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Germacrone

$78

  • Brand : BIOFRON

  • Catalogue Number : BF-G3005

  • Specification : 98%

  • CAS number : 6902-91-6

  • Formula : C15H22O

  • Molecular Weight : 218.33458

  • PUBCHEM ID : 6436348

  • Volume : 25mg

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Catalogue Number

BF-G3005

Analysis Method

HPLC,NMR,MS

Specification

98%

Storage

2-8°C

Molecular Weight

218.33458

Appearance

White needle crystal

Botanical Source

Rhododendron dauricum,Curcuma longa,Curcuma wenyujin,Curcuma phaeocaulis,Kaempferia marginata

Structure Type

Terpenoids

Category

Standards;Natural Pytochemical;API

SMILES

CC1=CCC(=C(C)C)C(=O)CC(=CCC1)C

Synonyms

(3E,7E)-10-Isopropylidene-3,7-dimethyl-3,7-cyclodecadien-1-one/3,7-Cyclodecadien-1-one, 3,7-dimethyl-10-(1-methylethylidene)-, (E,E)-/(7E)-3,7-dimethyl-10-(propan-2-ylidene)cyclodeca-3,7-dien-1-one/3,7-Cyclodecadien-1-one, 3,7-dimethyl-10-(1-methylethylidene)-, (3E,7E)-/(3E,7E)-3,7-dimethyl-10-propan-2-ylidenecyclodeca-3,7-dien-1-one/(3E,7E)-10-Isopropylidene-3,7-dimethylcyclodeca-3,7-dien-1-one/3,7-Cyclodecadien-1-one, 3,7-dimethyl-10-(1-methylethylidene)-, (3Z,7Z)-/(3E,7E)-3,7-dimethyl-10-(propan-2-ylidene)cyclodeca-3,7-dien-1-one/(3Z,7Z)-10-Isopropylidene-3,7-dimethyl-3,7-cyclodecadien-1-one/Germacrone

IUPAC Name

(3E,7E)-3,7-dimethyl-10-propan-2-ylidenecyclodeca-3,7-dien-1-one

Density

0.9±0.1 g/cm3

Solubility

Methanol; Petroleum ether; Ethyl Acetate

Flash Point

148.4±18.7 °C

Boiling Point

330.3±42.0 °C at 760 mmHg

Melting Point

55-58ºC

InChl

InChI=1S/C15H22O/c1-11(2)14-9-8-12(3)6-5-7-13(4)10-15(14)16/h7-8H,5-6,9-10H2,1-4H3/b12-8+,13-7+

InChl Key

CAULGCQHVOVVRN-SWZPTJTJSA-N

WGK Germany

RID/ADR

HS Code Reference

2914290000

Personal Projective Equipment

Correct Usage

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

Meta Tag

provides coniferyl ferulate(CAS#:6902-91-6) MSDS, density, melting point, boiling point, structure, formula, molecular weight etc. Articles of coniferyl ferulate are included as well.>> amp version: coniferyl ferulate

PMID

29655913

Abstract

Multidrug resistance (MDR) usually causes chemotherapy failure of chronic myelogenous leukemia (CML). Germacrone is a terpenoid compound and has been reported to reverse MDR in breast cancer cells. However, the effect of germacrone on MDR in CML cells was unknown. The aim of the present study was to evaluate the effect of germacrone on MDR in adriamycin resistance of CML cells. Treatment with a combination of germacrone and adriamycin synergistically inhibited the viability and increased LDH release in K562/ADM cells. Adriamycin induced the apoptosis and caspase-3 activity of K562/ADM cells, and the germacrone treatment significantly enhanced the induction. Adriamycin treatment inhibited the expression of Bcl-2 and induced the expression of Bax, and germacrone enhanced the effect of adriamycin. Germacrone decreased adriamycin-induced expression of MDR1 mRNA and P-gp protein. Overexpression of P-glycoprotein (P-gp) reversed the effect of germacrone on adriamycin resistance in K562/ADM cells. In conclusion, germacrone reversed adriamycin resistance in human chronic myelogenous leukemia K562/ADM cells by suppressing MDR1 gene/P-gp expression. The results indicated that germacrone might be a new MDR reversal agent for CML chemotherapy.

Copyright © 2018 Elsevier B.V. All rights reserved.

KEYWORDS

Adriamycin; Chronic myelogenous leukemia; Germacrone; MDR1; Multidrug resistance; P-glycoprotein

Title

Germacrone reverses adriamycin resistance in human chronic myelogenous leukemia K562/ADM cells by suppressing MDR1 gene/P-glycoprotein expression.

Author

Pan J1, Miao D2, Chen L2.

Publish date

2018 May 25

PMID

31451221

Abstract

Rheumatoid arthritis (RA) is a chronic autoimmune inflammatory disease. The imbalance of T helper type 1 (Th1) and Th2 immune responses contributes to the pathogenesis of this disease. Germacrone is a major bioactive component isolated from Rhizoma Curcuma with multiple bioactivities including anti-inflammation. However, the role and mechanism of germacrone in RA are still unknown. Collagen-induced arthritis (CIA) model was established in male DBA/1 J mice by two immunizations with chicken collagen II. Germacrone was orally administered once per day starting on the day of second immunization for 3 weeks. Arthritis scoring was evaluated every 3 days after second immunization. H&E staining was used for histopathological examination. Levels of tumor necrosis factor (TNF)-α, interferon (IFN)-γ and interleukin (IL)-4 in serum and synovial tissues of mice were detected by ELISA. Th1 and Th2 cell percentage in mouse spleens was analyzed by flow cytometry. IκB and phosphorylation of NF-κB p65 (p-p65) expression in mouse synovial tissues was assayed by Western blot. We found germacrone treatment significantly reduced arthritis score and inflammation in CIA mice. Levels of TNF-α and IFN-γ were elevated, and IL-4 reduced, in the serum and synovial tissues of CIA mice. Germacrone partially reversed levels of these cytokines. Moreover, germacrone decreased the ratio of Th1 to Th2 cells in mouse spleens. Additionally, germacrone remarkably enhanced IκB expression, but suppressed p-p65 level in CIA mice. Taken together, these results suggest that germacrone alleviated the progression of arthritis that might be related to the regulation of Th1/Th2 balance and inactivation of NF-κB pathway.

Copyright © 2019 Elsevier Inc. All rights reserved.

KEYWORDS

Germacrone; NF-κB; Rheumatoid arthritis; Th1/Th2 imbalance

Title

Germacrone alleviates collagen-induced arthritis via regulating Th1/Th2 balance and NF-κB activation.

Author

Wang Z1, Zhuo F2, Chu P2, Yang X3, Zhao G4.

Publish date

2019 Oct 20

PMID

32145743

Abstract

BACKGROUND:
Germacrone is an anti-inflammatory ingredient in the Chinese medicine zedoary turmeric. The purpose of this study was to explore the protective mechanism of germacrone against PC12 cells injury caused by oxygen-glucose deprivation/reperfusion (OGD/R).

METHODS:
OGD/R injury model of PC12 cells was established by using OGD/R (2 h/24 h). The cell viability was assessed by MTT assay and LDH release. The ultrastructure of cells was observed by transmission electron microscopy (TEM). The expression of autophagy related proteins in cells was determined by Western Blot.

RESULTS:
The results of ultrastructural observation showed that PC12 cells damaged by OGD/R showed typical autophagy characteristics. In addition, OGD/R observably up-regulated the expression of autophagy related proteins: the class III type phosphoinositide 3-kinase (PI3K III), light chain 3(LC3), and Beclin-1 in PC12 cells, and inhibited the expression of the class I type phosphoinositide 3-kinase (PI3K I), Protein kinase B (Akt), the mammalian target of rapamycin (mTOR), and B-cell lymphoma 2(Bcl-2) proteins. Furthermore, germacrone increased the cell viability of OGD/R-damaged PC12 cells by down-regulating the expression of LC3 protein in cells in a concentration-dependent manner. More importantly, germacrone significantly inhibited the expression of PI3K III, LC3, and Beclin-1 in OGD/R-injured PC12 cells, and up-regulated the expressionof PI3K I, Akt, mTOR, and Bcl-2 proteins in cells, and this inhibited or up-regulated effect was reversed by PI3K I inhibitor (ZSTK474).

CONCLUSION:
The above results indicated that germacrone could inhibit the autophagy effect in OGD/R injury model of PC12 cells, the mechanism of inhibition was regulated by PI3K III/Beclin-1/Bcl-2 and PI3K I/Akt/mTOR pathways, thereby improving the cell viability of PC12 cells and playing a neuroprotective role, which provided a new drug for the treatment of OGD/R.

KEYWORDS

Autophagy; Germacrone; Oxygen-glucose deprivation/reperfusion; PC12 cells; PI3K I/Akt/mTOR; PI3K III/Beclin-1/Bcl-2

Title

Germacrone protects against oxygen-glucose deprivation/reperfusion injury by inhibiting autophagy processes in PC12 cells.

Author

Zhang J1, Yuan L1, Wang S1, Liu J2, Bi H1, Chen G1, Li J1, Chen L3.

Publish date

2020 Mar 7


Description :

Germacrone is extracted from Rhizoma Curcuma. Germacrone inhibits influenza virus infection[1].