CN108912190A - A method of preparing polymethoxyflavone, luteolin -7-O- rutinoside and rutin from Chinese wistaria - Google Patents
A method of preparing polymethoxyflavone, luteolin -7-O- rutinoside and rutin from Chinese wistaria Download PDFInfo
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- CN108912190A CN108912190A CN201810795074.7A CN201810795074A CN108912190A CN 108912190 A CN108912190 A CN 108912190A CN 201810795074 A CN201810795074 A CN 201810795074A CN 108912190 A CN108912190 A CN 108912190A
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- China
- Prior art keywords
- chinese wistaria
- luteolin
- chinese
- rutin
- polymethoxyflavone
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- IVTMALDHFAHOGL-UHFFFAOYSA-N eriodictyol 7-O-rutinoside Natural products OC1C(O)C(O)C(C)OC1OCC1C(O)C(O)C(O)C(OC=2C=C3C(C(C(O)=C(O3)C=3C=C(O)C(O)=CC=3)=O)=C(O)C=2)O1 IVTMALDHFAHOGL-UHFFFAOYSA-N 0.000 title claims abstract description 49
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- PEFNSGRTCBGNAN-QNDFHXLGSA-N luteolin 7-O-beta-D-glucoside Chemical compound O[C@@H]1[C@@H](O)[C@H](O)[C@@H](CO)O[C@H]1OC1=CC(O)=C2C(=O)C=C(C=3C=C(O)C(O)=CC=3)OC2=C1 PEFNSGRTCBGNAN-QNDFHXLGSA-N 0.000 description 1
- 150000002660 luteolin derivatives Chemical class 0.000 description 1
- 210000002540 macrophage Anatomy 0.000 description 1
- 235000009973 maize Nutrition 0.000 description 1
- 230000007246 mechanism Effects 0.000 description 1
- 230000001404 mediated effect Effects 0.000 description 1
- 230000007102 metabolic function Effects 0.000 description 1
- 230000004060 metabolic process Effects 0.000 description 1
- 239000000401 methanolic extract Substances 0.000 description 1
- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 description 1
- 230000004048 modification Effects 0.000 description 1
- 238000012986 modification Methods 0.000 description 1
- 108700026460 mouse core Proteins 0.000 description 1
- 210000003205 muscle Anatomy 0.000 description 1
- 210000004165 myocardium Anatomy 0.000 description 1
- 210000005036 nerve Anatomy 0.000 description 1
- 239000002547 new drug Substances 0.000 description 1
- MRIAQLRQZPPODS-UHFFFAOYSA-N nobiletin Chemical compound C1=C(OC)C(OC)=CC=C1C1=CC(=O)C2=C(OC)C(OC)=C(OC)C(OC)=C2O1 MRIAQLRQZPPODS-UHFFFAOYSA-N 0.000 description 1
- 230000004792 oxidative damage Effects 0.000 description 1
- 229910052760 oxygen Inorganic materials 0.000 description 1
- 239000001301 oxygen Substances 0.000 description 1
- 230000000242 pagocytic effect Effects 0.000 description 1
- 239000000575 pesticide Substances 0.000 description 1
- 238000005220 pharmaceutical analysis Methods 0.000 description 1
- ISWSIDIOOBJBQZ-UHFFFAOYSA-N phenol group Chemical group C1(=CC=CC=C1)O ISWSIDIOOBJBQZ-UHFFFAOYSA-N 0.000 description 1
- 235000013824 polyphenols Nutrition 0.000 description 1
- 230000036515 potency Effects 0.000 description 1
- 238000002360 preparation method Methods 0.000 description 1
- 238000004262 preparative liquid chromatography Methods 0.000 description 1
- 230000002265 prevention Effects 0.000 description 1
- 230000008569 process Effects 0.000 description 1
- 238000012545 processing Methods 0.000 description 1
- 108090000623 proteins and genes Proteins 0.000 description 1
- 102000004169 proteins and genes Human genes 0.000 description 1
- 238000007348 radical reaction Methods 0.000 description 1
- 235000012950 rattan cane Nutrition 0.000 description 1
- 238000011084 recovery Methods 0.000 description 1
- 230000009467 reduction Effects 0.000 description 1
- 230000001105 regulatory effect Effects 0.000 description 1
- 230000002441 reversible effect Effects 0.000 description 1
- 102000035013 scavenger receptor class A Human genes 0.000 description 1
- 108091005451 scavenger receptor class A Proteins 0.000 description 1
- 210000002966 serum Anatomy 0.000 description 1
- 238000009331 sowing Methods 0.000 description 1
- 238000012306 spectroscopic technique Methods 0.000 description 1
- 238000010183 spectrum analysis Methods 0.000 description 1
- BQMKAHQKDSZAIQ-UHFFFAOYSA-N tetrasodium;iron(3+);nitroxyl anion;pentacyanide Chemical compound [Na+].[Na+].[Na+].[Na+].[Fe+3].N#[C-].N#[C-].N#[C-].N#[C-].N#[C-].O=[N-] BQMKAHQKDSZAIQ-UHFFFAOYSA-N 0.000 description 1
- 231100000419 toxicity Toxicity 0.000 description 1
- 230000001988 toxicity Effects 0.000 description 1
- 229940126680 traditional chinese medicines Drugs 0.000 description 1
- 150000003648 triterpenes Chemical class 0.000 description 1
- 235000013311 vegetables Nutrition 0.000 description 1
- 235000019154 vitamin C Nutrition 0.000 description 1
- 239000011718 vitamin C Substances 0.000 description 1
- 108010043166 wisteria lectin Proteins 0.000 description 1
- 239000002023 wood Substances 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
- C07H17/07—Benzo[b]pyran-4-ones
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D311/00—Heterocyclic compounds containing six-membered rings having one oxygen atom as the only hetero atom, condensed with other rings
- C07D311/02—Heterocyclic compounds containing six-membered rings having one oxygen atom as the only hetero atom, condensed with other rings ortho- or peri-condensed with carbocyclic rings or ring systems
- C07D311/04—Benzo[b]pyrans, not hydrogenated in the carbocyclic ring
- C07D311/22—Benzo[b]pyrans, not hydrogenated in the carbocyclic ring with oxygen or sulfur atoms directly attached in position 4
- C07D311/26—Benzo[b]pyrans, not hydrogenated in the carbocyclic ring with oxygen or sulfur atoms directly attached in position 4 with aromatic rings attached in position 2 or 3
- C07D311/28—Benzo[b]pyrans, not hydrogenated in the carbocyclic ring with oxygen or sulfur atoms directly attached in position 4 with aromatic rings attached in position 2 or 3 with aromatic rings attached in position 2 only
- C07D311/30—Benzo[b]pyrans, not hydrogenated in the carbocyclic ring with oxygen or sulfur atoms directly attached in position 4 with aromatic rings attached in position 2 or 3 with aromatic rings attached in position 2 only not hydrogenated in the hetero ring, e.g. flavones
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D311/00—Heterocyclic compounds containing six-membered rings having one oxygen atom as the only hetero atom, condensed with other rings
- C07D311/02—Heterocyclic compounds containing six-membered rings having one oxygen atom as the only hetero atom, condensed with other rings ortho- or peri-condensed with carbocyclic rings or ring systems
- C07D311/04—Benzo[b]pyrans, not hydrogenated in the carbocyclic ring
- C07D311/22—Benzo[b]pyrans, not hydrogenated in the carbocyclic ring with oxygen or sulfur atoms directly attached in position 4
- C07D311/26—Benzo[b]pyrans, not hydrogenated in the carbocyclic ring with oxygen or sulfur atoms directly attached in position 4 with aromatic rings attached in position 2 or 3
- C07D311/40—Separation, e.g. from natural material; Purification
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- 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
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- Y—GENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
- Y02—TECHNOLOGIES OR APPLICATIONS FOR MITIGATION OR ADAPTATION AGAINST CLIMATE CHANGE
- Y02P—CLIMATE CHANGE MITIGATION TECHNOLOGIES IN THE PRODUCTION OR PROCESSING OF GOODS
- Y02P20/00—Technologies relating to chemical industry
- Y02P20/50—Improvements relating to the production of bulk chemicals
- Y02P20/54—Improvements relating to the production of bulk chemicals using solvents, e.g. supercritical solvents or ionic liquids
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- Chemical & Material Sciences (AREA)
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- Health & Medical Sciences (AREA)
- Life Sciences & Earth Sciences (AREA)
- Engineering & Computer Science (AREA)
- Biochemistry (AREA)
- Biotechnology (AREA)
- General Health & Medical Sciences (AREA)
- Genetics & Genomics (AREA)
- Molecular Biology (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Abstract
The method that the invention discloses a kind of to prepare polymethoxyflavone, luteolin -7-O- rutinoside and rutin from Chinese wistaria, including Chinese wistaria material is dried, is crushed, extracted dose of extraction, crude extract is obtained after separation of solid and liquid, then purified obtains polymethoxyflavone, luteolin -7-O- rutinoside and rutin.The method of the present invention is at low cost, and repeatability is strong, and extraction efficiency is high, and originating species Chinese wistaria is used as the raw material for preparing polymethoxyflavone and luteolin -7-O- rutinoside and rutin, resourceful, can largely plant, biomass is big, production cost is low.
Description
Technical field
The invention discloses one kind to prepare polymethoxyflavone, luteolin -7-O- rutinoside and rutin from Chinese wistaria
Method, belong to Chinese wistaria extract technical field.
Background technique
Chinese wistaria also known as Zhu rattan, Chinese wistaria are leguminous plant, originate in China, common with Ji, Shanxi, Shandong, Henan and other places.Chinese wistaria removes
Ornamental outer, its flower, cauline leaf, root, seed can all be used as medicine.Chinese wistaria cauline leaf 7- containing luteolin glucose rhamnoside, apiolin
With the ingredients such as vitamin C, have the effect of removing toxicity for detumescence (Han De holds Chinese wistaria [J] China traditional Chinese medicine report, 2012.8:1).In river
South, Hebei, one band of Shandong, people often adopt wistaria flower steamed wheaten foods, and faint scent is delicious.Pekinese's purple trailing plants cake and the Chinese wistaria cake in some places,
Chinese wistaria congee, fried Chinese wistaria fish etc. all employ wistaria flower (Chinese wistaria:Tradition and the friend of cuisines [J] the farmers' of fashion, 2016 (7):60-
61.)。
Chinese wistaria is very wide in Chinese application, and garden, park, campus of north and south various regions etc. can see the figure of Chinese wistaria.Chinese wistaria
In China, Japan and American-European countries mainly as ornamental plants in garden, American-European Chinese wistaria be mainly in short fringe kind.Chinese wistaria kind is pressed
Pink colour system, white color system, violet and yellow class can be divided into according to pattern.
Chinese wistaria is primary in barren hill, twines and ties up on arbor limb, therefore is usually used in garden, urban green space, sightseeing scenic spot
Deng (Jin Wendong, the refined Chinese wistaria assortment of scholar Lu and application form [J] Chinese flower gardening, 2017.6:36-37).Chinese wistaria
It plants or basin plant is ok, and is adaptable, manage very well.The breeding of Chinese wistaria has the side such as sowing, cuttage, press strip, plant division, grafting
Method.But because seedling growth is slower, so generally using cuttage for the (cultivation and purposes of Zhou little Juan Chinese wistaria of main modes of reproduction
[J] Exploitation of Agriculture in Heilongjiang science, 2012 (1):162-163).
Wistaria contains the ingredients such as phenolic acid class, flavonoids, agglutinin, and (Fu Maorun, Wang Xiao, Chen Qingmin wait wistaria flower to extract
Antioxidation [J] food and fermentation industries of object, 2009,35 (12):The effect and application of 82-85./Zhu Yue agglutinin
[J] aquatic science, 2005,24 (12):48-49).Phenolic acid, flavone compound in wistaria flower can not only remove oxygen
Change the free radical of the reaction chain stage of reaction, and can directly capture the free radical in free radical reaction chain, blocks free radical chain
Reaction, to play a dual role of prevention and chain rupture, (Fu Maorun, Wang Xiao, Chen Qingmin wait the anti-oxidant of Chinese wistaria flower extract
Act on [J] food and fermentation industries, 2009,35 (12):82-85).The Pleurotus Ostreatus substance extracted in Chinese wistaria, it is solidifying with plant
Influence sugar transportation common to collection element, the accumulation of stored substance and fissional regulating and controlling effect, in clinical immunization and cell
Have in genetic research good application prospect (Chen Fan, Chen Haifang, Fu Jun Chinese wistaria agglutinin isolate and purify and physicochemical property is ground
Study carefully the botany research of the Wuhan [J], 1994,12 (3):270-276)(Cant N B,Benson C G.Wisteria
floribunda lectin is associated with specilic cell types in the wentral
cochlear nucleus of the gerbil,Meriones unguiculatus[J].Hearing Research,
2006,6(216):64-72).Jiang Yanhua etc. is soft to muskmelon wilt disease and Chinese cabbage using Chinese wistaria leaf acetone solvent extracting solution as raw material
Maize ear rot carries out bacteriostatic experiment, and fungistatic effect is best when discovery extract concentrations are 0.1g, shows the acetone extract pair of Chinese wistaria leaf
The growth of fungi and bacterium has bacteriostasis, is expected to be developed (Jiang Yanhua, Fan Xiao as a kind of novel plant source biological pesticide
Sunshine, the extraction of Jiang Hua Chinese wistaria active constituent and bacteriostasis pre-test [J] Henan Agricultural Sciences, 2009 (3):60-62,78).
The researchs such as Mona report, using acid-hydrolysis method, spectrum analysis, Electrospray Ionization Mass Spectrometry and two dimensional NMR method to Chinese wistaria
Chrysomelid alcohol extract carries out chromatography, finds there is 6 kinds of flavone compounds, 2 kinds of triterpene aglycons and a kind of new acylation in Chinese wistaria
Flavonoid glycoside compound.And show 80% methanol extract liquid of Chinese wistaria leaf of degreasing in addition to anti-oxidant by biological study
Activity, there are also apparent cytotoxic activity (Mona AM, Manal M H, Allia M A, et al.Antioxidant and
cytotoxic constituents from Wisteria sinensis[J].Molecules,2011,16(5):4020-
4030).Song Xiao etc. analyzes the possible chemical component of Chinese wistaria root, stem and leaf, primarily determines in Chinese wistaria root, stem and leaf containing biology
The Multiple components such as alkali, flavonoids, protein, sugar and glycoside (the pre- reality of Song Xiao, Jiang Guoliang, Zhao Xue plum Chinese wistaria root, stem and leaf chemical component
Test [J] Taishan Hospital journal .2013,34 (11):832-835).There is no indication that specific substance.Chinese wistaria tumor ethanol extract
With preferable antifungal activity, (Wu Peiyun, Liu Jingsong, Chen Aimin, clock is civil and military, Wang Gang Chinese wistaria tumor extract disease-resistant fungal pathogen
Activity research [J] Chinese patent drug, 2012,10,34 (10):2018-2020).
Compared with Chinese Chinese wistaria, Australia Chinese wistaria blade is more thick and solid, and seed is bigger, and weight is the 6-10 of Chinese Chinese wistaria seed
Times, Chinese Chinese wistaria seed is thin oblateness, and Australia Chinese wistaria seed is cylindrical or ellipse, and kind of pod is also very big, leaf-making quantity,
Seed weight and kind pod weight and all more advantageous than Chinese Chinese wistaria to the resistance of reverse of environment are more suitable for work in addition to ornamental
The raw material sources that industry is extracted.
Chinese wistaria contains luteolin, is natural flavonoid compound, and the plant rich in luteolin is used frequently as Chinese medicine
Disease is treated, there is multiple pharmacological effect.Luteolin and its glucosides have anti-dementia, and (Jiang Ruizhi, Gao Qipin, used as a personal name in ancient times high-ranking official wait
Purposes of luteolin -7-O- β-D glucose (1 → 2) glucoside in preparation treatment dementia disease drug:China,
CN101292989A [P] .2008-10-29), antibacterial (Salawu S O, Ogundare A O, Ola-Salawu B B, et
al.Antimicrobial activities of phenolic containing extracts of some tropical
vegetables[J].Afr J Pharm Pharmacol,2011,5(4):486-492), anticancer (Orhan F, BarisO,
Yanmis D,et al.Isolation of some luteolin derivatives from Mentha longifolia
(L.)Hudson subsp.longifolia and determination of their genotoxic potencies
[J].Food Chem,2012,135(2):764-769), (in tinkling of pieces of jades, Wang Xuedong, Wang Songlin wait sweet-scented osmanthus for cardiovascular and cerebrovascular protection
Careless element -7-O- β-D-Glucose aldehydic acid glycosides treatment cerebral infarction purposes:, CN 102327281 A [P] .2012.) the effects of.But
It is lower in natural plants kind content, although luteolin and its glucoside have preferable pharmacological activity, they and it is big
Part flavone compound is equally insoluble in water, and oral absorption is difficult, and bioavilability is lower, and clinical application is restricted (Lee
Bright quiet, Zhang Li, Zhao Dongbao wait luteolin -7-O- β-solubilized behavior of the D-Glucose glycosides in several molecule aggregate systems to grind
Study carefully [J] chemistry journal, 2009,67 (17):1950-1956).And luteolin -7-O- rutinoside is water-soluble, is soluble in
Hot water, better than luteolin and luteolin -7-O- glucoside, (Wen Yongju, Shen is beautiful, clean luteolin -7-O- rue
Semi-synthetic [J] the Chinese patent drug of glucosides, 2015.12,37 (12):2790-2794).
Rutin is typical natural flavonoid compound, has multiple pharmacological effect.Rutin is to Type I diabetes mouse cardiac muscle
Damage has protective effect, and (Ji Xiaoru explains refined fine jade, and Li Congwei, Cao Haoxuan, Gong Biao, Bai Jing rutin is to Type I diabetes mouse core
Influence [J] North China Polytechnics's journal (medicine) of injury of muscle, 2017.1,19 (1):5-8), have to acute lung injury and protect
(then, Xia Zhongyuan, Meng Qing great waves rutin induced by endotoxin induces protective effect [J] of acute lung injury model mouse to Chen Zhi for shield effect
Chinese medicine journal, 2018.2.1,33 (2):209-213).It is big that rutin can reduce diabetes B in 50-200mg/kg dosage range
Mouse blood glucose, blood lipid, and renal function can be improved, (seedling related to AngII, VEGF effect in serum that reduces to the protection mechanism of kidney
Build red, Bai Jing, Li Xiang, influence [J] herbal pharmacology of the Zhang Zhi rutin to diabetes B rat glycolipid metabolism and renal function with face
Bed, 2014,30 (6):48-50).Rutin has significant protective effect to the damage of sodium nitroprussiate inducing nerve cell, and nerve is protected
Shield effect may be by (Zhang Lang, Lai Wangchang, great waves, Wang Kang, Meng Qian, the Zheng Wenhua rutin of ERK1/2 signal path mediation
To protective effect [J] Chinese medicine of nerve cell oxidative damage, 2014.4,37 (4):640-644).
Polymethoxyflavone (MPF) is considered in the past specific to a variety of tangerine class plants of Rutaceae, especially in its fruit
There is higher content in skin.It is less to the research of polymethoxyflavone compound, in recent years due to its excellent activity, especially
The research of anticancer activity has made great progress that (Wu Hongwei, Lei Haimin, Li Qiang wait the more first of Pericarpium Citri Reticulatae by HPLC
Content [J] Pharmaceutical Analysis magazine of 3 kinds of flavones, 2007,27 (12) in oxygroup flavones position:1895；Xiao Wang,Fuwei
Li,Hongxia Zhang,et al.Preparative isolation and purification of poly-
methoxylated flavones from Tangerine peel using high speed counter current
chromato-graphy[J].J Chromatography A,2005,1090:188)(Wang Dandan,Wang Jian,
Huang Xuehui,et al.Identification of poly-methoxylated flavones from green
tangerine peel(Pericarpium Citri Reticulatae Viride)by chromatographic and
spectroscopic techniques[J].J Pharm Biomed Anal,2007,44:63).Since Polymethoxylated class is yellow
Ketone compound has stronger inhibiting effect to a variety of cancer cells, by extensive concern both domestic and external.Both at home and abroad to Polymethoxylated Huang
The anticancer activity report of ketones component is more and more, this constituents is prompted to have potential new drug development value (Han Jindan, Wang Kui
Force, Shen Lianqing, when treasure's dried immature fruit of citron orange in polymethoxyflavone class compound research [J] traditional Chinese medical science traditional Chinese medicines, 2010,21 (10):2469-
2470) (Chen Shengmin, Dong Yang polymethoxyflavone Advances in antitumor activity [J] Chinese Pharmacological Bulletin, 2017.11,33
(11):1493-1495)。
Some researches show that substances containing polymethoxyflavone in orange peel, in anticancer, reduce cholesterol, anti-oxidant, anti-inflammatory etc.
Aspect have significant bioactivity (single poplar citrus processing technology research and industrialization development [J] Chinese food journal,
2006,6(1):423-428)(Whitman SC,Kurowska EM,Manthey J A,et al.Nobiletin,a
citrus flavonoid isolated from tangerines,selectively inhibits class A
scavenger receptor-mediated metabolism of acetylated LDL by mouse macrophages
[J].Atherosclerosis,2005,178(1):25-32).The cardiovascular diseases such as atherosclerosis have become in recent years
One of maximum healthy hidden danger of the mankind, high cholesterol and inflammation are two of them main causes.Polymethoxyflavone has reduction
The sp act of cholesterol and anti-inflammatory is the only selection for producing functional health product.(Li Chengping, Rao Guiwei, Tian Hongmei,
Mei Yu, Yan little Ping, active high speed adverse current chromatogram separation prepare polymethoxyflavone in orange peel [J] Chinese food journal,
2015.6,15(6):117-122)。
In 5- methoxy flavone, with hydroxyl -6,7,8,3', 4'- pentamethoxyl flavones, 5,3'- dihydroxy -6,7,8,4'-
The effect of pentamethoxyl flavones is unique, has induction of differentiation to the bone marrow leukemia cells (M1 cell) of laboratory mice, and
Enhance its phagocytic function (Sugiyama S, Umehara K, Kuroyangi M, et al.Studies on the
differentiation inducer of myeloid leukemic cells from Citrus species.Chem
Pharm Bull, 1993,41,714), therefore both compounds have apparent value of exploiting and utilizing.
Pan Fusheng et al., which is provided, to be extracted content and is higher than more than 80% methoxy in a kind of fruit from rue family citrus plant
The method of base flavones.A kind of (method that polymethoxyflavone is extracted from plants of Pan Fusheng, Ye Shan:China, CN 1683361
A[P].2005.10.19).Zhao Li qin et al. invents a kind of simple process, and recovery rate is high to extract general flavone from wistaria flower
Method (Zhao Liqin, Yan Guilong, Wang Wei .CN105748569A [P] .2016.07.13).
Therefore, polymethoxyflavone, luteolin -7-O- rutinoside and rutin application value with higher, still
Limited source at present, and polymethoxyflavone, luteolin -7-O- rutinoside and rutin are extracted from Chinese wistaria without discovery
Correlative study.
Summary of the invention
Goal of the invention：In view of the above technical problems, the present invention provides one kind prepares polymethoxyflavone, wood from Chinese wistaria
The method of rhinoceros grass element -7-O- rutinoside and rutin, this method is at low cost, and repeatability is strong, and extraction efficiency is high.
Technical solution：To achieve the above object of the invention, the present invention uses following technical scheme：
A method of preparing polymethoxyflavone, luteolin -7-O- rutinoside and rutin from Chinese wistaria, including will
The drying of Chinese wistaria material crushes, and extracted dose of extraction obtains crude extract after separation of solid and liquid, then purified obtains Polymethoxylated Huang
Ketone, luteolin -7-O- rutinoside and rutin.
The Chinese wistaria plant origin, including but not limited to Australia Chinese wistaria, Chinese Chinese wistaria (Wisteria sinensis), day
The Chinese wistarias platymisciums such as this Chinese wistaria (Wisteria floribunda), American-European Chinese wistaria.
The Chinese wistaria material is one or more of positions such as stem, leaf, fruit, fruit pod, flower, Chinese wistaria tumor or the root of Chinese wistaria.
The extractant is one of water, methanol, ethyl alcohol, acetone, n-butanol, ethyl acetate or a variety of different proportions
Mixed liquor.
The pH of the extractant is 3.0~9.0, volumetric concentration 30-70%, and the solid-liquid ratio of raw material and extractant is 1：10
~1：50 (w/v), extraction time be 0.1~20h, 30 DEG C~70 DEG C of Extracting temperature.Optimum condition is：Extraction time be 1~
20h, 40 DEG C~70 DEG C of Extracting temperature；Preferred condition is：PH is 6.0, solid-liquid ratio 1：10, extraction time 2h are extracted
Temperature 60 C, Extraction solvent are 70% ethyl alcohol.
The extracting mode is that water-bath extraction, ultrasound assisted extraction, microwave radiation exaraction, superhigh pressure technique are extracted or super faced
The combination of one of boundary's fluid extraction or a variety of methods.
The obtained polymethoxyflavone of purifying is 5,6,7,3', 4'- pentamethoxyl flavones, 5- hydroxyl -6,7,8,3',
4'- pentamethoxyl flavones, 5,6,7,8,4'- pentamethoxyl flavones, dihydroxy tetramethoxy flavones have dihydroxy -6,7 5,3'-,
One of 8,4'- pentamethoxyl flavones or Multiple components.
The purifying material therefor is that polyamide, macroreticular resin, preparative liquid chromatogram, high performance countercurrent chromatography or ion are handed over
Colour changing is composed one or more.Eluant, eluent is the ethanol water of various concentration, under 30% ethyl alcohol 2BV (2 times of column volumes) elution
To be luteolin -7-O- rutinoside, it is rutin that 40% ethyl alcohol 3BV, which is eluted, what 50% ethyl alcohol 2BV was eluted
For polymethoxyflavone.
Technical effect：The content of polymethoxyflavone is Polymethoxylated in 0.4mg/g or so, Fructus Aurantii in traditional Bauhinia champloni
The content of flavones content polymethoxyflavone in 0.4mg/g or so, kamuning is come in 10mg/g or so with these traditional plants
Source is compared, and Chinese wistaria especially Australia Chinese wistaria (content containing polymethoxyflavone is in 0.2mg/g), which is used as, prepares polymethoxyflavone, with
And the raw material of luteolin -7-O- rutinoside and rutin, it is resourceful, it can largely plant, biomass is big, production cost is low.
Detailed description of the invention
Fig. 1：The method of the present invention extracts the extracting solution HPLC figure of Australia Chinese wistaria leaf.
Fig. 2：The first mass spectrometric figure of the luteolin -7-O- rutinoside of the extracted separation of the method for the present invention.
Fig. 3：The first mass spectrometric figure of the rutin of the extracted separation of the method for the present invention.
Fig. 4：The first mass spectrometric figure of the 5,6,7,3' of the extracted separation of the method for the present invention, 4'- pentamethoxyl flavones.
Fig. 5：The first mass spectrometric of 5- hydroxyl -6,7,8,3', 4'- the pentamethoxyl flavones of the extracted separation of the method for the present invention
Figure.
Fig. 6：The first mass spectrometric figure of the 5,6,7,8,4'- pentamethoxyl flavones of the extracted separation of the method for the present invention.
Fig. 7：The first mass spectrometric of the 5,3'- dihydroxy -6,7,8,4'- pentamethoxyl flavones of the extracted separation of the method for the present invention
Figure.
Specific embodiment
With reference to the accompanying drawing and specific example, the present invention is furture elucidated, it should be understood that these embodiments are merely to illustrate this
Invention is not intended to limit the scope of the invention, and after the present invention has been read, those skilled in the art are to of the invention various etc.
The modification of valence form falls within the application range as defined in the appended claims.
Embodiment 1
Dry Australia Chinese wistaria leaf 1000g is weighed, crushed 50 meshes, solid-to-liquid ratio is according to 1：PH3.0 volume is added in 20 (w/v)
60% ethanol solution of concentration extracts 1h under ultrasonication, 50 DEG C of Extracting temperature after being separated by solid-liquid separation, obtain containing Polymethoxylated Huang
The extracting solution of ketone.Wherein the total amount of polymethoxyflavone is 0.22g.After purification through polyamide column, eluant, eluent is various concentration
Ethanol water, it is luteolin -7-O- rutinoside, 40% ethyl alcohol that 30% ethyl alcohol 2BV (2 times of column volumes), which is eluted,
It is rutin that 3BV, which is eluted, and it is polymethoxyflavone that 50% ethyl alcohol 2BV, which is eluted, obtains more first that purity is 95%
Oxygroup flavones 0.14g, luteolin -7-O- rutinoside 0.46g and rutin 0.25g.
The HPLC figure of said extracted liquid is shown in Fig. 1, it can be seen that luteolin -7-O- rutinoside is in extracting solution
Peak area is the largest, and is significantly higher than other peaks, percentage composition 9%, therefore its extraction and application has big advantage；This
Outside.In addition, rutin is only second to luteolin -7-O- rutinoside in extracting solution peak area, the 3.7% of total peak area is accounted for, and
It is worth isolated composition.
Fig. 2 is the first mass spectrometric figure at No. 1 peak in Fig. 1, by parsing it as luteolin -7-O- rutinoside；
Fig. 3 is the first mass spectrometric figure at No. 2 peaks in Fig. 1, by parsing it as rutin；
Fig. 4 is the first mass spectrometric figure at No. 3 peaks in Fig. 1, by parsing it as 5,6,7,3', 4'- pentamethoxyl flavones；
Fig. 5 is the first mass spectrometric figure at No. 4 peaks in Fig. 1, and by parsing it as 5- hydroxyl -6,7,8,3', 4'- pentamethoxyl is yellow
Ketone；
Fig. 6 is the first mass spectrometric figure at No. 5 peaks in Fig. 1, by parsing it as 5,6,7,8,4'- pentamethoxyl flavones；
Fig. 7 is the first mass spectrometric figure at No. 6 peaks in Fig. 1, is 5,3'- dihydroxy -6,7,8,4'- pentamethoxyls by parsing it
Flavones；
Embodiment 2
Change Australia Chinese wistaria leaf in embodiment 1 into Chinese Chinese wistaria leaf, other conditions are constant.
Embodiment 3
Change Australia Chinese wistaria leaf in embodiment 1 into Japanese Chinese wistaria leaf, other conditions are constant.
Embodiment 4
Dry Australia Chinese wistaria leaf 1000g is weighed, crushed 50 meshes, solid-to-liquid ratio is according to 1：PH5.0 volume is added in 10 (w/v)
70% methanol solution of concentration, water-bath effect is lower to extract 3h, 40 DEG C of Extracting temperature, after being separated by solid-liquid separation, obtains containing Polymethoxylated
The extracting solution of flavones.Wherein the total amount of polymethoxyflavone is 0.18g.After macroporous resin purification, eluant, eluent is various concentration
Ethanol water, it is luteolin -7-O- rutinoside, 40% ethyl alcohol that 30% ethyl alcohol 2BV (2 times of column volumes), which is eluted,
It is rutin that 3BV, which is eluted, and it is polymethoxyflavone that 50% ethyl alcohol 2BV, which is eluted, obtains more first that purity is 90%
Oxygroup flavones 0.11g.Luteolin -7-O- rutinoside 0.45g and rutin 0.2g.
Embodiment 5
Change Australia Chinese wistaria leaf in embodiment 4 into Chinese Chinese wistaria leaf, other conditions are constant.
Embodiment 6
Change Australia Chinese wistaria leaf in embodiment 4 into American-European Chinese wistaria leaf, other conditions are constant.
Embodiment 7
Dry Australia wistaria flower 1000g is weighed, dries pulverizing crosses 50 meshes, and solid-to-liquid ratio is according to 1：PH6.0 is added in 30 (w/v)
50% solution of volumetric concentration extracts 5h under microwave action, and 70 DEG C of Extracting temperature after being separated by solid-liquid separation, obtain containing Polymethoxylated Huang
The extracting solution of ketone.Wherein the total amount of polymethoxyflavone is 0.19g.After purification through high performance countercurrent chromatography, eluant, eluent is different dense
The ethanol water of degree, it is luteolin -7-O- rutinoside, 40% second that 30% ethyl alcohol 2BV (2 times of column volumes), which is eluted,
It is rutin that alcohol 3BV, which is eluted, and it is polymethoxyflavone that 50% ethyl alcohol 2BV, which is eluted, obtain purity be 85% it is more
Methoxy flavone 0.11g.Luteolin -7-O- rutinoside 0.36g and rutin 0.25g.
Embodiment 8
Change Australia wistaria flower in embodiment 7 into Chinese wistaria flower, other conditions are constant.
Embodiment 9
Change Australia wistaria flower in embodiment 7 into Japanese wistaria flower, other conditions are constant.
Embodiment 10
Dry Australia Chinese wistaria fruit 1000g is weighed, dries pulverizing crosses 50 meshes, and solid-to-liquid ratio is according to 1：PH7.0 is added in 50 (w/v)
70% acetone soln of volumetric concentration extracts 10h, 40 DEG C of Extracting temperature, after being separated by solid-liquid separation, obtains containing more first under ultrasonication
The extracting solution of oxygroup flavones.Wherein the total amount of polymethoxyflavone is 0.17g.After preparative liquid chromatography purification, eluant, eluent
For the ethanol water of various concentration, it is luteolin -7-O- rutinose that 30% ethyl alcohol 2BV (2 times of column volumes), which is eluted,
Glycosides, it is rutin that 40% ethyl alcohol 3BV, which is eluted, and it is polymethoxyflavone that 50% ethyl alcohol 2BV, which is eluted, obtains purity and is
90% polymethoxyflavone 0.09g.Luteolin -7-O- rutinoside 0.28g and rutin 0.22g.
Embodiment 11
Change Australia Chinese wistaria fruit in embodiment 10 into Chinese Chinese wistaria fruit, other conditions are constant.
Embodiment 12
Change Australia Chinese wistaria fruit in embodiment 10 into American-European Chinese wistaria fruit, other conditions are constant.
Embodiment 13
Dry Australia Chinese wistaria stem 1000g is weighed, dries pulverizing crosses 50 meshes, and solid-to-liquid ratio is according to 1：PH8.0 is added in 20 (w/v)
60% butanol solution of volumetric concentration extracts 1h, 45 DEG C of Extracting temperature, after being separated by solid-liquid separation, obtains containing more under ultrasonication
The extracting solution of methoxy flavone.Wherein the total amount of polymethoxyflavone is 0.21g.After ion-exchange chromatogram purification, eluant, eluent
For the ethanol water of various concentration, it is luteolin -7-O- rutinose that 30% ethyl alcohol 2BV (2 times of column volumes), which is eluted,
Glycosides, it is rutin that 40% ethyl alcohol 3BV, which is eluted, and it is polymethoxyflavone that 50% ethyl alcohol 2BV, which is eluted, obtains purity and is
90% polymethoxyflavone 0.12g.Luteolin -7-O- rutinoside 0.27g and rutin 0.18g.
Embodiment 14
Change Australia Chinese wistaria stem in embodiment 13 into Chinese Chinese wistaria stem, other conditions are constant.
Embodiment 15
Change Australia Chinese wistaria stem in embodiment 13 into Japanese Chinese wistaria stem, other conditions are constant.
Embodiment 16
Dry Australia Chinese wistaria tumor 1000g is weighed, dries pulverizing crosses 50 meshes, and solid-to-liquid ratio is according to 1：PH9.0 is added in 30 (w/v)
70% ethyl alcohol alcoholic solution of volumetric concentration, supercritical extract effect is lower to extract 12h, 65 DEG C of Extracting temperature, after being separated by solid-liquid separation, obtains
To the extracting solution containing polymethoxyflavone.Wherein the total amount of polymethoxyflavone is 0.18g.After macroporous resin purification, elution
Agent is the ethanol water of various concentration, and it is luteolin -7-O- rue that 30% ethyl alcohol 2BV (2 times of column volumes), which is eluted,
Glucosides, it is rutin that 40% ethyl alcohol 3BV, which is eluted, and it is polymethoxyflavone that 50% ethyl alcohol 2BV, which is eluted, obtains purity
For 85% polymethoxyflavone 0.11g.Luteolin -7-O- rutinoside 0.32g and rutin 0.22g.
Embodiment 17
Change Australia Chinese wistaria tumor in embodiment 16 into Chinese Chinese wistaria tumor, other conditions are constant.
Embodiment 18
Change Australia Chinese wistaria tumor in embodiment 16 into Japanese Chinese wistaria tumor, other conditions are constant.
Embodiment 19
Dry Australia Chinese wisteria root 1000g is weighed, dries pulverizing crosses 50 meshes, and solid-to-liquid ratio is according to 1：PH9.0 is added in 10 (w/v)
60% methanol solution of volumetric concentration, supercritical extract effect is lower to extract 20h, 55 DEG C of Extracting temperature, after being separated by solid-liquid separation, obtains
Extracting solution containing polymethoxyflavone.Wherein the total amount of polymethoxyflavone is 0.20g.After polyamide purifying, eluant, eluent is
The ethanol water of various concentration, it is luteolin -7-O- rutinoside that 30% ethyl alcohol 2BV (2 times of column volumes), which is eluted,
It is rutin that 40% ethyl alcohol 3BV, which is eluted, and it is polymethoxyflavone that 50% ethyl alcohol 2BV, which is eluted, obtains purity and is
85% polymethoxyflavone 0.14g.Luteolin -7-O- rutinoside 0.42g and rutin 0.22g.
Embodiment 20
Change Australia Chinese wisteria root in embodiment 19 into Chinese Chinese wisteria root, other conditions are constant.
Embodiment 21
Change Australia Chinese wisteria root in embodiment 19 into Japanese Chinese wisteria root, other conditions are constant.
Embodiment 22
Dry Australia Chinese wistaria fruit pod 1000g is weighed, dries pulverizing crosses 50 meshes, and solid-to-liquid ratio is according to 1：20 (w/v) are added
30% butanol solution of pH5.0 volumetric concentration, extraction 10h under ultrahigh pressure liquid phase effect, 45 DEG C of Extracting temperature, through being separated by solid-liquid separation
Afterwards, the extracting solution containing polymethoxyflavone is obtained.Wherein the total amount of polymethoxyflavone is 0.16g.Through preparative liquid chromatogram
After purification, eluant, eluent is the ethanol water of various concentration, and it is reseda that 30% ethyl alcohol 2BV (2 times of column volumes), which is eluted,
Element -7-O- rutinoside, it is rutin that 40% ethyl alcohol 3BV, which is eluted, and it is Polymethoxylated Huang that 50% ethyl alcohol 2BV, which is eluted,
Ketone obtains the polymethoxyflavone 0.08g that purity is 85%.Luteolin -7-O- rutinoside 0.38g and rutin 0.21g.
Embodiment 23
Change Australia Chinese wistaria fruit pod in embodiment 22 into Chinese Chinese wistaria fruit pod, other conditions are constant.
Embodiment 24
Change Australia Chinese wistaria fruit pod in embodiment 22 into Japanese Chinese wistaria fruit pod, other conditions are constant.
Extracting solution obtained by Example 2-24 and compound carry out HPLC and Mass Spectrometer Method, verifying according to 1 method of embodiment
Gained compound be luteolin -7-O- rutinoside, rutin, 5,6,7,3', 4'- pentamethoxyl flavones, hydroxyl -6,7,8 5-,
3', 4'- pentamethoxyl flavones, 5,6,7,8,4'- pentamethoxyl flavones and 5,3'- dihydroxy -6,7,8,4'- pentamethoxyl are yellow
Ketone.
Claims (7)
1. a kind of method for preparing polymethoxyflavone, luteolin -7-O- rutinoside and rutin from Chinese wistaria, feature exist
In, including by the drying of Chinese wistaria material, crush, extracted dose of extraction obtains crude extract after separation of solid and liquid, then it is purified obtain it is more
Methoxy flavone, luteolin -7-O- rutinoside and rutin.
2. according to claim 1 prepare polymethoxyflavone, luteolin -7-O- rutinoside and rutin from Chinese wistaria
Method, which is characterized in that the Chinese wistaria is Australia Chinese wistaria, Chinese Chinese wistaria, Japanese Chinese wistaria or American-European Chinese wistaria.
3. according to claim 1 prepare polymethoxyflavone, luteolin -7-O- rutinoside and rutin from Chinese wistaria
Method, which is characterized in that the Chinese wistaria material is one of the stem of Chinese wistaria, leaf, fruit, fruit pod, flower, Chinese wistaria tumor or root position
Or it is several.
4. according to claim 1 prepare polymethoxyflavone, luteolin -7-O- rutinoside and rutin from Chinese wistaria
Method, which is characterized in that the extractant be one of water, methanol, ethyl alcohol, acetone, n-butanol, ethyl acetate or a variety of
The mixed liquor of different proportion.
5. according to claim 1 prepare polymethoxyflavone, luteolin -7-O- rutinoside and rutin from Chinese wistaria
Method, which is characterized in that the pH of the extractant be 3.0~9.0, volumetric concentration 30-70%, the material of raw material and extractant
Liquor ratio is 1：10~1：50 (w/v), extraction time be 0.1~20h, 30 DEG C~70 DEG C of Extracting temperature.
6. according to claim 1 prepare polymethoxyflavone, luteolin -7-O- rutinoside and rutin from Chinese wistaria
Method, which is characterized in that the extracting mode be water-bath extraction, ultrasound assisted extraction, microwave radiation exaraction, superhigh pressure technique
One of extraction or supercritical fluid extraction or the combination of a variety of methods.
7. according to claim 1 prepare polymethoxyflavone, luteolin -7-O- rutinoside and rutin from Chinese wistaria
Method, which is characterized in that the purifying material therefor is polyamide, macroreticular resin, preparative liquid chromatogram, high performance counter current color
Spectrum or ion-exchange chromatography it is one or more.
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Cited By (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN109734754A (en) * | 2019-01-29 | 2019-05-10 | 重庆工商大学 | A kind of method that complex enzyme catalytic activation mulberry leaf obtain through refining high-purity rutoside |
| CN110179851A (en) * | 2019-06-24 | 2019-08-30 | 中南民族大学 | Wistaria flower general flavone active site and preparation method thereof, the pharmaceutical composition and application for preventing and treating diabetes |
Citations (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN105748569A (en) * | 2016-03-31 | 2016-07-13 | 淮阴师范学院 | Extracting and separating method of total flavones of wisteria flowers |
-
2018
- 2018-07-19 CN CN201810795074.7A patent/CN108912190A/en active Pending
Patent Citations (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN105748569A (en) * | 2016-03-31 | 2016-07-13 | 淮阴师范学院 | Extracting and separating method of total flavones of wisteria flowers |
Non-Patent Citations (6)
| Title |
|---|
| ABDELAZIZ M. DAWIDAR，等: "New Flavone Glycoside from Wisteria sinensis.", 《RESEARCH JOURNAL OF PHARMACEUTICAL, BIOLOGICAL AND CHEMICAL SCIENCES》 * |
| MEGUMI ONO，等: "Quantitative Flavonoid Variation Accompanied by Change of Flower Colors in Edgeworthia chrysantha, Pittosporum tobira and Wisteria floribunda", 《NATURAL PRODUCT COMMUNICATIONS》 * |
| MONA A. MOHAMED，等: "Antioxidant and Cytotoxic Constituents from Wisteria sinensis", 《MOLECULES》 * |
| 丁兆青: "紫藤化学成分分析及抑菌活性研究", 《安徽农业大学硕士学位论文》 * |
| 吴培云，等: "紫藤瘤化学成分研究（II）", 《中药材》 * |
| 韩金旦，等: "枳实中多甲氧基黄酮类化合物的研究", 《时珍国医国药》 * |
Cited By (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN109734754A (en) * | 2019-01-29 | 2019-05-10 | 重庆工商大学 | A kind of method that complex enzyme catalytic activation mulberry leaf obtain through refining high-purity rutoside |
| CN110179851A (en) * | 2019-06-24 | 2019-08-30 | 中南民族大学 | Wistaria flower general flavone active site and preparation method thereof, the pharmaceutical composition and application for preventing and treating diabetes |
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