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Obtusifolin

$143

  • Brand : BIOFRON

  • Catalogue Number : BF-O1002

  • Specification : 98%

  • CAS number : 477-85-0

  • Formula : C16H12O5

  • Molecular Weight : 284.27

  • PUBCHEM ID : 3083575

  • Volume : 20mg

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Catalogue Number

BF-O1002

Analysis Method

HPLC,NMR,MS

Specification

98%

Storage

2-8°C

Molecular Weight

284.27

Appearance

Orange crystalline powder

Botanical Source

Senna tora,Hemerocallis citrina

Structure Type

Alkaloids

Category

Standards;Natural Pytochemical;API

SMILES

CC1=CC2=C(C(=C1O)OC)C(=O)C3=C(C2=O)C=CC=C3O

Synonyms

Anthraquinone,2,8-dihydroxy-1-methoxy-3-methyl/2,8-dihydroxy-1-methoxy-3-methyl-anthraquinone/Anthraquinone, 2,8-dihydroxy-1-methoxy-3-methyl-/9,10-Anthracenedione, 2,8-dihydroxy-1-methoxy-3-methyl-/2,8-Dihydroxy-1-methoxy-3-methyl-anthrachinon/obtusifoline/Obtusifolin (anthraquinone)/1,7-Dihydroxy-8-methoxy-6-methyl-9,10-anthraquinone/2,8-Dihydroxy-1-methoxy-3-methyl-9,10-anthraquinone/Obtusifolin/2,8-dihydroxy-1-methoxy-3-methylanhraquinone/2,8-Dihydroxy-1-methoxy-3-methyl-9,10-anthracenedione

IUPAC Name

2,8-dihydroxy-1-methoxy-3-methylanthracene-9,10-dione

Density

1.448±0.06 g/cm3

Solubility

Tetrahydrofuran

Flash Point

202.2±23.6 °C

Boiling Point

528.0±50.0 °C at 760 mmHg

Melting Point

242-243ºC

InChl

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

InChl Key

NYRXUBDGDSRBGB-UHFFFAOYSA-N

WGK Germany

RID/ADR

HS Code Reference

2914690000

Personal Projective Equipment

Correct Usage

For Reference Standard and R&D, Not for Human Use Directly.

Meta Tag

provides coniferyl ferulate(CAS#:477-85-0) MSDS, density, melting point, boiling point, structure, formula, molecular weight etc. Articles of coniferyl ferulate are included as well.>> amp version: coniferyl ferulate

PMID

30015829

Abstract

DM is often accompanied by macrovascular complications. Obtusifolin, which is an anthraquinone‑based compound with antioxidant activity, is obtained from the seeds of Cassia obtusifolia. In this study, the potential effect of obtusifolin was investigated in human umbilical vein endothelial cells. The results from flow cytometry analysis revealed that pretreatment with obtusifolin depressed the production of cellular reactive oxygen species that was induced by high glucose content. Moreover, the results showed that pretreatment with obtusifolin reduced the level of malondialdehyde, as well as recovered the activities of mitochondrial complex I/III, catalase and superoxide dismutase. Furthermore, flow cytometry analysis also revealed that mitochondrial membrane potential and cell apoptosis were recovered, and inhibited by obtusifolin, respectively. The expression of X chromosome‑linked IAP was upregulated, whereas the expressions of poly ADP‑ribose polymerase and cysteinyl aspartate specific proteinase‑3/9 were downregulated by the pretreatment with obtusifolin. Notably, the western blot analyses showed that the release of Omi/HtrA2 into the cytosol was prevented by the pretreatment with obtusifolin. Conclusively, it was suggested that obtusifolin may provide protection against mitochondrial apoptosis largely through inhibition of the release of Omi/HtrA2 from mitochondria into cytosol.

Title

Obtusifolin Inhibits High Glucose‑induced Mitochondrial Apoptosis in Human Umbilical Vein Endothelial Cells

Author

Obtusifolin Inhibits High Glucose‑induced Mitochondrial Apoptosis in Human Umbilical Vein Endothelial Cells

Publish date

2018 Sep

PMID

25015065

Abstract

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.

Title

Obtusifolin Treatment Improves Hyperlipidemia and Hyperglycemia: Possible Mechanism Involving Oxidative Stress

Author

Yu Tang, Zhiying Zhong

Publish date

2014 Dec

PMID

25415928

Abstract

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 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. Therefore, obtusifolin may be a novel anti-breast-cancer bone metastasis agent.

KEYWORDS

Cassia tora; PTHrP; obtusifolin; osteoclastogenesis; phthalate.

Title

Obtusifolin Suppresses Phthalate Esters-Induced Breast Cancer Bone Metastasis by Targeting Parathyroid Hormone-Related Protein

Author

Ya-Ling Hsu 1 , Eing-Mei Tsai, Ming-Feng Hou, Tsu-Nai Wang, Jen-Yu Hung, Po-Lin Kuo

Publish date

2014 Dec 10


Description :

Anti-allodynic effects of obtusifolin and gluco-obtusifolin against inflammatory and neuropathic pain. PUMID/DOI: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. 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. 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. Effect of obtusifolin administration on retinal capillary cell death and the development of retinopathy in diabetic rats. PUMID/DOI:DOI: 10.1007/s12013-014-0109-z 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. PUMID/DOI:DOI: 10.1007/s12013-014-0124-0 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. Obtusifolin suppresses phthalate esters-induced breast cancer bone metastasis by targeting parathyroid hormone-related protein. PUMID/DOI:DOI: 10.1021/jf5042905 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 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. Therefore, obtusifolin may be a novel anti-breast-cancer bone metastasis agent. Gluco-obtusifolin and its aglycon, obtusifolin, attenuate scopolamine-induced memory impairment. PUMID/DOI: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. Anthraquinones from the seeds of Cassia tora with inhibitory activity on protein glycation and aldose reductase. PUMID/DOI:17978503 Biol Pharm Bull. 2007 Nov;30(11):2207-10. Nine anthraquinones, aurantio-obtusin (1), chryso-obtusin (2), obtusin (3), chryso-obtusin-2-O-beta-D-glucoside (4), physcion (5), emodin (6), chrysophanol (7), obtusifolin (8), and obtusifolin-2-O-beta-D-glucoside (9), isolated from an EtOAc-soluble extract of the seeds of Cassia tora, were subjected to in vitro bioassays to evaluate their inhibitory activity against advanced glycation end products (AGEs) formation and rat lens aldose reductase (RLAR). Among the isolates, compounds 6 and 8 exhibited a significant inhibitory activity on AGEs formation with observed IC(50) values of 118 and 28.9 microM, respectively, in an AGEs-bovine serum albumin (BSA) assay by specific fluorescence. Furthermore, compounds 6 and 8 inhibited AGEs-BSA formation more effectively than aminoguanidine, an AGEs inhibitor, by indirect AGEs-ELISA. N(epsilon)-Carboxymethyllysine (CML)-BSA formation was also inhibited by compounds 6 and 8. Whereas compounds 1, 4, and 6 showed a significant inhibitory activity on RLAR with IC(50) values of 13.6, 8.8, and 15.9 microM, respectively.