Altohyrtin A

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Altohyrtin A
Chemical structure of altohyrtin A
Identifiers
3D model (JSmol)
ChemSpider
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  • 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).

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] It was also found in a Indian species of Spongia by Pettit et al,[3] and in a Japanese species of Cinachyra by Fusetani et al.[4] It has potent anti-cancer activity.

Mechanism of action

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Altohyrtin A binds to the maytansine/rhizoxin site on microtubules.[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 bacterial in origin.[1]

See also

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References

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