NeoandrographolideCAS# 27215-14-1 |
Quality Control & MSDS
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| Cas No. | 27215-14-1 | SDF | Download SDF |
| PubChem ID | 160143 | Appearance | White powder |
| Formula | C26H40O8 | M.Wt | 480.60 |
| Type of Compound | Diterpenoids | Storage | Desiccate at -20°C |
| Synonyms | Neoandrographiside | ||
| Solubility | DMSO : ≥ 250 mg/mL (520.19 mM) *"≥" means soluble, but saturation unknown. | ||
| Chemical Name | 4-[2-[(4aS,5R,8aS)-5,8a-dimethyl-2-methylidene-5-[[(2R,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxymethyl]-3,4,4a,6,7,8-hexahydro-1H-naphthalen-1-yl]ethyl]-2H-furan-5-one | ||
| SMILES | CC1(CCCC2(C1CCC(=C)C2CCC3=CCOC3=O)C)COC4C(C(C(C(O4)CO)O)O)O | ||
| Standard InChIKey | YGCYRQKJYWQXHG-JXAGCRMJSA-N | ||
| Standard InChI | InChI=1S/C26H40O8/c1-15-5-8-19-25(2,14-33-24-22(30)21(29)20(28)18(13-27)34-24)10-4-11-26(19,3)17(15)7-6-16-9-12-32-23(16)31/h9,17-22,24,27-30H,1,4-8,10-14H2,2-3H3/t17?,18-,19-,20-,21+,22-,24-,25+,26+/m1/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 | Neoandrographolide has antiradical, anti-inflammatory,and hypolipidemic effects, it protects the cardiovascular without significant liver damage. Neoandrographolide as chemosensitizer in S-Jurkat and X chromosome-linked inhibitor of apoptosis protein (XIAP)-overexpressing Jurkat cells, a model for chemoresistance.Neoandrographolide inhibits iNOS and COX-2 expression through inhibiting p38 MAPKs activation. |
| Targets | NOS | NO | COX | PGE | p38MAPK | JNK | ERK | NF-kB | TNF-α |
| In vitro | Neoandrographolide from Andrographis paniculata as a potential natural chemosensitizer.[Pubmed: 20446243]Planta Med. 2010 Oct;76(15):1698-700.Extracts of the traditional medicinal herb Andrographis paniculata and its main constituents are described in the literature as showing anticancer activity. The aim of this study was to isolate the main constituents of a commercially available phytotherapeutic preparation of A. paniculata and to determine their chemosensitizing potential in a leukemia cell line.
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| In vivo | Hypolipidemic effects of andrographolide and neoandrographolide in mice and rats.[Pubmed: 22744979]Phytother Res. 2013 Apr;27(4):618-23.Andrographolide (AND) and Neoandrographolide (NEO) are the diterpenoids from the Andrographis paniculata (Acanthaceae). It is reported the diterpenoids exhibit a wide spectrum of biological activities. In vivo and in vitro anti-inflammatory activities of neoandrographolide.[Pubmed: 17436371]Am J Chin Med. 2007;35(2):317-28.Neoandrographolide, one of the principal diterpene lactones, isolated from a medicinal herb Andrographis paniculata Nees, was tested in vivo and in vitro for its anti-inflammatory activities and mechanism. |
| Cell Research | Inhibitory effects of neoandrographolide on nitric oxide and prostaglandin E2 production in LPS-stimulated murine macrophage.[Pubmed: 17109078]Mol Cell Biochem. 2007 Apr;298(1-2):49-57.Activated macrophages express inducible isoforms of nitric oxide synthase (iNOS) and cyclooxygenase-2 (COX-2), produce excessive amounts of nitric oxide (NO) and prostaglandin E(2) (PGE(2)), which play key roles in the processes of inflammation. Andrographis paniculata Nees is a traditional Chinese herb commonly used for treatment of infection, inflammation, and diarrhea. However, the mechanism of its therapeutic function is not well known. |
Neoandrographolide Dilution Calculator
Neoandrographolide Molarity Calculator
| 1 mg | 5 mg | 10 mg | 20 mg | 25 mg | |
| 1 mM | 2.0807 mL | 10.4037 mL | 20.8073 mL | 41.6146 mL | 52.0183 mL |
| 5 mM | 0.4161 mL | 2.0807 mL | 4.1615 mL | 8.3229 mL | 10.4037 mL |
| 10 mM | 0.2081 mL | 1.0404 mL | 2.0807 mL | 4.1615 mL | 5.2018 mL |
| 50 mM | 0.0416 mL | 0.2081 mL | 0.4161 mL | 0.8323 mL | 1.0404 mL |
| 100 mM | 0.0208 mL | 0.104 mL | 0.2081 mL | 0.4161 mL | 0.5202 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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Neoandrographolide is a diterpenoid from the Andrographis paniculata (Acanthaceae).
References:
[1]. Tao Yang, et al. Hypolipidemic Effects of Andrographolide and Neoandrographolide in Mice and Rats. Phytotherapy Research Volume 27, Issue 4, pages 618–623, April 2013
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Hypolipidemic effects of andrographolide and neoandrographolide in mice and rats.[Pubmed:22744979]
Phytother Res. 2013 Apr;27(4):618-23.
Andrographolide (AND) and Neoandrographolide (NEO) are the diterpenoids from the Andrographis paniculata (Acanthaceae). It is reported the diterpenoids exhibit a wide spectrum of biological activities. The aim of this study was to investigate the hypolipidemic effect of AND and NEO in hyperlipidemic mice induced by 75% yolk emulsion and in hyperlipidemic rats induced by high fat emulsion, respectively. The results showed that the levels of triglyceride, total cholesterol (TC) and low-density lipoprotein cholesterol were reduced by AND and NEO in a dose-dependent tendency in mice. Compared with the model group, the plasma TC levels of experimental groups with AND and NEO at 100 mg/kg dosage decreased by 23.9 and 20.2% in rats, respectively (P < 0.05). It was also found that the plasma aspartate transaminase and alanine transaminase levels were significantly decreased by feeding with AND and NEO in rats, compared with positive group (simvastatin) (P < 0.01). Otherwise, AND and NEO could protect the cardiovascular due to down-regulation of iNOS expression and up-regulation of eNOS expression. In conclusion, AND and NEO have potent hypolipidemic effects and protect the cardiovascular without significant liver damage.
Neoandrographolide from Andrographis paniculata as a potential natural chemosensitizer.[Pubmed:20446243]
Planta Med. 2010 Oct;76(15):1698-700.
Extracts of the traditional medicinal herb Andrographis paniculata and its main constituents are described in the literature as showing anticancer activity. The aim of this study was to isolate the main constituents of a commercially available phytotherapeutic preparation of A. paniculata and to determine their chemosensitizing potential in a leukemia cell line. Chromatographic separation steps resulted in the isolation of the diterpenes andrographolide (1) and 14-deoxy-11,12-didehydroandrographolide (3) and the diterpene glucoside Neoandrographolide (2). The combination of these constituents with suboptimal concentrations of etoposide revealed compound 2 as chemosensitizer in S-Jurkat and X chromosome-linked inhibitor of apoptosis protein (XIAP)-overexpressing Jurkat cells, a model for chemoresistance.
Inhibitory effects of neoandrographolide on nitric oxide and prostaglandin E2 production in LPS-stimulated murine macrophage.[Pubmed:17109078]
Mol Cell Biochem. 2007 Apr;298(1-2):49-57.
Activated macrophages express inducible isoforms of nitric oxide synthase (iNOS) and cyclooxygenase-2 (COX-2), produce excessive amounts of nitric oxide (NO) and prostaglandin E(2) (PGE(2)), which play key roles in the processes of inflammation. Andrographis paniculata Nees is a traditional Chinese herb commonly used for treatment of infection, inflammation, and diarrhea. However, the mechanism of its therapeutic function is not well known. In the present study, the effect of Neoandrographolide, one of bioactive components in A. paniculata, on iNOS-mediated NO production and COX-2-mediated PGE(2) in bacterial lipopolysaccharide (LPS) stimulated-murine macrophages was investigated. Neoandrographolide at concentrations (30-90 microM) significantly (p<0.05) inhibited the productions of NO and PGE(2) in LPS stimulated macrophages without inducing cytotoxicity. The effect of Neoandrographolide also has been investigated on iNOS and COX-2 expression in activated macrophage by using RT-PCR and immunoblotting. The inhibition of NO release by Neoandrographolide can be attributed to the block of iNOS mRNA transcription followed by inhibiting protein expression. However, Neoandrographolide inhibited COX-2 protein expression only but without inhibiting COX-2 mRNA expression, which was involved in the inhibitory activity against the PGE(2 )overproduction. This suggests that the effect of Neoandrographolide on iNOS expression may occur at the transcriptional level and the inhibition of COX-2 expression occurs at the translational level. Furthermore, we have found that the addition of Neoandrographolide inhibited the activation of p38 mitogen-activated protein kinase (MAPKs) instead of JNK, ERK1/2, or NF-kappaB. These results indicated that the anti-inflammatory properties of Neoandrographolide might result from the inhibition of iNOS and COX-2 expression through inhibiting p38 MAPKs activation. Therefore, Neoandrographolide isolated from A. paniculata could be offered as a leading compound for anti-inflammation.
In vivo and in vitro anti-inflammatory activities of neoandrographolide.[Pubmed:17436371]
Am J Chin Med. 2007;35(2):317-28.
Neoandrographolide, one of the principal diterpene lactones, isolated from a medicinal herb Andrographis paniculata Nees, was tested in vivo and in vitro for its anti-inflammatory activities and mechanism. Oral administration of Neoandrographolide (150 mg/kg) significantly suppressed ear edema induced by dimethyl benzene in mice. Oral administration of Neoandrographolide (100-150 mg/kg) also reduced the increase in vascular permeability induced by acetic acid in mice. In vitro studies were performed using the macrophage cell line RAW264.7 to study the effect of Neoandrographolide on suppressing phorbol-12-myristate-13-acetate (PMA)-stimulated respiratory bursts and lipopolysaccharide (LPS)-induced production of nitric oxide (NO) and tumor necrosis factor-alpha (TNF-alpha). Respiratory bursts were quantified by chemiluminescence (CL) measurements. Results showed that Neoandrographolide suppressed PMA-stimulated respiratory bursts dose-dependently from 30 muM to 150 muM. Neoandrographolide also inhibited NO and TNF-alpha production in LPS-induced macrophages, contributing to the anti-inflammatory activity of A. paniculata. These results indicate that Neoandrographolide possesses significant anti-inflammatory effects, which implies that it would be one of the major contributing components to participate in the anti-inflammatory effect of A. paniculata. and a potential candidate for further clinical trial.
