Basic Description

Synonyms	CHEBI:51015 \| 1o9e \| fuscicoccin A \| FSC \| [(2S)-2-[(1E,3R,4S,8R,9R,10R,11S,14S)-8-[(2S,3R,4S,5R,6R)-4-acetyloxy-3,5-dihydroxy-6-(2-methylbut-3-en-2-yloxymethyl)oxan-2-yl]oxy-4,9-dihydroxy-14-(methoxymethyl)-3,10-dimethyl-6-tricyclo[9.3.0.03,7]tetradeca-1
Specifications & Purity	≥85%
Storage Temp	Store at -20°C
Shipped In	Ice chest + Ice pads
Product Description	Description Fusicoccin (Fusicoccin A), a diterpene glucoside phytotoxin, is used to study 14-3-3-dependent processes such as the activation of H+-ATPase in plants and other client proteins with mode III binding motifs. Fusicoccin is an inducer of a catalase inhibitor that leads to oxidative damage in plants.

Associated Targets(Human)

YWHAZ Tchem 14-3-3 protein zeta/delta (1 Activities)

Discover Target: YWHAZ

Activity Type	Activity Value -log(M)	Mechanism of Action	Activity Reference	Publications (PubMed IDs)

Mechanisms of Action

Mechanism of Action	Action Type	target ID	Target Name	Target Type	Target Organism	Binding Site Name	References

Names and Identifiers

IUPAC Name	[(2S)-2-[(1E,3R,4S,8R,9R,10R,11S,14S)-8-[(2S,3R,4S,5R,6R)-4-acetyloxy-3,5-dihydroxy-6-(2-methylbut-3-en-2-yloxymethyl)oxan-2-yl]oxy-4,9-dihydroxy-14-(methoxymethyl)-3,10-dimethyl-6-tricyclo[9.3.0.03,7]tetradeca-1,6-dienyl]propyl] acetate
INCHI	InChI=1S/C36H56O12/c1-10-35(6,7)45-17-26-30(41)33(46-21(5)38)31(42)34(47-26)48-32-28-24(18(2)15-44-20(4)37)13-27(39)36(28,8)14-25-22(16-43-9)11-12-23(25)19(3)29(32)40/h10,14,18-19,22-23,26-27,29-34,39-42H,1,11-13,15-17H2,2-9H3/b25-14-/t18-,19-,22-,23+,26-,27+,29-,30-,31-,32-,33+,34-,36+/m1/s1
InChi Key	KXTYBXCEQOANSX-WYKQKOHHSA-N
Canonical SMILES	CC1C2CCC(C2=CC3(C(CC(=C3C(C1O)OC4C(C(C(C(O4)COC(C)(C)C=C)O)OC(=O)C)O)C(C)COC(=O)C)O)C)COC
Isomeric SMILES	C[C@@H]1[C@@H]\2CC[C@@H](/C2=C/[C@]3([C@H](CC(=C3[C@H]([C@@H]1O)O[C@@H]4[C@@H]([C@H]([C@@H]([C@H](O4)COC(C)(C)C=C)O)OC(=O)C)O)[C@H](C)COC(=O)C)O)C)COC
PubChem CID	447573
Molecular Weight	680.82

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References

1. D Bowles. (1998-11-04) Signal transduction in the wound response of tomato plants.. Philosophical transactions of the Royal Society of London. Series B, Biological sciences, 353 ((1374)): (1495-1510). [PMID:9800210]
2. A H de Boer. (2002-08-28) Plant 14-3-3 proteins assist ion channels and pumps.. Biochemical Society transactions, 30 ((4)): (416-421). [PMID:12196106]
3. Christian Ottmann,Sergio Marco,Nina Jaspert,Caroline Marcon,Nicolas Schauer,Michael Weyand,Caroline Vandermeeren,Geoffrey Duby,Marc Boutry,Alfred Wittinghofer,Jean-Louis Rigaud,Claudia Oecking. (2007-02-10) Structure of a 14-3-3 coordinated hexamer of the plant plasma membrane H+ -ATPase by combining X-ray crystallography and electron cryomicroscopy.. Molecular cell, 25 ((3)): (427-440). [PMID:17289589]
4. Tomonobu Toyomasu. (2008-05-08) Recent advances regarding diterpene cyclase genes in higher plants and fungi.. Bioscience, biotechnology, and biochemistry, 72 ((5)): (1168-1175). [PMID:18460786]
5. Ingrid J de Vries-van Leeuwen,Chantal Kortekaas-Thijssen,Jean A Nzigou Mandouckou,Sjors Kas,Antonio Evidente,Albertus H de Boer. (2010-02-16) Fusicoccin-A selectively induces apoptosis in tumor cells after interferon-alpha priming.. Cancer letters, 293 ((2)): (198-206). [PMID:20153922]
6. Rolf Rose,Silke Erdmann,Stefanie Bovens,Alexander Wolf,Micheline Rose,Sven Hennig,Herbert Waldmann,Christian Ottmann. (2010-05-04) Identification and structure of small-molecule stabilizers of 14-3-3 protein-protein interactions.. Angewandte Chemie (International ed. in English), 49 ((24)): (4129-4132). [PMID:20437433]
7. A Burian,Z Hejnowicz. (2010-12-15) Fusicoccin affects cortical microtubule orientation in the isolated epidermis of sunflower hypocotyls.. Plant biology (Stuttgart, Germany), 13 ((1)): (201-208). [PMID:21143742]
8. Marten Staal,Tinne De Cnodder,Damien Simon,Filip Vandenbussche,Dominique Van der Straeten,Jean-Pierre Verbelen,Theo Elzenga,Kris Vissenberg. (2011-02-02) Apoplastic alkalinization is instrumental for the inhibition of cell elongation in the Arabidopsis root by the ethylene precursor 1-aminocyclopropane-1-carboxylic acid.. Plant physiology, 155 ((4)): (2049-2055). [PMID:21282405]
9. Lorenzo Camoni,Cristina Di Lucente,Sabina Visconti,Patrizia Aducci. (2011-03-15) The phytotoxin fusicoccin promotes platelet aggregation via 14-3-3-glycoprotein Ib-IX-V interaction.. The Biochemical journal, 436 ((2)): (429-436). [PMID:21395556]
10. Renata Kurtyka,Andrzej Kita,Waldemar Karcz. (2011-03-23) Fusicoccin counteracts the toxic effect of cadmium on the growth of maize coleoptile segments.. Archives of environmental contamination and toxicology, 61 ((4)): (568-577). [PMID:21424219]
11. Michiko Takahashi,Akie Kawamura,Nobuo Kato,Tsuyoshi Nishi,Itaru Hamachi,Junko Ohkanda. (2011-11-23) Phosphopeptide-dependent labeling of 14-3-3\u2009ζ proteins by fusicoccin-based fluorescent probes.. Angewandte Chemie (International ed. in English), 51 ((2)): (509-512). [PMID:22105970]
12. Koshi Kawakami,Miho Hattori,Takatsugu Inoue,Yuriko Maruyama,Junko Ohkanda,Nobuo Kato,Miki Tongu,Takaya Yamada,Miho Akimoto,Keizo Takenaga,Takeshi Sassa,Junji Suzumiy,Yoshio Honma. (2012-01-24) A novel fusicoccin derivative preferentially targets hypoxic tumor cells and inhibits tumor growth in xenografts.. Anti-cancer agents in medicinal chemistry, 12 ((7)): (791-800). [PMID:22263802]
13. Albertus H de Boer,Ingrid J de Vries-van Leeuwen. (2012-04-03) Fusicoccanes: diterpenes with surprising biological functions.. Trends in plant science, 17 ((6)): (360-368). [PMID:22465041]
14. Masaki Okumura,Shin-ichiro Inoue,Koji Takahashi,Kimitsune Ishizaki,Takayuki Kohchi,Toshinori Kinoshita. (2012-04-13) Characterization of the plasma membrane H+-ATPase in the liverwort Marchantia polymorpha.. Plant physiology, 159 ((2)): (826-834). [PMID:22496511]
15. Masaki Okumura,Koji Takahashi,Shin-Ichiro Inoue,Toshinori Kinoshita. (2012-07-28) Evolutionary appearance of the plasma membrane H (+) -ATPase containing a penultimate threonine in the bryophyte.. Plant signaling & behavior, 7 ((8)): (979-982). [PMID:22836495]
16. Lech-Gustav Milroy,Luc Brunsveld,Christian Ottmann. (2012-12-06) Stabilization and inhibition of protein-protein interactions: the 14-3-3 case study.. ACS chemical biology, 8 ((1)): (27-35). [PMID:23210482]
17. Ingrid J De Vries-van Leeuwen,Daniel da Costa Pereira,Koen D Flach,Sander R Piersma,Christian Haase,David Bier,Zeliha Yalcin,Rob Michalides,K Anton Feenstra,Connie R Jiménez,Tom F A de Greef,Luc Brunsveld,Christian Ottmann,Wilbert Zwart,Albertus H de Boer. (2013-05-17) Interaction of 14-3-3 proteins with the estrogen receptor alpha F domain provides a drug target interface.. Proceedings of the National Academy of Sciences of the United States of America, 110 ((22)): (8894-8899). [PMID:23676274]
18. Jan Hlavinka,Jan Nauš,Martin Fellner. (2013-06-14) Spontaneous mutation 7B-1 in tomato impairs blue light-induced stomatal opening.. Plant science : an international journal of experimental plant biology, 209 (75-80). [PMID:23759105]
19. Qi Chen,Chuan-Long Guo,Ping Wang,Xuan-Qin Chen,Kong-Huan Wu,Kui-Zhi Li,Yong-Xiong Yu,Li-Mei Chen. (2013-07-19) Up-regulation and interaction of the plasma membrane H(+)-ATPase and the 14-3-3 protein are involved in the regulation of citrate exudation from the broad bean (Vicia faba L.) under Al stress.. Plant physiology and biochemistry : PPB, 70 (504-511). [PMID:23860230]
20. L Baunsgaard,A T Fuglsang,T Jahn,H A Korthout,A H de Boer,M G Palmgren. (1998-07-29) The 14-3-3 proteins associate with the plant plasma membrane H(+)-ATPase to generate a fusicoccin binding complex and a fusicoccin responsive system.. The Plant journal : for cell and molecular biology, 13 ((5)): (661-671). [PMID:9681008]
21. Krzysztof Bobik,Geoffrey Duby,Yannick Nizet,Caroline Vandermeeren,Patrick Stiernet,Justyna Kanczewska,Marc Boutry. (2010-02-05) Two widely expressed plasma membrane H(+)-ATPase isoforms of Nicotiana tabacum are differentially regulated by phosphorylation of their penultimate threonine.. The Plant journal : for cell and molecular biology, 62 ((2)): (291-301). [PMID:20128881]
22. Enid A C MacRobbie,Wendy D Smyth. (2010-03-20) Effects of fusicoccin on ion fluxes in guard cells.. The New phytologist, 186 ((3)): (636-647). [PMID:20298482]
23. Massimo Malerba,Paolo Crosti,Raffaella Cerana. (2010-07-16) Ethylene is involved in stress responses induced by fusicoccin in sycamore cultured cells.. Journal of plant physiology, 167 ((17)): (1442-1447). [PMID:20630615]
24. Xiao-Ping She,Ai-Xia Huang,Jin Li,Xi-Zhu Han. (2010-07-17) Inhibition of dark-induced stomatal closure by fusicoccin involves a removal of hydrogen peroxide in guard cells of Vicia faba.. Physiologia plantarum, 140 ((3)): (258-268). [PMID:20633238]
25. Yayoi Koizumi,Yoshinao Hara,Yoshiaki Yazaki,Katsuhiro Sakano,Kimiharu Ishizawa. (2011-01-15) Involvement of plasma membrane H+-ATPase in anoxic elongation of stems in pondweed (Potamogeton distinctus) turions.. The New phytologist, 190 ((2)): (421-430). [PMID:21232059]
26. Yusuke Ono,Atsushi Minami,Motoyoshi Noike,Yusuke Higuchi,Tomonobu Toyomasu,Takeshi Sassa,Nobuo Kato,Tohru Dairi. (2011-02-09) Dioxygenases, key enzymes to determine the aglycon structures of fusicoccin and brassicicene, diterpene compounds produced by fungi.. Journal of the American Chemical Society, 133 ((8)): (2548-2555). [PMID:21299202]
27. Nicoletta Beffagna,Marzia Alessandra Riva. (2011-02-16) Fusicoccin-induced catalase inhibitor is produced independently of H+-ATPase activation and behaves as an organic acid.. Physiologia plantarum, 142 ((2)): (144-156). [PMID:21320127]
28. Anja Richter,Christian Hedberg,Herbert Waldmann. (2011-07-16) Enantioselective synthesis of the C10-C20 fragment of fusicoccin A.. The Journal of organic chemistry, 76 ((16)): (6694-6702). [PMID:21755994]
29. Yong Bum Park,Daniel J Cosgrove. (2011-11-24) Changes in cell wall biomechanical properties in the xyloglucan-deficient xxt1/xxt2 mutant of Arabidopsis.. Plant physiology, 158 ((1)): (465-475). [PMID:22108526]
30. Motoyoshi Noike,Chengwei Liu,Yusuke Ono,Yoshimitsu Hamano,Tomonobu Toyomasu,Takeshi Sassa,Nobuo Kato,Tohru Dairi. (2012-01-31) An enzyme catalyzing O-prenylation of the glucose moiety of fusicoccin A, a diterpene glucoside produced by the fungus Phomopsis amygdali.. Chembiochem : a European journal of chemical biology, 13 ((4)): (566-573). [PMID:22287087]
31. Motoyoshi Noike,Yusuke Ono,Yuji Araki,Ryo Tanio,Yusuke Higuchi,Hajime Nitta,Yoshimitsu Hamano,Tomonobu Toyomasu,Takeshi Sassa,Nobuo Kato,Tohru Dairi. (2012-08-08) Molecular breeding of a fungus producing a precursor diterpene suitable for semi-synthesis by dissection of the biosynthetic machinery.. PloS one, 7 ((8)): (e42090-e42090). [PMID:22870285]
32. Malgorzata Skwarczynska,Manuela Molzan,Christian Ottmann. (2012-12-28) Activation of NF-κB signalling by fusicoccin-induced dimerization.. Proceedings of the National Academy of Sciences of the United States of America, 110 ((5)): (E377-E386). [PMID:23269842]
33. Peter K Bjørk,Silas A Rasmussen,Sisse K Gjetting,Nanna W Havshøi,Thomas Isbrandt Petersen,Johan Ø Ipsen,Thomas O Larsen,Anja T Fuglsang. (2019-12-28) Tenuazonic acid from Stemphylium loti inhibits the plant plasma membrane H+ -ATPase by a mechanism involving the C-terminal regulatory domain.. The New phytologist, 226 ((3)): (770-784). [PMID:31880817]

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Fusicoccin from Fusicoccum amygdali - ≥85%, high purity , CAS No.20108-30-9