Catalogue Number
BF-R4003
Analysis Method
HPLC,NMR,MS
Specification
98%(HPLC)
Storage
2-8°C
Molecular Weight
270.28
Appearance
White crystalline powder
Botanical Source
Dracaena cochinchinensis,Astragalus membranaceus,Glycyrrhiza uralensis,Glycyrrhiza inflata
Structure Type
Flavonoids
Category
Standards;Natural Pytochemical;API
SMILES
COC1=C(C=CC(=C1)O)C=CC(=O)C2=CC=C(C=C2)O
Synonyms
Echinatin/Retrochalcone/(2E)-3-(4-Hydroxy-2-methoxyphenyl)-1-(4-hydroxyphenyl)-2-propen-1-one/Echinantin/2-Propen-1-one, 3-(4-hydroxy-2-methoxyphenyl)-1-(4-hydroxyphenyl)-, (2E)-/2-methoxy-4,4'-dihydroxychalcone/(2E)-3-(4-hydroxy-2-methoxyphenyl)-1-(4-hydroxyphenyl)prop-2-en-1-one/loureirin C/(E)-4,4'-Dihydroxy-2-methoxychalcone/4',4-dihydroxy-2-methoxychalcone
IUPAC Name
(E)-3-(4-hydroxy-2-methoxyphenyl)-1-(4-hydroxyphenyl)prop-2-en-1-one
Density
1.3±0.1 g/cm3
Solubility
Methanol; DMF
Flash Point
193.3±23.6 °C
Boiling Point
509.8±50.0 °C at 760 mmHg
Melting Point
210ºC (dec.)
InChl
InChI=1S/C16H14O4/c1-20-16-10-14(18)8-4-12(16)5-9-15(19)11-2-6-13(17)7-3-11/h2-10,17-18H,1H3/b9-5+
InChl Key
QJKMIJNRNRLQSS-WEVVVXLNSA-N
WGK Germany
RID/ADR
HS Code Reference
2914500000
Personal Projective Equipment
Correct Usage
For Reference Standard and R&D, Not for Human Use Directly.
Meta Tag
provides coniferyl ferulate(CAS#:34221-41-5) MSDS, density, melting point, boiling point, structure, formula, molecular weight etc. Articles of coniferyl ferulate are included as well.>> amp version: coniferyl ferulate
31717502
Esophageal squamous cell carcinoma (ESCC) is a poor prognostic cancer with a low five-year survival rate. Echinatin (Ech) is a retrochalone from licorice. It has been used as a herbal medicine due to its anti-inflammatory and anti-oxidative effects. However, its anticancer activity or underlying mechanism has not been elucidated yet. Thus, the objective of this study was to investigate the anti-tumor activity of Ech on ESCC by inducing ROS and ER stress dependent apoptosis. Ech inhibited ESCC cell growth in anchorage-dependent and independent analysis. Treatment with Ech induced G2/M phase of cell cycle and apoptosis of ESCC cells. It also regulated their related protein markers including p21, p27, cyclin B1, and cdc2. Ech also led to phosphorylation of JNK and p38. Regarding ROS and ER stress formation associated with apoptosis, we found that Ech increased ROS production, whereas its increase was diminished by NAC treatment. In addition, ER stress proteins were induced by treatment with Ech. Moreover, Ech enhanced MMP dysfunction and caspases activity. Furthermore, it regulated related biomarkers. Taken together, our results suggest that Ech can induce apoptosis in human ESCC cells via ROS/ER stress generation and p38 MAPK/JNK activation.
Echinatin; Esophageal squamous cell carcinoma; Reactive oxygen species; c-Jun N-terminal kinase; p38.
Retrochalcone Echinatin Triggers Apoptosis of Esophageal Squamous Cell Carcinoma via ROS- And ER Stress-Mediated Signaling Pathways
Ah-Won Kwak 1 , Joon-Seok Choi 2 , Mee-Hyun Lee 3 4 , Ha-Na Oh 1 , Seung-Sik Cho 1 , Goo Yoon 1 , Kangdong Liu 3 4 , Jung-Il Chae 5 , Jung-Hyun Shim 1 3
2019 Nov 9
21133889
Background and purpose: Flavonoids, important plant pigments, have been shown to allosterically modulate brain GABA(A) receptors (GABA(A)Rs). We previously reported that trans-6,4′-dimethoxyretrochalcone (Rc-OMe), a hydrolytic derivative of the corresponding flavylium salt, displayed nanomolar affinity for the benzodiazepine binding site of GABA(A)Rs. Here, we evaluate the functional modulations of Rc-OMe, along with two other synthetic derivatives trans-6-bromo-4′-methoxyretrochalcone (Rc-Br) and 4,3′-dimethoxychalcone (Ch-OMe) on GABA(A)Rs.
Experimental approach: Whole-cell patch-clamp recordings were made to determine the effects of these derivatives on GABA(A)Rs expressed in HEK-293 cells and in hippocampal CA1 pyramidal and thalamic neurones from rat brain.
Key results: Rc-OMe strongly potentiated GABA-evoked currents at recombinant α(1-4)β(2)γ(2s) and α(4)β(3)δ receptors but much less at α(1)β(2) and α(4)β(3). Rc-Br and Ch-OMe potentiated GABA-evoked currents at α(1)β(2)γ(2s). The potentiation by Rc-OMe was only reduced at α(1)H101Rβ(2)γ(2s) and α(1)β(2)N265Sγ(2s), mutations known to abolish the potentiation by diazepam and loreclezole respectively. The modulation of Rc-OMe and pentobarbital as well as by Rc-OMe and the neurosteroid 3α,21-dihydroxy-5α-pregnan-20-one was supra-additive. Rc-OMe modulation exhibited no apparent voltage-dependence, but was markedly dependent on GABA concentration. In neurones, Rc-Br slowed the decay of spontaneous inhibitory postsynaptic currents and both Rc-OMe and Rc-Br positively modulated synaptic and extrasynaptic diazepam-insensitive GABA(A)Rs.
Conclusions and implications: The trans-retrochalcones are powerful positive allosteric modulators of synaptic and extrasynaptic GABA(A)Rs. These novel modulators act through an original mode, thus making them putative drug candidates in the treatment of GABA(A)-related disorders in vivo.
© 2011 The Authors. British Journal of Pharmacology © 2011 The British Pharmacological Society.
Echinatin; Esophageal squamous cell carcinoma; Reactive oxygen species; c-Jun N-terminal kinase; p38.
Retrochalcone Derivatives Are Positive Allosteric Modulators at Synaptic and Extrasynaptic GABA(A) Receptors in Vitro
Ruotian Jiang 1 , Akiko Miyamoto, Adeline Martz, Alexandre Specht, Hitoshi Ishibashi, Marie Kueny-Stotz, Stefan Chassaing, Raymond Brouillard, Lia Prado de Carvalho, Maurice Goeldner, Junichi Nabekura, Mogens Nielsen, Thomas Grutter
2011 Mar
24248440
Three O-methyltransferases which catalyze S-adenosyl-L-methionine (SAM)-dependent O-methylation of licodione (LMT), flavone/flavonol (FMT), and caffeic acid (CMT) were separated from the callus culture of Glycyrrhiza echinata, and characteristic differences between their pH optima and Mg(2+) requirement for activity were demonstrated. The activity of LMT, which is involved in retrochalcone (echinatin) biosynthesis, but not of FMT or CMT, was found to be stimulated when suspension-cultured G. echinata cells were treated with yeast extract (YE), which causes rapid production of echinatin in the cells. Cycloheximide suppressed both the YE-induced echinatin formation and LMT enhancement. The results indicate a selective induction of retrochalcone pathway in Glycyrrhiza cells in response to stress.
Regulation of Retrochalcone Biosynthesis: Activity Changes of O-methyltransferases in the Yeast Extract-Induced Glycyrrhiza Echinata Cells
S Ayabe 1 , A Udagawa, K Iida, T Yoshikawa, T Furuya
1987 Feb