Aplysiatoxin

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Aplysiatoxin
Aplysiatoxin.svg
Names
Other names
Aplysiatoxin
Identifiers
3D model (JSmol)
ChEBI
ChemSpider
PubChem CID
  • InChI=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 Yes check.svgY
    Key: RHJPBGWFGOAEID-BEDNPZBZSA-N Yes check.svgY
  • 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
    Key: RHJPBGWFGOAEID-BEDNPZBZBK
  • 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
Properties
C32H47BrO10
Molar mass 671.614
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
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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. [1] [2] [3] [4] 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. [5] [6] [7]

See also

References

  1. ↑ Kato, Y; Scheuer, PJ (Apr 1974). "Aplysiatoxin and debromoaplysiatoxin, constituents of the marine mollusk Stylocheilus longicauda (Quoy and Gaimard, 1824)". Journal of the American Chemical Society. 96 (7): 2245–6. doi:10.1021/ja00814a041. PMID   4833645.
  2. ↑ Weinstein, IB; Arcoleo, J; Backer, J; et al. (1983). "Molecular mechanisms of tumor promotion and multistage carcinogenesis". Int. Symp. Princess Takamatsu Cancer Res. Fund. 14: 59–74. PMID   6097583.
  3. ↑ Arcoleo, JP; Weinstein, IB (Feb 1985). "Activation of protein kinase C by tumor promoting phorbol esters, teleocidin and aplysiatoxin in the absence of added calcium". Carcinogenesis. 6 (2): 213–7. doi:10.1093/carcin/6.2.213. PMID   3156004.
  4. ↑ Nagai, H; Yasumoto, T; Hokama, Y (Jul 1996). "Aplysiatoxin and debromoaplysiatoxin as the causative agents of a red alga Gracilaria coronopifolia poisoning in Hawaii". Toxicon. 34 (7): 753–61. doi:10.1016/0041-0101(96)00014-1. PMID   8843576.
  5. ↑ Watanabe, M; Kawase, Y; Tanabe, J; Min, KR; Mue, S; Ohuchi, K (Feb 1995). "Suppression of interleukin-1 alpha production by protein kinase C activators in human vascular endothelial cells". Journal of Pharmacology and Experimental Therapeutics. 272 (2): 808–14. PMID   7853198.
  6. ↑ Nakagawa, Y; Yanagita, RC; Hamada, N; Murakami, A; Takahashi, H; Saito, N; Nagai, H; Irie, K (Jun 2009). "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". Journal of the American Chemical Society. 131 (22): 7573–9. doi:10.1021/ja808447r. PMID   19449873.
  7. ↑ Yanagita, RC; Kamachi, H; Tanaka, K; Murakami, A; Nakagawa, Y; Tokuda, H; Nagai, H; Irie, K (Oct 2010). "Role of the phenolic hydroxyl group in the biological activities of simplified analogue of aplysiatoxin with antiproliferative activity". Bioorganic & Medicinal Chemistry Letters. 20 (20): 6064–6. doi:10.1016/j.bmcl.2010.08.051. PMID   20817520.
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