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Obacunone

$113

  • Brand : BIOFRON

  • Catalogue Number : BF-O1001

  • Specification : 98%

  • CAS number : 751-03-1

  • Formula : C26H30O7

  • Molecular Weight : 454.516

  • PUBCHEM ID : 119041

  • Volume : 20mg

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Catalogue Number

BF-O1001

Analysis Method

HPLC,NMR,MS

Specification

98%

Storage

2-8°C

Molecular Weight

454.516

Appearance

White crystalline powder

Botanical Source

barks of Phellodendron chinense

Structure Type

Terpenoids

Category

Standards;Natural Pytochemical;API

SMILES

CC1(C2CC(=O)C3(C(C2(C=CC(=O)O1)C)CCC4(C35C(O5)C(=O)OC4C6=COC=C6)C)C)C

Synonyms

(5aR,5bR,7aS,8S,10aS,11aR,11bR,13aR)-8-(3-Furyl)-1,1,5a,7a,11b-pentamethyl-5b,6,7,7a,8,11b,13,13a-octahydrooxireno[4,4a]isochromeno[6,5-g][2]benzoxepine-3,10,12(1H,5aH,10aH)-trione/OBACUNON/Tricoccin S3/(5aR,5bR,7aS,8R,10aS,11aR,11bR,13aR)-8-(furan-3-yl)-1,1,5a,7a,11b-pentamethyl-5b,6,7,7a,8,11b,13,13a-octahydrooxireno[4,4a]isochromeno[6,5-g][2]benzoxepine-3,10,12(1H,5aH,10aH)-trione/Obacune/Oxireno[4',5']pyrano[4',3':5,6]naphth[2,1-c]oxepin-3,10,12(1H,5aH,10aH)-trione, 8-(3-furanyl)-5b,6,7,7a,8,11b,13,13a-octahydro-1,1,5a,7a,11b-pentamethyl-, (5aR,5bR,7aS,8S,10aS,11aR,11bR,13aR)-/CasiMirolide

IUPAC Name

(1R,2R,4S,7S,8S,11R,12R,18R)-7-(furan-3-yl)-1,8,12,17,17-pentamethyl-3,6,16-trioxapentacyclo[9.9.0.02,4.02,8.012,18]icos-13-ene-5,15,20-trione

Density

1.3±0.1 g/cm3

Solubility

Acetontrile; Ethyl Acetate

Flash Point

332.5±31.5 °C

Boiling Point

626.2±55.0 °C at 760 mmHg

Melting Point

InChl

InChI=1S/C26H30O7/c1-22(2)16-12-17(27)25(5)15(23(16,3)9-7-18(28)32-22)6-10-24(4)19(14-8-11-30-13-14)31-21(29)20-26(24,25)33-20/h7-9,11,13,15-16,19-20H,6,10,12H2,1-5H3/t15-,16+,19+,20-,23-,24+,25+,26-/m1/s1

InChl Key

MAYJEFRPIKEYBL-OASIGRBWSA-N

WGK Germany

RID/ADR

HS Code Reference

2932990000

Personal Projective Equipment

Correct Usage

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

Meta Tag

provides coniferyl ferulate(CAS#:751-03-1) MSDS, density, melting point, boiling point, structure, formula, molecular weight etc. Articles of coniferyl ferulate are included as well.>> amp version: coniferyl ferulate

PMID

30274140

Abstract

Cortex Dictamni is a commonly-used traditional Chinese herbal medicine for the treatment of skin inflammation, tinea, and eczema. Recently, some studies reported that Cortex Dictamni might induce liver injury, suggesting more attention to its safety. The current study was designed to investigate subchronic toxicity of Cortex Dictamni aqueous extract (CDAE) and ethanol extract (CDEE) in mice and the potential hepatotoxicity mechanisms in vitro. Firstly, CDAE or CDEE groups were administrated with varying dosages (2.3, 4.6, or 9.2 g/kg/day, p.o.) in mice for 28 days in subchronic toxicity studies. General clinical signs and biochemical parameters were examined, and morphological analyses were conducted. Secondly, we identified the different constituents of CDAE and CDEE using HPLC-MS/MS and chose major components for further study. In order to determine the toxic components, we investigated the cytotoxicity of extracts and chosen components using CCK-8 assay in HepG2 cells. Furthermore, we explored the possible hepatotoxicity mechanisms of Cortex Dictamni using a high content analysis (HCA). The results showed that no significant differences of general clinical signs were observed in mice. Aspartate alanine aminotransferase (ALT) and aminotransferase (AST) were significantly increased in the high-dose CDAE and CDEE groups compared to the control group. Meanwhile, the absolute and relative liver weights and liver/brain ratio were significantly elevated, and histological examination of liver demonstrated cellular enlargement or nuclear shrinkage. In UPLC analysis, we compared the chemical constituents between CDAE and CDEE, and chose dictamnine, obakunone, and fraxinellone for hepatotoxicity evaluation in the in vitro studies. In the CCK-8 assay, CDAE, CDEE, dictamnine, obakunone, and fraxinellone decreased the cell viability in a dose-dependent manner after treatment for 48 h. Furthermore, the cell number decreased, while the nuclear intensity, cell membrane permeability, and concentration of reactive oxygen species were shown to increase, meanwhile, mitochondrial membrane potential was also changed in HepG2 cells following 48 h of compounds treatment using HCA. Our studies suggested that CDAE and CDEE have potential hepatotoxicity, and that the alcohol extraction process could increase toxicity. Dictamnine, obakunone, and fraxinellone may be the possible toxic components in Cortex Dictamni with dictamnine as the most potentially hepatotoxic component, whose potential hepatotoxicity mechanism may be associated with cell apoptosis. Moreover, this study could provide valuable data for clinical drug safety research of Cortex Dictamni and a good example for safety study of other Chinese herbal medicines.

KEYWORDS

Cortex Dictamni; aqueous extract; cell apoptosis; dictamnine; ethanol extract; hepatotoxicity; mechanisms

Title

Subchronic Toxicity Studies of Cortex Dictamni Extracts in Mice and Its Potential Hepatotoxicity Mechanisms in Vitro.

Author

Fan Q1, Zhao B2, Wang C3, Zhang J4, Wu J5, Wang T6, Xu A7.

Publish date

2018 Sep 28

PMID

28657665

Abstract

Obacunone (OBA) is a highly oxygenated triterpenoid with various pharmacological activities. In this study, we explored its anti-inflammatory effect and underlying mechanisms in LPS-activated macrophages. Our data showed that OBA potently decreased pro-inflammatory mediators (eg, NO, IL-6, IL-1β, and MCP-1) at the transcriptional and translational levels without cytotoxicity. A mechanism study showed that OBA significantly suppressed p38-mediated AP-1 signaling by stabilizing the mRNA of mitogen-activated protein kinase phosphatase 1 (MKP-1), thus prolonging the expression time of the MKP-1 protein. Next, we used computational target-fishing technology to predict the possible target of OBA. Only one potential target, macrophage migration inhibitory factor (MIF), was presented. Experimentally, the interaction between OBA and MIF was also confirmed. By using an anti-mouse MIF antibody, extracellular MIF (exMIF) was neutralized. Our results showed that autocrine MIF had slight influence on the pro-inflammatory mediator production. Correspondingly, the anti-inflammatory activity of OBA was also not affected. Accordingly, we knocked down the MIF gene in RAW 264.7 cells and obtained stable MIF deficient cells MIF(-), in which the effects of OBA on p38 phosphorylation, AP-1 activation, and pro-inflammatory mediator production in response to LPS nearly disappeared. In contrast to MIF(+) cells, the MKP-1 protein expression time of the MIF(-) cells was markedly prolonged. We conclude that OBA exerts its anti-inflammatory effect by targeting intracellular MIF (inMIF) inhibition to regulate the MKP-1/p38/AP-1 pathway. Our findings also provide a chain of evidence that the inhibition of inMIF, rather than exMIF, may become a novel target for inflammation.

© 2017 Wiley Periodicals, Inc.

KEYWORDS

lipopolysaccharide (LPS); macrophage migration inhibitory factor (MIF); macrophages; mitogen-activated protein kinase phosphatase 1 (MKP-1); obacunone (OBA)

Title

Obacunone causes sustained expression of MKP-1 thus inactivating p38 MAPK to suppress pro-inflammatory mediators through intracellular MIF.

Author

Gao Y1,2, Hou R1, Liu F1, Liu H1, Fei Q1, Han Y1, Cai R1, Peng C2, Qi Y1.

Publish date

2018 Jan

PMID

28594916

Abstract

TGR5, a member of the G protein-coupled receptor (GPCR) family, is activated by bile acids. Because TGR5 promotes energy expenditure and improves glucose homeostasis, it is recognized as a key target in treating metabolic diseases. We previously showed that nomilin, a citrus limonoid, activates TGR5 and confers anti-obesity and anti-hyperglycemic effects in mice. Information on the TGR5-nomilin interaction regarding molecular structure, however, has not been reported. In the present study, we found that human TGR5 (hTGR5) shows higher nomilin responsiveness than does mouse TGR5 (mTGR5). Using mouse-human chimeric TGR5, we also found that three amino acid residues (Q77ECL1, R80ECL1, and Y893.29) are important in the hTGR5-nomilin interaction. Based on these results, an hTGR5-nomilin binding model was constructed using in silico docking simulation, demonstrating that four hydrophilic hydrogen-bonding interactions occur between nomilin and hTGR5. The binding mode of hTGR5-nomilin is vastly different from those of other TGR5 agonists previously reported, suggesting that TGR5 forms various binding patterns depending on the type of agonist. Our study promotes a better understanding of the structure of TGR5, and it may be useful in developing and screening new TGR5 agonists.

Title

Identification of key amino acid residues in the hTGR5-nomilin interaction and construction of its binding model.

Author

Sasaki T1, Mita M1, Ikari N1, Kuboyama A1, Hashimoto S1, Kaneko T1, Ishiguro M2, Shimizu M1, Inoue J1, Sato R1,3,4.

Publish date

2017 Jun 8


Description :

Obacunone, isolated from seeds of Marsh White grapefruit, exhibits anti-tumor activity by the induction of apoptosis[1].