CN116333029B - Tea seed saponin compound and application thereof - Google Patents
Tea seed saponin compound and application thereof Download PDFInfo
- Publication number
- CN116333029B CN116333029B CN202310313794.6A CN202310313794A CN116333029B CN 116333029 B CN116333029 B CN 116333029B CN 202310313794 A CN202310313794 A CN 202310313794A CN 116333029 B CN116333029 B CN 116333029B
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- CN
- China
- Prior art keywords
- compound
- column chromatography
- saponin
- camellia seed
- macroporous resin
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
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- 229930185549 teaseedsaponin Natural products 0.000 title description 8
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- 150000007949 saponins Chemical class 0.000 claims abstract description 55
- 235000018597 common camellia Nutrition 0.000 claims abstract description 36
- -1 saponin compound Chemical class 0.000 claims abstract description 26
- 239000011347 resin Substances 0.000 claims abstract description 18
- 229920005989 resin Polymers 0.000 claims abstract description 18
- 238000004440 column chromatography Methods 0.000 claims abstract description 12
- 238000010898 silica gel chromatography Methods 0.000 claims abstract description 9
- 241001122767 Theaceae Species 0.000 claims description 36
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- 235000012054 meals Nutrition 0.000 claims description 14
- 238000010828 elution Methods 0.000 claims description 13
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims description 11
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Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07J—STEROIDS
- C07J63/00—Steroids in which the cyclopenta(a)hydrophenanthrene skeleton has been modified by expansion of only one ring by one or two atoms
- C07J63/008—Expansion of ring D by one atom, e.g. D homo steroids
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P35/00—Antineoplastic agents
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P35/00—Antineoplastic agents
- A61P35/02—Antineoplastic agents specific for leukemia
-
- Y—GENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
- Y02—TECHNOLOGIES OR APPLICATIONS FOR MITIGATION OR ADAPTATION AGAINST CLIMATE CHANGE
- Y02A—TECHNOLOGIES FOR ADAPTATION TO CLIMATE CHANGE
- Y02A50/00—TECHNOLOGIES FOR ADAPTATION TO CLIMATE CHANGE in human health protection, e.g. against extreme weather
- Y02A50/30—Against vector-borne diseases, e.g. mosquito-borne, fly-borne, tick-borne or waterborne diseases whose impact is exacerbated by climate change
Landscapes
- Health & Medical Sciences (AREA)
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- General Health & Medical Sciences (AREA)
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Abstract
The invention relates to the technical field of compound application, in particular to a camellia seed saponin compound and application thereof, wherein 7 saponin monomer compounds are separated from camellia seed dreg ethanol extract by utilizing modern separation technologies such as macroporous resin column chromatography, silica gel column chromatography, reversed-phase C-18 column chromatography, high-performance liquid chromatography and the like, and the analysis of the structure-activity relationship of the compounds shows that the hydroxy connected at the C-16 position of sapogenin plays a vital role in anticancer activity of the camellia seed saponin compound.
Description
Technical Field
The invention relates to the technical field of compound application, in particular to a camellia seed saponin compound and application thereof.
Background
China is the country with the largest oil tea seed yield in the world. The tea seed meal is a byproduct obtained by extracting tea oil from tea seeds by pressing, and contains various active ingredients such as tea saponin, tea polyphenol, tea polysaccharide, flavone, protein and the like. Because of lack of enough knowledge of the value of tea seed meal in the past, a large amount of tea seed meal is discarded, so that resource waste is caused. Through literature research, tea seed meal contains about 15% of tea saponins, and researches prove that the saponins have various biological activities such as anticancer, anti-inflammatory, antibacterial, hemolysis, antioxidant, blood fat reducing and the like. At present, research on the bioactivity of tea saponin at home and abroad is mostly remained on the saponin mixture level, the action mechanism and the structure-activity relationship are not clear, and the development and the utilization of tea saponin are limited. Therefore, the tea saponin monomer is further separated and purified, and the structure and biological activity relationship of the tea saponin monomer are researched, so that the tea saponin monomer has great significance and value in the fields of agriculture and medicine.
Tea saponin (teasaponin) is also called Tea saponin, which is a common name of plant saponin of camellia in Theaceae, and is oleanane (oleanane type) pentacyclic triterpene saponin mixture. Theasaponin is a good natural surfactant and bioactive substance, and is widely used in roots, stems, leaves, flowers, fruits and seeds of plants of the genus camellia of the family camellia, especially in the most abundant seeds. The tea saponin comprises sapogenin, sugar body (mostly oligosaccharide) and organic acid. Sapogenins are typically triterpenes; the sugar body is formed by connecting different monosaccharides, and mainly comprises glucuronic acid, arabinose, xylose, glucose, galactose, rhamnose and the like; the organic acid mainly comprises angelic acid, acetic acid, tiglic acid, hexenoic acid, cinnamic acid, 2-methyl butyric acid and the like, and can be condensed with hydroxyl groups on aglycone to form esters.
The tea saponin has strong foamability, emulsifying property, dispersibility, wettability, etc., and has active bioactivity such as anticancer, antiinflammatory, antibacterial, hemolysis, antioxidant, blood pressure lowering, weight reducing, nerve stimulating or neuroprotection, fish toxicity, and insecticidal activity. In the last decades, there has been a great progress in the study of phytochemical properties and biological activities of the saponin and sapogenin components of camellia oleifera. However, since the polarities of the tea saponins are very similar and the isomers are more, it is difficult to separate and purify enough tea saponin monomers, and at present, research on the biological activity of the tea saponins at home and abroad is mostly remained on the level of the saponin mixture, so the action mechanism and the structure-activity relationship are not clear. The structure-activity relationship refers to the relationship between the structure and the bioactivity of tea saponin, and in recent years, students at home and abroad have studied the structure-activity relationship of tea saponin in camellia plants, and found that the bioactivity of tea saponin has a great relationship with substituent groups of certain connecting sites on sapogenin parent nucleus, but the specific relationship is not clear, and needs to be further studied. The separation and purification of the new tea saponin monomer compound is helpful for researching the specific relationship between the chemical structure and the biological activity of the tea saponin monomer compound, and provides a molecular level basis for exploring the action mechanism of the tea saponin.
In view of the above drawbacks, the present inventors have finally achieved the present invention through long-time studies and practices.
Disclosure of Invention
The invention aims to solve the problem of how to further separate and purify tea saponin monomers and define the action mechanism and structure-activity relationship of the tea saponin monomers, and provides tea seed saponin compounds and application thereof.
In order to achieve the aim, the invention discloses a camellia seed saponin compound, which has the following structure:
Wherein R 3 is hydroxy, R 1 is organic acid or unconnected substituent, R 2 is organic acid, and R 4 is sugar chain.
The compound has the structure of
The compound has the structure of
The invention also discloses a preparation method of the camellia seed saponin compound, which comprises the following steps:
s1, separating and purifying crude oil tea seed meal extract by macroporous resin column chromatography to obtain an elution component;
s2, eluting the elution component obtained by macroporous resin column chromatography in the step S1 by normal phase silica gel column chromatography, then eluting by reverse phase silica gel column chromatography, collecting the elution component, and further separating and purifying by high-liquid chromatography to obtain the camellia seed saponin compound.
In the step S1, the macroporous resin column chromatography is to dissolve crude oil tea seed extract with 75% ethanol, mix with AB-8 macroporous resin with equal mass, wet column packing with activated AB-8 macroporous resin, dry column packing, collecting 50:50 eluate, concentrating under reduced pressure to paste for subsequent treatment, and collecting 50% eluate with larger polarity saponins.
The specific process of the step S2 is as follows: eluting the eluted components obtained by macroporous resin column chromatography by using ethyl acetate-methanol volume ratio of 6:1 to 0:1 as concentration gradient, combining components with the same Rf value, selecting the component No. 20 presenting purple spots, evaporating to dryness, performing ODS reversed-phase silica gel column chromatography, eluting by using methanol-water volume ratio of 30:70-100:0, collecting the eluted components of 40:60-50:50, and further separating and purifying by using high performance liquid phase to obtain the camellia seed saponin compound.
The invention also discloses application of the camellia seed saponin compound in preparing anticancer drugs.
Compared with the prior art, the invention has the beneficial effects that: according to the invention, 7 novel saponin monomer compounds are separated and purified from camellia seed meal, and named oleiferasaponin G 1 (compound 1), oleiferasaponin G 2 (compound 2), oleiferasaponin G 3 (compound 3), oleiferasaponin G 4 (compound 4), oleiferasaponin G 5 (compound 5), oleiferasaponin G 6 (compound 6) and oleiferasaponin G 7 (compound 7), and the antitumor activity of the camellia seed saponin compounds on human colon cancer cells (HCT-116), human leukemia cells (HL 60) and human liver cancer cells (HepG 2) is measured, wherein compounds 1-5 do not show obvious inhibition effects on 3 tumor cells; compound 6 and compound 7 have very pronounced inhibitory effects, IC 50 value for compound 6: IC 50 value for Compound 7, 1.200. Mu.M (HCT-116), 3.515. Mu.M (HL-60), 2.518. Mu.M (HepG 2): 1.208. Mu.M (HCT-116), 2.938. Mu.M (HL-60), 2.711. Mu.M (HepG 2); the total saponins showed weak inhibitory activity against 3 tumor cells.
Drawings
FIG. 1 shows a TLC analysis of AB-8 macroporous resin separated crude oil tea seed meal extract;
FIG. 2 shows TLC analysis of component B by forward silica gel column separation;
FIG. 3 is a TLC analysis of reverse phase silica gel column separation of the alpha component;
FIG. 4 is a flow chart for separating and purifying sasanqua seed saponin monomers;
FIGS. 5 (a) -5 (f) are graphs showing the inhibition fit of compounds 4-7, oleiferasaponin D 2、D3 to HCT-116;
FIG. 5 (g) is a graph showing the inhibition fit of total saponins to HCT-116;
FIGS. 6 (a) -6 (d) are graphs of inhibition fits of compounds 6, 7, oleiferasaponin D 2、D3 to HL-60;
FIG. 6 (e) is a graph of the inhibition fit of total saponins to HL-60;
FIGS. 7 (a) -7 (d) are graphs showing the inhibition fit of compounds 6, 7, oleiferasaponin D 2、D3 to HepG 2;
FIG. 7 (e) is a graph showing the inhibition fit of total saponins to HepG 2.
Detailed Description
The above and further technical features and advantages of the present invention are described in more detail below with reference to the accompanying drawings.
1. Separation, purification and structural identification of camellia seed saponin
1. Qualitative detection of camellia seed saponin
Sulfuric acid-ethanol color reaction: the sample solution is sucked by a capillary tube and is spotted on one end of the thin layer plate, and the end with the sample is placed in a spreading cylinder with a spreading agent in parallel downwards. The components in the sample travel along the plate with the developing agent, and eventually move different distances on the plate due to the polarity difference between the components, so as to obtain mutually separated component spots. After the expansion, the thin-layer plate is immersed in sulfuric acid-ethanol-vanillin solution, then heated and dried, and the color change is observed, and if the purple spots appear, the triterpenoid saponin is indicated.
2. AB-8 macroporous resin column chromatography separation of oil tea seed meal ethanol extract
Dissolving 1kg of camellia seed meal ethanol extract with 75% ethanol, mixing with AB-8 macroporous resin and the like, loading into a column by using activated AB-8 macroporous resin by a wet method, and loading into a sample by a dry method. The eluent is ethanol: the water is eluted in a gradient way, the volume ratio of EtOH-H 2 O is respectively 30:70, 50:50, 70:30 and 90:10 are used as concentration gradients for elution, and the corresponding elution volumes are respectively 2.5BV, 4BV and 13BV. Detecting by thin layer chromatography combined with sulfuric acid-ethanol color reaction, mixing eluents with the same Rf value, and concentrating under reduced pressure by a rotary evaporator to obtain A, B, C components. The component A is total flavonoid glycoside, the component B is a mixture of flavonoid glycoside and saponin, and the component C is total saponin. Wherein the component B has 70g and is further separated and purified.
3. Separating B component saponin by normal phase silica gel column chromatography
The B component obtained in the previous experiment is further separated and purified by a silica gel column. Adding methanol into the component B until the component B is completely dissolved, mixing with 200-300 mesh silica gel, loading into a column by using 200-300 mesh silica gel dry method, and loading into a sample by using dry method. The eluent is ethyl acetate: methanol, elution was performed as a concentration gradient with a volume ratio of EtOAc-MeOH from 6:1 to 0:1. Detecting by thin layer chromatography combined with sulfuric acid-ethanol color reaction, combining components with the same Rf value, and selecting alpha component presenting purple spots for further separation and purification.
4. Reversed-phase silica gel column chromatography for separating alpha-component saponin
And separating and purifying the alpha component obtained by normal phase silica gel column separation by reverse phase silica gel column. Dissolving the alpha component with methanol, mixing with dry reverse phase silica gel, loading into column with dry reverse phase silica gel, and loading into sample with wet method. Methanol is used as the raw material: the water is used as eluent for gradient elution, and the volume ratio of the MeOH-H 2 O with the gradient concentration is 30:70-35:65-40:60-45:55-50:50-55:45-60:40-65:35-70:30-5:25-80:20-100:0. The components of similar composition were combined according to thin layer chromatography in combination with sulfuric acid-ethanol color reaction to give 2.5g of beta component.
5. Pre-HPLC separation and purification of beta-component saponin
Dissolving beta component obtained by reverse silica gel column separation with chromatographic methanol, and separating and purifying by Prep-HPLC liquid phase gradient elution. And collecting corresponding mobile phases according to an ultraviolet absorption chromatogram, merging the mobile phases with the same components through HPLC liquid phase analysis, and carrying out reduced pressure concentration and repeated preparation through a rotary evaporator to obtain 7 sasanquasaponin monomer compounds.
2. Research on cytotoxin activity of camellia seed saponin compound
The effect of the camellia seed saponin compound on the in vitro proliferation activity of 3 tumor cells is detected by adopting a CCK-8 method, wherein a positive control is paclitaxel liquid medicine with a conventional concentration, and a negative control is DMSO with a concentration of 0.1%. Tumor cells include: human colon cancer cells (HCT-116), human leukemia cells (HL 60) and human liver cancer cells (HepG 2).
And selecting cells in the logarithmic growth phase for experiments. Cells were digested, counted, and prepared into a 1X 10 5/mL cell suspension, inoculated in 96-well plates (100. Mu.L/well), and incubated in a 5% CO 2 incubator at 37℃for 24h. The saponin solution was double diluted from 100. Mu.M to 0.39. Mu.M with medium, and the final concentrations of the compounds were 0.391. Mu.M, 0.781. Mu.M, 1.563. Mu.M, 3.125. Mu.M, 6.25. Mu.M, 12.5. Mu.M, 25. Mu.M, 50. Mu.M, and 100. Mu.M. 100 mu L of saponin liquid medicine with corresponding concentration is added into each hole, and a negative control group and a positive control group are simultaneously established, wherein each group is provided with 3 holes. After the 96-well plate was placed in a 37℃and 5% CO 2 incubator for 72 hours, the cell morphology of each group was observed under a microscope, 10. Mu.L of CCK8 solution was added to each well, incubation was continued in the cell incubator for 4 hours, absorbance was measured at 450nm, and proliferation inhibition was calculated.
3. Saponin monomer compound separated and identified from camellia seed meal
The experiment uses crude ethanol extract of camellia seed meal as raw material, and 7 camellia saponin monomer compounds are identified by a plurality of column chromatography separation technologies (AB-8 macroporous resin, forward silica gel and reverse silica gel), high performance liquid chromatography separation technology and modern spectrum (ultraviolet spectrum UV, infrared spectrum IR, high resolution mass spectrum HR-ESI-MS, nuclear magnetic resonance NMR and the like) analysis methods, and are all novel compounds. The compound names are given in table 1 below:
TABLE 1 saponin compounds isolated from tea seed meal
Note that: * Is a new compound
The structure of the saponin compound separated from the camellia seed meal is as follows:
4. anti-tumor cell activity of camellia seed saponin
The experiment adopts a CCK-8 method to detect the influence of the sasanqua seed saponin compound on the in vitro proliferation activity of 3 tumor cells, takes taxol liquid medicine with conventional concentration as positive control, and takes 0.1% DMSO as negative control. Tumor cells include: human colon cancer cells (HCT-116), human leukemia cells (HL 60) and human liver cancer cells (HepG 2).
1. Camellia seed saponin in vitro proliferation activity of resisting human colon cancer cell (HCT-116)
TABLE 2 inhibition of HCT-116 by tea seed saponins
Note that: *P<0.05,** P <0.01 compared to the negative control group.
As shown in Table 2, compounds 1 to 3 had little inhibitory effect on human colon cancer cells (HCT-116), and when the compound concentration reached 100. Mu.M, the cell inhibition rate for HCT-116 was also low. As shown in FIGS. 5 (a) to 5 (g), compounds 4 and 5 showed poor cytotoxic activity against HCT-116 cancer cells, with IC 50 values of 88.55. Mu.M and 63.60. Mu.M, respectively; compounds 6,7 and oleiferasaponin D 2、D3 show strong cytotoxic activity against HCT-116 cancer cells, and the IC 50 values are all about 1. Mu.M; total saponins show moderate cytotoxic activity against HCT-116 cancer cells, and the IC 50 value is 20.04 mu M; in a certain concentration range, the in-vitro proliferation activity of the sasanqua seed saponin compound for resisting HCT-116 cancer cells is positively correlated with the compound concentration.
2. Camellia seed saponin in vitro proliferation activity of anti-human leukemia cells (HL 60)
TABLE 3 inhibition of HL60 by tea seed saponins
Note that: *P<0.05,** P <0.01 compared to the negative control group.
As shown in Table 3, compounds 1 to 5 showed little inhibition on human leukemia cells (HL 60), and when the compound concentration reached 100. Mu.M, the cell inhibition rate on HL60 was less than 25%. As shown in fig. 6 (a) to 6 (e), compounds 6, 7 and oleiferasaponin D 2、D3 showed strong cytotoxic activity against HL60 cancer cells, with IC 50 values of 3.515 μm, 2.938 μm, 2.775 μm and 5.596 μm, respectively; the total saponins have weak cytotoxic activity to HL60 cancer cells, and the IC 50 value is 50.12 mu M; in a certain concentration range, the inhibition effect of the camellia seed saponin compound on HL60 tumor cells is positively correlated with the concentration of the camellia seed saponin compound.
3. Sasanqua seed saponin in vitro proliferation activity of anti-human liver cancer cell (HepG 2)
TABLE 4 inhibition of HepG2 by tea seed saponins
Note that: *P<0.05,** P <0.01 compared to the negative control group.
As shown in Table 4, the compounds 1 to 5 had no significant cytotoxic activity against human liver cancer cells (HepG 2), and the inhibition rate against HepG2 cancer cells was only about 30% at the highest when the compound concentration reached 100. Mu.M. As shown in fig. 7 (a) to 7 (e), compounds 6, 7 and oleiferasaponin D 2、D3 showed strong cytotoxic activity against HepG2 cancer cells, and IC 50 values were all about 2 μm; the total saponins show weak cytotoxic activity on HepG2 cancer cells, and the IC 50 value is 50.58 mu M; within a certain concentration range, the cytotoxic activity of the camellia seed saponin compound on HepG2 cancer cells is positively correlated with the compound concentration.
4. Analysis of anti-tumor Activity of tea seed saponins
The test result of the anti-tumor cell of the camellia seed saponin compound shows that: only compounds 4 and 5 of the compounds 1 to 5 show poor cytotoxic activity on HCT-116, and the other compounds have no obvious inhibition effect on 3 tumor cells; whereas compounds 6, 7 and oleiferasaponin D 2、D3 were very remarkable in vitro proliferation inhibitory activity against 3 tumor cells; the total saponins showed weak cytotoxic activity against 3 tumor cells. The IC 50 values of the cancer cell inhibitory activity of the camellia seed saponin compounds are shown in Table 5.
TABLE 5 cancer cell inhibitory Activity IC 50 value of tea seed saponins
The structural formulas of the compounds 1 to 7 and oleiferasaponin D 2、oleiferasaponin D3 are as follows:
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the cytotoxic activity data obtained in the test are analyzed by combining with the structure-activity relationship of the compounds, and the structural difference between the compounds 1 and 2 is only that the types of the connecting sugar on the sugar chain are different, and neither of the compounds shows obvious cytotoxic activity, which indicates that the sugar chain has little influence on the cytotoxic activity of the compounds. The only difference in structure between compound 6 and oleiferasaponin D 3 is that the hydrogen at carbon 21 of sapogenin 6 is substituted with acetyl, and the difference in cytotoxic activity is not large. By comparing the chemical structures of oleiferasaponin D 2 and D 3 with the cytotoxic activity data, it is found that the 22-carbon linkage of sapogenin has little effect on the cancer cell inhibitory activity. The structural differences between compounds 2,3 and 4 are only different in the type of organic acid attached to the carbon at position 16 of sapogenin, indicating that the type of organic acid attached to the carbon at position 16 has little effect on the cytotoxic activity of the compounds. From a comparison of the data of compounds 1-5 and compounds 6, 7, oleiferasaponin D 2、D3, it can be seen that the compounds having a hydroxyl group attached to the carbon at the 16-position of sapogenin all have significant cytotoxic activity, thus demonstrating that the hydroxyl group attached to the carbon at the 16-position plays a crucial role in the effect of cytotoxic activity.
The foregoing description of the preferred embodiment of the invention is merely illustrative of the invention and is not intended to be limiting. It will be appreciated by persons skilled in the art that many variations, modifications, and even equivalents may be made thereto without departing from the spirit and scope of the invention as defined in the appended claims.
Claims (4)
1. A camellia seed saponin compound is characterized in that the compound has the structure of
2. A camellia seed saponin compound is characterized in that the compound has the structure of
3. A process for the preparation of a camellia seed saponin compound as claimed in any one of claims 1 to 2, comprising the steps of:
s1, separating and purifying crude oil tea seed meal extract by macroporous resin column chromatography to obtain an elution component;
S2, eluting the elution component obtained by macroporous resin column chromatography in the step S1 by normal phase silica gel column chromatography, then eluting by reverse phase silica gel column chromatography, collecting the elution component, and further separating and purifying by high-liquid chromatography to obtain the camellia seed saponin compound;
In the step S1, the macroporous resin column chromatography is to dissolve crude oil tea seed extract with 75% ethanol, mix with AB-8 macroporous resin with equal mass, wet column packing with activated AB-8 macroporous resin, dry column packing, collecting 50:50 elution components, concentrating under reduced pressure to paste for subsequent treatment, wherein 50% elution part is saponin part with larger polarity;
The specific process of the step S2 is as follows: eluting the eluted components obtained by macroporous resin column chromatography by using ethyl acetate-methanol volume ratio of 6:1 to 0:1 as concentration gradient, combining components with the same Rf value, selecting the component No. 20 presenting purple spots, evaporating to dryness, performing ODS reversed-phase silica gel column chromatography, eluting by using methanol-water volume ratio of 30:70-100:0, collecting the eluted components of 40:60-50:50, and further separating and purifying by using high performance liquid phase to obtain the camellia seed saponin compound.
4. Use of a sasanqua seed saponin compound according to any one of claims 1-2 in the manufacture of a medicament against human colon cancer cells, human leukemia cells or human liver cancer cells.
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| "Cytotoxic and Hypoglycemic Activity of Triterpenoid Saponins from Camellia oleifera Abel. Seed Pomace";Tai-Mei Di et al.;《Molecules》;20171231;第22卷;第1562-1570页 * |
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