1H NMR (400 MHz, DMSO) δ 12.63 (d, 1H:
5-OH), 10.27 (s, 1H:3'-OH), 9.17 (s, 1H:15-OH), [8.32+7.94 (d, 1H:11-H)], 7.27-7.31 (2H:
13-H+17-H), 6.75-7.00 (m, 5H:14-H+16-H+2'-H+5'-H+6'-H), 6.66 (d, 1H:2-H), 6.05-6.12
(dd, J=2.0,2H:H-6+H-8), 3.74 (s, 3H:4'-OCH3), 5.36 (1H:Gly-1 "), 4.90 (1H:Rha-1 " '),
1.10 (dd, 3H:Rha-6 " ')；13C NMR (100 MHz, DMSO-d6) δ 185.81 (d, C-4), 165.97 (d, C-7),
164.34 (C-9), 160.46 (C-5), 148.55 (C-4'), 147.75 (C-3'), 133.42 (C-1'), 130.38 (C-3),
118.93 (C-6'), 115.01 (C-2'), 112.85 (C-5'), 103.94 (C-10), 97.29 (C-6), 96.80 (C-8),
79.62 (C-2), 55.94 (4'-OCH3)；159.91(C-15),139.62(C-11),127.87(C-13+C-17),124.76
(C-12), 116.56 (C-14+C-16)；Gly:101.09 (Gly-1 "), 73.51 (Gly-2 "), 76.82 (Gly-3 "), 71.19
(Gly-4"),76.04(Gly-5"),66.65(Gly-6")；Rha:99.87 (Rha-1 " '), 70.09 (Rha-2 " '), 70.64
(Rha-3"'),72.65(Rha-4"'),68.80(Rha-5"'),18.29(Rha-6"').MS (ES-) 3.25e5, m/z:
714.15 [M]-, 608.96 [M- (4-OH-C6H4- CH-)]-, 405.48 [M-Gly-Rha]-, 301.90 [M-Gly-Rha- (4-
OH-C6H4- CH-)+2H+]-, 300.58 (100%) [M-Gly-Rha- (4-OH-C6H4-CH-)+H+]-；MS (ES+) 4.856e,
M/z:737.57 [M+Na+], 738.55 [M+H++Na+], 739.49 [M+2H++Na+], 475.45 [M-Rha- (4-OH-C6H4-)
+ H+], 476.45 (100%) M-Rha- (4-OH-C6H4)+2H+], 477.36 [M-Rha- (4-OH-C6H4)+3H+],
407.31 [M-Rha-Gly+2H+], calc.for:C35H38O16, reaction equation is as follows:
The preparation of embodiment 2:3- (3,4- hydroxyl benzenyl)-aurantiamarin:
Weigh content be 95% 1.5 g of aurantiamarin, be added nafoxidine 200 μ L, DMSO 4.0 mL dissolution, be added ice
3,4- hydroxy benzaldehyde, 0.25 g is added by several times, adds in 8h, the reaction was continued after 60 DEG C are stirred to react 3h by 150 μ L of acetic acid
3h is added silica gel mixed sample with chloroform-methanol gradient elution and obtains yellow powder 803mg, is 3- (3,4- hydroxyl benzenyl)-orange
Skin glycosides (cpd 2).1H NMR (400 MHz, DMSO) δ 12.63 (d, 1H:5-OH), 9.17 (s, 1H:3'-OH), [8.31+7.85
(d, 1H:11-H)], 6.99-6.70 (m, 6H:2'-H+5'-H+6'-H+13-H+16-H+17-H), 6.56 (d, 1H:2-H),
6.09 (d, 2H:6-H+8-H), 5.37 (s, 1H:2-H), 3.74 (s, 3H:4'-OCH3)；5.37 (s, 1H:Gly-1 " '-H),
4.95 (d, 1H:Rha-1 " '-H), 1.10 (d, 3H:Rha-6 " ').13C NMR (100 MHz, DMSO-d6) δ 185.79 (C-4),
165.92 (C-7), 164.34 (C-9), 160.20 (C-5), 149.21 (C-4'), 148.51 (C-3'), 147.14 (C-15),
146.07 (C-14), 139.97 (C-11), 130.34 (C-1'), 130.21 (C-3), 127.77 (C-12), 125.20 (C-17),
124.44 (C-6'), 118.23 (C-16), 116.49 (C-13), 114.99 (C-2'), 112.70 (C-5'), 103.89 (C-
10), 97.29 (C-6), 96.81 (C-8), 79.83 (C-2), 55.95 (4'-OCH3)；(101.10 Gly-1 "), 73.52 (Gly-
2 "), 76.04 (Gly-3 "), 71.21 (Gly-4 "), 76.71 (Gly-5 "), 66.81 (Gly-6 ")；99.86 (Rha-1 " '),
70.64 (Rha-2 " '), 70.79 (Rha-3 " '), 72.57 (Rha-4 " '), 68.78 (Rha-5 " '), 18.32 (Rha-6 " ').MS
(ES-) 8.18e6, m/z:729.64 (100%) [M-H]-, 730.65 [M]-, 731.6 [M+H]-；MS (ES+) 1.17e7, m/z:
753.58 (100%) [M+Na+], 754.31 [M+H++Na+], 755.63 [M+2H++Na+].Calc.for:C35H38O17, reaction
Formula is as follows:
The preparation of embodiment 3:3- (3,4- hydroxyl benzenyl)-aurantiin
Weigh content be 98% aurantiin 1.5g, be added nafoxidine 200 μ L, DMSO 4.0 mL dissolution, be added ice vinegar
3,4- hydroxy benzaldehyde, 0.30 g is added after 60 DEG C are stirred to react 3h in 150 μ L of acid by several times, adds in 8h, the reaction was continued 3h,
Silica gel mixed sample is added, yellow powder 845mg is obtained with chloroform-methanol gradient elution, is 3- (3,4- hydroxyl benzenyl)-shaddock ped
Glycosides (cpd 3).1H NMR (400 MHz, DMSO) δ 12.70 (d, 1H:5-OH), 9.65 (br, 1H:15-OH), 9.13 (br, 1H:
14-OH), [8.31+7.85 (d, 1H:11-H)], 7.17-7.30 (2H:13-H+17-H), 6.68-6.90 (m, 5H:2'-H+3'-
H+5'-H+6'-H+16-H), 6.50-6.65 (d, 1H:2-H), 5.32 (1H:2-H)；5.0-5.20 (2H:Gly-1 " '-H+Rha-
1 " '-H) 1.17 (d, 3H:Rha-6 " ').13C NMR (100 MHz, DMSO-d6) δ 185.76 (C-4), 165.27 (C-7),
164.14 (C-9), 160.12 (C-5), 158.24 (C-4'), 133.48 C-3), 129.23 (C-1'), 128.93 ((C-2'+C-
6'), 116.24 (C-3'+C-5'), 103.86 (C-10), 97.31 (C-6), 96.65 (C-8), 79.63 (C-2)；146.54(C-
15), 146.08 (C-14), 139.97 (C-11), 127.74 (C-12), 125.15 (C-17), 116.17 (C-16), 115.27
(C-13)；Gly:101.20 (Gly-1 "), 77.54 (Gly-2 "), 77.31 (Gly-3 "), 72.28 (Gly-4 "), 76.63
(Gly-5 "), 60.79 (Gly-6 ")；Rha:100.91 (Rha-1 " '), 70.02 (Rha-2 " '), 70.87 (Rha-3 " '),
72.34 (Rha-4 " '), 68.78 (Rha-5 " '), 18.49 (Rha-6 " ').MS (ES-) 3.51e, m/z:699.82 (100%)
[M-H]-, 700.78 [M]-, 701.77 [M+H]-；MS (ES+) 1.90e7, m/z:723.77 [M+Na+], 724.72 [M+H++Na
+], 475.53 (100%) [M+3H+-C14H12O3], 476.52M+4H+-C14H12O3], 497.55 [M+Na++2H+-C14H12O3],
498.51[M+Na++3H+-C14H12O3], 499.48 [M+Na++4H+-C14H12O3].(calc.for:C34H36O16), reaction equation
It is as follows:
It is to be noted that cleavage of mass spectrum rule may be as follows:
The preparation of embodiment 4:3- (3,4- dimethoxy benzenyl)-aurantiamarin,
The 1.5 g Veratraldehyde 0.402g of aurantiamarin that content is 95% is weighed, anhydrous DMSO is added
4.5ml
200 μ L of nafoxidine is added, 150 μ L of glacial acetic acid is added, after 70 DEG C are stirred to react 12h, silica gel mixed sample is added, with
Chloroform-methanol gradient elution obtains 1045 mg of yellow powder, is 3- (3,4- dimethoxy benzenyl)-aurantiamarin (cpd 4)
。1H NMR (400 MHz, DMSO) δ 12.63 (d, 1H:5-OH), 9.19 (s, 1H:3'-OH), [8.32+7.99 (d, 1H:11-
H)], 7.10-6.80 (m, 6H:2'-H+5'-H+6'-H+13-H+16-H+17-H), 6.65 (d, 1H:2-H), 6.20-6.00 (d,
2H:6-H+8-H), 3.74 (s, 3H:4'-OCH3), 3.80 (s, 3H:15-OCH3), 3.64 (s, 3H:14-OCH3)；5.35(s,
1H:Gly-1 " '-H), 4.95 (d, 1H:Rha-1 " '-H), 1.10 (d, 3H:Rha-6 " ').13C NMR(100 MHz,DMSO-d6)
δ 185.62 (d, C-4), 166.13 (C-7), 164.37 (C-9), 160.30 (C-5), 149.12 (C-4'), 148.66 (C-3'),
130.57 (C-1'), 128.85 (C-3), 124.42 (C-6'), 115.21 (C-2'), 112.74 (C-5'), 103.94 (C-10),
97.20 (C-6), 96.77 (C-8), 79.63 (C-2), 55.98 (4'-OCH3)；151.36 (C-15), 147.20 (C-14),
139.54 (C-11), 126.38 (C-12), 119.24 (C-17), 114.40 (C-16), 122.35 (C-16), 55.80 (14-
OCH3), 56.12 (15-OCH3)；101.11 (Gly-1 "), 73.52 (Gly-2 "), 76.06 (Gly-3 "), 71.19 (Gly-4 "),
76.82 (Gly-5 "), 66.63 (Gly-6 ")；99.88 (Rha-1 " '), 70.10 (Rha-2 " '), 70.79 (Rha-3 " '),
72.58 (Rha-4 " '), 68.80 (Rha-5 " '), 18.30 (d, Rha-6 " ').MS (ES-) 3.65e6, m/z:757.69
(100%) [M-H]-, 739.69 [M+Na+-3CH3]-, 713.32 [M-3CH3]-, 699.42 [M-2CH3-OCH3+H+]-, 698.50
[M-2CH3-OCH3]-, 610.34 [M-Rha-H]-；MS (ES+) 6.41e5, m/z:781.61 (100%) [M+Na+], 782.60
[M+H++Na+], 783.52 [M+2H++Na+], 759.85 [M+H+], 759.85 [M+H+], 613.54 [M-Rha+2H+].
(calc.for:C37H42O17), reaction equation is as follows:
The preparation of embodiment 5:3- (3,4- dimethoxy benzenyl)-aurantiin:
1.0 g of aurantiin that content is 98% is weighed, 4 mL of DMSO dissolution, Veratraldehyde 0.35 is added
G, 210 μ L of nafoxidine, are added 160 μ L of glacial acetic acid, and 60 DEG C closed to be stirred to react 20h, and n-butanol 60ml is added, is added 0.5%
60 mL of aqueous hydrochloric acid solution dilution, discards aqueous, elutes n-butanol layer by several times with water 15ml, is spin-dried for, with methanol solvate, silica gel is mixed
Sample, chloroform-methanol gradient elution obtain yellow powder 896mg, are 3- (3,4- dimethoxy benzenyl)-aurantiin (cpd
5)。1H NMR (400 MHz, DMSO) δ 12.63 (d, 1H:5-OH), 9.69 (s, 1H:3'-OH), [8.30+7.99 (d, 1H:11-
)], H 7.30-7.23 (2H:13-H+17-H), 7.10-6.70 (m, 5H:2'-H+3'-H+5'-H+6'-H+16-H), 6.65 (d,
1H:2-H), 6.20-5.90 (d, 2H:6-H+8-H), 3.79 (s, 3H:15-OCH3), 3.61 (s, 3H:14-OCH3)；5.30(s,
1H:Gly-1 " '-H), 5.07 (1H:Rha-1 " '-H), 1.15 (d, 3H:Rha-6 " ').13C NMR(100 MHz,DMSO-d6)δ
185.49 (d, C-4), 165.67 (C-7), 164.29 (C-9), 160.20 (C-5), 158.52 (C-4'), 133.50 (C-3),
129.53 (C-1'), 128.79 (C-2'+C-6'), 116.27 (C-3'+C-5'), 103.35 (C-10), 97.33 (C-6),
96.57 (C-8), 78.02 (C-2)；151.35 (C-15), 149.09 (C-14), 139.58 (C-11), 126.37 (C-12),
125.18 (C-16), 112.38 (C-16), 111.20.35 (C-13), 55.72 (14-OCH3), 56.12 (15-OCH3)；
101.12 (Gly-1 "), 77.51 (Gly-2 "), 76.60 (Gly-3 "), 72.27 (Gly-4 "), 77.32 (Gly-5 "), 60.82
(Gly-6")；100.00 (Rha-1 " '), 70.05 (Rha-2 " '), 70.87 (Rha-3 " '), 72.32 (Rha-4 " '), 68.80
(Rha-5 " '), 18.45 (d, Rha-6 " ')；MS (ES-) 1.03e7, m/z:727.66 (100%) [M-H]-, 728.54 [M]-,
729.60 [M+H]-, 730.51 [M+2H]-；MS (ES+) 1.04e6, m/z:751.52 (100%) [M+Na+], 752.54 [M+H+
+ Na+], 753.59 [M+2H++Na+], 754.67 [M+3H++Na+], 767.53 [M+K+], 768.52 [M+H++K+], 730.56
[M+2H+], 728.20 [M+], 700.45 [M-2CH3+2H+].(calc.for:C37H42O17), reaction equation is as follows:
The preparation of embodiment 6:3- (4-N, N dimethyl benzenyl)-aurantiamarin:
Aurantiamarin 1.5 g, 4-N, 0.402 g of N dimethyl benzene that content is 95% are weighed, anhydrous 5.0 mL of DMSO is added,
150 μ L of glacial acetic acid is added in 170 μ L of nafoxidine, and under nitrogen charging gas shielded, after 70 DEG C are stirred to react 24 h, silica gel mixed sample is added,
With chloroform-methanol gradient elution, 0.762 mg of red powder is obtained, is 3- (4-N, N dimethyl benzenyl)-aurantiamarin (cpd
6)。1H NMR (400 MHz, DMSO-d6) δ 12.86 (d, 1H:5-OH), 9.14 (s, 1H:3'-OH), 7.93 (s, 1H:11-H),
δ 7.29 (2H:13-H+17-H), 6.98-6.77 (m, 3H:2'-H+5'-H+6'-H), 6.74 (2H:14-H+16-H), 6.60 (s,
1H:2-H), 3.74 (s, 3H:4'-OCH of 6.12-6.00 (3H:6-H+8-H)3), 2.99 (s, 6H:15-N (CH3)2), 5.37 (s,
1H:Gly-1 " '-H), 4.94 (dd, 1H:Rha-1 " '-H), 1.10 (d, 3H:Rha-6 " ').13C NMR(100 MHz,DMSO-
D6) δ 185.37 (C-4), 165.63 (C-7), 164.06 (C-9), 160.10 (C-5), 148.50 (C-4'), 147.10 (C-
3'), 133.59 (C-1'), 130.68 (C-3), 118.87 (C-6'), 115.13 (C-2'), 112.67 (C-5'), 103.85 (C-
10), 97.21 (C-6), 96.81 (C-8), 79.83 (C-2), 55.95 (4'-OCH3)；152.14 (C-15), 140.19 (C-
11), 125.05 (C-13+C17), 120.084 (C-12), 112.37 (C-14+C16)；Gly:101.11 (Gly-1 "), 73.52
(Gly-2 "), 76.83 (Gly-3 "), 71.22 (Gly-4 "), 76.97 (Gly-5 "), 66.82 (Gly-6 ")；Rha:99.87
(Rha-1 " '), 70.19 (Rha-2 " '), 70.64 (Rha-3 " '), 72.63 (Rha-4 " '), 68.78 (Rha-5 " '), 18.32
(Rha-6"').MS (ES-) 1.57e6, m/z:740.64 (100%) [M-H]-, 741.54 [M]-, 742.51 [M+H]-,
714.61[M-2CH3+3H]-；MS (ES+) 4.67e5, m/z:764.60 (100%) [M+Na+], 765.63 [M+H++Na+],
766.53 [M+2H++Na+], 742.57 [M+H+], 773.42 [M+H+], 744.23 [M+2H+], 728.713 [M-CH3+ 2H+],
701.71[M-CH3+ 2H+-CO], 701.71 [M+H+].(calc.for:C37H43 N O15), reaction equation is as follows:
The preparation of embodiment 7:3- (3,4- dimethoxybenzyliden)-aurantiin,
According to embodiment 5, solvent DMSO is changed into THF, THF amount is 20ml, and temperature is 60 DEG C, and other conditions are constant, reaction
Time is 36h, and end of reaction is spin-dried for, and methanol dissolution is added, and silica gel mixed sample obtains 3- (3,4- bis- with chloroform-methanol gradient elution
Methoxybenzene methine) -782 mg of aurantiin yellow powder.
The preparation of embodiment 8:3- (3,4- dimethoxybenzyliden)-aurantiin,
According to embodiment 5, solvent DMSO is changed into glycerine-methanol (3:1) mixed solution 20ml, temperature is 80 DEG C, other
Condition is constant, reaction time 10h, end of reaction, and n-butanol 80ml is added, and 0.5% aqueous hydrochloric acid solution, 60 mL dilution is added,
Aqueous is discarded, with water 15ml elution n-butanol layer by several times, is spin-dried for, with methanol solvate, silica gel mixed sample, chloroform-methanol gradient elution,
Obtain 3- (3,4- dimethoxy benzenyl)-aurantiin yellow powder 672mg.
The preparation of embodiment 9:3- (3,4- dimethoxy benzenyl)-aurantiin,
According to embodiment 5, solvent DMSO is changed into ethylene glycol solvent 12ml, change nafoxidine into piperidines, piperidines amount is 240
μ L temperature is 80 DEG C, and other conditions are constant, reaction time 15h, end of reaction, and n-butanol 80ml is added, and 0.5% hydrochloric acid is added
60 mL of aqueous solution dilution, discards aqueous, and water 15ml elutes n-butanol layer by several times, is spin-dried for, with methanol solvate, silica gel mixed sample, chlorine
Imitation-carbinol gradient elution obtains 3- (3,4- dimethoxybenzyliden)-aurantiin yellow powder 512mg.
The preparation of embodiment 10:3- (3,4- dimethoxy benzenyl)-aurantiin,
According to embodiment 5, solvent DMSO is changed into DMF, change nafoxidine into diethylamine, diethylamine amount is 230 μ L, ice second
Sour dosage is 300 μ L, and temperature is 90 DEG C, and other conditions are constant, end of reaction, and n-butanol 80ml is added, and 60 mL of aqueous solution is added
Dilution, discards aqueous, and water 15ml elutes n-butanol layer by several times, is spin-dried for, with methanol solvate, silica gel mixed sample, chloroform-methanol gradient is washed
It is de-, obtain 3- (3,4- dimethoxy benzenyl)-aurantiin yellow powder 486mg.
The preparation of embodiment 11:3- (3,4- dimethoxy benzenyl)-aurantiin,
According to embodiment 5, glacial acetic acid is changed into lactic acid, other conditions are constant, obtain 3- (3,4- dimethoxy benzenyl)-shaddock
Skin glycosides yellow powder 742mg.
The preparation of embodiment 12:3- (3,4- dimethoxy benzenyl)-aurantiin,
According to embodiment 5, glacial acetic acid is changed into propionic acid, other conditions are constant, obtain 3- (3,4- dimethoxy benzenyl)-shaddock
Skin glycosides yellow powder 796mg.
The preparation of embodiment 13:3- (4-Cl benzenyl)-aurantiin,
According to embodiment 5, Veratraldehyde is changed into 4-Cl benzaldehyde, temperature is reduced to stirring at normal temperature reaction, instead
It is 72h between seasonable, other conditions are constant, end of reaction, and silica gel mixed sample is added, and chloroform-methanol gradient elution obtains 3- (4-Cl benzene
Methine) -922 mg of aurantiin yellow powder (cpd 7).702.17 [M-], (calc.for:C34H35ClO14)。
The preparation of embodiment 14:3- (3,4,5- trimethoxy benzenyl)-aurantiamarin,
According to embodiment 4, Veratraldehyde is changed into 3,4,5-Trimethoxybenzaldehyde, reaction time 72h,
Other conditions are constant, end of reaction, and silica gel mixed sample is added, and chloroform-methanol gradient elution obtains 3- (3,4,5- trimethoxy-benzenes
Methyl) -786 mg of aurantiamarin yellow powder (cpd 8).788.25 [M-], (calc.for:C38H44O18)。
Following embodiments are mainly to 5-OH-3- of the present invention (phenyl derivatives-methine)-flavanone -7-
O-glycosides, applied to anti-inflammatory, antioxidant food, cosmetic composition and antibacterial, the group of antitumor, cardiovascular and cerebrovascular protection drug
Close the explanation of the service condition of object.
Embodiment 15:
The purpose of the present embodiment be measure its structure modified outcome after solubility variation, with aurantiamarin, aurantiin and its
Illustrate for structure modified outcome.According to pharmacopeia to easily dissolution, it is readily soluble, dissolution, slightly molten, slightly soluble, indissoluble regulation.It takes for reality
Compound 10mg is tested, different solvents are added with liquid-transfering gun or pipette, observation dissolution is existing after closed ultrasonic 20s, closed placement 1h
As if insoluble, continuing growing solvent volume dosage, repeating aforesaid operations recording solution volumetric usage.According to States Pharmacopoeia specifications, sentence
Seco compound solubility property, is shown in Table 1,
1 aurantiamarin of table, hesperidin methyl, aurantiin and its structure modified outcome solubility in different solvents compare
Illustrate: table 1 shows that aurantiamarin passes through the structural modification of structure 3- methine benzene derivative, and the D ring newly introduced contains
Polar group, such as hydroxyl, amido, methoxyl group etc. increases the active force of same solvent；In addition, because steric hindrance acts on, B, D ring
It is distorted, coplanar variation, crystallization forms difficulty increase, significantly increases dissolubility, solubility property is excellent.Certainly,
Also difficulty is brought to purifying, is not easy to crystallize to purify.In addition, the benzaldehyde containing hydroxyl and aurantiamarin are condensed, to aurantiamarin one
Fixed solubilization, it is another its in water, in alcohol, have certain solubility in acetone.
Embodiment 16:
The purpose of present embodiment: being influence of the preliminary assessment structure modified outcome to oxidation resistance: using DPPH method
With Fenton reaction method, illustrate by taking aurantiamarin, aurantiin and its structure modified outcome as an example.
To DPPH clearance test: DPPH is a kind of stable free radical, and alcoholic solution is dark purple, at 517nm
There is an absorption peak.Free radical scavenger in reaction system can match with the single electron of DPPH and make A517nmIt reduces, therefore, root
According to A517nmVariation detect the removing situation of free radical, evaluate the oxidation resistance of sample.6 gradients are arranged in hesperidin methyl
Concentration, be 5,10,15,20,25,30,60 μ g/mL 50% ethanol solution of sample, take 2.0 mL samples, add people
1.0mLDPPH methanol solution (3.0 × 10-4Mol/L), each sample light absorption value (A is measured at 520nm after mixing 30mini), often
Part sample operation repetitive 3 times, finally takes its average value.DPPH free radical scavenging activity K is calculated by formula: K (%)=[1- (Ai-
Aj)/Ac] in × 100 formulas: Ac is that 1.0mL DPPH methanol solution (3.0 × 10 is added in 2.0 mL50% ethyl alcohol-4Mol/L it) mixes
Absorbance afterwards, Aj are that the mixed absorbance of 1.0mL methanol is added in 2.0mL sample.Sample to be tested is write a Chinese character in simplified form constant, and sample is such as
Under: aurantiamarin, aurantiin, cpd 1-8 the results are shown in Table 2:
2 aurantiamarin of table, hesperidin methyl, aurantiin and its structure modified outcome anti-DPPH ability
Illustrate: removing the dosage of DPPH free radical, it is main related with supplied for electronic, increase double bond, oxidation resistance is omited
There is increase, increase the hydroxyl that can be conjugated with carbonyl, amido can be obviously improved oxidation resistance.Such as 3,4- dihydroxy, antioxygen
Change ability increases nearly 1 times.Especially increase with concentration, solubility is larger, conjugation ability it is increased, oxidation resistance it is excellent
Gesture is more obvious.
To OH clearance test: being reacted referring to Fenton, utilize H202, with Fe2+ mixing generates OH, but OH activity is very
Height, the time-to-live is short, and salicylic acid is added in system, can effectively be combined with 0H, generates colored compound, exists in product
There is strong absorption under 510nm.If antioxidant is added in system, OH will be competed with salicylic acid, to make coloring matter
It reduces.Under the premise of fixation response time, to the identical reaction system (H of 8.8mmo1/L202Solution 2mL, 9mmol/L's
FeSO4Salicylic acid-ethanol solution 2mL of solution 2mL, 9mo1/L) 2 mL of hesperidin methyl solution of various concentration is added.Finally
Add H202Start to react, 37 DEG C of reaction 0.5h compare using distilled water as reference with the blank solution of reagent, measure at 510 nm
Absorbance under each concentration just can measure scavenging effect of the hesperidin methyl solution to OH, clearance rate calculation formula: remove
In rate (%)=[1- (Ax-Axo)/Ao] × 100% formula: Ao is the absorbance of blank control liquid；Ax is after sample solution is added
Absorbance；Axo is that color developing agent H is not added202The absorbance of sample solution background.Sample to be tested is constant.It the results are shown in Table 3:
The ability of the oh resistant of 3 aurantiamarin of table, hesperidin methyl, aurantiin and its structure modified outcome
Illustrate: showing aurantiamarin from table 3, introduce electron-donating group in aurantiin molecule, it can be improved and removes free radical
Ability, especially 3- (3,4- hydroxyl benzenyl)-aurantiin, 3- (3,4- hydroxyl benzenyl)-aurantiamarin oxidation resistance
Much higher than hesperidin methyl, the latter can replace, can be used as food, drug, antioxidant in cosmetics.
Embodiment 17
The purpose of the present embodiment: it influence of the preliminary assessment structure modified outcome to anti-inflammatoryization ability: is induced using dimethylbenzene
Mouse ear swelling experimental method illustrates by taking aurantiamarin, aurantiin and its structure modified outcome as an example.
Dimethylbenzene inducing mouse ear swelling: taking Kunming mouse 132, is randomly divided into 22 groups by weight, every group 6, female
Hero is fifty-fifty, i.e. model group (gavaging 0.5%CMC liquid 0.4mL/20g), positive drug group (naproxen 45mg/kg), aurantiamarin, shaddock ped
Glycosides, cpd1-8 compound are respectively two groups (gavaging 0.6% and 0.3% drug respectively).The above each group mouse is administered daily 1 time/d,
Continuous 5 d, in 30min after the last administration, 50 μ L of dimethylbenzene is uniformly smeared on two sides before and after mouse right ear, and auris dextra compares, and is caused
30min cervical dislocation puts to death mouse after inflammation, removes left and right, ear edge with 7mm diameter punch, is weighed respectively with electronic balance, with
Left and right auricle weight difference indicates swelling, and calculates inhibiting rate (%)=(the model group swelling-administration group that is averaged is averaged swelling
Degree)/model group is averaged swelling × 100%.Significance difference comparative experiments the results are shown in Table 4 between carrying out group:
The influence of 4 aurantiamarin of table, shaddock ped glycoside derivates paraxylene inducing mouse ear swelling
With negative group than * P < 0.05, P < 0.001 * * P < 0.01, * * *
Illustrate, flavone compound of the present invention, the influence to anti-inflammatoryization ability is significant.
Claims (6)
1. one kind (Z, E) -5-OH-3-(phenyl derivatives-methine)-flavanone -7-O- glucosides, general structure is shown in (I)
It is shown,
Wherein: R1For glucosyl group, rue glycosyl, neohesperidose base, glucuronic acid base；R2For-H ,-OH ,-OCH3；R3For-
H、-OH、-OCH3,-F ,-Cl, Dan Jituan or more group in-Br；R4For-H ,-OH ,-OCH3,-Cl ,-Br ,-NO2, (methylenedioxy)
Dan Jituan or more group in base.
2. (Z, E) -5-OH-3-(phenyl derivatives-methine according to claim 1)-flavanone -7-O- glucosides
Preparation method, be using 5-OH flavanone -7-O- glucosides as raw material, be to urge with organic base and organic acid in polar solvent
Agent is reacted by aldol condensation with structure formula (III) and is made, and (Z, E) -5-OH flavanone -7-O- is controlled
The mol ratio of glucosides and benzaldehydes is 3:1-1:3, and reaction temperature is in room temperature to 120 DEG C；Its structure formula (III)
R4For-H ,-OH ,-OCH3,-Cl ,-Br ,-NO2, Dan Jituan or more group in methylene-dioxy；
The organic base, be dimethylamine, diethylamine, nafoxidine, piperidines, piperazine, morpholine any one.
3. (Z, E) -5-OH-3-(phenyl derivatives-methine according to claim 2)-flavanone -7-O- glucosides
Preparation method, it is characterized in that the 5-OH flavanone 7-O- glucosides, structural formula are shown in (II),
,
Wherein: R1、R2、R3With R in structure (I) formula1、R2、R3Group meaning is identical.
4. (Z, E) -5-OH-3-(phenyl derivatives-methine according to claim 2)-flavanone -7-O- glucosides
Preparation method, it is characterized in that the polar solvent be DMSO, DMF, THF, alcohols any one；The alcohols be methanol,
Ethyl alcohol, propyl alcohol, isopropanol, ethylene glycol, propylene glycol, glycerine any one.
5. (Z, E) -5-OH-3-(phenyl derivatives-methine according to claim 2)-flavanone -7-O- glucosides
Preparation method, it is characterized in that the organic acid is formic acid, acetic acid, propionic acid, butyric acid, valeric acid, caproic acid, benzoic acid, phenylacetic acid, benzene
Propionic acid, lactic acid, succinic acid, tartaric acid any one.
6. (Z, E) -5-OH-3-(phenyl derivatives-methine according to claim 1)-flavanone -7-O- glucosides,
It is used to prepare anti-inflammatory, antioxidant food, cosmetic composition, the composition of antibacterial, antitumor, cardiovascular and cerebrovascular protection drug.
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| Antioxidant properties of di-tert-butylhydroxylated flavonoids;Lebeau, Jonathan，等;《Free Radical Biology & Medicine》;20001231;第29卷(第9期);第900-912页 |
| Synthesis and antioxidant activity of [60]fullerene-flavonoid conjugates;Enes, Roger F.，等;《Tetrahedron》;20081025;第65卷(第1期);第253-262页 |
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