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Altohyrtin A

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Altohyrtin A
Chemical structure of altohyrtin A
Identifiers
3D model (JSmol)
ChemSpider
PubChem CID
InChI
  • InChI=1S/C63H95ClO21/c1-33(19-42(67)18-17-35(3)64)20-53-55(72)57-39(7)58(79-53)59(73)63(75)31-51(70)37(5)52(85-63)16-14-12-13-15-44-22-43(68)27-61(81-44)29-47(76-11)23-45(82-61)25-50(69)38(6)56(78-41(9)66)36(4)34(2)21-49-28-60(10,74)32-62(84-49)30-48(77-40(8)65)24-46(83-62)26-54(71)80-57/h13,15,17-18,36-39,42-49,51-53,55-59,67-68,70,72-75H,1-3,12,14,16,19-32H2,4-11H3/b15-13-,18-17+/t36-,37-,38-,39-,42-,43+,44+,45+,46-,47+,48+,49+,51+,52-,53-,55-,56+,57-,58-,59+,60+,61-,62-,63-/m1/s1
  • Key: ICXJVZHDZFXYQC-XKQUEHJYSA-N
SMILES
  • C=C(C((O)1OC(C2O3(O(CC((((C(C4O5(C(O)C(/C=C\CCC6O7(O)C(O)6C)O5)C(OC)C4)=O)C)OC(C)=O)C)=C)C(O)(C)C3)C(OC(C)=O)C2)=O)O(1C)()7O)C(O)/C=C/C(Cl)=C
Properties
Chemical formula C63H95ClO21
Molar mass 1223.88 g·mol
Except where otherwise noted, data are given for materials in their standard state (at 25 °C , 100 kPa). ☒N verify (what is  ?) Infobox references
Chemical compound

Altohyrtin A (spongistatin 1, cinachyrolide A) is a polyether macrolide originally isolated from the Okinawan marine sponge Hyrtios altum by Kobayashi et al. in 1993, the Indian marine sponge Spongia sp. by Pettit et al. in 1993, and the Japanese marine sponge Cinachyra sp. by Fusetani et al. in 1993. It has potent anti-cancer activity.

Mechanism of action

Altohyrtin A binds to the maytansine site on β-tubulin.

Biosynthesis

While a producer organism for Altohyrtin A has never been isolated in pure culture, the structural features of Altohyrtin A, such as the 'odd-even' rule of methylation, and the abundance of oxygen heterocycles, suggest it is a product of dinoflagellate polyether metabolism. Alternatively, it may be a bacterial natural product.

See also

References

  1. ^ Yeung, Kap-Sun; Paterson, Ian (2005-10-21). "Advances in the Total Synthesis of Biologically Important Marine Macrolides". Chemical Reviews. 105 (12). American Chemical Society (ACS): 4237–4313. doi:10.1021/cr040614c. ISSN 0009-2665.
  2. Kobayashi, Motomasa; Aoki, Shunji; Sakai, Haruhiko; Kawazoe, Kazuyoshi; Kihara, Noriaki; Sasaki, Takuma; Kitagawa, Isao (1993). "Altohyrtin A, a potent anti-tumor macrolide from the Okinawan marine sponge Hyrtios altum". Tetrahedron Letters. 34 (17). Elsevier BV: 2795–2798. doi:10.1016/s0040-4039(00)73564-7. ISSN 0040-4039.
  3. Pettit, George R.; Chicacz, Zbigniew A.; Gao, Feng; Herald, Cherry L.; Boyd, Michael R.; Schmidt, Jean M.; Hooper, John N. A. (1993). "Antineoplastic agents. 257. Isolation and structure of spongistatin 1". The Journal of Organic Chemistry. 58 (6). American Chemical Society (ACS): 1302–1304. doi:10.1021/jo00058a004. ISSN 0022-3263.
  4. Fusetani, Nobuhiro; Shinoda, Katsumi; Matsunaga, Shigeki (1993). "Bioactive marine metabolites. 48. Cinachyrolide A: a potent cytotoxic macrolide possessing two spiro ketals from marine sponge Cinachyra sp". Journal of the American Chemical Society. 115 (10). American Chemical Society (ACS): 3977–3981. doi:10.1021/ja00063a017. ISSN 0002-7863.
  5. Menchon, Grégory; Prota, Andrea E.; Lucena-Agell, Daniel; Bucher, Pascal; Jansen, Rolf; Irschik, Herbert; Müller, Rolf; Paterson, Ian; Díaz, J. Fernando; Altmann, Karl-Heinz; Steinmetz, Michel O. (2018-05-29). "A fluorescence anisotropy assay to discover and characterize ligands targeting the maytansine site of tubulin". Nature Communications. 9 (1). Springer Science and Business Media LLC. doi:10.1038/s41467-018-04535-8. ISSN 2041-1723. PMC 5974090.
  6. Van Wagoner, Ryan M.; Satake, Masayuki; Wright, Jeffrey L. C. (2014-06-16). "Polyketide biosynthesis in dinoflagellates: what makes it different?". Natural Product Reports. 31 (9). Royal Society of Chemistry (RSC): 1101. doi:10.1039/c4np00016a. ISSN 0265-0568.
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