Abstract
Two new cytotoxic antibiotics, piericidins C7 (1) and C8 (2), were isolated from a marine Streptomyces sp. High-resolution FAB-MS established the molecular formulae of 1 and 2 as C28H41NO5 and C29H43NO5, respectively. The planar structures of the piericidins were elucidated by NMR spectral analysis including COSY, HMQC and HMBC. The relative stereochemistry of 2 was determined based on NOESY and coupling constant analyses. 1 and 2 are new members of the piericidin family possessing 11,12-epoxide and 12-butenyl groups.
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Hayakawa Y, Shirasaki S, Shiba S, Kawasaki T, Matsuo Y, Adachi K, Shizuri Y . Piericidins C7 and C8, new cytotoxic antibiotics produced by a marine Streptomyces sp. J Antibiot 60: 196–200 ( 2007)
Summers MF, Marzilli LG, Bax A . Complete 1H and 13C assignments of coenzyme B12 through the use of new two-dimensional NMR experiments. J Am Chem Soc 108: 4285–4294 ( 1986)
Bax A, Summers MF . 1H and 13C assignments from sensitivity enhanced detection of heteronuclear multiple-bond connectivity by multiple quantum NMR. J Am Chem Soc 108: 2093–2094 ( 1986)
Tamura S, Takahashi N, Miyamoto S, Mori R, Suzuki S, Nagatsu J . Isolation and biological activities of piericidin A, a natural insecticide produced by Streptomyces. Agric Biol Chem 27: 576–582 ( 1963)
Yoshida S, Yonezawa K, Shiraishi S, Watanabe A, Takahashi N . Isolation and physical properties of new piericidins produced by Streptomyces pactum. Agric Biol Chem 41: 849–853 ( 1977)
Yoshida S, Yonezawa K, Shiraishi S, Watanabe A, Takahashi N . Chemical structures of new piericidins produced by Streptomyces pactum. Agric Biol Chem 41: 855–862 ( 1977)
Kubota NK, Ohta E, Ohta S, Koizumi F, Suzuki M, Ichimura M, Ikegami S . Piericidins C5 and C6: new 4-pyridinol compounds produced by Streptomyces sp. and Nocardioides sp. Bioorg Med Chem 11: 4569–4575 ( 2003)
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Hayakawa, Y., Shirasaki, S., Kawasaki, T. et al. Structures of New Cytotoxic Antibiotics, Piericidins C7 and C8. J Antibiot 60, 201–203 (2007). https://doi.org/10.1038/ja.2007.23
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DOI: https://doi.org/10.1038/ja.2007.23
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