CN109053844A - Epigallocatechin stigmasterol functional molecular, preparation method and application - Google Patents
Epigallocatechin stigmasterol functional molecular, preparation method and application Download PDFInfo
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- CN109053844A CN109053844A CN201810950946.2A CN201810950946A CN109053844A CN 109053844 A CN109053844 A CN 109053844A CN 201810950946 A CN201810950946 A CN 201810950946A CN 109053844 A CN109053844 A CN 109053844A
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- epigallocatechin
- stigmasterol
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- functional molecular
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- XMOCLSLCDHWDHP-IUODEOHRSA-N epi-Gallocatechin Chemical compound C1([C@H]2OC3=CC(O)=CC(O)=C3C[C@H]2O)=CC(O)=C(O)C(O)=C1 XMOCLSLCDHWDHP-IUODEOHRSA-N 0.000 title claims abstract description 121
- XMOCLSLCDHWDHP-UHFFFAOYSA-N L-Epigallocatechin Natural products OC1CC2=C(O)C=C(O)C=C2OC1C1=CC(O)=C(O)C(O)=C1 XMOCLSLCDHWDHP-UHFFFAOYSA-N 0.000 title claims abstract description 62
- DZYNKLUGCOSVKS-UHFFFAOYSA-N epigallocatechin Natural products OC1Cc2cc(O)cc(O)c2OC1c3cc(O)c(O)c(O)c3 DZYNKLUGCOSVKS-UHFFFAOYSA-N 0.000 title claims abstract description 62
- OILXMJHPFNGGTO-UHFFFAOYSA-N (22E)-(24xi)-24-methylcholesta-5,22-dien-3beta-ol Natural products C1C=C2CC(O)CCC2(C)C2C1C1CCC(C(C)C=CC(C)C(C)C)C1(C)CC2 OILXMJHPFNGGTO-UHFFFAOYSA-N 0.000 title claims abstract description 60
- OQMZNAMGEHIHNN-UHFFFAOYSA-N 7-Dehydrostigmasterol Natural products C1C(O)CCC2(C)C(CCC3(C(C(C)C=CC(CC)C(C)C)CCC33)C)C3=CC=C21 OQMZNAMGEHIHNN-UHFFFAOYSA-N 0.000 title claims abstract description 60
- HZYXFRGVBOPPNZ-UHFFFAOYSA-N UNPD88870 Natural products C1C=C2CC(O)CCC2(C)C2C1C1CCC(C(C)=CCC(CC)C(C)C)C1(C)CC2 HZYXFRGVBOPPNZ-UHFFFAOYSA-N 0.000 title claims abstract description 60
- LGJMUZUPVCAVPU-UHFFFAOYSA-N beta-Sitostanol Natural products C1CC2CC(O)CCC2(C)C2C1C1CCC(C(C)CCC(CC)C(C)C)C1(C)CC2 LGJMUZUPVCAVPU-UHFFFAOYSA-N 0.000 title claims abstract description 60
- HCXVJBMSMIARIN-PHZDYDNGSA-N stigmasterol Chemical compound C1C=C2C[C@@H](O)CC[C@]2(C)[C@@H]2[C@@H]1[C@@H]1CC[C@H]([C@H](C)/C=C/[C@@H](CC)C(C)C)[C@@]1(C)CC2 HCXVJBMSMIARIN-PHZDYDNGSA-N 0.000 title claims abstract description 60
- 235000016831 stigmasterol Nutrition 0.000 title claims abstract description 60
- 229940032091 stigmasterol Drugs 0.000 title claims abstract description 60
- BFDNMXAIBMJLBB-UHFFFAOYSA-N stigmasterol Natural products CCC(C=CC(C)C1CCCC2C3CC=C4CC(O)CCC4(C)C3CCC12C)C(C)C BFDNMXAIBMJLBB-UHFFFAOYSA-N 0.000 title claims abstract description 60
- 238000002360 preparation method Methods 0.000 title claims abstract description 18
- KDYFGRWQOYBRFD-UHFFFAOYSA-N Succinic acid Natural products OC(=O)CCC(O)=O KDYFGRWQOYBRFD-UHFFFAOYSA-N 0.000 claims abstract description 19
- 230000003078 antioxidant effect Effects 0.000 claims abstract description 9
- 239000003963 antioxidant agent Substances 0.000 claims abstract description 5
- 238000006243 chemical reaction Methods 0.000 claims description 15
- VHYFNPMBLIVWCW-UHFFFAOYSA-N 4-Dimethylaminopyridine Chemical compound CN(C)C1=CC=NC=C1 VHYFNPMBLIVWCW-UHFFFAOYSA-N 0.000 claims description 10
- 238000005859 coupling reaction Methods 0.000 claims description 10
- 150000008065 acid anhydrides Chemical class 0.000 claims description 8
- -1 1- ethyl-(3- dimethylaminopropyl) Chemical group 0.000 claims description 7
- FALRKNHUBBKYCC-UHFFFAOYSA-N 2-(chloromethyl)pyridine-3-carbonitrile Chemical compound ClCC1=NC=CC=C1C#N FALRKNHUBBKYCC-UHFFFAOYSA-N 0.000 claims description 7
- 239000001384 succinic acid Substances 0.000 claims description 7
- 229940014800 succinic anhydride Drugs 0.000 claims description 7
- QOSSAOTZNIDXMA-UHFFFAOYSA-N Dicylcohexylcarbodiimide Chemical compound C1CCCCC1N=C=NC1CCCCC1 QOSSAOTZNIDXMA-UHFFFAOYSA-N 0.000 claims description 6
- PFTAWBLQPZVEMU-DZGCQCFKSA-N (+)-catechin Chemical compound C1([C@H]2OC3=CC(O)=CC(O)=C3C[C@@H]2O)=CC=C(O)C(O)=C1 PFTAWBLQPZVEMU-DZGCQCFKSA-N 0.000 claims description 4
- OAKJQQAXSVQMHS-UHFFFAOYSA-N Hydrazine Chemical compound NN OAKJQQAXSVQMHS-UHFFFAOYSA-N 0.000 claims description 4
- 229930182558 Sterol Natural products 0.000 claims description 4
- 239000002253 acid Substances 0.000 claims description 4
- 125000002252 acyl group Chemical group 0.000 claims description 4
- 235000006708 antioxidants Nutrition 0.000 claims description 4
- 239000003054 catalyst Substances 0.000 claims description 4
- 150000003839 salts Chemical class 0.000 claims description 4
- 235000003702 sterols Nutrition 0.000 claims description 4
- ADRVNXBAWSRFAJ-UHFFFAOYSA-N catechin Natural products OC1Cc2cc(O)cc(O)c2OC1c3ccc(O)c(O)c3 ADRVNXBAWSRFAJ-UHFFFAOYSA-N 0.000 claims description 3
- 235000005487 catechin Nutrition 0.000 claims description 3
- 239000003153 chemical reaction reagent Substances 0.000 claims description 3
- 229950001002 cianidanol Drugs 0.000 claims description 3
- 230000008878 coupling Effects 0.000 claims description 3
- 238000010168 coupling process Methods 0.000 claims description 3
- 150000003432 sterols Chemical class 0.000 claims description 3
- 244000046052 Phaseolus vulgaris Species 0.000 claims description 2
- 235000010627 Phaseolus vulgaris Nutrition 0.000 claims description 2
- 240000003152 Rhus chinensis Species 0.000 claims description 2
- 235000014220 Rhus chinensis Nutrition 0.000 claims description 2
- 239000003795 chemical substances by application Substances 0.000 claims description 2
- LSACYLWPPQLVSM-UHFFFAOYSA-N isobutyric acid anhydride Chemical compound CC(C)C(=O)OC(=O)C(C)C LSACYLWPPQLVSM-UHFFFAOYSA-N 0.000 claims description 2
- 150000008064 anhydrides Chemical class 0.000 claims 1
- KDYFGRWQOYBRFD-NUQCWPJISA-N butanedioic acid Chemical compound O[14C](=O)CC[14C](O)=O KDYFGRWQOYBRFD-NUQCWPJISA-N 0.000 abstract description 5
- 125000002887 hydroxy group Chemical group [H]O* 0.000 abstract description 5
- 230000003026 anti-oxygenic effect Effects 0.000 abstract description 3
- 125000004185 ester group Chemical group 0.000 abstract description 3
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 abstract description 2
- 238000004519 manufacturing process Methods 0.000 abstract description 2
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 15
- 235000013824 polyphenols Nutrition 0.000 description 11
- BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 10
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 9
- 150000008442 polyphenolic compounds Chemical class 0.000 description 9
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 7
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 6
- 241000196324 Embryophyta Species 0.000 description 6
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 6
- 230000000694 effects Effects 0.000 description 6
- 229910000027 potassium carbonate Inorganic materials 0.000 description 5
- NWZSZGALRFJKBT-KNIFDHDWSA-N (2s)-2,6-diaminohexanoic acid;(2s)-2-hydroxybutanedioic acid Chemical compound OC(=O)[C@@H](O)CC(O)=O.NCCCC[C@H](N)C(O)=O NWZSZGALRFJKBT-KNIFDHDWSA-N 0.000 description 4
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 4
- 150000002148 esters Chemical class 0.000 description 4
- IKDUDTNKRLTJSI-UHFFFAOYSA-N hydrazine monohydrate Substances O.NN IKDUDTNKRLTJSI-UHFFFAOYSA-N 0.000 description 4
- 230000002401 inhibitory effect Effects 0.000 description 4
- 230000001766 physiological effect Effects 0.000 description 4
- 239000002904 solvent Substances 0.000 description 4
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 4
- WFDIJRYMOXRFFG-UHFFFAOYSA-N Acetic anhydride Chemical compound CC(=O)OC(C)=O WFDIJRYMOXRFFG-UHFFFAOYSA-N 0.000 description 3
- NLZUEZXRPGMBCV-UHFFFAOYSA-N Butylhydroxytoluene Chemical compound CC1=CC(C(C)(C)C)=C(O)C(C(C)(C)C)=C1 NLZUEZXRPGMBCV-UHFFFAOYSA-N 0.000 description 3
- 239000011230 binding agent Substances 0.000 description 3
- 235000010354 butylated hydroxytoluene Nutrition 0.000 description 3
- HVYWMOMLDIMFJA-DPAQBDIFSA-N cholesterol Chemical compound C1C=C2C[C@@H](O)CC[C@]2(C)[C@@H]2[C@@H]1[C@@H]1CC[C@H]([C@H](C)CCCC(C)C)[C@@]1(C)CC2 HVYWMOMLDIMFJA-DPAQBDIFSA-N 0.000 description 3
- 235000014113 dietary fatty acids Nutrition 0.000 description 3
- 238000001035 drying Methods 0.000 description 3
- 239000000194 fatty acid Substances 0.000 description 3
- 229930195729 fatty acid Natural products 0.000 description 3
- 150000004665 fatty acids Chemical class 0.000 description 3
- ISWSIDIOOBJBQZ-UHFFFAOYSA-N phenol group Chemical group C1(=CC=CC=C1)O ISWSIDIOOBJBQZ-UHFFFAOYSA-N 0.000 description 3
- 238000000746 purification Methods 0.000 description 3
- 150000003254 radicals Chemical class 0.000 description 3
- 238000012360 testing method Methods 0.000 description 3
- 238000005406 washing Methods 0.000 description 3
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 2
- 208000024172 Cardiovascular disease Diseases 0.000 description 2
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 2
- 244000269722 Thea sinensis Species 0.000 description 2
- 239000003513 alkali Substances 0.000 description 2
- 239000002585 base Substances 0.000 description 2
- 208000029078 coronary artery disease Diseases 0.000 description 2
- 238000001514 detection method Methods 0.000 description 2
- 201000010099 disease Diseases 0.000 description 2
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 description 2
- 230000032050 esterification Effects 0.000 description 2
- 238000005886 esterification reaction Methods 0.000 description 2
- 235000013305 food Nutrition 0.000 description 2
- 235000013376 functional food Nutrition 0.000 description 2
- 235000009569 green tea Nutrition 0.000 description 2
- 238000010438 heat treatment Methods 0.000 description 2
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 2
- 238000000034 method Methods 0.000 description 2
- 150000002989 phenols Chemical class 0.000 description 2
- 230000002265 prevention Effects 0.000 description 2
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 2
- WMBWREPUVVBILR-WIYYLYMNSA-N (-)-Epigallocatechin-3-o-gallate Chemical compound O([C@@H]1CC2=C(O)C=C(C=C2O[C@@H]1C=1C=C(O)C(O)=C(O)C=1)O)C(=O)C1=CC(O)=C(O)C(O)=C1 WMBWREPUVVBILR-WIYYLYMNSA-N 0.000 description 1
- 244000235603 Acacia catechu Species 0.000 description 1
- 235000006226 Areca catechu Nutrition 0.000 description 1
- 206010003210 Arteriosclerosis Diseases 0.000 description 1
- 206010003211 Arteriosclerosis coronary artery Diseases 0.000 description 1
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical group [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 1
- 206010008190 Cerebrovascular accident Diseases 0.000 description 1
- 240000006927 Foeniculum vulgare Species 0.000 description 1
- 235000004204 Foeniculum vulgare Nutrition 0.000 description 1
- WMBWREPUVVBILR-UHFFFAOYSA-N GCG Natural products C=1C(O)=C(O)C(O)=CC=1C1OC2=CC(O)=CC(O)=C2CC1OC(=O)C1=CC(O)=C(O)C(O)=C1 WMBWREPUVVBILR-UHFFFAOYSA-N 0.000 description 1
- 208000006011 Stroke Diseases 0.000 description 1
- 238000010521 absorption reaction Methods 0.000 description 1
- 230000009471 action Effects 0.000 description 1
- 230000032683 aging Effects 0.000 description 1
- 230000003266 anti-allergic effect Effects 0.000 description 1
- 230000003110 anti-inflammatory effect Effects 0.000 description 1
- 230000003064 anti-oxidating effect Effects 0.000 description 1
- 230000002155 anti-virotic effect Effects 0.000 description 1
- 208000011775 arteriosclerosis disease Diseases 0.000 description 1
- 239000008280 blood Substances 0.000 description 1
- 210000004369 blood Anatomy 0.000 description 1
- YHASWHZGWUONAO-UHFFFAOYSA-N butanoyl butanoate Chemical compound CCCC(=O)OC(=O)CCC YHASWHZGWUONAO-UHFFFAOYSA-N 0.000 description 1
- RYYVLZVUVIJVGH-UHFFFAOYSA-N caffeine Chemical compound CN1C(=O)N(C)C(=O)C2=C1N=CN2C RYYVLZVUVIJVGH-UHFFFAOYSA-N 0.000 description 1
- 150000001732 carboxylic acid derivatives Chemical class 0.000 description 1
- 230000003130 cardiopathic effect Effects 0.000 description 1
- 235000013339 cereals Nutrition 0.000 description 1
- 150000001793 charged compounds Chemical class 0.000 description 1
- 238000005660 chlorination reaction Methods 0.000 description 1
- 235000012000 cholesterol Nutrition 0.000 description 1
- 239000000470 constituent Substances 0.000 description 1
- 208000026758 coronary atherosclerosis Diseases 0.000 description 1
- HHEAADYXPMHMCT-UHFFFAOYSA-N dpph Chemical compound [O-][N+](=O)C1=CC([N+](=O)[O-])=CC([N+]([O-])=O)=C1[N]N(C=1C=CC=CC=1)C1=CC=CC=C1 HHEAADYXPMHMCT-UHFFFAOYSA-N 0.000 description 1
- 239000003814 drug Substances 0.000 description 1
- 235000013399 edible fruits Nutrition 0.000 description 1
- 210000002615 epidermis Anatomy 0.000 description 1
- 229940030275 epigallocatechin gallate Drugs 0.000 description 1
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 1
- 238000002474 experimental method Methods 0.000 description 1
- 239000005417 food ingredient Substances 0.000 description 1
- 239000004519 grease Substances 0.000 description 1
- 230000036541 health Effects 0.000 description 1
- 235000001497 healthy food Nutrition 0.000 description 1
- 238000000338 in vitro Methods 0.000 description 1
- 239000004615 ingredient Substances 0.000 description 1
- JEIPFZHSYJVQDO-UHFFFAOYSA-N iron(III) oxide Inorganic materials O=[Fe]O[Fe]=O JEIPFZHSYJVQDO-UHFFFAOYSA-N 0.000 description 1
- 125000000959 isobutyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])* 0.000 description 1
- 239000002075 main ingredient Substances 0.000 description 1
- 238000001819 mass spectrum Methods 0.000 description 1
- 238000005259 measurement Methods 0.000 description 1
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 1
- 230000000116 mitigating effect Effects 0.000 description 1
- 239000000203 mixture Substances 0.000 description 1
- 239000003960 organic solvent Substances 0.000 description 1
- 230000000704 physical effect Effects 0.000 description 1
- 238000012805 post-processing Methods 0.000 description 1
- 230000001681 protective effect Effects 0.000 description 1
- 239000002994 raw material Substances 0.000 description 1
- 239000012925 reference material Substances 0.000 description 1
- 210000003491 skin Anatomy 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
- 238000010998 test method Methods 0.000 description 1
- 239000002023 wood Substances 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07J—STEROIDS
- C07J17/00—Normal steroids containing carbon, hydrogen, halogen or oxygen, having an oxygen-containing hetero ring not condensed with the cyclopenta(a)hydrophenanthrene skeleton
-
- A—HUMAN NECESSITIES
- A23—FOODS OR FOODSTUFFS; TREATMENT THEREOF, NOT COVERED BY OTHER CLASSES
- A23L—FOODS, FOODSTUFFS, OR NON-ALCOHOLIC BEVERAGES, NOT COVERED BY SUBCLASSES A21D OR A23B-A23J; THEIR PREPARATION OR TREATMENT, e.g. COOKING, MODIFICATION OF NUTRITIVE QUALITIES, PHYSICAL TREATMENT; PRESERVATION OF FOODS OR FOODSTUFFS, IN GENERAL
- A23L33/00—Modifying nutritive qualities of foods; Dietetic products; Preparation or treatment thereof
- A23L33/10—Modifying nutritive qualities of foods; Dietetic products; Preparation or treatment thereof using additives
- A23L33/105—Plant extracts, their artificial duplicates or their derivatives
- A23L33/11—Plant sterols or derivatives thereof, e.g. phytosterols
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P39/00—General protective or antinoxious agents
- A61P39/06—Free radical scavengers or antioxidants
-
- 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
- Life Sciences & Earth Sciences (AREA)
- Health & Medical Sciences (AREA)
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- General Health & Medical Sciences (AREA)
- Botany (AREA)
- Polymers & Plastics (AREA)
- Medicinal Chemistry (AREA)
- Engineering & Computer Science (AREA)
- Food Science & Technology (AREA)
- Mycology (AREA)
- Biochemistry (AREA)
- Toxicology (AREA)
- Chemical Kinetics & Catalysis (AREA)
- General Chemical & Material Sciences (AREA)
- Nutrition Science (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Pharmacology & Pharmacy (AREA)
- Animal Behavior & Ethology (AREA)
- Public Health (AREA)
- Veterinary Medicine (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Steroid Compounds (AREA)
Abstract
The invention discloses a kind of epigallocatechin stigmasterol functional molecular, which forms ester group by the hydroxyl of epigallocatechin and the carboxyl of stigmasterol succinic acid, and epigallocatechin is connect with stigmasterol.The invention also discloses preparation methods, comprising: protects epigallocatechin, is then coupled with stigmasterol succinic acid, then be deprotected to obtain epigallocatechin stigmasterol.Application the invention also discloses above-mentioned epigallocatechin stigmasterol functional molecular as antioxidant.Epigallocatechin stigmasterol of the invention has good antioxygenic property, has the wider scope of application, and preparation method is simple, can be used for industrialized production.
Description
Technical field
The invention belongs to functional food and healthy food field, and in particular to a kind of epigallocatechin stigmasterol function
Molecule and its preparation method and application.
Background technique
Stigmasterol is to be present in plant a kind of natural constituents.A large amount of zooperies and human clinical data show
Phytosterol has significant meaning for reducing blood middle cholesterol content, mitigating cardiovascular disease, is a kind of important health care food
Product ingredient.But free phytosterol dissolubility in grease is poor, limits its actual use range.Phytosterol and carboxylic acid
Phytosterin ester is formed after esterification, can obviously improve its solubility.The carbon chain lengths of fatty acid and the effect of saturation degree of fatty acid
To the fusing point of phytosterin ester and fat-soluble, by selecting the type of fatty acid to form the fusing point, fat-soluble of changeable sterol ester
Etc. physical properties, be suitable for different types of product.Phytosterin ester have specific ionization phytosterol preferably it is fat-soluble and
The effect of more efficient norcholesterol, which is that one kind is ideal, to be reduced serum cholesterol, prevents and treats coronary atherosclerosis
The cardiopathic functional food ingredient of class.
Polyphenol is a kind of polyhydroxy phenol substance being widely present in plant.They are in the leaf of plant, wood, skin, shell
With have certain content in pulp, higher plant polyphenol is contained in fruit, cereal epidermis.There is polyphenol excellent antioxygen to be turned into
With this is the basis of its all physiological activity.A large amount of internal and experiment in vitro and epidemiologic data show to eat a certain amount of
Plant polyphenol have prevention and inhibiting effect to disease.Polyphenol has anti arteriosclerosis, prevention and treatment of coronary heart disease and apoplexy etc. cardiovascular
Disease and anti-inflammatory, anti-allergic effects and antivirus action.Modern medicine study proves that many diseases such as histoorgan aging etc. are all
Related with superfluous free radical, polyphenol has the function of removing free radical, and the large biological molecule induced free radical damages
To protective effect.Epigallocatechin is main ingredient in green tea polyphenols, is the characteristic resources in China.Epi-nutgall catechu
Element has excellent antioxidant activity and a variety of physiological activity.It is carried out using combination epigallocatechin and phytosterol
Modified method, the advantages of both combining while the dissolubility for improving phytosterol and epigallocatechin, have extensively
Wealthy application prospect.
Summary of the invention
The present invention provides a kind of epigallocatechin stigmasterol functional molecular and preparation method thereof, the functional molecular
Fat-soluble antioxygenic property greatly improves.
The present invention provides a kind of fat-soluble antioxidant being made of above-mentioned functional molecular.
A kind of epigallocatechin stigmasterol functional molecular, shown in structure such as formula (I):
In the present invention, ester group is formed by the carboxyl of epigallocatechin and the hydroxyl of stigmasterol, by epigallocatechin gallate
Theine and stigmasterol are joined together to form phenols phytosterol, obtain novel epigallocatechin stigmasterol function point
Son realizes the combination of stigmasterol and epigallocatechin on a molecular scale, makes the functional molecular while possessing stigmasterol
With the physiological activity of epigallocatechin.
The preparation method of the epigallocatechin stigmasterol functional molecular, includes the following steps:
(1) epigallocatechin is protected using acid anhydrides, obtains the epigallocatechin of five acyl groups protection；
(2) stigmasterol is reacted with succinic anhydride, obtains stigmasterol succinic acid；
(3) the stigmasterol succinic acid that the epigallocatechin for the five acyl groups protection that step (1) obtains and (2) obtain carries out
Coupling reaction, the epigallocatechin stigmasterol protected；
(4) product for obtaining step (3) is deprotected, post-treated to obtain the epigallocatechin stigmasterol rouge
Soluble antioxidant.
Reaction process is as follows:
Wherein: R is selected from methyl, ethyl, isopropyl (or 2- propyl) etc..
The purity is high for the epigallocatechin stigmasterol functional molecular that the preparation method obtains has preferable anti-oxidant
Performance.Epigallocatechin is the main component in China's green tea polyphenols, and abundance, physiological activity is strong, and is easy to be inhaled
It receives.The stigmasterol is available on the market, and the mixture of sterling or various plants sterol can be used.
In the present invention, the sequence that step (1) and step (2) carry out can also first carry out step (2) without limitation, then carry out
Step (1) can be selected according to actual needs.
Preferably, epigallocatechin reacts in alkaline environment with acid anhydrides in step (1).Preferably, reaction
Alkali, preferably weak base, including but not limited to one of potassium carbonate, triethylamine etc. or a variety of are added in system.Since phenolic hydroxyl group is living
Property is stronger, in mild alkaline conditions, further ensures the phenolic hydroxyl group of epigallocatechin and acid anhydrides carries out selection and reacts, in turn
Realize the selective protection to phenolic hydroxyl group.
To further increase selective yield, preferably, acid anhydrides is acetic anhydride, propionic andydride or isobutyl in step (1)
One of acid anhydrides is a variety of.Further preferably one of propionic andydride or isobutyric anhydride or a variety of.Propionic andydride is different
Butyric anhydride activity is relatively low, and selectivity is more preferable.
Step (1), in step (2), reaction dissolvent is generally esterification common organic solvent, for example can be N,
N '-dimethyl formamide, acetone etc..
In step (1), the molar ratio of epigallocatechin and acid anhydrides is 1:(5~10).Further preferred molar ratio
For 1:(5~7).
In step (1), the molar ratio of epigallocatechin and alkali is 1:(5~10).Further preferred molar ratio is
1:(5~7).
Step (1) generally carries out at room temperature, naturally it is also possible to carry out appropriate heating operation etc. according to actual needs, react
Whether the time can completely determining according to real reaction, and generally 3~8 hours.After step (1) fully reacting, by simple water
Wash the dry reaction raw materials that can serve as step (3).
In step (2), in stigmasterol and succinic anhydride reaction system, generally addition acid binding agent, common acid binding agent include
K2CO3, triethylamine etc..
In step (2), the molar ratio of stigmasterol and succinic anhydride is 1:(1~5), further preferably 1:(2~4).Beans
The molar ratio of sterol and acid binding agent is 1:(1~5), further preferably 1:(2~3).
Step (2) generally carries out at room temperature, naturally it is also possible to carry out appropriate heating operation etc. according to actual needs, react
Time is generally 3~20 hours.
In step (3), the coupling reagent used in the coupling reaction is N, N'- dicyclohexylcarbodiimide or 1-
Ethyl-(3- dimethylaminopropyl) phosphinylidyne diimmonium salt hydrochlorate, as N preferably can be used, N'- dicyclohexylcarbodiimide is even
Joint-trial agent is cheap and easily-available, and has preferable effect to the coupling reaction between phenols and phytosterol.
Preferably, the mole that coupling reagent is added is 1~5 times of epigallocatechin mole, preferably
1.0-2.0 again.The mole that stigmasterol is added is 0.5~5 times, preferably 1.0-2.0 times of epigallocatechin mole.
Preferably, needing to be added catalyst 4-dimethylaminopyridine in coupling reaction, the mole that catalyst is added is
0.01-0.1 times of epigallocatechin mole, preferably 0.02-0.08.
In step (3), the solvent of reaction is methylene chloride, toluene or tetrahydrofuran.
In step (3), deprotecting regent uses hydrazine, for example can use hydrazine hydrate.
In step (4), the mole that deprotecting regent is added is 5~10 times of epigallocatechin mole.
Reaction of the invention can carry out at room temperature.
The present invention has the following advantages that relative to existing phytosterin ester and effect:
(1) epigallocatechin stigmasterol of the invention has good anti-oxidation function.
(2) epigallocatechin stigmasterol preparation efficiency of the invention is high, and reaction condition is mild, and post-processing is simple, fits
For industrialized production and application.
Specific embodiment
Below with reference to embodiment, the present invention is described in further detail, and embodiments of the present invention are not limited thereto.
Embodiment 1
Epigallocatechin (61.2mg, 0.2mmol) is dissolved in N, and propionic andydride is added dropwise in N '-dimethyl formamide (5ml)
(166.1 microlitres, 1.2mmol), triethylamine (166.1 microlitres, 1.2mmol) into mixed liquor, react about 4 hours, after water
It washes and is dried to obtain five propiono epigallocatechins.Stigmasterol (103.2mg, 0.25mmol), K2CO3(69.1mg,
0.5mmol), succinic anhydride (125.1mg, 0.75mmol) is dissolved in N, and in N '-dimethyl formamide (3ml) solvent, reaction 10 is small
When, after washing and drying obtain stigmasterol succinic acid.By five propiono epigallocatechins, stigmasterol succinic acid, N, N'-
Dicyclohexylcarbodiimide (49.0mg) and 4-dimethylaminopyridine (2.0mg) are stirred to react 2 hours in methylene chloride, then
50% hydrazine hydrate (60mg) is added and handles 1 hour to be extracted with ethyl acetate after reaction, table is obtained after chromatogram purification
Nutgall catechin stigmasterol (yield: 85%, purity 95%).
Structure determination data: nuclear magnetic data shows the characteristic peak of 5-8ppm catechin and the characteristic peak of 1-4ppm stigmasterol,
IR 1715cm-1Left and right display ester group characteristic absorption peak, mass spectrum show chlorination molecular ion peak 834.95.These data demonstrate
The correctness of synthetic structure.
Embodiment 2
Epigallocatechin (61.2mg, 0.2mmol) is dissolved in N, and propionic andydride is added dropwise in N '-dimethyl formamide (5ml)
(166.1 microlitres, 1.2mmol), triethylamine (166.1 microlitres, 1.2mmol) into mixed liquor, react about 4 hours, after water
It washes and is dried to obtain five propiono epigallocatechins.Stigmasterol (82.4mg, 0.2mmol), K2CO3(69.1mg, 0.5mmol),
Succinic anhydride (125.1mg, 0.75mmol) is dissolved in N, in N '-dimethyl formamide (3ml) solvent, reacts 10 hours, after
Washing and drying obtains stigmasterol succinic acid.By five propiono epigallocatechins, stigmasterol succinic acid, 1- ethyl-(3- diformazan
Base aminopropyl) that 2 are stirred to react in toluene is small for phosphinylidyne diimmonium salt hydrochlorate (46.0mg) and 4-dimethylaminopyridine (2.0mg)
When, 50% hydrazine hydrate (60mg) is then added and handles 1 hour to be extracted with ethyl acetate after reaction, after chromatogram purification
Obtain epigallocatechin stigmasterol (yield: 84%, purity 95%).Detection data is the same as embodiment 1.
Embodiment 3
Epigallocatechin (61.2mg, 0.2mmol) is dissolved in N, and propionic andydride is added dropwise in N '-dimethyl formamide (5ml)
(166.1 microlitres, 1.2mmol), triethylamine (166.1 microlitres, 1.2mmol) into mixed liquor, react about 4 hours, after water
It washes and is dried to obtain five propiono epigallocatechins.Stigmasterol (103.2mg, 0.25mmol), K2CO3(69.1mg,
0.5mmol), succinic anhydride (125.1mg, 0.75mmol) is dissolved in N, and in N '-dimethyl formamide (3ml) solvent, reaction 10 is small
When, after washing and drying obtain stigmasterol succinic acid.By five propiono epigallocatechins, stigmasterol succinic acid, 1- second
Base-(3- dimethylaminopropyl) phosphinylidyne diimmonium salt hydrochlorate (46.0mg) and 4-dimethylaminopyridine (2.0mg) are in tetrahydro furan
It is stirred to react in muttering 2 hours, 50% hydrazine hydrate (60mg) is then added and handles 1 hour to be extracted after reaction with ethyl acetate
It takes, epigallocatechin stigmasterol (yield: 86%, purity 95%) is obtained after chromatogram purification.The same embodiment of detection data
1。
Antioxidant activity test: DPPH free radical inhibitory effect progress antioxygenic property measurement (test method bibliography:
Food Chemistry 163 (2014) 171-177), wherein reference material has the stigmasterol before not being transformed, BHA (butylhydroxy fennel
Fragrant ether), BHT (2,6 di tert butyl 4 methyl phenol).Test result is as follows by inhibiting rate IC50 shown in table.
DPPH inhibiting rate IC50 antioxidant activity test result
| Stigmasterol | Epigallocatechin stigmasterol | BHA | BHT |
| Unrestraint activity | 23μM | 230μM | 256μM |
As seen from the above table, the antioxidant activity for the epigallocatechin stigmasterol that the present invention obtains obviously increases.
Claims (10)
1. a kind of epigallocatechin stigmasterol functional molecular, which is characterized in that shown in structure such as formula (I):
2. a kind of preparation method of epigallocatechin stigmasterol functional molecular as described in claim 1, which is characterized in that
Including following preparation step:
(1) epigallocatechin and anhydride reaction obtain the epigallocatechin of five acyl groups protection；
(2) stigmasterol is reacted with succinic anhydride, obtains stigmasterol succinic acid；
(3) the stigmasterol succinic acid that the epigallocatechin for the five acyl groups protection that step (1) obtains and step (2) obtain carries out
Coupling reaction, the epigallocatechin stigmasterol protected；
(4) product for obtaining step (3) is deprotected, post-treated to obtain the epigallocatechin stigmasterol function point
Son.
3. the preparation method of epigallocatechin stigmasterol functional molecular according to claim 2, which is characterized in that table
The molar ratio of nutgall catechin and acid anhydrides is 1:(5~10).
4. the preparation method of epigallocatechin stigmasterol functional molecular according to claim 2, which is characterized in that acid
Acid anhydride is propionic andydride or isobutyric anhydride.
5. the preparation method of epigallocatechin stigmasterol functional molecular according to claim 2, which is characterized in that institute
The coupling reagent for stating coupling reaction is N, N'- dicyclohexylcarbodiimide or 1- ethyl-(3- dimethylaminopropyl) phosphinylidyne
Diimmonium salt hydrochlorate.
6. the preparation method of epigallocatechin stigmasterol functional molecular according to claim 2, which is characterized in that institute
It states and needs to be added catalyst 4-dimethylaminopyridine in coupling reaction, the mole that catalyst is added is rubbed for epigallocatechin
0.01-0.5 times of that amount.
7. the preparation method of epigallocatechin stigmasterol functional molecular according to claim 2, which is characterized in that step
Suddenly the deprotecting regent in (4) uses hydrazine.
8. the preparation method of epigallocatechin stigmasterol functional molecular according to claim 2, which is characterized in that beans
The mole that sterol is added is 0.5~5 times of epigallocatechin mole.
9. the preparation method of epigallocatechin stigmasterol functional molecular according to claim 2, which is characterized in that even
The mole that joint-trial agent is added is 1~5 times of epigallocatechin mole.
10. a kind of fat-soluble antioxidant, which is characterized in that including epigallocatechin stigmasterol described in claim 1
Functional molecular.
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Citations (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US20140322340A1 (en) * | 2011-03-01 | 2014-10-30 | Technion Research And Development Foundation Ltd. | Protein-polysaccharide conjugates and use for encapsulating nutraceuticals for clear beverage applications |
| CN106565808A (en) * | 2016-10-21 | 2017-04-19 | 浙江大学 | Beta-sitosterol type catechinic acid liposolubility antioxidant and preparation method thereof |
| CN107973835A (en) * | 2016-10-21 | 2018-05-01 | 浙江大学 | Natural mixed phytosterin catechin, preparation method and application |
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2018
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| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US20140322340A1 (en) * | 2011-03-01 | 2014-10-30 | Technion Research And Development Foundation Ltd. | Protein-polysaccharide conjugates and use for encapsulating nutraceuticals for clear beverage applications |
| CN106565808A (en) * | 2016-10-21 | 2017-04-19 | 浙江大学 | Beta-sitosterol type catechinic acid liposolubility antioxidant and preparation method thereof |
| CN107973835A (en) * | 2016-10-21 | 2018-05-01 | 浙江大学 | Natural mixed phytosterin catechin, preparation method and application |
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