Wikipedia

Altohyrtin A

Altohyrtin A (spongistatin 1, cinachyrolide A)[1] is a polyether macrolide originally isolated from the Okinawan marine sponge Hyrtios altum by Kobayashi et al. in 1993,[2] the Indian marine sponge Spongia sp. by Pettit et al. in 1993,[3] and the Japanese marine sponge Cinachyra sp. by Fusetani et al. in 1993.[4] It has potent anti-cancer activity.

Altohyrtin A
Chemical structure of altohyrtin A
Identifiers
3D model (JSmol)
ChemSpider
  • 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
  • C=C(C[C@H]([C@@H](O)[C@@H]1OC(C[C@@H]2O[C@@]3(O[C@@H](CC([C@H]([C@@H]([C@@H](C(C[C@H]4O[C@]5(C[C@@H](O)C[C@H](/C=C\CCC[C@H]6O[C@]7(O)C[C@H](O)[C@H]6C)O5)C[C@@H](OC)C4)=O)C)OC(C)=O)C)=C)C[C@@](O)(C)C3)C[C@@H](OC(C)=O)C2)=O)O[C@@]([C@@H]1C)([H])[C@@H]7O)C[C@H](O)/C=C/C(Cl)=C
Properties
C63H95ClO21
Molar mass 1223.88 g·mol−1
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
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Mechanism of action

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Altohyrtin A binds to the maytansine site on β-tubulin.[5]

Biosynthesis

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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.[6] Alternatively, it may be a bacterial natural product.[1]

See also

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References

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  1. ^ a b 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.
  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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