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Taichunamides: Prenylated Indole Alkaloids from Aspergillus taichungensis (IBT 19404)
dc.contributor.authorKagiyama, Ippei
dc.contributor.authorKato, Hikaru
dc.contributor.authorNehira, Tatsuo
dc.contributor.authorFrisvad, Jens C.
dc.contributor.authorSherman, David H.
dc.contributor.authorWilliams, Robert M.
dc.contributor.authorTsukamoto, Sachiko
dc.date.accessioned2017-06-16T20:08:14Z
dc.date.available2017-06-16T20:08:14Z
dc.date.issued2016-01-18
dc.identifier.citationKagiyama, Ippei; Kato, Hikaru; Nehira, Tatsuo; Frisvad, Jens C.; Sherman, David H.; Williams, Robert M.; Tsukamoto, Sachiko (2016). "Taichunamides: Prenylated Indole Alkaloids from Aspergillus taichungensis (IBT 19404)." Angewandte Chemie International Edition 55(3): 1128-1132.
dc.identifier.issn1433-7851
dc.identifier.issn1521-3773
dc.identifier.urihttps://hdl.handle.net/2027.42/137233
dc.description.abstractSeven new prenylated indole alkaloids, taichunamides A–G, were isolated from the fungus Aspergillus taichungensis (IBT 19404). Taichunamides A and B contained an azetidine and 4‐pyridone units, respectively, and are likely biosynthesized from notoamide S via (+)‐6‐epi‐stephacidin A. Taichunamides C and D contain endoperoxide and methylsulfonyl units, respectively. This fungus produced indole alkaloids containing an anti‐bicyclo[2.2.2]diazaoctane core, whereas A. protuberus and A. amoenus produced congeners with a syn‐bicyclo[2.2.2]diazaoctane core. Plausible biosynthetic pathways to access these cores within the three species likely arise from an intramolecular hetero Diels–Alder reaction.Magnificent seven: Seven new prenylated indole alkaloids were isolated from A. taichungensis. This fungus produces alkaloids containing an anti‐bicyclo[2.2.2]diazaoctane core, whereas A. protuberus and A. amoenus produce derivatives with a syn‐bicyclo core. The structural diversity of tryptophan‐derived secondary metabolites reveals unusually diverse stereochemical and structural secondary metabolite tailoring functions in these orthologous fungi.
dc.publisherWiley Periodicals, Inc.
dc.subject.otherbiosynthesis
dc.subject.othernatural products
dc.subject.otheralkaloids
dc.subject.othercycloaddition
dc.subject.otherstructure elucidation
dc.titleTaichunamides: Prenylated Indole Alkaloids from Aspergillus taichungensis (IBT 19404)
dc.typeArticleen_US
dc.rights.robotsIndexNoFollow
dc.subject.hlbsecondlevelChemistry
dc.subject.hlbtoplevelScience
dc.description.peerreviewedPeer Reviewed
dc.description.bitstreamurlhttps://deepblue.lib.umich.edu/bitstream/2027.42/137233/1/anie201509462-sup-0001-misc_information.pdf
dc.description.bitstreamurlhttps://deepblue.lib.umich.edu/bitstream/2027.42/137233/2/anie201509462_am.pdf
dc.description.bitstreamurlhttps://deepblue.lib.umich.edu/bitstream/2027.42/137233/3/anie201509462.pdf
dc.identifier.doi10.1002/anie.201509462
dc.identifier.sourceAngewandte Chemie International Edition
dc.identifier.citedreferenceApsperparalines: H. Hayashi, Y. Nishimoto, H. Nozaki, Tetrahedron Lett. 1997, 38, 5655 – 5658;
dc.identifier.citedreferenceT. J. Greshock, A. W. Grubbs, P. Jiao, D. T. Wicklow, J. B. Gloer, R. M. Williams, Angew. Chem. Int. Ed. 2008, 47, 3573 – 3577; Angew. Chem. 2008, 120, 3629 – 3633.
dc.identifier.citedreferenceH. Kato, T. Nakahara, K. Sugimoto, K. Matsuo, I. Kagiyama, J. C. Frisvad, D. H. Sherman, R. M. Williams, S. Tsukamoto, Org. Lett. 2015, 17, 700 – 703.
dc.identifier.citedreferenceS. Cai, Y. Luan, X. Kong, T. Zhu, Q. Gu, D. Li, Org. Lett. 2013, 15, 2168 – 2171.
dc.identifier.citedreference8 – 12 and 21: reference [4];
dc.identifier.citedreference17 and 19: reference 1;
dc.identifier.citedreference18: S. Tsukamoto, H. Umaoka, K. Yoshikawa, T. Ikeda, H. Hirota, J. Nat. Prod. 2010, 73, 1438 – 1440;
dc.identifier.citedreference20: P. S. Steyn, Tetrahedron Lett. 1971, 12, 3331 – 3334.
dc.identifier.citedreferenceR. M. Williams, E. Kwast, H. Coffman, T. Glinka, J. Am. Chem. Soc. 1989, 111, 3064 – 3065.
dc.identifier.citedreferenceK. A. Miller, S. Tsukamoto, R. M. Williams, Nat. Chem. 2009, 1, 63 – 68.
dc.identifier.citedreference 
dc.identifier.citedreferenceBrevianamides: P. S. Steyn, Tetrahedron 1973, 29, 107 – 120;
dc.identifier.citedreferenceMarcfortines: T. Prangé, M.-A. Billion, M. Vuilhorgne, C. Pascard, J. Polonsky, Tetrahedron Lett. 1981, 22, 1977 – 1980;
dc.identifier.citedreferenceParaherquamides: S. E. Blanchflower, R. M. Banks, J. R. Everet, C. Reading, J. Antibiot. 1993, 46, 1355 – 1363;
dc.identifier.citedreferenceOkaramines: S. Murao, H. Hayashi, K. Takiuchi, M. Arai, Agric. Biol. Chem. 1989, 53, 461 – 469;
dc.identifier.citedreferenceSclerotiamide: C. Authrine, J. B. Gloer, J. Nat. Prod. 1996, 59, 1093 – 1095;
dc.identifier.citedreferenceNotoamides: S. Tsukamoto, H. Kato, M. Samizo, Y. Nojiri, H. Onuki, H. Hirota, T. Ohta, J. Nat. Prod. 2008, 71, 2064 – 2067;
dc.identifier.citedreference 
dc.identifier.citedreferenceAvrainvillamide (CJ-17,665): Y. Sugie, H. Hirai, T. Inagaki, M. Ishiguro, Y.-J. Kim, Y. Kojima, T. Sakakibara, S. Sakemi, A. Sugiura, Y. Suzuki, L. Brennan, J. Duignan, L. H. Huang, J. Sutcliffe, N. Kojima, J. Antibiot. 2001, 54, 911 – 916;
dc.identifier.citedreferenceStephacidins: J. Qian-Cutrone, S. Haung, Y.-Z. Shu, D. Vyas, C. Fairchild, Z. Menendez, K. Krampitz, R. Dalterio, S. E. Klohr, Q. Gao, J. Am. Chem. Soc. 2002, 124, 14556 – 14557;
dc.identifier.citedreferenceMalbrancheamides: S. Martínez-Luis, R. Rodríguez, L. Acevedo, M. C. González, A. LiraRocha, R. Mata, Tetrahedron 2006, 62, 1817 – 1822.
dc.identifier.citedreference 
dc.identifier.citedreferenceJ. Kobayashi, J.-F. Cheng, M. Ishibashi, M. R. Wälchli, S. Yamamura, Y. Ohizumi, J. Chem. Soc. Perkin Trans. 1 1991, 1135 – 1137;
dc.identifier.citedreferenceH. Hayashi, K. Takiuchi, S. Murao, M. Arai, Agric. Biol. Chem. 1988, 52, 2131 – 2133;
dc.identifier.citedreferenceM. Kitajima, N. Kogure, K. Yamaguchi, H. Takayama, N. Aimi, Org. Lett. 2003, 5, 2075 – 2078.
dc.identifier.citedreferenceS. Li, K. Srinivasan, H. Tran, F. Yu, J. M. Finefield, J. D. Sunderhaus, T. J. McAfoos, S. Tsukamoto, R. M. Williams, D. H. Sherman, MedChemComm 2012, 3, 987 – 996.
dc.identifier.citedreferenceH. Kato, T. Yoshida, T. Tokue, Y. Nojiri, H. Hirota, T. Ohta, R. M. Williams, S. Tsukamoto, Angew. Chem. Int. Ed. 2007, 46, 2254 – 2256; Angew. Chem. 2007, 119, 2304 – 2306.
dc.owningcollnameInterdisciplinary and Peer-Reviewed


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