Obtusifolin

CAS# 477-85-0

Obtusifolin

Catalog No. BCN2537----Order now to get a substantial discount!

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Quality Control of Obtusifolin

Number of papers citing our products

Chemical structure

Obtusifolin

3D structure

Chemical Properties of Obtusifolin

Cas No. 477-85-0 SDF Download SDF
PubChem ID 3083575 Appearance Yellow powder
Formula C16H12O5 M.Wt 284.27
Type of Compound Anthraquinones Storage Desiccate at -20°C
Solubility Soluble in chloroform
Chemical Name 2,8-dihydroxy-1-methoxy-3-methylanthracene-9,10-dione
SMILES CC1=C(C(=C2C(=C1)C(=O)C3=C(C2=O)C(=CC=C3)O)OC)O
Standard InChIKey NYRXUBDGDSRBGB-UHFFFAOYSA-N
Standard InChI InChI=1S/C16H12O5/c1-7-6-9-12(16(21-2)13(7)18)15(20)11-8(14(9)19)4-3-5-10(11)17/h3-6,17-18H,1-2H3
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.
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.
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.

Source of Obtusifolin

1 Gnaphalium sp.

Biological Activity of Obtusifolin

DescriptionObtusifolin is a novel anti-breast-cancer bone metastasis agent, which has antioxidant, and antinociceptive properties.Obtusifolin has beneficial effects on the development of diabetic retinopathy via inhibition of accumulation of oxidatively modified DNA and nitrotyrosine in the retina, can help prevent vision loss in diabetic patients. Gluco-Obtusifolin and its aglycone may be useful for the treatment of cognitive impairment, and that its beneficial effects are mediated, in part, by the enhancement of cholinergic signaling.
TargetsSOD | NO | TNF-α | NF-kB | IL Receptor
In vitro

Obtusifolin suppresses phthalate esters-induced breast cancer bone metastasis by targeting parathyroid hormone-related protein.[Pubmed: 25415928]

J Agric Food Chem. 2014 Dec 10;62(49):11933-40.

This study is the first to demonstrate that parathyroid hormone-related protein (PTHrP), produced by human breast cancer cells after exposure to phthalate esters, contributes to bone metastasis by increasing osteoclastogenesis.
METHODS AND RESULTS:
This is also the first to reveal that Obtusifolin reverses phthalate esters-mediated bone resorption. Human breast cancer cells were treated with dibutyl phthalate (DBP), harvested in conditioned medium, and cultured to osteoblasts or osteoclasts. Cultures of osteoblasts with DBP-MDA-MB-231-CM increased the osteoclastogenesis activator RANKL (receptor activator of nuclear factor κ-B ligand) and M-CSF (macrophage colony-stimulating factor). PTHrP was secreted in MDA-MB-231 cells. DBP-MDA-MB-231-CM reduced osteoblasts to produce osteoprotegerin, an osteoclastogenesis inhibitor, while DBP mediated PTHrP up-regulation, increasing IL-8 secretion in MDA-MB-231 and contributing to breast cancer-mediated osteoclast differentiation and bone resorption. Obtusifolin, a major bioactive compound present in Cassia tora L., suppressed phthalate esters-mediated bone resorption.
CONCLUSIONS:
Therefore, Obtusifolin may be a novel anti-breast-cancer bone metastasis agent.

In vivo

Effect of obtusifolin administration on retinal capillary cell death and the development of retinopathy in diabetic rats.[Pubmed: 25030406]

Cell Biochem Biophys. 2014 Dec;70(3):1655-61.

Oxidative stress is increased in the retina in diabetes, and it is considered to play an important role in the development of retinopathy. Findings indicate that Obtusifolin has antioxidant properties. The purpose of this study was to examine the effect of Obtusifolin on retinal capillary cell apoptosis and the development of pathology in diabetes.
METHODS AND RESULTS:
Retina was used from streptozotocin-induced diabetic rats receiving diets supplemented with or without Obtusifolin (100, 200, and 400 mg/kg) for 11 months of diabetes. Capillary cell apoptosis (by terminal transferase-mediated dUTP nick-end labeling) and formation of acellular capillaries were investigated in the trypsin-digested retinal microvessels. The effect of Obtusifolin administration on retinal 8-hydroxy-2'deoxyguanosine (8-OHdG) and nitrotyrosine levels was determined by enzyme-linked immunosorbent assay. Obtusifolin administration for the entire duration of diabetes inhibited capillary cell apoptosis and the number of acellular capillaries in the retina, despite similar severity of hyperglycemia in the four diabetic groups (with and without Obtusifolin). Retinal 8-OHdG and nitrotyrosine levels were significantly increased, respectively, in diabetes, and Obtusifolin administration inhibited these increases.
CONCLUSIONS:
Our results demonstrate that the long-term administration of Obtusifolin has beneficial effects on the development of diabetic retinopathy via inhibition of accumulation of oxidatively modified DNA and nitrotyrosine in the retina. Obtusifolin represents an achievable adjunct therapy to help prevent vision loss in diabetic patients.

Anti-allodynic effects of obtusifolin and gluco-obtusifolin against inflammatory and neuropathic pain.[Pubmed: 25070277 ]

Biol Pharm Bull. 2014;37(10):1606-16.

Inflammatory pain and neuropathic pain are major health issues that represent considerable social and economic burden worldwide.
METHODS AND RESULTS:
In this study we investigated the potential of Obtusifolin and gluco-Obtusifolin, two anthraquinones found in the seeds of the widely used traditional Chinese medical botanical Cassia obtusifolia, to reduce neuropathic and inflammatory pain. The potential analgesic effects of Obtusifolin and gluco-Obtusifolin were evaluated by mice formalin test and complete Freund's adjuvant (CFA)-induced nociceptive behaviors in rats. Chronic constriction injury (CCI), L5 spinal nerve ligation (L5 SNL), diabetes, and chemotherapeutics inducing allodynia were used to test whether repeated treatment with Obtusifolin and gluco-Obtusifolin ameliorated neuropathic pain. Finally, we explored whether Obtusifolin and gluco-Obtusifolin altered the degree of neuroinflammation in rat spinal cord after CFA administration and CCI induction. Obtusifolin and gluco-Obtusifolin (0.25, 0.5, 1, and 2 mg/kg) reduced licking/biting time in dose-dependent manner in phase 2 of formalin-induced behavior in mice. Furthermore, repeated administration of Obtusifolin and gluco-Obtusifolin (0.25, 0.5, 1, and 2 mg/kg) reversed mechanical allodynia induced by CFA, CCI, L5 SNL, diabetes, and oxaliplatin in a dose-dependent manner in rats. Levels of activated nuclear factor-kappa B (NF-κB) and proinflammatory cytokines (interleukin (IL)-1β, IL-6, tumor necrosis factor α (TNF-α)) in lumbar spinal cord were elevated in rats following CFA treatment and CCI induction, and Obtusifolin and gluco-Obtusifolin significantly inhibited these effects.
CONCLUSIONS:
Our results demonstrate that Obtusifolin and gluco-Obtusifolin produce significant antinociceptive action in rodent behavioral models of inflammatory/neuropathic pain, and that this activity is associated with modulation of neuroinflammation in spinal cord.

Protocol of Obtusifolin

Animal Research

Gluco-obtusifolin and its aglycon, obtusifolin, attenuate scopolamine-induced memory impairment.[Pubmed: 19834282]

Obtusifolin treatment improves hyperlipidemia and hyperglycemia: possible mechanism involving oxidative stress.[Pubmed: 25015065]

Cell Biochem Biophys. 2014 Dec;70(3):1751-7.

Clinical research has confirmed the efficacy of several plant extracts in the modulation of oxidative stress associated with hyperlipidemia and hyperglycemia induced by obesity and diabetes. Findings indicate that Obtusifolin has antioxidant properties. The aim of this study was to evaluate the possible protective effects of Obtusifolin against oxidative damage in diabetic hyperlipidemia and hyperglycemia.
METHODS AND RESULTS:
In this study, the rats were divided into the following groups with eight animals in each: control, untreated diabetic, three Obtusifolin (10, 30, and 90 mg/kg/day)-treated diabetic groups. Diabetes was induced by streptozotocin (STZ) in rats. STZ was injected intraperitoneally at a single dose of 60 mg/kg for diabetes induction. Obtusifolin (intraperitoneal injection) was administered 3 days after STZ administration; these injections were continued to the end of the study (4 weeks). At the end of the 4-week period, blood was drawn for biochemical assays. In order to determine the changes of cellular antioxidant defense systems, antioxidant enzymes including glutathione peroxidase (GPx), superoxide dismutase (SOD), and catalase (CAT) activities were measured in serum. Moreover, we also measured serum nitric oxide (NO) and serum malondialdehyde (MDA) levels, markers of lipid peroxidation. STZ-induced diabetes caused an elevation (P < 0.001) of blood glucose, MDA, NO, total lipids, triglycerides and cholesterol, with reduction of GSH level and CAT and SOD activities. The results indicated that the significant elevation in the blood glucose, MDA, NO, total lipids, triglycerides and cholesterol; also the reduction of glutathione level and CAT and SOD activity were ameliorated in the Obtusifolin-treated diabetic groups compared with the untreated groups, in a dose-dependent manner (P < 0.05, P < 0.01, P < 0.001).
CONCLUSIONS:
These results suggest that Obtusifolin has antioxidant properties and improves chemically induced diabetes and its complications by modulation of oxidative stress.

J Pharmacol Sci. 2009 Oct;111(2):110-6.


METHODS AND RESULTS:
In the present study, we assessed the effects of gluco-Obtusifolin, isolated from the seeds of Cassia obtusifolia L., and its aglycone, Obtusifolin, on the learning and memory impairments induced by scopolamine using the passive avoidance and the Morris water maze tasks in mice. Gluco-Obtusifolin (1, 2, and 4 mg/kg, p.o.) and Obtusifolin (0.25, 0.5, 1, and 2 mg/kg, p.o.) significantly reversed scopolamine-induced cognitive impairments in the passive avoidance test (P<0.05). Moreover, gluco-Obtusifolin (2 mg/kg, p.o.) and Obtusifolin (0.5 mg/kg, p.o.) improved escape latencies, swimming times in the target quadrant, and crossing numbers in the zone where the platform previously existed in the Morris water maze test. In the acetylcholinesterase assay, gluco-Obtusifolin and Obtusifolin were found to inhibit acetylcholinesterase activity in vitro (IC(50) = 37.2 and 18.5 microM, respectively) and ex vivo.
CONCLUSIONS:
These results suggest that gluco-Obtusifolin and its aglycone may be useful for the treatment of cognitive impairment, and that its beneficial effects are mediated, in part, by the enhancement of cholinergic signaling.

Obtusifolin Dilution Calculator

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Preparing Stock Solutions of Obtusifolin

1 mg 5 mg 10 mg 20 mg 25 mg
1 mM 3.5178 mL 17.5889 mL 35.1778 mL 70.3556 mL 87.9446 mL
5 mM 0.7036 mL 3.5178 mL 7.0356 mL 14.0711 mL 17.5889 mL
10 mM 0.3518 mL 1.7589 mL 3.5178 mL 7.0356 mL 8.7945 mL
50 mM 0.0704 mL 0.3518 mL 0.7036 mL 1.4071 mL 1.7589 mL
100 mM 0.0352 mL 0.1759 mL 0.3518 mL 0.7036 mL 0.8794 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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References on Obtusifolin

Effect of obtusifolin administration on retinal capillary cell death and the development of retinopathy in diabetic rats.[Pubmed:25030406]

Cell Biochem Biophys. 2014 Dec;70(3):1655-61.

Oxidative stress is increased in the retina in diabetes, and it is considered to play an important role in the development of retinopathy. Findings indicate that Obtusifolin has antioxidant properties. The purpose of this study was to examine the effect of Obtusifolin on retinal capillary cell apoptosis and the development of pathology in diabetes. Retina was used from streptozotocin-induced diabetic rats receiving diets supplemented with or without Obtusifolin (100, 200, and 400 mg/kg) for 11 months of diabetes. Capillary cell apoptosis (by terminal transferase-mediated dUTP nick-end labeling) and formation of acellular capillaries were investigated in the trypsin-digested retinal microvessels. The effect of Obtusifolin administration on retinal 8-hydroxy-2'deoxyguanosine (8-OHdG) and nitrotyrosine levels was determined by enzyme-linked immunosorbent assay. Obtusifolin administration for the entire duration of diabetes inhibited capillary cell apoptosis and the number of acellular capillaries in the retina, despite similar severity of hyperglycemia in the four diabetic groups (with and without Obtusifolin). Retinal 8-OHdG and nitrotyrosine levels were significantly increased, respectively, in diabetes, and Obtusifolin administration inhibited these increases. Our results demonstrate that the long-term administration of Obtusifolin has beneficial effects on the development of diabetic retinopathy via inhibition of accumulation of oxidatively modified DNA and nitrotyrosine in the retina. Obtusifolin represents an achievable adjunct therapy to help prevent vision loss in diabetic patients.

Obtusifolin treatment improves hyperlipidemia and hyperglycemia: possible mechanism involving oxidative stress.[Pubmed:25015065]

Cell Biochem Biophys. 2014 Dec;70(3):1751-7.

Clinical research has confirmed the efficacy of several plant extracts in the modulation of oxidative stress associated with hyperlipidemia and hyperglycemia induced by obesity and diabetes. Findings indicate that Obtusifolin has antioxidant properties. The aim of this study was to evaluate the possible protective effects of Obtusifolin against oxidative damage in diabetic hyperlipidemia and hyperglycemia. In this study, the rats were divided into the following groups with eight animals in each: control, untreated diabetic, three Obtusifolin (10, 30, and 90 mg/kg/day)-treated diabetic groups. Diabetes was induced by streptozotocin (STZ) in rats. STZ was injected intraperitoneally at a single dose of 60 mg/kg for diabetes induction. Obtusifolin (intraperitoneal injection) was administered 3 days after STZ administration; these injections were continued to the end of the study (4 weeks). At the end of the 4-week period, blood was drawn for biochemical assays. In order to determine the changes of cellular antioxidant defense systems, antioxidant enzymes including glutathione peroxidase (GPx), superoxide dismutase (SOD), and catalase (CAT) activities were measured in serum. Moreover, we also measured serum nitric oxide (NO) and serum malondialdehyde (MDA) levels, markers of lipid peroxidation. STZ-induced diabetes caused an elevation (P < 0.001) of blood glucose, MDA, NO, total lipids, triglycerides and cholesterol, with reduction of GSH level and CAT and SOD activities. The results indicated that the significant elevation in the blood glucose, MDA, NO, total lipids, triglycerides and cholesterol; also the reduction of glutathione level and CAT and SOD activity were ameliorated in the Obtusifolin-treated diabetic groups compared with the untreated groups, in a dose-dependent manner (P < 0.05, P < 0.01, P < 0.001). These results suggest that Obtusifolin has antioxidant properties and improves chemically induced diabetes and its complications by modulation of oxidative stress.

Gluco-obtusifolin and its aglycon, obtusifolin, attenuate scopolamine-induced memory impairment.[Pubmed:19834282]

J Pharmacol Sci. 2009 Oct;111(2):110-6.

In the present study, we assessed the effects of gluco-Obtusifolin, isolated from the seeds of Cassia obtusifolia L., and its aglycone, Obtusifolin, on the learning and memory impairments induced by scopolamine using the passive avoidance and the Morris water maze tasks in mice. Gluco-Obtusifolin (1, 2, and 4 mg/kg, p.o.) and Obtusifolin (0.25, 0.5, 1, and 2 mg/kg, p.o.) significantly reversed scopolamine-induced cognitive impairments in the passive avoidance test (P<0.05). Moreover, gluco-Obtusifolin (2 mg/kg, p.o.) and Obtusifolin (0.5 mg/kg, p.o.) improved escape latencies, swimming times in the target quadrant, and crossing numbers in the zone where the platform previously existed in the Morris water maze test. In the acetylcholinesterase assay, gluco-Obtusifolin and Obtusifolin were found to inhibit acetylcholinesterase activity in vitro (IC(50) = 37.2 and 18.5 microM, respectively) and ex vivo. These results suggest that gluco-Obtusifolin and its aglycone may be useful for the treatment of cognitive impairment, and that its beneficial effects are mediated, in part, by the enhancement of cholinergic signaling.

Obtusifolin suppresses phthalate esters-induced breast cancer bone metastasis by targeting parathyroid hormone-related protein.[Pubmed:25415928]

J Agric Food Chem. 2014 Dec 10;62(49):11933-40.

This study is the first to demonstrate that parathyroid hormone-related protein (PTHrP), produced by human breast cancer cells after exposure to phthalate esters, contributes to bone metastasis by increasing osteoclastogenesis. This is also the first to reveal that Obtusifolin reverses phthalate esters-mediated bone resorption. Human breast cancer cells were treated with dibutyl phthalate (DBP), harvested in conditioned medium, and cultured to osteoblasts or osteoclasts. Cultures of osteoblasts with DBP-MDA-MB-231-CM increased the osteoclastogenesis activator RANKL (receptor activator of nuclear factor kappa-B ligand) and M-CSF (macrophage colony-stimulating factor). PTHrP was secreted in MDA-MB-231 cells. DBP-MDA-MB-231-CM reduced osteoblasts to produce osteoprotegerin, an osteoclastogenesis inhibitor, while DBP mediated PTHrP up-regulation, increasing IL-8 secretion in MDA-MB-231 and contributing to breast cancer-mediated osteoclast differentiation and bone resorption. Obtusifolin, a major bioactive compound present in Cassia tora L., suppressed phthalate esters-mediated bone resorption. Therefore, Obtusifolin may be a novel anti-breast-cancer bone metastasis agent.

Anti-allodynic effects of obtusifolin and gluco-obtusifolin against inflammatory and neuropathic pain.[Pubmed:25070277]

Biol Pharm Bull. 2014;37(10):1606-16. Epub 2014 Jul 25.

Inflammatory pain and neuropathic pain are major health issues that represent considerable social and economic burden worldwide. In this study we investigated the potential of Obtusifolin and gluco-Obtusifolin, two anthraquinones found in the seeds of the widely used traditional Chinese medical botanical Cassia obtusifolia, to reduce neuropathic and inflammatory pain. The potential analgesic effects of Obtusifolin and gluco-Obtusifolin were evaluated by mice formalin test and complete Freund's adjuvant (CFA)-induced nociceptive behaviors in rats. Chronic constriction injury (CCI), L5 spinal nerve ligation (L5 SNL), diabetes, and chemotherapeutics inducing allodynia were used to test whether repeated treatment with Obtusifolin and gluco-Obtusifolin ameliorated neuropathic pain. Finally, we explored whether Obtusifolin and gluco-Obtusifolin altered the degree of neuroinflammation in rat spinal cord after CFA administration and CCI induction. Obtusifolin and gluco-Obtusifolin (0.25, 0.5, 1, and 2 mg/kg) reduced licking/biting time in dose-dependent manner in phase 2 of formalin-induced behavior in mice. Furthermore, repeated administration of Obtusifolin and gluco-Obtusifolin (0.25, 0.5, 1, and 2 mg/kg) reversed mechanical allodynia induced by CFA, CCI, L5 SNL, diabetes, and oxaliplatin in a dose-dependent manner in rats. Levels of activated nuclear factor-kappa B (NF-kappaB) and proinflammatory cytokines (interleukin (IL)-1beta, IL-6, tumor necrosis factor alpha (TNF-alpha)) in lumbar spinal cord were elevated in rats following CFA treatment and CCI induction, and Obtusifolin and gluco-Obtusifolin significantly inhibited these effects. Our results demonstrate that Obtusifolin and gluco-Obtusifolin produce significant antinociceptive action in rodent behavioral models of inflammatory/neuropathic pain, and that this activity is associated with modulation of neuroinflammation in spinal cord.

Description

Obtusifolin, isolated from the seeds of Cassia obtusifolia, regulates the gene expression and production of MUC5AC mucin in airway epithelial cells via inhibiting NF-kB pathway. Obtusifolin suppresses phthalate esters-induced breast cancer bone metastasis by targeting parathyroid hormone-related protein.

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