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Literature DB >> 22140279

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

Jennifer M Finefield¹, Thomas J Greshock, David H Sherman, Sachiko Tsukamoto, Robert M Williams.

Abstract

Notoamide E, a short-lived secondary metabolite, has been proposed as a biosynthetic intermediate to several advanced metabolites isolated from Aspergillus versicolor. In order to verify the role of this indole alkaloid along the biosynthetic pathway, synthetic doubly (13)C-labeled notoamide E was fed to Aspergillus versicolor. Analysis of the metabolites showed significant incorporation of notoamide E into the natural products notoamides C and D.

Entities: Chemical Species

Year: 2011 PMID： 22140279 PMCID： PMC3226721 DOI： 10.1016/j.tetlet.2011.02.078

Source DB: PubMed Journal: Tetrahedron Lett ISSN： 0040-4039 Impact factor: 2.415

17 in total

1. A concise total synthesis of the notoamides C and D.

Authors: Alan W Grubbs; Gerald D Artman; Sachiko Tsukamoto; Robert M Williams
Journal: Angew Chem Int Ed Engl Date: 2007 Impact factor: 15.336

2. A concise, biomimetic total synthesis of stephacidin A and notoamide B.

Authors: Thomas J Greshock; Alan W Grubbs; Sachiko Tsukamoto; Robert M Williams
Journal: Angew Chem Int Ed Engl Date: 2007 Impact factor: 15.336

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. 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

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Authors: R M Banks; S E Blanchflower; J R Everett; B R Manger; C Reading
Journal: J Antibiot (Tokyo) Date: 1997-10 Impact factor: 2.649

Review 7. Total synthesis and biosynthesis of the paraherquamides: an intriguing story of the biological Diels-Alder construction.

Authors: Robert Michael Williams
Journal: Chem Pharm Bull (Tokyo) Date: 2002-06 Impact factor: 1.645

8. 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

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 antipodal (-)-versicolamide B and notoamides L-N from a marine-derived Aspergillus sp.

Authors: Sachiko Tsukamoto; Tetsuro Kawabata; Hikaru Kato; Thomas J Greshock; Hiroshi Hirota; Tomihisa Ohta; Robert M Williams
Journal: Org Lett Date: 2009-03-19 Impact factor: 6.005

8 in total

Review 1. 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

Review 2. Marine-derived Aspergillus species as a source of bioactive secondary metabolites.

Authors: Yoon Mi Lee; Min Jeong Kim; Huayue Li; Ping Zhang; Baoquan Bao; Ka Jeong Lee; Jee H Jung
Journal: Mar Biotechnol (NY) Date: 2013-05-25 Impact factor: 3.619

3. Studies on the biosynthesis of the notoamides: synthesis of an isotopomer of 6-hydroxydeoxybrevianamide E and biosynthetic incorporation into notoamide J.

Authors: Jennifer M Finefield; David H Sherman; Sachiko Tsukamoto; Robert M Williams
Journal: J Org Chem Date: 2011-06-28 Impact factor: 4.354

4. 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

Review 5. 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 6. 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

7. Shornephine A: structure, chemical stability, and P-glycoprotein inhibitory properties of a rare diketomorpholine from an Australian marine-derived Aspergillus sp.

Authors: Zeinab G Khalil; Xiao-cong Huang; Ritesh Raju; Andrew M Piggott; Robert J Capon
Journal: J Org Chem Date: 2014-09-02 Impact factor: 4.354

Review 8. Structural Diversity and Biological Activities of the Cyclodipeptides from Fungi.

Authors: Xiaohan Wang; Yuying Li; Xuping Zhang; Daowan Lai; Ligang Zhou
Journal: Molecules Date: 2017-11-23 Impact factor: 4.411

8 in total