Jia Tao Beijing Feed Inspection Institute 1 Soy Isoflavones 1.1 Basic knowledge Soybean isoflavone is an active ingredient in soybean and a secondary metabolite formed in soybean growth. Isoflavones are one of the flavonoids and are found mainly in legumes. Soy isoflavones are also known as phytoestrogens because they are extracted from plants and have a similar structure to estrogen. The estrogen action of soy isoflavones affects hormone secretion, metabolic biological activity, protein synthesis, and growth factor activity, and is a natural cancer chemopreventive agent. 1.2 Main ingredients In nature, soy isoflavones are available in both glycoside and free form. Isoflavone glucosides are structurally divided into two parts, a glucoside ligand and a glycoside. These two parts form nine isoflavone glucosides through different structures. In non-fermented soy products, only a small amount of isoflavones exist in free form, most of which are in the form of β2 glucoside. The main components are daidzin, glycitin and genistin. There are also less acetyl compounds and malonyl compounds of isoflavone glycosides. In fermented soybean products, isoflavone glucoside is hydrolyzed to free soy isoflavones under the action of β2 glucosidase, mainly daidzein, glycitein and genistein. Isoflavones are structurally and functionally similar to estrogen and are therefore considered phytoestrogens. Soy isoflavones are usually yellow-white powder in the normal case, the melting point is mostly above 100 ° C, stable at room temperature, non-toxic, slightly bitter and astringent, soluble in alcohols, esters and ketones, insoluble Water, hardly soluble in petroleum ether, n-hexane, etc. The anti-oxidation component of soy isoflavones is mainly genistein, in which aglycones are stronger than glycosides, and daidzein and its glycosides have almost no antioxidant effect. 1.3 Functional role 1.3.1 Estrogen-like function The estrogenic effects of soy isoflavones make women's skin smooth, delicate, soft, elastic and youthful. At the same time, it can prevent women's menopausal syndrome. Before and after menopause, due to ovarian dysfunction, the level of estrogen in the body decreases, causing the function adjustment of various organs and tissues to be incompatible, and a series of symptoms such as low mood and osteoporosis occur, and the supplementation of estrogen can achieve prevention and treatment. The purpose of such a condition. 1.3.2 Prevention of Cancer Soy products contain five known anti-cancer factors, one of which is isoflavones, which are unique anti-cancer factors for soy foods. Scientists have concluded that the anti-oxidant properties of genistein and its ability to prevent proliferation are the main reasons for its anti-cancer effect. Soy isoflavones have obvious therapeutic effects on breast cancer, colon cancer, lung cancer, prostate cancer, skin cancer and leukemia. Soy isoflavones also prevent the development of ovarian, colon, gastric and prostate cancers. 1.3.3 Prevention of cardiovascular disease Heart disease is also an estrogen-related disease. As a plant estrogen, soy isoflavones reduce blood lipids and prevent heart disease: estrogen-like effects promote thyroxine secretion and promote bile excretion. It has been well documented that lowering low density lipoprotein (LDL) cholesterol without lowering high density lipoprotein (HDL) cholesterol when lowering cholesterol. Isoflavones, as flavonoids, have a biological antioxidant effect, which is important because the oxidation of low-density lipoprotein cholesterol is a key factor in the arteriosclerosis process. The arterial elasticity of women who consumed 80 mg of genistein per day increased by about 26%. 1.3.4 Prevention of Alzheimer's disease Alzheimer's disease is currently the most common type of dementia, and women suffer more. In recent years, studies have shown that the human brain is also a target tissue for estrogen action, and hippocampal synaptosomes with memory function in the brain contain estrogen receptors. The medical community has confirmed that estrogen levels are closely related to senile dementia, and taking soy isoflavones and true estrogens is beneficial to the brain. 2 Pollen flavonoids 2.1 Basic knowledge Flavonoids are widely found in pollen, such as ginkgo pollen, rape pollen, corn pollen, pine pollen and so on. Most of its constituents are oxidized forms, namely flavonols, white anthocyanins, catechols and chlorogenic acids. Among them, flavonoids mainly exist in the form of free flavonoid aglycones, and have various effects such as anti-inflammatory and anti-atherosclerosis. At present, there are mainly bee pollen and pine pollen. Bee pollen is derived from nature and is a pollen grain collected by the bees from the flowering plants of the flowering plants (nectar plants and pollen-derived plants), and a special gland secretion, nectar and saliva, is mixed. Regular oblate. Bee pollen is mainly distinguished by powdery plants. There are more than ten kinds in China, mainly rapeseed pollen, corn pollen and tea pollen. Pine pollen is pollen of Pinus massoniana, Pinus tabulaeformis or its genus. When flowering from April to May, the male flower is removed, dried, and the pollen is removed to remove impurities. Pine pollen is the pollen of Chinese native tree species Pinus massoniana and Pinus tabulaeformis grown in the mountainous area at an altitude of 1100m~1500m. Compared with bee source pollen, pine pollen is collected manually, with single flower source, pure quality, stable composition, no pesticide residues, and no animal hormones. Pine pollen has a better taste than any other plant pollen, and it feels a light fragrance when taken. 2.2 Main ingredients The flavonoids of pollen are mostly in the form of glycosides, that is, the semi-carboxyaldehyde group of a sugar is combined with aglycosyl and aglycon, and the non-sugar moiety is called an aglycone or glycoside, which is produced by the action of glucosidase, D-glucose. It is the most common combination of sugars, D-galactose and L-rhamnose are also common. Bee pollen is a plant pollen collected by bees, which is used to feed bee larvae during the growth and development of bees. The pollen cluster collected by the bees is mixed with the secretions of honey and bee salivary glands, and there are also α and β glucoside hydrolase in the secretion. Therefore, the flavonoids in bee pollen are mainly present as free flavonoid aglycones, while the aggregation of free rutin in dry bee pollen is obviously a glucosidase, which increases biological activity. Studies have confirmed that each pollen has its own unique HPLC profile of flavonoids or phenols. A single bee pollen grain contains only one type of pollen and can be compared to the HPLC profile of standard pollen by HPLC. The difference in species and content of flavonoids and other phenols in pollen can lead to different antioxidant or free radical scavenging effects of different pollen. Flavonoids can act on the body's metabolism and growth. There are also concerns about the passive protection of flavonoids. Flavonoids act as an attractant for flowers during pollination. 2.3 Functional role 2.3.1 lipid-lowering and cholesterol-lowering effects Pollen flavonoids can effectively remove the fat deposited on the blood vessel wall and soften the blood vessels. 2.3.2 Enhance the body immunity Flavonoids are effective in preventing the development of certain bacterial and viral diseases without developing resistance. It was found that rape bee pollen can increase the proliferation ability of mouse spleen lymphocytes, promote the production of antibody-producing cells, increase the serum hemolysin antibody level, and significantly enhance the phagocytic ability of mouse peritoneal macrophages. 2.3.3 Inhibition of Tumors Pollen flavonoids can significantly enhance the activity of serum superoxide dismutase, reduce serum lactate dehydrogenase activity, serum malondialdehyde content. Rape bee pollen can inhibit tumor formation by enhancing the body's antioxidant capacity. 3 Ginkgo biloba leaf flavonoids 3.1 Basic knowledge Ginkgo biloba (Ginkgo biloba L), also known as ginkgo tree, grandson tree, more than 70% of the world's ginkgo trees grow in China, is one of the ancient tree species in China, with the name of "living fossil". Ginkgo tree grows slowly and has a very long life. It takes more than 20 years from planting to the result. After 40 years, it can produce a lot of results. Therefore, it is also known as "Gongsunshu" and has the meaning of "common seed and sun-eaten food". Ginkgo biloba has been paid more and more attention by experts at home and abroad due to its special growth law and strong disease resistance. Research on the active ingredients and curative effects of Ginkgo biloba has been paid more and more attention. More than 100 kinds of health products, cosmetics and medicines have been developed, which have formed an international market. Emerging industries with more than $2 billion in sales. The chemical constituents of Ginkgo biloba include flavonoids, terpenoids, lactones, phenolic acids, and alkaloids, polyisoprene and other compounds. Flavonoids are one of the main active ingredients of Ginkgo biloba leaves, and their contents vary with variety, origin, age, and picking time. Flavonoids have attracted more and more attention because of their anti-oxidation, anti-virus, prevention and treatment of cardiovascular diseases and enhancement of immunity. 3.2 Main ingredients The flavonoids in Ginkgo biloba can be divided into three kinds of compounds, such as flavonoids, diflavonoids and catechins. There are 36 kinds of compounds, mainly in the form of glycosides. There are 7 kinds of aglycones of ginkgo flavonoids, namely quercetin, kaempferol, isorhamnetin, myricetin, apigenin, hibiscus, and tri-flavonoids. The first three are the main components. The content of these three flavonoid aglycones was mainly detected in the quality control of Ginkgo biloba leaves and extracts (GBE). The flavonoids in Ginkgo biloba leaves are a kind of compound formed by the polymerization of two flavonoid nucleus via CC bond. There are 6 kinds of compounds, namely, ginkgol, isoflavone, flavonoid, flavonoid, and ginkgo biloba. Flavonoids, 5,-methoxyglycine ginkgo bisflavonoids, and the like. There are 6 kinds of catechins in Ginkgo biloba, namely catechin, epicatechin, gallic acid catechin, epigallocatechin, 4,8,-catechin catechin, 4, 8, - gallop catechins. 3.3 Main functions 3.3.1 Antioxidant effect Ginkgo biloba leaf flavonoids have strong scavenging effects on active oxygen free radicals and anti-lipid oxidation. They can regulate superoxide dismutase and peroxidase, and prevent and treat diseases related to reactive oxygen species, such as cardiovascular and cerebrovascular diseases. Disease, senile dementia, aging, neurological diseases, Parkinson's disease, etc. 3.3.2 Anti-tumor and anti-cancer effects Flavonoids are antagonists of cancer promoters, which can eliminate cancer cells and prevent cancer cells from proliferating. There are generally three ways to fight free radicals; directly inhibit cancer cell growth; and fight carcinogenic cancer-promoting factors. 3.3.3 inhibit platelet aggregation The flavonoids in Ginkgo biloba have a strong inhibitory effect on blood coagulation factors, so they show better anticoagulant effect. Experiments have shown that different concentrations of flavonoids from Ginkgo biloba can inhibit platelet aggregation induced by adenosine diphosphate (ADP) in rats, and the same inhibition of platelet aggregation in rabbits and sheep induced by serotonin and ADP. In addition, flavonoids in Ginkgo biloba can also reduce the metabolism of hydroxydecanoic acid in vascular endothelial cells, and reduce the content of collagen or collagen fibers in the inner wall, which is beneficial to prevent platelet adhesion and agglutination and prevent atherosclerosis. 3.3.4 Other Functions Ginkgo flavonoids can relieve pain, treat diabetes and other diseases, and have protective effects on liver tissues. Using ginkgo flavonoids to scavenge free radicals, maintain SOD levels, anti-oxidation, anti-aging, anti-ultraviolet, and high-efficiency sterilization, various skin care products and health care products have been developed, such as Yinkeluo and Bailuda. The effect of natural flavonoids is multi-faceted. It is a strong antioxidant, which can effectively remove oxygen free radicals in the body. For example, anthocyanins and anthocyanins can inhibit the full-stage overflow of oily peroxides. The ability to oxidize is more than 10 times that of vitamin E. This antioxidant action can prevent cell degradation, aging, and prevent cancer. 4 Toxicological studies of flavonoids in plants 4.1 General toxicity test The comprehensive toxic effect of exogenous chemicals on test animals at a certain dose, certain contact time and contact mode is called general toxicity, also known as basic toxicity. The general toxicity study mainly reveals exogenous chemistry. The dose-effect relationship between animals and animals is divided into acute toxicity test, subchronic and chronic toxicity test according to the length of exposure to poison. 4.1.1 Acute Toxicity Test Acute toxicity refers to the toxic effects or even death of a test animal caused by repeated exposure to a chemical in one contact or within 24 hours. The aim is to understand the toxicity and properties of the test substance and to provide a basis for dose selection in accumulative toxicity and subacute toxicity tests. The lethal dose is usually expressed as the LD50, which is the number of milligrams of test substance per kilogram of body weight, ie mg/(kg•BW). A large number of acute toxicity tests have shown that plant flavonoids are non-toxic at appropriate dosages. 4.1.2 test and chronic toxicity test Subchronic toxicity (also called subacute toxicity test) refers to the toxic effects caused by repeated exposure of exogenous chemicals in the test animals (usually 1 month to 3 months); chronic toxicity refers to the long-term exposure of test animals to foreign sources. Toxic effects caused by chemicals. The objective was to observe the toxic effects of the test substance on the animals at different dose levels and the target organs, and to determine the maximum no-effect dose. Body weight, food intake, food utilization, organ weight and organ coefficient, blood biochemistry and cytology and pathology in low, medium and high dose groups of female and male rats in the 30d feeding test of soybean isoflavone compound capsules There was no statistically significant difference between the indexes of histology and the control group, indicating that the soybean isoflavone composite capsule was safe in the dose range. In the systematic toxicology test on the safety of Apocynum venetum tea, the results of the 30-day short-term feeding test showed that it had no potential toxic effects on the growth of the test animals, blood student indicators, major visceral ratios and histology. . In the toxicity test of grape polyphenols, the rats fed the grape polyphenol sample showed that the growth and development of the rats were good within 30 days, and the weight of the animals in each test group increased, food utilization, blood routine, blood biochemistry and organ coefficient. The indicators were all within the normal range, and there was no significant difference between the two groups. In the experimental study on the safety and blood pressure lowering effect of apigenin and its mechanism, rats were fed with 0, 2g/kg, 4g/kg, 6g/kg, 8g/kg apigenin for 13 weeks. The weight and food intake of each dose group There were no significant differences in the indexes of food utilization, blood routine, blood biochemistry and organ coefficient compared with the control group (P>0.05). In the study of the 180d chronic toxicity of the hydroalcoholic extract of DMB on rats, the test results showed that there was no clinical response in the 1000mg/kg dose group, and the 2000mg/kg dose group had symptoms such as piloerection and hypoactivity at the beginning of the test, after 4d Symptoms disappeared, and slight changes such as dyspnea, fatigue, and weakness occurred on the 31st to 42nd day of the test. None of the animals tested died during the test. In the 90d subchronic toxicity test of lupulin, no significant toxic effects were found in the clinical evaluation. The test concluded that the no-injection dose (NOAEL) value of hopsin was 2000 mg/(kg•BW) per day. Based on the above test results, it is known that plant flavonoids do not cause toxic side effects in long-term feeding at an appropriate dose. 4.2 Accumulation toxicity test Exogenous chemicals enter the body, are excreted by metabolic transformation, or directly excreted. However, when it enters the body continuously and repeatedly, and the absorption speed exceeds the rate of metabolic conversion and excretion, the amount of chemical substances in the body gradually increases, which is called the accumulation of chemical substances. The accumulation of exogenous chemicals is the basis for chronic toxicity. Chronic toxicity may be accumulation of substances due to exogenous chemicals or their metabolites, but some chemical substances may not detect the original form of the chemical substance or its metabolites in the body after prolonged contact, but may have chronic toxicity. It is called damage accumulation (also called function accumulation). According to the relevant regulations, if the LD50>10g/(kg•BW), the accumulation toxicity test may not be required (Ministry of Health, 2004). According to the acute toxicity test, the LD50 of most plant flavonoids is greater than 10g/(kg•BW). Therefore, accumulation toxicity tests are rare in the safety evaluation of plant flavonoids. 4.3 Mutagenicity test Mutagenic action refers to the ability of foreign factors to cause changes in genetic material in the nucleus, and this change can be transmitted along with the cell division process. Commonly used tests for testing chemical mutagenicity include bone marrow micronucleus test, sperm abnormality test, chromosome aberration test, and Ames test. The Ames test in the toxicological safety evaluation test of soybean isoflavone composite capsule showed that the dosage of the mutants did not cause a significant increase in the number of revertant mutants under the conditions of adding S-9 or no S-9. Soybean isoflavone compound capsule The results of Ames test were negative; the micronucleus test of mouse bone marrow cells showed that the positive control group was significantly different from the solvent control group (P<0.01), and the micronucleus rate of each dose group was not significantly different from the solvent control group (P>0.05). The mouse bone marrow cells were negative for micronucleus test; the mouse sperm abnormality test showed that the sperm abnormality rate of the positive control group was significantly different from that of the solvent control group (P<0.01), and the sperm abnormality rate of the soybean isoflavone compound capsule group and the solvent control group. There was no significant difference (P>0.05), and the mouse sperm abnormality test was negative. In the systematic toxicology test on the safety of Apocynum venetum tea, the micronucleus test of mouse bone marrow cells showed that the micronucleus rate of polychromatic erythrocytes in mice of each dose group was not significantly different from that of the negative control group. The sample micronucleus test results were negative; the sperm abnormality test showed that the sperm deformity rate of the mice in each dose group was not significantly different from that of the negative control group by X2 test (P>0.05), while the positive group and the negative group were negative. The difference was statistically significant (P<0.01), ie the sample sperm abnormality test was negative (虞 Yingying, 2006). In the Ames test results of flavonoids in the leaves, the six tested concentrations of flavonoids in the leaves were increased with S-9 or without S-9, and the four strains of TA97, TA98, TA100 and TA102 were transformed. The number of colonies was close to the negative control group, there was no significant difference (P>0.05) and did not exceed 2 times of the negative control group, but it was much lower than the positive control group, and there was a significant difference (P<0.01). Therefore, bamboo leaf flavonoids can not cause back mutation of Salmonella typhimurium frameshift mutants and base substitution mutants; bone marrow micronucleus test results of bamboo leaf flavonoids show that the positive control group (cyclophosphamide) has micronucleus The number of multi-stained red blood cells was significantly different from that of the negative control group (bamboo leaf flavonoids 0.00g/kg) (P<0.01). The mice in each dose group of bamboo leaf flavonoids had micronucleus polychromatic erythrocyte rate and negative control group. Compared with the micronucleus rate values, there is no significant difference (P>0.05), and there is no dose-effectiveness relationship. Therefore, bamboo leaf flavonoids have no cleavage effect on mouse bone marrow cells and spindle toxic effects; The results of the mouse sperm abnormality test of flavonoids showed that the positive control group ( The sperm abnormality rate of the cyclophosphamide mice was significantly different from that of the negative control group (bamboo leaf flavones 0.00g/kg) (P<0.01). Compared with the negative control group, the sperm abnormality rate of the bamboo leaf flavonoids was very close to the negative control group, there was no significant difference (P>0.05), and there was no dose-effectiveness relationship, revealing the bamboo leaf flavonoids. The malformation of the mouse sperm has no effect. The Ames test was carried out in the toxicity test of grape polyphenols. The results showed that the number of colonies of the tested samples in each dose group did not exceed 2 times the number of solvent control colonies, and there was no dose-response relationship, indicating that S-with or without S- At 9 o'clock, the test samples showed no genotoxicity to the strains of Salmonella typhimurium TA97, TA98, TA100 and TA102. The test was negative; the mouse bone marrow polychromatic erythrocyte micronucleus and sperm abnormality test showed that each dose group There was no significant difference in the rate of nuclear rate and sperm abnormality compared with the negative control group, while the positive control group of cyclophosphamide was significantly different from the negative control group (P<0.01). In the study of hopsin, both the Ames test and the micronucleus test showed no mutagenicity and genotoxicity. The above test results show that the plant flavonoid compound does not cause changes in the genetic material in the nucleus at an appropriate dose, that is, no mutagenicity. 5 Summary In summary, most toxicological studies suggest that plant flavonoids are generally non-toxic, but the mechanism of action is not fully understood, and it is necessary to systematically study it to provide a scientific basis for the rational scientific use of plant flavonoids. Plant flavonoids are widely distributed in plants. It is safe and feasible to extract phytoflavonoids with various biological activities and non-toxicity from China's abundant plant resources. It will have broad prospects.
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