Altohyrtin A Explained

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.

Mechanism of action

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

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

See also

Notes and References

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

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