4547-24-4 Usage
Clinical application and efficacy
Corosolic acid can be used as the novel plant-derived drug for prevention and treatment of obesity and type II diabetes drugs as well as the pharmaceutical raw materials of functional natural health food. It has currently become a hot product in the market. Currently the natural product has entered into market as a nutritional supplement in the United States and has been also subject to the Phase III clinical trials for the treatment of diabetes and will soon be approved by the FDA in the near future. Compared its efficacy in treating diabetes with that of the injections of insulin, it has various advantages such as significant oral administration effect, small toxic side effects, and being convenient for administration. Its efficacy is quite similar with injection of insulin.
The content of corosolic acid content in plants is generally low, even in the Lagerstroemia speciosa which has relative high content of Corosolic aicd. In the hot-wvater extracted concentrated extract of Lagerstroemia speciosa, the corosolic acid content is only about 0.01%. Even in the alocohol extract of Barnabas leaf, corosolic acid content is only about 1%. With years of research, Microherb has adopted advanced chromatographic separation technology for successfully isolation high purity (98%) corosolic acid, which can be further used for pharmacodynamic studies, clinical studies as well as toxicological experiment for prevention oadn treatment of obesity and type II diabetes.
The major efficacy of corosolic acid as follows:
1. it can regulate the content of insulin and blood sugar with significant trend of weight loss in a slow process without the necessary for dieting. It therefore can be used for weight loss.
2. this product has a significant hypoglycemic effect.
3. it has a significant inhibitory effect on inflammation with the anti-inflammatory effect being stronger than commercially available anti-inflammatory drug, indomethacin.
4. it has inhibitory effect on the proliferation of various kinds of tumors, and thus have wide prospects of applications in this field.
Physical and Chemical Properties
It is amorphous white powder (methanol), also known as plant insulin, 2α-hydroxy ursolic acid, and Barabbas extract or Lagerstroemia speciosa extract. It belongs to α-amyrin type or alkyl-type pentacyclic triterpenoids, and is soluble in petroleum ether, benzene, chloroform, pyridine and some other organic solvents, but insoluble in water; it is also soluble in hot ethanol, methanol. Under anhydrous conditions, when it is reacted with a strong acid (sulfuric acid, phosphoric acid, perchloric acid), the acid (TCA) or Lewis's acid (zinc chloride, aluminum chloride, antimony trichloride), there will be colorimetric reaction or fluorescence.
Figure 1 the structural formula of corosolic acid
The above information is edited by the lookchem of Dai Xiongfeng.
Lagerstroemia speciosa extract
Corosolic acid is a kind of triterpenoids which is naturally presented in Lagerstroemia. Its basic skeleton is the pentacyclic parent nucleus of multiple hydrogen-pinenes. It can either exist in the free form or in the form of saponins inside the plant bodies. In plants, it often co-exists with its isomers hawthorn acid (2α-hydroxy oleanolic acid) with similar structures and chemical properties between each other, thus causing difficulty in separation. In vivo results have shown that corosolic acid promotes the cellular glucose uptake and utilization through stimulating the transport of glucose, thus smoothly achieving its hypoglycemic effect. Its excitatory effects on glucose transport is similar to insulin, therefore, people also call corosolic acid as plant insulin.
Animal experiments have shown that corosolic acid has a significant hypoglycemic effect on both normal rats and genetically diabetic mice.
Corosolic acid can also lead to weight loss. Clinical study has found that orally administration of this drug can regulate insulin and blood sugar levels with significant trend of weight loss (average weight loss 0.908-1.816Kg). The whole process is slow and dieting is not necessary. Combination with exercise, drinking a lot of water and regulating the diet with products containing corosolic acid can give rise to the best weight loss efficacy.
In addition corosolic acid also has many other biological activity, such as inhibitory effects on TPA-induced inflammation whose anti-inflammation effect is stronger than commercially available anti-inflammatory drug, indomethacin; it also has a inhibitory effect on DNA polymerase, as well as inhibitory effects on a variety of tumor cell growth.
Plant sources
Lagerstroemia speciosa originates from Asian tropical area and is distributed in India, Sri Lanka, Malaysia, the Philippines and Vietnam. It is routinely cultivated in Guangdong, Guangxi, Yunnan, Hainan and Fujian of china for ornament.
Lagerstroemia speciosa is a kind of folk medicines among Southeast Asia, and is commonly known as "Barabbas ". In India, people take its roots as a kind of astringent. In Malaysia, people apply pounded leaves for treating malaria, and foot fractures. In the Philippines, the tea drinks made from its leaf is widely used in the treatment and prevention of diabetes, known as the "natural plant insulin"; orally administration is effective with no side effects and can reduce the weight without affecting the appetite. In the 90s of last century, scholars abroad, especially in Japan have conducted extensive researches on it with both its chemical composition and pharmacological effects being reported. Recent studies have found that it can lower blood sugar, cause weight loss; it also has effects of anti-tumor, have anti-inflammatory, anti-viral and anti-cardiovascular disease. Especially should pay attention to its good hypoglycemic activity which has similar physiological effects as insulin, and thus also known as "plant insulin" which draw widespread attention. It has been currently developed into various kinds of health care products both at home and abroad.
Figure 2 Lagerstroemia speciosa
Reference quality standards
1. Weight Loss by drying: ≤5%
2. Heavy metals: ≤10ppm
3. Agricultural residues: ≤2ppm
4. Solvent residue: ≤0.5%
5. Tests of microbes: Total ≤1000CFU/G, mold yeast ≤100CFU/G
Uses
Different sources of media describe the Uses of 4547-24-4 differently. You can refer to the following data:
1. (2α,3β)-2,3-Dihydroxy-urs-12-en-28-oic Acid influences inflammatory gene expression regarding inflammatory bowel disease. In addition, its extracted from the plants Gentiana farreri and shows anti-tumor activity
2. (2α,3β)-2,3-Dihydroxy-urs-12-en-28-oic Acid influences inflammatory gene expression regarding inflammatory bowel disease. In addition, its extracted from the plants Gentiana farreri and shows anti-tum
or activity
Definition
ChEBI: A natural product found particularly in Rhododendron species and Eriobotrya japonica.
Check Digit Verification of cas no
The CAS Registry Mumber 4547-24-4 includes 7 digits separated into 3 groups by hyphens. The first part of the number,starting from the left, has 4 digits, 4,5,4 and 7 respectively; the second part has 2 digits, 2 and 4 respectively.
Calculate Digit Verification of CAS Registry Number 4547-24:
(6*4)+(5*5)+(4*4)+(3*7)+(2*2)+(1*4)=94
94 % 10 = 4
So 4547-24-4 is a valid CAS Registry Number.
InChI:InChI=1/C30H48O4/c1-17-10-13-30(25(33)34)15-14-28(6)19(23(30)18(17)2)8-9-22-27(5)16-20(31)24(32)26(3,4)21(27)11-12-29(22,28)7/h8,17-18,20-24,31-32H,9-16H2,1-7H3,(H,33,34)/t17-,18+,20-,21+,22-,23+,24+,27+,28-,29-,30+/m1/s1
4547-24-4Relevant articles and documents
Synthesis of oxygenated oleanolic and ursolic acid derivatives with anti-inflammatory properties
Nelson, Andrew T.,Camelio, Andrew M.,Claussen, Karin R.,Cho, Jiyoon,Tremmel, Lisa,Digiovanni, John,Siegel, Dionicio
, p. 4342 - 4346 (2015/11/03)
The scalable syntheses of four oxygenated triterpenes have been implemented to access substantial quantities of maslinic acid, 3-epi-maslinic acid, corosolic acid, and 3-epi-corosolic acid. Semi-syntheses proceed starting from the natural products oleanolic acid and ursolic acid. Proceeding over five steps, each of the four compounds can be synthesized on the gram scale. Divergent diastereoselective reductions of α-hydroxy ketones provided access to the four targeted diol containing compounds from two precursors of the oleanane or ursane lineage. These compounds were subsequently evaluated for their ability to inhibit inflammatory gene expression in a mouse model of chemically induced skin inflammation. All compounds possessed the ability to inhibit the expression of one or more inflammatory genes induced by 12-O-tetradecanoylphorbol-13 acetate in mouse skin, however, three of the compounds, corosolic acid, 3-epi-corosolic acid and maslinic acid were more effective than the others. The availability of gram quantities will allow further testing of these compounds for potential anti-inflammatory activities as well as cancer chemopreventive activity.
Biocatalytic Synthesis of the Anti-diabetes Agent-corosolic Acid by Whole Cells of Microorganisms
Fu, Shaobin,Meng, Qingfeng,Long, Shu-An,Zhang, Yun,Sun, Di-An,Wei, Gang
, p. 871 - 874 (2015/10/29)
Diabetes is one of the most prevalent and costly global diseases. For diabetes, frequent insulin treatment and synthetic drugs are very expensive and may cause unwanted side effects. Corosolic acid (CA), a natural product, was reported to be efficient in the treatment of diabetes, meanwhile without induction of anti-insulin antibodies and obesity. The preparation of CA attracted many researchers in the world. This study investigated the biocatalytic synthesis method of CA from ursolic acid by Streptomyces griseus subsp. griseus 4.18. LC-MS analysis demonstrated that 5 day, 125 μg/mL substrate, pH=9 and 10% strain concentration were the appropriate conditions. It is estimated that biocatalysis will contribute to the development of green and sustainable synthetic processes with less time-consuming and more environmentally friendly.
Process for preparing high purity corosolic acid and high purity ursolic acid
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Page/Page column 5-6, (2008/12/04)
According to the present invention, there is provided a process for preparing corosolic acid comprising the steps of (1) dissolving crude extract of Japanese loquat leaves in alkali and aqueous alcohol and (2) applying the solution to a nonpolar adsorption resin to obtain corosolic acid.
Naturally occurring pentacyclic triterpenes as inhibitors of glycogen phosphorylase: Synthesis, structure-activity relationships, and X-ray crystallographic studies
Wen, Xiaoan,Sun, Hongbin,Liu, Jun,Cheng, Keguang,Zhang, Pu,Zhang, Liying,Hao, Jia,Zhang, Luyong,Ni, Peizhou,Zographos, Spyros E.,Leonidas, Demettes D.,Alexacou, Kyra-Melinda,Gimisis, Thanasis,Hayes, Joseph M.,Oikonomakos, Nikos G.
experimental part, p. 3540 - 3554 (2009/04/07)
Twenty-five naturally occurring pentacyclic triterpenes, 15 of which were synthesized in this study, were biologically evaluated as inhibitors of rabbit muscle glycogen phosphorylase a (GPa). From SAR studies, the presence of a sugar moiety in triterpene saponins resulted in a markedly decreased activity (7, 18-20) or no activity (21, 22). These saponins, however, might find their value as potential natural prodrugs which are much more water-soluble than their corresponding aglycones. To elucidate the mechanism of GP inhibition, we have determined the crystal structures of the GPb-asiatic acid and GPb-maslinic acid complexes. The X-ray analysis indicates that the inhibitors bind at the allosteric activator site, where the physiological activator AMP binds. Pentacyclic triterpenes represent a promising class of multiple-target antidiabetic agents that exert hypoglycemic effects, at least in part, through GP inhibition.
Pentacyclic triterpenes. Part 5: Synthesis and SAR study of corosolic acid derivatives as inhibitors of glycogen phosphorylases
Wen, Xiaoan,Xia, Jun,Cheng, Keguang,Zhang, Liying,Zhang, Pu,Liu, Jun,Zhang, Luyong,Ni, Peizhou,Sun, Hongbin
, p. 5777 - 5782 (2008/04/03)
The synthesis and biological evaluation of corosolic acid derivatives and related compounds as inhibitors of rabbit muscle glycogen phosphorylase a is described. Within this series of compounds, 8 (IC50 = 7.31 μM), 12d (IC50 = 3.26 μM), and 12e (IC50 = 5.1 μM) exhibited more potent activities than the parent compound 1 (IC50 = 20 μM). SAR of these compounds is also discussed.
Process for producing corosolic acid
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Page/Page column 7, (2008/06/13)
This invention provides an improved process for producing corosolic acid starts from ursolic acid, which occurs in plants in relatively large amounts, the method comprising the steps of oxidizing the hydroxyl group at 3-position and utilizing the carbonyl group at 3-position to introduce a hydroxyl group stereospecifically into the 3-oxoursolic acid at the 2α-position adjacent to the hydroxyl group at 3-position.
Insulin secretion potentiator
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Page/Page column 5, (2008/06/13)
The invention provides an early insulin secretion stimulator comprising corosolic acid, etc. The early insulin secretion stimulator of the invention is capable of rapidly inducing secretion of insulin immediately after meals without inducing secretion of insulin in the absence of blood glucose increase.
Pentacyclic triterpenes. Part 1: The first examples of naturally occurring pentacyclic triterpenes as a new class of inhibitors of glycogen phosphorylases
Wen, Xiaoan,Sun, Hongbin,Liu, Jun,Wu, Guanzhong,Zhang, Luyong,Wu, Xiaoming,Ni, Peizhou
, p. 4944 - 4948 (2007/10/03)
The semi-synthesis, in vitro and in vivo biological evaluation of corosolic acid (1) and maslinic acid (2) are described. Compounds 1 and 2 represent a new class of inhibitors of glycogen phosphorylases. Both 1 and 2 inhibit the increase of fasted plasma glucose of diabetic mice induced by adrenaline. It is therefore proposed that naturally occurring pentacyclic triterpenes 1 and 2 might reduce blood glucose, at least in part, through inhibiting hepatic glycogen degradation.
LAGRENYL ACETATE AND LAGERENOL, TWO TETRACYCLIC TRITERPENOIDS WITH THE CYCLOARTANE SKELETON FROM LAGERSTROEMIA LANCASTERI
Talapatra, Bani,Chaudhuri, Prabir K.,Mallik, Asok K.,Talapatra, Sunil K.
, p. 2559 - 2562 (2007/10/02)
Lagerenyl acetate and lagerenol, two new tetracyclic triterpenoids with the cycloartane skeleton, together with four other triterpenoids 2α-hydroxy-3β-E-p-coumaryloxy-urs-12-en-28-oic acid (jacoumaric acid, isolated as its monoacetylmethylcarboxylate derivative), 2α-hydroxyursolic acid (isolated as its diacetate), germanicyl acetate and friedelin, and sitosterol were isolated from the leaves and twigs of Lagerstroemia lancasteri.The structures of lagerenyl acetate and lagerenol were established as 3β-acetoxycycloart-24-one and 3β-hydroxycycloart-24-one, respectively, on the basis of spectral and chemical evidence.Key Word Index - Lagerstroemia lancasteri; Lythraceae; triterpenoids; lagerenyl acetate; lagerenol; 2α-hydroxy-3β-E-p-coumaryloxy-urs-12-en-28-oic acid; 2α-hydroxyursolic acid; germanicyl acetate; friedelin; β-sitosterol.
