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β-Asarone

$250

  • Brand : BIOFRON

  • Catalogue Number : BF-A4016

  • Specification : 98%(HPLC)

  • CAS number : 5273-86-9

  • Formula : C12H16O3

  • Molecular Weight : 208.25

  • PUBCHEM ID : 5281758

  • Volume : 50mg

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Catalogue Number

BF-A4016

Analysis Method

HPLC,NMR,MS

Specification

98%(HPLC)

Storage

-20℃

Molecular Weight

208.25

Appearance

Oil

Botanical Source

Acorus gramineus

Structure Type

Phenylpropanoids

Category

Standards;Natural Pytochemical;API

SMILES

CC=CC1=CC(=C(C=C1OC)OC)OC

Synonyms

Benzene, 1,2,4-trimethoxy-5-(1-propenyl)-/1,2,4-trimethoxy-5-propenyl-benzene/cis-Isoasarone/1,2,4-trimethoxy-5-prop-1-enylbenzene/Benzene, 1,2,4-trimethoxy-5-propenyl-, trans-/(Z)-1,2,4-Trimethoxy-5-(1-propenyl)benzene/beta-asarone/1,2,4-trimethoxy-5-propenylbenzene/Benzene, 1,2,4-trimethoxy-5- (1-propenyl)-/Benzene, 1,2,4-trimethoxy-5-[(1Z)-1-propen-1-yl]-/1,2,4-Trimethoxy-5-[(1Z)-1-propen-1-yl]benzene/Benzene, 1,2,4-trimethoxy-5-propenyl-/(Z)-5-Propenyl-1,2,4-trimethoxybenzene/b-Asarone/Benzene, 1,2,4-trimethoxy-5-(1-propenyl)-, (Z)-/cis-Beta-Asarone/1,2,4-trimethoxy-5-[(1Z)-prop-1-en-1-yl]benzene/2,4,5-Trimethoxy-1-propenylbenzene/1,2,4-Trimethoxy-5-propenyl-benzol/2,4,5-trimethoxyphenylprop-1-ene/Benzene, 1,2,4-trimethoxy-5-propenyl-, (Z)-/cis-1-Propenyl-2,4,5-trimethoxybenzene/1,2,4-Trimethoxy-5-[(1Z)-1-propen-1-yl]benzene

IUPAC Name

1,2,4-trimethoxy-5-[(Z)-prop-1-enyl]benzene

Density

1.0±0.1 g/cm3

Solubility

Methanol; Chloroform

Flash Point

107.7±23.8 °C

Boiling Point

296.0±0.0 °C at 760 mmHg

Melting Point

InChl

InChI=1S/C12H16O3/c1-5-6-9-7-11(14-3)12(15-4)8-10(9)13-2/h5-8H,1-4H3/b6-5-

InChl Key

RKFAZBXYICVSKP-WAYWQWQTSA-N

WGK Germany

RID/ADR

HS Code Reference

2918990000

Personal Projective Equipment

Correct Usage

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

Meta Tag

provides coniferyl ferulate(CAS#:5273-86-9) MSDS, density, melting point, boiling point, structure, formula, molecular weight etc. Articles of coniferyl ferulate are included as well.>> amp version: coniferyl ferulate

PMID

28732807

Abstract

BACKGROUND:
Asarone is one of the most researched phytochemicals and is mainly present in the Acorus species and Guatteria gaumeri Greenman. In preclinical studies, both α- and β-asarone have been reported to have numerous pharmacological activities and at the same time, many studies have also revealed the toxicity of α- and β-asarone.

PURPOSE:
The purpose of this comprehensive review is to compile and analyze the information related to the pharmacokinetic, pharmacological, and toxicological studies reported on α- and β-asarone using preclinical in vitro and in vivo models. Besides, the molecular targets and mechanism(s) involved in the biological activities of α- and β-asarone were discussed.

METHODS:
Databases including PubMed, ScienceDirect and Google scholar were searched and the literature from the year 1960 to January 2017 was retrieved using keywords such as α-asarone, β-asarone, pharmacokinetics, toxicology, pharmacological activities (e.g. depression, anxiety).

RESULTS:
Based on the data obtained from the literature search, the pharmacokinetic studies of α- and β-asarone revealed that their oral bioavailability in rodents is poor with a short plasma half-life. Moreover, the metabolism of α- and β-asarone occurs mainly through cytochrome-P450 pathways. Besides, both α- and/or β-asarone possess a wide range of pharmacological activities such as antidepressant, antianxiety, anti-Alzheimer’s, anti-Parkinson’s, antiepileptic, anticancer, antihyperlipidemic, antithrombotic, anticholestatic and radioprotective activities through its interaction with multiple molecular targets. Importantly, the toxicological studies revealed that both α- and β-asarone can cause hepatomas and might possess mutagenicity, genotoxicity, and teratogenicity.

CONCLUSIONS:
Taken together, further preclinical studies are required to confirm the pharmacological properties of α-asarone against depression, anxiety, Parkinson’s disease, psychosis, drug dependence, pain, inflammation, cholestasis and thrombosis. Besides, the anticancer effect of β-asarone should be further studied in different types of cancers using in vivo models. Moreover, further dose-dependent in vivo studies are required to confirm the toxicity of α- and β-asarone. Overall, this extensive review provides a detailed information on the preclinical pharmacological and toxicological activities of α-and β-asarone and this could be very useful for researchers who wish to conduct further preclinical studies using α- and β-asarone.

Copyright © 2017. Published by Elsevier GmbH.

KEYWORDS

Pharmacokinetics; Pharmacology; Toxicology; α-Asarone; β -Asarone

Title

Pharmacology and toxicology of α- and β-Asarone: A review of preclinical evidence.

Author

Chellian R1, Pandy V2, Mohamed Z1.

Publish date

2017 Aug 15

PMID

29751524

Abstract

HnRNP A2/B1 has been found to be an oncogenic protein strongly related to the growth of human glioma cells. Herein, β-asarone, the main component in the volatile oil of Acori tatarinowii Rhizoma, inhibited the cell viability, proliferation, and colony formation ability of U251 cells. Moreover, β-asarone induced apoptosis and cell cycle arrest at the G1 phase. Notably, β-asarone suppressed the expression of hnRNP A2/B1 and hnRNPA2/B1 overexpression remarkably reversed β-asarone-mediated apoptosis and cell cycle arrest. Importantly, β-asarone promoted the alternative splicing of Bcl-x by enhancing the ratio of Bcl-xS/Bcl-xL. Meanwhile, hnRNPA2/B1 overexpression mitigated the promoting effect of β-asarone on the alternative splicing of Bcl-x. β-asarone also regulated the level of the key proteins involved in the death receptor pathway and mitochondrial apoptosis pathway. Additionally, β-asarone modulated the cell cycle-related proteins p21, p27, Cdc25A, cyclin D, cyclin E, and CDK2. Finally, β-asarone inhibited tumor growth and induced apoptosis in nude mice bearing U251 tumor xenografts. β-asarone also suppressed the hnRNP A2/B1 expression, enhanced the expression of cleaved-caspase 3 and p27 and the ratio of Bcl-xS/Bcl-xL, and reduced the expression of CDK2 in U251 xenografts. Together, β-asarone-induced apoptosis and cell cycle arrest of U251 cells may be related to the suppression of hnRNPA2/B1-mediated signaling pathway.

KEYWORDS

alternative splicing; apoptosis; cell cycle arrest; glioma; hnRNPA2/B1; β-asarone

Title

β-Asarone Induces Apoptosis and Cell Cycle Arrest of Human Glioma U251 Cells via Suppression of HnRNP A2/B1-Mediated Pathway In Vitro and In Vivo.

Author

Li L1, Yang Y2, Wu M3, Yu Z4, Wang C5, Dou G6, He H7, Wang H8, Yang N9, Qi H10, Xu X11.

Publish date

2018 May 3

PMID

29990876

Abstract

Lung cancer is the leading cause of cancer death worldwide. Chemotherapy is one of the most effective strategies for lung cancer treatment. However, the side effects of chemotherapy limit the application of chemotherapeutic agents. The β-Asarone, a low-toxicity natural compound from a traditional Chinese medicinal herb, has been demonstrated to display anticancer activities in multiple cancer types. However, the anticancer activities of β-Asarone in lung cancer have not been shown, and the underlying molecular mechanisms are still unclear. In the current study, we show that β-Asarone displays a dose-dependent inhibitory effect on the viability of lung cancer cells. Additionally, β-Asarone significantly suppresses the cell migration, invasion, and adhesion of lung cancer cells. Moreover, β-Asarone induces apoptosis associated with the activation of caspase-9 and caspase-3, the upregulation of XAF1, Puma, Bax (Ser184) and Bad (Ser112), the downregulation of XIAP, Bcl-2 and Survivin, the translocation of Bax, Bad, phospho-Bax (Ser184), phospho-Bad (Ser112) and cytochrome C and the reduction of the mitochondrial membrane potential. Mechanistically, our study shows that β-Asarone inhibits Wnt/β-catenin signaling. Rescuing the activation of Wnt/β-catenin signaling overcomes β-Asarone-induced anticancer effects. Taken together, our data provide the first evidence of the anticancer effects of β-Asarone in lung cancer, demonstrates that the inhibition of Wnt/β-catenin signaling could be critical for β-Asarone-induced anticancer effects. Our study thus suggests a potential application of β-Asarone as an anticancer agent in the clinical treatment of lung cancer.

Copyright © 2018 Elsevier Masson SAS. All rights reserved.

KEYWORDS

Apoptosis; Cell viability; Lung cancer; Migration/invasion/adhesion; Mitochondrial; Natural compounds; β-Asarone

Title

β-Asarone suppresses Wnt/β-catenin signaling to reduce viability, inhibit migration/invasion/adhesion and induce mitochondria-related apoptosis in lung cancer cells.

Author

Wang TL1, Ouyang CS2, Lin LZ3.

Publish date

2018 Oct


Description :

Beta-asarone is a major ingredient of Acorus tatarinowii Schott, penetrates blood brain barrier, with the properties ofimmunosuppression, central nervous system inhibition, sedation, and hypothermy. Beta-asarone protects against Parkinson’s disease[1].