Chemistry:Altohyrtin A
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Short description: Naturally occurring chemical compound
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| 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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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
Altohyrtin A binds to the maytansine/rhizoxin site on microtubules.[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 bacterial in origin.[1]
See also
References
- ↑ 1.0 1.1 Yeung, Kap-Sun; Paterson, Ian (2005-10-21). "Advances in the Total Synthesis of Biologically Important Marine Macrolides". Chemical Reviews (American Chemical Society (ACS)) 105 (12): 4237–4313. doi:10.1021/cr040614c. ISSN 0009-2665.
- ↑ 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 (Elsevier BV) 34 (17): 2795–2798. doi:10.1016/s0040-4039(00)73564-7. ISSN 0040-4039.
- ↑ 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 (American Chemical Society (ACS)) 58 (6): 1302–1304. doi:10.1021/jo00058a004. ISSN 0022-3263.
- ↑ 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 (American Chemical Society (ACS)) 115 (10): 3977–3981. doi:10.1021/ja00063a017. ISSN 0002-7863.
- ↑ Menchon, Grégory; Prota, Andrea E.; Lucena-Agell, Daniel; Bucher, Pascal; Jansen, Rolf; Irschik, Herbert; Müller, Rolf; Paterson, Ian et al. (2018-05-29). "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). doi:10.1038/s41467-018-04535-8. ISSN 2041-1723.
- ↑ Van Wagoner, Ryan M.; Satake, Masayuki; Wright, Jeffrey L. C. (2014-06-16). "Polyketide biosynthesis in dinoflagellates: what makes it different?". Natural Product Reports (Royal Society of Chemistry (RSC)) 31 (9): 1101. doi:10.1039/c4np00016a. ISSN 0265-0568.
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