CN105837647B - Phenolic compound and its application - Google Patents
Phenolic compound and its application Download PDFInfo
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- CN105837647B CN105837647B CN201610208221.7A CN201610208221A CN105837647B CN 105837647 B CN105837647 B CN 105837647B CN 201610208221 A CN201610208221 A CN 201610208221A CN 105837647 B CN105837647 B CN 105837647B
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- 150000002989 phenols Chemical class 0.000 title claims abstract description 18
- 150000001875 compounds Chemical group 0.000 claims abstract description 28
- 240000000716 Durio zibethinus Species 0.000 claims description 10
- 235000006025 Durio zibethinus Nutrition 0.000 claims description 10
- 229940125904 compound 1 Drugs 0.000 claims description 10
- 239000000284 extract Substances 0.000 claims description 7
- 238000000605 extraction Methods 0.000 claims description 7
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims description 6
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 claims description 4
- 238000000034 method Methods 0.000 claims description 4
- 235000019441 ethanol Nutrition 0.000 claims description 3
- 239000002904 solvent Substances 0.000 claims description 3
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 3
- 238000004440 column chromatography Methods 0.000 claims description 2
- 239000000287 crude extract Substances 0.000 claims description 2
- 239000002024 ethyl acetate extract Substances 0.000 claims description 2
- 238000010438 heat treatment Methods 0.000 claims description 2
- 125000004836 hexamethylene group Chemical group [H]C([H])([*:2])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[*:1] 0.000 claims description 2
- 239000012535 impurity Substances 0.000 claims description 2
- 239000010410 layer Substances 0.000 claims description 2
- 239000012044 organic layer Substances 0.000 claims description 2
- 238000010992 reflux Methods 0.000 claims description 2
- 238000004007 reversed phase HPLC Methods 0.000 claims description 2
- 238000000926 separation method Methods 0.000 claims description 2
- 238000010898 silica gel chromatography Methods 0.000 claims description 2
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 claims 3
- 150000002148 esters Chemical class 0.000 claims 1
- 230000003110 anti-inflammatory effect Effects 0.000 abstract description 6
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 abstract description 5
- 229940124599 anti-inflammatory drug Drugs 0.000 abstract description 4
- 230000008901 benefit Effects 0.000 abstract description 4
- 231100000053 low toxicity Toxicity 0.000 abstract description 4
- 239000002260 anti-inflammatory agent Substances 0.000 abstract description 3
- 238000005160 1H NMR spectroscopy Methods 0.000 description 12
- 206010061218 Inflammation Diseases 0.000 description 12
- 230000004054 inflammatory process Effects 0.000 description 11
- 239000003814 drug Substances 0.000 description 9
- 239000000523 sample Substances 0.000 description 9
- 229940125782 compound 2 Drugs 0.000 description 8
- 229940079593 drug Drugs 0.000 description 8
- 229940126214 compound 3 Drugs 0.000 description 7
- 238000003919 heteronuclear multiple bond coherence Methods 0.000 description 7
- 230000002401 inhibitory effect Effects 0.000 description 7
- CGIGDMFJXJATDK-UHFFFAOYSA-N indomethacin Chemical compound CC1=C(CC(O)=O)C2=CC(OC)=CC=C2N1C(=O)C1=CC=C(Cl)C=C1 CGIGDMFJXJATDK-UHFFFAOYSA-N 0.000 description 6
- 238000001644 13C nuclear magnetic resonance spectroscopy Methods 0.000 description 5
- 239000002158 endotoxin Substances 0.000 description 5
- 229920006008 lipopolysaccharide Polymers 0.000 description 5
- 239000000126 substance Substances 0.000 description 5
- 238000002114 high-resolution electrospray ionisation mass spectrometry Methods 0.000 description 4
- WLAMNBDJUVNPJU-UHFFFAOYSA-N 2-methylbutyric acid Chemical compound CCC(C)C(O)=O WLAMNBDJUVNPJU-UHFFFAOYSA-N 0.000 description 3
- WQZGKKKJIJFFOK-GASJEMHNSA-N Glucose Natural products OC[C@H]1OC(O)[C@H](O)[C@@H](O)[C@@H]1O WQZGKKKJIJFFOK-GASJEMHNSA-N 0.000 description 3
- 239000002537 cosmetic Substances 0.000 description 3
- 238000001212 derivatisation Methods 0.000 description 3
- 230000000694 effects Effects 0.000 description 3
- 238000002474 experimental method Methods 0.000 description 3
- 230000036541 health Effects 0.000 description 3
- 238000003929 heteronuclear multiple quantum coherence Methods 0.000 description 3
- 229960000905 indomethacin Drugs 0.000 description 3
- 230000000638 stimulation Effects 0.000 description 3
- UAXOELSVPTZZQG-UHFFFAOYSA-N tiglic acid Natural products CC(C)=C(C)C(O)=O UAXOELSVPTZZQG-UHFFFAOYSA-N 0.000 description 3
- 238000001026 1H--1H correlation spectroscopy Methods 0.000 description 2
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 2
- IAZDPXIOMUYVGZ-WFGJKAKNSA-N Dimethyl sulfoxide Chemical compound [2H]C([2H])([2H])S(=O)C([2H])([2H])[2H] IAZDPXIOMUYVGZ-WFGJKAKNSA-N 0.000 description 2
- 241000196324 Embryophyta Species 0.000 description 2
- 241000219071 Malvaceae Species 0.000 description 2
- 125000001931 aliphatic group Chemical group 0.000 description 2
- 238000003556 assay Methods 0.000 description 2
- 229910052799 carbon Inorganic materials 0.000 description 2
- 230000010261 cell growth Effects 0.000 description 2
- 238000006243 chemical reaction Methods 0.000 description 2
- 239000003153 chemical reaction reagent Substances 0.000 description 2
- 230000008878 coupling Effects 0.000 description 2
- 238000010168 coupling process Methods 0.000 description 2
- 238000005859 coupling reaction Methods 0.000 description 2
- 239000013078 crystal Substances 0.000 description 2
- 230000007123 defense Effects 0.000 description 2
- 201000010099 disease Diseases 0.000 description 2
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 description 2
- 238000004817 gas chromatography Methods 0.000 description 2
- 230000009036 growth inhibition Effects 0.000 description 2
- 235000013402 health food Nutrition 0.000 description 2
- 208000015181 infectious disease Diseases 0.000 description 2
- 238000011081 inoculation Methods 0.000 description 2
- 229930014626 natural product Natural products 0.000 description 2
- WBYWAXJHAXSJNI-VOTSOKGWSA-M .beta-Phenylacrylic acid Natural products [O-]C(=O)\C=C\C1=CC=CC=C1 WBYWAXJHAXSJNI-VOTSOKGWSA-M 0.000 description 1
- 238000005084 2D-nuclear magnetic resonance Methods 0.000 description 1
- 208000024827 Alzheimer disease Diseases 0.000 description 1
- 206010008190 Cerebrovascular accident Diseases 0.000 description 1
- 206010008874 Chronic Fatigue Syndrome Diseases 0.000 description 1
- PQMOXTJVIYEOQL-UHFFFAOYSA-N Cumarin Natural products CC(C)=CCC1=C(O)C(C(=O)C(C)CC)=C(O)C2=C1OC(=O)C=C2CCC PQMOXTJVIYEOQL-UHFFFAOYSA-N 0.000 description 1
- 125000002353 D-glucosyl group Chemical group C1([C@H](O)[C@@H](O)[C@H](O)[C@H](O1)CO)* 0.000 description 1
- 241000934928 Durio Species 0.000 description 1
- 235000006026 Durio Nutrition 0.000 description 1
- 241000134253 Lanka Species 0.000 description 1
- FSOGIJPGPZWNGO-UHFFFAOYSA-N Meomammein Natural products CCC(C)C(=O)C1=C(O)C(CC=C(C)C)=C(O)C2=C1OC(=O)C=C2CCC FSOGIJPGPZWNGO-UHFFFAOYSA-N 0.000 description 1
- 208000019695 Migraine disease Diseases 0.000 description 1
- 240000002853 Nelumbo nucifera Species 0.000 description 1
- 235000006508 Nelumbo nucifera Nutrition 0.000 description 1
- 235000006510 Nelumbo pentapetala Nutrition 0.000 description 1
- 206010028980 Neoplasm Diseases 0.000 description 1
- 244000294611 Punica granatum Species 0.000 description 1
- 235000014360 Punica granatum Nutrition 0.000 description 1
- 206010039966 Senile dementia Diseases 0.000 description 1
- 208000006011 Stroke Diseases 0.000 description 1
- 238000010521 absorption reaction Methods 0.000 description 1
- 238000005903 acid hydrolysis reaction Methods 0.000 description 1
- 239000003963 antioxidant agent Substances 0.000 description 1
- 230000003078 antioxidant effect Effects 0.000 description 1
- 235000006708 antioxidants Nutrition 0.000 description 1
- 238000013459 approach Methods 0.000 description 1
- 210000001367 artery Anatomy 0.000 description 1
- 208000006673 asthma Diseases 0.000 description 1
- 230000009286 beneficial effect Effects 0.000 description 1
- 150000001555 benzenes Chemical group 0.000 description 1
- WQZGKKKJIJFFOK-VFUOTHLCSA-N beta-D-glucose Chemical compound OC[C@H]1O[C@@H](O)[C@H](O)[C@@H](O)[C@@H]1O WQZGKKKJIJFFOK-VFUOTHLCSA-N 0.000 description 1
- 230000004071 biological effect Effects 0.000 description 1
- 230000015572 biosynthetic process Effects 0.000 description 1
- 201000011510 cancer Diseases 0.000 description 1
- 238000004113 cell culture Methods 0.000 description 1
- 230000007541 cellular toxicity Effects 0.000 description 1
- 230000008859 change Effects 0.000 description 1
- 238000004587 chromatography analysis Methods 0.000 description 1
- 239000013068 control sample Substances 0.000 description 1
- ZYGHJZDHTFUPRJ-UHFFFAOYSA-N coumarin Chemical compound C1=CC=C2OC(=O)C=CC2=C1 ZYGHJZDHTFUPRJ-UHFFFAOYSA-N 0.000 description 1
- 239000012531 culture fluid Substances 0.000 description 1
- 206010012601 diabetes mellitus Diseases 0.000 description 1
- 238000009510 drug design Methods 0.000 description 1
- 230000004064 dysfunction Effects 0.000 description 1
- 235000013399 edible fruits Nutrition 0.000 description 1
- 230000007613 environmental effect Effects 0.000 description 1
- XYIBRDXRRQCHLP-UHFFFAOYSA-N ethyl acetoacetate Chemical compound CCOC(=O)CC(C)=O XYIBRDXRRQCHLP-UHFFFAOYSA-N 0.000 description 1
- 235000013305 food Nutrition 0.000 description 1
- 239000012634 fragment Substances 0.000 description 1
- 239000008103 glucose Substances 0.000 description 1
- 208000019622 heart disease Diseases 0.000 description 1
- 238000004128 high performance liquid chromatography Methods 0.000 description 1
- 125000004435 hydrogen atom Chemical group [H]* 0.000 description 1
- 230000007062 hydrolysis Effects 0.000 description 1
- 238000006460 hydrolysis reaction Methods 0.000 description 1
- 125000002887 hydroxy group Chemical group [H]O* 0.000 description 1
- -1 iginates Species 0.000 description 1
- 230000006872 improvement Effects 0.000 description 1
- 230000002458 infectious effect Effects 0.000 description 1
- 230000001524 infective effect Effects 0.000 description 1
- 230000002757 inflammatory effect Effects 0.000 description 1
- 210000000936 intestine Anatomy 0.000 description 1
- 150000002611 lead compounds Chemical class 0.000 description 1
- 238000005259 measurement Methods 0.000 description 1
- 239000000203 mixture Substances 0.000 description 1
- 238000012986 modification Methods 0.000 description 1
- 230000004048 modification Effects 0.000 description 1
- 208000029766 myalgic encephalomeyelitis/chronic fatigue syndrome Diseases 0.000 description 1
- 239000002547 new drug Substances 0.000 description 1
- 230000000050 nutritive effect Effects 0.000 description 1
- 238000000238 one-dimensional nuclear magnetic resonance spectroscopy Methods 0.000 description 1
- 201000008482 osteoarthritis Diseases 0.000 description 1
- 201000001245 periodontitis Diseases 0.000 description 1
- 230000000144 pharmacologic effect Effects 0.000 description 1
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 1
- 239000000843 powder Substances 0.000 description 1
- 239000002243 precursor Substances 0.000 description 1
- 230000002265 prevention Effects 0.000 description 1
- 230000008569 process Effects 0.000 description 1
- 238000011160 research Methods 0.000 description 1
- 238000012827 research and development Methods 0.000 description 1
- 238000004611 spectroscopical analysis Methods 0.000 description 1
- 238000001228 spectrum Methods 0.000 description 1
- 238000006467 substitution reaction Methods 0.000 description 1
- 208000011580 syndromic disease Diseases 0.000 description 1
- 238000003786 synthesis reaction Methods 0.000 description 1
- 238000012360 testing method Methods 0.000 description 1
- 231100000820 toxicity test Toxicity 0.000 description 1
- WBYWAXJHAXSJNI-VOTSOKGWSA-N trans-cinnamic acid Chemical compound OC(=O)\C=C\C1=CC=CC=C1 WBYWAXJHAXSJNI-VOTSOKGWSA-N 0.000 description 1
- 230000002792 vascular Effects 0.000 description 1
- 210000003462 vein Anatomy 0.000 description 1
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
- C07H17/075—Benzo[b]pyran-2-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
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07H—SUGARS; DERIVATIVES THEREOF; NUCLEOSIDES; NUCLEOTIDES; NUCLEIC ACIDS
- C07H15/00—Compounds containing hydrocarbon or substituted hydrocarbon radicals directly attached to hetero atoms of saccharide radicals
- C07H15/20—Carbocyclic rings
- C07H15/203—Monocyclic carbocyclic rings other than cyclohexane rings; Bicyclic carbocyclic ring systems
-
- 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)
- Veterinary Medicine (AREA)
- Engineering & Computer Science (AREA)
- Animal Behavior & Ethology (AREA)
- Public Health (AREA)
- Dermatology (AREA)
- Birds (AREA)
- Epidemiology (AREA)
- Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Medicines Containing Plant Substances (AREA)
Abstract
The invention discloses a kind of phenolic compound and its application, compound structure isWherein R isWherein R1、R2For H, OH ,-O-CH3、‑O‑CH3‑CH3Or-O-CH3‑CH3‑CH3.Phenolic compound of the invention has good anti-inflammatory effect, has the advantages that efficient, low toxicity, and being expected to exploitation is new anti-inflammatory drug.
Description
Technical field
The invention belongs to medicine and field of health care food, and in particular to a kind of phenolic compound and its application.
Background technique
Inflammation (inflammation): the living tissue defense reaction that damage factor is occurred with vascular system is
Inflammation.It is a kind of defense reaction of the body for stimulation, shows as red, swollen, hot, pain and dysfunction.Inflammation can be sense
Infective inflammation caused by contaminating, non-infectious inflammation caused by may not be due to infection.
Inflammation is common disease, affects our health in all respects.A series of medical research shows inflammation and moves
Arteries and veins hardening, heart disease, apoplexy, cancer, diabetes, senile dementia, periodontitis, osteoarthritis, asthma, migraines, intestines easily swash
Syndrome, chronic fatigue syndrome etc. are all closely related.It can be seen that inflammatory effect entire body.
The drug that natural drug especially derives from plant has chemical structure diversity and diverse biological activities, always
It is the main source that the mankind prevent and treat disease.The many drugs clinically applied all directly or indirectly are produced from natural
Object, natural products act not only as the semi-synthetic precursor of drug, and can be used as the template of pharmaceutical chemistry synthesis, are
New drug design provides new approaches.Natural products has become discovery one of novel drugs or the main source of lead compound.
Durian (Durio zibethinus Murr.) is Bombacaceae (Bombacaceae) durian genus (Durio) plant.Pomegranate
Lotus originates in Malaysia, and being passed to states, the China Hainans such as Philippine, Sri Lanka, Thailand, Vietnam and Burma afterwards also has a small amount of cultivation
Kind.Durian has nutritive value abundant, referred to as Asia " king of fruit ".Traditional pharmacology is studies have shown that durian can be alleviated
The elderly's pruitus also has some improvement for dysmenorrhes.Modern pharmacology Effect study shows that durian ethyl alcohol is thick
Extract has anti-oxidant and anti-inflammatory effect.Durian chemical constitution study is less, thus its chemical component be worth further research and
Development and utilization.Meanwhile durian pericarp is in most cases treated as organic garbage treatment, so the present invention has in environmental protection
Certain value.
Summary of the invention
The purpose of the present invention is to provide a kind of phenolic compounds.
The purpose of the present invention is to provide application of the above-mentioned phenolic compound in inflammation prevention and treatment.
The technical solution used in the present invention is:
Phenolic compound, general structure are as follows:
Wherein R is
Further, the R1For H, OH ,-O-CH3、-O-CH3-CH3Or-O-CH3-CH3-CH3。
Further, the R2For H, OH ,-O-CH3、-O-CH3-CH3Or-O-CH3-CH3-CH3。
Further, the R1For-O-CH3。
Further, the R2For-O-CH3。
Above-mentioned phenolic compound application in preparing anti-inflammatory drugs.
Above-mentioned phenolic compound is preparing the application in anti-inflammatory health product.
Above-mentioned phenolic compound is preparing the application in anti-inflammatory cosmetics.
The beneficial effects of the present invention are:
Phenolic compound of the invention has preferable anti-inflammatory effect to mouse RAW264.7 cell, which has height
The advantage of effect, low toxicity, being expected to exploitation is new anti-inflammatory drug；Or it is used to prepare the health food for preventing and treating inflammation and change
Cosmetic.
Detailed description of the invention
Fig. 1 is the compounds of this invention 11H-NMR map；
Fig. 2 is the compounds of this invention 113C-NMR map；
Fig. 3 is the HMQC map of the compounds of this invention 1；
Fig. 4 is the HMBC map of the compounds of this invention 1；
Fig. 5 is the compounds of this invention 11H-1H COSY map；
Fig. 6 is the compounds of this invention 21H-NMR map；
Fig. 7 is the HMBC map of the compounds of this invention 2；
Fig. 8 is the compounds of this invention 31H-NMR map；
Fig. 9 is the HMBC map of the compounds of this invention 3.
Specific embodiment
The present invention is further illustrated combined with specific embodiments below, and however, it is not limited to this.
The extraction of 1 phenolic compound of embodiment
1) durian pericarp 20kg is taken, with 70% ethyl alcohol heating and refluxing extraction 5 times, 3 hours every time, combined extract was depressurized back
Solvent is received, total medicinal extract is obtained；
2) total medicinal extract is suspended with water, with hexamethylene equal-volume extraction 4 times, oil-soluble impurities is removed, then through chloroform, second
Acetoacetic ester equal-volume extraction 5 times, organic layer is evaporated under reduced pressure to obtain crude extract.
3) ethyl acetate extract layer 50g is taken, by using silica gel column chromatography, ODS medium and low pressure column chromatography, RP-HPLC
The separation methods such as chromatography, isolated the compounds of this invention 2 and 3.
The present invention by physicochemical constant and Modern spectroscopy technological means (HR-ESI-MS, 1D-NMR, 2D-NMR) identify with
The structure of upper 3 compounds, compound 1 are Durianol A, and compound 2 is Durianol B, and compound 3 is Durianol
The Structural Identification process of C, compound 1~3 are as described below.
The identification of 2 phenolic compound of embodiment
(1) identification of compound 1 (Durianol A)
Compound 1 is white amorphous powder；Its HR-ESI-MS m/z 461.1407 [M+Na]+(calcd.for
C21H26O10, 461.1424), determine that molecular formula is C20H18O9.?1In H-NMR (Fig. 1), chemical shift δH6.32 and δH 7.95
Thus the proton signal to intercouple for one group, coupling constant 9.5Hz speculate and contain cumarin parent nucleus in structure.Meanwhile hydrogen
Proton signal and one group of aliphatic chain proton signal containing one group of sugar in spectrum, in conjunction with13C-NMR (Fig. 2) can further verify knot
Structure speculates.Compound passes through sour water solution, and sugar is derivative, GC analysis, determines that sugar is D-Glucose.Compound planar structure is through HMQC
(Fig. 3), HMBC (Fig. 4) and1H-1H COSY (Fig. 5) can be further confirmed that.Believe with the aliphatic chain that hydroxyl is connected on sugared six carbon
Number it is determined as the segment of 2-Methyl Butyric Acid through HMQC and HMBC, compound is by hydrolysis, derivatization, with standard items S-2- methyl fourth
Sour derivatization product is determined as S-2- methylbutanoic acid through HPLC analysis of control.Thus compound is confirmed as Durianol A,
Structure is shown in Table 1, and nuclear magnetic data is shown in Table 2.
(2) identification of compound 2 (Durianol B)
Compound 2 is white needle-like crystals；Its HR-ESI-MS m/z 437.1443 [M+Na]+(calcd.for
C19H26O10, 437.1424), determine that molecular formula is C19H26O10.?1In H-NMR (Fig. 6), the proton signal and chemical combination of high field region
Object 1 is consistent, thus speculates in compound 2 and contains 2-Methyl Butyric Acid, absolute configuration is determined as S- configuration through same method.Simultaneously
?1In H-NMR, it can clearly be seen that one group 1, the proton signal of 3,4 trisubstituted benzene rings.Compound Sugar signal, also passes through acid
Hydrolysis, derivatization, GC analysis are determined as D-Glucose.Three structure fragments find corresponding connection position through HMBC spectrogram (Fig. 7)
It sets.Compound is confirmed as Durianol B, and structure is shown in Table 1, compound 21H-NMR and13C-NMR data are shown in Table 2.
(3) identification of compound 3 (Durianol C)
Compound 3 is white plates crystal；Its HR-ESI-MS m/z 411.1684 [M+H]+(calcd.for
C20H26O9, 411.1655), determine that molecular formula is C20H26O9.With compound 21H-NMR compares, discovery compound 31H-NMR
The proton signal of (Fig. 8) only has difference in fragrant area, therefore speculates the segment containing glucose and 2-Methyl Butyric Acid in compound
Signal.?1In H-NMR, there is one group of proton signal to intercouple in fragrant area, is speculated as according to coupling constant and peak integral area
Two groups of symmetrical proton signals after contraposition replaces on phenyl ring are composed, thus it is speculated that the segment containing a trans-cinnamic acid in conjunction with carbon.By
HMBC spectrogram (Fig. 9) obtains the link position of three segments, determines that compound is Durianol C.Its structure is shown in Table 1, compound
31H-NMR and13C-NMR data are shown in Table 2.
The structure of 3 compounds of the invention of table 1
3 compounds of the invention of table 21H-NMR and13C-NMR data (DMSO-d6)
The compound 1~3 for extracting identification to the present invention below is made further pharmacological activity and is detected.
Cell toxicity test
Experimental method: mtt assay
By mouse RAW264.7 cell inoculation in 96 orifice plates, sample to be tested is added in culture afterwards for 24 hours, after being further cultured for 48h
The inhibiting rate that cell is grown with mtt assay measurement sample.Inhibitory rate of cell growth is according to the following formula, and soft with CalcuSyn
Part calculates the half-inhibitory concentration (IC of tested sample50)
Inhibitory rate of cell growth (%)=[(blank control-sample sets)/blank control] × 100%.
Experimental result is shown in Table 3
Table 3: growth inhibition effect of the compounds of this invention to mouse RAW264.7 cell
| Sample ID | Half-inhibitory concentration IC50(μM) |
| Compound 1 | >50.00 |
| Compound 2 | >50.00 |
| Compound 3 | >50.00 |
Experimental result: from the experimental data of table 3 it is found that the growth inhibition of 1~3 pair of mouse RAW264.7 cell of compound is made
With small, IC50Value is all larger than 50.00 μM, illustrates that phenolic compound 1~3 of the present invention has the advantages that low toxicity.
Anti-inflammation test
Experimental method: by RAW264.7 cell inoculation in 96 orifice plates, LPS (lipopolysaccharides) is added afterwards for 24 hours in culture.Then not
The sample (the compounds of this invention 1~3, positive drug Indomethacin) of various concentration, the bodies such as blank group addition are separately added into group
Product solvent.50 μ L cell culture fluids mix isometric Griess reagent I and 96 orifice plates of appeal are added, and are subsequently added into Griess
reagent II.Microplate reader measures absorption value of each group sample under 546nm wavelength, brings following formula into and calculates NO inhibiting rate,
And half-inhibitory concentration (the IC of tested sample is calculated with CalcuSyn software50)。
NO inhibiting rate (%)=[1- (sample sets/blank group)] × 100%.
4 the compounds of this invention of table, 1~3 couple of LPS stimulation cell RAW264.7 generates the inhibiting effect of NO
| Sample ID | Half-inhibitory concentration IC50(μM) |
| Compound 1 | 36.32±1.39 |
| Compound 2 | 38.07±2.40 |
| Compound 3 | 41.26±0.44 |
| Positive drug (Indomethacin) | 47.40±4.50 |
Experimental result: from the experimental data of table 4 it is found that 1~3 couple of lipopolysaccharides LPS stimulation mouse RAW264.7 of compound is thin
Born of the same parents, which generate NO, has good inhibiting effect, half-inhibitory concentration IC50Respectively 36.32 ± 1.39 μM, 38.07 ± 2.40 μ
M, 41.26 ± 0.44 μM, 47.40 ± 4.50 μM of positive drug Indomethacin are superior to.Illustrate phenolic compound of the present invention 1~
3 have preferable anti-inflammatory effect.
In conjunction with the above experiment and its experimental result, show that phenolic compound 1~3 of the present invention has the advantages that efficient, low toxicity,
Being expected to exploitation is new anti-inflammatory drug；Or it is used to prepare the health food and cosmetics for preventing and treating inflammation.
The above embodiment is a preferred embodiment of the present invention, but embodiments of the present invention are not by above-described embodiment
Limitation, other any changes, modifications, substitutions, combinations, simplifications made without departing from the spirit and principles of the present invention,
It should be equivalent substitute mode, be included within the scope of the present invention.
Claims (1)
1. a kind of extracting method of phenolic compound, which comprises the following steps:
1) 20 kg of durian pericarp is taken, with 70% ethyl alcohol heating and refluxing extraction 5 times, 3 hours every time, combined extract was recovered under reduced pressure
Solvent obtains total medicinal extract；
2) total medicinal extract is suspended with water, with hexamethylene equal-volume extraction 4 times, oil-soluble impurities is removed, then through chloroform, acetic acid second
Ester equal-volume extraction 5 times, organic layer is evaporated under reduced pressure to obtain crude extract；
3) ethyl acetate extract layer 50g is taken, by using silica gel column chromatography, ODS medium and low pressure column chromatography, reversed-phase high performance liquid chromatography
Separation method, isolated compound 1,2 and 3；
The structure of compound 1 ~ 3 respectively is、、。
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| WO2014102546A1 (en) * | 2012-12-24 | 2014-07-03 | Provexis Natural Products Limited | Compositions |
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