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Fraxinellone

$113

  • Brand : BIOFRON

  • Catalogue Number : BF-F1001

  • Specification : 98%

  • CAS number : 28808-62-0

  • Formula : C14H16O3

  • Molecular Weight : 232.277

  • PUBCHEM ID : 124039

  • Volume : 20mg

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Catalogue Number

BF-F1001

Analysis Method

HPLC,NMR,MS

Specification

98%

Storage

2-8°C

Molecular Weight

232.277

Appearance

White crystalline powder

Botanical Source

Melia azedarach,Dictamnus dasycarpus,Aster indicus,Tephroseris phaeantha

Structure Type

Terpenoids

Category

Standards;Natural Pytochemical;API

SMILES

CC1=C2C(=O)OC(C2(CCC1)C)C3=COC=C3

Synonyms

(3R,3aR)-3-(furan-3-yl)-3a,7-dimethyl-3a,4,5,6-tetrahydro-2-benzofuran-1(3H)-one/(3R,3aR)-3-(3-Furyl)-3a,7-dimethyl-3a,4,5,6-tetrahydro-2-benzofuran-1(3H)-one/1(3H)-Isobenzofuranone, 3-(3-furanyl)-3a,4,5,6-tetrahydro-3a,7-dimethyl-, (3R,3aR)-

IUPAC Name

(3R,3aR)-3-(furan-3-yl)-3a,7-dimethyl-3,4,5,6-tetrahydro-2-benzofuran-1-one

Density

1.2±0.1 g/cm3

Solubility

Methanol; Ethyl Acetate; Acetontrile; DMSO

Flash Point

179.3±24.6 °C

Boiling Point

372.9±30.0 °C at 760 mmHg

Melting Point

116ºC

InChl

InChI=1S/C14H16O3/c1-9-4-3-6-14(2)11(9)13(15)17-12(14)10-5-7-16-8-10/h5,7-8,12H,3-4,6H2,1-2H3/t12-,14+/m0/s1

InChl Key

XYYAFLHHHZVPRN-GXTWGEPZSA-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#:28808-62-0) MSDS, density, melting point, boiling point, structure, formula, molecular weight etc. Articles of coniferyl ferulate are included as well.>> amp version: coniferyl ferulate

PMID

30716587

Abstract

Inflammasomes promote the production of pro-inflammatory cytokines, such as interleukin (IL)-1β and IL-18, which are the representative mediators of inflammation. Abnormal activation of inflammasomes leads to the development of inflammatory diseases such as acute pancreatitis (AP). In this study, we demonstrate the inhibitory effects of a new natural compound fraxinellone on inflammasome formation and examine the role of inflammasomes in a mouse model of AP. AP was induced with hourly intraperitoneal injections of supramaximal concentrations of the stable cholecystokinin analogue cerulein (50 μg/kg) for 6 h. Mice were sacrificed 6 h after the final cerulein injection. Blood and pancreas samples were obtained for further experiments. Intraperitoneal injection of fraxinellone significantly inhibited the pancreatic activation of multiple inflammasome molecules such as NACHT, LRR and PYD domains-containing protein 3 (NLRP3), PY-CARD, caspase-1, IL-18, and IL-1β during AP. In addition, fraxinellone treatment inhibited pancreatic injury, elevation in serum amylase and lipase activities, and infiltration of inflammatory cells such as neutrophils and macrophages but had no effect on pancreatic edema. To investigate whether inflammasome activation leads to the infiltration of inflammatory cells, we used parthenolide, a well-known natural inhibitor, and IL-1 receptor antagonist mice. The inhibition of inflammasome activation by pharmacological/or genetic modification restricted the infiltration of inflammatory cells, but not edema, consistent with the results observed with fraxinellone. Taken together, our study highlights fraxinellone as a natural inhibitor of inflammasomes and that inflammasome inhibition may lead to the suppression of inflammatory cells during AP.

Copyright © 2019 Elsevier B.V. All rights reserved.

KEYWORDS

Acute pancreatitis; Fraxinellone; Inflammasome; Interleukin-1; Macrophage; Neutrophil

Title

Fraxinellone inhibits inflammatory cell infiltration during acute pancreatitis by suppressing inflammasome activation.

Author

Kim MJ1, Bae GS2, Jo IJ3, Choi SB2, Kim DG4, Jung HJ5, Song HJ1, Park SJ6.

Publish date

2019 Apr;

PMID

30528694

Abstract

To improve the insecticidal activities of fraxinellone, two series of fraxinellone-based N-(1,3-thiazol-2-yl)carboxamides containing 25 compounds were prepared by structural modification. Their structures were determined by melting point, optical rotation, IR, 1H NMR and ESI-MS. The steric configurations of compounds 6i, 7d and 7i were unambiguously confirmed by X-ray diffraction further. The bioassay showed that compounds 6b and 6i exhibited more potent larvicidal and growth inhibitory activities against Plutella xylostella Linnaeus and Mythimna separata Walker, respectively. Moreover, compounds 6b and 6i also displayed low cytotoxicity to noncancerous mammalian cells. The structure-activity relationships (SARs) of all target compounds were also observed.

Copyright © 2018 Elsevier Ltd. All rights reserved.

KEYWORDS

1,3-Thiazole; Cytotoxic activity; Fraxinellone; Insecticidal activity; Structural modification; Structure-activity relationship

Title

Turning natural products into insecticide candidates: Design and semisynthesis of novel fraxinellone-based N-(1,3-thiazol-2-yl)carboxamides against two crop-threatening insect pests.

Author

Guo Y1, Fan J2, Zhang Q2, Bao C2, Liu Z2, Yang R3.

Publish date

2019 Jan 15

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


Description :

Suppression of NF-κB signaling and NLRP3 inflammasome activation in macrophages is responsible for the amelioration of experimental murine colitis by the natural compound fraxinellone. PUMID/DOI:25448682 Toxicol Appl Pharmacol. 2014 Oct 13;281(1):146-156. Inflammatory bowel disease (IBD) affects millions of people worldwide. Although the etiology of this disease is uncertain, accumulating evidence indicates a key role for the activated mucosal immune system. In the present study, we examined the effects of the natural compound Fraxinellone on dextran sulfate sodium (DSS)-induced colitis in mice, an animal model that mimics IBD. Treatment with Fraxinellone significantly reduced weight loss and diarrhea in mice and alleviated the macroscopic and microscopic signs of the disease. In addition, the activities of myeloperoxidase and alkaline phosphatase were markedly suppressed, while the levels of glutathione were increased in colitis tissues following Fraxinellone treatment. This compound also decreased the colonic levels of interleukin (IL)-1β, IL-6, IL-18 and tumor necrosis factor (TNF)-α in a concentration-dependent manner. These effects of Fraxinellone in mice with experimental colitis were attributed to its inhibition of CD11b+ macrophage infiltration. The mRNA levels of macrophage-related molecules in the colon, including intercellular adhesion molecule 1 (ICAM1), vascular cell adhesion molecule 1 (VCAM1), inducible nitric oxide synthase (iNOS) and cyclooxygenase-2 (COX2), were also markedly inhibited following Fraxinellone treatment. The results from in vitro assays showed that Fraxinellone significantly reduced lipopolysaccharide (LPS)-induced production of nitric oxide (NO), IL-1β and IL-18 as well as the activity of iNOS in both THP-1 cells and mouse primary peritoneal macrophages. The mechanisms responsible for these effects were attributed to the inhibitory role of Fraxinellone in NF-κB signaling and NLRP3 inflammasome activation. Overall, our results support Fraxinellone as a novel drug candidate in the treatment of colonic inflammation. Fraxinellone inhibits lipopolysaccharide-induced inducible nitric oxide synthase and cyclooxygenase-2 expression by negatively regulating nuclear factor-kappa B in RAW 264.7 macrophages cells. PUMID/DOI:19483316 Biol Pharm Bull. 2009 Jun;32(6):1062-8. Fraxinellone is formed by the natural degradation of limonoids isolated from the root bark of Dictamnus dasycarpus. Fraxinellone has been reported to possess neuroprotective and vasorelaxing activities, but the effects and the mechanism of Fraxinellone in inflammation have not been fully characterized. In the present study, the anti-inflammatory effect of Fraxinellone was evaluated in lipopolysaccharide (LPS)-treated RAW 264.7 macrophages. Fraxinellone was found to inhibit LPS-induced nitric oxide (NO) and prostaglandin E(2) (PGE(2)) production, and to reduce the LPS-induced expressions of inducible nitric oxide synthase (iNOS) and cyclooxygenase-2 (COX-2) at the mRNA and protein levels in a dose-dependent manner. Furthermore, Fraxinellone significantly attenuated LPS-induced DNA binding activity and the transcription activity of nuclear factor-kappa B (NF-kappaB). Consistent with these findings, pretreatment with Fraxinellone significantly suppressed the LPS-stimulated phosphorylation of inhibitory kappa B-alpha (IkappaB-alpha) and the subsequent translocation of p65 to the nucleus. Fraxinellone also suppressed the IkappaB kinase (IKK) activity and the phosphorylation of extracellular-signal-related kinase (ERK1/2), whereas the phosphorylations of Jun N-terminal kinase (JNK1/2) and p38 were unaffected. These results suggest that the anti-inflammatory properties of Fraxinellone are related to the down-regulations of iNOS and COX-2 due to NF-kappaB inhibition through the negative regulations of IKK and ERK1/2 phosphorylations in RAW 264.7 cells. Selective triggering of apoptosis of concanavalin A-activated T cells by fraxinellone for the treatment of T-cell-dependent hepatitis in mice. PUMID/DOI:19428326 Biochem Pharmacol. 2009 Jun 1;77(11):1717-24. In the present study, we found that Fraxinellone, a small natural compound isolated from the root bark of Dictamnus dasycarpus, selectively facilitated apoptosis of concanavalin A (Con A)-activated CD4(+) T cells rather than those non-activated, by disrupting the mitochondrial transmembrane potential, decreasing the ratio of Bcl-2/Bax, and increasing cytochrome c release from the mitochondria to the cytosol. The enhancement in Fas expression and caspase-8 activity, truncation of Bid, and down-regulation of anti-apoptotic cellular FLICE-inhibitory protein expression by Fraxinellone also suggested the participation of an extrinsic apoptosis pathway. Furthermore, Fraxinellone significantly alleviated Con A-induced T-cell-dependent hepatitis in mice, which was closely associated with reduced serum transaminases, pro-inflammatory cytokines, and pathologic parameters. Consistent with the in vitro results, Fraxinellone dramatically induced apoptosis of activated peripheral CD4(+) T cells in vivo, consequently resulting in less CD4(+) T-cell activation and infiltration to the liver. These results strongly suggest Fraxinellone might be a potential leading compound useful in treating T-cell-mediated liver disorders in humans. Insecticidal and feeding deterrent effects of fraxinellone from Dictamnus dasycarpus against four major pests. PUMID/DOI:23455666 Molecules. 2013 Mar 1;18(3):2754-62. Fraxinellone, a well-known and significant naturally occurring compound isolated from Meliaceae and Rutaceae spp. has been widely used as a drug for the treatment of tumors. On the other hand, Fraxinellone exhibited a variety of insecticidal activities including feeding-deterrent activity, inhibition of growth, and larvicidal activity. The present study focused on the antifeedant and larvicidal activities of Fraxinellone against the larvae of Lepidoptera, including Mythimna separata, Agrotis ypsilon, Plutella xylostella, and one kind of sanitary pest, Culux pipiens pallens. Meanwhile, the ovicidal activities and the effects of Fraxinellone on the larval development of M. separata were also observed. The LC50 values of Fraxinellone against 3rd instar larvae of M. separata, 2nd instar larvae of P. xylostella and 4th instar larvae of C. pipiens pallens were 15.95/6.43/3.60 × 10-2 mg mL-1, and its AFC50 values against 5th instar larvae of M. separata, 2nd instar larvae of P. xylostella and 2nd instar larvae of A. ypsilon were 10.73/7.93/12.58 mg mL-1, respectively. Compared with the control group, Fraxinellone obviously inhibited the pupation rate and the growth of M. separata. Once M. separata was treated with Fraxinellone at concentrations of 5.0, 10.0, and 20.0 mg mL-1, respectively, the stages from the larvae to adulthood and the egg hatching duration were prolonged to 1/2/3, and 4/3/4 days, respectively. Additionally, Fraxinellone strongly inhibited the development rate and the egg hatch proportion of M. separata. Vasorelaxing effect in rat thoracic aorta caused by fraxinellone and dictamine isolated from the Chinese herb Dictamnus dasycarpus Turcz: comparison with cromakalim and Ca2+ channel blockers. PUMID/DOI:1377790 Naunyn Schmiedebergs Arch Pharmacol. 1992 Mar;345(3):349-55. The components of Dictamnus dasycarpus Turcz were tested for their vasorelaxing effect on the rat aorta, and Fraxinellone and dictamine were shown to be effective vasorelaxants. In high K+ (60 mmol/l) medium, Ca2+ (0.03 to 3 mmol/l)-induced vasoconstriction was inhibited concentration-dependen