Literature DB >> 26644336

Taichunamides: Prenylated Indole Alkaloids from Aspergillus taichungensis (IBT 19404).

Ippei Kagiyama1, Hikaru Kato1, Tatsuo Nehira2, Jens C Frisvad3, David H Sherman4, Robert M Williams5,5, Sachiko Tsukamoto6.   

Abstract

Seven 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.
© 2016 WILEY-VCH Verlag GmbH & Co. KGaA, Weinheim.

Entities:  

Keywords:  alkaloids; biosynthesis; cycloaddition; natural products; structure elucidation

Mesh：

Substances：

Year:  2015        PMID： 26644336      PMCID： PMC4960981          DOI： 10.1002/anie.201509462

Source DB:  PubMed          Journal:  Angew Chem Int Ed Engl        ISSN： 1433-7851            Impact factor:   15.336


  13 in total

1.  A new antibiotic CJ-17,665 from Aspergillus ochraceus.

Authors:  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
Journal:  J Antibiot (Tokyo)       Date:  2001-11       Impact factor: 2.649

2.  Stephacidin A and B: two structurally novel, selective inhibitors of the testosterone-dependent prostate LNCaP cells.

Authors:  Jingfang Qian-Cutrone; Stella Huang; Yue-Zhong Shu; Dolatrai Vyas; Craig Fairchild; Ana Menendez; Kimberly Krampitz; Richard Dalterio; Steven E Klohr; Qi Gao
Journal:  J Am Chem Soc       Date:  2002-12-11       Impact factor: 15.419

3.  Notoamides A-D: prenylated indole alkaloids isolated from a marine-derived fungus, Aspergillus sp.

Authors:  Hikaru Kato; Takushi Yoshida; Takanori Tokue; Yuka Nojiri; Hiroshi Hirota; Tomihisa Ohta; Robert M Williams; Sachiko Tsukamoto
Journal:  Angew Chem Int Ed Engl       Date:  2007       Impact factor: 15.336

4.  Notoamides F-K, prenylated indole alkaloids isolated from a marine-derived Aspergillus sp.

Authors:  Sachiko Tsukamoto; Hikaru Kato; Masayuki Samizo; Yuka Nojiri; Hiroyuki Onuki; Hiroshi Hirota; Tomihisa Ohta
Journal:  J Nat Prod       Date:  2008-12       Impact factor: 4.050

5.  Structure reinvestigation of gelsemoxonine, a constituent of Gelsemium elegans, reveals a novel, azetidine-containing indole alkaloid.

Authors:  Mariko Kitajima; Noriyuki Kogure; Kentaro Yamaguchi; Hiromitsu Takayama; Norio Aimi
Journal:  Org Lett       Date:  2003-06-12       Impact factor: 6.005

6.  Isolation, structure elucidation, and biomimetic total synthesis of versicolamide B, and the isolation of antipodal (-)-stephacidin A and (+)-notoamide B from Aspergillus versicolor NRRL 35600.

Authors:  Thomas J Greshock; Alan W Grubbs; Ping Jiao; Donald T Wicklow; James B Gloer; Robert M Williams
Journal:  Angew Chem Int Ed Engl       Date:  2008       Impact factor: 15.336

7.  Asymmetric total syntheses of (+)- and (-)-versicolamide B and biosynthetic implications.

Authors:  Kenneth A Miller; Sachiko Tsukamoto; Robert M Williams
Journal:  Nat Chem       Date:  2009-04       Impact factor: 24.427

8.  Sclerotiamide: a new member of the paraherquamide class with potent antiinsectan activity from the sclerotia of Aspergillus sclerotiorum.

Authors:  A C Whyte; J B Gloer; D T Wicklow; P F Dowdw
Journal:  J Nat Prod       Date:  1996-11       Impact factor: 4.050

9.  Notoamide O, a structurally unprecedented prenylated indole alkaloid, and notoamides P-R from a marine-derived fungus, Aspergillus sp.

Authors:  Sachiko Tsukamoto; Hideharu Umaoka; Kohei Yoshikawa; Tsuyoshi Ikeda; Hiroshi Hirota
Journal:  J Nat Prod       Date:  2010-08-27       Impact factor: 4.050

10.  Isolation of notoamide S and enantiomeric 6-epi-stephacidin A from the fungus Aspergillus amoenus: biogenetic implications.

Authors:  Hikaru Kato; Takashi Nakahara; Kayo Sugimoto; Kanae Matsuo; Ippei Kagiyama; Jens C Frisvad; David H Sherman; Robert M Williams; Sachiko Tsukamoto
Journal:  Org Lett       Date:  2015-01-23       Impact factor: 6.005
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  13 in total

1.  Isolation of amoenamide A and five antipodal prenylated alkaloids from Aspergillus amoenus NRRL 35600.

Authors:  Kayo Sugimoto; Yusaku Sadahiro; Ippei Kagiyama; Hikaru Kato; David H Sherman; Robert M Williams; Sachiko Tsukamoto
Journal:  Tetrahedron Lett       Date:  2017-05-18       Impact factor: 2.415

2.  Ceylonins G-I: spongian diterpenes from the marine sponge Spongia ceylonensis.

Authors:  Ahmed H El-Desoky; Hikaru Kato; Sachiko Tsukamoto
Journal:  J Nat Med       Date:  2017-05-03       Impact factor: 2.343

3.  New geranyl flavonoids from the leaves of Artocarpus communis.

Authors:  Masamitsu Inoue; Yuki Hitora; Hikaru Kato; Fitje Losung; Remy E P Mangindaan; Sachiko Tsukamoto
Journal:  J Nat Med       Date:  2018-02-24       Impact factor: 2.343

4.  Enantioselective inhibitory abilities of enantiomers of notoamides against RANKL-induced formation of multinuclear osteoclasts.

Authors:  Hikaru Kato; Aika Kai; Tetsuro Kawabata; James D Sunderhaus; Timothy J McAfoos; Jennifer M Finefield; Yukihiko Sugimoto; Robert M Williams; Sachiko Tsukamoto
Journal:  Bioorg Med Chem Lett       Date:  2017-10-09       Impact factor: 2.823

5.  Polyhalonitrobutadienes as Versatile Building Blocks for the Biotargeted Synthesis of Substituted N-Heterocyclic Compounds.

Authors:  Viktor A Zapol'skii; Ursula Bilitewski; Sören R Kupiec; Isabell Ramming; Dieter E Kaufmann
Journal:  Molecules       Date:  2020-06-21       Impact factor: 4.411

6.  Classification of Aspergillus, Penicillium, Talaromyces and related genera (Eurotiales): An overview of families, genera, subgenera, sections, series and species.

Authors:  J Houbraken; S Kocsubé; C M Visagie; N Yilmaz; X-C Wang; M Meijer; B Kraak; V Hubka; K Bensch; R A Samson; J C Frisvad
Journal:  Stud Mycol       Date:  2020-06-27       Impact factor: 16.097

7.  2,5-Diketopiperazines From a Sponge-Derived Fungus Aspergillus sclerotiorum.

Authors:  Chao-Yi Wang; Xiao-Han Liu; Yao-Yao Zheng; Xing-Yan Ning; Ya-Hui Zhang; Xiu-Mei Fu; Xin Li; Chang-Lun Shao; Chang-Yun Wang
Journal:  Front Microbiol       Date:  2022-05-20       Impact factor: 6.064

Review 8.  Enzyme evolution in fungal indole alkaloid biosynthesis.

Authors:  Amy E Fraley; David H Sherman
Journal:  FEBS J       Date:  2020-04       Impact factor: 5.542

Review 9.  Structural and stereochemical diversity in prenylated indole alkaloids containing the bicyclo[2.2.2]diazaoctane ring system from marine and terrestrial fungi.

Authors:  Kimberly R Klas; Hikaru Kato; Jens C Frisvad; Fengan Yu; Sean A Newmister; Amy E Fraley; David H Sherman; Sachiko Tsukamoto; Robert M Williams
Journal:  Nat Prod Rep       Date:  2018-06-20       Impact factor: 13.423

10.  Characterization of Aspergillus fumigatus Isolates from Air and Surfaces of the International Space Station.

Authors:  Benjamin P Knox; Adriana Blachowicz; Jonathan M Palmer; Jillian Romsdahl; Anna Huttenlocher; Clay C C Wang; Nancy P Keller; Kasthuri Venkateswaran
Journal:  mSphere       Date:  2016-10-26       Impact factor: 4.389
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