CN102329324A - Process method for simultaneously preparing picropodophyllone and picropodophyllin - Google Patents

Process method for simultaneously preparing picropodophyllone and picropodophyllin Download PDF

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Publication number
CN102329324A
CN102329324A CN201110304607A CN201110304607A CN102329324A CN 102329324 A CN102329324 A CN 102329324A CN 201110304607 A CN201110304607 A CN 201110304607A CN 201110304607 A CN201110304607 A CN 201110304607A CN 102329324 A CN102329324 A CN 102329324A
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China
Prior art keywords
picropodophyllotoxin
picrotone
emodi var
var chinense
podophyllum emodi
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CN201110304607A
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Chinese (zh)
Inventor
刘东锋
吴艳波
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Nanjing Zelang Medical Technology Co Ltd
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Nanjing Zelang Medical Technology Co Ltd
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Priority to CN201110304607A priority Critical patent/CN102329324A/en
Publication of CN102329324A publication Critical patent/CN102329324A/en
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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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  • Medicines Containing Plant Substances (AREA)
  • Heterocyclic Carbon Compounds Containing A Hetero Ring Having Oxygen Or Sulfur (AREA)

Abstract

The invention discloses a process method for simultaneously preparing picropodophyllone and picropodophyllin. The method comprises the following steps: taking raw material powder, firstly performing supercritical CO2 extraction to get an extract, and then performing further purification via high-speed counter-current chromatography so as to get pure products of the picropodophyllone and the picropodophyllin. The high-speed counter-current chromatography is adopted in the preparation process, thereby overcoming the shortcomings of sample adsorption, loss and the like; and furthermore, the high-speed counter-current chromatography has the advantage of large preparation quantity, easiness in industrialization and the like.

Description

A kind of process method for preparing Podophyllum emodi var chinense picrotone and picropodophyllotoxin simultaneously
Technical field
The present invention relates to from natural phant, prepare the method for activeconstituents, specifically, relate to a kind of process method for preparing Podophyllum emodi var chinense picrotone and picropodophyllotoxin simultaneously.
Background technology
Podophyllum emodi var chinense picrotone (picropodophyllone, C 22H 20O 8), picropodophyllotoxin (podophyllotoxin, C 22H 22O 8) belong to lignan class (lignans), mainly be present in Berberidaceae perennial herb monoid Podophyllum emodi var chinense subfamily Dysosma, Rhizoma et Radix Diphylleiae genus, Chinese podophyllum root genus, unmrellaleaf genus and the ZUYECAO platymiscium.These plants the leaf of giving birth to owing to all have peltate, have most scattered microtubule fasolculuss in the stem, and flower is not had a nectary, however berry contain some common traits such as picropodophyllotoxin and be counted as one from relatively independent monoid, be called Podophyllum emodi var chinense class plant traditionally.Podophyllum emodi var chinense class plant is one type and contains notable biological activity, has the medicinal plant of long applicating history.The record of Podophyllum emodi var chinense is just arranged in the Shennong's Herbal of China Han dynasty.That such plant has is antitumor, expelling phlegm for arresting cough, anti-inflammatory and effect such as antiviral, contains the lignan component that has antitumour activity in a large number in its root, stem and the leaf.Wherein, Podophyllum emodi var chinense picrotone and picropodophyllotoxin are main active ingredient.
Podophyllum emodi var chinense picrotone: colourless needle, molecular formula C 22H 20O 8, molecular weight 412.39; Pharmacological action mainly contains: 1. antitumor action, and to the IC of P388, A-549, HT-29 50All be 5 mcg/ml, the IC of contrast medicine Zorubicin 50(mcg/ml) is respectively 0.017,0.053 and 0.11; 2. antivirus action is to the IC of HSV/CV-1 and VSV/BHK 50(mcg/ml) is respectively 20 and 10; 3. antifungic action when 200 mcg/ml, has strong inhibitory activity to acrothesium floccosum, curved spore, the black spore of rice, oyster cap fungus etc.
Picropodophyllotoxin: colourless fine needle is brilliant, molecular formula C 22H 22O 8, molecular weight 414.41; Pharmacological action mainly contains antitumor action, to the IC of P388, A-549, HT-29 50Mcg/ml all＜2.5, the IC of contrast medicine Zorubicin 50(mcg/ml) is respectively 0.017,0.053 and 0.11, to the IC of HSV/CV-1 and VSV/BHK 50(mcg/ml) difference＜20 and 10.
Prior art adopts the supersound extraction picropodophyllotoxin, and adopts the method for high-speed countercurrent chromatography purifying Podophyllum emodi var chinense picrotone and picropodophyllotoxin not see bibliographical information as yet.
Summary of the invention
The object of the present invention is to provide a kind of process method for preparing Podophyllum emodi var chinense picrotone and picropodophyllotoxin simultaneously, to obtain highly purified Podophyllum emodi var chinense picrotone and picropodophyllotoxin simultaneously.
For realizing above-mentioned purpose, technical scheme of the present invention is following:
1) raw medicinal material is pulverized, placed extraction kettle, carry out supercritical CO 2Extraction is resolved, and collects extract;
2) get normal hexane-ETHYLE ACETATE-acetonitrile-water (uniform mixing of 3 ~ 5:3 ~ 6:4 ~ 8:5), fully saturated after, left standstill 10-12 hour; Getting is stationary phase mutually, is moving phase mutually down, and extract is dissolved with moving phase; Stationary phase is pumped in the spiral tube of adverse current chromatogram; The adjusting rotating speed is 800-1000rpm, with the flow velocity of 1.5-3ml/min moving phase is pumped into, and treats the stable back of loom sample introduction; Collect Podophyllum emodi var chinense picrotone and picropodophyllotoxin flow point respectively, concentrated, cryodrying promptly gets Podophyllum emodi var chinense picrotone and picropodophyllotoxin.
Said raw medicinal material derives from plant rhizome or leaves such as Berberidaceae Shaanxi Rhizoma et Radix Diphylleiae, Diphylleia sinensis, Yunan Many-flowered May-apple, Guizhou Sixangular Dysosma Rhizome and Root, Guangxi Sixangular Dysosma Rhizome and Root, Chinese podophyllum root.
Said supercritical extraction temperature is 35-50 ℃, and extracting pressure is 22-40MPa, and resolution temperature is 18-40 ℃, and parsing pressure is 8-15MPa, CO 2Flow is 18-30L/h.
Advantage of the present invention is:
(1) adopts the supercritical extraction technology, efficient no solvent residue, environmentally safe;
(2) adopt high speed adverse current chromatogram preparation technology, overcome shortcomings such as the sample absorption that solid phase carrier brings, loss, and the HSCCC method have preparation amount big, be easy to advantage such as industrial popularization.
Embodiment
Further the present invention is explained below in conjunction with embodiment:
Embodiment 1:
Berberidaceae plant Shaanxi Rhizoma et Radix Diphylleiae rhizome leaf is pulverized, got 1kg and place extraction kettle, feed supercritical CO 2Fluid carries out supercritical CO 2Extraction, CO 2Flow is 18L/h, and the supercritical extraction temperature is 50 ℃, and extracting pressure is 40MPa, resolves, and resolution temperature is 18 ℃, and parsing pressure is 15MPa, collects the Berberidaceae plant milk extract; Water and acetonitrile 4:5 by volume mix, and the preparation mixed liquor A with normal hexane and ETHYLE ACETATE 3:3 by volume, is prepared mixed liquid B; With mixed liquor A and mixed liquid B uniform mixing, fully saturated after, left standstill 10 hours, take off and be stationary phase mutually; On be moving phase mutually, the Berberidaceae plant milk extract is dissolved with moving phase, stationary phase is pumped in the spiral tube of adverse current chromatogram, the adjusting rotating speed is 1000rpm; Flow velocity with 3ml/min pumps into moving phase, treats the stable back of loom sample introduction, collects Podophyllum emodi var chinense picrotone and picropodophyllotoxin flow point respectively; Podophyllum emodi var chinense picrotone flow point is concentrated, cryodrying obtains Podophyllum emodi var chinense picrotone 7mg, detects through HPLC, and purity is 98.2%; The picropodophyllotoxin flow point is concentrated, cryodrying obtains picropodophyllotoxin 12mg, detects through HPLC, and purity is 98.1%.
Embodiment 2:
Berberidaceae plant Diphylleia sinensis rhizome leaf is pulverized, got 1kg and place extraction kettle, feed supercritical CO 2Fluid carries out supercritical CO 2Extraction, CO 2Flow is 30L/h, and the supercritical extraction temperature is 35 ℃, and extracting pressure is 22MPa, resolves, and resolution temperature is 40 ℃, and parsing pressure is 8MPa, collects the Berberidaceae plant milk extract.Water and acetonitrile 8:5 by volume mix, and the preparation mixed liquor A with normal hexane and ETHYLE ACETATE 5:3 by volume, is prepared mixed liquid B; With mixed liquor A and mixed liquid B uniform mixing, fully saturated after, left standstill 10 hours, take off and be stationary phase mutually; On be moving phase mutually, the Berberidaceae plant milk extract is dissolved with moving phase, stationary phase is pumped in the spiral tube of adverse current chromatogram, the adjusting rotating speed is 800rpm; Flow velocity with 1.5ml/min pumps into moving phase, treats the stable back of loom sample introduction, collects Podophyllum emodi var chinense picrotone and picropodophyllotoxin flow point respectively; Podophyllum emodi var chinense picrotone flow point is concentrated, cryodrying obtains Podophyllum emodi var chinense picrotone 5mg, detects through HPLC, and purity is 98.5%; The picropodophyllotoxin flow point is concentrated, cryodrying obtains picropodophyllotoxin 8mg, detects through HPLC, and purity is 98.3%.
Embodiment 3:
Berberidaceae plant Yunan Many-flowered May-apple rhizome leaf is pulverized, got 1kg and place extraction kettle, feed supercritical CO 2Fluid carries out supercritical CO 2Extraction, CO 2Flow is 25L/h, and the supercritical extraction temperature is 40 ℃, and extracting pressure is 28MPa, resolves, and resolution temperature is 25 ℃, and parsing pressure is 12MPa, collects the Berberidaceae plant milk extract.Water and acetonitrile 6:5 by volume mix, and the preparation mixed liquor A with normal hexane and ETHYLE ACETATE 4:5 by volume, is prepared mixed liquid B; With mixed liquor A and mixed liquid B uniform mixing, fully saturated after, left standstill 10 hours, take off and be stationary phase mutually; On be moving phase mutually, the Berberidaceae plant milk extract is dissolved with moving phase, stationary phase is pumped in the spiral tube of adverse current chromatogram, the adjusting rotating speed is 1000rpm; Flow velocity with 2.5ml/min pumps into moving phase, treats the stable back of loom sample introduction, collects Podophyllum emodi var chinense picrotone and picropodophyllotoxin flow point respectively; Podophyllum emodi var chinense picrotone flow point is concentrated, cryodrying obtains Podophyllum emodi var chinense picrotone 4mg, detects through HPLC, and purity is 98.1%; The picropodophyllotoxin flow point is concentrated, cryodrying obtains picropodophyllotoxin 11mg, detects through HPLC, and purity is 98.5%.
Embodiment 4:
Berberidaceae plant Guangxi Sixangular Dysosma Rhizome and Root rhizome leaf is pulverized, got 1kg and place extraction kettle, feed supercritical CO 2Fluid carries out supercritical CO 2Extraction, CO 2Flow is 22L/h, and the supercritical extraction temperature is 38 ℃, and extracting pressure is 33MPa, resolves, and resolution temperature is 25 ℃, and parsing pressure is 13MPa, collects the Berberidaceae plant milk extract.Water and acetonitrile 7:5 by volume mix, and the preparation mixed liquor A with normal hexane and ETHYLE ACETATE 4:3 by volume, is prepared mixed liquid B; With mixed liquor A and mixed liquid B uniform mixing, fully saturated after, left standstill 10 hours, take off and be stationary phase mutually; On be moving phase mutually, the Berberidaceae plant milk extract is dissolved with moving phase, stationary phase is pumped in the spiral tube of adverse current chromatogram, the adjusting rotating speed is 950rpm; Flow velocity with 2.8ml/min pumps into moving phase, treats the stable back of loom sample introduction, collects Podophyllum emodi var chinense picrotone and picropodophyllotoxin flow point respectively; Podophyllum emodi var chinense picrotone flow point is concentrated, cryodrying obtains Podophyllum emodi var chinense picrotone 5mg, detects through HPLC, and purity is 98.5%; The picropodophyllotoxin flow point is concentrated, cryodrying obtains picropodophyllotoxin 10mg, detects through HPLC, and purity is 98.6%.

Claims (3)

1. process method for preparing Podophyllum emodi var chinense picrotone and picropodophyllotoxin simultaneously is characterized in that:
1) raw medicinal material is pulverized, placed extraction kettle, carry out supercritical CO 2Extraction is resolved, and collects extract;
2) get normal hexane-ETHYLE ACETATE-acetonitrile-water (uniform mixing of 3 ~ 5:3 ~ 6:4 ~ 8:5), fully saturated after, left standstill 10-12 hour; Getting is stationary phase mutually, is moving phase mutually down, and extract is dissolved with moving phase; Stationary phase is pumped in the spiral tube of adverse current chromatogram; The adjusting rotating speed is 800-1000rpm, with the flow velocity of 1.5-3ml/min moving phase is pumped into, and treats the stable back of loom sample introduction; Collect Podophyllum emodi var chinense picrotone and picropodophyllotoxin flow point respectively, concentrated, cryodrying promptly gets Podophyllum emodi var chinense picrotone and picropodophyllotoxin.
2. the process method of preparation Podophyllum emodi var chinense picrotone according to claim 1 and picropodophyllotoxin is characterized in that: said raw medicinal material derives from plant rhizome or leaves such as Berberidaceae Shaanxi Rhizoma et Radix Diphylleiae, Diphylleia sinensis, Yunan Many-flowered May-apple, Guizhou Sixangular Dysosma Rhizome and Root, Guangxi Sixangular Dysosma Rhizome and Root, Chinese podophyllum root.
3. the process method of preparation Podophyllum emodi var chinense picrotone according to claim 1 and picropodophyllotoxin is characterized in that: said supercritical extraction temperature is 35-50 ℃, and extracting pressure is 22-40MPa, and resolution temperature is 18-40 ℃, and parsing pressure is 8-15MPa, CO 2Flow is 18-30L/h.
CN201110304607A 2011-10-10 2011-10-10 Process method for simultaneously preparing picropodophyllone and picropodophyllin Pending CN102329324A (en)

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Application publication date: 20120125