CN1414010A - Cardiac glycoside type compound for treating carcinosis and its preparation method - Google Patents
Cardiac glycoside type compound for treating carcinosis and its preparation method Download PDFInfo
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Abstract
A cardenolide compound for treating cancers is prepared from natural plant or Chinese medicine through chromatography with adsorption resin column, silica gel column, inverse silica gel column and medium-or low-pressure column, or through synthesis. It can be used to prepare anticancer medicines.
Description
Technical field:
The present invention relates to medical technical field, is a kind of cardiac glycoside compounds for the treatment of cancer and preparation method thereof with regard to it definitely.
Background technology:
Spore of fungi or the model deformation of mycelia can be used as the index of screening active compound, these are modal comprise unusually curling, expansion, hyperbranched, beads forms and growth is suppressed (Richmond, D.V.Adv.Appl.Microbiol.1975,19,289; Brain, P.W.Ann.Bot.1949,13,59:Betina, V.and Micekova, D.Z.Allg.Mikrobiol.1973,13,287; Isono, K., Kobinata, K.andSuzuki, S.Agric.Biol.Chem.1968,32,792).People such as holt virtue of a specified duration are deformed into screening index with plant pathogenic fungi Rice Blast Fungus filament shapes, have set up that a kind of to be used for screening the fungus twice meta-bolites antimycotic, quantitative screening model (Kobayashi, H., the Namikoshi of anticancer compound, M, Yoshimoto, T, and YokichiT.J.Antibiotics 1996,49,873), and obtain very strong rhizoxin (Tsuruo, the T. of cytotoxic activity, Oh-hara, T., Iida, H., Tsukagoshi, S., Sato, Z., Matsuda, I., Iwasaki, S., Okuda, S., Shimizu, F., Sasagawa, K., Fukami, M., Fukuda, K., and Arakawa, MCancer Res.1986,46,381) and very strong fusarielinA (Kobayashi, the H. of anti-mycotic activity, Sunaga, R., Furihata, K., Morisa ki, N.and Iwasaki, S.J.Antibiotics1995,48,42).The author continues to use this model that herbal medicine is carried out screening active ingredients, finds to have the new purposes of the cardiac glycoside compounds of general formula (I) at anticancer aspect under study for action.
Summary of the invention:
The objective of the invention is to systematically study the have general formula application of cardiac glycoside compounds in cancer therapy of (Shu), develop the new purposes of its antitumour activity.
The present invention is achieved in that to utilize and comprises multiple conventional separation means such as polymeric adsorbent column chromatography, silica gel column chromatography, reversed-phase silica gel column chromatography, mesolow column chromatography, from natural phant or Chinese medicine, obtain to have the cardiac glycoside compounds of general formula (I), perhaps obtain to have the cardiac glycoside compounds of general formula (I) by synthetic and semi-synthetic means.The compound form that employing is made up with arbitrary proportion with monomeric compound or the wherein any two or more monomers of selection, make it to combine with suitable vehicle, the powder of making according to ordinary method, granule, tablet, capsule, pill, suppository, pill, enteric agents, injection, syrup, emulsion, suspensoid, tincture, paste, formulations such as sprays are used for the preparation treatment and comprise lung cancer, leukemia, nasopharyngeal carcinoma, mammary cancer, ovarian cancer, colorectal carcinoma, liver cancer, skin carcinoma, prostate cancer, bladder cancer, chorioepithelioma, tumor of kidney, cancer of the stomach, the rectum cancer, uterus carcinoma, oral carcinoma, esophagus cancer, the courage cancer, cancer of bile ducts, cholangiocarcinoma, carcinoma of the pancreas, osteocarcinoma, laryngocarcinoma, tongue cancer, thymic carcinoma, lymphatic cancer, the malignant goiter knurl, cerebral tumor, central nerve neuroma, mediastinal tumor, melanoma, the medicine of multiple Cancerous disease such as sarcoma.
The cardiac glycoside of its formula of (I)
The structure of compounds is as follows:
In the general formula (I):
R
1＝OH，H，CH
2OH，OAC
R
2=by monose, disaccharide, trisaccharide, tetrose, pentasaccharides, various forms of straight chain sugar chains or side chain sugar chain that six sugar are formed, the sugar composed type of its sugar chain comprises β-D-glucose (β-D-glucose), alpha-D-glucose (α-D-glucose), α-L-rhamnosyl (α-L-rhamnose), β-D-semi-lactosi (β-D-galactose), α-D-semi-lactosi (α-D-galactose), β-D-seminose (β-D-mannose), α-D-seminose (α-D-mannose), β-D-pectinose (β-D-arabinose), α-D-pectinose (α-D-arabinose), β-D-wood sugar (β-D-xylose), α-I)-wood sugar (α-D-xylose), β-D-ribose (β-D-ribose), α-D-ribose (α-D-ribose), β-D-lyxose (β-D-lyxose), α-D-lyxose (α-D-vlyxose), α-D-husband sugar (α-D-fucose) and the above-mentioned corresponding 6-desoxy sugar of each six carbon aldose and 2,6-two desoxy sugars.
R
3＝OH，H，CH
2OH
R
4＝OAC，H，CH
3，OH
The present invention can preferably following compound as anti-cancer active matter:
In the general formula (I):
R
1＝H
R
2＝-α-L-Rha
R
3＝OH
R
4The compound rhodexin A of=H
In the general formula (I):
R
1＝H
R
2＝-α-L-Rha-
4β-D-Glc
R
3＝OH
R
4The compound wattoside F of=H
In the general formula (I):
R
1＝H
R
2＝-α-L-Rha-
4β-D-Glc
R
3＝H
R
4The compound wattoside G of=OAC
In the general formula (I):
R
i＝OH
R
2＝-α-L-Rha-
4β-D-Glc
R
3＝H
R
4The Verbindung uonymoside A of=H
In the general formula (I):
R
1＝OH
R
2＝-α-L-Rha-
4β-D-Glc-
6β-D-Glc
R
3＝H
R
4The Verbindung uonymoside A of=H
In the general formula (I):
R
1＝OH
R
2＝-α-L-Rha-
2β-D-Glc
R
3＝H
R
4The compound of=H
acovenosigenin?A-3-O-β-D-glncopyranosyl(1→2)-α-L-rhamnopyranoside
For the consumption of anticancer compound monomer or mixture, grownup 1～1000mg every day, takes 2～3 times every day at preferred 30～800mg/ day.
Oral administration can be made into common formulations such as tablet, powder, granule, capsule, needs a kind of vehicle at least, as starch, lactose, sucrose, seminose, Walocel MT 20.000PV etc.Except that these vehicle, also can use Magnesium Stearate, sodium laurylsulfate, talcum powder etc. as lubricant, dextrin, crystalline cellulose, polyvinylpyrrolidone, gum arabic, W-Gum, gelatin etc. are as tamanori, and yam starch, Walocel MT 20.000PV are as disintegrating agent.In addition, can also make syrup, emulsion, suspensoid etc.For these formulations, can add correctives, deodorizing agent etc.
Exterior-applied formulation comprises suppository, ointment, external pulvis, sprays, enema, emulsion or the like.Here employed solid or fluid additive often use in the present technique field.For ointment, select for use the hydrophobic base formed by water, fat, fatty oil, lanolin, Vaseline, glycerine, beeswax, paraffin, whiteruss, resin, higher alcohols, plastics, tensio-active agent or hydrophilic matrix etc. at interior additive.
When making injection, generally use distilled water for injection, physiological saline, D/W, injection vegetables oil, propylene glycol, polyoxyethylene glycol etc.In case of necessity, also can add suitable isotonic agent, solubility promoter, antioxidant, sanitas etc.
Advantage of the present invention is: cardiac glycoside compounds with general formula (I) the new purposes at anticancer aspect is provided, has been expected to develop the cancer therapy drug with good efficacy, and can be made into various formulations.
Embodiment:
Embodiment 1:
Cardiac glycoside compound rhodexin A, wattoside F, the extraction separation of wattoside G
The fresh rhizome 6.5kg of liliaceous plant Tupistra wattii extracts with 95% alcohol heating reflux, and concentrated extracting solution obtains ethanol extraction.This extract mixture is suspended from the water, obtains water dissolution part and water and do not dissolve part.Partly by the HP-20 macroporous resin column, first water wash-out is used 70% ethanol elution then instead with water dissolution, 70% ethanol elution part is through silica gel column chromatography, with the RP-8 column chromatography, obtain compound rhodexin A (19.0mg), wattoside F (8.2mg) and wattoside G (45.1mg).
Embodiment 2:
Cardiac glycoside compounds rhodexin A, the structure of the sharp wattoside G of wattoside F is identified
Utilize spectroscopic techniques, comprise ultraviolet, infrared, mass spectrum and nmr analysis (1D-NMR and 2D-NMR), identified the cardiac glycoside compounds rhodexin A among the embodiment 1, wattosideF, the structure of wattoside G.Utilization 2D-NMR technology has especially solved substituent position and the sugared order of connection and mode of connection on the cardiac aglycone by the HMBC spectrum, and hydrogen signal and carbon signal are belonged to (seeing accompanying drawing) accurately
Embodiment 3:
Cardiac glycoside compounds rhodexin A among the embodiment 1, the external knurl that presses down of wattoside F and wattoside G is tested
Cardiac glycoside compounds rhodexin A among the embodiment 1, wattoside F, wattoside G amounts to 4 knurl strain K562 (people's chronic myeloid leukemia cells) to 3 cancer systems of human body, HCT-15 (human colon cancer cell), HT1080 (human fibrosarcoma), the external antitumor activity experiment (the results are shown in Table 3) of A431 (people's squamous epithelium cancer cells), active testing adopts mtt assay.Various knurl strains are all cultivated with the PRMI1640 substratum that contains 10% calf serum (FCS), 100IU/ml penicillin (penicillin) and 100 μ g/ml (streptomycin).Cell adds the cell suspension that 0.2ml contains 1000 oncocytes in each hole of 96 orifice plates after cultivating in 24 hours, add the MTT solution (2mg/ml) of 50 μ l in each hole of 96 orifice plates, continues to cultivate 4 hours.Remove substratum, added dimethyl sulfoxide (DMSO) (DMSO) 200 μ l dissolved cells in every hole 10 minutes.Then, 96 orifice plates carry out reading at the 540nm place with micro titer plate reader (DynatechMR5000).Not add the cell (100% survival rate) in contrast of inspection product (rhodexin A, wattoside F and wattoside G), calculate the IC of sample
50Value.
Embodiment 4:
Cardiac glycoside compounds rhodexin A25g mixes with Microcrystalline Cellulose 90g and Magnesium Stearate 10g, and mixture breaks into Φ 6mm with Singlepunchtabletpress, the sheet of weight 300mg.Every contains cardiac glycoside rhodexin A60mg in this tablet.In conjunction with illness, each 2～3 times, take every day 2～3 times.
Embodiment 5:
Cardiac glycoside compounds wattoside F10g mixes with W-Gum 90g, adds water and makes softwood, crosses 12 mesh sieves and carries out granulation, obtains granule after the drying.In this granule, contain cardiac glycoside wattosideF50mg among every 500mg.In conjunction with symptom, each 1.0～2.0g takes 2～3 every day.
Embodiment 6:
Cardiac glycoside compounds wattoside G40g mixes with lactose 110g, Magnesium Stearate 10g, with every 500mg filled capsules.In this capsule, each capsule contains cardiac glycoside wattoside G125mg.In conjunction with symptom, each 1～2, take every day 2～3 times.
Embodiment 7:
Cardiac glycoside compounds acovenosigenin A-3-O-β-D-glucopyranosyl (1 → 2)-α-L-rhamnopyranoside10g adds water 300ml dissolving, adds hesperidine 4ml, adds simple syrup and gets syrup to 1000ml.Contain cardiac glycoside acovenosigenin A10mg among this syrup 1ml.In conjunction with symptom, each 10～15ml takes 2～3 every day.
Embodiment 8:
Cardiac glycoside Verbindung uonymoside A and each 50g of wattoside F mix with Microcrystalline Cellulose 90g and Magnesium Stearate 10g, and mixture breaks into the tablet of Φ 6mm with the one-shot tablet machine, and uses the CAP film coating, makes the enteric coated tablet of weight 300mg.Every contains cardiac glycoside euonymoside A and each 75mg of wattoside F in these enteric coated tablet.In conjunction with symptom, each 1～2, take every day 2～3 times.
Embodiment 9:
Cardiac glycoside compounds euonymoside A20g and wattoside G10g mix with lactose 85g, Magnesium Stearate 5g, fill enteric coated capsule with every 600mg.In this enteric coated capsule, each capsule contains cardiac glycoside 100mg and wattoside G50mg.In conjunction with symptom, each 1～2, take every day 2～3 times.
Embodiment 10:
Cardiac glycoside compounds wattoside G20g is the agent preparation method during with common notes, with the injection distilled water 1000ml dissolving that is heated to 60 ℃, regulates to wait with NaCl and opens, and encloses the peace bottle.Contain cardiac glycoside wattoside G200mg among this injection 10ml.In conjunction with symptom, each intramuscular injection 10ml injects 2 every day.
Cardiac glycoside compound rhodexin A among table 1, the embodiment 1,2, physicochemical constant and the spectroscopic data of wattoside F and wattoside G
Rhodexin A: white prismatic crystal: mp238-240 ℃; [α]
18I)-88.92 (c0.0069, CHCI
3); IR (KBr): v
Max=3374,1745,1616cm
-1EI-MS m/z:519,463,266,251,223,208,149;
1H-NMR (500MHZ, C
5D
5N): δ 1.106 (3H, s, Me-18), 1.113 (3H, s, Me-19), 5.04 (1H, d, J=18.1Hz, H-21), 5.29 (1H, d, J=18.1Hz, H-21), 6.11 (1H, br.s, H-22), 4.09 (1H, br.t, H-11), 5.42 (1H, br.s, H-1 '), (1.63 3H, d, J=5.34Hz, H-6 ');
13C-NMR (125MHz, C5D5N): table 2
Wattoside F: white needle; Mp262-265 ℃; [α]
18I)-93.15 (c0.0023, MeOH); IR (KBr): v
Max=3400,1736,1623cm
-1HRFAB-MS:m/z697.3500, [M-H]
-, calcd 697.3499, C
35H
54O
14FAB-MS:m/z697[M-H]
-, 535[M-Glc]
-, 389[M-Glc-Rha]
- 1H-NMR (500MHZ, C
5D
5N): 1.09 (3H, s, H-18), 0.11 (3H, s, H-19), 5.02 (1H, dd, J=1.4,18.1Hz, H-21), 5.27 (1H, dd, J=1.4,18.1Hz, H-21), 6.10 (1H, brs, H-22), 1.65 (3H, d, J=6.5Hz, H-6 '), 5.60 (1H, br.s, H-1 '), 5.20 (1H, d, J=7.4Hz, H-1 ");
13C-NMR (125MHz, C
5D
5N): table 2
Wattoside G: white needle; Mp232-235 ℃; [α]
20D-39.9 ° (c0.57, MeOH); IR (KBr): v
Max=3400,1720,1600cm
-1FAB-MS m/z:739[M-H]
-, 577[M-Glc]
-, 431[M-Glc-Rha]
- 1H-NMR (500MHZ, C
5D
5N): δ 5.68 (1H, td, J=9.4,2.1Hz, H-16), 3.39 (1H, d, J=8.7Hz, H-17), 1.08 (3H, s, H-18), 0.84 (3H, s, H-19), 5.23 (1H, dd, J=1.5,18.3Hz, H-21), 5.42 (1H, dd, J=1.5,18.3Hz, H-21), 6.34 (1H, brs, H-22), (1.70 3H, d, J=6.2Hz, H-6 '), 5.34 (1H, br.s, H-1 '), 5.23 (1H, d, J=7.7Hz, H-1 "), 1.84 (3H, s, Oac-CH3);
13C-NMR (125MHz, C
5D
5N): table 2
Cardiac glycoside compound rhodexin A among table 2 embodiment 1,2, wattoside F and wattoside G's
13(δ ppm, 125MHz, solvent are C to the C-NMR data
5D
5N)
position????????rhodexin?A???????wattoside?F??????wattoside?G
1??????????????33.86?????????????33.91????????????30.25
2??????????????28.17?????????????28.16????????????27.12
3??????????????73.05?????????????73.42????????????72.91
4??????????????31.06?????????????31.20????????????31.04
5??????????????38.90?????????????38.94????????????37.09
6??????????????27.33?????????????27.37????????????26.89
7??????????????22.26?????????????22.28????????????21.25
8??????????????41.32?????????????41.35????????????41.96
9??????????????42.32?????????????42.35????????????35.77
10?????????????37.03?????????????37.06????????????35.50
11?????????????67.76?????????????67.81????????????21.74
12?????????????50.61?????????????50.63????????????39.10
13?????????????50.33?????????????50.36????????????50.58
14?????????????84.30?????????????84.34????????????83.49
15?????????????33.63?????????????33.65????????????41.29
16?????????????27.71?????????????27.72????????????75.08
17?????????????51.30?????????????51.33????????????56.86
18?????????????17.66?????????????19.69????????????16.38
19?????????????24.51?????????????24.56????????????24.06
20?????????????175.60????????????175.63???????????170.40
21?????????????73.83?????????????73.88????????????76.41
22?????????????117.77????????????117.79???????????121.65
23?????????????174.62????????????174.66???????????174.38
1’??????????????????????????100.10????????????99.99????????????99.77
2’??????????????????????????73.05?????????????85.45????????????85.38
3’??????????????????????????73.05?????????????72.49????????????72.38
4’??????????????????????????74.20?????????????72.92????????????72.59
5’??????????????????????????70.12?????????????68.41????????????68.44
6’??????????????????????????18.70?????????????18.50????????????18.55
1”?????????????????????????????????????????????????????????????106.92???????????106.90
2”??????????????????????????????????????????????????????????????76.53????????????76.53
3”???????????????????????????????????????????????????????????????78.59????????????78.63
4”???????????????????????????????????????????????????????????????71.51????????????71.52
5”????????????????????????????????????????????????????????????????78.59????????????78.53
6”????????????????????????????????????????????????????????????????62.67????????????62.68
CH
3-COO-???????????????????????????????????????20.81，170.03
The external knurl that presses down of cardiac glycoside compound wattoside G is tested among table 3 embodiment 1,2
a
| Compound | ???????????????????????IC 50(μM) | |||
| ????K562 | ????HCT-15 | ????HT1080 | ????A431 | |
| ??wattoside?E | ????0.01 | ????1.4 | ????39.6 | ????2.5 |
| ??cis-DDP b | ????69.33 | ????69.50 | ????333.3 | ????1.7 |
aBut external knurl is tested and is comprised that 3 cancers of human body are 4 knurl strain K562 (people's chronic myeloid leukemia cells), HCT-15 (human colon cancer cell), HT1080 (human fibrosarcoma), A431 (people's squamous epithelium cancer cells).
bPositive control
Claims (10)
1, a kind of cardiac glycoside compounds for the treatment of cancer and preparation method thereof, it is characterized in that: utilize to comprise multiple conventional separation means such as polymeric adsorbent column chromatography, silica gel column chromatography, reversed-phase silica gel column chromatography, mesolow column chromatography, from natural phant or Chinese medicine, obtain to have the cardiac glycoside compounds of general formula (I), perhaps obtain to have the cardiac glycoside compounds of general formula (I) by synthetic and semi-synthetic means
The structure of the cardiac glycoside compounds of general formula (I).
In the general formula (I):
R
1＝OH，H，CH
2OH，OAC
R
2=by monose, disaccharide, trisaccharide, tetrose, pentasaccharides, various forms of straight chain sugar chains or side chain sugar chain that six sugar are formed, the sugar composed type of its sugar chain comprises β-D-glucose (β-D-glucose), alpha-D-glucose (α-D-glucose), α-L-rhamnosyl (α-L-rhamnose), β-D-semi-lactosi (β-D-galactose), α-D-semi-lactosi (α-D-galactose), β-D-seminose (β-D-mannose), α-D-seminose (α-D-mannose), β-D-pectinose (β-D-arabinose), α-D-pectinose (α-D-arabinose), β-D-wood sugar (β-D-xylose), alpha-D-xylose (α-D-xylose), β-D-ribose (β-D-ribose), α-D-ribose (α-D-ribose), β-D-lyxose (β-D-lyxose), α-D-lyxose (α-D-vlyxose), α-D-husband sugar (α-D-fucose) and the above-mentioned corresponding 6-desoxy sugar of each six carbon aldose and 2,6-two desoxy sugars.
R
3＝OH，H，CH
2OH
R
4＝OAC，H，CH
3，OH
2, a kind of cardiac glycoside compounds for the treatment of cancer according to claim 1 and preparation method thereof, it is characterized in that: adopt cardiac glycoside compounds with general formula (I), with monomeric compound or the compound form of selecting wherein any two or more monomers to make up with arbitrary proportion, make it to combine the interior injection and the application of exterior-applied formulation in the preparation cancer treatment drugs of the oral administration of making according to ordinary method with formulation and non-oral administration with suitable vehicle.
3, a kind of cardiac glycoside compounds for the treatment of cancer according to claim 1 and preparation method thereof is characterized in that: used active substance is in the general formula (I),
R
1＝H
R
2＝-α-L-Rha
R
3＝OH
R
4＝H
4, a kind of cardiac glycoside compounds for the treatment of cancer according to claim 1 and preparation method thereof is characterized in that: used active substance is in the general formula (I),
R
1＝H
R
2＝-α-L-Rha-
4β-D-Glc
R
3＝OH
R
4＝H
5, according to a kind of cardiac glycoside compounds for the treatment of cancer as claimed in claim 1 and preparation method thereof, it is characterized in that: used active substance is in the general formula (I),
R
1＝H
R
2＝-α-L-Rha-
4β-D-Glc
R
3＝H
R
4＝OAC
6, according to a kind of cardiac glycoside compounds for the treatment of cancer as claimed in claim 1 and preparation method thereof, it is characterized in that: used active substance is in the general formula (I),
R
1＝OH
R
2＝-α-L-Rha
R
3＝H
R
4＝H
7, according to a kind of cardiac glycoside compounds for the treatment of cancer as claimed in claim 1 and preparation method thereof, it is characterized in that: used active substance is in the general formula (I),
R
1＝OH
R
2＝-α-L-Rha-
4β-D-Glc
R
3＝H
R
4＝H
8, according to a kind of cardiac glycoside compounds for the treatment of cancer as claimed in claim 1 and preparation method thereof, it is characterized in that: used active substance is in the general formula (I),
R
1＝OH
R
2＝-α-L-Rha-
4β-D-Glc-
6β-D-Glc
R
3＝H
R
4＝H
9, according to a kind of cardiac glycoside compounds for the treatment of cancer as claimed in claim 1 and preparation method thereof, it is characterized in that: used active substance is in the general formula (I),
R
1＝OH
R
2＝-α-L-Rha-
4β-D-Glc
R
3＝H
R
4＝H
10, a kind of cardiac glycoside compounds for the treatment of cancer according to claim 1 and preparation method thereof, it is characterized in that: employing, can be used for the preparation treatment and comprises lung cancer with compound or the made preparation of compound form with monomer, leukemia, nasopharyngeal carcinoma, mammary cancer, ovarian cancer, colorectal carcinoma, liver cancer, skin carcinoma, prostate cancer, bladder cancer, chorioepithelioma, tumor of kidney, cancer of the stomach, the rectum cancer, uterus carcinoma, oral carcinoma, esophagus cancer, the courage cancer, cancer of bile ducts, cholangiocarcinoma, carcinoma of the pancreas, osteocarcinoma, laryngocarcinoma, tongue cancer, thymic carcinoma, lymphatic cancer, the malignant goiter knurl, cerebral tumor, central nerve neuroma, mediastinal tumor, melanoma, the medicine of multiple Cancerous disease such as sarcoma.
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| WO2006029018A3 (en) * | 2004-09-02 | 2006-05-11 | Bionaut Pharmaceuticals Inc | Combinatorial chemotherapy treatment using na+/k+-atpase inhibitors |
| CN102071241A (en) * | 2010-08-31 | 2011-05-25 | 天津科技大学 | Method for dehydrogenation at C16 and C17 sites of cardiac glycoside aglycome by using spherical arthrobacter |
| CN102071241B (en) * | 2010-08-31 | 2012-09-19 | 天津科技大学 | Method for dehydrogenation at C16 and C17 sites of cardiac glycoside aglycome by using spherical arthrobacter |
| CN102416019A (en) * | 2011-11-18 | 2012-04-18 | 桂林医学院 | Application of cedilanid in preparation of anti-liver cancer and anti-bladder cancer medicament |
| CN112618528A (en) * | 2020-07-07 | 2021-04-09 | 中山大学 | Application of Fusariulin M and derivatives and pharmaceutically acceptable salts thereof |
| CN112209986A (en) * | 2020-09-21 | 2021-01-12 | 西北农林科技大学 | Steroid compound, preparation method and application |
| CN112209986B (en) * | 2020-09-21 | 2022-11-22 | 西北农林科技大学 | Steroid compound, preparation method and application |
| CN113968893A (en) * | 2021-11-11 | 2022-01-25 | 兰州大学 | Cardiac glycoside with anti-angiogenesis activity and preparation method and application thereof |
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