Literature DB >> 12465964

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

Jingfang Qian-Cutrone1, Stella Huang, Yue-Zhong Shu, Dolatrai Vyas, Craig Fairchild, Ana Menendez, Kimberly Krampitz, Richard Dalterio, Steven E Klohr, Qi Gao.   

Abstract

Two novel antitumor alkaloids, Stephacidin A and B, were isolated from the solid fermentation of Aspergillus ochraceus WC76466. Both alkaloids exhibit in vitro cytotoxicity against a number of human tumor cell lines; however, stephacidin B demonstrated more potent and selective antitumor activities, especially against prostate testeosterone-dependent LNCaP cells with IC50 value of 60 nM. The structures of stephacidin A and B were established on the basis of the NMR data and X-ray crystallography. With 15 rings and 9 chiral centers, stephacidin B represents one of the most structurally complex and novel alkaloids occurring in nature.

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Year:  2002        PMID: 12465964     DOI: 10.1021/ja028538n

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


  63 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.  Waikialoid A suppresses hyphal morphogenesis and inhibits biofilm development in pathogenic Candida albicans.

Authors:  Xiaoru Wang; Jianlan You; Jarrod B King; Douglas R Powell; Robert H Cichewicz
Journal:  J Nat Prod       Date:  2012-03-08       Impact factor: 4.050

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

5.  Studies Towards Paraherquamides E & F and Related C-labeled Putative Biosynthetic Intermediates: Stereocontrolled Synthesis of the α-Alkyl-β-Methylproline Ring System.

Authors:  Konrad Sommer; Robert M Williams
Journal:  Tetrahedron       Date:  2008-07-21       Impact factor: 2.457

6.  Evidence for the rapid conversion of stephacidin B into the electrophilic monomer avrainvillamide in cell culture.

Authors:  Jeremy E Wulff; Seth B Herzon; Romain Siegrist; Andrew G Myers
Journal:  J Am Chem Soc       Date:  2007-03-31       Impact factor: 15.419

Review 7.  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

8.  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

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

Authors:  Sachiko Tsukamoto; Hikaru Kato; Thomas J Greshock; Hiroshi Hirota; Tomihisa Ohta; Robert M Williams
Journal:  J Am Chem Soc       Date:  2009-03-25       Impact factor: 15.419

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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