CN1144803C - Chinese chestnut flower flavone compound and its extraction process - Google Patents
Chinese chestnut flower flavone compound and its extraction process Download PDFInfo
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- CN1144803C CN1144803C CNB001341375A CN00134137A CN1144803C CN 1144803 C CN1144803 C CN 1144803C CN B001341375 A CNB001341375 A CN B001341375A CN 00134137 A CN00134137 A CN 00134137A CN 1144803 C CN1144803 C CN 1144803C
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Abstract
The present invention relates to a new compound, particularly to a Chinese chestnut flower flavone compound, and an extracting method thereof. The compound has the functions of resisting oxidation and removing free oxygen radicals, and is capable of improving blood circulation of brains. Thus, the compound can be used for resisting senility and treating cardiovascular and cerebrovascular diseases, etc.
Description
Technical field
The present invention relates to a kind of new compound, particularly a kind of chestnut flower chromocor compound and extracting method thereof.This compound has to be had anti-oxidantly, removes the oxyradical effect, improves cerebral blood circulation, can be used for anti-ageing, the treatment of cardiovascular and cerebrovascular diseases etc.
Background technology
Chestnut flower is the male inflorescence of Fagaceae Castanea plant Chinese chestnut (Castanea mollissima Blume).Chestnut flower water decoction is used for the treatment of cureless diarrhoea among the people." daily book on Chinese herbal medicine " record chestnut flower tepor, little hardship, puckery.Control scrofula." the southern regions of the Yunnan Province book on Chinese herbal medicine " carries and controls with the passing of time dysentery, blood under the large intestine." Sichuan Chinese medicinal herbal " carries and controls infantile dyspepsia and suffer from diarrhoea more than.Chestnut is distributed widely in all parts of the country, and resource is very abundant, and especially cultivation is concentrated in the Shandong Province, and output is very big, and Li Huadou abandons need not.The home and abroad to colored research seldom.Up to the present, only reported the volatile oil component in the chestnut flower in the prior art, other chemical ingredientss of not appearing in the newspapers.
Summary of the invention
The object of the present invention is to provide a kind of chestnut flower chromocor compound that from chestnut flower water, extracts as effective constituent.
In addition purpose of the present invention be to provide a kind of method of from chestnut flower water, extracting the chestnut flower chromocor compound and,
In addition purpose of the present invention is to provide a kind of purposes of trembling colored chromocor compound.
In order to finish purpose of the present invention, the present invention relates to one group of chestnut flower flavones new compound shown in general formula (I): general formula (I)
The TPC representative
The CPC representative
Wherein:
R1 is H, or OH;
R2 is H, or OH;
R3 is H, or OH;
R4 is TPC, CPC or H;
R5 is TPC, CPC or H;
R6 is TPC, CPC or H;
R7 is TPC, CPC or H;
Or be α type sugar, or be β type sugar.
The inventor has at first carried out comprehensive and systematic extraction and has separated the chemical ingredients of its chestnut flower, mainly is to use the opposed polarity solvent extraction, and multiple and column chromatography for separation repeatedly obtains several compounds.By the mensuration of physico-chemical property, the utilization of multiple spectroscopic technique, the compound that separation is obtained carries out the structure evaluation, identifies the present invention's compound again.These compounds all are to obtain by separating in this compound first.
On the basis of understanding fully its chemical ingredients and content, the flavonoid compound of its main component is carried out bioactivity screening, find resisting oxygen lack under the mouse normal pressure obviously (P＜0.01) and toxicity is less.This result of study has important academic values to the development and use chestnut flower, simultaneously also potential social benefit and economic benefit greatly.
Specifically, the preparation method of chestnut flower flavonoid flower flavone compound may further comprise the steps:
A) adopt 50-95% alcohol reflux chestnut flower meal, extract each 1 hour 3 times;
B) gained liquid is condensed into paste under 50-100 degree centigrade, and the depositing in water with 5 times of amounts of raw material falls then, and is centrifugal, gets the clarifying aqueous solution;
C) with this aqueous solution through macroporous resin adsorption, adsorption column is with the ethanol elution of 40-70%;
D) elutriant gets paste at 50-100 degree centigrade of concentrating under reduced pressure;
E) with 1-3 times of silica gel mixed sample of gained paste, dry, in apparatus,Soxhlet's, ethyl acetate extraction, extracting solution concentrates evaporate to dryness, gets the total flavones part of chestnut flower;
F) the chestnut flower total flavones that obtains with dissolve with ethanol, with 1-3 times of silica gel mixed sample of described paste, with 20 times of silica gel upper props of sample, the volume ratio of chloroform and methyl alcohol is 99: 1-80: 20 gradient elutions, detect with the silica-gel plate thin-layer chromatography, identical effluent merges;
G) the gained effluent is respectively through low pressure silicagel column purifying, at-5-20 ℃ recrystallization, The compounds of this invention.
New representative compounds of the present invention is:
Chestnut glucoside A[chemistry kaempferol 3-oxygen by name-(6 "-E-is right-coumaric acyl)-α-D--mannopyranose glycosides Castanoside A (Kaempferol-3-oxygen--(6 "-E-p-coumaroyl)-α-D-mannopyranoside) .];
Chestnut glucoside B[chemistry kaempferol by name-3-oxygen-[4 ", 6 "-two (right-coumaric acyl)]-α-D mannopyranose glycosides, (kaempferol-3-oxygen-(4 ", 6 "-di-E-p-coumaroyl-)-α-D--mannopyranoside)];
Chestnut glucoside C[chemistry Quercetin by name-3-oxygen-β-D-mannopyranose glycosides (quercetin-3-oxygen-β-D-mannopyopyranoside)]; With
Chestnut glucoside D[chemistry myricetin 3-oxygen-β by name-D-mannopyranose glycosides (Myricetin-3-oxygen-β-D-mannopyranoside D)].
The compounds of this invention can be with oral methods or the medication of parenteral road.Oral medication can be tablet, capsule, granule, Drug coating, and non-have injection and suppository etc. through the intestines drug formulation.These preparations are according to the known method preparation of those skilled in the art.For making tablet, capsule, the used auxiliary material of Drug coating is the auxiliary agent of conventional usefulness, starch for example, gelatin, gum arabic, silica, polyoxyethylene glycol, the used solvent of liquid dosage form for example has water, ethanol, propylene glycol, plant oil such as Semen Maydis oil, peanut oil olive wet goods.Containing in the preparation of The compounds of this invention also can have other auxiliary agent, tensio-active agent for example, lubricant, disintegrating agent, sanitas, correctives, pigment etc.
The dosage that contains general formula of the present invention (I) compound in tablet, capsule, Drug coating, injection or suppository is that the compound amount that exists in unit dosage form is calculated.
Embodiment
In order further to understand the present invention, describe the present invention in detail below with reference to embodiment, but the description of indefiniteness.
Embodiment 1
Get chestnut flower meal 50g, 50% alcohol reflux, each 1 hour, extract 3 times, gained liquid is condensed into paste for 100 ℃, falls with raw material 250ml depositing in water then, and is centrifugal, gets the clarifying aqueous solution.
This aqueous solution is through macroporous resin adsorption, and post is with 70% ethanol elution, and 50 ℃ of concentrating under reduced pressure of elutriant with 3 times of silica gel mixed samples of gained cream, dry, in apparatus,Soxhlet's, and ethyl acetate extraction, extracting solution concentrates evaporate to dryness and gets chestnut flower total flavones part 1.8g.
The chestnut flower total flavones dissolves with small amount of ethanol, the 1.8g silica gel mixed sample, and with sample 36g silica gel upper prop, the volume ratio of chloroform and methyl alcohol is 99: 1-80: 20 gradient elutions, detect with the silica-gel plate thin-layer chromatography, identical effluent merges.
The gained effluent is respectively through low pressure silicagel column purifying, at 0 ℃ of recrystallization, must tremble glucoside B105mg, chestnut glucoside A10mg, chestnut glucoside C42mg, chestnut glucoside D31mg.
Embodiment 2
According to the method for embodiment 1, get chestnut flower meal 50g, with 95% alcohol reflux it, extract 3 times, each 1 hour, gained liquid was condensed into paste under 70 degrees centigrade, fell with raw material 250ml depositing in water then, and is centrifugal, the clarifying aqueous solution.
This aqueous solution is through macroporous resin adsorption, and post is with 60% ethanol elution, and 100 degrees centigrade of following concentrating under reduced pressure of elutriant with 1 times of silica gel mixed sample of gained cream, dry, in apparatus,Soxhlet's, and ethyl acetate extraction, extracting solution concentrates evaporate to dryness and gets chestnut flower total flavones part 1.2g.
The chestnut flower total flavones dissolves with small amount of ethanol, the 3.6g silica gel mixed sample, and with sample 24g silica gel upper prop, the volume ratio of chloroform and methyl alcohol is 99: 1-80: 20 gradient elutions, detect with the silica-gel plate thin-layer chromatography, identical effluent merges.
The gained effluent is respectively through low pressure silicagel column purifying, at 20 degrees centigrade of recrystallizations, must tremble glucoside B62mg, chestnut glucoside A6mg, chestnut glucoside C11mg, chestnut glucoside D13mg.
Embodiment 3
According to the method for embodiment 1, get chestnut flower meal 50g, 70% alcohol reflux, each 1 hour, extract 3 times, gained liquid is condensed into paste under 50 degrees centigrade, fall with raw material 250ml depositing in water then, and is centrifugal, gets the clarifying aqueous solution.
This aqueous solution is through macroporous resin adsorption, and post is with 40% ethanol elution, and 60 ℃ of concentrating under reduced pressure of elutriant with 2 times of silica gel mixed samples of gained cream, dry, in apparatus,Soxhlet's, and ethyl acetate extraction, extracting solution concentrates evaporate to dryness and gets chestnut flower total flavones part 2.6g.
The chestnut flower total flavones dissolves with small amount of ethanol, the 5.2g silica gel mixed sample, and with sample 52g silica gel upper prop, the volume ratio of chloroform and methyl alcohol is 99: 1-80: 20 gradient elutions, detect with the silica-gel plate thin-layer chromatography, identical effluent merges.
The gained flow point is respectively through low pressure silicagel column purifying, at-5 degrees centigrade of recrystallizations, must tremble glucoside B150mg, chestnut glucoside A35mg, chestnut glucoside C61mg, chestnut glucoside D23mg.
Through chestnut glucoside A, B, C, D that embodiment 1-3 obtains, learn that its structure and data are as follows through physico-chemical analysis:
Chestnut glucoside A
(castanoside?A) R1＝R3＝H R2＝OH
R4＝R5＝R6＝H R7＝TPC
C-1 "
=β type C-2 "
=β type C-4 "
=α type
Chinese chestnut glucoside B
(castanoside?B)
R1＝R3＝H R2＝OH
R4＝R5＝H R6＝R7＝TPC
C-1 "
=β type C-2 "
=β type C-4 "
=α type
Chestnut glucoside C
(castanoside?C) R1＝H R3＝R2＝OH
R4＝R5＝R6＝R7＝H
C-1 "
=β type C-2 "
=α type C-4 "
=β type
Chestnut glucoside D
(castanoside?D)
R1＝R2＝R3＝OH
R4＝R5＝R6＝R7＝H
C-1 "
=β type C-2 "
=α type C-4 "
=β type
Castanoside A:mp248 ℃; Ultimate analysis is: C, 60.70%; H, 4.42%.calcd.value:C, 60.61%; H, 4.38%; UV (MeOH) λ
Max315,265nm ,+NaOMe 370,315nm:+AlCl
3365,315nm; + AlCl
3/ HCl 315,265nm; + NaOAc 375,280nm; + NaOAc/H
3BO
3375,265.nm; IR (KBr) ν
Max: 3393 (OH), 2916,1692 (C=O), 1686 (C=O), 1655,1606,1515 (Ar) 1439,1360,1018cm
-1 1H and
13C NMR data see Table 1; EIMS m/z:286,229,213,184,164,146,128,121,83,73,65,41.FABMS m/z:595[M+H]
+, 567,553,467,403,311,287,219,191,127,99.
Castanoside B:mp236 ℃; Ultimate analysis is: C, 63.30%; H, 4.28%.calcd.value:C, 63.24%; H, 4.32%; UV (MeOH) λ
Max: 314,268,225 (sh) nm; + NaOMe 370,315nm+AlCl
3: 370,310nm; + AlCl
3/ HCl 315,268nm; + NaOAC 370,280nm; ± NaOAC/H
3BO
3375,265nm; IR (KBr) ν
Max: 412 (OH), 2960,1690 (C=O), 1655 (C=O), 1632,1606,1515 (Ar), 1439,1359,1207,1024cm
-1 1H and
13C NMR data see Table1; EIMS m/z:286,269,249,229,201,184,164,136,121,108,93,83,69,51; FABMS m/z:741[M+H]
+, 455,287,271,185,147,115,107,104.
Castanoside C:mp250 ℃; Ultimate analysis is: C, 54.23%; H, 4.25%.calcd.value:C, 54.31%; H, 4.31%; UV (MeOH) λ
Max: 365,255,225 (sh) nm; + NaOAC415,307nm; + AlCl
3410,307nm; + AlCl
3/ HCl 365,307nm; + NaOAc 415,315nm; + NaOAC/H
3BO
3385,315nm; IR (KBr) ν
Max: 3514 (OH), 2924,, 1656 (C=O), 1607,1567,1501 (Ar), 1367,1088cm;
1H and
13C NMR see Table 2; EIMS m/z:358,336,302,286,257,229,200,167,153,125,125,97,57; FABMS m/z:465[M+H]
+, 429,394,375,303,275,19,182,99.
Castaneside D.mp246 ℃; Ultimate analysis is: C, 52.45%; H, 4.22%.calcd.value:C, 52.50%; H, 4.17%; UV (MeOH) λ
Max: .370,270nm ,+NaOMe420,270nm; + NaOAc 430,280nm; + NaOAc/H
3BO
3380,260nm; + AlCl
3430,280nm; + AlCl
3/ HCl365,260nm; IR (KBr) ν
Max: 3388 (OH), 2940,1655 (C=O), 1604,1572,1508 (Ar), 1492,1317,1202,1029cm
-1,
1H and
13C NMR see Table 2; EIMSm/z:368,318,302,273,245,219,191,170,144,112,97,60; FABMS m/z:481[M+H]
+, 413,365,319,219,191,115.
The data of the nuclear magnetic resonance spectrum of table 1 chestnut glucoside A-B
1H and
13C NMR (, DMSO-D
6)
Castanoside?A
Castanoside?B
C/H?
13C?NMR(ppm) DEPT?
1H?NMR(ppm?Jin?Hz)
13C?NMR(ppm) DEPT
1H?NMR(ppm Jin?Hz)
2 156.51 C 156.87 C
3 133.43 C 132.89 C
4 177.67 C＝O 177.47 C＝O
5 161.31 C 161.49 C
6 98.91 CH 6.13d(1.9) 98.67 CH 6.13d(1.9)
7 164.09 C 164.53 C
8 93.08 CH 6.39d(1.9) 94.10 CH 6.39d(1.9)
9 156.51 C 156.87 C
10 104.02 C 104.24 C
1′ 121.00 C 120.99 C
2′ 131.08 CH 8.06d(8.6) 131.21 CH 8.04d(8.6)
3′ 115.89 CH 6.87d(8.6) 115.56 CH 6.87d(8.6)
4′ 160.13 C 160.43 C
5′ 115.89 CH 6.87d(8.6) 115.56 CH 6.87d(8.6)
6′ 131.08 CH 8.06d(8.6) 131.21 CH 8.04d(8.6)
PhOH 12.59，10.87，10.16，10.00 12.58，10.84，10.19，10.03(PhOH×2)
1″ 101.81 CH 5.42?d(6.7) 99.16 CH 5.71d(6.7)
2″ 73.13 CH 3.65dd(6.7，8.9) 73.95 CH 3.59dd(6.7，8.9)
3″ 71.20 CH 3.58t(8.9) 74.37 CH 4.91t(8.9)
4″ 68.44 CH 3.68t(8.9) 70.58 CH 3.54t(8.9)
5″ 73.03 CH 3.52m 73.97 CH 3.56m
6″ 63.36 CH
2?4.09m 63.36 CH
2?4.16m
α166.31 C＝O 166.58 C＝O
β113.81 CH 6.08d(16) 114.61 CH 6.36d((16)
γ144.79 CH 7.36d(16) 145.59 CH 7.64d(16)
1?125.09 C 125.52 C
2 130.26 CH?7.33d(8.4) 130.73 CH?7.38d(8.4)
3 115.24 CH?6.78d(8.4) 116.27 CH?6.81d(8.4)
4 159.95 C 160.18 C
5 115.24 CH?6.78d(8.4) 116.27 CH?6.81d(8.4)
6 130.26 CH?7.33d(8.4) 130.73 CH?7.38d(8.4)
α″″ 166.30 C＝O
β″″ 113.95 CH?6.17d(16)
γ″″ 145.13 CH?7.58d(16)
1″″ 125.37 C
2″″ 130.58 CH?7.34d(8.4)
3″″ 116.21 CH?6.78d(8.4)
4″″ 160.18 C
5″″ 116.21 CH?6.78d(8.4)
6″″ 130.58 CH?7.34d(8.4)
The data of the nuclear magnetic resonance spectrum of table 2 chestnut glucoside C-D
1H and
13C NMR (DMSO-d
6)
Castanoside?C
Castanoside?D
C/H?
13C?NMR(ppm) DEPT?
1H?NMR(ppm?Jin?Hz)
13C?NMR(ppm) DEPT?
1H?NMR(ppm?Jin?Hz)
2 156.40 C 156.44 C
3 133.65 C 133.96 C
4 177.66 C＝O 177.63 C＝O
5 161.40 C 161.43 C
6 98.82 CH?6.20d(2.0) 98.83 CH?6.20d(2.0)
7 164.28 C 164.34 C
8 93.66 CH?6.37d(2.0) 93.57 CH?6.37d(2.0)
9 156.46 C 156.44 C
10 104.09 C 104.10 C
1′ 122.16 C 120.18 C
2′ 115.34 CH 7.65d(2.1) 108.76 CH?7.20s
3′ 144.99 C 145.59 C
4′ 148.62 C 136.89 C
5′ 116.10 CH 6.82d(8.6) 145.59 C
6′ 121.61 CH 7.68d(8.6，2.1) 108.76 CH 7.20s
PhOH?12.63，10.85，?9.71，9.14 12.83，10.85，9.09(PhOH×3)
1″ 101.91 CH 5.38?d(7.8) 102.24 CH 5.35d(7.8)
2″ 71.37 CH 3.42dd(7.8，8.9)?71.41 CH 3.46dd(7.8，8.9)
3″ 73.35 CH 3.32t(8.9) 73.49 CH 3.33t(8.9)
4″ 68.09 CH 3.64t(8.9) 68.21 CH 3.65t(8.9)
5″ 76.01 CH 3.21m 76.14 CH 3.21m
6″ 60.03 CH
2?3.25m 60.25 CH
23.25m
Experimental example 1 chestnut flower chromocor compound is to the test of mouse resisting oxygen lack
8 every group of mouse random packet, gastric infusion, once a day, each 0.5ml/20g mouse (drug level is 20mg/ml), continuous irrigation stomach 7 days, 1.5 hours begin to do hypoxia endurance test after last administration, learn by statistics and handle, chestnut flower flavones group and control group relatively have significant differences (P＜0.01).Illustrating that the chestnut flower flavones has an effect to cardiovascular, is the cardiovascular effect of treatment of a new class type that gets a good chance of.
Experimental example 2 chestnut flower chromocor compounds are to the acute toxicity test of mouse
Because of being subjected to the influence of mouse stomach amount, can't measure, so done the test of dosis tolerata,, do not find the overt toxicity reaction to the disposable filling stomach chestnut of mouse flower total flavones 0.8ml/20g (1.6g/kg), observed 7 days, there is not death, well-grown.Anatomic observation, the main organs Non Apparent Abnormality shows that tentatively this product toxic side effect is very little.
This shows that the chestnut flower chromocor compound has phenolic hydroxyl group and unsaturated double-bond, it is anti-oxidant to indicate that it has, and removes the oxyradical effect, improve cerebral blood circulation, can be used for anti-ageingly, cardiovascular and cerebrovascular diseases is as hypertension, diseases such as coronary heart disease, and this class disease incidence height, quantity is big.Therefore this compounds has its important medical use, and its DEVELOPMENT PROSPECT is better, and potential market and considerable economic worth are arranged.
Claims (8)
1, the chestnut flower chromocor compound of a kind of general formula (I),
The TPC representative
The CPC representative
Wherein:
R1 is H, or OH;
R2 is H, or OH;
R3 is H, or OH;
R4 is TPC, CPC or H;
R5 is TPC, CPC or H;
R6 is TPC, CPC or H;
R7 is TPC, CPC or H;
2, compound as claimed in claim 1 is characterized in that described compound is kaempferol-3-oxygen-(6 "-E-to coumaric acyl)-α-D-mannopyranose glycosides.
3, compound as claimed in claim 1, it is characterized in that described compound be kaempferol-3-oxygen-[4 ", 6 "-two-(E-right-coumaric acyl)]-α-D-mannopyranose glycosides.
4, compound as claimed in claim 1 is characterized in that described compound is Quercetin-3-oxygen-β-D-mannopyranose glycosides.
5, compound as claimed in claim 1 is characterized in that described compound is myricetin-3-oxygen-β-D-mannopyranose glycosides.
6, a kind of compound as claimed in claim 1 of medicine effective dose and pharmaceutical composition of pharmaceutically acceptable carrier of containing.
7, a kind of preparation method of chestnut flower flavonoid compound as claimed in claim 1 may further comprise the steps:
A) adopt 50-95% alcohol reflux chestnut flower meal, extract each 1 hour 3 times;
B) gained liquid is condensed into paste under 50-100 degree centigrade, and the depositing in water with 5 times of amounts of raw material falls then, and is centrifugal, gets the clarifying aqueous solution;
C) with this aqueous solution through macroporous resin adsorption, adsorption column is with the ethanol elution of 40-70%;
D) elutriant gets paste at 50-100 degree centigrade of concentrating under reduced pressure;
E) with 1-3 times of silica gel mixed sample of described paste, dry, in apparatus,Soxhlet's, ethyl acetate extraction, extracting solution concentrates evaporate to dryness, gets the total flavones part of chestnut flower;
F) the chestnut flower total flavones that obtains with dissolve with ethanol, with 1-3 times of silica gel mixed sample of described paste, with 20 times of silica gel upper props of sample, the volume ratio of chloroform and methyl alcohol is 99: 1-80: 20 gradient elutions, detect with the silica-gel plate thin-layer chromatography, identical effluent merges;
G) the gained effluent is respectively through low pressure silicagel column purifying, at-5-20 ℃ recrystallization, The compounds of this invention.
8, the application of compound as claimed in claim 1 in the preparation anti-anoxic medicine.
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| CN105017357B (en) * | 2015-08-05 | 2018-10-23 | 沈阳药科大学 | Polyphenol chromocor class compound and its preparation method and application |
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| CN101906353B (en) * | 2010-08-03 | 2012-05-30 | 河北科技大学 | Extraction method and application of chestnut flower essential oil |
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| CN108904585B (en) * | 2018-09-18 | 2021-05-28 | 青岛农业大学 | Method for improving animal semen quality by using chestnut flower ethyl acetate extract |
| CN111150754B (en) * | 2020-02-24 | 2021-06-22 | 河北科技师范学院 | Application of chestnut flower extract in preparation of food or anti-inflammatory drugs |
| CN115024341B (en) * | 2022-07-22 | 2024-01-23 | 河北科技师范学院 | Antibacterial agent containing chestnut extract, preparation method thereof and plant disease treatment method |
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| CN105017357B (en) * | 2015-08-05 | 2018-10-23 | 沈阳药科大学 | Polyphenol chromocor class compound and its preparation method and application |
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