CN102030795A - Cucurbitane momordicoside and preparation method thereof - Google Patents
Cucurbitane momordicoside and preparation method thereof Download PDFInfo
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- CN102030795A CN102030795A CN 201010565395 CN201010565395A CN102030795A CN 102030795 A CN102030795 A CN 102030795A CN 201010565395 CN201010565395 CN 201010565395 CN 201010565395 A CN201010565395 A CN 201010565395A CN 102030795 A CN102030795 A CN 102030795A
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Abstract
The invention provides cucurbitane momordicoside and a preparation method thereof, and relates to momordicoside and a preparation method thereof. The preparation method comprises the following steps: 1. preparing crudely extracted total momordicosides; 2. preparing purified total momordicosides; 3. preparing refined total momordicosides; and 4. preparing the cucurbitane momordicoside. The invention provides the structure of a novel cucurbitane momordicoside and the preparation method thereof. The structure of the obtained new compound is as follows: 7beta,25-dihydroxyl-cucurbitane-5,23-diene-19-aldehyde-3-O-beta-D-glucopyranoside, and the structure is confirmed through infrared spectrum, liquid chromatogram-mass spectrum (LC-MS), hydrogen spectrum and carbon spectrum detections.
Description
Technical field
The present invention relates to a kind of balsam pear saponin(e and preparation method thereof.
Background technology
That momordica saponins has is hypoglycemic, anti-oxidant, improve immunizing power, reducing cholesterol, anti AIDS virus and physiological function such as antitumor
[1]Structure about the balsam pear saponin(e identifies that Chinese scholars has been done a large amount of work, Zhu Zhaojing, Zhong Chichang, Luo Zeyuan etc.
[2](1990) isolate compound 24 β-ethyl-5a-courage steroid-7, trans 22E, 25 (27)-triolefins-3 beta-hydroxies-3-O-β-D-glucopyranoside; Okable, H.et al.
[3]Get 2 kinds of pentahydroxy-cucurbitane triterpene glucosides, i.e. balsam pear saponin A, B (momordicosides Aand B).Yumi Miyahara, et al.
[4](1981) obtain three new triterpene glucosides, called after balsam pear saponin(e C, D and E (momordicosides C, D and E), and continue in nineteen eighty-two
[5]Separate the balsam pear saponin(e G, the F that obtain not having bitter taste
1, F
2, and I (momordicosides G, F
1, F
2And I) and balsam pear saponin(e K and L (momordicosides K and L) that bitter taste is arranged.Zhu Zhaojing [2] isolates new compound momorcharsides A and B from the balsam pear seed; And Yasuda M.et al[6] separate and to obtain momordicine I, water layer with butanols extract momordicine II and III.Toshiyuki M.et al.
[7](2001) extraction separation new cucurbitane type triterpenoid saponin be Goyaglycosides a, b, c, d, e, f, g; With new oleanolic acid type triterpenoid saponin be Goyasaponins I, II and III.Yu Lijuan, Chen Quanbin, adopted auspicious brightness etc.
[8](2003) Momordica grosvenori mogroside V standard substance.Crux, Pan Hui, Zhao Yuqing
[9]From balsam pear, separate and identified 2 pairs of isomer.Tentatively be defined as 19R-5 β, 19 epoxy cucurbitanes-6,23,25-triolefin-3 β, 19-glycol (Ia) and 19S-5 β, 19 epoxy cucurbitanes-6,23,25-triolefin-3 β, 19-glycol (Ib); Another chemical structure to isomer is defined as 5 β, 19 epoxy cucurbitanes-6,23,25-triolefin-3-O-glucopyranoside (IIa) and 5 β, 19 epoxy cucurbitanes-6,23,25-triolefin-3-O-A Luo pyranoside (IIb).The foreign scholar has also found a lot of triterpenes cucurbitane saponin(es, for example, and balsam pear saponin(e Q, R, S, T etc.
Summary of the invention
The objective of the invention is in order to prepare a kind of cucurbitane type balsam pear saponin(e and preparation method thereof.
Cucurbitane type balsam pear saponin(e of the present invention is 7 β, 25-dihydroxyl-cucurbitane-5, and 23-diene-19-aldehyde-3-O-β-D-glucopyranoside, its structural formula is as follows:
The preparation method of described cucurbitane type balsam pear saponin(e is as follows: one, balsam pear section, drying, pulverizing are obtained Fructus Momordicae charantiae powder after cross 40 mesh sieves behind the petroleum ether degreasing, to adopt volumetric concentration then be 70% ethanol at 50 ℃, ultrasonic power is with Fructus Momordicae charantiae powder supersound extraction 40～50min under the condition of 108W, Fructus Momordicae charantiae powder and volumetric concentration are that 70% alcoholic acid mass ratio is 1: 14, filter, with filtrate concentrate, behind the n-butanol extraction, drying, the balsam pear total saponins of slightly being carried; Two, it is in 8 the water that the balsam pear total saponins that will slightly carry is dissolved in the pH value, adopt AB-8 type macroporous resin adsorption 40min～60min then, be that 20% ethanol, volumetric concentration are 70% ethanolic soln wash-out with distilled water, volumetric concentration respectively again, collected volume concentration is 70% ethanol eluate, concentrate, drying obtains the balsam pear total saponins of purifying; Three, solid phase extraction column is activated with 10mL methyl alcohol, 10mL redistilled water, balsam pear total saponins with purifying is transferred in the solid phase extraction column then, with volumetric concentration respectively 10%, 20% and 40% ethanol drip washing, be 65% ethanol elution again with volumetric concentration, collected volume concentration is 65% ethanol eluate, concentrate, drying obtains purified balsam pear total saponins; Four, with purified balsam pear total saponins by half preparative high performance liquid chromatography instrument, and to collect retention time be the cut of 6.854min, cut concentrated again, freeze-drying obtains cucurbitane type balsam pear saponin(e.
The invention provides a kind of structure and preparation method of new cucurbitane type balsam pear saponin(e.The gained All new compounds is 7 β, 25-dihydroxyl-cucurbitane-5,23-diene-19-aldehyde-3-O-β-D-glucopyranoside.The preparation method comprises the ultrasonic wave solvent-extraction process, macroreticular resin absorbing method, and the Solid-Phase Extraction method for refining separates with half preparative high-performance liquid chromatographic.The purity height of this preparation method's gained material.This invention gained new compound is the further perfect monomeric species of balsam pear saponin(e.The preparation monomer methods provides beneficial reference for the commercialization of balsam pear saponin(e standard substance, and then fills up the blank that domestic and international no balsam pear saponin(e standard substance are sold.
The present invention finds first and has prepared a kind of new cucurbitane type balsam pear saponin(e 7 β, 25-dihydroxyl-cucurbitane-5, and 23-diene-19-aldehyde-3-O-β-D-glucopyranoside, its structure detects and confirms through infrared spectra, liquid matter, hydrogen spectrum, carbon spectrum.
Description of drawings
Fig. 1 is the high-efficient liquid phase chromatogram of the cucurbitane type balsam pear saponin(e of embodiment seven preparations; Fig. 2 is the infrared colour spectrogram of the cucurbitane type balsam pear saponin(e of embodiment seven preparations; Fig. 3 is the mass spectrum of the cucurbitane type balsam pear saponin(e of embodiment seven preparations; Fig. 4 be embodiment seven preparation cucurbitane type balsam pear saponin(e the hydrogen spectrogram; Fig. 5 is the carbon spectrogram of the cucurbitane type balsam pear saponin(e of embodiment seven preparations.
Embodiment
Technical solution of the present invention is not limited to following cited embodiment, also comprises the arbitrary combination between each embodiment.
Embodiment one: cucurbitane type balsam pear saponin(e is 7 β in the present embodiment, 25-dihydroxyl-cucurbitane-5, and 23-diene-19-aldehyde-3-O-β-D-glucopyranoside, its structural formula is as follows:
Cucurbitane type balsam pear saponin(e structure in the present embodiment detects and turns out to be 7 β, 25-dihydroxyl-cucurbitane-5,23-diene-19-aldehyde-3-O-β-D-glucopyranoside through infrared spectra, liquid matter, hydrogen spectrum, carbon spectrum.
Embodiment two: the preparation method of cucurbitane type balsam pear saponin(e is as follows in the present embodiment: one, balsam pear section, drying, pulverizing are obtained Fructus Momordicae charantiae powder after cross 40 mesh sieves behind the petroleum ether degreasing, to adopt volumetric concentration then be 70% ethanol at 50 ℃, ultrasonic power is with Fructus Momordicae charantiae powder supersound extraction 40～50min under the condition of 108W, Fructus Momordicae charantiae powder and volumetric concentration are that 70% alcoholic acid mass ratio is 1: 14, filter, with filtrate concentrate, behind the n-butanol extraction, drying, the balsam pear total saponins of slightly being carried; Two, it is in 8 the water that the balsam pear total saponins that will slightly carry is dissolved in the pH value, adopt AB-8 type macroporous resin adsorption 40min～60min then, be that 20% ethanol, volumetric concentration are 70% ethanolic soln wash-out with distilled water, volumetric concentration respectively again, collected volume concentration is 70% ethanol eluate, concentrate, drying obtains the balsam pear total saponins of purifying; Three, solid phase extraction column is activated with 10mL methyl alcohol, 10mL redistilled water, balsam pear total saponins with purifying is transferred in the solid phase extraction column then, with volumetric concentration respectively 10%, 20% and 40% ethanol drip washing, be 65% ethanol elution again with volumetric concentration, collected volume concentration is 65% ethanol eluate, concentrate, drying obtains purified balsam pear total saponins; Four, with purified balsam pear total saponins by half preparative high performance liquid chromatography instrument, and to collect retention time be the cut of 6.854min, cut concentrated again, freeze-drying obtains cucurbitane type balsam pear saponin(e.
Cucurbitane type balsam pear saponin(e structure in the present embodiment detects and turns out to be 7 β, 25-dihydroxyl-cucurbitane-5,23-diene-19-aldehyde-3-O-β-D-glucopyranoside through infrared spectra, liquid matter, hydrogen spectrum, carbon spectrum.
Embodiment three: what present embodiment and embodiment two were different is that the ultrasonic time described in the step 1 is 45min.Other is identical with embodiment two.
Embodiment four: what present embodiment and embodiment two were different is with AB-8 type macroporous resin adsorption 50min in the step 2.Other is identical with embodiment two.
Embodiment five: the preparation method of cucurbitane type balsam pear saponin(e is as follows in the present embodiment: one, balsam pear section, drying, pulverizing are obtained Fructus Momordicae charantiae powder after cross 40 mesh sieves behind the petroleum ether degreasing, to adopt volumetric concentration then be 70% ethanol at 50 ℃, ultrasonic power is with Fructus Momordicae charantiae powder supersound extraction 40min under the condition of 108W, Fructus Momordicae charantiae powder and volumetric concentration are that 70% alcoholic acid mass ratio is 1: 14, filter, with filtrate concentrate, behind the n-butanol extraction, drying, the balsam pear total saponins of slightly being carried; Two, it is in 8 the water that the balsam pear total saponins that will slightly carry is dissolved in the pH value, adopt AB-8 type macroporous resin adsorption 40min then, be that 20% ethanol, volumetric concentration are 70% ethanolic soln wash-out with distilled water, volumetric concentration respectively again, collected volume concentration is 70% ethanol eluate, concentrate, drying obtains the balsam pear total saponins of purifying; Three, solid phase extraction column is activated with 10mL methyl alcohol, 10mL redistilled water, balsam pear total saponins with purifying is transferred in the solid phase extraction column then, with volumetric concentration respectively 10%, 20% and 40% ethanol drip washing, be 65% ethanol elution again with volumetric concentration, collected volume concentration is 65% ethanol eluate, concentrate, drying obtains purified balsam pear total saponins; Four, with purified balsam pear total saponins by half preparative high performance liquid chromatography instrument, and to collect retention time be the cut of 6.854min, cut concentrated again, freeze-drying obtains cucurbitane type balsam pear saponin(e.
Embodiment six: the preparation method of cucurbitane type balsam pear saponin(e is as follows in the present embodiment: one, balsam pear section, drying, pulverizing are obtained Fructus Momordicae charantiae powder after cross 40 mesh sieves behind the petroleum ether degreasing, to adopt volumetric concentration then be 70% ethanol at 50 ℃, ultrasonic power is with Fructus Momordicae charantiae powder supersound extraction 50min under the condition of 108W, Fructus Momordicae charantiae powder and volumetric concentration are that 70% alcoholic acid mass ratio is 1: 14, filter, with filtrate concentrate, behind the n-butanol extraction, drying, the balsam pear total saponins of slightly being carried; Two, it is in 8 the water that the balsam pear total saponins that will slightly carry is dissolved in the pH value, adopt AB-8 type macroporous resin adsorption 60min then, be that 20% ethanol, volumetric concentration are 70% ethanolic soln wash-out with distilled water, volumetric concentration respectively again, collected volume concentration is 70% ethanol eluate, concentrate, drying obtains the balsam pear total saponins of purifying; Three, solid phase extraction column is activated with 10mL methyl alcohol, 10mL redistilled water, balsam pear total saponins with purifying is transferred in the solid phase extraction column then, with volumetric concentration respectively 10%, 20% and 40% ethanol drip washing, be 65% ethanol elution again with volumetric concentration, collected volume concentration is 65% ethanol eluate, concentrate, drying obtains purified balsam pear total saponins; Four, with purified balsam pear total saponins by half preparative high performance liquid chromatography instrument, and to collect retention time be the cut of 6.854min, cut concentrated again, freeze-drying obtains cucurbitane type balsam pear saponin(e.
Embodiment seven: the preparation method of cucurbitane type balsam pear saponin(e is as follows in the present embodiment: one, fresh balsam pear is cut into slices the back 40 ℃ of dryings, pulverize, again with 30g through petroleum ether degreasing, the Fructus Momordicae charantiae powder that 40 orders sieve is put in the 500mL Erlenmeyer flask, be under 1: 14 the condition in solid-to-liquid ratio, adopting volumetric concentration is that 70% ethanol is at 50 ℃, ultrasonic power is with Fructus Momordicae charantiae powder supersound extraction 50min under the condition of 108W, filter then, filtrate is concentrated into ethanol all reclaims, then with concentrated solution and water-saturated n-butanol with the extraction of spending the night of 1: 1 volume ratio, the volume ratio of water and propyl carbinol is 1: 1 in the water-saturated n-butanol, reclaim n-butanol layer, dry, the balsam pear total saponins of promptly slightly being carried, total saponin content is about 26.48% in the balsam pear total saponins of slightly carrying; Two, with the AB-8 type macroporous resin internal diameter of packing into is 2cm, length is the resin column of 60cm, taking by weighing balsam pear total saponins that 2g slightly carries, to be dissolved in 500mL pH value be to pour in the resin column then in 8 the water, applied sample amount is 8 times of resin bed volumes, absorption 50～60min, use the distilled water wash-out then, with volumetric concentration is that 20% ethanol elution discards elutriant, be 70% ethanolic soln wash-out again with volumetric concentration, collected volume concentration is 70% ethanol eluate, concentrates drying, obtain the balsam pear total saponins of purifying, the content of total saponins is about 51.51% in the balsam pear total saponins of purifying; Three, pass through solid phase extraction column with 10mL methyl alcohol, pass through solid phase extraction column with the 10mL redistilled water again, solid phase extraction column is activated, the balsam pear total saponins that takes by weighing the 100mg purifying is dissolved in the 10mL redistilled water, regulate pH=8, fully 0.45 μ m filter membrane is crossed in the dissolving back, flow velocity with 1mL/min passes through solid phase extraction column, with the 15mL volumetric concentration 10% ethanol drip washing, the 15mL volumetric concentration is 20% ethanol drip washing, be 40% ethanol drip washing again with the 10mL volumetric concentration, draining, is 65% ethanol elution then with the 7mL volumetric concentration, and collected volume concentration is 65% ethanol eluate, concentrate, drying obtains purified balsam pear total saponins, and the content of balsam pear total saponins is about 82.13% in the purified balsam pear total saponins; Four, purified balsam pear total saponins is passed through half preparative high performance liquid chromatography instrument, and the collection retention time is the cut of 6.854min, again the cut rotation is concentrated, behind the lyophilization, obtain cucurbitane type balsam pear saponin(e (7 β, 25-dihydroxyl-cucurbitane-5, the monomer of 23-diene-19-aldehyde-3-O-β-D-glucopyranoside).
In the present embodiment step 4 with purified balsam pear total saponins solution as sample liquid, each 100 μ L, detected high-efficient liquid phase chromatogram, preparation condition are detector: UV detector, λ=205nm; Preparative chromatography post: ZORBAXEclipseXDB-C18 (9.4 * 250mm, 5-Micron); Column temperature: 30 ℃; Moving phase: acetonitrile: water=55: 45 (volume ratio); Flow velocity: 4.0mL/min; Sample size: 100 μ L.
As shown in Figure 1, cucurbitane type balsam pear saponin(e 7 β of present embodiment preparation, 25-dihydroxyl-cucurbitane-5,23-diene-19-aldehyde-3-O-β-D-glucopyranoside retention time under preparation condition is 6.854min, and prepared balsam pear saponin(e purity height.
As can be seen from Figure 2,3415.97 (O-H is flexible), 2928.38 (C-H is flexible), 1714.69 (C=O is flexible), 1629.54 (C=C is flexible), 1463.05 (CH
3Or CH
2Flexural vibration), 1379.60 (C-H bendings), 1252.50 (C-O-C asymmetric stretches), 1042.11 (C-O stretching vibrations).
As can be seen from Figure 3, ESI-MS obtains quasi-molecular ion peak and is respectively: m/z657[M+Na]
+, m/z673[M+K]
+, pointing out its molecular weight is 634; M/z419[M+H-162-3H
2O]
+, in the compound of prompting present embodiment preparation glucosyl group being arranged, the molecular formula of determining this component is C
36H
58O
9, degree of unsaturation is 8.
From Fig. 4
1H NMR (300MHz, DMSO-d
6) show: show the proton signal that sugar encircles, four methyl signals (δ 0.80,0.83,0.87,0.91) on quaternary carbon at δ 4-5.At δ H
5-6Signal is arranged, illustrate to exist H to link to each other, and the area ratio is 1: 2, illustrate to have 3 or a multiple H that links to each other with two keys of 3, because the degree of unsaturation of compound is 8, so should be 2 pairs of keys with two keys.δ H
4-5Proton signal on the sugar ring is arranged.
From Fig. 5
13C NMR (300MHz, DMSO-d
6) show: between δ 120-150ppm, exist 4 olefinic carbon signals and belong to C-6, C-23, C-5, C-24.Two hydroxyl carbon signals (δ 74.7,72.9) belong to C-25, C-7.Four quaternary carbon signals (δ 49.1,47.2,45.0,40.8) belong to C-14 respectively, C-13, C-9, C-4.7 methyl signals (δ 29.15,25.2,22.9,20.8,19.0,18.3,14.8) belong to C-29, C-28, C-27, C-26, C-21, C-18, C-30 respectively.On the IR spectrogram, there is C=O, because the compound molecule formula is C
36H
58O
9, determine that therefore there is aldehyde radical in this compound.
13Low has δ 103.8 signals among the CNMR, is indicated as β-D configuration sugar.C
3(δ 83.6) show that to a low mobile 8.8ppm it is for becoming the glycosides position.
13(δ 71.7,71.6,69.0,64.5,63.5) belong to C respectively among the CNMR
5', C
3', C
2', C
4', C
6', because C
5' and C
3' chemical displacement value all less than 80, institute thinks pyranose form.
Claims (4)
1. cucurbitane type balsam pear saponin(e is characterized in that cucurbitane type balsam pear saponin(e is 7 β, 25-dihydroxyl-cucurbitane-5, and 23-diene-19-aldehyde-3-O-β-D-glucopyranoside, its structural formula is as follows:
2. the preparation method of the described cucurbitane type of claim 1 balsam pear saponin(e, the preparation method who it is characterized in that described cucurbitane type balsam pear saponin(e is as follows: one, balsam pear section, drying, pulverizing are obtained Fructus Momordicae charantiae powder after cross 40 mesh sieves behind the petroleum ether degreasing, to adopt volumetric concentration then be 70% ethanol at 50 ℃, ultrasonic power is with Fructus Momordicae charantiae powder supersound extraction 40～50min under the condition of 108W, Fructus Momordicae charantiae powder and volumetric concentration are that 70% alcoholic acid mass ratio is 1: 14, filter, with filtrate concentrate, behind the n-butanol extraction, drying, the balsam pear total saponins of slightly being carried; Two, it is in 8 the water that the balsam pear total saponins that will slightly carry is dissolved in the pH value, adopt AB-8 type macroporous resin adsorption 40min～60min then, be that 20% ethanol, volumetric concentration are 70% ethanolic soln wash-out with distilled water, volumetric concentration respectively again, collected volume concentration is 70% ethanol eluate, concentrate, drying obtains the balsam pear total saponins of purifying; Three, solid phase extraction column is activated with 10mL methyl alcohol, 10mL redistilled water, balsam pear total saponins with purifying is transferred in the solid phase extraction column then, with volumetric concentration respectively 10%, 20% and 40% ethanol drip washing, be 65% ethanol elution again with volumetric concentration, collected volume concentration is 65% ethanol eluate, concentrate, drying obtains purified balsam pear total saponins; Four, with purified balsam pear total saponins by half preparative high performance liquid chromatography instrument, and to collect retention time be the cut of 6.854min, cut concentrated again, freeze-drying obtains cucurbitane type balsam pear saponin(e.
3. according to the preparation method of the described cucurbitane type of claim 2 balsam pear saponin(e, it is characterized in that the ultrasonic time described in the step 1 is 45min.
4. according to the preparation method of the described cucurbitane type of claim 2 balsam pear saponin(e, it is characterized in that in the step 2 with AB-8 type macroporous resin adsorption 50min.
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| CN106174696A (en) * | 2016-08-17 | 2016-12-07 | 福建中烟工业有限责任公司 | Prepare the method for Fructus Momordicae charantiae extract, Fructus Momordicae charantiae extract and application thereof |
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| CN107556362B (en) * | 2017-09-15 | 2020-05-22 | 浙江大学 | Extraction method of cucurbitane type triterpenoid and medical application of cucurbitane type triterpenoid in resisting Alzheimer disease |
| CN109265510A (en) * | 2018-11-06 | 2019-01-25 | 广东省生物工程研究所（广州甘蔗糖业研究所） | A kind of tetracyclic triterpenoid and preparation method thereof |
| CN109833337A (en) * | 2019-01-18 | 2019-06-04 | 华南农业大学 | A kind of balsam pear chlorins compound inhibiting pest immune response and its high efficiency preparation method and application |
| CN109833337B (en) * | 2019-01-18 | 2021-08-03 | 华南农业大学 | Momordica charantia essence compound for inhibiting pest immune response and high-efficiency preparation method and application thereof |
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