CN105218615B - A kind of natural noval chemical compound and its preparation and application - Google Patents
A kind of natural noval chemical compound and its preparation and application Download PDFInfo
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- CN105218615B CN105218615B CN201510614197.2A CN201510614197A CN105218615B CN 105218615 B CN105218615 B CN 105218615B CN 201510614197 A CN201510614197 A CN 201510614197A CN 105218615 B CN105218615 B CN 105218615B
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Abstract
The invention discloses a kind of natural noval chemical compound and its preparation and application.The compound structure is novel, anti-tumor activity is strong, it is isolated from the root Radix seu Cortex Heteropanaciss of dolichos falcatus Klein (Dolichos falcata Klein), also disclose its preparation method, alcohol extraction Radix seu Cortex Heteropanaciss coarse powder, concentrating under reduced pressure, Jing silica gel column chromatographies, with chloroform methanol gradient elution, separating-purifying obtains the compound, the noval chemical compound white in appearance powder, for triterpene saponin, molecular formula is C36H56O10, it is named as：Radix seu Cortex Heteropanaciss saponin C.
Description
Technical field
The invention belongs to pharmaceutical technology field, and in particular to a kind of natural new compound structure and preparation method and application.
Background technology
Root of the Radix seu Cortex Heteropanaciss for pulse family Seem Lablab Album platymiscium dolichos falcatus Klein (Dolichos falcataKlein), be commonly called as in fiber crops fiber crops,
Numb three sections, bean leaf Herba Gynurae Divaricatae, it is medicinal on Yunnan, Guizhou and other places, the effects such as with expelling wind and activating blood circulation, hemostasis and pain-relieving.By document
Consult Radix seu Cortex Heteropanaciss chemical composition and pharmacology activity research is less, Pu Hunan Chongqing et al. carried out the research of chemical composition to which, found
Wherein main saponin constituent is Radix seu Cortex Heteropanaciss saponin A [Pu Hunan Chongqing etc., the triterpene saponin component (1) of Radix seu Cortex Heteropanaciss, Yunnan plant research
1984,6 (3) 321-324].70～eighties of 20th century Guiyang Medical College, Huang Houpin et al. carried out roughly to Radix seu Cortex Heteropanaciss total saponins
Antitumaous effect research.The report of the isolated Radix seu Cortex Heteropanaciss saponin C from Radix seu Cortex Heteropanaciss is there is presently no, in the online of chemical abstractss
Version data base's Scifinder data look into new and literature query does not have the report of Radix seu Cortex Heteropanaciss saponin C yet, is new native compound, arrives
Also the report furtherd investigate by the monomer component activity of Radix seu Cortex Heteropanaciss saponin was not carried out so far, especially without Radix seu Cortex Heteropanaciss
The relevant report of saponin monomer composition anti-tumor activity.We carry out comprehensive chemical constitution study to Radix seu Cortex Heteropanaciss, first from big
Isolated natural noval chemical compound Radix seu Cortex Heteropanaciss saponin C in anaesthetic is big to the natural noval chemical compound of the single saponin constituent of Radix seu Cortex Heteropanaciss first
Anaesthetic saponin C carries out anti-tumor activity and is studied.
The content of the invention
Blank for prior art, the present invention discloses new active component Radix seu Cortex Heteropanaciss saponin C, and it can be flat from natural plants sickle fruit
Obtain in the root of bean, its structure is novel, anti-tumor activity is strong, also discloses its preparation method.
Technical scheme is as follows：
1. natural noval chemical compound Radix seu Cortex Heteropanaciss saponin C or its pharmaceutically acceptable salt shown in formula I：
2. the preparation method of the natural noval chemical compound Radix seu Cortex Heteropanaciss saponin C described in technical scheme 1, the method include：Alcohol extraction is big
Anaesthetic coarse powder, concentrating under reduced pressure, Jing silica gel column chromatographies, with chloroform-methanol gradient elution, separating-purifying is obtained described in technical scheme 1
Natural noval chemical compound Radix seu Cortex Heteropanaciss saponin C.
3. shown in the formula I described in technical scheme 1, natural noval chemical compound Radix seu Cortex Heteropanaciss saponin C or its pharmaceutically acceptable salt exist
Prepare the application in antitumor drug.
4. the application described in technical scheme 3, the tumor are pulmonary carcinoma or hepatocarcinoma.
5. it is a kind of prevention and/or treat tumor medicine, its active component be technical scheme 1 described in formula I shown in it is natural
Noval chemical compound Radix seu Cortex Heteropanaciss saponin C or its pharmaceutically acceptable salt.
6. prevent and/or treat the medicine of tumor according to technical scheme 5, described medicine be injection, injectable powder,
Tablet, capsule, granule or drop pill.
7. prevent and/or treat the medicine of tumor according to technical scheme 5 or 6, the tumor is pulmonary carcinoma or hepatocarcinoma.
Compared with prior art, beneficial effects of the present invention：
The isolated first Radix seu Cortex Heteropanaciss saponin C with novel chemical constitution of the present invention, it is a kind of natural new chemical combination
Thing, Radix seu Cortex Heteropanaciss saponin C have stronger active anticancer, can significantly inhibit the growth of tumor, while the thymus to tumor-bearing mice
Index and spleen index have no significant effect.
Description of the drawings
Fig. 1 is Radix seu Cortex Heteropanaciss saponin C plane structure charts.
Fig. 2 is Radix seu Cortex Heteropanaciss saponin C relative configuration figures.
Specific embodiment
The present invention is described in further detail with reference to specific embodiment.Test material used by following embodiment
Can buy from commercial channel in addition to the compounds of this invention for preparing.
Embodiment 1：Composition is separated
Radix seu Cortex Heteropanaciss 10Kg, is extracted 3 times with 70% alcohol heat reflux after crushing, the extractum 1250g of concentrating under reduced pressure, Jing silicagel columns
Chromatography, with chloroform-methanol gradient elution, gradient is chloroform：The volume ratio of methanol is 50：1,30：1,20：1,10：1,5：1,3：
1,1：1, Jing TLC detects that same section is combined, and is divided into 6 parts, respectively numbering be Fr.1, Fr.2, Fr.3,
Fr.4、Fr.5、Fr.6；Wherein Fr.3 Jing silica gel column chromatographies, dextran gel column chromatography separating-purifying obtain the chemical combination of 500mg
Thing, is named as Radix seu Cortex Heteropanaciss saponin C.
Embodiment 2：Radix seu Cortex Heteropanaciss saponin C-structure is identified
Radix seu Cortex Heteropanaciss saponin C is white powder, is dissolved in methanol, is to determine that its chemical constitution has done as follows to Radix seu Cortex Heteropanaciss saponin C
Collection of illustrative plates：(1) spectrum has done optical rotational activity spectrum, ultraviolet spectra and infrared spectrum, and the one-dimensional spectrum of (2) nuclear magnetic resonance, NMR is done1H、13C and DEPT
Spectrum, (3) Two-dimensional NMR Map be HMBC, HSQC and1H-1H COSY are composed, (4) NOE experiments.
Below total qualification process is described in detail：Composed according to one-dimensional nuclear-magnetism1H、13C NMR and DEPT are composed, just
Step is judged as a triterpene saponin, by literature survey, Pu Hunan Chongqing et al. once isolated triterpene saponin Fructus Cannabiss from the plant
Medicine glycoside A (DolirosideA), both nuclear magnetic datas have very big similarity.According to the quasi-molecular ion that ESI+-MS is given
Peak 671 ([M+Na]+), HRESIMS ([M+Na]+, m/z is 671.3769) and NMR data obtains its molecular formula for C36H56O10, insatiable hunger
It is 9 with degree.In infrared spectrum, 3423cm-1For hydroxyl absorption peak, 2945,2928cm-1For methyl, methylene absworption peak,
1712cm-1For carbonyl absorption peak.In being composed by further confirming that for two-dimensional nucleus magnetic spectrum data, especially HMBC, H2-1 (δ 2.30,
2.25,2H, ABd, J=-17.0Hz) and H-3 (δ 4.58,1H, s) while related to C-2 (δ 213.3)；And H2-23 (δ
3.53,3.39,2H, ABd, J=-9.3Hz) with C-3 (δ 83.8), C-5 (δ 47.7), C24 (δ 13.7) be related, H-3, H-5 (δ
1.95,1H, overlapped), and H3-24 (δ 0.65,3H, it is s) related to C-23 (δ 64.1).These conclusions are shown with infrared spectrum
Functional group be consistent.By further HSQC, HMBC and1H-1H COSY spectrum analysis (table 1), and similar compound NMR
Comparing, the planar structure for finally determining the compound are Fig. 1.
To determine the relative configuration of Radix seu Cortex Heteropanaciss saponin C, we have done NOE experiments, H-3 and H-1 α, H- in ROESY spectrograms
5, H-23a is related, it was demonstrated that H-3 is α configurations；H-23a is related to H-3, while H3-24 is related to H3-25, it was demonstrated that hydroxyl is substituted in
C-23 positions rather than C-24 positions.By comprehensive REOSY spectrum analysis (data such as table 1), the configuration of other substituent groups and Fructus Cannabiss
Medicine glycoside A configurations are completely the same such as Fig. 2.Compound specific rotation value [α] 25.5D+42.43 (c 0.31, MeOH), it is similar with other
Thing is all on the occasion of and the triterpene saponin of the type is all oleanane type rather than its enantiomer, it is contemplated that in being same plant
Relationship type on the product for obtaining simultaneously and such triterpene source of students, finally determines Radix seu Cortex Heteropanaciss with reference to spectrum data and literature survey
The chemical constitution of saponin C is as shown in formula I.The compound structure is unique, the functional group and known compound on C-2 positions and C-4 positions
There is bigger difference, Jing scifinder site searches are defined as noval chemical compound, are named as Radix seu Cortex Heteropanaciss saponin C.
Compound structure data are as follows：
Molecular formula is C36H56O10, molecular weight is 648；[α]25.5D+42.43(c 0.31,MeOH)；UV(MeOH)λmax
(logε):203(3.13)nm；IR(KBr)νmax 3423,2945,2928,1712,1631,1462,1394,1279,1261,
1164,1077,1052,644cm–1；positive ESIMS:m/z 671[M+Na]+；positive HRESIMS[M+Na]+m/
z 671.3769(calcd for C36H56O10Na[M+Na]+,671.3766)；1H、13The nuclear magnetic datas such as C such as table 1.
1. Radix seu Cortex Heteropanaciss saponin C nuclear magnetic data tables of table (in MeOD, δ in ppm (Jin Hz).
The experimentation of the anti-tumor activity of 2 the compounds of this invention of embodiment
(1) tumor-inhibiting actions of the Radix seu Cortex Heteropanaciss saponin C to Lewis lung cancer mice
1. material
1.1 tumor strains
Lewis lung cancer is purchased from China Medicine University's tumor experiment room.
1.2 animal
C57BL/6 (C57BL/6J Mouse) mice, 50, male, 18～22g of body weight have purchased from Kunming Chu business's science and technology
Limit company, animal quality certification number SCXK (Hunan) K2012-0002.
1.3 medicine
Radix seu Cortex Heteropanaciss saponin C is prepared by embodiment 1 by Yunnan Plant Pharmaceutical Industry Co., Ltd. academy laboratory；Cyclophosphamide
(CY) purchased from SHANXI POWERDONE PHARMACEUTICAL.,LTD, lot number：20141102.Radix seu Cortex Heteropanaciss saponin C according to mice preliminary result, if
High, medium and low three dosage：50mg/kg, 100mg/kg, 200mg/kg.
1.4 instrument
Inverted microscope, Chongqing optical instrument factory；Superclean bench, Suzhou Decontamination Equipment Plant；LXJ2I type centrifuges, on
Hai Yiyongfenxiyiqichang；Three use electric heating constant-temperature water-bath tank, Beijing Chang'an scientific instrument factory；Vortex mixer, Zhejiang Le Cheng are electric
Device factory.
2. experimental technique
After selecting inoculation Lewis lung cancer 14d, the good mice with tumor of ordinary circumstance takes off neck and puts to death, aseptic to strip tumor group
Knit, be homogenized, with normal saline dilution into 1 × 107/ ml, living cell counting number>95%.50 C57BL/6 mices are taken, per only little
The right axil subcutaneous vaccination 0.2mL tumor cell suspensions of Mus.Then mice is randomly divided into into 5 groups, 10 per group, respectively：Lotus knurl mould
Type group, positive group, high, medium and low three dosage groups of Radix seu Cortex Heteropanaciss saponin C.Mice is administered each group as follows, once a day, continuously
12 days：Positive group intraperitoneal injection of cyclophosphamide 30mg/kg；High, medium and low three dosage groups of Radix seu Cortex Heteropanaciss saponin C distinguish lumbar injection
The Radix seu Cortex Heteropanaciss saponin C of 200mg/kg, 100mg/kg, 50mg/kg；The normal saline of the capacity such as lotus knurl model group lumbar injection,
0.1mL/10g.Put to death mice within the 13rd day after administration, strip tumor body and weigh, calculate tumour inhibiting rate；And spleen and thymus are won, weigh,
Calculate spleen index and thymus index.Tumour inhibiting rate=(the average knurl weight of the average knurl weight ﹣ medication group of matched group) average tumor of/matched group ×
100%；Spleen index (thymus index)=spleen weight (chest gland weight)/body weight (unit：mg/g).
3. result
From table 2, the average knurl weight of model group is more than 1g, represents modeling success.Positive drug CY can significantly inhibit mice
The growth of Lewis lung cancer, inhibitory rate 81.8%.Radix seu Cortex Heteropanaciss saponin C is high, middle dose group has substantially to Mice Bearing Lewis Lung Cancer
Inhibitory action, tumour inhibiting rate be respectively 57.6% and 50.8%, comparing with model group has significant difference (P<0.01).Radix seu Cortex Heteropanaciss
Saponin C low dose groups have certain inhibitory action to Mice Bearing Lewis Lung Cancer, and tumour inhibiting rate is 27.3%, compares nothing with model group
Significant difference (P>0.05).CY can significantly inhibit the thymus index and spleen index (P of tumor-bearing mice while tumor suppression<
0.01), and tri- dosage groups of Radix seu Cortex Heteropanaciss saponin C are had no significant effect to the thymus index and spleen index of tumor-bearing mice.
Inhibitory action of the 2. Radix seu Cortex Heteropanaciss saponin C of table to Mice Bearing Lewis Lung Cancer transplanted tumor
*P<0.05, * * P<0.01, compare with model group
(2) tumor-inhibiting actions of the Radix seu Cortex Heteropanaciss saponin C to Heps liver cancer mouses
1. material
1.1 tumor strains
Rat liver cancer solid type (Heps), purchased from China Medicine University's tumor experiment room.
1.2 animal
ICR mices, 50, male and female half and half, 18～22g of body weight, purchased from Kunming Chu Shang Science and Technology Ltd.s, the animal quality certification
Number SCXK (Hunan) K2012-0002.
1.3 medicine
Radix seu Cortex Heteropanaciss saponin C is prepared by embodiment 1 by Yunnan Plant Pharmaceutical Industry Co., Ltd. academy laboratory；Cyclophosphamide
(CY) purchased from SHANXI POWERDONE PHARMACEUTICAL.,LTD, lot number：20141102.Radix seu Cortex Heteropanaciss saponin C according to mice preliminary result, if
High, medium and low three dosage：50mg/kg, 100mg/kg, 200mg/kg.
1.4 instrument
Inverted microscope, Chongqing optical instrument factory；Superclean bench, Suzhou Decontamination Equipment Plant；LXJ2I type centrifuges, on
Hai Yiyongfenxiyiqichang；Three use electric heating constant-temperature water-bath tank, Beijing Chang'an scientific instrument factory；Vortex mixer, Zhejiang Le Cheng are electric
Device factory.
2. experimental technique
Aseptic aspiration passes on the ascites of the tumor-bearing mice of rear 8d, is diluted with physiological saline solution, adjustment cell concentration to 5.0
×107/ ml, it is subcutaneous to be inoculated in mice right fore, every 0.2ml.Then mice is randomly divided into into 5 groups, 10 per group, respectively
For：Lotus knurl model group, positive group, high, medium and low three dosage groups of Radix seu Cortex Heteropanaciss saponin C.Mice is administered each group as follows, often
It 1 time, continuous 12 days：Positive group intraperitoneal injection of cyclophosphamide 30mg/kg；High, medium and low three dosage components of Radix seu Cortex Heteropanaciss saponin C
The Radix seu Cortex Heteropanaciss saponin C of other lumbar injection 200mg/kg, 100mg/kg, 50mg/kg；The life of the capacity such as lotus knurl model group lumbar injection
Reason saline, 0.1mL/10g.Put to death mice within the 13rd day after administration, strip tumor body and weigh, calculate tumour inhibiting rate；And win spleen and breast
Gland, weighs, and calculates spleen index and thymus index.Tumour inhibiting rate=(the average knurl weight of the average knurl weight ﹣ medication group of matched group)/matched group is put down
Equal tumor × 100%；Spleen index (thymus index)=spleen weight (chest gland weight)/body weight (unit：mg/g).
3. result
From table 3, the average knurl weight of model group is more than 1g, represents modeling success.Positive drug CY can significantly inhibit mice
The growth of Heps hepatocarcinoma, inhibitory rate 69.0%.There is to mice Heps Radix seu Cortex Heteropanaciss saponin C high dose groups significantly suppression to make
With, its inhibitory rate 31.7%, comparing with model group has significant difference (P<0.01)；In Radix seu Cortex Heteropanaciss saponin C, low dose group pair
Mice Heps have certain inhibitory action, and tumour inhibiting rate is respectively 19.0% and 9.5%, and it is poor to compare with model group that there are no significant
Different (P>0.05).CY can significantly inhibit the thymus index of tumor-bearing mice while tumor suppression, and Radix seu Cortex Heteropanaciss saponin C high dose group energy
Significantly improve the thymus index of tumor-bearing mice, in, low dose group had no significant effect to the thymus index and spleen index of tumor-bearing mice.
Inhibitory action of the 3 Radix seu Cortex Heteropanaciss saponin C of table to Transplanted murine tumors Heps
*P<0.05, * * P<0.01, compare with model group
Research shows：The tumour inhibiting rate of Radix seu Cortex Heteropanaciss saponin C of the present invention is high without cyclophosphamide, but cyclophosphamide is in tumor suppression
While the thymus index and spleen index of mice can be significantly impacted, and breast of tri- dosage groups of Radix seu Cortex Heteropanaciss saponin C to tumor-bearing mice
Gland index and spleen index have no significant effect, and have stronger active anticancer.
Claims (6)
1. the saponin of native compound Radix seu Cortex Heteropanaciss shown in formula I C or its pharmaceutically acceptable salt：
2. the preparation method of the native compound Radix seu Cortex Heteropanaciss saponin C described in claim 1, it is characterised in that the method includes：Alcohol
Carry Radix seu Cortex Heteropanaciss coarse powder, concentrating under reduced pressure, Jing silica gel column chromatographies, with chloroform-methanol gradient elution, separating-purifying obtains claim 1
Described native compound Radix seu Cortex Heteropanaciss saponin C.
3. native compound Radix seu Cortex Heteropanaciss saponin C shown in the formula I described in claim 1 or its pharmaceutically acceptable salt are anti-in preparation
Application in tumour medicine, the tumor are pulmonary carcinoma or hepatocarcinoma.
4. it is a kind of prevention and/or treat tumor medicine, its active component be claim 1 described in formula I shown in natural compounds
Thing Radix seu Cortex Heteropanaciss saponin C or its pharmaceutically acceptable salt.
5. prevent and/or treat the medicine of tumor according to claim 4, it is characterised in that：Described medicine be injection,
Injectable powder, tablet, capsule, granule or drop pill.
6. according to claim 4 or 5 prevent and/or treat tumor medicine, it is characterised in that：The tumor be pulmonary carcinoma or
Hepatocarcinoma.
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| New Oleanene Triterpenoid Saponins from Madhuca longifolia;Kazuko Yoshikawa et al.;《J. Nat. Prod.》;20001028;第63卷;第1679-1681页 * |
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