Fusicoccin-A

Names

[ CAS No. ]:
20108-30-9

[ Name ]:
Fusicoccin-A

[Synonym ]:
2-[(9aE)-4-{[3-O-Acetyl-6-O-(2-methyl-3-buten-2-yl)hexopyranosyl]oxy}-1,5-dihydroxy-9-(methoxymethyl)-6,10a-dimethyl-1,2,4,5,6,6a,7,8,9,10a-decahydrodicyclopenta[a,d][8]annulen-3-yl]propyl acetate
MFCD00070322
FUSICOCCIN
3-[2-(Acetyloxy)-1-methylethyl]-1,2,4,5,6,6a,7,8,9,10a-decahydro-1,5-dihydroxy-9-(methoxymethyl)-6,10a-dimethylcyclopenta[a,d]-dicylo coten-4-yl-6
Hexopyranoside, (9aE)-3-[2-(acetyloxy)-1-methylethyl]-1,2,4,5,6,6a,7,8,9,10a-decahydro-1,5-dihydroxy-9-(methoxymethyl)-6,10a-dimethyldicyclopenta[a,d]cycloocten-4-yl 6-O-(1,1-dimethyl-2-propen-1-yl)-, 3-acetate
Fucicoccin
fusicoccin A

Biological Activity

[Description]:

Fusicoccin (Fusicoccin A), a fungal pytotoxin, is a stabilizer of specific 14-3-3 protein-protein interactions. Fusicoccin sabilizes H+-ATPase/14-3-3 cmplex in pants, maintaining the enzyme in activated state. Fusicoccin also stabilizes 14-3-3 protein interactions with binding partners containing a C-terminal 14-3-3 recognition motif (a mode 3 motif), such as ERα, GPIbα, TASK3, CTFR, and p53. Fusicoccin induces apoptosis in cancer cells and has anticancer activity[1][2][3][4].

[Related Catalog]:

Signaling Pathways >> Apoptosis >> Apoptosis

Research Areas >> Cancer

[In Vitro]

Fusicoccin (Fusicoccin A) stabilizes a complex between 14-3-3 and the stress response regulator GCN1, inducing GCN1 turnover and neurite outgrowth (EC50=29 mM)[3]. Fusicoccin A activates the plasma membrane H+-ATPase by stabilizing its binding to 14-3-3 proteins, which results in water loss and the wilting of infected plants. Fusicoccin A decreases the proliferation and migration of human GBM cell lines in vitro, including several cell lines that exhibit varying degrees of resistance to pro-apoptotic stimuli. The IC50 growth inhibitory concentration of fusicoccin A is 92 µM in the U373-MG cells and 83 µM in the Hs683 glioma cells[4].

[References]

[1]. Camoni L, et al. The phytotoxin fusicoccin, a selective stabilizer of 14-3-3 interactions?. IUBMB Life. 2013;65(6):513-517.

[2]. Doveston RG, et al. Small-molecule stabilization of the p53-14-3-3 protein-protein interaction. FEBS Lett. 2017;591(16):2449-2457.

[3]. Kaplan A, et al. Small-Molecule Stabilization of 14-3-3 Protein-Protein Interactions Stimulates Axon Regeneration. Neuron. 2017;93(5):1082-1093.e5.

[4]. Bury M, et al. Fusicoccin a, a phytotoxic carbotricyclic diterpene glucoside of fungal origin, reduces proliferation and invasion of glioblastoma cells by targeting multiple tyrosine kinases. Transl Oncol. 2013;6(2):112-123.

Chemical & Physical Properties

[ Density]:
1.2±0.1 g/cm3

[ Boiling Point ]:
760.2±60.0 °C at 760 mmHg

[ Molecular Formula ]:
C₃₆H₅₆O₁₂

[ Molecular Weight ]:
680.823

[ Flash Point ]:
227.0±26.4 °C

[ Exact Mass ]:
680.377197

[ PSA ]:
170.44000

[ LogP ]:
3.28

[ Vapour Pressure ]:
0.0±5.8 mmHg at 25°C

[ Index of Refraction ]:
1.555

MSDS

Click to get detail MSDS

Safety Information

[ Personal Protective Equipment ]:
Eyeshields;Gloves;type N95 (US);type P1 (EN143) respirator filter

[ RIDADR ]:
NONH for all modes of transport

[ WGK Germany ]:
3

Articles

Identification and characterisation of the phenolics of Ilex glabra L. Gray (Aquifoliaceae) leaves by liquid chromatography tandem mass spectrometry.

Plant Physiol. Biochem. 70 , 504-11, (2013)

The phenolics of the leaves of Ilex glabra L. Gray (Aquifoliaceae) were investigated qualitatively by LC-MS(n). Thirty-two phenolics were detected and characterised on the basis of their unique fragme...

Apoplastic alkalinization is instrumental for the inhibition of cell elongation in the Arabidopsis root by the ethylene precursor 1-aminocyclopropane-1-carboxylic acid.

Plant Physiol. 155(4) , 2049-55, (2011)

In Arabidopsis (Arabidopsis thaliana; Columbia-0) roots, the so-called zone of cell elongation comprises two clearly different domains: the transition zone, a postmeristematic region (approximately 20...

Characterization of the plasma membrane H+-ATPase in the liverwort Marchantia polymorpha.

Plant Physiol. 159(2) , 826-34, (2012)

The plasma membrane H(+)-ATPase generates an electrochemical gradient of H(+) across the plasma membrane that provides the driving force for solute transport and regulates pH homeostasis and membrane ...