CN111228253B - Application of amomum kravanh extract in preparation of alpha-glucosidase inhibitor medicine - Google Patents
Application of amomum kravanh extract in preparation of alpha-glucosidase inhibitor medicine Download PDFInfo
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- CN111228253B CN111228253B CN202010176319.5A CN202010176319A CN111228253B CN 111228253 B CN111228253 B CN 111228253B CN 202010176319 A CN202010176319 A CN 202010176319A CN 111228253 B CN111228253 B CN 111228253B
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- glucosidase inhibitor
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Abstract
The invention relates to the field of medical chemistry, in particular to application of a galangal seed extract in preparation of an alpha-glucosidase inhibitor drug. The compound of the formula I is extracted and separated from the complex chemical components of the amomum kravanh, and can obviously inhibit the activity of alpha-glucosidase.
Description
Technical Field
The invention relates to the field of medical chemistry, in particular to application of a galangal seed extract in preparation of an alpha-glucosidase inhibitor drug.
Background
Alpha-glucosidase mainly comprises enzymes such as maltase, sucrase, maltase, lactase and the like, is widely distributed in brush borders of villous mucosa cells of small intestine of an organism, participates in a plurality of biological processes such as digestion of food of the organism, biosynthesis of glycoprotein, synthesis and catabolism of polysaccharide and glycoconjugates and the like, and is a general name of enzymes which can catalyze and hydrolyze alpha-glucosyl from a non-reducing end containing alpha-glucosidic bond substrates.
Alpha-glucosidase affects the formation of complex carbohydrate on cell surface, and diseases such as diabetes, obesity, hyperlipidemia, inflammation, canceration, immune response and virus infection are closely related to the formation of complex carbohydrate on cell surface, so that the alpha-glucosidase inhibitor not only has clinical application value for sugar metabolism disorder diseases such as diabetes, obesity and the like, but also can be used as potential therapeutic agent for resisting AIDS virus and murine leukemia virus.
Alpinia zerumbet (Amomum maximum Roxb) is a perennial herb of the genus Amomum of the family Zingiberaceae, also known as Amomum zerumbet, Nibea japonica, Guogu, etc., and is mainly distributed in tropical regions of south to southeast Asia. The fruits and roots have medicinal value, can stimulate appetite, promote digestion, promote qi circulation and relieve pain, are often used for treating digestive system diseases, and flowers, fruits, tender stems and the like can be eaten as wild vegetables. However, no studies have reported the effect of certain specific components in the extract of Elettaria galanga on alpha-glucosidase.
Disclosure of Invention
The present invention is directed to solving at least one of the problems of the prior art. The invention provides an application of a amomum kravanh extract in preparing an alpha-glucosidase inhibitor medicament.
The technical scheme of the invention is as follows:
the invention provides an application of a compound shown in a formula I or a pharmaceutically acceptable salt thereof in preparing an alpha-glucosidase inhibitor drug,
the compound shown in the formula I belongs to a labdane diterpenoid compound, the labdane (labdane) diterpenoid is bicyclic diterpenoid, the structure of the compound takes decahydronaphthalene as a mother nucleus, and an A/B ring is cis-fused. Some common labdane diterpenoid compounds are important components of common medicines in folk, and often have the effects of treating stomach diseases, resisting inflammation, resisting bacteria, relieving pain, killing insects and the like, and further research reports that some of the compounds also have other pharmacological activities of resisting tumors and cell toxicity, treating leukocytosis, platelet activating factor inhibitors and the like. Because the substituent has obvious influence on the activity of the compounds, the research on the relation between the substituent and the pharmacological action of the compounds is not thorough at present, and the inventor discovers the new application of the compound shown in the formula I through a great deal of scientific research and can obviously inhibit the alpha-glucosidase.
According to some embodiments of the invention, the compound of formula I is extracted from alpinia katsumadai.
The compound of the formula I is extracted and separated from the rhizome of the aspongopus, the chemical components of the aspongopus are complicated and comprise flavonoid, diterpene, diphenhydraptane, triterpene, phenylpropanoid and other substances, and the compound of the formula I with the obvious alpha-glucosidase inhibition activity is separated from a large amount of active components of the aspongopus by the inventor.
According to some embodiments of the invention, the compound of formula I is isolated from an alcohol extract of alpinia katsumadai.
According to some embodiments of the invention, the alcohol extract may be a methanol extract or an ethanol extract.
According to some embodiments of the invention, the compound of formula I is isolated from an ethanol extract of alpinia katsumadai.
The semen Alpiniae Katsumadai can be extracted with various solvents, such as pure water, methanol, ethanol, petroleum ether, etc., preferably with ethanol. In one embodiment, the compound of formula I is isolated from an ethanol extract of Alpinia zerumbet.
According to some embodiments of the invention, the method of preparing the compound of formula I comprises: pulverizing root and stem of Alpinia zerumbet, reflux-extracting with ethanol to obtain extractive solution, concentrating under reduced pressure until no ethanol smell is observed, extracting with ethyl acetate, and separating and purifying by silica gel column chromatography and sephadex column chromatography.
According to some embodiments of the invention, the ethanol is 95% ethanol.
According to some embodiments of the invention, the silica gel column chromatography is performed by gradient elution with petroleum ether-acetone and dichloromethane-methanol.
According to some embodiments of the invention, the sephadex column is eluted with dichloromethane-methanol.
According to some embodiments of the invention, the alpha-glucosidase inhibitor is a medicament and/or nutraceutical for the treatment of diabetes.
According to some embodiments of the invention, the α -glucosidase inhibitor is a medicament for treating aids.
The alpha-glucosidase inhibitor (AGI) can reversibly compete for the alpha-glucosidase at the brush border of villous mucosa cells of small intestine, inhibit the decomposition of carbohydrate, reduce the generation and absorption of glucose, slow the rise of postprandial blood sugar, reduce the stimulation of blood sugar to pancreas, protect the function of pancreas and effectively improve the occurrence and development of complications caused by hyperglycemia. In addition, the alpha-glucosidase inhibitor has no obvious toxic or side effect on liver and kidney functions. At present, alpha-glucosidase inhibitors have been widely used to reduce postprandial hyperglycemia and have been considered as the main therapeutic drugs for type II diabetes. Because alpha-glucosidase can also affect the formation of complex carbohydrates on the cell surface, and diseases such as diabetes, obesity, hyperlipidemia, inflammation, canceration, immune response and virus infection are closely related to the formation of complex carbohydrates on the cell surface, the alpha-glucosidase inhibitor can also be used for treating diseases related to the complex carbohydrates on the cell surface.
The invention also provides application of the composition in preparing alpha-glucosidase inhibitor drugs, wherein the composition comprises the compound shown in the formula I or pharmaceutically acceptable salts thereof.
According to some embodiments of the invention, the composition further comprises a pharmaceutical excipient. The pharmaceutic adjuvant is a conventional pharmaceutic carrier in the field, and can be any suitable physiologically or pharmaceutically acceptable pharmaceutic adjuvant; preferably, a pharmaceutically acceptable disintegrant, diluent, lubricant, binder, wetting agent, flavoring agent, or preservative is included. The disintegrating agent can be corn starch, potato starch, cross-linked polyvinylpyrrolidone, sodium carboxymethyl starch, low-substituted hydroxypropyl cellulose, cross-linked sodium carboxymethyl cellulose, calcium carboxymethyl cellulose, or alginic acid. The diluent may be lactose, sucrose, mannitol, corn starch, potato starch, calcium phosphate, calcium citrate or crystalline cellulose. The lubricant can be superfine silica gel powder, magnesium stearate, calcium stearate, stearic acid, talcum powder or anhydrous silica gel. The binder may be acacia, gelatin, dextrin, hydroxypropyl cellulose, methyl cellulose or polyvinylpyrrolidone. The wetting agent may be sodium lauryl sulfate. The flavoring agent may be aspartame, stevioside, sucrose, maltitol or citric acid. The preservative may be methyl paraben or propyl paraben.
According to some embodiments of the present invention, the composition is in various dosage forms conventional in the art, preferably in solid, semi-solid or liquid form, and may be an aqueous solution, non-aqueous solution or suspension, more preferably a tablet, capsule, soft capsule, granule, pill or oral liquid.
According to some embodiments of the invention, the composition may be administered orally.
The term "pharmaceutically acceptable salt" as used herein means a salt of a compound of the invention which is pharmaceutically acceptable and which possesses the desired pharmacological activity of the parent compound. Such salts include: acid addition salts with inorganic acids such as hydrochloric acid, hydrobromic acid, sulfuric acid, nitric acid, phosphoric acid, and the like, or with organic acids; such as acetic acid, propionic acid, hexanoic acid, cyclopentanepropionic acid, glycolic acid, pyruvic acid, lactic acid, malonic acid, succinic acid, malic acid, maleic acid, fumaric acid, tartaric acid, citric acid, benzoic acid, cinnamic acid, mandelic acid, methanesulfonic acid, ethanesulfonic acid, benzenesulfonic acid, naphthalenesulfonic acid, camphorsulfonic acid, glucoheptonic acid, gluconic acid, glutamic acid, hydroxynaphthoic acid, salicylic acid, stearic acid, muconic acid, and the like; or salts formed when an acidic proton present on the parent compound is replaced by a metal ion, e.g., an alkali metal ion or an alkaline earth metal ion; or a complex compound with an organic base such as ethanolamine, diethanolamine, triethanolamine, N-methylglucamine, or the like.
The invention has the beneficial effects that:
the compound of the formula I is extracted and separated from the complex chemical components of the amomum kravanh, and can obviously inhibit the activity of alpha-glucosidase.
Drawings
FIG. 1 is a liquid chromatogram of a middle distillate.
Detailed Description
The technical solutions of the present invention are further described below with reference to specific examples, but the present invention is not limited to these specific embodiments. The test methods used in the examples are all conventional methods unless otherwise specified; the materials, reagents and the like used are commercially available reagents and materials unless otherwise specified.
EXAMPLE 1 preparation of Compounds of formula I
Pulverizing dried rhizome of Alpinia zerumbet 2 kg, extracting with 5L 95% ethanol under reflux for three times, mixing extractive solutions, concentrating under reduced pressure until no alcohol smell exists, adding pure water to total volume of 1L, extracting with equal volume of ethyl acetate for three times, mixing ethyl acetate extractive solutions, and concentrating under reduced pressure to dry.
The ethyl acetate extract was subjected to silica gel column chromatography and eluted with a petroleum ether-acetone gradient. Collecting petroleum ether-acetone 9: 1, eluting the fraction, and recovering the fraction to be dry under reduced pressure. Performing silica gel column chromatography, performing dichloromethane-methanol gradient elution, and collecting 98: 2, eluting a fraction, separating the fraction by using preparative liquid chromatography, as shown in fig. 1, wherein the liquid chromatogram of the fraction is shown, and the mobile phase is methanol-water 85: and 15, the flow rate is 6ml/min, the chromatographic column is an RP-C18 chromatographic column (10 x 250mm), the detection wavelength is set to be 280nm, and chromatographic peaks with the retention time of 18.5-20.0min are collected. Performing Sephadex LH-20 gel column chromatography, and performing dichloromethane-methanol 1: 1 to give the compound of formula I.
EXAMPLE 2 preparation of Compounds of formula I
Pulverizing dried root and stem of Alpinia zerumbet 2 kg, percolating with 20L 95% ethanol, mixing the alcoholic extracts, concentrating under reduced pressure to about 2L, and adding 500 g pretreated macroporous resin (resin type can be D101, AB-8, HPD-100 and HP 20). Evaporating to remove ethanol, loading into column, performing gradient elution with ethanol-water (0, 30%, 60%, 80% and 95% ethanol), collecting 80% ethanol eluate as target fraction, and concentrating under reduced pressure to dry; performing silica gel column chromatography and dichloromethane-methanol gradient elution, and collecting 98: 2 elution fraction, which is separated by preparative liquid chromatography, with mobile phase methanol-water 85: 15, flow rate 6ml/min, RP-C18 column (10 x 250mm), detection wavelength set to 280nm, collection retention time of 18.5-20.0min chromatographic peak. Performing Sephadex LH-20 gel column chromatography, and performing dichloromethane-methanol 1: 1 to give the compound of formula I.
EXAMPLE 3 structural characterization of Compounds of formula I
The structure of the compound of formula I is determined by nuclear magnetic resonance spectrum and mass spectrum analysis.
The carbon spectrum and hydrogen spectrum data are as follows:
1H-NMR(600MHz,CDCl3)δ7.67(d,J＝6.0Hz,1H),7.56(s,1H),6.33(d,J＝6.0Hz,1H),4.82(s,1H),4.64(s,1H),2.69(d,J＝16.2Hz,1H),2.45(dd,J＝11.4,16.2Hz,1H),2.40-2.36(m,1H),2.04-1.95(m,2H),1.89-1.85(m,1H),1.78-1.73(m,1H),1.64-1.56(tq,J＝3.0,13.8Hz,1H),1.55-1.48(m,1H),1.43-1.38(m,1H),1.37-1.32(dq,J＝4.2,12.6Hz,1H),1.24-1.15(m,3H),0.88(s,3H),0.82(s,3H),0.78(s,3H).
13C-NMR(150MHz,CDCl3)δ178.70(-CO-,C-13),154.61(＝CH-,C-15),152.99(＝CH-,C-16),147.70(C,C-8),129.85(C,C-12),116.36(＝CH-,C-14),107.77(＝CH-,C-17),55.54(CH,C-5),53.96(CH,C-9),42.06(CH2,C-3),39.98(C,C-10),39.01(CH2,C-1),38.07(CH2,C-7),33.63(CH3,C-18),33.63(C,C-4),24.37(CH2,C-6),21.72(CH3,C-19),19.54(CH2,C-11),19.36(CH2,C-2),14.37(CH3,C-20).
EXAMPLE 4 inhibition of alpha-glucosidase by Compounds of formula I
Mixing 100 μ l sample solution (the compound of formula I is dissolved in DMSO and then diluted to 100, 50, 25, 12.5 and 6.25 μ g/ml with 100mM, pH6.8 phosphate buffer solution, and the DMSO content is controlled to be lower than 5%) with 300 μ l α -glucosidase solution (0.1U/ml, dissolved in phosphate buffer solution), and incubating in 37 deg.C water bath for 20 min; adding 900 μ l substrate p-NPG solution (5mM, dissolved in phosphate buffer), mixing, and further incubating in 37 deg.C water bath for 15 min; 3000. mu.l of sodium carbonate solution (1M) was added to terminate the reaction; the absorbance value of the reaction system at a wavelength of 405nm was measured using an ultraviolet-visible spectrophotometer (A)s) (ii) a Meanwhile, an equal volume of phosphate buffer solution was used as a control group instead of the alpha-glucosidase solution (A)s0) The sample solution was replaced by an equal volume of phosphate buffer as a blank (A)0) The inhibition rate of the samples on alpha-glucosidase was calculated according to the following formula, and all experiments were repeated three times. The half Inhibitory Concentration (IC) of the samples on alpha-glucosidase was calculated using SPSS software50Value).
In order to more intuitively show the inhibition effect of the compound shown in the formula I on alpha-glucosidase, acarbose is used as a positive control, the test is carried out according to the steps, and the half inhibition concentration (I C) of the acarbose on the alpha-glucosidase is calculated50Value).
In the research, the inventor also found that the substituent of the labdane diterpenoid compound has a remarkable influence on the activity of the compound, other labdane diterpenoid compounds (formula II: amoxanthin A and formula III: coronarin D) are tested according to the steps described above,and calculating the half Inhibitory Concentration (IC) of the alpha-glucosidase50Value).
As shown in Table 1, it can be seen that the IC of the compound of formula I for alpha-glucosidase50The value (mu g/ml) is 18.64 +/-0.94, and the compound has obvious inhibition effect, and the action intensity is equivalent to that of the positive control drug acarbose (P)>0.05). Other labdane diterpene compounds (amoxanthin A and coronarin D) have no inhibition effect on alpha-glucosidase.
TABLE 1 inhibition of alpha-glucosidase by different compounds
Note:#indicates P > 0.05 compared to the positive control acarbose group.
It will be appreciated by those skilled in the art that the use of the present invention is not limited to the specific applications described above. The invention is also not limited to the preferred embodiments thereof with respect to the specific elements and/or features described or depicted herein. It should be understood that the invention is not limited to the disclosed embodiment or embodiments, but is capable of numerous rearrangements, modifications and substitutions without departing from the scope of the invention as set forth and defined by the following claims.
Claims (8)
1. The application of the compound shown in the formula I in the preparation of alpha-glucosidase inhibitor drugs, wherein the alpha-glucosidase inhibitor drugs are drugs for treating diabetes,
（I）。
2. the use as claimed in claim 1, wherein the compound of formula I is extracted from alpinia katsumadai.
3. The use as claimed in claim 2, wherein the compound of formula I is isolated from an alcoholic extract of alpinia katsumadai.
4. Use according to any one of claims 1 to 3, characterized in that the compound of formula I is prepared by a process comprising: pulverizing root and stem of Alpinia zerumbet, reflux-extracting with ethanol to obtain extractive solution, concentrating under reduced pressure until no ethanol smell is observed, extracting with ethyl acetate, and separating and purifying by silica gel chromatography and sephadex column.
5. The use according to claim 4, wherein the silica gel column is eluted with a petroleum ether-acetone and dichloromethane-methanol gradient.
6. Use according to claim 4, characterized in that it is eluted with dichloromethane-methanol when passing through a sephadex column.
7. Use of a composition comprising a compound of formula I according to any one of claims 1 to 3 for the preparation of a medicament of an α -glucosidase inhibitor, wherein the medicament of an α -glucosidase inhibitor is a medicament for the treatment of diabetes.
8. The use of claim 7, wherein the composition further comprises a pharmaceutical excipient selected from at least one of a pharmaceutically acceptable disintegrant, diluent, lubricant, binder, wetting agent, flavoring agent, or preservative.
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Non-Patent Citations (3)
| Title |
|---|
| Anti-inflammatory and α‑Glucosidase Inhibitory Activities of Labdane and Norlabdane Diterpenoids from the Rhizomes of Amomum villosum;Hong Yin等;《J. Nat. Prod. 》;20191111;第82卷;第2963-2971页 * |
| 傣药九翅豆蔻不同溶剂提取物的化学成分分析及其抗氧化、抗炎和降血糖活性研究;卢传礼等;《中国民族民间医药》;20170630;第26卷(第12期);第31-36页 * |
| 傣药九翅豆蔻化学成分和药理活性研究进展;卢传礼;《亚太传统医药》;20170731;第13卷(第14期);第50-52页 * |
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