BacosineCAS# 198014-94-7 |
Quality Control & MSDS
Number of papers citing our products
Chemical structure
3D structure
| Cas No. | 198014-94-7 | SDF | Download SDF |
| PubChem ID | 71312547 | Appearance | Powder |
| Formula | C30H48O3 | M.Wt | 456.7 |
| Type of Compound | Triterpenoids | Storage | Desiccate at -20°C |
| Solubility | Soluble in Chloroform,Dichloromethane,Ethyl Acetate,DMSO,Acetone,etc. | ||
| Chemical Name | (1R,3aR,5aS,5bR,7aR,9R,11aR,11bR,13aR,13bR)-9-hydroxy-3a,5b,8,8,11a-pentamethyl-1-prop-1-en-2-yl-1,2,3,4,5,6,7,7a,9,10,11,11b,12,13,13a,13b-hexadecahydrocyclopenta[a]chrysene-5a-carboxylic acid | ||
| SMILES | CC(=C)C1CCC2(C1C3CCC4C5(CCC(C(C5CCC4(C3(CC2)C(=O)O)C)(C)C)O)C)C | ||
| Standard InChIKey | CLOUCVRNYSHRCF-CHVGUTEKSA-N | ||
| Standard InChI | InChI=1S/C30H48O3/c1-18(2)19-10-13-27(5)16-17-30(25(32)33)20(24(19)27)8-9-22-28(6)14-12-23(31)26(3,4)21(28)11-15-29(22,30)7/h19-24,31H,1,8-17H2,2-7H3,(H,32,33)/t19-,20+,21-,22+,23+,24+,27+,28-,29+,30+/m0/s1 | ||
| General tips | For obtaining a higher solubility , please warm the tube at 37 ℃ and shake it in the ultrasonic bath for a while.Stock solution can be stored below -20℃ for several months. We recommend that you prepare and use the solution on the same day. However, if the test schedule requires, the stock solutions can be prepared in advance, and the stock solution must be sealed and stored below -20℃. In general, the stock solution can be kept for several months. Before use, we recommend that you leave the vial at room temperature for at least an hour before opening it. |
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| About Packaging | 1. The packaging of the product may be reversed during transportation, cause the high purity compounds to adhere to the neck or cap of the vial.Take the vail out of its packaging and shake gently until the compounds fall to the bottom of the vial. 2. For liquid products, please centrifuge at 500xg to gather the liquid to the bottom of the vial. 3. Try to avoid loss or contamination during the experiment. |
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| Shipping Condition | Packaging according to customer requirements(5mg, 10mg, 20mg and more). Ship via FedEx, DHL, UPS, EMS or other couriers with RT, or blue ice upon request. | ||
| Description | Bacosine exhibits moderate analgesic effects, it also plays a role in regulating cell metastasis by inhibiting MMP-9 and showing anti-apoptotic effect in breast cancer cells. Bacosine may have insulin-like activity and its antihyperglycemic effect might be due to an increase in peripheral glucose consumption as well as protection against oxidative damage in alloxanized diabetes. | |||||
Bacosine Dilution Calculator
Bacosine Molarity Calculator
| 1 mg | 5 mg | 10 mg | 20 mg | 25 mg | |
| 1 mM | 2.1896 mL | 10.9481 mL | 21.8962 mL | 43.7924 mL | 54.7405 mL |
| 5 mM | 0.4379 mL | 2.1896 mL | 4.3792 mL | 8.7585 mL | 10.9481 mL |
| 10 mM | 0.219 mL | 1.0948 mL | 2.1896 mL | 4.3792 mL | 5.4741 mL |
| 50 mM | 0.0438 mL | 0.219 mL | 0.4379 mL | 0.8758 mL | 1.0948 mL |
| 100 mM | 0.0219 mL | 0.1095 mL | 0.219 mL | 0.4379 mL | 0.5474 mL |
| * Note: If you are in the process of experiment, it's necessary to make the dilution ratios of the samples. The dilution data above is only for reference. Normally, it's can get a better solubility within lower of Concentrations. | |||||
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Where Is Bacosine in Commercially Available Bacopa monnieri?[Pubmed:32325509]
Planta Med. 2020 May;86(8):565-570.
Bacopa monnieri is an Ayurvedic plant with rising interest in the pharmacological effects of its extract and constituents, including flavonoids, saponins, and triterpenes such as cucurbitacins, betulinic acid, and Bacosine. The latter two compounds are isomeric 3-hydroxy lupenoic acids, which vary only in the arrangement of the carboxylic acid group and the methyl group at C-27 and C-28 and the orientation of the hydroxy group at C-3. In this study, we have reinvestigated the contents of betulinic acid and Bacosine, respectively, in extracts from various commercially available B. monnieri powders and food supplements. To our surprise, HPLC-ion trap time-of-flight analyses identified only betulinic acid, but not Bacosine, in all extracts under study, which was verified by GC-MS, HPLC-ELSD, 1D NMR ((1)H,(13)C), and 2D NMR ((1)H,(1)H COSY, (1)H,(13)C HMBC, (1)H,(13)C HSQC, (1)H,(1)H NOESY) experiments. Moreover, it turned out that commercially available reference samples of Bacosine were structurally identical with betulinic acid.
In vitro evaluation of Bacopa monniera extract and individual constituents on human recombinant monoamine oxidase enzymes.[Pubmed:24449518]
Phytother Res. 2014 Sep;28(9):1419-22.
Bacopa monniera is a traditional Ayurvedic medicinal plant that has been used worldwide for its nootropic action. Chemically standardized extract of B. monniera is now available as over the counter herbal remedy to enhance memory in children and adults. Considering the nootropic action of B. monniera, we evaluated the effect of clinically available B. monniera extract and six of B. monniera constituents (bacoside A3, bacopaside I, bacopaside II, bacosaponin C, Bacosine, and bacoside A mixture) on recombinant human monoamine oxidase (MAO) enzymes. The effect of B. monniera extract and individual constituents on human recombinant MAO-A and MAO-B enzymes was evaluated using MAO-Glo(TM) assay kit (Promega Corporation, USA), following the instruction manual. IC50 and mode of inhibition were measured for MAO enzymes. Bacopaside I and bacoside A mixture inhibited the MAO-A and MAO-B enzymes. Bacopaside I exhibited mixed mode of inhibition with IC50 and Ki values of 17.08 +/- 1.64 and 42.5 +/- 3.53 microg/mL, respectively, for MAO-A enzyme. Bacopaside I is the major constituent of B. monniera, which inhibited the MAO-A enzyme selectively.
Antihyperglycemic activity of bacosine, a triterpene from Bacopa monnieri, in alloxan-induced diabetic rats.[Pubmed:21154199]
Planta Med. 2011 May;77(8):804-8.
This article describes the antihyperglycemic activity, in vivo antioxidant potential, effect on hemoglobin glycosylation, estimation of liver glycogen content, and in vitro peripheral glucose utilization of Bacosine, a triterpene isolated from the ethyl acetate fraction (EAF) of the ethanolic extract of Bacopa monnieri. Bacosine produced a significant decrease in the blood glucose level when compared with the diabetic control rats both in the single administration as well as in the multiple administration study. It was observed that the compound reversed the weight loss of the diabetic rats, returning the values to near normal. Bacosine also prevented elevation of glycosylated hemoglobin in vitro with an IC(5)(0) value of 7.44 microg/mL, comparable with the one for the reference drug alpha-tocopherol. Administration of Bacosine and glibenclamide significantly decreased the levels of malondialdehyde (MDA), and increased the levels of reduced glutathione (GSH) and the activities of superoxide dismutase (SOD) and catalase (CAT) in the liver of diabetic rats. Bacosine increased glycogen content in the liver of diabetic rats and peripheral glucose utilization in the diaphragm of diabetic rats in vitro, which is comparable with the action of insulin. Thus, Bacosine might have insulin-like activity and its antihyperglycemic effect might be due to an increase in peripheral glucose consumption as well as protection against oxidative damage in alloxanized diabetes.
In vitro safety evaluation and anticlastogenic effect of BacoMind on human lymphocytes.[Pubmed:18478974]
Biomed Environ Sci. 2008 Feb;21(1):7-23.
OBJECTIVE: BacoMind (BM) is a standardized extract of Bacopa monnieri, which belongs to the family Scrophulariaceae and is a creeping annual plant found throughout the Indian subcontinent. It has been used by Ayurvedic medicinal practitioners in India for almost 3000 years and is classified as a medharasayana, a substance which improves memory and intellect. With the widespread traditional use as well as scientific validation of Bacopa monnieri for nootropic activity, a bioactive-rich unique phytochemical composition-BacoMind was developed from B. monnieri for use as a cognition and memory enhancing agent. The present study aimed to investigate the in vitro toxicity of this formulation of BacoMind on human lymphocytes and to rule out its possible contribution to mutagenicity. METHODS: In the present investigation the active ingredients present in BM were identified and quantified by high performance liquid chromatography (HPLC) and high performance thin-layer chromatography (HPTLC). Antioxidant and anticlastogenic properties of BM were studied in vitro with and without metabolic activation. Doses of BM were chosen on the basis of mitotic index (MI) and cytokinesis-block proliferation index (CBPI). Clastogenicity assays were performed at 31.2 microg/mL, 62.5 microg/mL, and 125 microg/mL, while the Salmonella reverse mutation assay (Ames test) was performed at doses of 61.72, 185.18, 555.55, 1666.67, and 5000.00 microg/plate. RESULTS: HPLC and HPTLC analysis of BM revealed the presence of bacoside A3, bacopaside I, bacopaside II, jujubogenin isomer of bacopasaponin C, Bacosine, luteolin, apigenin, Bacosine, and beta-sitosterol D glucoside. BM demonstrated significant antioxidant activity. The number of chromosomal aberrations and the frequency of micronuclei induced by BM were not statistically significant up to a dose of 62.5 microg/mL. A subsequent dose of 125 microg/mL prior to metabolic activation induced mild clastogenicity, but it was found to be biologically insignificant as this effect was not seen post metabolic activation. BM also demonstrated a dose-dependent protection against the clastogens used in this study using the above tests for clastogenicity. Maximum protection was observed in presence of metabolic activation. Moreover, BM demonstrated no mutagenic effect on the tested strains, as observed in the Ames test. CONCLUSION: BM protected human lymphocytes against various clastogens. BM also exhibited high antioxidant activity which might be responsible for the observed protective effects against the clastogens since the used clastogens are known to induce their clastogenic effects via production of oxidative radicals.
Bacosterol glycoside, a new 13,14-seco-steroid glycoside from Bacopa monnieri.[Pubmed:16462073]
Chem Pharm Bull (Tokyo). 2006 Feb;54(2):240-1.
A new sterol glycoside, bacosterol-3-O-beta-D-glucopyranoside along with bacopasaponin-C, bacopaside-I, bacopaside-II, bacosterol, Bacosine and luteolin-7-O-beta-glucopyranoside have been isolated from Bacopa monnieri. Their structures were elucidated mainly on the basis of IR, 1D, 2D NMR (HMQC, HMBC, COSY), HR-ESI-QTOF-MS and EI mass spectral studies.
