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SML1635

Sigma-Aldrich

Brassinin

≥98% (HPLC)

Synonyme(s) :

Brassinine, Methyl N-(1H-indol-3-ylmethyl)-carbamodithioate, N-(1H-indol-3-ylmethyl)-carbamodithioic acid methyl ester

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About This Item

Formule empirique (notation de Hill):
C11H12N2S2
Numéro CAS:
105748-59-2
Poids moléculaire :
236.36
Numéro MDL:
MFCD01632490
Code UNSPSC :
12352200
ID de substance PubChem :
329825977
Nomenclature NACRES :
NA.77

Niveau de qualité

100

Pureté

≥98% (HPLC)

Forme

powder

Couleur

white to beige

Solubilité

DMSO: 20 mg/mL, clear

Température de stockage

−20°C

Chaîne SMILES 

S=C(SC)NCC1=CNC2=C1C=CC=C2

InChI

1S/C11H12N2S2/c1-15-11(14)13-7-8-6-12-10-5-3-2-4-9(8)10/h2-6,12H,7H2,1H3,(H,13,14)

Clé InChI

QYKQWFZDEDFELK-UHFFFAOYSA-N

Actions biochimiques/physiologiques

Brassinin is a phytoalexin isolated from cruciferous vegetables that exhibits anticancer, chemopreventive, antiproliferative and antifungal activities. In lung cancer cells, brassinin inhibits constitutive and IL-6-inducible STAT3 signaling through modulation of PIAS-3 and SOCS-3. It appears that brassinin induces apoptosis in PC-3 prostate cancer cells via the suppression of PI3K/Akt/mTOR/S6K1 signaling.

Autres remarques

air sensitive

Code de la classe de stockage

11 - Combustible Solids

Classe de danger pour l'eau (WGK)

WGK 3

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Bobin Kang et al.
The Journal of pharmacy and pharmacology, 72(9), 1245-1255 (2020-05-23)
The effects and molecular mechanisms of brassinin (BR), an indole phytoalexin from cruciferous vegetables, on monocyte-to-macrophage differentiation and inflammatory responses were investigated in this study. Inflammatory responses from RAW264.7 cells and THP-1 were stimulated by lipopolysaccharide (1 µg/ml), and monocyte-to-macrophage differentiation
Taeyeon Hong et al.
Cells, 10(2) (2021-02-11)
Brassinin is a phytochemical derived from Chinese cabbage, a cruciferous vegetable. Brassinin has shown anticancer effects on prostate and colon cancer cells, among others. However, its mechanisms and effects on hepatocellular carcinoma (HCC) have not been elucidated yet. Our results
Andrea Angarita-Rodríguez et al.
Molecules (Basel, Switzerland), 25(1) (2019-12-28)
There is a continuous search for more reliable and effective alternatives to control phytopathogens through different strategies. In this context, indole-containing phytoalexins are stimuli-induced compounds implicated in plant defense against plant pathogens. However, phytoalexins' efficacy have been limited by fungal
Guillaume Quang N'Guyen et al.
Frontiers in plant science, 11, 611643-611643 (2021-02-09)
Alternaria brassicicola causes black spot disease in Brassicaceae. During host infection, this necrotrophic fungus is exposed to various antimicrobial compounds, such as the phytoalexin brassinin which is produced by many cultivated Brassica species. To investigate the cellular mechanisms by which

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