CN101597317A - The purposes of the preparation method of Rhizoma Paridis saponin I and inhibition angiogenic growth thereof - Google Patents
The purposes of the preparation method of Rhizoma Paridis saponin I and inhibition angiogenic growth thereof Download PDFInfo
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- CN101597317A CN101597317A CNA2008101724166A CN200810172416A CN101597317A CN 101597317 A CN101597317 A CN 101597317A CN A2008101724166 A CNA2008101724166 A CN A2008101724166A CN 200810172416 A CN200810172416 A CN 200810172416A CN 101597317 A CN101597317 A CN 101597317A
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Abstract
The present invention relates to i.e. (25R)-Δ 5 (6)-alkene-spiral shell steroid-3-O-{ α-L-furans pectinose (1 → 4) of Rhizoma Paridis saponin I }-preparation method of [α-L-rhamnopyranosyl (1 → 2)]-3-O-β-D-glucopyranoside and the purposes of inhibition vasculogenesis thereof, after agent solvent extraction Paris polyphylla is arranged, prepare Rhizoma Paridis saponin I with silica gel and reverse phase silica gel chromatography, can be used as antitumor drug and use.
Description
Technical field
The present invention relates to a kind of Rhizoma Paridis saponin I that extraction separation obtains from Paris polyphylla, i.e. (25R)-Δ 5 (6)-alkene-spiral shell steroid-3-O-{ α-L-furans pectinose (l → 4) }-preparation method of [α-L-rhamnopyranosyl (l → 2)]-3-O-β-D-glucopyranoside (CAS number is 76296-72-5), and in the purposes that suppresses aspect the angiogenic growth.
Background technology
Paris polyphylla (Rhizoma Paridis) claims Paris polyphylla again, is the general term of Liliaceae paris plant, and the name head that stops with flea is stated from Shennong's Herbal.The paris plant whole world has 24 kinds, and China's most species has 19 kinds, and wherein each provinces and regions kind of southwest and resource are very abundant.Common kind has magnificent Paris polyphylla, Rhizoma Paridis and Paris polyphylla.Medicinal have magnificent Paris polyphylla, Rhizoma Paridis, Paris polyphylla, narrow leaf Paris polyphylla, long connective Paris polyphylla, rhizome of Pashan paris, the Paris polyphylla that reaches the clouds, a south heavy building." Chinese pharmacopoeia was put down in writing in the version in 2005, and the source of Paris polyphylla should be the dry rhizome of Rhizoma Paridis Paris polyphylla Smith var.yunnanensis (Franch.) Hand. one Mazz. and Rhizoma Paridis P.D phylla Smith var.chinensis (Franch.) Hara.Bitter, cold nature, slightly poisonous, return Liver Channel, have the effect of clearing heat and detoxicating, swelling and pain relieving, cool liver arresting convulsion, be used for diseases such as carbuncle sore, swelling and pain in the throat, venomous snake bite, traumatic pain, cool breeze tic.(Chinese Pharmacopoeia Commission. one one of Pharmacopoeia of People's Republic of China (version in 2005), Chemical Industry Press, 183.) do not see as yet so far about suppressing the report of blood vessel aspect.(open tree Pan. the chemical ingredients of paris plant and pharmacology activity research progress thereof. Strait Pharmaceutical Journal, 2007,19 (6): 4-7; Kang Liping, Ma Baiping, Zhang Jie, etc. the separation of steroidal saponin and structure are identified in the Paris polyphylla. Chinese pharmaceutical chemistry magazine, 2005,15 (1): 26-30; Wang Yu, Zhang Yanjun, Gao Wenyuan, etc. the antitumor activity component research of Rhizoma Paridis. CHINA JOURNAL OF CHINESE MATERIA MEDICA, 2007,32 (14): 1425-1428; HUANG Yun, WANG Qiang, CUI Li-jian.Primary Comments on Chemotaxonomy of spp, Basedon Saponins Analysis.Journal of Chinese Phar-maceutical iences 2005,14 (3): 176-180.)
Tumour is one of principal disease of present harm humans health.Occupy second of all kinds of disease death rates.A large amount of clinical treatments prove that chemotherapy and radiation also has great damage effect to normal cell in killing tumor cell.These therapies make the hemopoietic system of human body and immunologic function suffer severe impairment, very easily cause patient death.Dependency to blood vessel is that all tumour cells are common, vasculogenesis be tumor growth and shift in an important step, no matter primary tumor and secondary tumors, in case growth diameter surpasses 2mm, there is vasculogenesis in the capital, will be the tumour ramp thereupon, shifts to take place.(Folkman?J.what?isthe?evidence?that?tumors?are?angiogenesis?department？J?Natl?Cancer?Inst.1990，82：4-6.)
At present tumor treatment is mainly contained the three major types medicine, be respectively cell toxicity medicament, put, chemotherapy assisted class medicine, angiogenesis.Angiogenesis is the very promising antitumor drug of a class at present.
It with the chick chorioallantoic membrane model, screening has in the experiment of inhibiting compound angiogenic growth, and the Rhizoma Paridis saponin I-that obtains from Paris polyphylla i.e. (25R)-Δ 5 (6)-alkene-spiral shell steroid-3-O-{ α-L-furans pectinose (l → 4) }-[α-L-rhamnopyranosyl (l → 2)]-3-O-β-D-glucopyranoside shown angiogenic growth restraining effect preferably.
Summary of the invention
One of purpose of the present invention provides the preparation method of Rhizoma Paridis saponin I, and the purposes aspect the inhibition angiogenic growth.
The present invention relates to i.e. (25R)-Δ 5 (6)-alkene-spiral shell steroid-3-O-{ α-L-furans pectinose (l → 4) of extraction separation obtains from Paris polyphylla Rhizoma Paridis saponin I }-preparation method of [α-L-rhamnopyranosyl (l → 2)]-3-O-β-D-glucopyranoside (chemical structure is suc as formula 1).
The chemical structural formula of formula 1 Rhizoma Paridis saponin I
Its preparation method is as follows:
(1) get Paris polyphylla, the sherwood oil of doubly measuring with 6-15, ethyl acetate, 95% ethanol, 80% ethanol, 60% ethanol, water carry out supersound extraction successively, extract 3-5 time, and each 20min-100min after the filtration, obtains each position behind the supernatant liquor concentrating under reduced pressure.
(2) step (1) is obtained get ethyl acetate extract and disperse with an amount of ethanol after, the silica gel mixed sample that 1-3 doubly measures, 10-50 doubly measures silica gel dress post, last sample, use sherwood oil, sherwood oil successively: ethyl acetate, ethyl acetate, ethyl acetate: ethanol, ethanol elution obtain i.e. (25R)-Δ 5 (6)-alkene-spiral shell steroid-3-O-{ α-L-furans pectinose (l → 4) of Rhizoma Paridis saponin I }-[α-L-rhamnopyranosyl (l → 2)]-3-O-β-D-glucopyranoside crude product.
(3) the Rhizoma Paridis saponin I crude product that step (2) is obtained is further purified with silica gel, reverse phase silica gel method.Obtain i.e. (25R)-Δ 5 (6)-alkene-spiral shell steroid-3-O-{ α-L-furans pectinose (l → 4) of the Rhizoma Paridis saponin I shown in the formula (1) }-[α-L-rhamnopyranosyl (l → 2)]-3-O-β-pure product of D-glucopyranoside.
Embodiment is as follows:
Embodiment 1 Rhizoma Paridis saponin I i.e. (25R)-Δ 5 (6)-alkene-spiral shell steroid-3-O-{ α-L-furans pectinose (l → 4) }-preparation of [α-L-rhamnopyranosyl (l → 2)]-3-O-β-D-glucopyranoside gets the 2kg Paris polyphylla, use 3 supersound extraction of sherwood oil, ethyl acetate, 95% ethanol, 80% ethanol, 60% ethanol, moisture of 10 times of amounts successively, each 30min, after the filtration, obtain each position behind the supernatant liquor concentrating under reduced pressure.Collecting ethyl acetate extract, on silica gel (200～300 order) post, use the sherwood oil wash-out earlier, is 1: 1 sherwood oil, ethyl acetate, alcoholic acid mixed solution wash-out then with volume ratio.Collecting with volume ratio is the elutriant that obtains behind 1: 1 the sherwood oil, ethyl acetate, alcoholic acid mixed solution wash-out, and concentrating under reduced pressure obtains crude product, be further purified crystallization with silica gel, reverse phase silica gel method, obtain 10 gram monomeric compounds,, determine that structure is the Paris polyphylla saponin I through structure elucidation.
Rhizoma Paridis saponin I physical properties and spectral data are as follows:
Water white transparency needle or white powder are soluble in chloroform, methyl alcohol.
ESI-MS molecular weight: 854.466
Molecular formula: C
44H
70O
16
ESI-MS(m/z)：855(M
+)，722(M-Arb)，576(M-Arb-Rha)，415(M-Arb-Rha-Glu)，397(M-Arb-Rha-Glu-H
2O)，379(M-Arb-Rha-Glu-2H
2O)，283，271，253，251，213，199，173，159，147，139，129，107，93，85，69，55(100％)。
1HNMR(DMSO-d6)δppm：5.391(1H，d，J＝5.0Hz)，5.245(1H，d，J＝5.4Hz)，2.43，2.15(H-1)，1.8(H-2)，3.48(H-3)，1.8(H-4)，5.336(1H，br，H-6)，1.53(H-8)，0.9(H-9)，4.88(H-10)，1.5(H-11)，1.16(H-12)，1.8(H-13)，1.14(H-14)，1.93，1.90(H-15，17)，4.27(H-16)，3.4(H-17)，0.739(s，H-18)，0.964(H-19)，3.8(H-20)，1.82(H-20)，0.915(d，J＝6.7Hz，H-21)，1.53-1.60(H-24)，3.42，3.21(H-26)，0.739(d，H-27)。4.43(d，J＝7.8Hz，H-1′)，3.35(H-2′)，3.23(H-3′)，3.26(H-4′)，3.47(H-5′)，3.60(H-6′)，5.037(s，H-1″)，3.64(H-2″)，3.41(H-3″)，3.19(H-4″)，3.99(H-5″)，1.089(d，J＝6.0Hz，H-6″)，4.88(H-1′″)，3.68(H-3′″)，3.86(H-4′″)，3.67(H-5′″)。
13CNMR(DMSO-d6)δppm：38.1(C-1)，29.5(C-2)，76.5(C-3)，37.3(C-4)，140.7(C-5)，121.7(C-6)，32.0(C-7)，30.3(C-8)，50.0(C-9)，36.9(C-10)，20.8(C-11)，39.9(C-12)，40.5(C-13)，56.2(C-14)，32.0(C-15)，80.7(C-16)，62.2(C-17)，16.5(C-18)，19.4(C-19)，41.6(C-20)，15.1(C-21)，108.9(C-22)，31.4(C-23)，28.9(C-24)，31.4(C-25)，66.4(C-26)，17.6(C-27)，98.4(C-1′)，81.8(C-2′)，76.4(C-3′)，75.4(C-4′)，76.1(C-5′)，61.8(C-6′)，100.5(C-1″)，70.9(C-2″)，71.0(C-3″)，72.3(C-4″)，68.4(C-5″)，18.2(C-6″)，108.2(C-1′″)，82.4(C-2′″)，76.8(C-3′″)，84.9(C-4′″)，60.4(C-5′″)。
The invention still further relates to Rhizoma Paridis saponin I that structural formula is shown below and suppress the purposes of angiogenic growth.Experimental example Rhizoma Paridis saponin I i.e. (25R)-Δ 5 (6)-alkene-spiral shell steroid-3-O-{ α-L-furans pectinose (l → 4) }-experimental study of the inhibition angiogenic growth of [α-L-rhamnopyranosyl (l → 2)]-3-O-β-D-glucopyranoside
1 model name: chick chorioallantoic membrane model
2 test methods
Precision takes by weighing Rhizoma Paridis saponin I, uses dissolve with ethanol, is mixed with the solution that concentration is about 0.4mg/ml, and is standby.Selective body quality close (50.4-5) g, epidermis is pollution-free, unabroken fresh kind of egg, places hatch 7 days of 37.8 ± 0.5 ℃ of temperature, relative humidity 65%-70%, and each upset of morning, noon and afternoon every day is once.Gelfoam is made the circular fritter that diameter is about 6mm with punch tool, use microsyringe dosing in fritter under the gnotobasis.Positive drug and sample all add 5 μ l.After treating that gelfoam is with the complete absorption dehydration of medicine, place under the ultraviolet lamp sterilization air-dry.Put into 37 ℃ of incubators after the sterilization of kind of egg, air chamber upwards to incubation the 7th day, will be planted egg and be divided into 6 groups at random, 15 pieces every group.Disinfect the egg embryo in alcohol back and bore an aperture with dental burr on egg embryo top on super clean bench, eggshell and shell membrane around removing carefully then make opening be about 1.2cm * 1.2cm size; Determine to needle cameral mantle with injection needles from air chamber and yolk separated place carefully behind the application of sample position, inject 1～2 sterilized water, cameral mantle and CAM film are separated, remove the cameral mantle on upper strata then with tweezers gently, expose the CAM film of lower floor.Gelfoam fritter after dosing and the sterilization is placed relative avascular area between two anterior vitelline veins in nearly embryo head 1cm place.Scotch-tape sealing closes the chorion mouth, hatches 2d for 37.8 ± 0.5 ℃.Chicken embryo after the administration is hatched 2 in 37.8 ± 0.5 ℃ constant temperature incubator after, take out, tear hinge off, with the chick chorioallantoic membrane blood vessel curing 10min of methyl alcohol-acetone (1: 1) with dosing, carefully peel the CAM film, is that the center of circle is cut into the circle that diameter is about 2cm with eye scissors with the gelfoam with chick chorioallantoic membrane, places on the slide glass, examines under a microscope, takes a picture.(X ± S) expression uses nonparameter test to data, uses the SAS statistical software and carries out relatively each group difference of one-way analysis of variance with mean ± standard deviation.
3 test-results
Blood vessel is added up according to diameter, data are divided into large, medium and small Three Estate.Data are with mean ± standard error (X ± S) expression.The experimental data statistics is as follows:
Annotate: compare * * P＜0.01 with the blank group
Because great vessels and medium vessels just formed before administration, therefore, we mainly analyze little blood vessel when analytical data.Test-results shows: the administration group has significance meaning (P＜0.01) with blank group comparing difference.
4 conclusion (of pressure testing)s
Pharmacodynamic experiment shows that The compounds of this invention Rhizoma Paridis saponin I has the activity of good inhibition angiogenic growth, possesses to be prepared into to have the due activity of antitumor drug that suppresses the angiogenic growth effect, has broad application prospects.
Claims (2)
1 Rhizoma Paridis saponin I i.e. (25R)-Δ 5 (6)-alkene-spiral shell steroid-3-O-{ α-L-furans pectinose (1 → 4) }-[α-L-rhamnopyranosyl (1 → 2)]-3-O-β-D-glucopyranoside (chemical structure is as follows), it is characterized in that its preparation method is as follows:
(1) get Paris polyphylla, the sherwood oil of doubly measuring with 6-15, ethyl acetate, 95% ethanol, 80% ethanol, 60% ethanol, water carry out supersound extraction successively, extract 3-5 time, and each 20min-100min after the filtration, obtains each position behind the supernatant liquor concentrating under reduced pressure.
(2) step (1) is obtained get ethyl acetate extract and disperse with an amount of ethanol after, the silica gel mixed sample that 1-3 doubly measures, 10-50 doubly measures silica gel dress post, last sample, use sherwood oil, sherwood oil successively: ethyl acetate, ethyl acetate, ethyl acetate: ethanol, ethanol elution obtain i.e. (25R)-Δ 5 (6)-alkene-spiral shell steroid-3-O-{ α-L-furans pectinose (1 → 4) of Rhizoma Paridis saponin I }-[α-L-rhamnopyranosyl (1 → 2)]-3-O-β-D-glucopyranoside crude product.
(3) the Rhizoma Paridis saponin I crude product that step (2) is obtained is further purified with silica gel, reverse phase silica gel method.Obtain i.e. (25R)-Δ 5 (6)-alkene-spiral shell steroid-3-O-{ α-L-furans pectinose (1 → 4) of the Rhizoma Paridis saponin I shown in the formula (1) }-[α-L-rhamnopyranosyl (1 → 2)]-3-O-β-pure product of D-glucopyranoside.
The described Rhizoma Paridis saponin I of 2 claims 1, the purposes of inhibition angiogenic growth.
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| WO2015158163A1 (en) * | 2014-04-14 | 2015-10-22 | 四川京华创生物科技有限公司 | Cyclopentanoperhydrophenanthrene framework compounds and preparation method therefor |
| CN105796580A (en) * | 2014-12-31 | 2016-07-27 | 上海中医药大学附属龙华医院 | Use of proteasome activity inhibitor PI in preparation of drug or health food for preventing and treating osteosarcoma |
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| CN107619427A (en) * | 2017-11-03 | 2018-01-23 | 隆安县荣胜养殖有限公司 | A kind of method of the extraction purification rhizoma paridis saponin I from Paris polyphylla |
| CN107619427B (en) * | 2017-11-03 | 2020-09-15 | 广西南宁成远科技有限公司 | Method for extracting and purifying rhizoma paridis saponin I from rhizoma paridis |
| CN108853128A (en) * | 2018-06-05 | 2018-11-23 | 湖北医药学院 | A kind of Rhizoma Paridis extract is preparing the application in the drug for treating human prostata cancer |
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