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parthenolide

$113

  • Brand : BIOFRON

  • Catalogue Number : BF-P2014

  • Specification : 98%

  • CAS number : 20554-84-1

  • Formula : C15H20O3

  • Molecular Weight : 248.32

  • PUBCHEM ID : 7251185

  • Volume : 20mg

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Catalogue Number

BF-P2014

Analysis Method

HPLC,NMR,MS

Specification

98%

Storage

-20℃

Molecular Weight

248.32

Appearance

White crystalline powder

Botanical Source

Cyathocline purpurea,Magnolia grandiflora,Michelia odora

Structure Type

Terpenoids

Category

Standards;Natural Pytochemical;API

SMILES

CC1=CCCC2(C(O2)C3C(CC1)C(=C)C(=O)O3)C

Synonyms

Oxireno[9,10]cyclodeca[1,2-b]furan-9(1aH)-one, 2,3,6,7,7a,8,10a,10b-octahydro-1a,5-dimethyl-8-methylene-, (4Z)-/4,5α-Epoxy-6β-hydroxygermacra-1(10),11(13)-dien-12-oic Acid γ-Lactone/PartheNAlide/(4Z)-1a,5-Dimethyl-8-methylene-2,3,6,7,7a,8,10a,10b-octahydrooxireno[9,10]cyclodeca[1,2-b]furan-9(1aH)-one/Parthenolide/Parthelide/PARTHENOLIDE,TANACETUM PARTHENIUM

IUPAC Name

(1S,2R,4R,7E,11S)-4,8-dimethyl-12-methylidene-3,14-dioxatricyclo[9.3.0.02,4]tetradec-7-en-13-one

Density

1.1±0.1 g/cm3

Solubility

Methanol; Acetone; Ethyl Acetate

Flash Point

166.3±22.5 °C

Boiling Point

394.1±42.0 °C at 760 mmHg

Melting Point

115-116ºC(lit.)

InChl

InChl Key

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#:20554-84-1) MSDS, density, melting point, boiling point, structure, formula, molecular weight etc. Articles of coniferyl ferulate are included as well.>> amp version: coniferyl ferulate

PMID

31701984

Abstract

Parthenolide (PTL) strongly inhibits the detyrosination of microtubules and accelerates neuronal growth. In order to access cyclic ether derivatives of PTL, ring-closing metathesis (RCM) was investigated in comparison to intramolecular sulfone alkylation. Incompatibility of RCM with epoxides was found in this setting. Biological evaluation for tubulin carboxypeptidase inhibition indicated that the epoxide is crucial for parthenolide’s activity.

Title

Synthesis and biological profiling of parthenolide ether analogs.

Author

Freund RRA1, Gobrecht P2, Moser P1, Fischer D2, Arndt HD1.

Publish date

2019 Dec 7;

PMID

31553932

Abstract

A series of twenty-three parthenolide-5-fluorouracil (5-FU) conjugates ware synthesized and evaluated for their anti-cancer activities against human hepatocellular carcinoma cell line Bel-7402 and 5-fluorouracil resistant human hepatocellular carcinoma cell line Bel-7402/5-FU. The preliminary structure-activity relationships were discussed. The most active compound 15d showed high activity against Bel-7402/5-FU cell line with IC50 value of 2.25 μM, which demonstrated 5.8-fold improvement compared to that of the parent compound parthenolide (IC50 = 12.98 μM). The investigation of preliminary molecular mechanism of 15d revealed that 15d could reverse drug resistance by inhibiting MDR1, ABCC1 and ABCG2 to increase the intracellular drug accumulation and induce apoptosis of Bel-7402/5-FU cells through mitochondria mediated pathway. On the base of these results, compound 15d is deserved to be further investigated as a potential anti-HCC lead compound for ultimate discovery of pathenolide-based anti-cancer drug.

Copyright © 2019 Elsevier Masson SAS. All rights reserved.

KEYWORDS

5-Fluorouracil; Conjugation; Hepatocellular carcinoma drug resistance; Parthenolide; Structure-activity relationship

Title

Design and synthesis of parthenolide and 5-fluorouracil conjugates as potential anticancer agents against drug resistant hepatocellular carcinoma.

Author

Ding Y1, Li S1, Ge W1, Liu Z1, Zhang X1, Wang M2, Chen T1, Chen Y3, Zhang Q4.

Publish date

2019 Dec 1;

PMID

31365959

Abstract

Objective: To evaluate the effects of parthenolide on estradiol-synthesizing enzyme, steroidogenic acute regulatory protein (StAR), and ER isoforms,VEGF in human endometriotic stromal cells. Methods: Primary endometriotic stromal cells were treated with different concentrations (1, 5, 10 and 20 μmol/L) of parthenolide. The mRNA of StAR, ER isoforms (ERα and ERβ), PR, vascular endothelial growth factor (VEGF), interleukin-6 (IL-6), tumour necrosis factor-α (TNFα), tumour necrosis factor receptor (TNFR) 1, TNFR2 were measured by real-time PCR. The levels of estradiol and progesterone in the cell supernatant were measured by ELISA. Results: Different concentrations of parthenolide could up-regulate the mRNA of StAR in primary endometriotic stromal cells (F=5.722, P<0.05); the mRNA of StAR in the group of 20 μmol/L was significantly higher than that of the control group [2.6±0.3 versus 1.0, P<0.01]. Different concentrations of parthenolide could down-regulate the mRNA of ERα (F=6.921, P<0.01); the mRNA of ERα in the group of 20 μmol/L and 10 μmol/L were significantly lower than those of the control group [0.2±0.3 versus 0.3±0.3 versus 1.0, all P<0.05]. Different concentrations of parthenolide could down-regulate the ratios of ERα/ERβ mRNA levels (F=4.209, P<0.05). Different concentrations of parthenolide could up-regulate the mRNA of VEGF and TNFR1 (F=10.964, P<0.01; F=7.286, P<0.01). There were no statiscal significances with different concentrations of parthenolide on the mRNA of ERβ, PR, IL-6, TNFα and TNFR2, and the levels of estradiol and progesterone in the cell supernatant (all P>0.05). Conclusions: Parthenolide may regulate the expression of estradiol-synthesizing enzyme, ER isoforms and angiogenesis in endometriotic stromal cells. Parthenolide may promote the development of endometriosis.

KEYWORDS

Aromatase; Endometriosis; Estrogen receptor; Parthenolide; Sesquiterpenes; Stromal cells

Title

[Effects of parthenolide on estradiol-synthesizing enzyme, ER isoforms and VEGF in human endometriotic stromal cells].

Author

Song H1, Huang Y, Peng Q, Xue C, Zhou YF.

Publish date

2019 Jul 25;


Description :

Parthenolide is an NF-κB inhibitor, reduces histone deacetylase 1 (HDAC-1) and DNA methyltransferase 1 independent of NF-κB inhibition.