{{chembox | Verifiedfields = changed | Watchedfields = changed | verifiedrevid = 455100739 | ImageFile = Aplysiatoxin.svg | ImageSize = | IUPACName = | OtherNames = Aplysiatoxin | Section1 = {{Chembox Identifiers | SMILES = C[C@@H](O)C(CC(O1)=O)OC(C[C@@]2(O)[C@H](C)CC(C)(C)[C@@]3(C[C@H]1[C@H](C)[C@@H]([C@@H](C)CCC(OC)C4=C(Br)C=CC(O)=C4)O3)O2)=O | PubChem = 40465 | CASNo_Ref = {{cascite|correct|??}} | CASNo = 52659-57-1 | ChemSpiderID_Ref = {{chemspidercite|correct|chemspider}} | ChemSpiderID = 10282349 | ChEBI_Ref = {{ebicite|changed|EBI}} | ChEBI = 87016 | InChI = 1/C32H47BrO10/c1-17(8-11-24(39-7)22-12-21(35)9-10-23(22)33)29-19(3)26-15-32(42-29)30(5,6)14-18(2)31(38,43-32)16-28(37)40-25(20(4)34)13-27(36)41-26/h9-10,12,17-20,24-26,29,34-35,38H,8,11,13-16H2,1-7H3/t17-,18+,19-,20+,24-,25+,26-,29+,31-,32-/m0/s1 | InChIKey = RHJPBGWFGOAEID-BEDNPZBZBK | StdInChI_Ref = {{stdinchicite|correct|chemspider}} | StdInChI = 1S/C32H47BrO10/c1-17(8-11-24(39-7)22-12-21(35)9-10-23(22)33)29-19(3)26-15-32(42-29)30(5,6)14-18(2)31(38,43-32)16-28(37)40-25(20(4)34)13-27(36)41-26/h9-10,12,17-20,24-26,29,34-35,38H,8,11,13-16H2,1-7H3/t17-,18+,19-,20+,24-,25+,26-,29+,31-,32-/m0/s1 | StdInChIKey_Ref = {{stdinchicite|correct|chemspider}} | StdInChIKey = RHJPBGWFGOAEID-BEDNPZBZSA-N }} | Section2 = {{Chembox Properties | Formula = C<sub>32</sub>H<sub>47</sub>BrO<sub>10</sub> | MolarMass = 671.614 | Appearance = | MeltingPt = | BoilingPt = | Solubility = }} }}
'''Aplysiatoxin''' is a cyanotoxin produced by certain cyanobacteria species. It is used as a defensive secretion to protect these cyanobacteria from predation by fish, being a potent irritant and carcinogen, by acting as a powerful activator of protein kinase C.<ref>{{cite journal | last1 = Kato | first1 = Y | last2 = Scheuer | first2 = PJ | date = Apr 1974 | title = Aplysiatoxin and debromoaplysiatoxin, constituents of the marine mollusk Stylocheilus longicauda (Quoy and Gaimard, 1824) | url = | journal = Journal of the American Chemical Society | volume = 96 | issue = 7| pages = 2245–6 | doi = 10.1021/ja00814a041 | pmid = 4833645 }}</ref><ref>{{cite journal | pmid = 6097583 | volume=14 | title=Molecular mechanisms of tumor promotion and multistage carcinogenesis | year=1983 | journal=Int. Symp. Princess Takamatsu Cancer Res. Fund | pages=59–74 | last1 = Weinstein | first1 = IB | last2 = Arcoleo | first2 = J | last3 = Backer | first3 = J | display-authors = etal}}</ref><ref>{{cite journal | last1 = Arcoleo | first1 = JP | last2 = Weinstein | first2 = IB | date = Feb 1985 | title = Activation of protein kinase C by tumor promoting phorbol esters, teleocidin and aplysiatoxin in the absence of added calcium | url = | journal = Carcinogenesis | volume = 6 | issue = 2| pages = 213–7 | doi = 10.1093/carcin/6.2.213 | pmid = 3156004 }}</ref><ref>{{cite journal | last1 = Nagai | first1 = H | last2 = Yasumoto | first2 = T | last3 = Hokama | first3 = Y | date = Jul 1996 | title = Aplysiatoxin and debromoaplysiatoxin as the causative agents of a red alga Gracilaria coronopifolia poisoning in Hawaii | url = | journal = Toxicon | volume = 34 | issue = 7| pages = 753–61 | doi = 10.1016/0041-0101(96)00014-1 | pmid = 8843576 }}</ref> While this action has a tumour-promoting effect, protein kinase C activation can be medically beneficial for some other applications, and synthetic analogues of aplysiatoxin have been researched for anti-cancer effects.<ref>{{cite journal | last1 = Watanabe | first1 = M | last2 = Kawase | first2 = Y | last3 = Tanabe | first3 = J | last4 = Min | first4 = KR | last5 = Mue | first5 = S | last6 = Ohuchi | first6 = K | date = Feb 1995 | title = Suppression of interleukin-1 alpha production by protein kinase C activators in human vascular endothelial cells | url = | journal = Journal of Pharmacology and Experimental Therapeutics | volume = 272 | issue = 2| pages = 808–14 | pmid = 7853198 }}</ref><ref>{{cite journal | last1 = Nakagawa | first1 = Y | last2 = Yanagita | first2 = RC | last3 = Hamada | first3 = N | last4 = Murakami | first4 = A | last5 = Takahashi | first5 = H | last6 = Saito | first6 = N | last7 = Nagai | first7 = H | last8 = Irie | first8 = K | date = Jun 2009 | title = A simple analogue of tumor-promoting aplysiatoxin is an antineoplastic agent rather than a tumor promoter: development of a synthetically accessible protein kinase C activator with bryostatin-like activity | url = | journal = Journal of the American Chemical Society | volume = 131 | issue = 22| pages = 7573–9 | pmid = 19449873 | doi = 10.1021/ja808447r }}</ref><ref>{{cite journal | last1 = Yanagita | first1 = RC | last2 = Kamachi | first2 = H | last3 = Tanaka | first3 = K | last4 = Murakami | first4 = A | last5 = Nakagawa | first5 = Y | last6 = Tokuda | first6 = H | last7 = Nagai | first7 = H | last8 = Irie | first8 = K | date = Oct 2010 | title = Role of the phenolic hydroxyl group in the biological activities of simplified analogue of aplysiatoxin with antiproliferative activity | url = | journal = Bioorganic & Medicinal Chemistry Letters | volume = 20 | issue = 20| pages = 6064–6 | pmid = 20817520 | doi = 10.1016/j.bmcl.2010.08.051 | hdl = 2433/130698 | hdl-access = free }}</ref>
==See also== * Debromoaplysiatoxin
== References == {{Reflist}}
{{Cyanotoxins}}
Category:Oxygen heterocycles Category:Cyanotoxins Category:Bromobenzene derivatives Category:Lactones Category:Bromine-containing natural products Category:Enzyme activators Category:Phenols