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20108-30-9,MFCD00070322
Catalog No.:AA00BCGT

20108-30-9 | FUSICOCCIN

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Technical Information
Catalog Number:
AA00BCGT
Chemical Name:
FUSICOCCIN
CAS Number:
20108-30-9
Molecular Formula:
C36H56O12
Molecular Weight:
680.8226
MDL Number:
MFCD00070322
SMILES:
COC[C@@H]1CC[C@H]2C1=C[C@@]1(C)[C@H](O)CC(=C1[C@@H]([C@H]([C@@H]2C)O)O[C@H]1O[C@@H](COC(C=C)(C)C)[C@@H]([C@H]([C@@H]1O)OC(=O)C)O)[C@@H](COC(=O)C)C
Properties
Computed Properties
 
Complexity:
1240  
Covalently-Bonded Unit Count:
1  
Heavy Atom Count:
48  
Hydrogen Bond Acceptor Count:
12  
Hydrogen Bond Donor Count:
4  
Rotatable Bond Count:
14  
Undefined Atom Stereocenter Count:
13  
Undefined Bond Stereocenter Count:
1  
XLogP3:
1  

Literature

Title: A novel fusicoccin derivative preferentially targets hypoxic tumor cells and inhibits tumor growth in xenografts.

Journal: Anti-cancer agents in medicinal chemistry 20120901

Title: Evolutionary appearance of the plasma membrane H (+) -ATPase containing a penultimate threonine in the bryophyte.

Journal: Plant signaling & behavior 20120801

Title: Fusicoccanes: diterpenes with surprising biological functions.

Journal: Trends in plant science 20120601

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

Journal: Plant physiology 20120601

Title: An enzyme catalyzing O-prenylation of the glucose moiety of fusicoccin A, a diterpene glucoside produced by the fungus Phomopsis amygdali.

Journal: Chembiochem : a European journal of chemical biology 20120305

Title: Phosphopeptide-dependent labeling of 14-3-3 ζ proteins by fusicoccin-based fluorescent probes.

Journal: Angewandte Chemie (International ed. in English) 20120109

Title: Changes in cell wall biomechanical properties in the xyloglucan-deficient xxt1/xxt2 mutant of Arabidopsis.

Journal: Plant physiology 20120101

Title: Molecular breeding of a fungus producing a precursor diterpene suitable for semi-synthesis by dissection of the biosynthetic machinery.

Journal: PloS one 20120101

Title: Fusicoccin counteracts the toxic effect of cadmium on the growth of maize coleoptile segments.

Journal: Archives of environmental contamination and toxicology 20111101

Title: Enantioselective synthesis of the C10-C20 fragment of fusicoccin A.

Journal: The Journal of organic chemistry 20110819

Title: Fusicoccin-induced catalase inhibitor is produced independently of H+-ATPase activation and behaves as an organic acid.

Journal: Physiologia plantarum 20110601

Title: The phytotoxin fusicoccin promotes platelet aggregation via 14-3-3-glycoprotein Ib-IX-V interaction.

Journal: The Biochemical journal 20110601

Title: Involvement of plasma membrane H+-ATPase in anoxic elongation of stems in pondweed (Potamogeton distinctus) turions.

Journal: The New phytologist 20110401

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

Journal: Plant physiology 20110401

Title: Dioxygenases, key enzymes to determine the aglycon structures of fusicoccin and brassicicene, diterpene compounds produced by fungi.

Journal: Journal of the American Chemical Society 20110302

Title: Fusicoccin affects cortical microtubule orientation in the isolated epidermis of sunflower hypocotyls.

Journal: Plant biology (Stuttgart, Germany) 20110101

Title: Ethylene is involved in stress responses induced by fusicoccin in sycamore cultured cells.

Journal: Journal of plant physiology 20101115

Title: Inhibition of dark-induced stomatal closure by fusicoccin involves a removal of hydrogen peroxide in guard cells of Vicia faba.

Journal: Physiologia plantarum 20101101

Title: Fusicoccin-A selectively induces apoptosis in tumor cells after interferon-alpha priming.

Journal: Cancer letters 20100728

Title: Identification and structure of small-molecule stabilizers of 14-3-3 protein-protein interactions.

Journal: Angewandte Chemie (International ed. in English) 20100601

Title: Effects of fusicoccin on ion fluxes in guard cells.

Journal: The New phytologist 20100501

Title: Two widely expressed plasma membrane H(+)-ATPase isoforms of Nicotiana tabacum are differentially regulated by phosphorylation of their penultimate threonine.

Journal: The Plant journal : for cell and molecular biology 20100401

Title: Plasma membrane H-ATPase-dependent citrate exudation from cluster roots of phosphate-deficient white lupin.

Journal: Plant, cell & environment 20090501

Title: A structural rationale for selective stabilization of anti-tumor interactions of 14-3-3 proteins by cotylenin A.

Journal: Journal of molecular biology 20090306

Title: System potentials, a novel electrical long-distance apoplastic signal in plants, induced by wounding.

Journal: Plant physiology 20090301

Title: Stimulation of seed germination of Orobanche species by ophiobolin A and fusicoccin derivatives.

Journal: Journal of agricultural and food chemistry 20080924

Title: Light response of hydraulic conductance in bur oak (Quercus macrocarpa) leaves.

Journal: Tree physiology 20080701

Title: Role of nitric oxide in actin depolymerization and programmed cell death induced by fusicoccin in sycamore (Acer pseudoplatanus) cultured cells.

Journal: Physiologia plantarum 20080601

Title: Cell division versus cell elongation: the control of radicle elongation during thermoinhibition of Tagetes minuta achenes.

Journal: Journal of plant physiology 20071201

Title: Strategies to search and design stabilizers of protein-protein interactions: a feasibility study.

Journal: Proteins 20070701

Title: Changes in extracellular pH are neither required nor sufficient for activation of mitogen-activated protein kinases (MAPKs) in response to systemin and fusicoccin in tomato.

Journal: Planta 20070501

Title: Fusicoccins are biosynthesized by an unusual chimera diterpene synthase in fungi.

Journal: Proceedings of the National Academy of Sciences of the United States of America 20070227

Title: Structure of a 14-3-3 coordinated hexamer of the plant plasma membrane H+ -ATPase by combining X-ray crystallography and electron cryomicroscopy.

Journal: Molecular cell 20070209

Title: Membrane effects of 2,4-dichlorophenoxyacetic acid in motor cells of Mimosa pudica L.

Journal: Plant physiology and biochemistry : PPB 20070101

Title: Cyclosporin A inhibits programmed cell death and cytochrome c release induced by fusicoccin in sycamore cells.

Journal: Protoplasma 20070101

Title: Inhibition of catalase activity as an early response of Arabidopsis thaliana cultured cells to the phytotoxin fusicoccin.

Journal: Journal of experimental botany 20070101

Title: The fern Adiantum capillus-veneris lacks stomatal responses to blue light.

Journal: Plant & cell physiology 20060601

Title: Arabidopsis HT1 kinase controls stomatal movements in response to CO2.

Journal: Nature cell biology 20060401

Title: The Agrobacterium vitis T-6b oncoprotein induces auxin-independent cell expansion in tobacco.

Journal: The Plant journal : for cell and molecular biology 20060301

Title: Acid growth and plant development.

Journal: Science (New York, N.Y.) 20060217

Title: Stimulation of Orobanche ramosa seed germination by fusicoccin derivatives: a structure-activity relationship study.

Journal: Phytochemistry 20060101

Title: Characterization of the interaction between the plasma membrane H-ATPase of Arabidopsis thaliana and a novel interactor (PPI1).

Journal: The FEBS journal 20051101

Title: Studies towards the total synthesis of di- and sesterterpenes with dicyclopenta[a,d]cyclooctane skeletons. Three-component approach to the A/B rings building block.

Journal: Molecules (Basel, Switzerland) 20050930

Title: A link between citrate and proton release by proteoid roots of white lupin (Lupinus albus L.) grown under phosphorus-deficient conditions?

Journal: Plant & cell physiology 20050601

Title: Spatial coordination of chloroplast and plasma membrane activities in Chara cells and its disruption through inactivation of 14-3-3 proteins.

Journal: Biochemistry. Biokhimiia 20050101

Title: [Capacity of fusicoccin for inducing the production of early interferon].

Journal: Zhurnal mikrobiologii, epidemiologii, i immunobiologii 20050101

Title: [The capacity of fusicoccin for inducing the synthesis of early interferon].

Journal: Zhurnal mikrobiologii, epidemiologii, i immunobiologii 20050101

Title: [The role of proton pump and potassium channels of plasma membrane in regulation of cellulose synthesis in plants].

Journal: Tsitologiia 20050101

Title: Comparison between the effects of fusicoccin, Tunicamycin, and Brefeldin A on programmed cell death of cultured sycamore (Acer pseudoplatanus L.) cells.

Journal: Protoplasma 20041001

Title: Identification of (+)-phyllocladene, (--)-sandaracopimaradiene, and (+)-kaurene as new fungal metabolites from fusicoccin-producing Phomopsis amygdali F6.

Journal: Bioscience, biotechnology, and biochemistry 20040701

Title: Fusicocca-3(16),10(14)-diene, and beta- and delta-araneosenes, new fusicoccin biosynthesis-related diterpene hydrocarbons from Phomopsis amygdali.

Journal: Bioscience, biotechnology, and biochemistry 20040701

Title: Fusicoccin activates pathogen-responsive gene expression independently of common resistance signalling pathways, but increases disease symptoms in Pseudomonas syringae-infected tomato plants.

Journal: Planta 20040601

Title: Microtubules of guard cells are light sensitive.

Journal: Plant & cell physiology 20040501

Title: Characterization of sterol uptake in leaf tissues of sugar beet.

Journal: Planta 20031201

Title: The diageotropica mutation of tomato disrupts a signalling chain using extracellular auxin binding protein 1 as a receptor.

Journal: Planta 20031201

Title: Fusicoccin signaling reveals 14-3-3 protein function as a novel step in left-right patterning during amphibian embryogenesis.

Journal: Development (Cambridge, England) 20031001

Title: Sugar uptake and proton release by protoplasts from the infected zone of Vicia faba L. nodules: evidence against apoplastic sugar supply of infected cells.

Journal: Journal of experimental botany 20030701

Title: Structural view of a fungal toxin acting on a 14-3-3 regulatory complex.

Journal: The EMBO journal 20030303

Title: (+)-Menthol and its hydroxy derivatives, novel fungal monoterpenols from the fusicoccin-producing fungi, Phomopsis amygdali F6a and Niigata 2.

Journal: Bioscience, biotechnology, and biochemistry 20030301

Title: Two azuki bean XTH genes, VaXTH1 and VaXTH2, with similar tissue-specific expression profiles, are differently regulated by auxin.

Journal: Plant & cell physiology 20030101

Title: Fusicoccin induces in plant cells a programmed cell death showing apoptotic features.

Journal: Protoplasma 20030101

Title: Metabolic enzymes as targets for 14-3-3 proteins.

Journal: Plant molecular biology 20021201

Title: Requirements for activation of the signal-transduction network that leads to regulatory phosphorylation of leaf guard-cell phosphoenolpyruvate carboxylase during fusicoccin-stimulated stomatal opening.

Journal: Archives of biochemistry and biophysics 20021101

Title: cDNA microarray analysis of fusicoccin-induced changes in gene expression in tomato plants.

Journal: Planta 20021101

Title: Biochemical evidence for the requirement of 14-3-3 protein binding in activation of the guard-cell plasma membrane H+-ATPase by blue light.

Journal: Plant & cell physiology 20021101

Title: Fusicoccins P and Q, and 3-epifusicoccins H and Q, new polar fusicoccins from isolate Niigata 2-A of a peach Fusicoccum canker fungus.

Journal: Bioscience, biotechnology, and biochemistry 20021101

Title: Ultraviolet-B activates components of the systemin signaling pathway in Lycopersicon peruvianum suspension-cultured cells.

Journal: The Journal of biological chemistry 20020809

Title: A novel interaction partner for the C-terminus of Arabidopsis thaliana plasma membrane H+-ATPase (AHA1 isoform): site and mechanism of action on H+-ATPase activity differ from those of 14-3-3 proteins.

Journal: The Plant journal : for cell and molecular biology 20020801

Title: Mechanism of cell death and disease resistance induction by transgenic expression of bacterio-opsin.

Journal: The Plant journal : for cell and molecular biology 20020601

Title: Evidence for high activity of xylem parenchyma and ray cells in the interface of host stem and Agrobacterium tumefaciens-induced tumours of Ricinus communis.

Journal: Journal of experimental botany 20020501

Title: Do 14-3-3 proteins and plasma membrane H+-AtPases interact in the barley epidermis in response to the barley powdery mildew fungus?

Journal: Plant molecular biology 20020501

Title: The apoplastic pH of the substomatal cavity of Vicia faba leaves and its regulation responding to different stress factors.

Journal: Journal of experimental botany 20020101

Title: Binding of regulatory 14-3-3 proteins to the C terminus of the plant plasma membrane H+ -ATPpase involves part of its autoinhibitory region.

Journal: The Journal of biological chemistry 20011026

Title: 14-3-3 protein-activated and autoinhibited forms of plasma membrane H(+)-ATPase.

Journal: Biochemical and biophysical research communications 20010907

Title: Guard-cell chloroplasts provide ATP required for H(+) pumping in the plasma membrane and stomatal opening.

Journal: Plant & cell physiology 20010801

Title: Large scale expression, purification and 2D crystallization of recombinant plant plasma membrane H+-ATPase.

Journal: Journal of molecular biology 20010601

Title: Molecular and physiological characterisation of a 14-3-3 protein from lily pollen grains regulating the activity of the plasma membrane H+ ATPase during pollen grain germination and tube growth.

Journal: Planta 20010501

Title: Auxin-induced elongation of short maize coleoptile segments is supported by 2,4-dihydroxy-7-methoxy-1,4-benzoxazin-3-one.

Journal: Planta 20010501

Title: Analysis of the phosphorylation level in guard-cell plasma membrane H+-ATPase in response to fusicoccin.

Journal: Plant & cell physiology 20010401

Title: Salinity-induced inhibition of leaf elongation in maize is not mediated by changes in cell wall acidification capacity.

Journal: Plant physiology 20010301

Title: Plasma-membrane H+-ATPases are expressed in pitchers of the carnivorous plant Nepenthes alata Blanco.

Journal: Planta 20010301

Title: Specific binding of vf14-3-3a isoform to the plasma membrane H+-ATPase in response to blue light and fusicoccin in guard cells of broad bean.

Journal: Plant physiology 20010201

Title: Fusicoccin- and IAA-induced elongation growth share the same pattern of K+ dependence.

Journal: Journal of experimental botany 20010201

Title: Induction of wound response gene expression in tomato leaves by ionophores.

Journal: Planta 20010201

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

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

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

Title: 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.

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