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Gramine

$43

  • Brand : BIOFRON

  • Catalogue Number : BF-G3007

  • Specification : 98%

  • CAS number : 87-52-5

  • Formula : C11H14N2

  • Molecular Weight : 174.24

  • PUBCHEM ID : 6890

  • Volume : 100mg

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Catalogue Number

BF-G3007

Analysis Method

HPLC,NMR,MS

Specification

98%

Storage

2-8°C

Molecular Weight

174.24

Appearance

Off-white crystalline powder

Botanical Source

herbs of Arundo donax L.

Structure Type

Alkaloids

Category

Standards;Natural Pytochemical;API

SMILES

CN(C)CC1=CNC2=CC=CC=C21

Synonyms

1H-Indole-3-methanamine, N,N-dimethyl-/Gramin/Donaxine/Indole, 3-[(dimethylamino)methyl]-/Indole,3-[(dimethylamino)methyl]/Gramine/3-(Dimethylaminomethyl)indole/Indol-3-ylmethyldimethylamine/Donaxin/N,N-dimethyl-1H-indole-3-methanamine/3-(N,N-dimethylaminomethyl) indole/N-(1H-indol-3-ylmethyl)-N,N-dimethylamine/1H-Indole-3-methanamine,N,N-dimethyl/1-(1H-Indol-3-yl)-N,N-dimethylmethanamine/3-[(Dimethylamino)methyl]indole/(indol-3-ylmethyl)dimethylamine

IUPAC Name

1-(1H-indol-3-yl)-N,N-dimethylmethanamine

Density

1.1±0.1 g/cm3

Solubility

Methanol; DMSO

Flash Point

131.5±20.4 °C

Boiling Point

293.9±15.0 °C at 760 mmHg

Melting Point

132-134 °C(lit.)

InChl

InChl Key

WGK Germany

RID/ADR

HS Code Reference

2939990000

Personal Projective Equipment

Correct Usage

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

Meta Tag

provides coniferyl ferulate(CAS#:87-52-5) MSDS, density, melting point, boiling point, structure, formula, molecular weight etc. Articles of coniferyl ferulate are included as well.>> amp version: coniferyl ferulate

PMID

29287200

Abstract

Gramine, a natural indole alkaloid found in Hordeum vulgare has been possesses anti-mutagenic properties. The aim of the present study was to evaluate the effect of gramine on inflammation and proliferation in 7,12-dimethylbenz[a]anthracene(DMBA)-induced hamster buccal pouch (HBP) carcinogenesis. Epidermal growth factor receptor (EGFR) tyrosine kinase phosphorylation trigged PI3K/Akt/mTOR and JAK signaling that activates NF-κB and STAT3. In contrast, gramine suppressed EGFR tyrosine kinase phosphorylation and simultaneously inhibiting PI3K/Akt/mTOR and JAK phosphorylation, thereby blockage NF-κB and STAT3 nuclear translocation. Attenuation of these oncogenic signals leads to downregulated iNOS, COX-2, TNF-α, IL-6, cyclin D1 and PCNA protein expressions. In addition, gramine enhanced the expression of the tumor suppressors p53, p21(WAF1/CIP1) and Gsk-3β by inhibiting MDM2. These results suggested that gramine exhibited anti-inflammation and anti-proliferation effects via suppressed EGFR/PI3K/Akt/mTOR/ IKK/NF-κB and JAK/STAT3 signaling pathways.

Copyright © 2017 Elsevier Masson SAS. All rights reserved.

KEYWORDS

DMBA; EGFR; Indole alkaloid; NF-κB; Oral cancer; STAT3

Title

Gramine attenuates EGFR-mediated inflammation and cell proliferation in oral carcinogenesis via regulation of NF-κB and STAT3 signaling.

Author

Ramu A1, Kathiresan S2, Ramadoss H1, Nallu A1, Kaliyan R1, Azamuthu T1.

Publish date

2018 Feb

PMID

28887922

Abstract

BACKGROUND:
Transforming growth factor-β (TGF-β) and its receptors are considered as a novel target in cancer chemotherapy. Gramine, an indole alkaloid, possesses various pharmacological properties including antiproliferative and anticancer. However, the anti-angiogenic property remains unexplored.

PURPOSE:
The present study was designed to evaluate the anti-angiogenic and apoptosis induction properties of gramine through inhibiting TGF-β on DMBA induced oral squamous cell carcinoma (OSCC) in the hamster buccal pouch (HBP).

METHODS:
The effects of gramine on TGF-β signalling in DMBA induced carcinogenic events such as angiogenesis and apoptosis were analysed by studying the mRNA expression using RT-PCR, protein expression by western blot and histopathological analysis using haematoxylin and eosin (H & E) staining.

RESULTS:
Gramine significantly inhibited phosphorylation and nuclear translocation of Smad2 and Smad4 by blocking activity of the TGFβ-RII, RI and activation of inhibitory Smad7. Gramine inhibited angiogenic markers such as MMP-2, MMP-9, HIF-1α, VEGF, and VEGF-R2 as well as increased TIMP-2 expression. Furthermore, gramine induced apoptosis in DMBA induced tumour bearing animals by up regulating the pro apoptotic proteins Bax, cytochrome C, apaf-1, caspase-9 caspase-3 and PARP.

CONCLUSION:
In this study, we clearly demonstrated that gramine treatment diminishes angiogenesis and induces apoptosis in hamster buccal pouch (HBP) carcinogenesis by modulating TGF-β signals.

Copyright © 2017 Elsevier GmbH. All rights reserved.

KEYWORDS

Angiogenesis; Apoptosis; Gramine; Oral cancer; TGF-β

Title

Gramine inhibits angiogenesis and induces apoptosis via modulation of TGF-β signalling in 7,12 dimethylbenz[a]anthracene (DMBA) induced hamster buccal pouch carcinoma.

Author

Ramu A1, Kathiresan S2, Ali Ahmed B3.

Publish date

2017 Sep 15

PMID

11673626

Abstract

Systemic acquired resistance (SAR) is one of the intriguing issues for studying the mechanism in signal transduction system in a whole plant. We found that SAR and increase of an antifungal compound were induced rapidly and transiently in barley (Hordeum vulgare L. cv. Goseshikoku) by mechanical and biological stresses. One of the major antifungal compounds was identified as an indole alkaloid, gramine (N,N-dimethyl-3-aminomethylindole), by mass spectrum and NMR analyses. Gramine is well known as a constitutive compound of barley, but it increased significantly in the primary and secondary leaves of barley seedlings within 12 h after pruning or inoculating with the powdery mildew fungi of barley (Blumeria graminis f.sp. hordei) and wheat (B. graminis f.sp. tritici). However, in the leaf detached from unwounded seedlings or in the leaf inoculated with the barley powdery mildew fungus, gramine did not increase at all. In the water droplets contacted with barley leaves, the amount of leaked gramine increased dependently upon the time after the seedling was injured mechanically. We also found a tight correlation between gramine increase and enhancement of resistance to the barley powdery mildew fungus in barley leaves treated with an endogenous elicitor. Furthermore, such a systemic resistance was not observed in a barley cultivar Morex that lacks the biosynthetic pathway of gramine. From these results, we conclude that gramine is the excellent marker in rapid and transient systemic acquired resistance in barley.

Title

Gramine increase associated with rapid and transient systemic resistance in barley seedlings induced by mechanical and biological stresses.

Author

Matsuo H1, Taniguchi K, Hiramoto T, Yamada T, Ichinose Y, Toyoda K, Takeda K, Shiraishi T.

Publish date

2001 Oct


Description :

Gramine (Donaxine) is a natural alkaloid isolated from giant reed[2], acts as an active adiponectin receptor (AdipoR) agonist, with IC50s of 3.2 and 4.2 µM for AdipoR2 and AdipoR1, respectively[1]. Gramine is also a human and mouse β2-Adrenergic receptor (β2-AR) agonist[2]. Gramine (Donaxine) has anti-tumor, anti-viral and anti-inflammatory properties[1].