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SML1635

Sigma-Aldrich

Brassinin

≥98% (HPLC)

Synonym(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

Empirical Formula (Hill Notation):
C11H12N2S2
CAS Number:
105748-59-2
Molecular Weight:
236.36
MDL number:
MFCD01632490
UNSPSC Code:
12352200
PubChem Substance ID:
329825977
NACRES:
NA.77

Quality Level

100

Assay

≥98% (HPLC)

form

powder

color

white to beige

solubility

DMSO: 20 mg/mL, clear

storage temp.

−20°C

SMILES string

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)

InChI key

QYKQWFZDEDFELK-UHFFFAOYSA-N

Biochem/physiol Actions

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.

Other Notes

air sensitive

Storage Class Code

11 - Combustible Solids

WGK

WGK 3

Certificates of Analysis (COA)

Search for Certificates of Analysis (COA) by entering the products Lot/Batch Number. Lot and Batch Numbers can be found on a product’s label following the words ‘Lot’ or ‘Batch’.

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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
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
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

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