Literature DB >> 24816491

Epidithiodioxopiperazines. occurrence, synthesis and biogenesis.

Timothy R Welch1, Robert M Williams.   

Abstract

Epidithiodioxopiperazine alkaloids possess an astonishing array of molecular architecture and generally exhibit potent biological n class="Chemical">activity. Nearly twenty distinct families have been isolated and characterized since the seminal discovery of gliotoxin in 1936. Numerous biosynthetic investigations offer a glimpse at the relative ease with which Nature is able to assemble this class of molecules, while providing synthetic chemists inspiration for the development of more efficient syntheses. Herein, we discuss the isolation and characterization, proposed fungal biogeneses, and total syntheses of epidithiodioxopiperazines.

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Year:  2014        PMID: 24816491      PMCID: PMC4162872          DOI: 10.1039/c3np70097f

Source DB:  PubMed          Journal:  Nat Prod Rep        ISSN: 0265-0568            Impact factor:   13.423


  87 in total

1.  Epicorazine C, an antimicrobial metabolite from Stereum hirsutum HKI 0195.

Authors:  P Kleinwächter; H M Dahse; U Luhmann; B Schlegel; K Dornberger
Journal:  J Antibiot (Tokyo)       Date:  2001-06       Impact factor: 2.649

2.  A hepatotoxin from Sporidesmium bakeri capable of producing facial eczema diseases in sheep.

Authors:  R H THORNTON; J C PERCIVAL
Journal:  Nature       Date:  1959-01-03       Impact factor: 49.962

3.  Studies on fungal products. IX. Dethiosecoemestrin, a new metabolite related to emestrin, from Emericella striata.

Authors:  H Seya; K Nozawa; S Udagawa; S Nakajima; K Kawai
Journal:  Chem Pharm Bull (Tokyo)       Date:  1986-06       Impact factor: 1.645

4.  Mechanism of action of gliotoxin: elimination of activity by sulfhydryl compounds.

Authors:  P W Trown; J A Bilello
Journal:  Antimicrob Agents Chemother       Date:  1972-10       Impact factor: 5.191

5.  Bionectins A-C, epidithiodioxopiperazines with anti-MRSA activity, from Bionectra byssicola F120.

Authors:  Chang-Ji Zheng; Chang-Jin Kim; Kyung Sook Bae; Young-Ho Kim; Won-Gon Kim
Journal:  J Nat Prod       Date:  2006-12       Impact factor: 4.050

6.  Total synthesis of (+)-chaetocin and its analogues: their histone methyltransferase G9a inhibitory activity.

Authors:  Eriko Iwasa; Yoshitaka Hamashima; Shinya Fujishiro; Eisuke Higuchi; Akihiro Ito; Minoru Yoshida; Mikiko Sodeoka
Journal:  J Am Chem Soc       Date:  2010-03-31       Impact factor: 15.419

7.  Enantioselective total synthesis of (-)-acetylaranotin, a dihydrooxepine epidithiodiketopiperazine.

Authors:  Julian A Codelli; Angela L A Puchlopek; Sarah E Reisman
Journal:  J Am Chem Soc       Date:  2011-10-28       Impact factor: 15.419

8.  Biosynthesis of gliotoxin and mycelianamide.

Authors:  J C Macdonald; G P Slater
Journal:  Can J Biochem       Date:  1975-04

9.  Total synthesis of (+)-11,11'-dideoxyverticillin A.

Authors:  Justin Kim; James A Ashenhurst; Mohammad Movassaghi
Journal:  Science       Date:  2009-04-10       Impact factor: 47.728

10.  Cytotoxic metabolites from the antarctic psychrophilic fungus Oidiodendron truncatum.

Authors:  Liyuan Li; Dehai Li; Yepeng Luan; Qianqun Gu; Tianjiao Zhu
Journal:  J Nat Prod       Date:  2012-05-14       Impact factor: 4.050

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  25 in total

1.  Interplay between Gliotoxin Resistance, Secretion, and the Methyl/Methionine Cycle in Aspergillus fumigatus.

Authors:  Rebecca A Owens; Grainne O'Keeffe; Elizabeth B Smith; Stephen K Dolan; Stephen Hammel; Kevin J Sheridan; David A Fitzpatrick; Thomas M Keane; Gary W Jones; Sean Doyle
Journal:  Eukaryot Cell       Date:  2015-07-06

2.  Epipolythiodiketopiperazine and trichothecene derivatives from the NaI-containing fermentation of marine-derived Trichoderma cf. brevicompactum.

Authors:  Hiroyuki Yamazaki; Ohgi Takahashi; Ryota Kirikoshi; Akiho Yagi; Teruki Ogasawara; Yuki Bunya; Henki Rotinsulu; Ryuji Uchida; Michio Namikoshi
Journal:  J Antibiot (Tokyo)       Date:  2020-05-19       Impact factor: 2.649

3.  n→π* Interactions Modulate the Disulfide Reduction Potential of Epidithiodiketopiperazines.

Authors:  Henry R Kilgore; Chase R Olsson; Kyan A D'Angelo; Mohammad Movassaghi; Ronald T Raines
Journal:  J Am Chem Soc       Date:  2020-08-21       Impact factor: 15.419

4.  A Modular Construction of Epidithiodiketopiperazines.

Authors:  Thomas N Snaddon; Toya D Scaggs; Colin M Pearson; James W B Fyfe
Journal:  Org Lett       Date:  2019-06-11       Impact factor: 6.005

5.  A microbial metabolite synergizes with endogenous serotonin to trigger C. elegans reproductive behavior.

Authors:  Yen-Chih Chen; Mohammad R Seyedsayamdost; Niels Ringstad
Journal:  Proc Natl Acad Sci U S A       Date:  2020-11-16       Impact factor: 11.205

Review 6.  Mini-Review: Ergothioneine and Ovothiol Biosyntheses, an Unprecedented Trans-Sulfur Strategy in Natural Product Biosynthesis.

Authors:  Nathchar Naowarojna; Ronghai Cheng; Li Chen; Melissa Quill; Meiling Xu; Changming Zhao; Pinghua Liu
Journal:  Biochemistry       Date:  2018-04-06       Impact factor: 3.162

7.  The Epipolythiodiketopiperazine Gene Cluster in Claviceps purpurea: Dysfunctional Cytochrome P450 Enzyme Prevents Formation of the Previously Unknown Clapurines.

Authors:  Julian Dopstadt; Lisa Neubauer; Paul Tudzynski; Hans-Ulrich Humpf
Journal:  PLoS One       Date:  2016-07-08       Impact factor: 3.240

Review 8.  The Oxepane Motif in Marine Drugs.

Authors:  Héctor Barbero; Carlos Díez-Poza; Asunción Barbero
Journal:  Mar Drugs       Date:  2017-11-15       Impact factor: 5.118

9.  Fungal Epithiodiketopiperazines Carrying α,β-Polysulfide Bridges from Penicillium steckii YE, and Their Chemical Interconversion.

Authors:  Guangde Jiang; Peilan Zhang; Ranjala Ratnayake; Guang Yang; Yi Zhang; Ran Zuo; Magan Powell; José C Huguet-Tapia; Khalil A Abboud; Long H Dang; Max Teplitski; Valerie Paul; Rui Xiao; K H Ahammad; Uz Zaman; Zhenquan Hu; Shugeng Cao; Hendrik Luesch; Yousong Ding
Journal:  Chembiochem       Date:  2020-09-30       Impact factor: 3.164

10.  Inhibitory Effects of Epipolythiodioxopiperazine Fungal Metabolites on Isocitrate Lyase in the Glyoxylate Cycle of Candida albicans.

Authors:  Ji-Yeon Hwang; Beomkoo Chung; Oh-Seok Kwon; Sung Chul Park; Eunji Cho; Dong-Chan Oh; Jongheon Shin; Ki-Bong Oh
Journal:  Mar Drugs       Date:  2021-05-22       Impact factor: 5.118

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