CN105106556A - Chemical component separation and identification method for Parisforrestii (Takht.) H. Li antitumor activity part PFE-PT3 - Google Patents

Chemical component separation and identification method for Parisforrestii (Takht.) H. Li antitumor activity part PFE-PT3 Download PDF

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CN105106556A
CN105106556A CN201510578102.6A CN201510578102A CN105106556A CN 105106556 A CN105106556 A CN 105106556A CN 201510578102 A CN201510578102 A CN 201510578102A CN 105106556 A CN105106556 A CN 105106556A
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rhizoma paridis
saponin
pfe
paridis saponin
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CN105106556B (en
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王跃虎
牛红梅
杨珺
罗吉凤
梅任强
杨永平
李恒
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Kunming Institute of Botany of CAS
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Abstract

The invention provides a Parisforrestii (Takht.) H. Li antitumor activity part PFE-PT3 and an extraction and identification method for chemical components in the Parisforrestii (Takht.) H. Li antitumor activity part PFE-PT3. By means of a separation method of chromatographic column chromatography and semi-preparation high performance liquid chromatography and an identification method of a mass spectrum and a nuclear magnetic resonance spectrum, polyphyllin I, polyphyllin II, polyphyllin III, polyphyllin V, polyphyllin H, pennogenin-3-O-alpha-L-rhamnopyranosyl-(1-<>Z4)-[alpha-L-rhamnopyranosyl-(1->2)]-beta-D-glucopyranoside (PGRR), methyl polyphyllin I, methyl polyphyllin V, PariposideA and beta-ecdysone are separated from and identified in PFE-PT3. The main chemical components of PFE-PT3 are illuminated for the first time, the chemical components can be easily and rapidly obtained from PFE-PT3 through the method, and the method can be used for establishing the quality control standard of PFE-PT3.

Description

The chemical composition separation andpreconcentration method of Rhizoma Paridis forrestii active anticancer position PFE-PT3
Technical field:
The invention belongs to natural product extraction separation technology field, particularly relate to the chemical composition separation andpreconcentration method of Rhizoma Paridis forrestii active anticancer position PFE-PT3.
Background technology:
Rhizoma Paridis forrestii [Parisforrestii (Takht.) H.Li] is Trilliaceae paris plant, its rhizome is used as medicine, there is effect of heat-clearing and toxic substances removing, reducing swelling and alleviating pain, the arresting convulsion of cool liver, be used for the treatment of ulcer sores, innominate toxic swelling, venom, laryngopharynx swelling and pain, parotitis, tonsillitis and epidemic infection with swollen head (Zhu Zhaoyun. Yunnan natural drug illustrated handbook. the 6th volume. Kunming: Yunnan Science Press, 2010:127).Patent " plant amedica of a kind of Therapeutic cancer and preparation method thereof and application " (publication No.: CN104706896A) discloses Rhizoma Paridis forrestii PFE-PT3 position and has remarkable active anticancer, but its chemical composition there is not been reported.Illustrate the chemical substance basis of PFE-PT3, to the quality control standard setting up PFE-PT3, and significant based on the new drug development of PFE-PT3.
Summary of the invention:
The present invention is directed to prior art and be present in the problems referred to above, Rhizoma Paridis forrestii [Parisforrestii (Takht.) H.Li] active anticancer position PFE-PT3 is provided, with the pharmaceutical composition that it is active component, and the extraction of chemical composition in PFE-PT3 and authentication method.Because PFE-PT3 has significant active anticancer, but its chemical composition is unclear, has no idea to set up quality control standard.So, the invention provides a kind of PFE-PT3 isolation and identification method for solving this technical problem.
In order to realize above-mentioned purpose of the present invention, the invention provides following technical scheme:
Pharmaceutical composition, the Rhizoma Paridis forrestii n-butanol extraction position PFE-PT3 wherein containing treatment effective dose and pharmaceutically acceptable carrier, described PFE-PT3 is prepared by following method and obtains: Rhizoma Paridis forrestii dry rhizome, pulverize rear 95% soak with ethanol 7 days, filter, filtering residue continues to extract, altogether extract 4 times, merging filtrate, recycling design, obtains extractum, extractum water is made suspension, be extracted with ethyl acetate, reclaim ethyl acetate, obtain Ethyl acetate fraction; Mother solution after extraction into ethyl acetate, continuation n-butanol extraction, reclaims n-butyl alcohol, obtains n-butanol extraction position and PFE-PT3.
Pharmaceutical composition, Rhizoma Paridis forrestii n-butanol extraction position PFE-PT3 wherein containing treatment effective dose and pharmaceutically acceptable carrier, in described PFE-PT3, Rhizoma Paridis saponin I, Rhizoma Paridis saponin II, Rhizoma Paridis saponin III, Rhizoma Paridis saponin V, Rhizoma Paridis saponin H, pennogenin-3-O-α-L-rhamnopyranosyl-(1 → 4)-[α-L-rhamnopyranosyl-(1 → 2)]-β-D-pyranglucoside (PGRR), methyl original weight building saponin I, methyl former Rhizoma Paridis saponin V, PariposideA and β-ecdyson total content are 10-95% (weight).
Pharmaceutical composition, Rhizoma Paridis forrestii n-butanol extraction position PFE-PT3 wherein containing treatment effective dose and pharmaceutically acceptable carrier, Rhizoma Paridis saponin I in described PFE-PT3, Rhizoma Paridis saponin II, Rhizoma Paridis saponin III, Rhizoma Paridis saponin V, Rhizoma Paridis saponin H, pennogenin-3-O-α-L-rhamnopyranosyl-(1 → 4)-[α-L-rhamnopyranosyl-(1 → 2)]-β-D-pyranglucoside (PGRR), methyl original weight building saponin I, the former Rhizoma Paridis saponin V of methyl, PariposideA with β-ecdyson is separated from Rhizoma Paridis forrestii n-butanol extraction position PFE-PT3 to obtain, step is:
(1) PFE-PT3 is through silica gel column chromatography 10:1, and the chloroform-methanol mixed solvent gradient elution section of drawing of 5:1,3:1,1:1, obtains 4 parts such as Fr.A, Fr.B, Fr.C and Fr.D;
(2) Fr.B part is got through C 18reversed-phase silica gel column chromatography, the methanol-water of 10:90 → 100:0, obtains Fr.B 1, Fr.B 2, Fr.B 3, Fr.B 4, Fr.B 5and Fr.B 6deng 6 parts;
(3) Fr.B is got 3part, cross LH-20 gel filtration chromatography, after methanol-eluted fractions, the chloroform-methanol eluting of recycle silicon plastic column chromatography 5:1 obtains β-ecdyson;
(4) Fr.B is got 4part, purifies with half preparative high-performance liquid chromatographic and obtains methyl original weight building saponin I, and the former Rhizoma Paridis saponin V of methyl;
(5) Fr.B is got 5part, purifies with half preparative high-performance liquid chromatographic and obtains PariposideA, Rhizoma Paridis saponin II, Rhizoma Paridis saponin III, Rhizoma Paridis saponin I and Rhizoma Paridis saponin V;
(6) Fr.B is got 6part, half preparative high-performance liquid chromatographic purification obtains compound PGRR and Rhizoma Paridis saponin H;
Wherein, half preparative high-performance liquid chromatographic described in (4) is with Agilent 1200 chromatograph of liquid, ZorbaxSB-C 18chromatographic column, chromatographic column size 9.4 × 250mm, eluant is methanol-water, ratio 72:28, flow velocity 2mL/min; (5) half preparative high-performance liquid chromatographic described in is with Agilent 1200 chromatograph of liquid, ZorbaxSB-C 18chromatographic column, chromatographic column size 9.4 × 250mm, eluant is acetonitrile-water, ratio 50:50, flow velocity 2mL/min; (6) half preparative high-performance liquid chromatographic described in is with Agilent 1200 chromatograph of liquid, ZorbaxSB-C 18chromatographic column, chromatographic column size 9.4 × 250mm, eluant is acetonitrile-water, ratio 40:60, flow velocity 2mL/min.
Present invention also offers Rhizoma Paridis saponin I in Rhizoma Paridis forrestii extract n-butanol extraction position PFE-PT3, Rhizoma Paridis saponin II, Rhizoma Paridis saponin III, Rhizoma Paridis saponin V, Rhizoma Paridis saponin H, pennogenin-3-O-α-L-rhamnopyranosyl-(1 → 4)-[α-L-rhamnopyranosyl-(1 → 2)]-β-D-pyranglucoside (PGRR), methyl original weight building saponin I, the former Rhizoma Paridis saponin V of methyl, PariposideA and β-ecdyson total content is 10-95% (weight), it is separated and obtains from Rhizoma Paridis forrestii n-butanol extraction position PFE-PT3, step is:
(1) PFE-PT3 is through silica gel column chromatography 10:1, and the chloroform-methanol mixed solvent gradient elution section of drawing of 5:1,3:1,1:1, obtains 4 parts such as Fr.A, Fr.B, Fr.C and Fr.D;
(2) Fr.B part is got through C 18reversed-phase silica gel column chromatography, the methanol-water of 10:90 → 100:0, obtains Fr.B 1, Fr.B 2, Fr.B 3, Fr.B 4, Fr.B 5and Fr.B 6deng 6 parts;
(3) Fr.B is got 3part, cross LH-20 gel filtration chromatography, after methanol-eluted fractions, the chloroform-methanol eluting of recycle silicon plastic column chromatography 5:1 obtains β-ecdyson;
(4) Fr.B is got 4part, purifies with half preparative high-performance liquid chromatographic and obtains methyl original weight building saponin I, and the former Rhizoma Paridis saponin V of methyl;
(5) Fr.B is got 5part, purifies with half preparative high-performance liquid chromatographic and obtains PariposideA, Rhizoma Paridis saponin II, Rhizoma Paridis saponin III, Rhizoma Paridis saponin I and Rhizoma Paridis saponin V;
(6) Fr.B is got 6part, half preparative high-performance liquid chromatographic purification obtains compound PGRR and Rhizoma Paridis saponin H;
Wherein, half preparative high-performance liquid chromatographic described in (4) is with Agilent 1200 chromatograph of liquid, ZorbaxSB-C 18chromatographic column, chromatographic column size 9.4 × 250mm, eluant is methanol-water, ratio 72:28, flow velocity 2mL/min; (5) half preparative high-performance liquid chromatographic described in is with Agilent 1200 chromatograph of liquid, ZorbaxSB-C 18chromatographic column, chromatographic column size 9.4 × 250mm, eluant is acetonitrile-water, ratio 50:50, flow velocity 2mL/min; (6) half preparative high-performance liquid chromatographic described in is with Agilent 1200 chromatograph of liquid, ZorbaxSB-C 18chromatographic column, chromatographic column size 9.4 × 250mm, eluant is acetonitrile-water, ratio 40:60, flow velocity 2mL/min.
The chemical composition isolation and identification method of a kind of Rhizoma Paridis forrestii n-butanol extraction position PFE-PT3, be separated from Rhizoma Paridis forrestii n-butanol extraction position PFE-PT3 and obtain Rhizoma Paridis saponin I, Rhizoma Paridis saponin II, Rhizoma Paridis saponin III, Rhizoma Paridis saponin V, Rhizoma Paridis saponin H, pennogenin-3-O-α-L-rhamnopyranosyl-(1 → 4)-[α-L-rhamnopyranosyl-(1 → 2)]-β-D-pyranglucoside (PGRR), methyl original weight building saponin I, methyl former Rhizoma Paridis saponin V, PariposideA and β-ecdyson, step is:
(1) PFE-PT3 is through silica gel column chromatography 10:1, and the chloroform-methanol mixed solvent gradient elution section of drawing of 5:1,3:1,1:1, obtains 4 parts such as Fr.A, Fr.B, Fr.C and Fr.D;
(2) Fr.B part is got through C 18reversed-phase silica gel column chromatography, the methanol-water of 10:90 → 100:0, obtains Fr.B 1, Fr.B 2, Fr.B 3, Fr.B 4, Fr.B 5and Fr.B 6deng 6 parts;
(3) Fr.B is got 3part, cross LH-20 gel filtration chromatography, after methanol-eluted fractions, the chloroform-methanol eluting of recycle silicon plastic column chromatography 5:1 obtains β-ecdyson;
(4) Fr.B is got 4part, purifies with half preparative high-performance liquid chromatographic and obtains methyl original weight building saponin I, and the former Rhizoma Paridis saponin V of methyl;
(5) Fr.B is got 5part, purifies with half preparative high-performance liquid chromatographic and obtains PariposideA, Rhizoma Paridis saponin II, Rhizoma Paridis saponin III, Rhizoma Paridis saponin I and Rhizoma Paridis saponin V;
(6) Fr.B is got 6part, half preparative high-performance liquid chromatographic purification obtains compound PGRR and Rhizoma Paridis saponin H;
Wherein, half preparative high-performance liquid chromatographic described in (4) is with Agilent 1200 chromatograph of liquid, ZorbaxSB-C 18chromatographic column, chromatographic column size 9.4 × 250mm, eluant is methanol-water, ratio 72:28, flow velocity 2mL/min; (5) half preparative high-performance liquid chromatographic described in is with Agilent 1200 chromatograph of liquid, ZorbaxSB-C 18chromatographic column, chromatographic column size 9.4 × 250mm, eluant is acetonitrile-water, ratio 50:50, flow velocity 2mL/min; (6) half preparative high-performance liquid chromatographic described in is with Agilent 1200 chromatograph of liquid, ZorbaxSB-C 18chromatographic column, chromatographic column size 9.4 × 250mm, eluant is acetonitrile-water, ratio 40:60, flow velocity 2mL/min.
According to the chemical composition isolation and identification method of described a kind of Rhizoma Paridis forrestii n-butanol extraction position PFE-PT3, the method is separated and obtains 10 compounds from PFE-PT3, by mass spectrum MS and NMR (Nuclear Magnetic Resonance) spectrum NMR, it is carried out to the determination of chemical constitution.
According to the chemical composition isolation and identification method of described a kind of Rhizoma Paridis forrestii n-butanol extraction position PFE-PT3, the method obtains chemical composition Rhizoma Paridis saponin I from PFE-PT3, Rhizoma Paridis saponin II, Rhizoma Paridis saponin III, Rhizoma Paridis saponin V, Rhizoma Paridis saponin H, pennogenin-3-O-α-L-rhamnopyranosyl-(1 → 4)-[α-L-rhamnopyranosyl-(1 → 2)]-β-D-pyranglucoside (PGRR), methyl original weight building saponin I, the former Rhizoma Paridis saponin V of methyl, PariposideA and β-ecdyson, for setting up the quality control standard of PFE-PT3.
The application of described Rhizoma Paridis forrestii n-butanol extraction position PFE-PT3 in the medicine preparing treatment or prophylaxis of cancer disease.
According to the application of described Rhizoma Paridis forrestii n-butanol extraction position PFE-PT3 in the medicine preparing treatment or prophylaxis of cancer disease, the cancer described in it is hepatocarcinoma, pulmonary carcinoma, breast carcinoma, colon cancer.
Prepare the method for the pharmaceutical composition of above-mentioned treatment or prophylaxis of cancer, mix by following percentage by weight: Rhizoma Paridis forrestii n-butanol extraction position PFE-PT3 accounts for 20-80%, dispersant 2-20%, disintegrating agent 3-5%, emulsifying agent 3-8%, binding agent 0.2-2%, wetting agent 0.5-10%, all the other are filler.
Compared with prior art, the present invention has following excellent beneficial effect: Rhizoma Paridis forrestii extract, particularly n-butanol extraction position (PFE-PT3) has extremely significant inhibit activities to SMMC-7721 liver cancer cells, lung cancer cell A-549, MCF-7 Breast Cancer Cell and colon cancer SW480 cell, and its activity is better than positive control medicine cisplatin.The present invention illustrates the main chemical compositions of Rhizoma Paridis forrestii active anticancer position PFE-PT3 first, and these compositions may be used for the quality control standard of working out PFE-PT3.
Detailed description of the invention:
Further illustrate essentiality content of the present invention with embodiments of the invention below, but do not limit the present invention with this.
Embodiment 1:
The preparation of PFE-PT3 of the present invention and the separation of contained chemical composition thereof:
The preparation of PFE-PT3: Rhizoma Paridis forrestii [Parisforrestii (Takht.) H.Li] dry rhizome (4.4kg), soaks 7 days with 95% ethanol (13L) after pulverizing, and filters, and filtering residue continues to extract.Altogether extract 4 times, merging filtrate, recycling design, obtains extractum (numbering PFE-PT1) 550g.PFE-PT1 water (2L) is made suspension, is extracted with ethyl acetate (2L × 3), reclaim ethyl acetate, obtain Ethyl acetate fraction (numbering PFE-PT2) 19g.Mother solution after extraction into ethyl acetate, continues, with n-butanol extraction (2L × 3), to reclaim n-butyl alcohol, obtain n-butanol extraction position (numbering PFE-PT3) 290g.
The separation of chemical composition contained by PFE-PT3:
Getting weight is that the PFE-PT3 of 180g is through silica gel column chromatography chloroform-methanol mixed solvent gradient (10:1,5:1,3:1,1:1) the eluting section of drawing, obtains Fr.A (14g), Fr.B (101g), Fr.C (45g) and Fr.D (12g) 4 parts.Get Fr.B part 30g through C 18reversed-phase silica gel column chromatography (methanol-water, 10:90 → 100:0), obtains Fr.B 1(1.0g), Fr.B 2(0.5g), Fr.B 3(0.8g), Fr.B 4(4.6g), Fr.B 5(16.1g) and Fr.B 6(1.0g) 6 parts.
Get Fr.B 3part 150mg, after crossing LH-20 gel filtration chromatography (methanol-eluted fractions), recycle silicon plastic column chromatography chloroform-methanol (5:1) eluting obtains β-ecdyson (39.0mg).Get Fr.B 4part 130mg, by half preparative high-performance liquid chromatographic (Agilent 1200, ZorbaxSB-C 18chromatographic column, 9.4 × 250mm; Methanol-water, 72:28, flow velocity 2mL/min) purification obtains methyl original weight building saponin I (30.0mg, retention time 25.313min) and the former Rhizoma Paridis saponin V of methyl (14.0mg, retention time 27.236min).Get Fr.B 5part 120mg, by half preparative high-performance liquid chromatographic (Agilent 1200, ZorbaxSB-C 18chromatographic column, 9.4 × 250mm; Acetonitrile-water, 50:50, flow velocity 2mL/min) purification obtains PariposideA (4.5mg, retention time 12.788min), Rhizoma Paridis saponin II (1.4mg, retention time 14.634min), Rhizoma Paridis saponin III (14.4mg, retention time 18.070min), Rhizoma Paridis saponin I (12.7mg, retention time 21.019min) and Rhizoma Paridis saponin V (4.4mg, retention time 26.029min).Get Fr.B 6part 132mg, half preparative high-performance liquid chromatographic (Agilent 1200, ZorbaxSB-C 18chromatographic column, 9.4 × 250mm; Acetonitrile-water, 40:60, flow velocity 2mL/min) purification obtains compound PGRR (4.1mg, retention time 18.421min) and Rhizoma Paridis saponin H (9.0mg, retention time 23.587min).
Embodiment 2
The Structural Identification of PFE-PT3 chemical composition of the present invention:
Rhizoma Paridis saponin I, white solid, molecular formula C 44h 70o 16, CAS registration number 50773-41-6. 1HNMR(C 5D 5N，500MHz)δ:6.28(1H,brs),5.92(1H,d,J＝1.4Hz),5.29(1H,d,J＝5.1Hz),1.76(3H,d,J＝6.2Hz),1.12(3H,d,J＝7.0Hz),1.03(3H,s),0.81(3H,s),0.68(3H,d,J＝5.6Hz)。 13CNMR(C 5D 5N,125MHz)δ:140.6,121.7,109.5,109.1,101.8,100.0,86.6,82.6,81.0,77.9,77.7,77.6,77.3,76.8,76.6,74.0,72.7,72.4,69.4,66.7,62.8,62.4,61.2,56.5,50.1,41.8,40.3,39.7,38.8,37.4,37.0,32.2,32.1,31.7,31.5,30.5,30.0,29.1,21.0,19.3,18.6,17.2,16.2,14.9。ESIMSm/z853[M-H] -。Its NMR data with document [Wang Yu, Gao Wenyuan, Yuan Lichun, Liu Xinqiao, Wang Shujun, Chen Cui. the chemical constitution study of Rhizoma Paridis. Chinese herbal medicine, 2007,38 (1): 17-20] in data basically identical.
Rhizoma Paridis saponin II, white solid, molecular formula C 51h 82o 20, CAS registration number 50773-42-7. 1HNMR(C 5D 5N，500MHz)δ：6.42(1H,brs),6.30(1H,d,J＝1.2Hz),5.85(1H,s),5.30(1H,d,J＝5.1Hz),1.76(3H,d,J＝6.2Hz),1.59(3H,d,J＝6.1Hz),1.58(3H,d,J＝6.1Hz),1.12(3H,d,J＝7.0Hz),1.04(3H,s),0.81(3H,s),0.68(3H,d,J＝5.7Hz)。 13CNMR(C 5D 5N，125MHz)δ：140.6,121.7,109.1,103.2,102.1×2,100.2,81.0,80.3,77.9,77.8,77.6,77.5,76.9,74.0,73.9,73.2,72.8,72.7,72.6,72.4,70.3,69.5,68.2,66.7,62.8,61.1,56.5,50.2,41.8,40.3,39.7,38.8,37.4,37.0,32.2,32.1,31.7,31.6,30.5,30.0,29.2,21.0,19.3,18.8,18.6,18.3,17.2,16.2,14.9。ESIMSm/z1013[M-H] -。Its NMR data with document [Wang Yu, Gao Wenyuan, Yuan Lichun, Liu Xinqiao, Wang Shujun, Chen Cui. the chemical constitution study of Rhizoma Paridis. Chinese herbal medicine, 2007,38 (1): 17-20] in data basically identical.
Rhizoma Paridis saponin III, white solid, molecular formula C 45h 72o 16, CAS registration number 19057-60-4. 1HNMR(C 5D 5N，500MHz)δ:6.41(1H,brs),5.86(1H,s),5.30(1H,d,J＝5.1Hz),1.76(3H,d,J＝6.3Hz),1.63(3H,d,J＝6.2Hz),1.12(3H,d,J＝7.0Hz),1.04(3H,s),0.81(3H,s),0.68(3H,d,J＝5.5Hz)。 13CNMR(C 5D 5N，125MHz)δ:140.6,121.7,109.1,102.8,101.9,100.1,81.0,78.4,77.9,77.8,77.6,76.8,74.0,73.8,72.7,72.6,72.5,72.4,70.3,69.4,66.7,62.8,61.1,56.5,50.2,41.8,40.3,39.7,38.8,37.4,37.0,32.2,32.1,31.7,31.6,30.5,30.0,29.1,21.0,19.3,18.5,18.4,17.2,16.2,14.9。ESIMSm/z867[M-H] -。Its NMR data with document [South Sea letter, Yin Hao, Yvonne. the chemical constitution study of water coconut palm, Chinese Sea medicine, 2008,27 (1), 40-42] in data basically identical.
Rhizoma Paridis saponin V, white solid, C 39h 62o 12, CAS registration number 19057-67-1. 1HNMR(C 5D 5N，500MHz)δ:6.40(1H,brs),5.29(1H,d,J＝5.1Hz),1.78(3H,d,J＝6.2Hz),1.13(3H,d,J＝7.0Hz),1.05(3H,s),0.81(3H,s),0.68(3H,d,J＝5.6Hz)。 13CNMR(C 5D 5N，125MHz)δ:140.7,121.6,109.1,102.0,100.2,81.0,79.6,78.2,77.8,77.7,74.1,72.8,72.5,71.7,69.4,66.7,62.8,62.5,56.5,50.1,41.8,40.3,39.7,38.9,37.4,37.0,32.2,32.1,31.7,31.6,30.5,30.1,29.2,21.0,19.3,18.6,17.2,16.2,14.9。ESIMSm/z721[M-H] -。Its NMR data with document [Li Zhongqiong, Lin Ruichao, Fu Wen, Wang Gangli, Wei Feng, Hang Taijun. Caulis et Folium Lactucae sativae flower chemical composition research. Chinese herbal medicine, 2001,32 (2): 101-104] in data basically identical.
Rhizoma Paridis saponin H, white solid, molecular formula C 44h 70o 17, CAS registration number 81917-50-2.δ： 1HNMR(C 5D 5N，500MHz)δ:6.28(1H,brs),5.92(1H,d,J＝1.3Hz),5.27(1H,d,J＝5.1Hz),1.76(3H,d,J＝6.2Hz),1.22(3H,d,J＝7.2Hz),1.07(3H,s),0.94(3H,s),0.66(3H,d,J＝5.9Hz)。 13CNMR(C 5D 5N,125MHz)δ:140.6,121.7,109.7,109.5,101.8,100.0,90.0,89.9,86.5,82.6,77.9,77.7,77.6,77.3,76.8,76.6,74.0,72.6,72.4,69.4,66.6,62.4,61.2,52.9,50.1,45.0,44.6,38.8,37.4,37.0,32.3,32.2,32.0,31.7,30.3,30.0,28.7,20.8,19.3,18.5,17.2,17.0,9.7。ESIMSm/z869[M-H] -。Its NMR data with document [Wang Yu, Gao Wenyuan, Yuan Lichun, Liu Xinqiao, Wang Shujun, Chen Cui. the chemical constitution study of Rhizoma Paridis. Chinese herbal medicine, 2007,38 (1): 17-20] in data basically identical.
Pennogenin-3-O-α-L-rhamnopyranosyl-(1 → 4)-[α-L-rhamnopyranosyl-(1 → 2)]-β-D-pyranglucoside (PGRR), white solid, molecular formula C 45h 72o 17, CAS registration number 55916-52-4. 1HNMR(C 5D 5N，500MHz)δ:6.41(1H,brs),5.86(1H,brs),5.28(1H,d,J＝5.2Hz),1.76(3H,d,J＝6.2Hz),1.63(3H,d,J＝6.2Hz),1.22(3H,d,J＝7.2Hz),1.07(3H,s),0.94(3H,s),0.67(3H,d,J＝5.8Hz)。 13CNMR(C 5D 5N，125MHz)δ:140.6,121.7,109.7,102.8,101.9,100.1,90.0,89.9,78.4,77.9,77.8,77.6,76.8,74.0,73.8,72.7,72.6,72.5,72.4,70.3,69.4,66.6,61.1,52.9,50.1,45.0,44.6,38.8,37.4,37.0,32.3,32.2,32.0×2,31.7,30.3,30.0,28.7,20.8,19.3,18.5,18.4,17.2,17.0,9.7。ESIMSm/z883[M-H] -。Its NMR data with document [Hua Dong, Liu Yang, Wang Xiayin, Lu Yunyang, Li Hui, soup seapeak. wide leaf Rhizoma Paridis chemical constitution study. Central-South pharmacy, 2015,13 (1): 43-46] in data basically identical.
Methyl original weight building saponin I, white solid, molecular formula C 51h 84o 22, CAS registration number 78101-18-5. 1HNMR(C 5D 5N,500MHz)δ:6.26(1H,brs),5.90(1H,d,J＝1.1Hz),5.29(1H,brs),4.93(1H,d,J＝7.4Hz),4.82(1H,d,J＝7.9Hz),3.24(3H,s),1.74(3H,d,J＝6.2Hz),1.17(3H,d,J＝6.9Hz),1.02(3H,s),0.97(3H,d,J＝6.7Hz),0.79(3H,s)。 13CNMR(C 5D 5N,125MHz)δ:140.6,121.7,112.5,109.4,104.8,101.8,100.0,86.5,82.5,81.1,78.5,78.4,77.9,77.7,77.5,77.3,76.8,76.5,75.1,75.0,73.9,72.6,72.3,71.6,69.3,64.0,62.7,62.3,61.2,56.4,50.1,47.1,40.6,40.3,39.6,38.9,37.3,37.0,34.0,32.1,32.0,31.5,30.6,30.0,28.0,20.9,19.2,18.5,17.0,16.2,16.1。ESIMSm/z1047[M-H] -。This compound is at document [MiyamuraM, NakanoK, NoharaT, TomimatsuT, KawasakiT.SteroidsaponinsfromParispolyphyllaSm.-Suppleme nt.Chem.Pharm.Bull., 1982,30 (2): 712-718] there is report in, but do not have in the document 13cNMR data, the present invention provides it first 13cNMR data.
The former Rhizoma Paridis saponin V of methyl, white solid, molecular formula C 46h 76o 18, CAS registration number 84774-05-0. 1HNMR(C 5D 5N,500MHz)δ:6.38(1H,brs),5.30(1H,d,J＝5.0Hz),3.25(3H,s),1.77(3H,d,J＝6.2Hz),1.17(3H,d,J＝6.9Hz),1.03(3H,s),0.98(3H,d,J＝6.7Hz),0.79(3H,s)。 13CNMR(C 5D 5N,125MHz)δ:140.7,121.6,112.5,104.9,102.0,100.2,81.2,79.5,78.5,78.4,78.2,77.8,77.7,75.1,75.0,74.0,72.7,72.5,71.7,71.6,69.4,64.0,62.7,62.5,56.4,50.1,47.1,40.6,40.3,39.6,38.8,37.4,37.0,34.1,32.2,32.0,31.5,30.7,30.1,28.0,20.9,19.3,18.6,17.0,16.2,16.1。ESIMSm/z939[M+Na] +。Its NMR data are with document [ShenP, WangSL, LiuXK, YangCR, CaiB, YaoXS.AnewsteroidalsaponinfromDioscoreadeltoideaWallvar. the data orbiculata.Chin.Chem.Lett., 2002,13 (9): 851-854] are basically identical.
PariposideA, white solid, molecular formula C 39h 60o 14, CAS registration number 1439365-59-9. 1HNMR(C 5D 5N，500MHz)δ:6.49(1H,d,J＝8.5Hz),6.38(1H,brs),6.21(1H,d,J＝8.5Hz),1.75(3H,d,J＝6.3Hz),1.08(3H,d,J＝6.9Hz),0.93(3H,s),0.88(3H,s),0.66(3H,d,J＝5.4Hz)。 13CNMR(C 5D 5N，125MHz)δ:136.0,130.6,109.2,101.8,100.9,82.1,80.8,79.4,78.5,78.0,77.3,74.1,73.9,72.7,72.4,71.4,69.3,66.8,62.6,62.3,51.6,51.3,42.2,41.4,39.5,37.4,34.9,34.4,31.7,30.4,29.1,29.0,28.9,23.1,18.6,18.1,17.1,16.9,14.8。ESIMSm/z751[M-H] -。Its NMR data are with document [WuX, WangL, WangG-C, WangH, DaiY, YeW-C, LiY-L.NewsteroidalsaponinsandsterolglycosidesfromParispo lyphyllavar.yunnanensis.PlantaMed., 2012,78 (15): 1667-1675] data consistent in.
β-ecdyson, white solid, C 27h 44o 7, CAS registration number 5289-74-7. 1HNMR(CD 3OD,500MHz)δ:5.81(1H,d,J＝2.2Hz),3.96(1H,brd,J＝1.9Hz),3.84(1H,m),1.21(3H,s),1.20(3H,s),1.19(3H,s),0.97(3H,s),0.89(3H,s)。 13CNMR(CD 3OD,125MHz)δ:206.4,168.0,122.1,85.2,78.4,77.9,71.3,68.7,68.5,51.8,50.5,48.6,42.4,39.3,37.3,35.1,32.8,32.5,31.8,29.7,28.9,27.3,24.4,21.5,21.4,21.0,18.0。ESIMSm/z479[M-H] -。Its NMR data with document [Zhao Zhiyong, Gao Wenyuan, Huang Xian, Zhao Wanshun, Zhang Qiang. long connective Rhizoma Paridis chemical constitution study. Chinese herbal medicine, 2011,42 (10), 1917-1920] in data consistent.
Embodiment 3:
Rhizoma Paridis forrestii extract n-butanol extraction position (PFE-PT3) is to growth of tumour cell inhibitory action:
1. PFE-PT3 is carried out segmentation.
Getting weight is that the PFE-PT3 of 180g is through silica gel column chromatography chloroform-methanol mixed solvent gradient (10:1,5:1,3:1,1:1) the eluting section of drawing, obtains Fr.A (14g), Fr.B (101g), Fr.C (45g) and Fr.D (12g) 4 parts.Get Fr.B part 30g through C 18reversed-phase silica gel column chromatography (methanol-water, 10:90 → 100:0), obtains Fr.B 1(1.0g), Fr.B 2(0.5g), Fr.B 3(0.8g), Fr.B 4(4.6g), Fr.B 5(16.1g) and Fr.B 6(1.0g) 6 parts.
2. take a morsel sample from the large part of weight, utilizes column chromatography and half preparative high-performance liquid chromatographic technology, quick obtaining chemical composition.
Get Fr.B 3part 150mg, after crossing LH-20 gel filtration chromatography (methanol-eluted fractions), recycle silicon plastic column chromatography chloroform-methanol (5:1) eluting obtains β-ecdyson (39.0mg).
Get Fr.B 4part 130mg, by half preparative high-performance liquid chromatographic (Agilent 1200, ZorbaxSB-C 18chromatographic column, 9.4 × 250mm; Methanol-water, 72:28, flow velocity 2mL/min) purification obtains compounds methyl original weight building saponin I (30.0mg, retention time 25.313min) and the former Rhizoma Paridis saponin V of methyl (14.0mg, retention time 27.236min).
Get Fr.B 5part 120mg, by half preparative high-performance liquid chromatographic (Agilent 1200, ZorbaxSB-C 18chromatographic column, 9.4 × 250mm; Acetonitrile-water, 50:50, flow velocity 2mL/min) purification obtains PariposideA (4.5mg, retention time 12.788min), Rhizoma Paridis saponin II (1.4mg, retention time 14.634min), Rhizoma Paridis saponin III (14.4mg, retention time 18.070min), Rhizoma Paridis saponin I (12.7mg, retention time 21.019min) and Rhizoma Paridis saponin V (4.4mg, retention time 26.029min).
Get Fr.B 6part 132mg, half preparative high-performance liquid chromatographic (Agilent 1200, ZorbaxSB-C 18chromatographic column, 9.4 × 250mm; Acetonitrile-water, 40:60, flow velocity 2mL/min) purification obtains compound PGRR (4.1mg, retention time 18.421min) and Rhizoma Paridis saponin H (9.0mg, retention time 23.587min).
The present invention illustrates the main chemical compositions of Rhizoma Paridis forrestii active anticancer position PFE-PT3 first, and these compositions may be used for the quality control standard of working out PFE-PT3.
Rhizoma Paridis forrestii extract and treated each position are carried out cytotoxic activity test, the results are shown in Table 1.Result shows, n-butanol extraction position (PFE-PT3) has extremely significant inhibit activities to SMMC-7721 liver cancer cells, lung cancer cell A-549, MCF-7 Breast Cancer Cell and colon cancer SW480 cell, and its activity is better than positive control medicine cisplatin.
Table 1 Rhizoma Paridis forrestii extract n-butanol extraction position (PFE-PT3) is to growth of tumour cell inhibitory action
Embodiment 4:
The n-butanol extraction position (PFE-PT3) of Rhizoma Paridis forrestii extract, adds carboxymethyl starch sodium, starch is appropriate, and gelatinized corn starch is granulated, dry, granulate, adds Pulvis Talci in right amount, mixing, tabletting (every sheet 0.5g, be equivalent to Rhizoma Paridis forrestii rhizome 3g), each 2, every day 3 times.
Embodiment 5:
Prepare the medicine of Therapeutic cancer, mix by following percentage by weight: Rhizoma Paridis forrestii n-butanol extraction position PFE-PT3 accounts for 20-80%, dispersant 2-20%, disintegrating agent 3-5%, emulsifying agent 3-8%, binding agent 0.2-2%, wetting agent 0.5-10%, all the other are filler.Then process for preparing medicine obtains the anticarcinogen that effective ingredient is PFE-PT3 routinely.

Claims (10)

1. pharmaceutical composition, the Rhizoma Paridis forrestii n-butanol extraction position PFE-PT3 wherein containing treatment effective dose and pharmaceutically acceptable carrier, is characterized in that described PFE-PT3 is prepared by following method and obtains: Rhizoma Paridis forrestii dry rhizome, pulverize rear 95% soak with ethanol 7 days, filter, filtering residue continues to extract, altogether extract 4 times, merging filtrate, recycling design, obtains extractum, extractum water is made suspension, be extracted with ethyl acetate, reclaim ethyl acetate, obtain Ethyl acetate fraction; Mother solution after extraction into ethyl acetate, continuation n-butanol extraction, reclaims n-butyl alcohol, obtains n-butanol extraction position and PFE-PT3.
2. pharmaceutical composition, Rhizoma Paridis forrestii n-butanol extraction position PFE-PT3 wherein containing treatment effective dose and pharmaceutically acceptable carrier, it is characterized in that Rhizoma Paridis saponin I in described PFE-PT3, Rhizoma Paridis saponin II, Rhizoma Paridis saponin III, Rhizoma Paridis saponin V, Rhizoma Paridis saponin H, pennogenin-3-O-α-L-rhamnopyranosyl-(1 → 4)-[α-L-rhamnopyranosyl-(1 → 2)]-β-D-pyranglucoside (PGRR), methyl original weight building saponin I, the former Rhizoma Paridis saponin V of methyl, PariposideA and β-ecdyson, total content is 10-95% (weight).
3. pharmaceutical composition, Rhizoma Paridis forrestii n-butanol extraction position PFE-PT3 wherein containing treatment effective dose and pharmaceutically acceptable carrier, it is characterized in that Rhizoma Paridis saponin I in described PFE-PT3, Rhizoma Paridis saponin II, Rhizoma Paridis saponin III, Rhizoma Paridis saponin V, Rhizoma Paridis saponin H, pennogenin-3-O-α-L-rhamnopyranosyl-(1 → 4)-[α-L-rhamnopyranosyl-(1 → 2)]-β-D-pyranglucoside (PGRR), methyl original weight building saponin I, the former Rhizoma Paridis saponin V of methyl, PariposideA with β-ecdyson is separated from Rhizoma Paridis forrestii n-butanol extraction position PFE-PT3 to obtain, step is:
(1) PFE-PT3 is through silica gel column chromatography 10:1, and the chloroform-methanol mixed solvent gradient elution section of drawing of 5:1,3:1,1:1, obtains 4 parts such as Fr.A, Fr.B, Fr.C and Fr.D;
(2) Fr.B part is got through C 18reversed-phase silica gel column chromatography, the methanol-water of 10:90 → 100:0, obtains Fr.B 1, Fr.B 2, Fr.B 3, Fr.B 4, Fr.B 5and Fr.B 6deng 6 parts;
(3) Fr.B is got 3part, cross LH-20 gel filtration chromatography, after methanol-eluted fractions, the chloroform-methanol eluting of recycle silicon plastic column chromatography 5:1 obtains β-ecdyson;
(4) Fr.B is got 4part, purifies with half preparative high-performance liquid chromatographic and obtains methyl original weight building saponin I and the former Rhizoma Paridis saponin V of methyl;
(5) Fr.B is got 5part, purifies with half preparative high-performance liquid chromatographic and obtains PariposideA, Rhizoma Paridis saponin II, Rhizoma Paridis saponin III, Rhizoma Paridis saponin I and Rhizoma Paridis saponin V;
(6) Fr.B is got 6part, half preparative high-performance liquid chromatographic purification obtains compound PGRR and Rhizoma Paridis saponin H;
Wherein, half preparative high-performance liquid chromatographic described in (4) is with Agilent 1200 chromatograph of liquid, ZorbaxSB-C 18chromatographic column, chromatographic column size 9.4 × 250mm, eluant is methanol-water, ratio 72:28, flow velocity 2mL/min; (5) half preparative high-performance liquid chromatographic described in is with Agilent 1200 chromatograph of liquid, ZorbaxSB-C 18chromatographic column, chromatographic column size 9.4 × 250mm, eluant is acetonitrile-water, ratio 50:50, flow velocity 2mL/min; (6) half preparative high-performance liquid chromatographic described in is with Agilent 1200 chromatograph of liquid, ZorbaxSB-C 18chromatographic column, chromatographic column size 9.4 × 250mm, eluant is acetonitrile-water, ratio 40:60, flow velocity 2mL/min.
4. Rhizoma Paridis forrestii extract n-butanol extraction position PFE-PT3, it is characterized in that Rhizoma Paridis saponin I in described PFE-PT3, Rhizoma Paridis saponin II, Rhizoma Paridis saponin III, Rhizoma Paridis saponin V, Rhizoma Paridis saponin H, pennogenin-3-O-α-L-rhamnopyranosyl-(1 → 4)-[α-L-rhamnopyranosyl-(1 → 2)]-β-D-pyranglucoside (PGRR), methyl original weight building saponin I, the former Rhizoma Paridis saponin V of methyl, PariposideA and β-ecdyson, total content is 10-95% (weight), it is separated and obtains from Rhizoma Paridis forrestii n-butanol extraction position PFE-PT3, step is:
(1) PFE-PT3 is through silica gel column chromatography 10:1, and the chloroform-methanol mixed solvent gradient elution section of drawing of 5:1,3:1,1:1, obtains 4 parts such as Fr.A, Fr.B, Fr.C and Fr.D;
(2) Fr.B part is got through C 18reversed-phase silica gel column chromatography, the methanol-water of 10:90 → 100:0, obtains Fr.B 1, Fr.B 2, Fr.B 3, Fr.B 4, Fr.B 5and Fr.B 6deng 6 parts;
(3) Fr.B is got 3part, cross LH-20 gel filtration chromatography, after methanol-eluted fractions, the chloroform-methanol eluting of recycle silicon plastic column chromatography 5:1 obtains β-ecdyson;
(4) Fr.B is got 4part, purifies with half preparative high-performance liquid chromatographic and obtains methyl original weight building saponin I, and the former Rhizoma Paridis saponin V of methyl;
(5) Fr.B is got 5part, purifies with half preparative high-performance liquid chromatographic and obtains PariposideA, Rhizoma Paridis saponin II, Rhizoma Paridis saponin III, Rhizoma Paridis saponin I and Rhizoma Paridis saponin V;
(6) Fr.B is got 6part, half preparative high-performance liquid chromatographic purification obtains compound PGRR and Rhizoma Paridis saponin H;
Wherein, half preparative high-performance liquid chromatographic described in (4) is with Agilent 1200 chromatograph of liquid, ZorbaxSB-C 18chromatographic column, chromatographic column size 9.4 × 250mm, eluant is methanol-water, ratio 72:28, flow velocity 2mL/min; (5) half preparative high-performance liquid chromatographic described in is with Agilent 1200 chromatograph of liquid, ZorbaxSB-C 18chromatographic column, chromatographic column size 9.4 × 250mm, eluant is acetonitrile-water, ratio 50:50, flow velocity 2mL/min; (6) half preparative high-performance liquid chromatographic described in is with Agilent 1200 chromatograph of liquid, ZorbaxSB-C 18chromatographic column, chromatographic column size 9.4 × 250mm, eluant is acetonitrile-water, ratio 40:60, flow velocity 2mL/min.
5. the chemical composition isolation and identification method of a Rhizoma Paridis forrestii n-butanol extraction position PFE-PT3, it is characterized in that being separated from Rhizoma Paridis forrestii n-butanol extraction position PFE-PT3 obtaining Rhizoma Paridis saponin I, Rhizoma Paridis saponin II, Rhizoma Paridis saponin III, Rhizoma Paridis saponin V, Rhizoma Paridis saponin H, pennogenin-3-O-α-L-rhamnopyranosyl-(1 → 4)-[α-L-rhamnopyranosyl-(1 → 2)]-β-D-pyranglucoside (PGRR), methyl original weight building saponin I, methyl former Rhizoma Paridis saponin V, PariposideA and β-ecdyson, step is:
(1) PFE-PT3 is through silica gel column chromatography 10:1, and the chloroform-methanol mixed solvent gradient elution section of drawing of 5:1,3:1,1:1, obtains 4 parts such as Fr.A, Fr.B, Fr.C and Fr.D;
(2) Fr.B part is got through C 18reversed-phase silica gel column chromatography, the methanol-water of 10:90 → 100:0, obtains Fr.B 1, Fr.B 2, Fr.B 3, Fr.B 4, Fr.B 5and Fr.B 6deng 6 parts;
(3) Fr.B is got 3part, cross LH-20 gel filtration chromatography, after methanol-eluted fractions, the chloroform-methanol eluting of recycle silicon plastic column chromatography 5:1 obtains β-ecdyson;
(4) Fr.B is got 4part, purifies with half preparative high-performance liquid chromatographic and obtains methyl original weight building saponin I, and the former Rhizoma Paridis saponin V of methyl;
(5) Fr.B is got 5part, purifies with half preparative high-performance liquid chromatographic and obtains PariposideA, Rhizoma Paridis saponin II, Rhizoma Paridis saponin III, Rhizoma Paridis saponin I and Rhizoma Paridis saponin V;
(6) Fr.B is got 6part, half preparative high-performance liquid chromatographic purification obtains compound PGRR and Rhizoma Paridis saponin H;
Wherein, half preparative high-performance liquid chromatographic described in (4) is with Agilent 1200 chromatograph of liquid, ZorbaxSB-C 18chromatographic column, chromatographic column size 9.4 × 250mm, eluant is methanol-water, ratio 72:28, flow velocity 2mL/min; (5) half preparative high-performance liquid chromatographic described in is with Agilent 1200 chromatograph of liquid, ZorbaxSB-C 18chromatographic column, chromatographic column size 9.4 × 250mm, eluant is acetonitrile-water, ratio 50:50, flow velocity 2mL/min; (6) half preparative high-performance liquid chromatographic described in is with Agilent 1200 chromatograph of liquid, ZorbaxSB-C 18chromatographic column, chromatographic column size 9.4 × 250mm, eluant is acetonitrile-water, ratio 40:60, flow velocity 2mL/min.
6. the chemical composition isolation and identification method of a kind of Rhizoma Paridis forrestii n-butanol extraction position PFE-PT3 according to claim 5, it is characterized in that the method is separated from PFE-PT3 and obtain 10 compounds, by mass spectrum MS and NMR (Nuclear Magnetic Resonance) spectrum NMR, it is carried out to the determination of chemical constitution.
7. the chemical composition isolation and identification method of a kind of Rhizoma Paridis forrestii n-butanol extraction position PFE-PT3 according to claim 5, it is characterized in that the method obtains chemical composition Rhizoma Paridis saponin I from PFE-PT3, Rhizoma Paridis saponin II, Rhizoma Paridis saponin III, Rhizoma Paridis saponin V, Rhizoma Paridis saponin H, pennogenin-3-O-α-L-rhamnopyranosyl-(1 → 4)-[α-L-rhamnopyranosyl-(1 → 2)]-β-D-pyranglucoside (PGRR), methyl original weight building saponin I, the former Rhizoma Paridis saponin V of methyl, PariposideA and β-ecdyson, for setting up the quality control standard of PFE-PT3.
8. the application of Rhizoma Paridis forrestii n-butanol extraction position PFE-PT3 according to claim 4 in the medicine preparing treatment or prophylaxis of cancer disease.
9. the application of Rhizoma Paridis forrestii n-butanol extraction position PFE-PT3 according to claim 8 in the medicine preparing treatment or prophylaxis of cancer disease, the cancer described in it is hepatocarcinoma, pulmonary carcinoma, breast carcinoma, colon cancer.
10. prepare the method for the pharmaceutical composition of the Therapeutic cancer of claim 1 or 2 or 3, it is characterized in that mixing by following percentage by weight: Rhizoma Paridis forrestii n-butanol extraction position PFE-PT3 accounts for 20-80%, dispersant 2-20%, disintegrating agent 3-5%, emulsifying agent 3-8%, binding agent 0.2-2%, wetting agent 0.5-10%, all the other are filler.
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CN105726553A (en) * 2016-01-28 2016-07-06 中国科学院昆明植物研究所 Paris forrestii (Takht) H. Li. anti-cancer active component as well as pharmaceutical composition and application thereof
CN105902772A (en) * 2016-05-19 2016-08-31 宁波大昌药业有限公司 Process for purifying effective ingredient of paris polyphylla, pseudo-ginseng and folium isatidis extract
CN105902772B (en) * 2016-05-19 2021-06-29 宁波大昌药业有限公司 Process for purifying effective components of paris polyphylla, pseudo-ginseng and isatis leaf extract
CN106632197B (en) * 2016-12-15 2019-04-02 中国科学院昆明植物研究所 Single plumage fire cylinder tree anticancer activity position LA-D and its pharmaceutical composition is separated with its chemical component and identification method
CN106632197A (en) * 2016-12-15 2017-05-10 中国科学院昆明植物研究所 Anticancer active site LA-D of Leea crispa van Royen as well as medicinal composition thereof and chemical component separating and identifying method thereof
CN107422047A (en) * 2017-03-27 2017-12-01 西南民族大学 The discrimination method of Dulong Paris polyphylla
CN107446014B (en) * 2017-08-04 2019-08-02 中国科学院昆明植物研究所 Dulong Paris polyphylla ethanol extract and its application in pharmacy separate and identification method with its chemical component
CN107446014A (en) * 2017-08-04 2017-12-08 中国科学院昆明植物研究所 The Dulong Paris polyphylla ethanol extract and its application in pharmacy is separated with its chemical composition and authentication method
CN108164579A (en) * 2018-03-23 2018-06-15 中国食品药品检定研究院 A kind of method of aerial part extraction separation chonglou saponin H from Paris polyphylla
CN108853308A (en) * 2018-07-06 2018-11-23 西安医学院 A kind of Chinese paris rhizome total saponin-semen momordicae pharmaceutical composition and preparation method
CN108853308B (en) * 2018-07-06 2021-06-15 西安医学院 Paris polyphylla total saponin-semen momordicae medicinal composition and preparation method thereof
CN108822182A (en) * 2018-07-23 2018-11-16 广西壮族自治区药用植物园 The preparation method of chonglou saponin H and its application in treatment gastroenteritis
CN114668773A (en) * 2022-04-08 2022-06-28 山东中医药大学 Application of rhizoma paridis extract in resisting Climiya Congo hemorrhagic fever virus
CN114668773B (en) * 2022-04-08 2023-10-03 山东中医药大学 Application of paris polyphylla extract in resisting Crimedes congo hemorrhagic fever virus

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