CN103755692A - Compound, preparation method and application thereof, pharmaceutical composition and preparation - Google Patents
Compound, preparation method and application thereof, pharmaceutical composition and preparation Download PDFInfo
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- CN103755692A CN103755692A CN201410043320.5A CN201410043320A CN103755692A CN 103755692 A CN103755692 A CN 103755692A CN 201410043320 A CN201410043320 A CN 201410043320A CN 103755692 A CN103755692 A CN 103755692A
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D407/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having oxygen atoms as the only ring hetero atoms, not provided for by group C07D405/00
- C07D407/02—Heterocyclic compounds containing two or more hetero rings, at least one ring having oxygen atoms as the only ring hetero atoms, not provided for by group C07D405/00 containing two hetero rings
- C07D407/04—Heterocyclic compounds containing two or more hetero rings, at least one ring having oxygen atoms as the only ring hetero atoms, not provided for by group C07D405/00 containing two hetero rings directly linked by a ring-member-to-ring-member bond
Abstract
The invention relates to the field of medicines, in particular to a compound, a preparation method and application thereof, a pharmaceutical composition and a preparation. The compound is a compound as shown in the formula I, wherein Ac is acetyl. The compound as shown in the formula I is a novel xanthone compound, has obvious effects of resisting the tumor activity, reducing the blood sugar and reducing the serum urate level of a hyperuricemia mice, and can be used for preparing antitumor drugs, drugs for preventing or treating diabetes or drugs with the function of adjusting the blood uric acid. The preparation method of the compound as shown in the formula I has the advantages of simple operation, easiness in obtaining of raw materials and mild reaction conditions, and can be used for large-scale preparation of the compound as shown in the formula I (seen in the specification).
Description
Technical field
The present invention relates to field of pharmacology, relate to specifically a kind of compound and preparation method thereof, purposes, pharmaceutical composition and preparation.
Background technology
Xanthone is a kind of organic compound, can through heating, be made by salol.Nineteen thirty-nine, xanthone starts to be used to manufacture sterilant, is used as afterwards ovicide (ovicide) and the larvacide (larvicide) of carpocapsa pononella (codling moth) ovum.Xanthone is also used to prepare flavol.Xanthone reduzate is xanthgdrol, for the identification of aliphatic amide type, amino formate compounds, is also used as the blocking group of acyloxy.
There is the derivative of numerous xanthones in occurring in nature, as mangostin etc., they are referred to as xanthone compounds.This compounds is mainly present in some more high plant species, in the plants such as Gentianaceae, Moraceae, guttiferae, Polygalaceae, pulse family and fungi and lichens.The xanthone compounds of different structure, often has different pharmacological actions or level of activity.At present, the mankind find, have isolated more than 200 kind of xanthone compounds, pharmacological research shows, has found that xanthone compounds has pharmacologically active very widely, comprises diuresis, antibacterial, antiviral, cardiac stimulant, antidepressant, tuberculosis, anticancer, anti-liver poison isoreactivity.On the basis of natural drug, utilize chemical means to synthesize new compound, be the effective way that the world today finds new drug.Therefore,, in recent years by the method for organic synthesis, synthetic have certain physiology and pharmacologically active xanthone compounds, becomes the focus of people's research.
Summary of the invention
In view of this, the object of the invention is to provide a kind of have certain physiology and pharmacologically active xanthone compounds.
For realizing object of the present invention, the present invention adopts following technical scheme:
A compound shown in formula I,
Wherein, Ac is ethanoyl.
The present invention also provides the preparation method of compound shown in a kind of formula I, and under catalyst action, 1,6,7-trihydroxy--3-methoxyl group xanthone-2-C-β-D-glucopyranoside reacts and makes in solvent with diacetyl oxide.
Preferably, described 1,6, the mol ratio of 7-trihydroxy--3-methoxyl group xanthone-2-C-β-D-glucopyranoside and diacetyl oxide is 1.0:5.0～1.0:10.0.
Preferably, described catalyzer is acetate.
Preferably, described acetate is sodium acetate or potassium acetate.
Preferably, described solvent is Glacial acetic acid.
Preferably, described temperature of reaction is 40 ℃～70 ℃.
Preferably, the described reaction times is 2h～5h.
The present invention also provides compound shown in formula I preparing antitumor drug, prevention or treatment diabetes medicament or having the application regulating in blood uric acid function medicament.
The present invention also provides a kind of pharmaceutical composition, comprises compound shown in formula I described in the claim 1 for the treatment of significant quantity.
The present invention also provides a kind of pharmaceutical preparation, comprises compound shown in the formula I that treats significant quantity and pharmaceutically acceptable auxiliary material.
Preferably, described pharmaceutical preparation is tablet, capsule, injection liquid or lyophilized injectable powder.
Compound shown in formula I of the present invention is a new xanthone compounds, there is the effect of the serum uric acid level of obvious anti-tumor activity, hypoglycemic activity and reduction hyperuricemia mouse, can be used for preparing antitumor drug, prevention or treatment diabetes medicament or there is the blood uric acid of adjusting function medicament.Shown in formula I of the present invention, the preparation method of compound, simple to operate, and raw material is easy to get, and reaction conditions is gentle, can be used for a large amount of preparations of compound shown in formula I.
Embodiment
The embodiment of the invention discloses a kind of compound and preparation method thereof, purposes, pharmaceutical composition and preparation.Those skilled in the art can use for reference content herein, suitably improve processing parameter and realize.Special needs to be pointed out is, all similar replacements and change apparent to those skilled in the artly, they are all deemed to be included in the present invention.Product of the present invention, method and application are described by preferred embodiment, related personnel obviously can change product as herein described, method and application or suitably change and combination within not departing from content of the present invention, spirit and scope, realizes and apply the technology of the present invention.
For realizing object of the present invention, the present invention adopts following technical scheme:
The present invention utilizes modern chemistry to synthesize and structure of modification means have obtained a kind of new xanthone compounds, and it has structure shown in formula I,
Wherein, Ac is ethanoyl.
The present invention also provides the preparation method of compound shown in a kind of formula I, and under catalyst action, 1,6,7-trihydroxy--3-methoxyl group xanthone-2-C-β-D-glucopyranoside reacts and makes in solvent with diacetyl oxide.Reaction formula is as follows:
Wherein, Ac is ethanoyl.
Wherein, shown in formula I of the present invention in the preparation method of compound, described 1,6,7-trihydroxy--3-methoxyl group xanthone-2-C-β-D-glucopyranoside, claims again 1,6, the two benzene pyrrone-2-C-β-D-glucopyranosides of 7-trihydroxy--3-methoxyl group, its structural formula, suc as formula shown in II, can prepare according to existing document or the disclosed method of patent.
As preferably, shown in formula I of the present invention in the preparation method of compound, described 1,6, the mol ratio of 7-trihydroxy--3-methoxyl group xanthone-2-C-β-D-glucopyranoside and diacetyl oxide is 1.0:5.0～1.0:10.0.
In some embodiments, shown in formula I of the present invention, in the preparation method of compound, described catalyzer is acetate.At catalyzer described in some specific embodiments, it is sodium acetate.At catalyzer described in other specific embodiments, it is potassium acetate.
In some embodiments, shown in formula I of the present invention, in the preparation method of compound, described solvent is Glacial acetic acid.
As preferably, shown in formula I of the present invention in the preparation method of compound, described 1, the mol ratio of 6,7-trihydroxy--3-methoxyl group xanthone-2-C-β-D-glucopyranoside and diacetyl oxide, acetate, Glacial acetic acid is 1.0:(5.0～10.0): (2.0～6.0): (10.0～15.0).Described in some specific embodiments 1,6, the mol ratio of 7-trihydroxy--3-methoxyl group xanthone-2-C-β-D-glucopyranoside and diacetyl oxide, sodium acetate, Glacial acetic acid is 1.0:8.0:4.0:12.0.Described in some specific embodiments 1,6, the mol ratio of 7-trihydroxy--3-methoxyl group xanthone-2-C-β-D-glucopyranoside and diacetyl oxide, sodium acetate, Glacial acetic acid is 1.0:10.0:3.0:15.0.Described in other specific embodiments 1,6, the mol ratio of 7-trihydroxy--3-methoxyl group xanthone-2-C-β-D-glucopyranoside and diacetyl oxide, potassium acetate, Glacial acetic acid is 1.0:5.0:2.0:10.0.
Preparation method's of the present invention temperature of reaction is generally 40 ℃～70 ℃.In some specific embodiments, described temperature of reaction is 60 ℃; In some specific embodiments, described temperature of reaction is 40 ℃; In other specific embodiments, described temperature of reaction is 70 ℃.
Preparation method's of the present invention reaction times is generally 2h～5h.In some embodiments, the described reaction times is 3h～4h.In some specific embodiments, the described reaction times is 3h; In some specific embodiments, the described reaction times is 4h; In other specific embodiments, the described reaction times is 4h.
Further, after preparation method's reaction of the present invention finishes, need reaction solution to carry out purifying, separation obtains compound shown in formula I.Described purification process concrete grammar stirs for adding water 20mL, with petroleum ether extraction reaction solution 2 times (2 * 50mL), collects petroleum ether extraction liquid, and vacuum reclaims sherwood oil, crystallization and get final product.
Through mass spectrum, nuclear magnetic resonance spectroscopy, determine that the xanthone compounds preparing is 1-hydroxy-3-methoxy-6, the tetra-acetylated glucopyranoside of 7-diacetoxy xanthone-2-C-β-D-.
MTT colorimetry is the method that in vitroanticancer drug screening is conventional, has simply, fast, accurately, do not relate to use radioelement and result to mix the advantages such as method is consistent with isotropic substance, is widely used the common method as in vitroanticancer drug screening.In a specific embodiments, it is research object that Hela, A-549, Bel-7402 and the HL-60 tumour cell of logarithmic phase take in the present invention, by mtt assay, carry out anti-tumor activity experiment, find that compound shown in formula I of the present invention has obvious restraining effect to Hela, A-549, Bel-7402 and HL-60 growth of tumour cell, shows that shown in formula I of the present invention, compound has obvious anti-tumor activity.Therefore the invention provides the application of compound shown in formula I in preparing antitumor drug.
In a specific embodiments, by tetraoxypyrimidine hyperglycemia mouse blood sugar impact test, find that compound shown in formula I of the present invention has obvious hypoglycemic activity to tetraoxypyrimidine hyperglycemia mouse.Therefore the invention provides the application of compound shown in formula I in preparation prevention or treatment diabetes medicament.
In another embodiment, the present invention, by the impact of the acute hyperuricemia mouse uric acid of Oteracil Potassium induction is tested, proves that compound shown in formula I of the present invention can significantly reduce the serum uric acid level of hyperuricemia mouse.Therefore the present invention also provides compound shown in formula I to have in preparation the application regulating in blood uric acid function medicament.
The present invention also provides a kind of pharmaceutical composition, comprises compound shown in the formula I of the present invention that treats significant quantity.
The present invention also provides a kind of pharmaceutical preparation, comprises compound and pharmaceutically acceptable auxiliary material shown in the formula I of the present invention that treats significant quantity.Those skilled in the art can directly or indirectly add compound shown in described formula I pharmaceutically acceptable various conventional auxiliary materials required while preparing different dosage form, as weighting agent, disintegrating agent, lubricant, tackiness agent etc., with conventional medicine formulation method, make common dosage forms as tablet, capsule, injection liquid, oral liquid, granule, pill, powder and pill etc.Wherein, weighting agent is as starch, lactose, sucrose, glucose, N.F,USP MANNITOL and silicic acid; Disintegrating agent is as agar, calcium carbonate, potato starch or tapioca (flour), Lalgine, some silicate and sodium carbonate, low-substituted hydroxypropyl cellulose; Lubricant is as talcum powder, calcium stearate, Magnesium Stearate, solid polyethylene glycol, Sulfuric acid,monododecyl ester, sodium salt; Tackiness agent is as carboxymethyl cellulose, alginate, gelatin, Povidone, sucrose and gum arabic.
In some embodiments, pharmaceutical preparation of the present invention is tablet, capsule, injection liquid or lyophilized injectable powder.
Compound shown in formula I of the present invention is new xanthone compounds, there is the effect of the serum uric acid level of obvious anti-tumor activity, hypoglycemic activity and reduction hyperuricemia mouse, can be used for preparing antitumor drug, prevention or treatment diabetes medicament or there is the blood uric acid of adjusting function medicament.Shown in formula I of the present invention, the preparation method of compound, simple to operate, and raw material is easy to get, and reaction conditions is gentle, can be used for a large amount of preparations of compound shown in formula I.
In order further to understand the present invention, below in conjunction with embodiment, the present invention is described in detail.
Embodiment 1:1-hydroxy-3-methoxy-6, the preparation of the tetra-acetylated glucopyranoside of 7-diacetoxy xanthone-2-C-β-D-
In 1000mL reaction flask; add 43.6g (0.1mol) 1; 6; 7-trihydroxy--3-methoxyl group xanthone-2-C-β-D-glucopyranoside, 81.6g (0.8mol) diacetyl oxide, 32.8g (0.4mol) sodium acetate, 72.0g (1.2mol) Glacial acetic acid; in 60 ℃ of stirring reaction 3h; add water 200mL; with petroleum ether extraction 2 times (2 * 300mL); collect petroleum ether extraction liquid; vacuum reclaims sherwood oil, and crystallization, obtains 1-hydroxy-3-methoxy-6; the tetra-acetylated glucopyranoside 65.3g of 7-diacetoxy mountain ketone-2-C-β-D-, yield 94.9%.Spectral data:
1hNMR (CDCl
3) δ: 13.09(1H ,-OH), 7.73 (1H, Ar-H), 6.72 (1H, Ar-H), 6.47 (1H, Ar-H), 6.34 (1H, Ar-H), 3.97 (3H ,-OCH
3), 5.44-3.90(7H, glc-H); Positive FABMS:m/z689[M+H]
+; Positive HRFABMS m/z689.1733[M+H]
+, Calcd.for C
32h
33o
17, 689.1731.
Embodiment 2:1-hydroxy-3-methoxy-6, the preparation of the tetra-acetylated glucopyranoside of 7-diacetoxy xanthone-2-C-β-D-
In 1000mL reaction flask; add 43.6g (0.1mol) 1; 6; 7-trihydroxy--3-methoxyl group xanthone-2-C-β-D-glucopyranoside, 102.0g (1.0mol) diacetyl oxide, 24.6g (0.3mol) sodium acetate, 90.0g (1.5mol) Glacial acetic acid; in 40 ℃ of stirring reaction 4h; add water 200mL; with petroleum ether extraction 2 times (2 * 300mL); collect petroleum ether extraction liquid; vacuum reclaims sherwood oil, and crystallization, obtains 1-hydroxy-3-methoxy-6; the tetra-acetylated glucopyranoside 65.5g of 7-diacetoxy mountain ketone-2-C-β-D-, yield 95.2%.Spectral data is with embodiment 1.
Embodiment 3:1-hydroxy-3-methoxy-6, the preparation of the tetra-acetylated glucopyranoside of 7-diacetoxy xanthone-2-C-β-D-
In 1000mL reaction flask; add 43.6g (0.1mol) 1; 6; 7-trihydroxy--3-methoxyl group xanthone-2-C-β-D-glucopyranoside, 51.0g (0.5mol) diacetyl oxide, 19.6g (0.2mol) potassium acetate, 60.0g (1.0mol) Glacial acetic acid; in 40 ℃ of stirring reaction 4h; add water 200mL; with petroleum ether extraction 2 times (2 * 300mL); collect petroleum ether extraction liquid; vacuum reclaims sherwood oil, and crystallization, obtains 1-hydroxy-3-methoxy-6; the tetra-acetylated glucopyranoside 63.1g of 7-diacetoxy mountain ketone-2-C-β-D-, yield 91.7%.Spectral data is with embodiment 1.
Embodiment 4: anti-tumor activity experiment
Adopt mtt assay, by different tumour generating rates, by the Hela in logarithmic phase, A-549, Bel-7402, HL-60 tumour cell is inoculated in respectively in 96 well culture plates, and every hole 90 μ L add respectively compound shown in formula I (embodiment 1 preparation), reference substance (1 after cultivation 24h, 6,7-trihydroxy--3-methoxyl group xanthone-2-C-β-D-glucopyranoside), every hole 10 μ L, each concentration of each cell strain is all established three repeating holes.Then at 37 ℃, 5%CO
2under condition, cultivate 48h, add 5mg/L MTT liquid, every hole 20 μ L, continue to cultivate after 4h, add the every hole 50 μ L of three liquid (10%SDS-5% isopropylcarbinol-0.01mol/L HCl) in CO
2in incubator, spend the night, then by microplate reader, under 570nm, measure OD value.Calculate the inhibiting rate of analyte to growth of tumour cell, adopt Logit method to calculate half amount of suppression IC
50value, the results are shown in Table 1.
Table 1 anti-tumor activity experimental result
From table 1, compound shown in formula I of the present invention has obvious inhibition to Hela, A-549, Bel-7402 and HL-60 growth of tumour cell, shows that shown in formula I of the present invention, compound has obvious anti-tumor activity.
Embodiment 5: hypoglycemic activity experiment
Get normal mouse, tail vein injection tetraoxypyrimidine (80mg/kg), after 72h, measure serum level of glucose, select blood glucose value as confession, to try mouse the above mouse of 16mmol/L, be divided into Normal group, tetraoxypyrimidine group, medicine control group (1,6,7-trihydroxy--3-methoxyl group xanthone-2-C-β-D-glucopyranoside), compound group shown in formula I (embodiment 1 preparation).Every day, gastric infusion was 1 time, and Normal group, tetraoxypyrimidine group give equal-volume distilled water, continuous 7 days.1h after last administration, gets blood from mouse orbit venous plexus, uses kit measurement glucose level after centrifuging and taking serum.The results are shown in Table 2.
Table 2 is on the impact of alloxan diabetes mouse blood sugar (x ± s, n=10)
From table 2 result, obviously reduce giving shown in formula I of the present invention tetraoxypyrimidine hyperglycemia mouse blood sugar after compound, show that shown in formula I of the present invention, compound has obvious hypoglycemic activity.
Embodiment 6: the impact experiment on hyperuricemia mouse
Get 40 Kunming mouses and be divided at random 4 groups: Normal group, hyperuricemia model group, medicine control group (1,6,7-trihydroxy--3-methoxyl group xanthone-2-C-β-D-glucopyranoside), compound group shown in formula I (embodiment 1 preparation).0.5% Xylo-Mucine for test-compound (0.5%CMC-Na) is mixed with suspension, and gavage gives, every day 2 times, continuous 5 times.Mouse is 2h abdominal injection 400mg/kg Oxonic Acid sylvite before blood sampling, suppress uriKoxidase active, cause hyperuricemia mouse (Pathogenesis of Gout.Annals of Internal Medicine.2005,143 (7): 499-516.), Normal group is injected equal-volume 0.5%CMC-Na solution, after injection 1h, gavage is carried out last administration, after 2h, extract eyeball and get blood, the centrifugal 5min of 3000rpm, get serum, adopt enzymic colorimetric (Zhongsheng Beikong Biological Science & Technology Co., Ltd.'s test kit) to measure serum uric acid level, the results are shown in Table 3.
Table 3 is on the impact of hyperuricemia mouse (x ± s, n=10)
From table 3 result, after abdominal injection Oteracil Potassium, animal serum uric acid level significantly raises, hints model success.After gastric infusion 5 times, shown in formula I, compound group serum uric acid level is starkly lower than hyperuricemia model group, show that compound shown in formula I of the present invention can reduce the acute hyperuricemia mice serum uric acid level of Oteracil Potassium induction, has the effect of obvious inhibition hyperuricemia mice serum uric acid level.
Embodiment 7: containing the tablet of compound shown in formula I
The every tablet formulation containing the compound (1-hydroxy-3-methoxy-6, the tetra-acetylated glucopyranoside of 7-diacetoxy xanthone-2-C-β-D-) of 30mg embodiment 1 preparation forms:
Preparation method: after the compound of embodiment 1 preparation, starch, Microcrystalline Cellulose, sodium starch glycolate and Magnesium Stearate are mixed on tabletting machine compressing tablet, obtain every containing the tablet of the compound of 30mg embodiment 1 preparation, every heavy 300mg.
Embodiment 8: containing the capsule of compound shown in formula I
Every capsule forms containing the capsule formula of the compound (1-hydroxy-3-methoxy-6, the tetra-acetylated glucopyranoside of 7-diacetoxy xanthone-2-C-β-D-) of 30mg embodiment 1 preparation:
Preparation method: the compound of embodiment 1 preparation, dry starch, hydroxyl Starch Sodium and Magnesium Stearate are mixed, be packed in hard gelatin capsule with the amount of 30mg, obtain.
Embodiment 9: containing the injection liquid of compound shown in formula I
Every injection liquid formula containing the compound (1-hydroxy-3-methoxy-6, the tetra-acetylated glucopyranoside of 7-diacetoxy xanthone-2-C-β-D-) of 15mg embodiment 1 preparation forms:
Preparation method: the compound of embodiment 1 preparation is added to ethanol stirring and dissolving, with N.F,USP MANNITOL and appropriate water for injection, stir, add 0.1% pin activated carbon, absorption, filter decarburization, mend and inject water to specified amount, millipore filtration membrane filtration, by 1mL/, prop up embedding, 100 ℃ of moist heat sterilizations 20 minutes, qualified through lamp inspection, obtain.
Embodiment 10: containing the lyophilized injectable powder of compound shown in formula I
Every freeze-dried powder agent prescription containing the compound (1-hydroxy-3-methoxy-6, the tetra-acetylated glucopyranoside of 7-diacetoxy xanthone-2-C-β-D-) of 15mg embodiment 1 preparation forms:
Preparation method: in more than 100 grades workshop, the compound of embodiment 1 preparation is added to ethanol stirring and dissolving, add sodium-chlor, N.F,USP MANNITOL and appropriate water for injection, stir, add 0.1% pin activated carbon, absorption, filter decarburization, benefit injects water to specified amount, and millipore filtration membrane filtration, props up packing by 4mL/, lyophilize, encapsulation, through being up to the standards, obtains.
The explanation of above embodiment is just for helping to understand method of the present invention and core concept thereof.It should be pointed out that for those skilled in the art, under the premise without departing from the principles of the invention, can also carry out some improvement and modification to the present invention, these improvement and modification also fall in the protection domain of the claims in the present invention.
Claims (12)
1. a compound shown in formula I,
Wherein, Ac is ethanoyl.
2. a preparation method for compound shown in formula I, is characterized in that, under catalyst action, 1,6,7-trihydroxy--3-methoxyl group xanthone-2-C-β-D-glucopyranoside reacts and makes in solvent with diacetyl oxide.
3. preparation method according to claim 2, is characterized in that, described 1,6, and the mol ratio of 7-trihydroxy--3-methoxyl group xanthone-2-C-β-D-glucopyranoside and diacetyl oxide is 1.0:5.0～1.0:10.0.
4. preparation method according to claim 2, is characterized in that, described catalyzer is acetate.
5. preparation method according to claim 4, is characterized in that, described acetate is sodium acetate or potassium acetate.
6. preparation method according to claim 2, is characterized in that, described solvent is Glacial acetic acid.
7. preparation method according to claim 2, is characterized in that, described temperature of reaction is 40 ℃～70 ℃.
8. preparation method according to claim 2, is characterized in that, the described reaction times is 2h～5h.
9. described in claim 1, compound shown in formula I is being prepared antitumor drug, prevention or treatment diabetes medicament or is having the application regulating in blood uric acid function medicament.
10. a pharmaceutical composition, is characterized in that, comprises compound shown in formula I described in the claim 1 for the treatment of significant quantity.
11. 1 kinds of pharmaceutical preparations, is characterized in that, comprise compound and pharmaceutically acceptable auxiliary material shown in formula I described in the claim 1 for the treatment of significant quantity.
12. pharmaceutical preparations according to claim 1, is characterized in that, it is tablet, capsule, injection liquid or lyophilized injectable powder.
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Cited By (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN111533770A (en) * | 2020-05-14 | 2020-08-14 | 华侨大学 | Preparation method of arbutin in sparrow tea and application of arbutin in treating hyperuricemia |
| WO2022138735A1 (en) * | 2020-12-22 | 2022-06-30 | 学校法人近畿大学 | Pharmaceutical composition for ameliorating malignant diseases |
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|---|---|---|---|---|
| CN1733765A (en) * | 2005-08-18 | 2006-02-15 | 王刚 | Purple bergenia element pentaacetylate and its uses |
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Patent Citations (1)
| Publication number | Priority date | Publication date | Assignee | Title |
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| CN1733765A (en) * | 2005-08-18 | 2006-02-15 | 王刚 | Purple bergenia element pentaacetylate and its uses |
Non-Patent Citations (2)
| Title |
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| 李学坚等: "芒果苷酰化衍生物降血糖活性的研究", 《时珍国医国药》, vol. 24, no. 1, 23 January 2013 (2013-01-23), pages 51 - 53 * |
| 蓝萍等: "芒果苷及其衍生物对糖尿病小鼠的降糖作用", 《中国动物保健》, 30 June 2010 (2010-06-30), pages 21 - 22 * |
Cited By (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN111533770A (en) * | 2020-05-14 | 2020-08-14 | 华侨大学 | Preparation method of arbutin in sparrow tea and application of arbutin in treating hyperuricemia |
| WO2022138735A1 (en) * | 2020-12-22 | 2022-06-30 | 学校法人近畿大学 | Pharmaceutical composition for ameliorating malignant diseases |
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