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Taraxasterol

$320

  • Brand : BIOFRON

  • Catalogue Number : BD-D0057

  • Specification : HPLC≥98%

  • CAS number : 1059-14-9

  • Formula : C30H50O

  • Molecular Weight : 426.72

  • PUBCHEM ID : 115250

  • Volume : 10mg

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Catalogue Number

BD-D0057

Analysis Method

HPLC,NMR,MS

Specification

HPLC≥98%

Storage

2-8°C

Molecular Weight

426.72

Appearance

White crystalline powder

Botanical Source

Taraxacum mongolicum Hand.-Mazz.

Structure Type

Triterpenoids

Category

Standards;Natural Pytochemical;API

SMILES

CC1C2C3CCC4C5(CCC(C(C5CCC4(C3(CCC2(CCC1=C)C)C)C)(C)C)O)C

Synonyms

anthesterin/Urs-20(30)-en-3-ol, (5ξ,19ξ)-/(3β,18α,19α)-Urs-20(30)-en-3-ol/(5ξ,19ξ)-Urs-20(30)-en-3-ol/(3b,18a,19a)-Urs-20(30)-en-3-ol/a-Lactucerol/Taraxasterin/Urs-20(30)-en-3-ol, (3β,18α,19α)-/18a,19a-Urs-20(30)-en-3b-ol/18α,19βH-Urs-20(30)-en-3β-ol/Taraxasterol/Taraxast-20(30)-en-3b-ol

IUPAC Name

(3S,4aR,6aR,6aR,6bR,8aR,12S,12aR,14aR,14bR)-4,4,6a,6b,8a,12,14b-heptamethyl-11-methylidene-1,2,3,4a,5,6,6a,7,8,9,10,12,12a,13,14,14a-hexadecahydropicen-3-ol

Applications

Taraxasterol is a pentacyclic triterpenoid isolated from Taraxacum officinale. Taraxasterol has a role as a metabolite and an anti-inflammatory agent[1].

Density

1.0±0.1 g/cm3

Solubility

Soluble in Chloroform,Dichloromethane,Ethyl Acetate,DMSO,Acetone,etc.

Flash Point

217.0±12.4 °C

Boiling Point

488.2±14.0 °C at 760 mmHg

Melting Point

221-222°

InChl

InChI=1S/C30H50O/c1-19-11-14-27(5)17-18-29(7)21(25(27)20(19)2)9-10-23-28(6)15-13-24(31)26(3,4)22(28)12-16-30(23,29)8/h20-25,31H,1,9-18H2,2-8H3/t20-,21-,22+,23-,24+,25+,27-,28+,29-,30-/m1/s1

InChl Key

XWMMEBCFHUKHEX-CWFQSGEHSA-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#:1059-14-9) MSDS, density, melting point, boiling point, structure, formula, molecular weight etc. Articles of coniferyl ferulate are included as well.>> amp version: coniferyl ferulate

No Technical Documents Available For This Product.

PMID

31571510

Abstract

Immune hepatic injury is a liver disease closely related to an immune imbalance of T cells and macrophages. Our previous series of studies have demonstrated that taraxasterol isolated from Taraxacum possesses great anti-inflammatory and immunomodulatory effects in vivo and in vitro. In this study, we explored the preventive effects of taraxasterol and its underlying mechanisms on concanavalin A (Con A)-induced acute hepatic injury in mice. It was found that treatment with taraxasterol significantly decreased the Con A-induced increase of liver index, serum alanine aminotransferase (ALT) and aspartate aminotransferase (AST) and hepatic malondialdehyde (MDA) levels, and increased the Con A-induced decrease of hepatic glutathione (GSH) and superoxide dismutase (SOD) production. Taraxasterol also significantly inhibited the release of pro-inflammatory cytokines tumour necrosis factor-α (TNF-α), interleukin-6 (IL-6), IL-1β, interferon-γ (IFN-γ) and IL-4. In addition, treatment with taraxasterol alleviated the hepatic histopathological injury and apoptosis induced by Con A. Furthermore, taraxasterol dramatically down-regulated the expressions of T toll-like receptor (TLR2), TLR4 and nuclear factor-κappaB (NF-κB) p65, and decreased the expression ratio of Bax/Bc1-2 in hepatic tissues. These findings suggest that taraxasterol prevents Con A-induced acute hepatic injury in mice by inhibiting TLRs/NF-κB inflammatory signalling pathway and promoting Bax/Bc1-2 anti-apoptotic signalling pathway.

KEYWORDS

Bax/Bc1-2; Con A; NF-κB; Taraxasterol; hepatic injury

Title

Taraxasterol from Taraxacum prevents concanavalin A-induced acute hepatic injury in mice via modulating TLRs/NF-κB and Bax/Bc1-2 signalling pathways.

Author

Sang R1, Yu Y1, Ge B1, Xu L1, Wang Z1, Zhang X1.

Publish date

2019 Dec

PMID

31020326

Abstract

Triterpenes, consisting of six isoprene units, are one of the largest classes of natural compounds in plants. The genus Taraxacum is in the family Asteraceae and is widely distributed in the Northern Hemisphere. Various triterpenes, especially taraxerol and taraxasterol, are present in Taraxacum plants. Triterpene biosynthesis occurs through the action of oxidosqualene cyclase (OSC), which generates various types of triterpenes from 2,3-oxidosqualene after the rearrangement of the triterpene skeleton. However, no functional characterization of the OSC genes involved in triterpene biosynthesis, except for a lupeol synthase in Taraxacum officinale, has been performed. Taraxacum coreanum, or Korean dandelion, grows in Korea and China. Putative OSC genes in T. coreanum plants were isolated by transcriptome analysis, and four of these (TcOSC1, TcOSC2, TcOSC3 and TcOSC4) were functionally characterized by heterologous expression in yeast. Both TcOSC1 and TcOSC2 were closely related to dammarenediol-II synthases. TcOSC3 and TcOSC4 were strongly grouped with β-amyrin synthases. Functional analysis revealed that TcOSC1 produced several triterpenes, including taraxasterol; Ψ-taraxasterol; α-, β- and δ-amyrin; and dammarenediol-II. TcOSC2 catalyzed the production of bauerenol and another unknown triterpene, TcOSC3 catalyzed the production of β-amyrin. TcOSC4 catalyzed the production of taraxerol. Moreover, we identified taraxasterol, ψ-taraxasterol, taraxerol, lupeol, δ-amyrin, α-amyrin, β-amyrin and bauerenol in the roots and leaves of T. coreanum. Our results suggest that TcOSC1, TcOSC2, TcOSC3 and TcOSC4 are key triterpene biosynthetic enzymes in T. coreanum. These enzymes are novel triterpene synthases involved in the production of taraxasterol, bauerenol and taraxerol.

� The Author(s) 2019. Published by Oxford University Press on behalf of Japanese Society of Plant Physiologists. All rights reserved. For permissions, please email: journals.permissions@oup.com.

KEYWORDS

Dandelion; Oxidosqualene cyclase; Triterpene biosynthesis; Triterpene synthase

Title

Cloning and Characterization of Oxidosqualene Cyclases Involved in Taraxasterol, Taraxerol and Bauerenol Triterpene Biosynthesis in Taraxacum coreanum.

Author

Han JY1, Jo HJ1, Kwon EK1, Choi YE1.

Publish date

2019 Jul 1

PMID

30927736

Abstract

BACKGROUND AND AIM:
Taraxasterol, a pentacyclic-triterpene, has been reported to exert potent anti-inflammatory activity. However, the molecular mechanisms by which taraxasterol attenuates acute experimental colitis (AEC) remain undocumented.

METHODS:
A network pharmacology approach was used to identify the candidate and collective targets of taraxasterol and acute colitis, and an AEC model was established by oral administration of dextran sulfate sodium (DSS) in mice. Body weight and colon lengths were then examined, the pathological scoring was assessed by using hematoxylin and eosin staining, and the expression levels of target genes were further confirmed by qRT-PCR and immunohistochemistry (IHC) analysis in taraxasterol treated AEC models.

RESULTS:
14 collective targets of taraxasterol and acute colitis were identified by a network pharmacology analysis, including PPARG, JAK2, MMP3, NR1I2 and PTPN11. Further investigations in an AEC model showed that, taraxasterol alleviated the unfavorable clinical symptoms and attenuated the intestinal inflammation response by reducing the cytokines TNF-α, IL-1β and IL-6 levels. qRT-PCR and IHC analysis evidenced that, taraxasterol decreased MMP3 expression levels, but increased PPARG expression levels in AEC models as compared with the DSS group.

CONCLUSIONS:
Our findings demonstrated that taraxasterol improved DSS-induced AEC through regulating MMP3 and PPARG expression, providing a new insight into the potential therapeutic strategies for acute colitis.

Copyright © 2019 Elsevier B.V. All rights reserved

KEYWORDS

Acute experimental colitis; MMP3; Network pharmacology; PPARG; Taraxasterol

Title

Network pharmacology-based identification of the protective mechanisms of taraxasterol in experimental colitis.

Author

Chen W1, Da W1, Li C2, Fan H1, Liang R1, Yuan J3, Huang X4, Yang R4, Zhang J5, Zhu J6.

Publish date

2019 Jun