CN107365336A - A kind of noval chemical compound extracted from Guava Leaf, preparation method and its usage - Google Patents
A kind of noval chemical compound extracted from Guava Leaf, preparation method and its usage Download PDFInfo
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- CN107365336A CN107365336A CN201710615268.XA CN201710615268A CN107365336A CN 107365336 A CN107365336 A CN 107365336A CN 201710615268 A CN201710615268 A CN 201710615268A CN 107365336 A CN107365336 A CN 107365336A
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- 150000001875 compounds Chemical class 0.000 title claims abstract description 45
- 241000508269 Psidium Species 0.000 title claims abstract description 24
- 238000002360 preparation method Methods 0.000 title claims description 11
- 230000002218 hypoglycaemic effect Effects 0.000 claims abstract description 13
- 238000004809 thin layer chromatography Methods 0.000 claims abstract description 10
- 238000010898 silica gel chromatography Methods 0.000 claims abstract description 6
- 239000000126 substance Substances 0.000 claims abstract description 5
- 241000219094 Vitaceae Species 0.000 claims abstract description 4
- 230000000118 anti-neoplastic effect Effects 0.000 claims abstract description 4
- 239000012965 benzophenone Substances 0.000 claims abstract description 4
- 235000021021 grapes Nutrition 0.000 claims abstract description 4
- 150000003214 pyranose derivatives Chemical class 0.000 claims abstract description 4
- 238000000926 separation method Methods 0.000 claims abstract description 4
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 claims description 37
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 claims description 24
- 239000000284 extract Substances 0.000 claims description 24
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 claims description 21
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 claims description 14
- 238000010828 elution Methods 0.000 claims description 12
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 11
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims description 10
- 230000000259 anti-tumor effect Effects 0.000 claims description 8
- 229910052799 carbon Inorganic materials 0.000 claims description 8
- 239000000203 mixture Substances 0.000 claims description 8
- 239000003208 petroleum Substances 0.000 claims description 7
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 claims description 6
- 239000003480 eluent Substances 0.000 claims description 6
- 239000000741 silica gel Substances 0.000 claims description 6
- 229910002027 silica gel Inorganic materials 0.000 claims description 6
- 238000001514 detection method Methods 0.000 claims description 4
- 239000007788 liquid Substances 0.000 claims description 3
- 238000007445 Chromatographic isolation Methods 0.000 claims description 2
- 238000004458 analytical method Methods 0.000 claims description 2
- 238000011097 chromatography purification Methods 0.000 claims description 2
- 238000013461 design Methods 0.000 claims description 2
- 239000002024 ethyl acetate extract Substances 0.000 claims description 2
- 235000013376 functional food Nutrition 0.000 claims description 2
- 239000002994 raw material Substances 0.000 claims description 2
- 238000004064 recycling Methods 0.000 claims description 2
- XYIBRDXRRQCHLP-UHFFFAOYSA-N ethyl acetoacetate Chemical compound CCOC(=O)CC(C)=O XYIBRDXRRQCHLP-UHFFFAOYSA-N 0.000 claims 1
- 235000013402 health food Nutrition 0.000 claims 1
- 238000004440 column chromatography Methods 0.000 abstract description 5
- 238000000605 extraction Methods 0.000 abstract description 5
- RWCCWEUUXYIKHB-UHFFFAOYSA-N benzophenone Chemical compound C=1C=CC=CC=1C(=O)C1=CC=CC=C1 RWCCWEUUXYIKHB-UHFFFAOYSA-N 0.000 abstract 1
- 238000002425 crystallisation Methods 0.000 abstract 1
- 230000008025 crystallization Effects 0.000 abstract 1
- 125000000118 dimethyl group Chemical group [H]C([H])([H])* 0.000 abstract 1
- IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 18
- 210000004027 cell Anatomy 0.000 description 11
- 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 10
- 239000008103 glucose Substances 0.000 description 10
- 206010009944 Colon cancer Diseases 0.000 description 6
- 208000029742 colonic neoplasm Diseases 0.000 description 6
- 230000002401 inhibitory effect Effects 0.000 description 6
- 239000003814 drug Substances 0.000 description 5
- 230000004190 glucose uptake Effects 0.000 description 5
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 4
- 239000012980 RPMI-1640 medium Substances 0.000 description 4
- 238000006243 chemical reaction Methods 0.000 description 4
- 239000002609 medium Substances 0.000 description 4
- 229960001866 silicon dioxide Drugs 0.000 description 4
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 3
- 210000001789 adipocyte Anatomy 0.000 description 3
- 235000013305 food Nutrition 0.000 description 3
- 238000003919 heteronuclear multiple bond coherence Methods 0.000 description 3
- 229910052739 hydrogen Inorganic materials 0.000 description 3
- 239000001257 hydrogen Substances 0.000 description 3
- 239000000178 monomer Substances 0.000 description 3
- 238000001228 spectrum Methods 0.000 description 3
- 241000196324 Embryophyta Species 0.000 description 2
- 241000219926 Myrtaceae Species 0.000 description 2
- UCTWMZQNUQWSLP-UHFFFAOYSA-N adrenaline Chemical compound CNCC(O)C1=CC=C(O)C(O)=C1 UCTWMZQNUQWSLP-UHFFFAOYSA-N 0.000 description 2
- 239000008280 blood Substances 0.000 description 2
- 210000004369 blood Anatomy 0.000 description 2
- 239000007853 buffer solution Substances 0.000 description 2
- 230000001461 cytolytic effect Effects 0.000 description 2
- 235000013399 edible fruits Nutrition 0.000 description 2
- 238000002474 experimental method Methods 0.000 description 2
- 150000004676 glycans Chemical class 0.000 description 2
- 229930192048 guavinoside Natural products 0.000 description 2
- 238000000338 in vitro Methods 0.000 description 2
- 238000000034 method Methods 0.000 description 2
- 239000000843 powder Substances 0.000 description 2
- 239000000047 product Substances 0.000 description 2
- 239000012488 sample solution Substances 0.000 description 2
- 239000006228 supernatant Substances 0.000 description 2
- 238000012360 testing method Methods 0.000 description 2
- 239000004215 Carbon black (E152) Substances 0.000 description 1
- 235000001808 Ceanothus spinosus Nutrition 0.000 description 1
- 241001264786 Ceanothus spinosus Species 0.000 description 1
- 241001269238 Data Species 0.000 description 1
- 108090000790 Enzymes Proteins 0.000 description 1
- 102000004190 Enzymes Human genes 0.000 description 1
- 241000287828 Gallus gallus Species 0.000 description 1
- 239000004366 Glucose oxidase Substances 0.000 description 1
- 108010015776 Glucose oxidase Proteins 0.000 description 1
- 208000001953 Hypotension Diseases 0.000 description 1
- 229910021578 Iron(III) chloride Inorganic materials 0.000 description 1
- 206010028980 Neoplasm Diseases 0.000 description 1
- 240000001679 Psidium guajava Species 0.000 description 1
- 235000013929 Psidium pyriferum Nutrition 0.000 description 1
- 235000014220 Rhus chinensis Nutrition 0.000 description 1
- 240000003152 Rhus chinensis Species 0.000 description 1
- OHVGNSMTLSKTGN-BTVCFUMJSA-N [C].OC[C@@H](O)[C@@H](O)[C@H](O)[C@@H](O)C=O Chemical group [C].OC[C@@H](O)[C@@H](O)[C@H](O)[C@@H](O)C=O OHVGNSMTLSKTGN-BTVCFUMJSA-N 0.000 description 1
- 210000001015 abdomen Anatomy 0.000 description 1
- 238000010521 absorption reaction Methods 0.000 description 1
- PBCJIPOGFJYBJE-UHFFFAOYSA-N acetonitrile;hydrate Chemical compound O.CC#N PBCJIPOGFJYBJE-UHFFFAOYSA-N 0.000 description 1
- 125000002252 acyl group Chemical group 0.000 description 1
- 210000000593 adipose tissue white Anatomy 0.000 description 1
- -1 anti diar rhea Substances 0.000 description 1
- 230000001142 anti-diarrhea Effects 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
- 230000037429 base substitution Effects 0.000 description 1
- 230000003115 biocidal effect Effects 0.000 description 1
- 210000004204 blood vessel Anatomy 0.000 description 1
- 238000004364 calculation method Methods 0.000 description 1
- 238000004113 cell culture Methods 0.000 description 1
- 230000010261 cell growth Effects 0.000 description 1
- 239000006285 cell suspension Substances 0.000 description 1
- 230000000052 comparative effect Effects 0.000 description 1
- 235000009508 confectionery Nutrition 0.000 description 1
- 239000013078 crystal Substances 0.000 description 1
- 230000003013 cytotoxicity Effects 0.000 description 1
- 231100000135 cytotoxicity Toxicity 0.000 description 1
- 206010012601 diabetes mellitus Diseases 0.000 description 1
- VILAVOFMIJHSJA-UHFFFAOYSA-N dicarbon monoxide Chemical compound [C]=C=O VILAVOFMIJHSJA-UHFFFAOYSA-N 0.000 description 1
- 150000004141 diterpene derivatives Chemical class 0.000 description 1
- 238000002330 electrospray ionisation mass spectrometry Methods 0.000 description 1
- 238000005516 engineering process Methods 0.000 description 1
- 229940088598 enzyme Drugs 0.000 description 1
- 238000001976 enzyme digestion Methods 0.000 description 1
- 210000000918 epididymis Anatomy 0.000 description 1
- 201000010063 epididymitis Diseases 0.000 description 1
- 229930003935 flavonoid Natural products 0.000 description 1
- 150000002215 flavonoids Chemical class 0.000 description 1
- 235000017173 flavonoids Nutrition 0.000 description 1
- 239000002778 food additive Substances 0.000 description 1
- 229940116332 glucose oxidase Drugs 0.000 description 1
- 235000019420 glucose oxidase Nutrition 0.000 description 1
- 230000012010 growth Effects 0.000 description 1
- 238000005570 heteronuclear single quantum coherence Methods 0.000 description 1
- 229930195733 hydrocarbon Natural products 0.000 description 1
- 150000002430 hydrocarbons Chemical class 0.000 description 1
- 125000004435 hydrogen atom Chemical group [H]* 0.000 description 1
- 208000021822 hypotensive Diseases 0.000 description 1
- 230000001077 hypotensive effect Effects 0.000 description 1
- 230000005764 inhibitory process Effects 0.000 description 1
- RBTARNINKXHZNM-UHFFFAOYSA-K iron trichloride Chemical compound Cl[Fe](Cl)Cl RBTARNINKXHZNM-UHFFFAOYSA-K 0.000 description 1
- 230000031700 light absorption Effects 0.000 description 1
- 238000004519 manufacturing process Methods 0.000 description 1
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 1
- 238000002156 mixing Methods 0.000 description 1
- 239000013642 negative control Substances 0.000 description 1
- 231100000252 nontoxic Toxicity 0.000 description 1
- 230000003000 nontoxic effect Effects 0.000 description 1
- 230000000144 pharmacologic effect Effects 0.000 description 1
- 150000002989 phenols Chemical class 0.000 description 1
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 1
- 229960001553 phloroglucinol Drugs 0.000 description 1
- 229920001282 polysaccharide Polymers 0.000 description 1
- 239000005017 polysaccharide Substances 0.000 description 1
- 238000012545 processing Methods 0.000 description 1
- 239000000523 sample Substances 0.000 description 1
- 229920006395 saturated elastomer Polymers 0.000 description 1
- 239000000243 solution Substances 0.000 description 1
- 150000003505 terpenes Chemical class 0.000 description 1
- 235000007586 terpenes Nutrition 0.000 description 1
- 231100000419 toxicity Toxicity 0.000 description 1
- 230000001988 toxicity Effects 0.000 description 1
- 150000003648 triterpenes Chemical class 0.000 description 1
- 239000000341 volatile oil Substances 0.000 description 1
- 238000005406 washing Methods 0.000 description 1
Classifications
-
- 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
- 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
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07H—SUGARS; DERIVATIVES THEREOF; NUCLEOSIDES; NUCLEOTIDES; NUCLEIC ACIDS
- C07H1/00—Processes for the preparation of sugar derivatives
- C07H1/06—Separation; Purification
- C07H1/08—Separation; Purification from natural products
-
- 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
- Chemical & Material Sciences (AREA)
- Life Sciences & Earth Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- Engineering & Computer Science (AREA)
- Molecular Biology (AREA)
- General Health & Medical Sciences (AREA)
- Genetics & Genomics (AREA)
- Biotechnology (AREA)
- Biochemistry (AREA)
- Botany (AREA)
- Mycology (AREA)
- Nutrition Science (AREA)
- Food Science & Technology (AREA)
- Polymers & Plastics (AREA)
- Medicines Containing Plant Substances (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Abstract
The present invention relates to a kind of noval chemical compound isolated from Guava Leaf, chemical name is：The O of 3,52,4 dimethyl of dihydroxy 1 (6 ' O galloyl l β D grapes pyranose) benzophenone, structural formula are：The compound is passed through obtained by extraction, extraction, silica gel column chromatography, medium pressure column chromatography, thin-layer chromatography and Crystallization Separation, through cytoactive it is demonstrated experimentally that the compound has hypoglycemic and antineoplastic action by Guava Leaf.
Description
Technical field
The present invention relates to food, biomedicine field, more particularly to a kind of noval chemical compound isolated from Guava Leaf
And preparation method and purposes.
Background technology
Guava（Psidium guajava Linn.）It is commonly called as pulling out son, chicken arrow fruit, fragrant plant pleasure, red heart sweet, loudspeaker fruit etc., is
Myrtaceae（Myrtaceae）Psidium plant, originates in America, and the tropical and Asia for being distributed widely in America, Asia etc. is hot
Band area, there is larger cultivated area in each provinces and regions of south China such as area such as Guangdong, Guangxi.Guava Leaf is containing flavonoids, more
The functional active components such as phenols, triterpenes, miscellaneous source terpene, volatile oil and polysaccharide, it is wide that these chemical compositions impart Guava Leaf
General bioactivity.Numerous studies show guava leaf extract except with hypoglycemic, antitumor, anti-oxidant, anti diar rhea, drop
A variety of pharmacological activity such as blood glucose and hypotensive.In Peru, Mexico, Caribbean, Africa and Asia etc., there is very long medicine in country
Use history.
The content of the invention
It is an object of the invention to provide a kind of noval chemical compound isolated from Guava Leaf and preparation method and purposes,
And the compound has hypoglycemic and anti-tumor application, can be effectively used for preparing hypoglycemic, anti-tumor function food or medicine.
A kind of noval chemical compound isolated from Guava Leaf provided by the invention, noval chemical compound it is chemical entitled：3, 5-
Dihydroxy -2,4- dimethyl -1-O- (6 '-O- galloyl l- β-D- grapes pyranose)-benzophenone, chemical structural formula
For：
The preparation method of the noval chemical compound provided by the invention isolated from Guava Leaf, comprises the following steps：
（1）Extraction：Guava Leaf raw material is crushed, with 5-10 times of volume 30-90% low-carbons alcohol extracting 2-3 times, each 1-2 h, closed
And extract solution, recycling design is concentrated in vacuo, obtains extract medicinal extract；
（2）Extraction：Extract medicinal extract is dissolved in water, fully extracted with ethyl acetate, combined ethyl acetate extract, vacuum is dense
Contract to obtain acetic acid ethyl ester extract；
（3）Silica gel column chromatography is enriched with：Acetic acid ethyl ester extract carries out silica gel column chromatography separation, and eluant, eluent selects petroleum ether and acetic acid
Ethyl ester carries out gradient elution, is detected through thin-layer chromatography, develops the color, and merges same composition.
（4）Medium pressure column chromatography is enriched with：Above-mentioned eluent is subjected to silica gel medium pressure column chromatographic isolation and purification, entered with acetonitrile and water
Row gradient elution, is detected through thin-layer chromatography, colour developing, merges same composition, noval chemical compound is obtained through recrystallizing methanol.
Step（1）In, the low-carbon alcohols are methanol or ethanol.
Step（3）In, silica gel column chromatography separation, the optional 100-300 mesh silica gel of silica gel.Carried out with petroleum ether and ethyl acetate
During gradient elution, the flow velocity of elution is 1/2-1/5 BV/h, and the volume proportion of petroleum ether and ethyl acetate is followed successively by 1:0、1:1、
1:2、1:3、1:4, detect, develop the color through thin-layer chromatography, merge same composition 1:2、1:3、1:4, wherein component 1:3 noval chemical compounds
Content highest.
Step（4）In, when carrying out gradient elution with acetonitrile and water, the flow velocity of elution is 10-30 mL/min, acetonitrile and water
Volume proportion be followed successively by 10:90、20:80、30:70、40:60, detect, develop the color through thin-layer chromatography, take the volume of acetonitrile and water
Match as 40:60 eluent carries out recrystallizing methanol.
Noval chemical compound prepared by the above method can be used as hypoglycemic and antineoplastic health product or functional food additive.Also
Available for preparing hypoglycemic and antineoplastic.
Noval chemical compound provided by the invention, itself plant origin is nontoxic, in vitro in cell experiment to normal cell without
Toxicity, while In vitro cell experiment shows that it has definite hypoglycemic and antitumor activity.The present invention can be effectively used for dropping blood
Prepared by a large amount of productions of sugar, anti-tumor function food or medicine, the health for diabetes and tumor patient provides safeguard.
Brief description of the drawings
Fig. 1 is noval chemical compound HMBC of the present invention（The hydrocarbon multikey of hydrogen detection is related）Correlation figure.
Fig. 2 is noval chemical compound of the present invention to colon cancer HCT116 cell growth inhibition result of the test figures.
Embodiment
With reference to embodiment, the embodiment of the present invention is described in detail：
Embodiment 1：
The kg of Guava Leaf powder 3.0 of crushing is weighed, 70% ethanol for adding 10 times of volumes extracts 3 times, 2 hours every time, extracts
Liquid is concentrated in vacuo to obtain extract medicinal extract；Extract medicinal extract is dispersed in water, and is extracted with ethyl acetate 3 times, merges concentrated extract
The g of acetic acid ethyl ester extract 100, extract cross 200 mesh silicagel columns, the volume proportion of petroleum ether and ethyl acetate is followed successively by 1:
0、1:1、1:2、1:3、1:4, each BV of ratio 5, the flow velocity of elution is 1/2 BV/h, thin-layer chromatography detection, merges same composition
1:2、1:3、1:4, then through medium pressure column chromatography, acetonitrile-water gradient 10:90、20:80、30:70、40:60, through thin-layer chromatography
Detection, component 40:The 60 noval chemical compound content highests, the compound 40.3 mg. is obtained through recrystallizing methanol
Embodiment 2：
New compound structure identification provided by the present invention：
Compound is a Yellow amorphous powder, and ferric chloride reaction is positive.
Occur 595 (M+Na) quasi-molecular ion peak in ESI-MS, therefore speculate that its molecular weight is 572 dalton.In hydrogen spectrum
Show 2 methyl（δ H 2.08,2.14 (each 3H, s)）；One typical galloyl（δH 7.13 (2H,
s)）.δ H 7.2-7.6 (5H, m) are attributed to single-substituted formoxyl phenyl ring proton, and anomeric proton δ H 4.18 (1H, d,
J=7.8Hz) prove an also glycan molecule.Contain 23 carbon altogether in carbon spectrum, wherein 7 galloyl carbon signal peak (δ C
110.40×2, 121.55, 139.83, 146.50×2, 168.38)；Six Glucose Carbon signal peaks (δ C 105.26,
74.85, 77.42, 70.5, 75.18, 64.41)；Two methyl carbon signal peaks (δ C 9.22,8.41), seven benzoyls
Carbon signal peak (δ C 201.63,143.20,131.93,130.55 × 2,128.28 × 2) and substitute entirely with phloroglucin
Benzene carbon signal peak (δ C 160.95,158.99,153.40,112.98,111.15,109.98) the hydrogen spectrum and carbon of pattern
Modal data is by carefully analyzing its HMBC, HSQC attribution datas, carefully comparing the noval chemical compound and known compound
Guavinoside E, what can be will be apparent that draws, the noval chemical compound is known compound guavinoside E nutgall acyl
Base substitution product.Visible in HMBC spectrograms 1, six Hydrogen Protons of glucose are remotely related to galloyl carbonyl carbon, therefore
Can determine that galloyl is substituted in six of glucose, to sum up determine compound be 3,5- dihydroxy -2,4- dimethyl -
1-O- (6 '-O- galloyl l- β-D- grapes pyranose)-benzophenone.
Embodiment 3：
The noval chemical compound provided in the present invention is hypoglycemic and antitumor cytolytic activity
1. noval chemical compound hypoglycemic activity determines
The disconnected neck of male SD rat is put to death, sterile to open abdomen, takes epididymis outer layer white adipose tissue, is rejected subsidiary blood vessel, is shredded to about 1
mm3Size, add the h of NTx enzymic digestion 1, collect upper-layer fat cell, add appropriate Hanks buffer solutions washing cell three times
Produce Primary adipocyte.200 μ L reaction systems are established in 96 orifice plates：Concentration is 2 × 106The μ of cell/mL cell suspensions 100
The μ L sample solution of+30 μ L hyclones of 6 mg/mL glucose of L+30 μ L+40（Eluted including each extract or each column chromatography
Component）, with saturated humidity, 37 DEG C, 5%CO2 culture 30 min of reaction, it is molten to add the mmol/L adrenaline of 1 μ L 2 per hole
Liquid, then with the h of similarity condition culture 3, ice bath terminating reaction.Developed the color using micro glucose oxidase method, reading on ELIASA,
Determine and calculate each hole concentration of glucose, and compare the consumption concentration for calculating each group glucose with control group, thus evaluate each extraction
Take the intake glucose ability of thing or each column chromatography component, specific formula for calculation is as follows：
Glucose uptake ability=CBlank- CCompound(mmol/L), wherein, CBlankFor the concentration of control group glucose, CCompoundFor sample
Concentration of glucose after culture in 3 hours in remaining medium.
In an aseptic environment, noval chemical compound is dissolved in the Hanks buffer solutions containing DMSO（DMSO final concentration of 0.1%）, mistake
0.22 μm of miillpore filter, final concentration of 20,40,60,80,100 μM of monomer sample solution is configured to, carries out monomer hypoglycemic work
Property analysis, it is as a result as shown in table 1 below and using 0.1%DMSO as blank control group.
Influence of 1. noval chemical compound of the present invention of table to adipocyte glucose uptake amount（X ± SD, n=6）
| Compound concentration（μM） | Glucose uptake amount（mM） |
| 20 | 1.34±0.05 |
| 40 | 2.08±0.02 |
| 60 | 2.51±0.04 |
| 80 | 2.99±0.03 |
| 100 | 3.48±0.01 |
Using a reference value of control group glucose uptake amount as 0, table 1 is the number that monomer promotees glucose uptake absorption in various concentrations
Value, its result show that noval chemical compound of the present invention can promote the intake of glucose to utilize, and show as dose-dependence,
In 20-100 μm of ol/L amount ranges, the concentration of compound is higher, and hypoglycemic effect is more obvious.
2. noval chemical compound antitumor cytolytic activity
By colon cancer HCT116 cell culture in containing 10% hyclone, 1% antibiotic RPMI 1640 culture mediums in, 37 DEG C,
Routine passage culture in 5%CO2 incubators.Cell is inoculated in 96 well culture plates with the concentration in 2000/hole, in containing 10%
Cultivate 72 h in the RPMI 1640 culture mediums of hyclone, after cell attachment, experimental group dosage is 20 μM, 40 μM, 60 μ
M, 80 μM, 100 μM, negative control group adds equivalent RPMI 1640 (DMSO contents are 0.1%), and blank control group only adds equivalent
RPMI 1640.After medicine acts on 24 h, supernatant is abandoned, the μ L of 0.5 mg/mL MTT 100 that preparation is added in every hole continue to train
4 h are supported, abandon supernatant, add 100 μ L DMSO, shake the min of medicine about 10 on mixing shaker, after crystal is fully dissolved, in
570 nm wavelength determine each hole light absorption value in enzyme detector.Calculate cytotoxicity values (CT%), CT%=(1-OD processing/OD
Control) × 100%.
Above-mentioned New diterpenoid is shown in Fig. 2 to the inhibitory action comparative test result of HCT116 Growth of Colon Cancer Cells.
As a result show, the noval chemical compound of gained is tied under tested five concentration (20,40,60,80,100 μM) to HCT116
Colon-cancer cell has direct inhibitory action, and its inhibitory action is proportionate with active component concentration, and inhibiting rate is respectively
10.34%、20.02%、38.44%、70.53%、95%.0.1% DMSO of blank control is to HCT116 colon cancer cells without direct
Inhibitory action.Illustrate that noval chemical compound has certain inhibitory action to HCT116 colon cancer cells.
Claims (8)
1. a kind of noval chemical compound isolated from Guava Leaf, chemistry is entitled：3,5- dihydroxy -2,4- dimethyl -1-O-
(6 '-O- galloyl l- β-D- grapes pyranose)-benzophenone, chemical structural formula are：
。
2. a kind of preparation method for the noval chemical compound isolated from Guava Leaf, it is characterised in that comprise the following steps：
（1）Guava Leaf raw material is crushed, with 5-10 times of volume 30-90 % low-carbons alcohol extracting 2-3 times, each 1-2 h, merging carries
Liquid is taken, recycling design is concentrated in vacuo, obtains extract medicinal extract；
（2 are dissolved in water extract medicinal extract, are fully extracted with ethyl acetate, combined ethyl acetate extract, are concentrated in vacuo to obtain second
Acetoacetic ester extract；
（3）Acetic acid ethyl ester extract carries out silica gel column chromatography separation, and eluant, eluent carries out gradient with ethyl acetate from petroleum ether and washed
It is de-, detect, develop the color through thin-layer chromatography, merge same composition；
（4）Above-mentioned eluent is subjected to silica gel medium pressure column chromatographic isolation and purification, gradient elution is carried out with acetonitrile and water, through thin layer
Analysis detection, colour developing, merges same composition, noval chemical compound is obtained through recrystallizing methanol.
3. a kind of preparation method of noval chemical compound isolated from Guava Leaf according to claim 2, its feature exist
In step（1）In, the low-carbon alcohols are methanol or ethanol.
4. a kind of preparation method of noval chemical compound isolated from Guava Leaf according to claim 2, its feature exist
In step（3）In, when silica gel column chromatography separates, from 100-300 mesh silica gel.
5. a kind of preparation method of noval chemical compound isolated from Guava Leaf according to claim 2, its feature exist
In when carrying out gradient elution with petroleum ether and ethyl acetate, the flow velocity of elution is 1/2-1/5 BV/h, petroleum ether and ethyl acetate
Volume proportion be followed successively by 1:0、1:1、1:2、1:3、1:4, detect, develop the color through thin-layer chromatography, merge same composition 1:2、1:3、
1:4。
6. a kind of preparation method of noval chemical compound isolated from Guava Leaf according to claim 2, its feature exist
In step（4）In, when carrying out gradient elution with acetonitrile and water, the flow velocity of elution is 10-30 mL/min, acetonitrile and water volume
Proportioning is followed successively by 10:90、20:80、30:70、40:60, detect, develop the color through thin-layer chromatography, the volume proportion for taking acetonitrile and water is
40:60 eluent carries out recrystallizing methanol.
7. a kind of noval chemical compound isolated as claimed in claim 1 from Guava Leaf is preparing hypoglycemic and antitumor guarantor
Purposes in terms of health food or functional food.
8. a kind of noval chemical compound isolated as claimed in claim 1 from Guava Leaf is preparing hypoglycemic and antineoplastic
The purposes in object space face.
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| CN111943830A (en) * | 2020-08-20 | 2020-11-17 | 莆田学院 | Novel benzophenone compound and preparation method and application thereof |
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