CN107056800B - Dimer flavone constituents and its separation method and application in a kind of Tsuga longibracteata - Google Patents
Dimer flavone constituents and its separation method and application in a kind of Tsuga longibracteata Download PDFInfo
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- CN107056800B CN107056800B CN201710396384.7A CN201710396384A CN107056800B CN 107056800 B CN107056800 B CN 107056800B CN 201710396384 A CN201710396384 A CN 201710396384A CN 107056800 B CN107056800 B CN 107056800B
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- longibracteata
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- 241000544353 Nothotsuga longibracteata Species 0.000 title claims abstract description 25
- 239000000539 dimer Substances 0.000 title claims abstract description 21
- GAMYVSCDDLXAQW-AOIWZFSPSA-N Thermopsosid Natural products O(C)c1c(O)ccc(C=2Oc3c(c(O)cc(O[C@H]4[C@H](O)[C@@H](O)[C@H](O)[C@H](CO)O4)c3)C(=O)C=2)c1 GAMYVSCDDLXAQW-AOIWZFSPSA-N 0.000 title claims abstract description 20
- 229930003944 flavone Natural products 0.000 title claims abstract description 20
- 235000011949 flavones Nutrition 0.000 title claims abstract description 20
- VHBFFQKBGNRLFZ-UHFFFAOYSA-N vitamin p Natural products O1C2=CC=CC=C2C(=O)C=C1C1=CC=CC=C1 VHBFFQKBGNRLFZ-UHFFFAOYSA-N 0.000 title claims abstract description 20
- 150000002212 flavone derivatives Chemical class 0.000 title claims abstract description 18
- 238000000926 separation method Methods 0.000 title claims abstract description 18
- 239000000470 constituent Substances 0.000 title claims abstract description 12
- 238000000605 extraction Methods 0.000 claims abstract description 19
- 230000003064 anti-oxidating effect Effects 0.000 claims abstract description 3
- 239000000284 extract Substances 0.000 claims description 13
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims description 9
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 claims description 9
- GBMDVOWEEQVZKZ-UHFFFAOYSA-N methanol;hydrate Chemical compound O.OC GBMDVOWEEQVZKZ-UHFFFAOYSA-N 0.000 claims description 9
- 238000002360 preparation method Methods 0.000 claims description 9
- 239000000126 substance Substances 0.000 claims description 9
- LRHPLDYGYMQRHN-UHFFFAOYSA-N N-Butanol Chemical compound CCCCO LRHPLDYGYMQRHN-UHFFFAOYSA-N 0.000 claims description 8
- 238000004128 high performance liquid chromatography Methods 0.000 claims description 8
- 239000003208 petroleum Substances 0.000 claims description 8
- 238000010829 isocratic elution Methods 0.000 claims description 7
- 238000010828 elution Methods 0.000 claims description 6
- 239000000469 ethanolic extract Substances 0.000 claims description 6
- 238000001514 detection method Methods 0.000 claims description 5
- SRCZQMGIVIYBBJ-UHFFFAOYSA-N ethoxyethane;ethyl acetate Chemical compound CCOCC.CCOC(C)=O SRCZQMGIVIYBBJ-UHFFFAOYSA-N 0.000 claims description 5
- 238000010898 silica gel chromatography Methods 0.000 claims description 5
- 150000002206 flavan-3-ols Chemical class 0.000 claims description 4
- 238000010992 reflux Methods 0.000 claims description 4
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 4
- HIXDQWDOVZUNNA-UHFFFAOYSA-N 2-(3,4-dimethoxyphenyl)-5-hydroxy-7-methoxychromen-4-one Chemical compound C=1C(OC)=CC(O)=C(C(C=2)=O)C=1OC=2C1=CC=C(OC)C(OC)=C1 HIXDQWDOVZUNNA-UHFFFAOYSA-N 0.000 claims description 3
- RTZKZFJDLAIYFH-UHFFFAOYSA-N ether Substances CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 claims description 3
- 239000002024 ethyl acetate extract Substances 0.000 claims description 3
- CITFYDYEWQIEPX-UHFFFAOYSA-N Flavanol Natural products O1C2=CC(OCC=C(C)C)=CC(O)=C2C(=O)C(O)C1C1=CC=C(O)C=C1 CITFYDYEWQIEPX-UHFFFAOYSA-N 0.000 claims description 2
- 238000001035 drying Methods 0.000 claims description 2
- 235000011987 flavanols Nutrition 0.000 claims description 2
- 150000001875 compounds Chemical class 0.000 abstract description 19
- 238000000034 method Methods 0.000 abstract description 11
- 239000007788 liquid Substances 0.000 abstract description 3
- 238000005516 engineering process Methods 0.000 abstract description 2
- 239000000463 material Substances 0.000 abstract description 2
- 230000000144 pharmacologic effect Effects 0.000 abstract description 2
- 239000002904 solvent Substances 0.000 abstract description 2
- 230000004913 activation Effects 0.000 abstract 1
- 238000013375 chromatographic separation Methods 0.000 abstract 1
- 238000002791 soaking Methods 0.000 abstract 1
- 239000000523 sample Substances 0.000 description 6
- -1 flavone compound Chemical class 0.000 description 5
- 235000019441 ethanol Nutrition 0.000 description 4
- 238000005481 NMR spectroscopy Methods 0.000 description 3
- PBCJIPOGFJYBJE-UHFFFAOYSA-N acetonitrile;hydrate Chemical compound O.CC#N PBCJIPOGFJYBJE-UHFFFAOYSA-N 0.000 description 3
- 238000002114 high-resolution electrospray ionisation mass spectrometry Methods 0.000 description 3
- 238000001644 13C nuclear magnetic resonance spectroscopy Methods 0.000 description 2
- 238000005160 1H NMR spectroscopy Methods 0.000 description 2
- 241000196324 Embryophyta Species 0.000 description 2
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 2
- 241000218685 Tsuga Species 0.000 description 2
- 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 2
- 239000003814 drug Substances 0.000 description 2
- 230000000694 effects Effects 0.000 description 2
- 230000002349 favourable effect Effects 0.000 description 2
- 238000003919 heteronuclear multiple bond coherence Methods 0.000 description 2
- 238000005570 heteronuclear single quantum coherence Methods 0.000 description 2
- 230000004048 modification Effects 0.000 description 2
- 238000012986 modification Methods 0.000 description 2
- 230000003595 spectral effect Effects 0.000 description 2
- OCZVHBZNPVABKX-UHFFFAOYSA-N 1,1-diphenyl-2-(2,4,6-trinitrophenyl)hydrazine;ethanol Chemical compound CCO.[O-][N+](=O)C1=CC([N+](=O)[O-])=CC([N+]([O-])=O)=C1NN(C=1C=CC=CC=1)C1=CC=CC=C1 OCZVHBZNPVABKX-UHFFFAOYSA-N 0.000 description 1
- XILIYVSXLSWUAI-UHFFFAOYSA-N 2-(diethylamino)ethyl n'-phenylcarbamimidothioate;dihydrobromide Chemical compound Br.Br.CCN(CC)CCSC(N)=NC1=CC=CC=C1 XILIYVSXLSWUAI-UHFFFAOYSA-N 0.000 description 1
- 235000007173 Abies balsamea Nutrition 0.000 description 1
- 241000218631 Coniferophyta Species 0.000 description 1
- 238000002835 absorbance Methods 0.000 description 1
- 239000001887 acacia decurrens willd. var. dealbata absolute Substances 0.000 description 1
- 230000009471 action Effects 0.000 description 1
- 230000001476 alcoholic effect Effects 0.000 description 1
- 230000003078 antioxidant effect Effects 0.000 description 1
- 230000009286 beneficial effect Effects 0.000 description 1
- 238000004364 calculation method Methods 0.000 description 1
- 230000008859 change Effects 0.000 description 1
- 238000006243 chemical reaction Methods 0.000 description 1
- 239000003153 chemical reaction reagent Substances 0.000 description 1
- 239000003795 chemical substances by application Substances 0.000 description 1
- WORJEOGGNQDSOE-UHFFFAOYSA-N chloroform;methanol Chemical compound OC.ClC(Cl)Cl WORJEOGGNQDSOE-UHFFFAOYSA-N 0.000 description 1
- 239000012153 distilled water Substances 0.000 description 1
- 229940079593 drug Drugs 0.000 description 1
- 235000013399 edible fruits Nutrition 0.000 description 1
- QOLIPNRNLBQTAU-UHFFFAOYSA-N flavan Chemical compound C1CC2=CC=CC=C2OC1C1=CC=CC=C1 QOLIPNRNLBQTAU-UHFFFAOYSA-N 0.000 description 1
- 238000000338 in vitro Methods 0.000 description 1
- 238000007689 inspection Methods 0.000 description 1
- RBTARNINKXHZNM-UHFFFAOYSA-K iron trichloride Chemical compound Cl[Fe](Cl)Cl RBTARNINKXHZNM-UHFFFAOYSA-K 0.000 description 1
- 235000015110 jellies Nutrition 0.000 description 1
- 239000008274 jelly Substances 0.000 description 1
- 239000000178 monomer Substances 0.000 description 1
- 230000003647 oxidation Effects 0.000 description 1
- 238000007254 oxidation reaction Methods 0.000 description 1
- 235000013824 polyphenols Nutrition 0.000 description 1
- 230000008569 process Effects 0.000 description 1
- 238000013441 quality evaluation Methods 0.000 description 1
- 238000004064 recycling Methods 0.000 description 1
- 239000012488 sample solution Substances 0.000 description 1
- 230000011218 segmentation Effects 0.000 description 1
- 238000002798 spectrophotometry method Methods 0.000 description 1
- 238000001228 spectrum Methods 0.000 description 1
- 238000010183 spectrum analysis Methods 0.000 description 1
- 150000003648 triterpenes Chemical class 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D493/00—Heterocyclic compounds containing oxygen atoms as the only ring hetero atoms in the condensed system
- C07D493/22—Heterocyclic compounds containing oxygen atoms as the only ring hetero atoms in the condensed system in which the condensed system contains four or more hetero rings
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- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Medicines Containing Plant Substances (AREA)
Abstract
The invention discloses a kind of to isolate and purify the method for noval chemical compound and the application of the noval chemical compound from Tsuga longibracteata.It is characteristic of the invention that isolating and purifying noval chemical compound from Tsuga longibracteata using traditional extraction separation method combination modern separation technology: being extracted including solvent soaking, extraction and separation, positive pillar layer separation, the methods of half preparative high-performance liquid chromatographic separation.The noval chemical compound isolated and purified is named as tsugadiflavonol A.Isolated one new dimer flavone constituents are extracted in the extraction separation method success of new component provided by the invention from Tsuga longibracteata, provide material base for the further pharmacological effect research of Tsuga longibracteata.Through Preliminary activation studies have shown that tsugadiflavonol A has preferable antioxidation, there is good development and application prospect.
Description
Technical field
The present invention relates to chemical field separation and extraction technologies, and in particular, to a dimer flavanols in Tsuga longibracteata
Compound and its method for separating and preparing and application.
Background technique
Tsuga longibracteata (Tsuga longibracteata) belongs to a relict type under gymnosperm Pinaceae Hemlock,
It is distributed in Guangdong, Jiangxi, Guangxi, Fujian, Hunan, the ground such as Guizhou are the distinctive plant in China.The trunk of this tree is tall and straight, firmly
Spend larger, material is excellent, and widely used, economic value is high, and bark can extract mimosa extract, can synthetism.
Main component has lignanoids, triterpenes and flavone compound in hemlock.Flavone compound is one
Class is present in the polyphenol compound in various plants, has different bioactivity and pharmacological action.So far not yet
The report of chemical component extraction and separation technology in related Tsuga longibracteata bark.This patent discloses one kind from Tsuga longibracteata bark
The method of one dimer flavane alcoholic compound of separation and Extraction, provides substance base for Tsuga longibracteata quality evaluation and drug efficacy study
Plinth.
Summary of the invention
The present invention provides one kind from Tsuga longibracteata isolated dimer flavanols compounds simultaneously provide preparation
The method of such compound, the extracting method controllability and favorable reproducibility, it is easy to operate, it is suitble to the extraction separation of micro substance.
Wherein, the present invention provides dimer flavone constituents in a kind of Tsuga longibracteata, titles are as follows:
Tsugadiflavonol A, chemical structural formula are as follows:
The present invention also provides dimer flavone constituents extraction separation methods in this Tsuga longibracteata, including following step
Suddenly.
1) Tsuga longibracteata bark part is taken, after drying, crushing, extracts 1~4 with 70~95% alcohol reflux of volume fraction
It is secondary, it is concentrated under reduced pressure to give ethanol extract；
2) after dispersing hot water for the middle gained ethanol extract of step 1), successively with petroleum ether, ethyl acetate and n-butanol extraction
It takes 1~4 time, is concentrated under reduced pressure to give each position medicinal extract；
3) ethyl acetate extract medicinal extract in step 2) is separated by silica gel column chromatography, with petroleum ether-ethyl acetate with not
Same volume is than gradient elution, in conjunction with TLC detection method, is divided into several components according to polarity difference；
4) some component in step 3) is crossed into preparation HPLC, with methanol-water isocratic elution, is divided into several subfractions；
5) some subfraction obtained in step 4) is crossed into preparation HPLC, with methanol-water isocratic elution, obtains this chemical combination
Object.
Above-mentioned steps 4) and step 5) with acetonitrile-water replace methanol-water isocratic elution, also available substantially similar knot
Fruit.
The present invention extracts the advantages of flavanols compounds from Tsuga longibracteata and is, first by silica gel column chromatography, uses
TLC method combines ultraviolet tracking to carry out rough segmentation, and recycling prepares the isolated monomer of HPLC chromatogram, and whole process only uses once
Silica gel column chromatography, reduces sample loss, and separation method is not easy to flow using preparation HPLC controllability and favorable reproducibility, micro constitutent
It loses, operation is also relatively simple.
Detailed description of the invention
Fig. 1 is the HR-ESI-MS of dimer flavone class compound of the present invention；
Fig. 2 is dimer flavone class compound of the present invention1H-NMR spectrogram；
Fig. 3 is dimer flavone class compound of the present invention13C-NMR spectrogram；
Fig. 4 is the nuclear magnetic resonance HSQC spectrogram of dimer flavone class compound of the present invention；
Fig. 5 is the nuclear magnetic resonance HMBC spectrogram of dimer flavone class compound of the present invention.
Specific embodiment
Now in conjunction with embodiment, the invention will be further described.
Embodiment 1
The preparation method of dimer flavone class compound of the present invention the following steps are included:
1) take Tsuga longibracteata dry bark 3.7kg, after crushed, with 95% alcohol at normal temperature of volume fraction extract 3 times, every time
7 days, it is concentrated under reduced pressure to give ethanol extract 610g；
2) by after ethanol extract is scattered in water in step 1), successively with petroleum ether, ethyl acetate and extracting n-butyl alcohol 3 times,
It is concentrated under reduced pressure to give each position medicinal extract；
3) by ethyl acetate extract medicinal extract point 388g in step 2), upper silica gel column chromatography, with petroleum ether-ethyl acetate with body
Product is than 3:1,1:1,1:2,10:1 gradient elution, in conjunction with TLC detection method, is divided into 5 components according to polarity difference, and Fr.1~
Fr.5, each component combination TLC is analyzed below；
4) the 4th component Fr.4 in step 3) is crossed into preparation HPLC, with the methanol-water of volume fraction 55%, chromatographic column is used
C18, 20 × 250mm, flow velocity 20mL/min elution, fraction is divided into 5 parts between Detection wavelength 230nm, 5~15min of collection
Fr.4.1~Fr.4.5；
5) Fr.4.3 crosses preparation HPLC in step 4), with 45% methanol-water of volume fraction, chromatographic column C18, 10 ×
250mm, flow velocity 4mL/min elution, collect chromatographic peak between 8~12min, and Detection wavelength 254nm obtains the compound.
Above-mentioned steps 1) in refluxing extraction hydrous ethanol volume fraction 85%, 90%, 100%, refluxing extraction 1 time, 2
It is secondary, 4 times；Extraction 1 time, 2 times, 4 times in step 2)；Volume fraction 45%, 50%, 55% acetonitrile-water are used in step 4)；Step
5) volume fraction 40%, 45%, 50% acetonitrile-water are used in.With embodiment 1, can also obtain of the present invention has step
Beneficial effect.
The present invention carries out the condition that TLC inspection is known: solvent is petroleum ether-ethyl acetate system and chloroform-methanol system, is shown
Toner a: fluorescence is observed under ultraviolet lamp (254nm)；The sprinkling of color developing agent b:10% sulfuric acid ethyl alcohol, 105 DEG C are baked to colour developing.
Structural Identification: the spectral technique utilized, mainly include nuclear magnetic resoance spectrum (1H-NMR、13C-NMR、DEPT、HSQC、
) and the structure of mass spectral analysis (HR-ESI-MS) authenticating compound HMBC.
The compound is yellow jelly, meets the aobvious blue of ferric trichloride reagent.HR-ESI-MS[M+H]+:559.12244
(calculated value 559.12349) determines that the molecular formula of compound is C in conjunction with H NMR spectroscopy30H22O11, by spectral technique, determine the change
Conjunction object is tsugadiflavonol A.Its nuclear magnetic data is shown in Table 1.
Nuclear magnetic data (400/100MHz, the CD of 1 framework compound of table3OD):
To further illustrate effect of the present invention in field of medicaments, test to come below by part antioxidation activity in vitro
Explanation.
This test uses oxidation resistance of the DPPH spectrophotometry to evaluate monomeric compound prepared by the present invention.
4 test tubes are taken, wherein 1 pipe is blank group, take 2ml various concentration sample liquid to be tested that 2ml 0.16mmol/L is added
DPPH ethanol solution, adds 2ml 0.05mol/L Tris-HC1 (pH=7.4) buffer, 25 DEG C of reaction 20min,
It is Ai that absorbance value is measured at 517nm, and blank control group replaces test liquid with the distilled water of same volume.Each sample group does 6
A repetition calculates its average value.The clearance rate calculation formula of DPPH free radical:
Ai is the mean light absorbency of sample；Ao is the mean light absorbency of blank.
IC of the calculated result test sample to DPPH clearance rate50Value is 21-68 μ g/mg.The experimental results showed that test sample
There is certain clearance rate to DPPH free radical, and clearance rate is improved with the increase of test sample solution concentration.Show
Tsugadiflavonol A has certain antioxidant activity.
It although an embodiment of the present invention has been shown and described, for the ordinary skill in the art, can be with
A variety of variations, modification, replacement can be carried out to these embodiments without departing from the principles and spirit of the present invention by understanding
And modification, the scope of the present invention is defined by the appended.
Claims (7)
1. the dimer flavone constituents in a kind of Tsuga longibracteata, it is characterised in that: its chemical name is tsugadiflavonol
A, chemical structural formula are as follows:
2. the extraction separation method of dimer flavone constituents in Tsuga longibracteata as described in claim 1, it is characterised in that including
Following steps:
1) Tsuga longibracteata bark is taken, after drying, crushing, with 70~95% alcohol at normal temperature soak extraction of volume fraction 1~4 time,
It extracts 1~10 day every time, combined extract is concentrated under reduced pressure to give ethanol extract；
2) after dispersing water for the middle gained ethanol extract of step 1), petroleum ether, ethyl acetate and extracting n-butyl alcohol 1~4 are successively used
It is secondary, it is concentrated under reduced pressure to give each position medicinal extract；
3) upper silica gel column chromatography, carries out gradient with petroleum ether-ethyl acetate after merging ethyl acetate extract medicinal extract in step 2)
Elution divides component according to polarity in conjunction with TLC detection method；
4) step 3) obtained component is crossed into preparation HPLC, with 40%~100% isocratic elution of methanol-water, is further divided into subfraction；
5) subfraction obtained in step 4) is crossed into preparation HPLC, with 40%~100% isocratic elution of methanol-water, obtains chemical combination
Object tsugadiflavonol A.
3. the extraction separation method of dimer flavone constituents in Tsuga longibracteata as claimed in claim 2, it is characterised in that step
1) it the extraction of 85~95% alcohol reflux of volume fraction 2~4 times used in, extracts 6~9 days every time.
4. the extraction separation method of dimer flavone constituents in Tsuga longibracteata as claimed in claim 2, it is characterised in that step
3) gradient elution is carried out with volume ratio 3:1,1:1,1:2,10:1 with petroleum ether-ethyl acetate in, it is different according to flavanols polarity
It is divided into 5~10 components.
5. the extraction separation method of dimer flavone constituents in Tsuga longibracteata as claimed in claim 2, it is characterised in that step
4) 45%~95% isocratic elution of methanol-water is used, 2~6 subfractions are divided into.
6. the extraction separation method of dimer flavone constituents in Tsuga longibracteata as claimed in claim 2, it is characterised in that step
5) 45%~85% isocratic elution of methanol-water used in.
7. dimer flavone constituents as described in claim 1 are in the application of anti-oxidation aspect.
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| CN108586396A (en) * | 2018-01-22 | 2018-09-28 | 遵义医学院 | - 2 (5H)-furanones of 3- (4 '-hydroxyls -3 '-methoxy-benzyl) and its extracting method |
| CN109053641B (en) * | 2018-08-22 | 2022-06-24 | 遵义医科大学 | Dineolignan compound, and separation preparation method and application thereof |
Citations (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN1594247A (en) * | 2004-06-23 | 2005-03-16 | 黑龙江省紫杉科技股份有限公司 | Yew genus plant extract and its extraction method and application |
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| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN1594247A (en) * | 2004-06-23 | 2005-03-16 | 黑龙江省紫杉科技股份有限公司 | Yew genus plant extract and its extraction method and application |
Non-Patent Citations (4)
| Title |
|---|
| Xian-Wen Yang，等.Abiesanol A, a novel biflavanol with unique six connective hexacyclic rings isolated from Abies georgei.《Tetrahedron Letters》.2008,第49卷(第19期),第3042-3044页. |
| Xian-Wen Yang，等.Mono- and Sesquiterpenoids, Flavonoids，Lignans, and Other Miscellaneous Compounds of Abies georgei.《Planta Medica》.2010,第77卷(第7期),第742-748页. |
| 常博，等.云南黄果冷杉的化学成分.《中国药科大学学报》.2014,第45卷(第1期),43-47页. |
| 肖世基，等.长苞铁杉中两个新的重排羊毛甾烷型三萜.《有机化学》.2016,第36卷1686-1689页. |
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| CF01 | Termination of patent right due to non-payment of annual fee | ||
| CF01 | Termination of patent right due to non-payment of annual fee |
Granted publication date: 20190510 |