R5648

Rottlerin

• Synonym(s): 1-[6-[(3-Acetyl-2,4,6-trihydroxy-5-methylphenyl)methyl]-5,7-dihydroxy-2,2-dimethyl-2H-1-benzopyran-8-yl]-3-phenyl-2-propen-1-one, Mallotoxin
• Empirical Formula (Hill Notation): C₃₀H₂₈O₈
• CAS Number: 82-08-6
• Molecular Weight: 516.54
• EC Number: 201-395-4
• MDL number: MFCD00017361
• UNSPSC Code: 12352200
• PubChem Substance ID: 24278679
• NACRES: NA.77

Properties

• biological source: plant (Mallotus philippinensis)
• assay: ≥95% (HPLC)
• form: powder
• mp: 200.0 °C
• solubility: ethanol: 1 mg/mL
• storage temp.: 2-8°C
• SMILES string: CC(=O)c1c(O)c(C)c(O)c(Cc2c(O)c3C=CC(C)(C)Oc3c(c2O)C(=O)\C=C\c4ccccc4)c1O
• InChI: 1S/C30H28O8/c1-15-24(33)19(27(36)22(16(2)31)25(15)34)14-20-26(35)18-12-13-30(3,4)38-29(18)23(28(20)37)21(32)11-10-17-8-6-5-7-9-17/h5-13,33-37H,14H2,1-4H3/b11-10+
• InChI key: DEZFNHCVIZBHBI-ZHACJKMWSA-N
• Gene Information: human ... CDK2(1017)

Description

General description

Rottlerin is extracted from Mallotus philippinensis.[1] It is a protein kinase Cδ (PKCδ) inhibitor. Rottlerin acts as an uncoupler of mitochondrial respiration from oxidative phosphorylation.[2] It has antitumor, autophagy, anti-proliferative, anti-metastasis and anti-invasive properties.[3]

Application

Rottlerin has been used:

• as a protein kinase C δ (PKCδ) inhibitor for the analysis of protein content and phosphorylation in rats[4]
• to examine the gene expression of early osteoblast markers[5]
• to attenuate pyruvate dehydrogenase (PDH) phosphorylation by succinate[6]
• to depolarise mitochondria[7]
• to investigate its antitumor activity in pancreatic cancer (PC) cells[8]

Biochem/physiol Actions

Potent activator of the large conductance voltage and Ca²⁺ activated K⁺ channel; hERG channel activator.

Recently, Rottlerin (mallotoxin) has been shown to be a potent activator of the large conductance voltage and Ca² activated K⁺ channel and to potently leftward shift the conductance-voltage relationship of the channel. Mallatoxin tested on hERG channels increased both step and tail hERG current by leftward shifting the voltage dependence of hERG activation and slowing channel deactivation. These actions distinguish Mallatoxin as a novel naturally occurring hERG channel activator.

Features and Benefits

This compound is featured on the PKC page of the Handbook of Receptor Classification and Signal Transduction. To browse other handbook pages, click here.

Safety Information

• Storage Class: 13 - Non Combustible Solids
• wgk_germany: WGK 3
• flash_point_f: Not applicable
• flash_point_c: Not applicable
• ppe: Eyeshields, Gloves, type N95 (US)