CN103524347B - Samara chrysanthemum is the method that raw material extracts chicoric acid, monocaffeyltartaric acid, 3,5-dicaffeoyl-quinic acid and chlorogenic acid simultaneously - Google Patents
Samara chrysanthemum is the method that raw material extracts chicoric acid, monocaffeyltartaric acid, 3,5-dicaffeoyl-quinic acid and chlorogenic acid simultaneously Download PDFInfo
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- CN103524347B CN103524347B CN201310442563.1A CN201310442563A CN103524347B CN 103524347 B CN103524347 B CN 103524347B CN 201310442563 A CN201310442563 A CN 201310442563A CN 103524347 B CN103524347 B CN 103524347B
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- acid
- chicoric
- monocaffeyltartaric
- dicaffeoyl
- samara chrysanthemum
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C67/00—Preparation of carboxylic acid esters
- C07C67/48—Separation; Purification; Stabilisation; Use of additives
Abstract
To the invention discloses with Pterocypsela plant as raw material, extract chicoric acid, monocaffeyltartaric acid, the method for 3,5-dicaffeoyl-quinic acid and chlorogenic acid simultaneously.By samara chrysanthemum with after extraction (also using ultrasonic, microwave radiation exaraction), wherein chicoric acid, monocaffeyltartaric acid, the extracted amount of 3,5-dicaffeoyl-quinic acid and chlorogenic acid four kinds of compositions is the highest can be reached 25.3mg/g, 3.62mg/g, 6.0mg/g, 3.6mg/g. respectively wherein chicoric acid content is the highest.Samara chrysanthemum can be used as the raw material extracting these natural products.Enforcement of the present invention is the effective utilization to samara chrysanthemum, and the samara chrysanthemum of removing as weeds is become the raw material that can initiatively utilize, and for Appropriate application samara chrysanthemum provides scientific basis, has the feature of aboundresources, process green.
Description
Technical field
The present invention relates to plant is that raw material extracts the method preparing effective constituent, is specifically related to from samara chrysanthemum, extract chicoric acid, monocaffeyltartaric acid, the method for 3,5-dicaffeoyl-quinic acid and chlorogenic acid.
Background technology
Pterocypsela is the annual or perennial herb of composite family, and past attempts is called that Herba Lactucae Indicae belongs to, and is distributed in East Asia and South Asia region.There are tall and big samara chrysanthemum Pterocypsela elata (Hemsl.) Shih, Taiwan samara chrysanthemum P.formosana (Maxim.) Shih, wing burretiodendron esquirolii chrysanthemum P.triangulata (Maxim.) Shih, nerville samara chrysanthemum P.raddeana (Maxim.) Shih, thin beak samara chrysanthemum P.sonchus (L é vl.et Vaniot) Shih, samara chrysanthemum P.indica (L.) C.Shih and split samara chrysanthemum P.laciniata (Houtt) Shih etc. more.Yang Changxu delivers a new variant when studying the Pterocypsela of reservoir area of Three Gorges, and Combination nova one new variant.Novel species is P. lyrata Pterocypsela lyrata C.X.Yang, new variant is oval samara chrysanthemum Pterocypsela indica (L.) Shih var.dentata (Kom.) C.X.Yang, therefore, current Pterocypsela comprises 8 kinds and 1 mutation (Yang Changxu altogether, reservoir area of Three Gorges Pterocypsela and Lactuca new faxa, Agricultural University Of Southwest's journal, 2001,23 (6): 484-485; Yang Changxu, the sort research of reservoir area of Three Gorges Lactuca and Pterocypsela plant, Agricultural University Of Southwest's journal, 2001,23 (5): 425-428).
Samara chrysanthemum reproductivity is very strong, to stressful environmental, there are stronger tolerance and adaptive faculty (Wang Jing, Liu Peng, Wang Shan etc., the physiological responses that Taiwan samara chrysanthemum is coerced different drought, Agriculture of Anhui science, 2008,36 (10): 3978-3979), and by discharging chemical substance in vitro, i.e. allelopathy, suppresses the growth of other plant, can cause the multifarious forfeiture of invasion ground eciophyte.In large stretch of vitellarium of samara chrysanthemum, all need to drop into a large amount of man power and materials every year and carry out rooting out cleaning.
Pterocypsela is wide at national distributed pole, if as edible wild herbs, not only raciness, nutritive value are also higher, also there is many-sided vital role (Yuguang Lin such as antitumor, anti-oxidant, resisting cardiovascular disease, Gert W.Meijer, Mario A.Vermeer et al.Soy protein enhances the cholesterol-lowering effect of plant sterolesters in cholesterol-fed hamsters, Journal of Nutrition, 2004,134 (1): 143-148).Can be used as growing vegetables, in vegetables dull seasons for people provide good merchantable brand (Teng Youde, the Le Zhengbi of nutritious cauline leaf and health care, Yang Changxu, reservoir area of Three Gorges part Pterocypsela plant application is studied, plant genetic resources science, 2001,2 (3): 40-44).
In recent years, the research of active ingredients of plants is become increasingly active, splitting, content of phytosterol in samara chrysanthemum is very abundant more, Hou Caiting etc. adopt Ultra Performance Liquid Chromatography and MS to determine the content splitting plant sterol monomeric compound in samara chrysanthemum more, show to split containing β-sitosterol, Stigmasterol in samara chrysanthemum, they all have obvious reducing blood-fat, anti-inflammatory, antiulcer agent and antitumor action more.
Split in samara chrysanthemum also containing sesquiterpene lactones compounds (11 β more, 13-dihydro lettuce lactone acetic ester), effect (Bi Zhiming that it has clearing heat and detoxicating, removing blood stasis and activating blood flow significantly, regulates the flow of vital energy, Wang Zhengtao, Xu Guojun etc. the chemical composition of Lactuca laciniata and activity research thereof, China Medicine University's journal, 1996,27 (11): 649-651).The volatile oil split in the dry root of samara chrysanthemum has banksia rose fragrance more, containing 35 kinds of compounds in volatile oil, be mainly long-chain fat hydrocarbon and terpenes and containing oxygen derivative (Dong Li thereof, Sun Xiangde, Guo Lanqing etc. split the volatile oil component of samara chrysanthemum more, GUIHAIA, 2004,24 (1): 61-63).
Chinese invention patent " a kind of anti-cerebral ischemia, myocardial ischemia compound of Improving memory function and its preparation method and application " (Yan Fulin etc., CN1935800A) taking high samara chrysanthemum, splitting the Pterocypsela plant roots such as samara chrysanthemum more is raw material, and immersion, distillation, chromatography obtain the compound shown in formula 1.The root biomass of samara chrysanthemum is limited, and the present invention can utilize samara chrysanthemum herb, and scope of selecting material is larger.
(wherein, R is Glc or H; R ' is CH
2oH or CHO)
Formula more than 1 splits the compounds in samara chrysanthemum
Patent of the present invention is by carrying out extraction and isolation to the effective constituent of samara chrysanthemum, and find wherein phenolic acid compound rich content, particularly chicoric acid content is high.
Chicoric acid, has another name called chicoric acid, and its molecular weight is 474.There are four kinds of isomerss: D-chicoric acid, L-chicoric acid, meso chicoric acid and racemize chicoric acid.Wherein, L-chicoric acid is more common in echinacea purpurea, and in the plants such as Root of Chinese Pulsatilla, D-chicoric acid is common in witloof, and meso chicoric acid extracts and obtains from meadow pine.
The molecular formula of chicoric acid is C
22h
18o
12, molecular structure as shown in Equation 2.
Formula 2 chicoric acid molecular structure
Chicoric acid can suppress Unidasa, reduces the impact of radical pair collagen protein, keeps structure and the integrity of reticular tissue and intercellular stroma thereof, strengthens immunologic function, anti-inflammatory action, also have the effect suppressing HIV-1, HIV-1 intergrase.Therefore become a kind of immunopotentiating agent and immunomodulator that receive common concern in the world at present.
Nearest discovery, chicoric acid can be used for treatment dementia disease (Jiang Ruizhi etc., the purposes of chicoric acid in preparation treatment dementia disease medicine, CN101292971A), the cardiovascular disorder such as coronary heart diseases and angina pectoris, cerebral infarction (Ma Zhanzhi etc., chicoric acid and extraction and separation method thereof and purposes, CN102249917A), and (Ma Zhanzhi etc., a kind of chicoric acid and its production and use, CN102391118A) has purposes in anti-cerebral ischemia.
Also effect is had in addition at food and/or beauty industry, Chinese invention patent " chicoric acid and milk-acid bacteria in food supplement for the Pigmented purposes of regulation of skin " (the lucky tal fibre of M etc., CN103025309A) find, chicoric acid and/or derivative and can be hydrolyzed chicoric acid and/or derivative with the composition generating tartrate and/or caffeinic microorganism and/or enzyme for preventing and/or treating the hyperpigmentation of skin and/or skin splash such as senile plaque etc., also can be used as skin-whitening agents.In addition, the extract of chicoric acid to lard and rapeseed oil antioxidant effect obvious, it effectively can delay the peroxidatic reaction of lipid of grease, can be used for (Yuan Yi etc., the purposes of chicoric acid extract in a kind of echinacea purpurea, CN102726550A) in foodstuffs industry
Chinese invention patent " iso chicoric acid and extraction and separation method and the purposes in medicine " thereof (Chen Yinghong etc.; CN101062895A) from Herba Ixeritis Sonchifoliae, separation obtains a kind of iso chicoric acid (two-3; 5-) dihydroxyl cinnamoyl tartrate, it have anti-ageing, strengthen immunity and antineoplastic function.
At present, the method of producing chicoric acid mainly contains chemosynthesis and extract two kinds from plant, to equipment requirements, the higher and toxicity of chemicals makes people produce worry (Nigel B.Perry.J.Agric.Food Chem to the security of product to chemical synthesis process, 2001,49 (4): 1702-1706).And the content of chicoric acid is often lower in natural phant, as it has been generally acknowledged that the higher echinacea purpurea of content, its root content is 0.6%-2.1%, middle content is spent to be 1.2%-1.3%, then content less (Li Shengjun, the technique study of chicoric acid in phase transition extraction process high efficiency separation echinacea purpurea, Hunan Normal University in blade and stem, master thesis, 2012).From existing document, the raw material producing chicoric acid is with echinacea purpurea, witloof (Yuan Yi etc., the purposes of chicoric acid extract in a kind of echinacea purpurea, CN102726550A; Zhang Cunli, a kind of technique utilizing witloof to prepare chicoric acid, 10073388.4) etc.
Echinacea purpurea is the medicinal plant that western countries commonly use, and the standing echinacea purpurea preventing cold of most of family, has saying of " west Root of Indigowoad ".But it is reported that the chicoric acid content in its leaf is not high, if chicoric acid content in the echinacea purpurea leaf that Li Jing etc. reports is 5.60mg/g(Li Jing, introduce a fine variety the qualitative and quantitative analysis of chicoric acid in echinacea purpurea, pharmaceutical analysis magazine, 2011,31 (9): 1804-1807), the present invention finds that in samara chrysanthemum leaf, chicoric acid content is 25.3mg/g, is the former 4.5 times.The chicoric acid amount of echinacea purpurea root is higher compared with leaf (12.1mg/g), but the limits throughput of root (about 0.45kg/m
2) (Wu Qilin, Extraction and Purification Process of Cichoric Acid research in echinacea purpurea, Beijing University of Chemical Technology, master thesis, 2004), be therefore necessary to find the higher plant resources of content.
Split the fresh biomass of samara chrysanthemum very large, dry biomass is 0.545kg/m more
2(Han Xiaoran, Sun Congshan, Zhang Haiyun etc. Laoshan higher plant Investigation on Diversity is studied, the anti-system of medical faunae, 2009,25 (4): 279-280).No matter thus from content or the angle from biomass, samara chrysanthemum has great advantage as the raw material extracting chicoric acid.
The present invention finds in samara chrysanthemum except chicoric acid, also has monocaffeyltartaric acid, 3,5-dicaffeoyl-quinic acid and chlorogenic acid.These compositions have good purposes, if monocaffeyltartaric acid is the phenolic compound of non-flavonoid the abundantest in grape and grape wine, has stronger anti-oxidant activity, have very large application potential.
Summary of the invention
In order to make samara chrysanthemum be used more effectively, the present invention proposes with samara chrysanthemum for raw material extraction and isolation chicoric acid, monocaffeyltartaric acid, the method for 3,5-dicaffeoyl-quinic acid and chlorogenic acid.
The invention discloses with Pterocypsela plant for raw material extraction and isolation chicoric acid simultaneously, monocaffeyltartaric acid, the purposes of 3,5-dicaffeoyl-quinic acid and chlorogenic acid.
Described raw material is the leaf of Pterocypsela plant, stem, flower or herb.
More described Pterocypsela plant splits samara chrysanthemum, Taiwan samara chrysanthemum, tall and big samara chrysanthemum, samara chrysanthemum, thin beak samara chrysanthemum, wing burretiodendron esquirolii chrysanthemum, nerville samara chrysanthemum, oval samara chrysanthemum and P. lyrata.
The invention also discloses a kind of extraction and isolation chicoric acid simultaneously, monocaffeyltartaric acid, the method for 3,5-dicaffeoyl-quinic acid and chlorogenic acid, comprises the following steps:
1) solution extracts or through ultrasonic or microwave radiation exaraction: starting material with water or methyl alcohol or ethanol or acetone equal solvent extract, and filter, concentrated;
2) solvent extraction: the alcohols such as extracting solution Virahol or propyl carbinol or the extraction of the ester such as methyl-formiate or ethyl acetate class equal solvent, obtain chlorogenic acid and 3, the mixture of 5-cynarin, extracting phase is the mixture of chicoric acid and monocaffeyltartaric acid;
3) chlorogenic acid and 3, the separation of 5-cynarin: will containing chlorogenic acid and 3, the mixed solution of 5-cynarin, through ordinary method fractionation by adsorption such as macroporous resins, obtains chlorogenic acid and the 3,5-dicaffeoyl-quinic acid of content more than 90% respectively after refining.
4) being separated of chicoric acid and monocaffeyltartaric acid: by the mixed solution containing chicoric acid and monocaffeyltartaric acid through ordinary method fractionation by adsorption such as macroporous resins, obtain chicoric acid and the monocaffeyltartaric acid of content more than 90% after refining respectively;
Above-mentioned 3) and 4) in, macroporous resin used is nonpolar or polar macroporous resin, is preferably non-polar column, and resin can be one or more in D101, D301, HPD100, HPD300, X-5, XAD-2, but is not limited in above listed kind.
The invention has the beneficial effects as follows: make the samara chrysanthemum of splitting of weeds become production chicoric acid more, monocaffeyltartaric acid, the raw material sources of 3,5-dicaffeoyl-quinic acid and chlorogenic acid, reduce raw materials cost and the production cost of four kinds of products such as chicoric acid simultaneously to the separation of these four kinds of compositions.
Accompanying drawing explanation
The HPLC analysis chart of Fig. 1 samara chrysanthemum extracting solution.
Fig. 2 witloof acidity scale product liquid phase analysis figure.
Embodiment
Further illustrate the present invention below in conjunction with embodiment, citing is for process of the present invention being described but not being only limitted to embodiment.
Witloof acidity scale product HPLC as shown in Figure 2.
Embodiment 1
Get and split samara chrysanthemum herb 1000g adds 90% acetone by solid-to-liquid ratio 1:30 more, extract 2h(extracting solution HPLC analysis at 60 DEG C and see Fig. 1) the concentrated rear n-butanol extraction of extracting solution, obtain respectively containing the extraction liquid of chlorogenic acid and 3,5-dicaffeoyl-quinic acid and containing the raffinate of chicoric acid and monocaffeyltartaric acid;
Extraction liquid D101 macroporous resin, through conventional fractionation by adsorption with after refining, obtains the chlorogenic acid and the 3,5-dicaffeoyl-quinic acid that contain 90% respectively.
Raffinate XAD-2 resin, through conventional fractionation by adsorption with after refining, obtains chicoric acid and the monocaffeyltartaric acid of content 90%.
Embodiment 2
Identical with embodiment 1, change splitting samara chrysanthemum herb the root splitting samara chrysanthemum into more more, be the methyl alcohol that 1:100 adds 60% by solid-to-liquid ratio, 90 DEG C are extracted 1.0h, extract by glycerol after extracting solution is concentrated, extraction liquid D301 macroporous resin, through conventional fractionation by adsorption with after refining, obtains the chlorogenic acid and the 3,5-dicaffeoyl-quinic acid that contain 92% respectively.
Raffinate X-5 resin, through conventional fractionation by adsorption with after refining, obtains chicoric acid and the monocaffeyltartaric acid of content 91%.
Embodiment 3
Identical with embodiment 1, change splitting samara chrysanthemum herb the leaf splitting samara chrysanthemum into more more.Add the ethanol of 70% by solid-to-liquid ratio 1:60, extract 1h at 60 DEG C.Extracting solution concentrates rear isopropyl alcohol extraction, and extraction liquid HPD100 resin, through conventional fractionation by adsorption with after refining, obtains the chlorogenic acid and the 3,5-dicaffeoyl-quinic acid that contain 89% respectively.
Raffinate through the fractionation by adsorption of routine with after refining, obtains chicoric acid and the monocaffeyltartaric acid of content 93% with HPD300 resin.
Embodiment 4
Identical with embodiment 1, will samara chrysanthemum be split more change into the root of samara chrysanthemum.Add water by solid-to-liquid ratio 1:50, extract 2h at 60 DEG C.With methyl-formiate extraction after extracting solution is concentrated, extraction liquid HPD100 resin, through conventional fractionation by adsorption with after refining, obtains the chlorogenic acid and the 3,5-dicaffeoyl-quinic acid that contain 92% respectively.
Raffinate through the fractionation by adsorption of routine with after refining, obtains chicoric acid and the monocaffeyltartaric acid of content 93% with D301 resin.
Embodiment 5
Identical with embodiment 1, will split samara chrysanthemum more and change into the flower of samara chrysanthemum, extraction agent changes ethyl acetate into.
Embodiment 6
Identical with embodiment 1, change Taiwan samara chrysanthemum into by splitting samara chrysanthemum, extraction agent changes formic acid penta fat into more.
Embodiment 7
Identical with embodiment 1, change thin beak samara chrysanthemum into by splitting samara chrysanthemum more.
Embodiment 8
Identical with embodiment 1, change wing burretiodendron esquirolii chrysanthemum into by splitting samara chrysanthemum more.
Embodiment 9
Identical with embodiment 1, change nerville samara chrysanthemum into by splitting samara chrysanthemum more.
Embodiment 10
Identical with embodiment 1, change tall and big samara chrysanthemum into by splitting samara chrysanthemum more.
Embodiment 11
Identical with embodiment 1, change P. lyrata into by splitting samara chrysanthemum more.
Embodiment 12
Identical with embodiment 1, change oval samara chrysanthemum into by splitting samara chrysanthemum more.
Claims (1)
1. a simultaneously extraction and isolation chicoric acid, monocaffeyltartaric acid, the method for 3,5-dicaffeoyl-quinic acid and chlorogenic acid, to is characterized in that with Pterocypsela plant, for raw material, obtaining associated products through the following step:
1) solution is through to extract or through ultrasonic or microwave radiation exaraction: starting material with water or methyl alcohol or ethanol or acetone extraction, filters, concentrated;
2) solvent extraction: extracting solution glycerol or Virahol or propyl carbinol or methyl-formiate or ethyl acetate or pentyl formate extraction, obtain chlorogenic acid and 3, the mixture of 5-cynarin, extracting phase is the mixture of chicoric acid and monocaffeyltartaric acid;
3) being separated of chlorogenic acid and 3,5-dicaffeoyl-quinic acid: be separated containing chlorogenic acid through macroporous resin adsorption with the mixed solution of 3,5-dicaffeoyl-quinic acid, obtain chlorogenic acid and the 3,5-dicaffeoyl-quinic acid of content more than 90% after refining respectively; Described macroporous resin is one or more in D101, D301, HPD100, HPD300, X-5, XAD-2;
4) being separated of chicoric acid and monocaffeyltartaric acid: be separated containing chicoric acid through macroporous resin adsorption with the mixed solution of monocaffeyltartaric acid, obtain chicoric acid and the monocaffeyltartaric acid of content more than 90% after refining respectively; Described macroporous resin is one or more in D101, D301, HPD100, HPD300, X-5, XAD-2.
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| CN101367728A (en) * | 2008-10-09 | 2009-02-18 | 湖南师范大学 | Method for purifying chicoric acid and monocaffeyltartaric acid from echinacea purpurea extract |
| CN102391120A (en) * | 2011-12-07 | 2012-03-28 | 南京师范大学 | Method for extracting dicaffeoylquinic acid and chlorogenic acid simultaneously by using solidago canadensis as raw material |
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| CN101367728A (en) * | 2008-10-09 | 2009-02-18 | 湖南师范大学 | Method for purifying chicoric acid and monocaffeyltartaric acid from echinacea purpurea extract |
| CN102391120A (en) * | 2011-12-07 | 2012-03-28 | 南京师范大学 | Method for extracting dicaffeoylquinic acid and chlorogenic acid simultaneously by using solidago canadensis as raw material |
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