Picroside IICAS# 39012-20-9 |
Quality Control & MSDS
Number of papers citing our products
Chemical structure
3D structure
| Cas No. | 39012-20-9 | SDF | Download SDF |
| PubChem ID | 3081484 | Appearance | Beige powder |
| Formula | C23H28O13 | M.Wt | 512.47 |
| Type of Compound | Iridoids | Storage | Desiccate at -20°C |
| Synonyms | Amphicoside II; 6-Vanillylcatalpol | ||
| Solubility | Methanol : 125 mg/mL (243.92 mM; Need ultrasonic) DMSO : 100 mg/mL (195.14 mM; Need ultrasonic) | ||
| Chemical Name | [1a-(hydroxymethyl)-2-[3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy-2,5a,6,6a-tetrahydro-1bH-oxireno[5,6]cyclopenta[1,3-c]pyran-6-yl] 4-hydroxy-3-methoxybenzoate | ||
| SMILES | COC1=C(C=CC(=C1)C(=O)OC2C3C=COC(C3C4(C2O4)CO)OC5C(C(C(C(O5)CO)O)O)O)O | ||
| Standard InChIKey | AKNILCMFRRDTEY-UHFFFAOYSA-N | ||
| Standard InChI | InChI=1S/C23H28O13/c1-31-12-6-9(2-3-11(12)26)20(30)34-18-10-4-5-32-21(14(10)23(8-25)19(18)36-23)35-22-17(29)16(28)15(27)13(7-24)33-22/h2-6,10,13-19,21-22,24-29H,7-8H2,1H3 | ||
| 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 | Picroside II has antioxidant, anti-inflammatory, immune regulatory, anti-virus and other pharmacological activities. It has potent anti-apoptotic activity against renal I/R injury by suppressing the TLR4/NF-κB signaling pathway, it can protect the ischemic kidney against renal fibrosis and improve the neurological function of rats upon cerebral ischemia reperfusion injury. Picroside II enhances nerve growth factor (NGF)-induced neurite outgrowth from PC12D cells by amplifying a down-stream step of MAP kinase in the NGF receptor-mediated intracellular MAP kinase-dependent signaling pathway. |
| Targets | Bcl-2/Bax | PARP | TLR | NF-kB | p65 | TNF-α | IL Receptor | MAPK | Caspase | ROS | MMP(e.g.TIMP) | COX |
| In vitro | Inhibitory effect of picroside II on hepatocyte apoptosis.[Pubmed: 15916740 ]Acta Pharmacol Sin. 2005 Jun;26(6):729-36.To investigate the influence of Picroside II on hepatocyte apoptosis and its mechanism.
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| In vivo | Picroside II protects rat kidney against ischemia/reperfusion-induced oxidative stress and inflammation by the TLR4/NF-κB pathway.[Pubmed: 25780418]Exp Ther Med. 2015 Apr;9(4):1253-1258.Picroside II possesses a wide range of pharmacological effects and has been demonstrated to ameliorate cerebral ischemia and reperfusion (I/R) injury. However, its effects on renal I/R injury remain unclear. In the present study, the role of Picroside II in attenuating oxidative stress and the inflammatory response in a rat model of renal I/R injury was investigated.
Neuroprotective properties of picroside II in a rat model of focal cerebral ischemia.[Pubmed: 21151457 ]Int J Mol Sci. 2010 Nov 16;11(11):4580-90.
The aim of this study was to explore the effect of Picroside II on neuronal apoptosis and the expression of caspase-3 and poly ADP-ribose polymerase (PARP) following middle cerebral artery occlusion/reperfusion in male Wistar rats.
The anti-inflammatory effect of picroside II and the optimizing of therapeutic dose and time window in cerebral ischemic injury in rats[Reference: WebLink]Modern Research in Inflammation, 2013, 02(3):46-53.The aim is to optimize the anti-inflammatory effect and the therapeutic dose and time window of picrosede II by orthogonal test in cerebral ischemic injury in rats.
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| Kinase Assay | Potentiation of nerve growth factor-action by picrosides I and II, natural iridoids, in PC12D cells.[Pubmed: 11020482]Eur J Pharmacol. 2000 Oct 13;406(2):203-8.Natural iridoid, picroside I (beta-D-glucopyranoside, 1a,1b,2,5a,6, 6a-hexahydro-6-hydroxy-1a-(hydroxymethyl)oxireno[4,5]cyclopenta[1, 2-c]pyran-2-yl, 6-(3-phenyl-2-propenoate)) o rPicroside II (beta-D-glucopyranoside, 1a,1b,2,5a,6, 6a-hexahydro-6-[(4-hydroxy-3-methoxybenzoyl)oxy]-1a-(hydroxymethyl )ox ireno[4,5]cyclopenta[1,2-c]pyran-2-yl) alone did not exhibit neuritogenic activity, but caused a concentration-dependent (>0.1 microM) enhancement of nerve growth factor (NGF, 2 ng/ml)-induced neurite outgrowth from PC12D cells.
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| Cell Research | Picroside II attenuates fatty acid accumulation in HepG2 cells via modulation of fatty acid uptake and synthesis.[Pubmed: 29254285 ]Clin Mol Hepatol. 2018 Mar;24(1):77-87.Cell lines:HepG2 cells |
| Animal Research | Picroside II protects the blood-brain barrier by inhibiting the oxidative signaling pathway in cerebral ischemia-reperfusion injury.[Pubmed: 28388666]PLoS One. 2017 Apr 7;12(4):e0174414.Animal Models: Adult male Wistar rats |
Picroside II Dilution Calculator
Picroside II Molarity Calculator
| 1 mg | 5 mg | 10 mg | 20 mg | 25 mg | |
| 1 mM | 1.9513 mL | 9.7567 mL | 19.5133 mL | 39.0267 mL | 48.7833 mL |
| 5 mM | 0.3903 mL | 1.9513 mL | 3.9027 mL | 7.8053 mL | 9.7567 mL |
| 10 mM | 0.1951 mL | 0.9757 mL | 1.9513 mL | 3.9027 mL | 4.8783 mL |
| 50 mM | 0.039 mL | 0.1951 mL | 0.3903 mL | 0.7805 mL | 0.9757 mL |
| 100 mM | 0.0195 mL | 0.0976 mL | 0.1951 mL | 0.3903 mL | 0.4878 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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Effect of picroside II on apoptosis induced by renal ischemia/reperfusion injury in rats.[Pubmed:25667634]
Exp Ther Med. 2015 Mar;9(3):817-822.
Renal ischemia and reperfusion (I/R) injury, which commonly occurs in kidney transplantation, is the leading cause of acute kidney injury. Picroside II possesses a wide range of pharmacological effects, including anti-apoptosis effects. In the present study, the ability of Picroside II to attenuate apoptosis in a rat model of renal I/R injury was investigated. Sprague-Dawley rats were subjected to 45 min of ischemia followed by 24 h of reperfusion. Prior to reperfusion, the rats were treated with Picroside II or an equal volume of phosphate-buffered saline. It was observed that renal function was significantly improved by the treatment with Picroside II. Morphological analysis indicated that Picroside II markedly reduced tissue damage and the expression of cleaved caspase-3. Reverse transcription-quantitative polymerase chain reaction and western blotting revealed that the expression levels of Bax and poly(ADP-ribose) polymerase-1 (PARP-1) were upregulated in the I/R group, whereas those of Bcl-2 were downregulated. However, the treatment with Picroside II inhibited these changes induced by renal I/R injury. In conclusion, Picroside II has potent anti-apoptotic activity against renal I/R injury.
Picroside II protects rat kidney against ischemia/reperfusion-induced oxidative stress and inflammation by the TLR4/NF-kappaB pathway.[Pubmed:25780418]
Exp Ther Med. 2015 Apr;9(4):1253-1258.
Picroside II possesses a wide range of pharmacological effects and has been demonstrated to ameliorate cerebral ischemia and reperfusion (I/R) injury. However, its effects on renal I/R injury remain unclear. In the present study, the role of Picroside II in attenuating oxidative stress and the inflammatory response in a rat model of renal I/R injury was investigated. Sprague Dawley rats were subjected to 45 min of ischemia followed by 24 h of reperfusion. Prior to reperfusion, the rats were treated with Picroside II or an equal volume of phosphate-buffered saline. Renal function and histological changes were compared and the relevant parameters of oxidative stress and inflammation were detected. The expression of toll-like receptor 4 (TLR4) and nuclear factor kappaB (NF-kappaB; p65) were assessed by immunohistochemistry and western blotting. It was observed that renal function was significantly improved by treatment with Picroside II. Morphological analysis indicated that Picroside II clearly reduced tissue damage and the expression of TLR4 and NF-kappaB. Reverse transcription-quantitative polymerase chain reaction demonstrated that Picroside II inhibited the increase of tumor necrosis factor (TNF)-alpha, interleukin (IL)-1beta and intercellular adhesion molecule (ICAM)-1 expression induced by I/R injury. Western blot analysis indicated that the expression levels of TLR4 and NF-kappaB were significantly downregulated in the Picroside II group compared with those in the I/R group. These results indicate that Picroside II treatment suppressed the TLR4/NF-kappaB signaling pathway, protecting renal tissue against I/R-induced oxidative stress and inflammatory response.
Neuroprotective properties of picroside II in a rat model of focal cerebral ischemia.[Pubmed:21151457]
Int J Mol Sci. 2010 Nov 16;11(11):4580-90.
The aim of this study was to explore the effect of Picroside II on neuronal apoptosis and the expression of caspase-3 and poly ADP-ribose polymerase (PARP) following middle cerebral artery occlusion/reperfusion in male Wistar rats. Picroside II (10 mg/kg) was administered intravenously into the tail vein of the animals. The neurological function deficits were evaluated with the Bederson's test and the cerebral infarction volume was visualized with tetrazolium chloride (TTC) staining. The apoptotic cells were counted by in situ terminal deoxynucleotidyl transferase-mediated biotinylated deoxyuridine triphosphate nick end labeling (TUNEL) assay. The immunohistochemistry stain and enzyme linked immunosorbent assay (ELISA) was used to determine the expressions of caspase-3 and PARP in brain tissue. The results indicated that rats in the control group showed neurological function deficit and cerebral infarction in ischemic hemisphere after two hours ischemia followed by 22 hours reperfusion. Caspase-3 and PARP expressions were also profound in the cortex, the striatum and the hippocampus, along with increased apoptotic cells in this group. Bederson's score, infarction volume, and expressions of caspase-3 and PARP, as well as apoptosis in the treatment group were, however, significantly decreased compared to those in the control group indicating that intravenous treatment with Picroside II might be beneficial to inhibit neuronal apoptosis and, thus, to improve the neurological function of rats upon cerebral ischemia reperfusion injury.
Potentiation of nerve growth factor-action by picrosides I and II, natural iridoids, in PC12D cells.[Pubmed:11020482]
Eur J Pharmacol. 2000 Oct 13;406(2):203-8.
Natural iridoid, picroside I (beta-D-glucopyranoside, 1a,1b,2,5a,6, 6a-hexahydro-6-hydroxy-1a-(hydroxymethyl)oxireno[4,5]cyclopenta[1, 2-c]pyran-2-yl, 6-(3-phenyl-2-propenoate)) or II (beta-D-glucopyranoside, 1a,1b,2,5a,6, 6a-hexahydro-6-[(4-hydroxy-3-methoxybenzoyl)oxy]-1a-(hydroxymethyl )ox ireno[4,5]cyclopenta[1,2-c]pyran-2-yl) alone did not exhibit neuritogenic activity, but caused a concentration-dependent (>0.1 microM) enhancement of nerve growth factor (NGF, 2 ng/ml)-induced neurite outgrowth from PC12D cells. The picroside-induced enhancing action of NGF was abolished by GF109203X (2-[1-(3-dimethylaminopropyl)-indol-3-yl]-3-(indol-3-yl)maleimide) (0.1 microM), a protein kinase C inhibitor. Furthermore, PD98059 (2-(2'-amino-3'-methoxyphenyl)-oxanaphthalen-4-one) (20 microM), a potent mitogen-activated protein (MAP) kinase kinase inhibitor, completely blocked the picroside-induced enhancement of neurite outgrowth in the presence of NGF (2 ng/ml), suggesting that picrosides activate the MAP kinase-dependent signaling pathway. Interestingly, no increase in the expression of phosphorylated MAP kinase was observed in picroside-treated (60 microM) PC12D cells in the presence of NGF (2 ng/ml). These results suggest that picroside I or II enhances NGF-induced neurite outgrowth from PC12D cells, probably by amplifying a down-stream step of MAP kinase in the NGF receptor-mediated intracellular MAP kinase-dependent signaling pathway.
The protective effect of picroside II against hypoxia/reoxygenation injury in neonatal rat cardiomyocytes.[Pubmed:22880952]
Pharm Biol. 2012 Oct;50(10):1226-32.
CONTEXT: Picroside II, an iridoid glucoside found in the root of Picrorhiza scrophulariiflora Pennell (Scrophulariaceae), has been demonstrated to possess potent antioxidant activity. However, whether Picroside II has a protective effect against hypoxia/reoxygenation (H/R)-induced cardiomyocyte injury is poorly understood. OBJECTIVE: To explore the cardioprotective role of Picroside II against oxidative stress induced by H/R injury in neonatal rat cardiacmyocytes. MATERIALS AND METHODS: The viability and cellular damage of cardiomyocytes were assessed by 3-(4,5-dimethylthiazol-2-yl)-2,5-diphenyltetrazolim bromide (MTT) and lactate dehydrogenase (LDH) assays, respectively. The activities of superoxide dismutase (SOD) and glutathione peroxidase (GSH-Px), the levels of reduced (GSH) and oxidized glutathione (GSSG), and the contents of malondialdehyde (MDA) were determined by a colorimetric method. The levels of intracellular reactive oxygen species (ROS) and calcium were evaluated by flow cytometric analysis. RESULTS: We analyzed the effective half-maximal concentration for protection from the dose-response curves and obtained the concentration of 50 microg/mL as EC(50). Pretreated cardiomyocytes with Picroside II (50-200 microg/mL), prior to H/R exposure, inhibited LDH activity in culture media and increased cell viability in a dose-dependent manner. This protective effect was accompanied by significantly increasing reduced GSH contents and the activities of SOD and GSH-Px and attenuating MDA and GSSG contents in response to H/R injury. Furthermore, treatment with Picroside II also inhibited ROS production and calcium accumulation in cardiomyocytes. DISCUSSION AND CONCLUSION: The present study demonstrates that Picroside II protects cardiomyocytes against oxidative-stress injury induced by H/R through reduction of ROS production and calcium accumulation and enhancement of the activity of antioxidant defense.
Inhibitory effect of picroside II on hepatocyte apoptosis.[Pubmed:15916740]
Acta Pharmacol Sin. 2005 Jun;26(6):729-36.
AIM: To investigate the influence of Picroside II on hepatocyte apoptosis and its mechanism. METHODS: Morphological changes and quantification of apoptotic cells were determined under transmission electron microscopy and flow cytometry respectively. DNA fragmentation was visualized by agarose gel electrophoresis. Semi-quantitative reverse transcription-PCR (RT-PCR) was used to analyze the expression of bcl-2 and bax genes. The content of manganese-superoxide dismutase (SOD) in liver mitochondria was detected by the Marland method. The content of malonic aldehyde (MDA) and the protein level in liver tissue were determined by thiobarbituric acid colorimetry and Lowry method. RESULTS: Picroside II decreased the levels of alanine aminotransferase and aspartate aminotransferase in the serum resulting from acute-liver injured mice induced with D-GalN and LPS; it also reduced the content of MDA, and thus, enhanced the activity of SOD. Picroside II 10 mg/kg was found to protect hepatocytes against apoptosis in a dose-dependent manner; it up-regulated the expression of bcl-2 genes, thus increased the bcl-2/bax ratio. CONCLUSION: Picroside II can protect hepatocytes against injury and prevent hepatocytes from apoptosis. It might by upregulating the bcl-2 gene expression and antioxidation.
