CN116173159A - Zedoary turmeric oil sulfonate, and preparation method and application thereof - Google Patents
Zedoary turmeric oil sulfonate, and preparation method and application thereof Download PDFInfo
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- CN116173159A CN116173159A CN202111428977.XA CN202111428977A CN116173159A CN 116173159 A CN116173159 A CN 116173159A CN 202111428977 A CN202111428977 A CN 202111428977A CN 116173159 A CN116173159 A CN 116173159A
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- turmeric oil
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- oil sulfonate
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Images
Classifications
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K36/00—Medicinal preparations of undetermined constitution containing material from algae, lichens, fungi or plants, or derivatives thereof, e.g. traditional herbal medicines
- A61K36/18—Magnoliophyta (angiosperms)
- A61K36/88—Liliopsida (monocotyledons)
- A61K36/906—Zingiberaceae (Ginger family)
- A61K36/9066—Curcuma, e.g. common turmeric, East Indian arrowroot or mango ginger
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P35/00—Antineoplastic agents
-
- 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
Abstract
The invention discloses a zedoary turmeric oil sulfonate and a preparation method and application thereof, wherein the preparation method comprises the following steps: 1) The mass ratio is 1: (0.33-5): (0.01-0.1), dissolving zedoary turmeric oil, a sulfonating agent and peroxide in an ethanol water solution with the volume concentration of 50-95%, and stirring for 5-10 hours at the temperature of 25-80 ℃; 2) Extracting the product obtained in the step 1) with dichloromethane-water, recovering water, and concentrating under reduced pressure to obtain oily solid, namely zedoary turmeric oil sulfonate. The water solubility of the zedoary turmeric oil sulfonate is obviously enhanced compared with that of zedoary turmeric oil, the yield is high, and the preparation method is simple to operate. Experiments prove that the zedoary turmeric oil sulfonate has an inhibition effect on liver cancer cells.
Description
Technical Field
The invention belongs to the field of medicines, and relates to preparation and application of a zedoary turmeric oil sulfonate.
Background
Volatile oils are a volatile, water-immiscible, oily liquid that is widely found in plants [1,2] . Currently, the known volatile oil has 3000 kinds, 300 kinds of which have important commercial value and are widely applied to the industries of pharmacy, food, household, cosmetics and the like [1] . Modern pharmacological research shows that volatile oil has wide activities of anti-inflammatory, antibacterial, antiviral, antitumor and the like, is an important natural active substance, and has long application history in China and worldwide [1-3] . The main structural types are concentrated on terpenes, straight-chain compounds without any side chains, aromatic and phenolic compounds, and sulfur-containing derivatives [3,4] . Part of scholars consider that the volatile oil can simultaneously play antiviral, anti-inflammatory and immunoregulatory roles, is hopeful to become a potential medicine for treating COVID-19 and has important scientific value [5-7] 。
The main chemical components of the zedoary turmeric oil are terpenes including sesquiterpenes, monoterpenes and diterpenes; wherein the sesquiterpenes are the most abundant, and the content is more than 60% [8,9] Comprises Ji Ma alkanes, guaianes, elemenes, eucalyptol, etc [8 ,10 ,11] . The multiple monomer components have remarkable anti-inflammatory activity, such as furanodiene, curcumene, germacrone and curcumenol as main components, and have remarkable inhibitory activity on lipopolysaccharide-induced mouse macrophage release NO, and IC 50 6.5, 5.8, 9.4, 9.9. Mu.M respectively [12] The method comprises the steps of carrying out a first treatment on the surface of the IC with trace components such as wenyujin G and phaeoclausin A inhibiting NO generation 50 Also 7.6 and 8.5. Mu.M respectively [13,14] . In addition, beta-elemene can regulate transcription factor NF-kappa B, STAT3, thus inhibiting inflammation and tumor development [8] The method comprises the steps of carrying out a first treatment on the surface of the The curcumolide can be used for treating inflammatory diseases by inhibiting NF- κB and inflammatory factor production [15] The method comprises the steps of carrying out a first treatment on the surface of the The most deeply studied curcumenol can inactivate AP-1 through the dephosphorylation of JNK, thereby inhibiting Lipopolysaccharide (LPS) -induced inflammatory reaction and obviously reducing the expression of inflammatory mediators such as iNOS and the like [16] 。
However, volatile oil components are generally poorly water-soluble, rawPoor availability, generally contains double bond, hetero atom, chiral atom, etc., has active chemical property and is easy to decompose and lose pharmacological action [17,18-20] . For example, the solubility of curcumenol in water in curcuma oil is only 0.003mg/mL, and the bioavailability is not high [21] The method comprises the steps of carrying out a first treatment on the surface of the In addition, the zedoary turmeric oil has poor stability, and the main chemical substances thereof such as furanodiene, zedoary turmeric can react under high temperature condition such as cope rearrangement [22,23] Severely limiting its clinical application and development.
In order to improve the physicochemical properties such as the water solubility of volatile oil, various approaches have been explored. Firstly, modern preparation technology is utilized [27] If the polymer particle (polymeric particles) embedding technology is adopted, the method has larger loss of volatile oil; or encapsulation with liposomes (lipomes) and solid lipid nanoparticles (solid lipid nanoparticles), but this approach has limitations in drug carrying capacity and drug release [24] . Taking the injection of zedoary turmeric oil as an example, tween-80 is mainly used as a solubilizer to solve the problem of water solubility of the zedoary turmeric oil, but the stability of the injection is obviously reduced under the conditions of high temperature, high humidity and illumination; in addition, certain adverse reactions exist in clinical application, and the occurrence of the adverse reactions can be related to the solubilizer [25] The clinical application and popularization of the zedoary turmeric oil injection are severely restricted.
Another more widely used strategy is a structure-optimization strategy based on chemical synthesis. Structural optimization for the active ingredients of zedoary turmeric oil is currently mostly focused on curcumenol [21] The reaction sites are mainly double bonds and hydroxyl groups, such as Sun Hanjie, and the like, and the curcumenol is converted into the phosphate through 8-hydroxyl phosphorylation, so that the antitumor activity of the curcumenol is obviously enhanced; or double bonds are taken as reaction sites, and a plurality of active derivatives with better water solubility are obtained, which shows that the structure optimization strategy is one of the effective methods. However, at present, reports on optimization strategies of the overall structure of other active ingredients in the zedoary turmeric oil are not yet available.
Disclosure of Invention
The invention aims to overcome the defects of the prior art and provides a zedoary turmeric oil sulfonate.
The second object of the invention is to provide a preparation method of zedoary turmeric oil sulfonate.
The third object of the invention is to provide an application of zedoary turmeric oil sulfonate in preparing antitumor drugs.
The technical scheme of the invention is summarized as follows:
the preparation method of the zedoary turmeric oil sulfonate comprises the following steps:
1) The mass ratio is 1: (0.33-5): (0.01-0.1), dissolving zedoary turmeric oil, a sulfonating agent and peroxide in an ethanol water solution with the volume concentration of 50-95%, and stirring for 5-10 hours at the temperature of 25-80 ℃;
2) Extracting the product obtained in the step 1) with dichloromethane-water, recovering water, and concentrating under reduced pressure to obtain oily solid, namely zedoary turmeric oil sulfonate.
The sulphonating agent is preferably sodium metabisulphite, sodium bisulphite, sodium sulphite, chlorosulphonic acid or sulphuric acid.
The peroxide is preferably tert-butyl peroxybenzoate, benzoyl peroxide, hydrogen peroxide, dibenzoyl peroxide, peracetic acid or tert-amyl peroxyneodecanoate.
The zedoary turmeric oil sulfonate prepared by the preparation method.
The application of the zedoary turmeric oil sulfonate in preparing antitumor drugs.
The invention has the advantages that:
1) The water solubility of the zedoary turmeric oil sulfonate is obviously enhanced compared with that of zedoary turmeric oil, the yield is high, and the preparation method is simple to operate.
2) Experiments prove that the zedoary turmeric oil sulfonate has an inhibition effect on liver cancer cells.
Drawings
Figure 1 HPLC characteristic diagram of zedoary turmeric oil sulfonate.
Figure 2 shows the cytotoxic activity of zedoary turmeric oil sulfonate against human liver cancer cells (Huh-7) (n=4, compared with the control group, significance p < 0.01).
Detailed Description
The zedoary turmeric oil used in the invention is obtained according to the preparation method specified in Chinese pharmacopoeia of 2020 edition, and is volatile oil extracted from zedoary turmeric (Curcuma zedoaria) by steam distillation.
The following described embodiments are some, but not all, examples of the present invention and are merely illustrative of the present invention and should not be construed as limiting the scope of the invention. All other embodiments, which can be made by those skilled in the art based on the embodiments of the invention without making any inventive effort, are intended to be within the scope of the invention. The specific conditions are not noted in the examples and are carried out according to conventional conditions or conditions recommended by the manufacturer. The reagents or apparatus used were conventional products commercially available without the manufacturer's attention.
The reaction formula of the preparation method of the zedoary turmeric oil sulfonate is as follows:
example 1
The preparation method of the zedoary turmeric oil sulfonate comprises the following steps:
1) 10.0g of zedoary turmeric oil, 14.3g of sodium metabisulfite (sulphonating reagent) and 0.77g of tert-butyl peroxybenzoate (peroxide) are taken and dissolved in 300mL of ethanol water solution with volume concentration of 75%, and stirred for 8 hours at 75 ℃;
2) The product obtained in step 1) was extracted with methylene chloride-water, the water fraction was recovered, and concentrated under reduced pressure to obtain an oily solid, namely zedoary turmeric oil sulfonate (7.45 g).
Example 2
The preparation method of the zedoary turmeric oil sulfonate comprises the following steps:
1) 10.0g of zedoary turmeric oil, 3.3g of sodium bisulphite (sulphonation reagent) and 0.1g of benzoyl peroxide (peroxide) are taken and dissolved in 300mL of 50% ethanol water solution by volume concentration, and stirred for 10 hours at 25 ℃;
2) The product obtained in the step 1) is extracted with dichloromethane-water, the water part is recovered, and the oily solid, namely zedoary turmeric oil sulfonate (3.27 g) is obtained by vacuum concentration.
Example 3
The preparation method of the zedoary turmeric oil sulfonate comprises the following steps:
1) 10g of zedoary turmeric oil, 50g of sodium sulfite (sulfonating agent) and 1g of hydrogen peroxide (peroxide) are taken and dissolved in 300mL of ethanol water solution with volume concentration of 95%, and stirred for 5 hours at 80 ℃;
2) The product obtained in the step 1) is extracted with dichloromethane-water, the water part is recovered, and the oily solid, namely zedoary turmeric oil sulfonate (5.38 g) is obtained by vacuum concentration.
Experiments prove that the zedoary turmeric oil sulfonate is prepared by using chlorosulfonic acid or sulfuric acid to replace sodium sulfite in the embodiment, and using dibenzoyl peroxide, peracetic acid or tert-amyl peroxyneodecanoate to replace the peroxide in the embodiment.
EXAMPLE 4 solubility of zedoary turmeric oil in comparison with the sulfonate of zedoary turmeric oil prepared in different examples
Under normal temperature and pressure, 10.0mL of deionized water is taken and placed in a shaking flask, 10mg of zedoary turmeric oil is added, and after shaking for 10min, standing is carried out for 30min, and whether insoluble substances exist or not is observed. In the same way, under the condition of normal temperature and normal pressure, 10.0mL of deionized water is taken in a shaking flask, 500mg of zedoary turmeric oil sulfonate is added, shaking is carried out for 10min, then standing is carried out for 30min, and whether insoluble substances exist or not is observed. The solubility of the zedoary turmeric oil sulfonate of examples 1-3 was determined, table 1. The test results show that the water solubility of the zedoary turmeric oil is less than 1mg/ml, and the water solubility of the zedoary turmeric oil sulfonate prepared in the examples 1-3 is more than 50mg/ml, so that the water solubility of the zedoary turmeric oil sulfonate is obviously enhanced compared with the water solubility of the zedoary turmeric oil.
Table 1 solubility test results
EXAMPLE 5 HPLC characteristic spectrum establishment of zedoary turmeric oil sulfonate
The zedoary turmeric oil sulfonate obtained in example 1 was prepared into an aqueous solution with a concentration of 10mg/ml, and then treated in YMC-triert C 18 ExRS chromatographic column (model 250X 4.6mm I.D., S-5 μm,8 nm), detection wavelength 216nm, column temperature 30 ℃, flow rate 1ml/min, acetonitrile-water gradient elution (as in Table 1)Under the condition, a 216nm absorption spectrum of the zedoary turmeric oil sulfonate with the following HPLC characteristics is established for qualitative characterization of the zedoary turmeric oil sulfonate, and the qualitative characterization is shown in figure 1.
TABLE 2 HPLC elution gradient of zedoary turmeric oil sulfonate
EXAMPLE 6 evaluation of anti-liver cancer Activity of zedoary turmeric oil sulfonate and its fractions
The zedoary turmeric oil sulfonate prepared in example 1 was subjected to MCI resin (model GEL CHP 20P) with a volume concentration of 0%,5%,10% ethanol-water gradient elution, and the 0%,5%,10% ethanol-water eluted fractions were collected, respectively, to obtain zedoary turmeric oil sulfonate components S1, S2 and S3.
Human hepatoma cells (Huh-7, commercially available) were cultured in RRMI1640 medium containing 10% fetal bovine serum and 100U/ml penicillin at 37deg.C with 5% CO 2 Subculturing in a saturated humidity incubator. Taking logarithmic growth phase cells, digesting, fully blowing into single cell suspension, counting, and diluting to 1×10 4 cell/ml, inoculated in 96-well culture plate, 100. Mu.L/well. After the cells adhere to the wall, zedoary turmeric oil sulfonate and components S1, S2 and S3 are respectively added. Each sample was set to a low and high concentration level of 2 (10. Mu.g/mL and 50. Mu.g/mL, respectively) and 4 parallel wells were set for each concentration level. An equal volume of physiological saline was added to the control group. 96-well plates were placed at 37℃in 5% CO 2 After 96 hours of incubation in a saturated humidity incubator, each well was incubated after addition of CCK-8 according to the instructions of CCK-8 kit, and the optical density at 450nm was measured on a BIORAD 550-type microplate reader, see FIG. 2. The result shows that the zedoary turmeric oil sulfonate can obviously inhibit the growth of Huh-7 human liver cancer cells (P) at the concentration of 50 mug/mL<0.01). While S3 in the zedoary turmeric oil sulfonate component has remarkable inhibition activity (P) on the growth of Huh-7 human liver cancer cells at the concentration of 50 mug/mL< 0.01)。
Experiments prove that 50 mug/mL of the zedoary turmeric oil sulfonate prepared in the example 2 and the example 3 has similar activity on inhibiting the growth of human liver cancer cells (Huh-7) as that of the zedoary turmeric oil sulfonate prepared in the example 1.
The zedoary turmeric oil sulfonate is used as raw material, and is prepared into tablets, capsules, dripping pills, aerosols, pills, powders, solutions, suspensions, emulsions, granules, suppositories, freeze-dried powder injection and the like by adopting conventional technical means. The route of administration may be enteral or parenteral, such as oral, intramuscular, subcutaneous, nasal, oral, dermal, peritoneal or rectal, and the like, preferably oral. If desired, the active ingredient of the present invention may be combined with one or more solid or liquid pharmaceutical excipients and/or adjuvants, in a suitable form or dosage form for use as a human or veterinary drug.
Reference to the literature
[1].Baptista-Silva S.；Borges S.；Ramos O.L.,et al.The progress of essential oils as potential therapeutic agents: a review.Journal of Essential Oil Research.2020,32(4):279–295.
[2] Once the best is constant; zhong Lingyun; cheng Lijia pharmaceutical plant volatile oil pharmacological activity and clinical application research progress, pharmaceutical information 2020,9 (6): 204-210.
[3].Baser K.H.C.；Buchbauer G.Handbook of essential oils:science,technology,and applications(3rd edition). New York:CRC Press.2020:37–42.
[4].Wani A.R.；Yadav K.；Khursheed A.,et al.An updated and comprehensive review of the antiviral potential of essential oils and their chemical constituents with special focus on their mechanism of action against various influenza and coronaviruses.Microbial Pathogenesis.2021,152:104620.
[5].Asif M.；Saleem M.；Saadullah,M.,et al.COVID-19and therapy with essential oils having antiviral, anti-inflammatory,and immunomodulatory properties.Inflammopharmacol.2020,28:1153–1161.
[6].Wilkin P.J.；Al-Yozbaki M.；George A.,et al.The undiscovered potential of essential oils for treating SARS-CoV-2(COVID-19).Current Pharmaceutical Design.2020,26(41):5261–5277.
[7].Boukhatem M.N.；Setzer W.N.Aromatic herbs,medicinal plant-derived essential oils,and phytochemical extracts as potential therapies for coronaviruses:future perspectives.Plants.2020,9(6):800.
[8] Liu Mei; guo Xiaogong; sun Quandeng the chemical composition and pharmacological action of Curcuma wenyujin was developed modern medicine and clinic 2021,36 (1): 204-208.
[9] Zhang Shihui; liu Dan; zhou Yakui GC-Q/TOF-MS analysis of the zedoary turmeric oil fractions under different extraction methods, nandina Pharmacopeia 2020, 18 (11): 1879-1887.
[10].Noura S.D.；William N.S.Chemical composition and biological activities of essential oils of curcuma species.Nutrients.2018,10:1196.
[11].Zhou Y.；Xie M.；Song Y.,et al.Two traditional Chinese medicines Curcumae radix and Curcumae rhizoma: an ethnopharmacology,phytochemistry,and pharmacology review.Evidence-Based Complementary and Alternative Medicine.2016:article ID 4973128.
[12] Wang Shan; zheng Yanping; sun Xiuyan the inhibition of lipopolysaccharide-activated macrophages to nitric oxide, university of smoke desk (Nature science and engineering edition) 2008,21 (1): 71-74.
[13].Yin G.；Li L.；Zhang Q.,et al.iNOS inhibitory activity of sesquiterpenoids and a monoterpenoid from the rhizomes of Curcuma wenyujin.Journal of Natural Products.2014,77(10):2161–2169.
[14].Qiu G.；Yan P.；Shao W.,et al.Two new sesquiterpenoids including a sesquiterpenoid lactam from Curcuma wenyujin.Chemical and Pharmaceutical Bulletin.2013,61(9):983–986.
[15].Dong J.；Shao W.；Yan P.,et al.Curcumolide,a unique sesquiterpenoid with anti-inflammatory properties from Curcuma wenyujin.Bioorganic&Medicinal Chemistry Letters.2015,25(2):198–202.
[16].Chen X.；,Zong C.；Gao Y.,et al.Curcumol exhibits anti-inflammatory properties by interfering with the JNK-mediated AP-1pathway in lipopolysaccharide-activated RAW264.7 cells.European Journal of Pharmacology.2014,723:339–345.
[17] Li Yao; wu Jianhua; xie Yanhua the research of zedoary turmeric oil, university of Shaanxi, journal of traditional Chinese medicine, 2017,40 (3): 118-121.
[18] Yu Fen; mo Na; wu Zhenfeng the research of decompression extraction and its combined technology in volatile oil of Chinese medicine, 2020,51 (13) is 3561-3566.
[19].Khayyat S.A.；Roselin L.S.Recent progress in photochemical reaction on main components of some essential oils.Journal of Saudi Chemical Society.2018,22(7):855–875.
[20].Turek C.；Stintzing F.C.Stability of essential oils:a review.Comprehensive Reviewsin Food Science and Food Safety.2013,12(1):40–53.
[21] Adding feelings; meng Xiangwei; the anti-tumor activity of curcumenol and its derivatives is developed in the morning, etc., chinese herbal medicine 2020,51 (21): 5613-5621.
[22].Suphrom N.；Srivilai J.；Pumthong G.,et al.Stability studies of antiandrogenic compounds in Curcuma aeruginosa Roxb.extract.Journal of Pharmacy and Pharmacology.2014,66(9):1282–1293.
[23] Li Wenting; zhou Ming; chen Bilian HPLC is used for simultaneously measuring 6 sesquiterpene components in zedoary turmeric oil, journal of Chinese experimental prescription, 2011, 17 (20): 48-52.
[24] Song Chunxiao; he Shulian; cao Chunfeng solid lipid nanoparticles and nanostructured lipid carriers have been developed for drug delivery pharmaceutical research 2016,35 (4): 234-245.
[25] Normally rainbow; wu Shifu; li Yuji, et al, 737 examples of curcuma zedoary turmeric oil injection adverse reaction analysis and literature review, chinese medicine alert, 2017,14 (6): 359-363.
Claims (5)
1. The preparation method of the zedoary turmeric oil sulfonate is characterized by comprising the following steps:
1) The mass ratio is 1: (0.33-5): (0.01-0.1), dissolving zedoary turmeric oil, a sulfonating agent and peroxide in an ethanol water solution with the volume concentration of 50-95%, and stirring for 5-10 hours at the temperature of 25-80 ℃;
2) Extracting the product obtained in the step 1) with dichloromethane-water, recovering water, and concentrating under reduced pressure to obtain oily solid, namely zedoary turmeric oil sulfonate.
2. The method according to claim 1, wherein the sulfonating agent is sodium metabisulfite, sodium bisulfite, sodium sulfite, chlorosulfonic acid or sulfuric acid.
3. The process according to claim 1, wherein the peroxide is t-butyl peroxybenzoate, benzoyl peroxide, hydrogen peroxide, dibenzoyl peroxide, peracetic acid or t-amyl peroxyneodecanoate.
4. Zedoary turmeric oil sulfonate prepared by the preparation method of one of claims 1 to 3.
5. The use of the zedoary turmeric oil sulfonate of claim 4 in the preparation of antitumor drugs.
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Citations (9)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US20070191360A1 (en) * | 2004-05-26 | 2007-08-16 | Hangzhou Minsheng Pharmaceuticals Co., Ltd. | Curcumol derivatives, the compositions containing the said derivatives, and the use of the same in the manufacture of medicaments |
| CN101347597A (en) * | 2007-07-20 | 2009-01-21 | 天津天士力制药股份有限公司 | Effective component of turmeric rhizome and preparation method and use thereof |
| US20090326275A1 (en) * | 2008-06-27 | 2009-12-31 | Dimauro Thomas M | Use of nitrogen-containing curcumin analogs for the treatment of alzheimers disease |
| WO2010012131A1 (en) * | 2008-07-28 | 2010-02-04 | Chen Rong | The usage of medicinal composition containing oil of zedoary turmeric in manufacture of medicaments |
| CN102716114A (en) * | 2012-07-13 | 2012-10-10 | 海南碧凯药业有限公司 | Pharmaceutical composition comprising germacron, curzerene and borneol |
| CN103127051A (en) * | 2011-11-24 | 2013-06-05 | 复旦大学 | Application of curcumenol in anti-tumor drug preparation |
| CN106632383A (en) * | 2016-11-21 | 2017-05-10 | 辽宁大学 | Curcumenol derivative as well as preparation method and application thereof in antitumor drugs |
| CN107308133A (en) * | 2016-04-27 | 2017-11-03 | 周意 | Curcumin pharmaceutical preparation |
| CN110755580A (en) * | 2019-12-04 | 2020-02-07 | 北京中医药大学东直门医院 | Traditional Chinese medicine composition with analgesic effect and application thereof |
-
2021
- 2021-11-28 CN CN202111428977.XA patent/CN116173159B/en active Active
Patent Citations (9)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US20070191360A1 (en) * | 2004-05-26 | 2007-08-16 | Hangzhou Minsheng Pharmaceuticals Co., Ltd. | Curcumol derivatives, the compositions containing the said derivatives, and the use of the same in the manufacture of medicaments |
| CN101347597A (en) * | 2007-07-20 | 2009-01-21 | 天津天士力制药股份有限公司 | Effective component of turmeric rhizome and preparation method and use thereof |
| US20090326275A1 (en) * | 2008-06-27 | 2009-12-31 | Dimauro Thomas M | Use of nitrogen-containing curcumin analogs for the treatment of alzheimers disease |
| WO2010012131A1 (en) * | 2008-07-28 | 2010-02-04 | Chen Rong | The usage of medicinal composition containing oil of zedoary turmeric in manufacture of medicaments |
| CN103127051A (en) * | 2011-11-24 | 2013-06-05 | 复旦大学 | Application of curcumenol in anti-tumor drug preparation |
| CN102716114A (en) * | 2012-07-13 | 2012-10-10 | 海南碧凯药业有限公司 | Pharmaceutical composition comprising germacron, curzerene and borneol |
| CN107308133A (en) * | 2016-04-27 | 2017-11-03 | 周意 | Curcumin pharmaceutical preparation |
| CN106632383A (en) * | 2016-11-21 | 2017-05-10 | 辽宁大学 | Curcumenol derivative as well as preparation method and application thereof in antitumor drugs |
| CN110755580A (en) * | 2019-12-04 | 2020-02-07 | 北京中医药大学东直门医院 | Traditional Chinese medicine composition with analgesic effect and application thereof |
Non-Patent Citations (3)
| Title |
|---|
| 寇雪莹;等: "混合表面活性剂对姜黄素的增溶作用", 山东理工大学学报(自然科学版), vol. 24, no. 3, pages 6 - 9 * |
| 张海静;等: "黄芪多糖对大鼠急性放射性肺损伤的治疗作用", 中国生化药物杂志, vol. 35, no. 9, pages 8 - 11 * |
| 陈诗琪；等: "中药注射剂临床应用存在问题及说明书的相关思考与建议", vol. 20, no. 10, pages 1718 - 1722 * |
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