AucubinCAS# 479-98-1 |
Quality Control & MSDS
Number of papers citing our products
Chemical structure
3D structure
| Cas No. | 479-98-1 | SDF | Download SDF |
| PubChem ID | 91458 | Appearance | White powder |
| Formula | C15H22O9 | M.Wt | 346.33 |
| Type of Compound | Iridoids | Storage | Desiccate at -20°C |
| Synonyms | Aucuboside; Rhimantin | ||
| Solubility | DMSO : ≥ 31 mg/mL (89.51 mM) *"≥" means soluble, but saturation unknown. | ||
| Chemical Name | (2S,3R,4S,5S,6R)-2-[[(1S,4aR,5S,7aS)-5-hydroxy-7-(hydroxymethyl)-1,4a,5,7a-tetrahydrocyclopenta[c]pyran-1-yl]oxy]-6-(hydroxymethyl)oxane-3,4,5-triol | ||
| SMILES | C1=COC(C2C1C(C=C2CO)O)OC3C(C(C(C(O3)CO)O)O)O | ||
| Standard InChIKey | RJWJHRPNHPHBRN-FKVJWERZSA-N | ||
| 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 | Aucubin is an iridoid glycoside with a wide range of biological activities, including pancreas-protective, chondroprotective, antispasmodic, liver-protective, anti-inflammatory, anti-microbial, antioxidant, anti-algesic as well as anti-tumor activities. Aucubin prevents neuronal death in the hippocampal CA1 region in rats with diabetic encephalopathy, it also has protective effects on H2O2-induced apoptosis in PC12 cells. Aucubin may improve obesity-induced atherosclerosis by attenuating TNF-α-induced inflammatory responses. Aucubin suppresses hepatitis B viral DNA replication in vitro. |
| Targets | MMP(e.g.TIMP) | NOS | COX | NO | IL Receptor | NF-kB | TNF-α | ERK | IkB | ROS | HBV | DNA/RNA Synthesis | IKK |
| In vitro | Aucubin promotes neurite outgrowth in neural stem cells and axonal regeneration in sciatic nerves.[Pubmed: 25258571]Exp Neurobiol. 2014 Sep;23(3):238-45.Aucubin is an iridoid glycoside with a wide range of biological activities, including anti-inflammatory, anti-microbial, anti-algesic as well as anti-tumor activities. Recently, it has been shown that Aucubin prevents neuronal death in the hippocampal CA1 region in rats with diabetic encephalopathy. In addition, it has protective effects on H2O2-induced apoptosis in PC12 cells.
Aucubin, a naturally occurring iridoid glycoside inhibits TNF-α-induced inflammatory responses through suppression of NF-κB activation in 3T3-L1 adipocytes.[Pubmed: 23612013]Cytokine. 2013 Jun;62(3):407-12.Obesity is closely associated with a state of chronic, low-grade inflammation characterized by abnormal cytokine production and activation of inflammatory signaling pathways in adipose tissue.
Tumor necrosis factor (TNF)-α is chronically elevated in adipose tissues of obese rodents and humans. Increased levels of TNF-α are implicated in the induction of atherogenic adipokines, such as plasminogen activator inhibitor (PAI)-1, adipose-tissue-derived monocyte chemoattractant protein (MCP)-1, and interleukin (IL)-6. Aucubin, an iridoid glycoside existing in medicinal plants, has been reported to show an anti-inflammatory activity by suppression of TNF-α production in murine macrophages.
Liver-protective activities of aucubin derived from traditional oriental medicine.[Pubmed: 10100510]Res Commun Mol Pathol Pharmacol. 1998 Nov;102(2):189-204.The iridoid glycosides including Aucubin (AU), catalpol (CA), swertimarin (SW), and gardenoside (GA) are frequently found as natural constituents of many traditional oriental medicinal plants including Chinese herbs. Among these iridoid glycosides, AU was systematically studied for its potent liver-protective activities using experimental systems of hepatic damage. AU showed high liver-protective activity against carbon tetrachloride-induced hepatic damage in mice. Also AU showed significant protective activity against alpha-amanitin-induced hepatic damage in mice, and it prevented a depression of liver RNA biosynthesis caused by alpha-amanitin administration. Potent antidotal effects on mushroom poisoning in beagle dogs ingested with aqueous extract of Amanita virosa was observed; beagle dogs completely survived, even when AU administration was withheld for half an hour after mushroom poisoning. In addition, AU was found to suppress hepatitis B viral DNA replication in vitro. Conversion of AU to its aglycone form appeared to be a prerequisite step for an exhibition of such antiviral activity. |
| In vivo | Aucubin prevents interleukin-1 beta induced inflammation and cartilage matrix degradation via inhibition of NF-κB signaling pathway in rat articular chondrocytes.[Pubmed: 25576403]Int Immunopharmacol. 2015 Feb;24(2):408-15.Proinflammatory cytokine interleukin-1β (IL-1β) plays a crucial role in the pathogenesis of Osteoarthritis (OA) by stimulating several mediators contributed to cartilage degradation.
Aucubin, a natural compound derived from plants which has been shown to possess diverse biological activities including anti-inflammatory property, may benefit the IL-1β stimulated chondrocytes.
|
| Kinase Assay | In vitro antispasmodic activity of peracetylated penstemonoside, aucubin and catalpol.[Pubmed: 7809202]Planta Med. 1994 Dec;60(6):512-5.In vitro, the peracetates of penstemonoside, Aucubin and catalpol, iridoids isolated from Parentucellia latifolia, antagonize the uterine muscular contractions induced by acetylcholine and calcium, in a similar way to papaverine.
|
| Cell Research | Protective effects of aucubin isolated from Eucommia ulmoides against UVB-induced oxidative stress in human skin fibroblasts.[Pubmed: 15997107]Biol Pharm Bull. 2005 Jul;28(7):1244-8.Ultraviolet-B (UVB) irradiation has been demonstrated to produce reactive oxygen species (ROS) in the cells and skin, which induces the synthesis of matrix metalloproteinases (MMPs), causing skin photoaging.
|
| Animal Research | The promoting effects of geniposidic acid and aucubin in Eucommia ulmoides Oliver leaves on collagen synthesis.[Pubmed: 9881644]Antioxidant and pancreas-protective effect of aucubin on rats with streptozotocin-induced diabetes.[Pubmed: 18230397]Eur J Pharmacol. 2008 Mar 17;582(1-3):162-7.Oxidative stress has been suggested as a contributory factor in development and complication of diabetes.
The aim of the present study was to determine the protective effect of Aucubin on lipid peroxidation and activities of antioxidant defense systems and to conduct immunohistochemical evaluation of pancreas in streptozotocin-induced diabetic rats.
Biol Pharm Bull. 1998 Dec;21(12):1306-10.We have reported that collagen synthesis was stimulated by the administration of a hot water extract from the leaves of Eucommia ulmoides OLIVER, Eucommiaceae (Du-Zhong leaves) in false aged model rats.
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Aucubin Dilution Calculator
Aucubin Molarity Calculator
| 1 mg | 5 mg | 10 mg | 20 mg | 25 mg | |
| 1 mM | 2.8874 mL | 14.4371 mL | 28.8742 mL | 57.7484 mL | 72.1855 mL |
| 5 mM | 0.5775 mL | 2.8874 mL | 5.7748 mL | 11.5497 mL | 14.4371 mL |
| 10 mM | 0.2887 mL | 1.4437 mL | 2.8874 mL | 5.7748 mL | 7.2185 mL |
| 50 mM | 0.0577 mL | 0.2887 mL | 0.5775 mL | 1.155 mL | 1.4437 mL |
| 100 mM | 0.0289 mL | 0.1444 mL | 0.2887 mL | 0.5775 mL | 0.7219 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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Aucubin is an iridoid glycoside with a wide range of biological activities, including anti-inflammatory, anti-microbial, anti-algesic as well as anti-tumor activities. IC50 value: Target: In vitro: Aucubin promotes neuronal differentiation and neurite outgrowth in neural stem cells cultured primarily from the rat embryonic hippocampus [1]. Aucubin significantly reversed the elevated gene and protein expression of MMP-3, MMP-9, MMP-13, iNOS, COX-2 and the production of NO induced by IL-1β challenge in rat chondrocytes [2]. In vivo:
References:
[1]. Sheng-nan Wang, et al. Aucubin prevents interleukin-1 beta induced inflammation and cartilage matrix degradation via inhibition of NF-κB signaling pathway in rat articular chondrocytes. International Immunopharmacology, Volume 24, Issue 2, February 2015
[2]. Xue B, et al. Pharmacokinetics and tissue distribution of Aucubin, Ajugol and Catalpol in rats using a validated simultaneous LC-ESI-MS/MS assay. J Chromatogr B Analyt Technol Biomed Life Sci. 2015 Oct 1;1002:245-53.
[3]. Shirley KP, et al. In Vitro Effects of Plantago Major Extract, Aucubin, and Baicalein on Candida Albicans Biofilm Formation, Metabolic Activity, and Cell Surface Hydrophobicity. J Prosthodont. 2015 Nov 30.
[4]. Yong Min Kim, et al. Aucubin Promotes Neurite Outgrowth in Neural Stem Cells and Axonal Regeneration in Sciatic Nerves. Exp Neurobiol. 2014 Sep; 23(3): 238–245.
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Aucubin prevents interleukin-1 beta induced inflammation and cartilage matrix degradation via inhibition of NF-kappaB signaling pathway in rat articular chondrocytes.[Pubmed:25576403]
Int Immunopharmacol. 2015 Feb;24(2):408-415.
Proinflammatory cytokine interleukin-1beta (IL-1beta) plays a crucial role in the pathogenesis of Osteoarthritis (OA) by stimulating several mediators contributed to cartilage degradation. Aucubin, a natural compound derived from plants which has been shown to possess diverse biological activities including anti-inflammatory property, may benefit the IL-1beta stimulated chondrocytes. The present study was aimed to investigate the effects of Aucubin on IL-1beta stimulated rat chondrocytes. Rat chondrocytes were cultured and pretreated with Aucubin (1, 10, 20, 50muM), and then stimulated with or without IL-1beta (10ng/ml). Gene and protein expression of MMP-3, MMP-9, MMP-13, cyclooxygenase-2 (COX-2), inducible nitric oxide synthase (iNOS) was determined by real-time PCR and Western blotting respectively. Nitric oxide (NO) production was quantified by Griess reagent. Phosphorylation and nuclear translocation of p65 were detected by western blotting and immunofluorescence, respectively. We found that Aucubin significantly reversed the elevated gene and protein expression of MMP-3, MMP-9, MMP-13, iNOS, COX-2 and the production of NO induced by IL-1beta challenge in rat chondrocytes. Furthermore, Aucubin was able to suppress the IL-1beta-mediated phosphorylation and nuclear translocation of p65, indicating Aucubin may possibly act via the NF-kappaB signaling pathway. The present study proposes that Aucubin may be a potential therapeutic choice in the treatment of OA due to its anti-inflammatory and chondroprotective features.
Antioxidant and pancreas-protective effect of aucubin on rats with streptozotocin-induced diabetes.[Pubmed:18230397]
Eur J Pharmacol. 2008 Mar 17;582(1-3):162-7.
Oxidative stress has been suggested as a contributory factor in development and complication of diabetes. The aim of the present study was to determine the protective effect of Aucubin on lipid peroxidation and activities of antioxidant defense systems and to conduct immunohistochemical evaluation of pancreas in streptozotocin-induced diabetic rats. Lipid peroxidation was determined by assessing the concentration of malondialdehyde and activities of antioxidant enzymes - catalase, glutathione peroxidase and superoxide dismutase in liver and kidneys of rats were determined. Changes of blood glucose and immunohistochemical evaluation on pancreas were also investigated as part of the pathology of diabetes. In our study, Aucubin treatment lowered blood glucose. Diabetic rats exhibited an increase in the level of lipid peroxidation and decrease in activities of antioxidant enzymes in liver and kidneys as compared to control rats. Administration of Aucubin to diabetic rats for 15 days significantly reversed damage associated with diabetes. In addition, diabetic rats showed an obvious decrease in insulin immunoreactivity and the number of beta cells in pancreas, but the pancreas of Aucubin-treated rats were improved and the number of immunoreactive beta cells were significantly increased. These results indicated that Aucubin may have value as a safe preventive or therapeutic agent against diabetes mellitus.
The promoting effects of geniposidic acid and aucubin in Eucommia ulmoides Oliver leaves on collagen synthesis.[Pubmed:9881644]
Biol Pharm Bull. 1998 Dec;21(12):1306-10.
We have reported that collagen synthesis was stimulated by the administration of a hot water extract from the leaves of Eucommia ulmoides OLIVER, Eucommiaceae (Du-Zhong leaves) in false aged model rats. In this paper, we set out to examine the compounds in Du-Zhong leaves that stimulated collagen synthesis in false aged model rats. In experiment 1, a methanol extract of Du-Zhong leaves also stimulated collagen synthesis in aged model rats. An acetone fraction was derived from the methanol extract by silica gel chromatography in experiment 2. The acetone fraction mainly contained iridoides mono-glycosides such as geniposidic acid and Aucubin. The administration of geniposidic acid or Aucubin stimulated collagen synthesis in aged model rats in experiments 3 and 4 (significance (p<0.05)). The reported pharmacological effects of Du-Zhong leaves, including healing organs and strengthening bone and muscle, are closely related to collagen metabolism. It appears that geniposidic acid and Aucubin are the actual compounds in Du-Zhong which caused the effect in our experiments.
Protective effects of aucubin isolated from Eucommia ulmoides against UVB-induced oxidative stress in human skin fibroblasts.[Pubmed:15997107]
Biol Pharm Bull. 2005 Jul;28(7):1244-8.
Ultraviolet-B (UVB) irradiation has been demonstrated to produce reactive oxygen species (ROS) in the cells and skin, which induces the synthesis of matrix metalloproteinases (MMPs), causing skin photoaging. Using the human skin fibroblast HS68 cell line in the present study, we investigated the photoprotective effects of Aucubin from Eucommia ulmoides. Pretreatment with Aucubin significantly inhibited the production of MMP-1 by 57% when compared to the UVB-irradiated cells. Additionally, the senescence-associated beta-galactosidase (SA beta-gal) activity was markedly decreased in the presence of Aucubin, which indicates it as an antiphoto-induced aging compound. As the effect of Aucubin was determined against ROS, the inhibited ROS formation and malondialdehyde (MDA) levels, and the increased cell viability and glutathione (GSH) level were observed with Aucubin under UVB irradiation. Based upon these results, it was suggested that Aucubin might play an important role in the cellular defense mechanism against UV radiation-induced photoaging. An understanding of the antioxidant properties of Aucubin could, in part, act to elucidate its protective mechanism on the human skin photoaging.
Liver-protective activities of aucubin derived from traditional oriental medicine.[Pubmed:10100510]
Res Commun Mol Pathol Pharmacol. 1998 Nov;102(2):189-204.
The iridoid glycosides including Aucubin (AU), catalpol (CA), swertimarin (SW), and gardenoside (GA) are frequently found as natural constituents of many traditional oriental medicinal plants including Chinese herbs. Among these iridoid glycosides, AU was systematically studied for its potent liver-protective activities using experimental systems of hepatic damage. AU showed high liver-protective activity against carbon tetrachloride-induced hepatic damage in mice. Also AU showed significant protective activity against alpha-amanitin-induced hepatic damage in mice, and it prevented a depression of liver RNA biosynthesis caused by alpha-amanitin administration. Potent antidotal effects on mushroom poisoning in beagle dogs ingested with aqueous extract of Amanita virosa was observed; beagle dogs completely survived, even when AU administration was withheld for half an hour after mushroom poisoning. In addition, AU was found to suppress hepatitis B viral DNA replication in vitro. Conversion of AU to its aglycone form appeared to be a prerequisite step for an exhibition of such antiviral activity.
Aucubin promotes neurite outgrowth in neural stem cells and axonal regeneration in sciatic nerves.[Pubmed:25258571]
Exp Neurobiol. 2014 Sep;23(3):238-45.
Aucubin is an iridoid glycoside with a wide range of biological activities, including anti-inflammatory, anti-microbial, anti-algesic as well as anti-tumor activities. Recently, it has been shown that Aucubin prevents neuronal death in the hippocampal CA1 region in rats with diabetic encephalopathy. In addition, it has protective effects on H2O2-induced apoptosis in PC12 cells. We have shown here that Aucubin promotes neuronal differentiation and neurite outgrowth in neural stem cells cultured primarily from the rat embryonic hippocampus. We also investigated whether Aucubin facilitates axonal elongation in the injured peripheral nervous system. Aucubin promoted lengthening and thickness of axons and re-myelination at 3 weeks after sciatic nerve injury. These results indicate that administration of Aucubin improved nerve regeneration in the rat model of sciatic nerve injury, suggesting that Aucubin may be a useful therapeutic compound for the human peripheral nervous system after various nerve injuries.
Aucubin, a naturally occurring iridoid glycoside inhibits TNF-alpha-induced inflammatory responses through suppression of NF-kappaB activation in 3T3-L1 adipocytes.[Pubmed:23612013]
Cytokine. 2013 Jun;62(3):407-12.
Obesity is closely associated with a state of chronic, low-grade inflammation characterized by abnormal cytokine production and activation of inflammatory signaling pathways in adipose tissue. Tumor necrosis factor (TNF)-alpha is chronically elevated in adipose tissues of obese rodents and humans. Increased levels of TNF-alpha are implicated in the induction of atherogenic adipokines, such as plasminogen activator inhibitor (PAI)-1, adipose-tissue-derived monocyte chemoattractant protein (MCP)-1, and interleukin (IL)-6. Aucubin, an iridoid glycoside existing in medicinal plants, has been reported to show an anti-inflammatory activity by suppression of TNF-alpha production in murine macrophages. The present study is aimed to investigate the effects of Aucubin on TNF-alpha-induced atherogenic changes of the adipokines in differentiated 3T3-L1 cells. Aucubin significantly inhibited TNF-alpha-induced secretion and mRNA synthesis of the atherogenic adipokines including PAI-1, MCP-1, and IL-6. Further investigation of the molecular mechanism revealed that pretreatment with Aucubin suppressed extracellular signal-regulated kinase (ERK) activation, inhibitory kappa Balpha (IkappaBalpha) degradation, and subsequent nuclear factor kappa B (NF-kappaB) activation. These findings suggest that Aucubin may improve obesity-induced atherosclerosis by attenuating TNF-alpha-induced inflammatory responses.
In vitro antispasmodic activity of peracetylated penstemonoside, aucubin and catalpol.[Pubmed:7809202]
Planta Med. 1994 Dec;60(6):512-5.
In vitro, the peracetates of penstemonoside, Aucubin and catalpol, iridoids isolated from Parentucellia latifolia, antagonize the uterine muscular contractions induced by acetylcholine and calcium, in a similar way to papaverine. The antagonism is non-competitive against acetylcholine (pD2' values: 5.60 for the peracetates of penstemonoside, 5.74 for Aucubin, 5.59 for catalpol, and 5.32 for papaverine) and competitive against calcium (pA2 values: 6.60 for the peracetates of penstemonoside, 6.34 for Aucubin, 6.48 for catalpol, and 6.23 for papaverine). The two components, phasic and tonic, of the response of the vas deferens to potassium are reduced by the three iridoids. The reduction is similar for both phases. The antispasmodic activity of the three iridoids, similar to papaverine, is related to an inhibiting effect of extracellular calcium, intracellular or both.
