TWI644668B - A medicinal component containing a natural stilbene compound and applications of the stilbene compound - Google Patents

Abstract

A newly identified natural stilbene compound isolated from groundnut with a chemical formula of C ₁₉ H ₁₈ O ₄ , chemical name 3,4,5'-trihydroxy-6'', 6''-dimethylpyran[2'', 3'': 3', 4'] stilbene, which has the ability to resist oxidation and scavenge free radicals in organisms, to delay aging, especially for extending lifespan.

Description

Medicinal composition comprising natural stilbene compound and use of the same

The present invention relates to a stilbene compound isolated from groundnut, which has the ability to resist oxidation and scavenge free radicals in an organism, to achieve a function of delaying aging, and particularly to extend life.

This invention relates to the use of stilbene compounds. Further, a pharmaceutical composition and a health food for improving the antioxidant ability of a living body are characterized by comprising a stilbene compound, a pharmaceutically or food acceptable carrier, an excipient, a diluent or a base.

Groundnut related research

The groundnut, also known as the longevity fruit, was first published in the "Southern Materia Medica". Traditional medicine believes that the taste of peanuts is sweet, warm and non-toxic. Function of running lungs, and stomach, attending dry cough, nausea, athlete's foot, breast milk less, apply to spleen deficiency and less food, weight loss or postpartum blood gas deficiency, and lung deficiency and chronic cough, intestinal dry constipation or various bleeding embolism. Modern medicine has confirmed the effects of blood pressure reduction, hemostasis, and lowering serum cholesterol.

Groundnut is an important and important cereal crop in the world. It is also an important source of synthetic natural antioxidant and bioactive polyphenol compounds. Among them, peanut kernels can be induced to produce resveratrol and isopropenyl stilbenes (Keen, 1975; Keen and Ingham, 1976; Aguamah et al., 1981; Wotton and Strange, 1985; Sobolev et Al., 1995; Chang et al., 2006) is the most valued. Resveratrol and isopropylene stilbene compounds It is a highly active natural antioxidant. Resveratrol has antioxidant, anti-aging, anti-cardiovascular and anti-cancer functions (Soleas et al., 1997; Fremont, 2000; Chiou et al., 2002; Aggarwal Et al., 2004), polyphenolic compounds in red wines with resveratrol as an important active ingredient, have the risk of inhibiting the oxidation of human low-density lipoprotein and reducing cardiovascular disease (Frankel et al., 1993; 1995; Soleas et al. (1997) are also associated with the function of estrogen and can inhibit the production of Prostaglandin E2 to improve immunity (Gehm et al., 1997; Kopp, 1998; Wu and Huang, 2001). Among them, resveratrol has been recognized for its anti-cancer function (Jang et al., 1997; Subbaramaial et al., 1998; Carbo et al., 1999; Fremont 2000; Bhat et al., 2001; Aggarwal et al., 2004; Weng et al., 2010). In recent years, the research team at Harvard University has further discovered that resveratrol has prolonged the lifespan of yeast and mice, and it is also a cause of concern in the field of biomedical health (Howitz et al., 2003; Baur et al., 2006). ).

In addition to resveratrol, groundnuts can also induce the production of a variety of isopentenyl stilbenes, showing the activity and structure of the different derivatives of resveratrol. Related to the 3,5,4'-trihydroxy group, especially the 4'-hydroxy group is the most important. In contrast, the main isopropenyl stilbene compounds in which peanuts can be induced in large quantities also have the functional groups of resveratrol. And its polarity is lower than resveratrol, it can be expected to have stronger affinity or permeability with the cell membrane to produce stronger biological activity, and may have more potential for bioactive applications. In recent years, resveratrol has also been found in peanut kernels and general peanut products, but at very low levels (Sobolev et al., 1999; Sanders et al., 2000; Chiou 2002).

The objects and advantages of the invention will be set forth in part or in the description.

The object of the present invention is to provide a natural compound 3,4,5'-trihydroxy-6",6"-dimethylpyran[2",3":3',4']stilbene which is extracted from groundnut.

Another object of the invention is that the compound 3,4,5'-trihydroxy-6",6"-dimethylpyran[2",3":3',4']stilbene has anti-oxidation, scavenging free radicals and anti-aging ability And thus extend the life.

The beneficial effects of the present invention are: the natural compound 3,4,5'-trihydroxy-6",6"-dimethylpyran[2",3":3',4']stilbene obtained by groundnut is matched with the base for daily consumption. The health care product made of the ingredients makes the natural compound 3,4,5'-trihydroxy-6",6"-dimethylpyran[2",3":3',4']stilbene at a suitable concentration The more convenient packaging type is obtained and ingested, which can make up for the civilized diseases caused by the imbalance of modern people's diet, and provide health foods that can be used as daily maintenance to delay aging. The invention has the anti-aging and anti-free radical ability health-care product in vivo, and the preferred embodiment comprises the natural compound 3,4,5'-trihydroxy-6",6"-dimethylpyran[2", 3": 3', 4'] stilbene and a base ingredient. Wherein, the binder component may be a material selected from the group consisting of starch, beans, grains, and animal feed, wherein the animal feed comprises aquatic and terrestrial animal feed. And the natural compound 3,4,5'-trihydroxy-6",6"-dimethylpyran[2",3":3',4']stilbene and the base component can be further mixed and processed to form an ingot Agent, block and powder form. In addition, the base component may also be a liquid, and the extract is formulated with a liquid carrier to form a health care product in the form of a liquid containing or not containing alcohol.

Another object of the present invention is to provide a product containing a natural compound 3,4,5'-trihydroxy-6",6"-dimethylpyran[2",3":3',4']stilbene, such as cosmetics and pharmaceuticals.

A second object of the present invention is to provide a product containing the natural compound 3,4,5'-trihydroxy-6",6"-dimethylpyran[2",3":3',4']stilbene, such as a cream, lotion , a plaster or the like; and a pharmaceutical, such as a tablet, capsule, solution, suspension or the like in a pharmaceutically acceptable excipient.

The invention provides a health care product with anti-aging and anti-free radical ability in the living body. In order to verify the effects of the present invention, further confirmation can be made through animal experiments or indirect human experiments. The present invention provides an example of an optimal natural compound 3,4,5'-trihydroxy-6",6"-dimethylpyran[2",3":3',4']stilbene, which will be understood by those skilled in the art. Any modification of the technical solution of the present invention by concentrated extraction, additional addition, modification by different types of products (eg, gelatinous, alcoholic or non-alcoholic beverages) may result in falling within the scope of the present invention.

The invention will be described in detail with particular embodiments. These specific examples are provided by way of illustration of the invention and are not intended to limit the invention. The present invention is intended to embrace these and other modifications and variations within the scope and spirit of the invention.

It is an object of the present invention to provide a stilbene compound having an antioxidant power and a free radical scavenging ability isolated from a peanut extract. A stilbene compound having a delayed aging function, comprising a novel undisclosed compound 3,4,5'-trihydroxy-6",6"-dimethylpyran[2",3":3',4' ]stilbene.

It is an object of the present invention to provide a natural compound 3,4,5'-trihydroxy-6",6"-dimethylpyran[2",3":3',4' which is obtained from groundnut with a function of delaying aging and prolonging life. ]stilbene. It determines the chemical molecular structure by nuclear magnetic resonance spectroscopy (NMR), as shown in Figure 1.

Figure 1, 3, 4, 5'-trihydroxy-6", 6"-dimethylpyran [2", 3": 3', 4'] chemical molecular structure of stilbene

The 3,4,5'-trihydroxy-6",6"-dimethylpyran[2",3":3',4']stilbene obtained according to the examples has the following properties: light gray powder, UV (MeOH) Λmax(log ε): 340 nm (4.74); EIMS m/z: 310 (19), 309 (M-1, 100), 293 (M-17, 1), 281 (1), 265 (2), 251 (1) ), 201(3), 159(2); ESI-HRMS (negative ion mode) (m/z): [C ₁₉ H ₁₈ O ₄ -H+] calculated value 309.1211, measured value 309.1111; molecular formula C ₁₉ H ₁₈ O ₄ ; IR νmax(film)/cm-1:1607, 1566, 1516, 1431, 1360, 1329, 1281, 1114, 1059, 959, 859, 829, 804; ¹ H and ¹³ C NMR data are shown in Table 1. 3, 4, 5 '-trihydroxy-6',6"-dimethylpyran[2",3":3',4']stilbene, which was identified as the first natural compound identified by the relevant literature.

Natural compound 3,4,5'-trihydroxy-6",6"-dimethylpyran[2",3":3',4']stilbene (abbreviated as Ab2) evaluates the anti-aging function of young mice

Animal experiment method

This study was modified with reference to the “Reduction of aging function assessment method” published by the Department of Health, and further explored the natural compound 3,4,5'-trihydroxy-6",6"-dimethylpyran[2",3":3 in animal model. ',4']stilbene (abbreviated as Ab2) delays aging. The adult ICR male rats aged 6 months old were used as test subjects, and 80 μl of Ab2 15% alcohol solution was administered daily. The group included: control group (control, 15% alcohol) and experimental group (0.2 mg Ab2/kg bw). ). Seven rats in each group were fed separately according to the dose, and the animals were sacrificed after 30 days to carry out the biochemical indicators of anti-aging function. Detection.

Determination of biochemical indicators: analysis of antioxidant enzyme activities contained in liver, kidney and brain tissues of mice, including glutathione peroxidase (GSH Px), glutathione reductase (GSH) Rd), Catalase, Glucose-6-phosphate dehydrogenase (G6PD) and Superoxide dismutase (SOD) were used as biochemical indicators.

The experimental data were analyzed by SPSS/PC statistical analysis software for analysis of variance (ANOVA). The differences between the experimental groups were tested. If there were differences, Duncan’s multiple range test was used for further analysis. In addition, Student T-test was also used to compare the differences between the experimental groups.

Experimental result

Six-month-old adult ICR mice were fed Ab2 15% alcohol solution daily for 30 days. The average body weight of the animals during feeding was not significantly different between the groups. After 30 days of feeding, the organ weight and body weight of each group showed no significant difference between the groups. In terms of blood analysis, blood biochemical values of each group of animals such as hemoglobin (HGB), hematocrit (HCT), glutamate acetate transaminase (GOT), glutamate pyruvate transaminase (GPT), There was no significant difference in serum total protein (TP), blood urea nitrogen (BUN), total cholesterol (T-Chol), triglyceride (TG), and low density lipoprotein (LDH), indicating that the natural compound Gem- dimethyl 3 , 4-pyranosyl 3', 4', 5-trihydroxyl stilbene does not affect the main metabolic reactions and organ function in the body in the dose range of this test.

Five kinds of antioxidant enzyme activities in the liver, kidney and brain of the mice were analyzed, and the results are shown in Table 1.

^** 0.2mg Ab2/kg bw

As shown in the results in Table 1, the tube is fed with the natural compound 3,4,5'-trihydroxy-6",6"-dimethylpyran[2",3":3',4']stilbene to enhance the 6-month-old male mouse. GPx and G6PD activities in liver, kidney and brain; GR and SOD activities were evident in liver and kidney, but not in brain (statistically no difference); CAT activity also showed an increase in activity in liver and kidney, and in brain CAT activity was not detected. Overall, feeding 3,4,5'-trihydroxy-6",6"-dimethylpyran[2",3":3',4']stilbene can increase liver, kidney and brain resistance in 6-month-old male rats. The activity of oxidase can improve the antioxidant capacity of the liver, kidney and brain. When the antioxidant defense system in the organism increases, the decomposition of reactive oxygen species can effectively reduce cell damage and delay the aging and death of the organism.

Conclusions It is confirmed that feeding the natural compound 3,4,5'-trihydroxy-6",6"-dimethylpyran[2",3":3',4']stilbene can improve the liver, kidney and brain of 6-month-old male rats. The activity of antioxidant enzymes, therefore, can improve the antioxidant capacity of the liver, kidneys and brain. When the antioxidant defense system in the organism increases, the decomposition of active oxygen species can effectively reduce cell damage and delay the aging and death of the organism. Therefore, the present invention discloses that 3,4,5'-trihydroxy-6",6"-dimethylpyran[2",3":3',4']stilbene obtained from peanuts can be utilized for the manufacture of aging-preventing organisms. A pharmaceutical composition with death, and a health food that can be used to make anti-aging.

The present invention obtains the natural compound 3,4,5'-trihydroxy-6",6"-dimethylpyran[2",3":3',4']stilbene from groundnut by the addition of an excipient used in the conventional art. It is prepared into a pharmaceutical composition, wherein the excipient and the excipient of the conventional oral dosage form include: a binder, a disintegrating agent and a lubricant. Adhesives suitable for pharmaceutical compositions and dosage forms: corn starch, potato starch or other starches, sodium alginate, natural and synthetic gums, powdered tragacanth, guar gum, cellulose and its derivatives, ethyl cellulose , cellulose acetate, calcium carboxymethyl cellulose, sodium carboxymethyl cellulose, microcrystalline cellulose, and a mixture of their excipients, the components used in the coating layer include: methyl cellulose (Methyl cellulose), Hydroxymethyl propyl cellulose, Hydroxymethyl propyl cellulose, Polyvinyl alcohol, Polyvinyl pyrrolidone, Cellulose acetate Acetate phthalate) or other material suitable for use in the present invention, methylcellulose, to prepare a pharmaceutical composition. The pharmaceutical composition of 3,4,5'-trihydroxy-6",6"-dimethylpyran[2",3":3',4']stilbene according to the present invention may be added with a pharmaceutically acceptable additive .

However, the above description is only a preferred embodiment of the present invention, and the present invention cannot be limited thereto. The scope of the invention, that is, the changes and modifications made by the invention in the scope of the invention and the scope of the invention are still within the scope of the invention.

references

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Claims (8)

A pharmaceutical composition comprising a natural stilbene compound represented by the formula (I), which is used for enhancing antioxidant power and scavenging free radicals and prolonging life. A use of the compound as described in the pharmaceutical composition of claim 1 for the isolation of a medicament for delaying aging and prolonging life. The use of the second item of the patent application, which is an agent for enhancing the antioxidant power and the ability to scavenge free radicals and prolonging the life, wherein the medicament comprises a groundnut extract and a pharmaceutically acceptable carrier, an excipient, and a dilution. Agent or base. For the purpose of claim 3, the base component is a material selected from the group consisting of starch, beans, grains, animal feed and animal feed, wherein the animal feed comprises aquatic and terrestrial animal feed. For the purpose of claim 3, the carrier may be a combination of a groundnut extract to prepare a liquid formulation containing or not containing alcohol. A health food for improving anti-oxidation and scavenging ability and prolonging life, characterized by comprising the pharmaceutical composition of claim 1, wherein the compound contained in the pharmaceutical composition is prepared from groundnut and The extract is comprised of a commercially acceptable carrier, excipient, diluent or binder. For example, the health food of claim 6 is used to delay aging and prolong life. For example, in the health food of claim 6 of the patent scope, the carrier may be a combination of groundnut extract A health food product containing a liquid form containing or not containing alcohol.