Literature DB >> 19292484

Isolation of notoamide E, a key precursor in the biosynthesis of prenylated indole alkaloids in a marine-derived fungus, Aspergillus sp.

Sachiko Tsukamoto1, Hikaru Kato, Thomas J Greshock, Hiroshi Hirota, Tomihisa Ohta, Robert M Williams.   

Abstract

Notoamide E was identified to be a short-lived precursor in the biosynthesis of prenylated indole alkaloids in the mussel-derived Aspergillus sp. In addition, the feeding experiment of the (13)C-labeled notoamide E afforded structurally novel metabolites.

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Year:  2009        PMID： 19292484      PMCID： PMC2671082          DOI： 10.1021/ja810029b

Source DB:  PubMed          Journal:  J Am Chem Soc        ISSN： 0002-7863            Impact factor:   15.419


  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.  New paraherquamide antibiotics with anthelmintic activity.

Authors:  S E Blanchflower; R M Banks; J R Everett; B R Manger; C Reading
Journal:  J Antibiot (Tokyo)       Date:  1991-05       Impact factor: 2.649

4.  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

5.  Studies in relation to biosynthesis. XLII. The structural elucidation and some aspects of the biosynthesis of the brevianamides-A and -E.

Authors:  A J Birch; J J Wright
Journal:  Tetrahedron       Date:  1970-05       Impact factor: 2.457

6.  Novel antinematodal and antiparasitic agents from Penicillium charlesii. II. Structure determination of paraherquamides B, C, D, E, F, and G.

Authors:  J M Liesch; C F Wichmann
Journal:  J Antibiot (Tokyo)       Date:  1990-11       Impact factor: 2.649

7.  Novel antinematodal and antiparasitic agents from Penicillium charlesii. I. Fermentation, isolation and biological activity.

Authors:  J G Ondeyka; R T Goegelman; J M Schaeffer; L Kelemen; L Zitano
Journal:  J Antibiot (Tokyo)       Date:  1990-11       Impact factor: 2.649

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.  Short, enantioselective total synthesis of okaramine N.

Authors:  Phil S Baran; Carlos A Guerrero; E J Corey
Journal:  J Am Chem Soc       Date:  2003-05-14       Impact factor: 15.419

10.  Further novel metabolites of the paraherquamide family.

Authors:  S E Blanchflower; R M Banks; J R Everett; C Reading
Journal:  J Antibiot (Tokyo)       Date:  1993-09       Impact factor: 2.649
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  27 in total

1.  Study on the biosynthesis of the notoamides: Pinacol-type rearrangement of the isoprenyl unit in deoxybrevianamide E and 6-hydroxydeoxybrevianamide E.

Authors:  Hikaru Kato; Yuichi Nakamura; Jennifer M Finefield; Hideharu Umaoka; Takashi Nakahara; Robert M Williams; Sachiko Tsukamoto
Journal:  Tetrahedron Lett       Date:  2011-12-21       Impact factor: 2.415

2.  Notoamide E: Biosynthetic incorporation into notoamides C and D in cultures of Aspergillus versicolor NRRL 35600.

Authors:  Jennifer M Finefield; Thomas J Greshock; David H Sherman; Sachiko Tsukamoto; Robert M Williams
Journal:  Tetrahedron Lett       Date:  2011-04-20       Impact factor: 2.415

3.  Lessons and revelations from biomimetic syntheses.

Authors:  Mina Razzak; Jef K De Brabander
Journal:  Nat Chem Biol       Date:  2011-11-15       Impact factor: 15.040

4.  Genome-based characterization of two prenylation steps in the assembly of the stephacidin and notoamide anticancer agents in a marine-derived Aspergillus sp.

Authors:  Yousong Ding; Jeffrey R de Wet; James Cavalcoli; Shengying Li; Thomas J Greshock; Kenneth A Miller; Jennifer M Finefield; James D Sunderhaus; Timothy J McAfoos; Sachiko Tsukamoto; Robert M Williams; David H Sherman
Journal:  J Am Chem Soc       Date:  2010-09-15       Impact factor: 15.419

Review 5.  Enantiomeric natural products: occurrence and biogenesis.

Authors:  Jennifer M Finefield; David H Sherman; Martin Kreitman; Robert M Williams
Journal:  Angew Chem Int Ed Engl       Date:  2012-05-03       Impact factor: 15.336

6.  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

7.  Studies on the Biosynthesis of the Stephacidin and Notoamide Natural Products: A Stereochemical and Genetic Conundrum.

Authors:  James D Sunderhaus; David H Sherman; Robert M Williams
Journal:  Isr J Chem       Date:  2011-04       Impact factor: 3.333

8.  Bioconversion of 6-epi-Notoamide T Produces Metabolites of Unprecedented Structures in a Marine-derived Aspergillus sp.

Authors:  Hikaru Kato; Takashi Nakahara; Michitaka Yamaguchi; Ippei Kagiyama; Jennifer M Finefield; James D Sunderhaus; David H Sherman; Robert M Williams; Sachiko Tsukamoto
Journal:  Tetrahedron Lett       Date:  2015-01-01       Impact factor: 2.415

9.  Flavin-Dependent Monooxygenases NotI and NotI' Mediate Spiro-Oxindole Formation in Biosynthesis of the Notoamides.

Authors:  Amy E Fraley; Hong T Tran; Samantha P Kelly; Sean A Newmister; Ashootosh Tripathi; Hikaru Kato; Sachiko Tsukamoto; Lei Du; Shengying Li; Robert M Williams; David H Sherman
Journal:  Chembiochem       Date:  2020-05-14       Impact factor: 3.164

10.  Synthesis and bioconversions of notoamide T: a biosynthetic precursor to stephacidin A and notoamide B.

Authors:  James D Sunderhaus; Timothy J McAfoos; Jennifer M Finefield; Hikaru Kato; Shengying Li; Sachiko Tsukamoto; David H Sherman; Robert M Williams
Journal:  Org Lett       Date:  2012-12-18       Impact factor: 6.005
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