Literature DB >> 22566715

Thielavin B methyl ester: a cytotoxic benzoate trimer from an unidentified fungus (MSX 55526) from the Order Sordariales.

Sloan Ayers1, Brandie M Ehrmann, Audrey F Adcock, David J Kroll, Mansukh C Wani, Cedric J Pearce, Nicholas H Oberlies.   

Abstract

As part of our ongoing investigation of filamentous fungi for anticancer leads, an active fungal extract was identified from the Mycosynthetix library (MSX 55526; from the Order Sordariales). Bioactivity-directed fractionation yielded the known ergosterol peroxide (2) and 5α,8α-epidioxyergosta-6,9(11),22-trien-3β-ol(3), and a new benzoate trimer, termed thielavin B methyl ester (1). The structure elucidation of 1 was facilitated by the use of HRMS coupled to an APPI (atmospheric pressure photoionization) source. Compound 1 proved to be moderately active against a panel of three cancer cell lines.

Entities:  

Year:  2011        PMID: 22566715      PMCID: PMC3343773          DOI: 10.1016/j.tetlet.2011.08.125

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


  16 in total

1.  Effect of eluent on the ionization efficiency of flavonoids by ion spray, atmospheric pressure chemical ionization, and atmospheric pressure photoionization mass spectrometry.

Authors:  J P Rauha; H Vuorela; R Kostiainen
Journal:  J Mass Spectrom       Date:  2001-12       Impact factor: 1.982

2.  Atmospheric pressure photoionization proton transfer for complex organic mixtures investigated by fourier transform ion cyclotron resonance mass spectrometry.

Authors:  Jeremiah M Purcell; Christopher L Hendrickson; Ryan P Rodgers; Alan G Marshall
Journal:  J Am Soc Mass Spectrom       Date:  2007-08-03       Impact factor: 3.109

3.  The structures of thielavins A, B and C. Prostaglandin synthetase inhibitors from fungi.

Authors:  N Kitahara; H Haruyama; T Hata; S Takahashi
Journal:  J Antibiot (Tokyo)       Date:  1983-05       Impact factor: 2.649

4.  Atmospheric pressure photoionization mass spectrometry. Ionization mechanism and the effect of solvent on the ionization of naphthalenes.

Authors:  Tiina J Kauppila; Tiia Kuuranne; Eduardo C Meurer; Marcos N Eberlin; Tapio Kotiaho; Risto Kostiainen
Journal:  Anal Chem       Date:  2002-11-01       Impact factor: 6.986

5.  Atmospheric pressure photoionization: an ionization method for liquid chromatography-mass spectrometry

Authors: 
Journal:  Anal Chem       Date:  2000-08-01       Impact factor: 6.986

Review 6.  Fingolimod (FTY720): a recently approved multiple sclerosis drug based on a fungal secondary metabolite.

Authors:  Cherilyn R Strader; Cedric J Pearce; Nicholas H Oberlies
Journal:  J Nat Prod       Date:  2011-04-01       Impact factor: 4.050

7.  Atmospheric pressure photoionization fourier transform ion cyclotron resonance mass spectrometry for complex mixture analysis.

Authors:  Jeremiah M Purcell; Christopher L Hendrickson; Ryan P Rodgers; Alan G Marshall
Journal:  Anal Chem       Date:  2006-08-15       Impact factor: 6.986

8.  Speciation of nitrogen containing aromatics by atmospheric pressure photoionization or electrospray ionization fourier transform ion cyclotron resonance mass spectrometry.

Authors:  Jeremiah M Purcell; Ryan P Rodgers; Christopher L Hendrickson; Alan G Marshall
Journal:  J Am Soc Mass Spectrom       Date:  2007-04-10       Impact factor: 3.109

9.  Thielavins as glucose-6-phosphatase (G6Pase) inhibitors: producing strain, fermentation, isolation, structural elucidation and biological activities.

Authors:  Shinichi Sakemi; Hideo Hirai; Toshio Ichiba; Taisuke Inagaki; Yoshinao Kato; Nakao Kojima; Hiroyuki Nishida; Janice C Parker; Toshiyuki Saito; Hiroko Tonai-Kachi; Maria A VanVolkenburg; Nobuji Yoshikawa; Yasuhiro Kojima
Journal:  J Antibiot (Tokyo)       Date:  2002-11       Impact factor: 2.649

10.  Resorcylic acid lactones with cytotoxic and NF-κB inhibitory activities and their structure-activity relationships.

Authors:  Sloan Ayers; Tyler N Graf; Audrey F Adcock; David J Kroll; Susan Matthew; Esperanza J Carcache de Blanco; Qi Shen; Steven M Swanson; Mansukh C Wani; Cedric J Pearce; Nicholas H Oberlies
Journal:  J Nat Prod       Date:  2011-04-22       Impact factor: 4.803

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  8 in total

1.  Chemoinformatic expedition of the chemical space of fungal products.

Authors:  Mariana González-Medina; Fernando D Prieto-Martínez; J Jesús Naveja; Oscar Méndez-Lucio; Tamam El-Elimat; Cedric J Pearce; Nicholas H Oberlies; Mario Figueroa; José L Medina-Franco
Journal:  Future Med Chem       Date:  2016-08-03       Impact factor: 3.808

Review 2.  Discovery of Anticancer Agents of Diverse Natural Origin.

Authors:  A Douglas Kinghorn; Esperanza J Carcache DE Blanco; David M Lucas; H Liva Rakotondraibe; Jimmy Orjala; D Doel Soejarto; Nicholas H Oberlies; Cedric J Pearce; Mansukh C Wani; Brent R Stockwell; Joanna E Burdette; Steven M Swanson; James R Fuchs; Mitchell A Phelps; Lihui Xu; Xiaoli Zhang; Young Yongchun Shen
Journal:  Anticancer Res       Date:  2016-11       Impact factor: 2.480

3.  Chemical Diversity of Metabolites from Fungi, Cyanobacteria, and Plants Relative to FDA-Approved Anticancer Agents.

Authors:  Tamam El-Elimat; Xiaoli Zhang; David Jarjoura; Franklin J Moy; Jimmy Orjala; A Douglas Kinghorn; Cedric J Pearce; Nicholas H Oberlies
Journal:  ACS Med Chem Lett       Date:  2012-07-12       Impact factor: 4.345

4.  Biosynthetically Distinct Cytotoxic Polyketides from Setophoma terrestris.

Authors:  Tamam El-Elimat; Mario Figueroa; Huzefa A Raja; Tyler N Graf; Steven M Swanson; Joseph O Falkinham; Mansukh C Wani; Cedric J Pearce; Nicholas H Oberlies
Journal:  European J Org Chem       Date:  2015-01-01

5.  Prealamethicin F50 and related peptaibols from Trichoderma arundinaceum: Validation of their authenticity via in situ chemical analysis.

Authors:  José Rivera-Chávez; Huzefa A Raja; Tyler N Graf; Jacklyn M Gallagher; Prashant Metri; Ding Xue; Cedric J Pearce; Nicholas H Oberlies
Journal:  RSC Adv       Date:  2017-09-25       Impact factor: 3.361

6.  Peptaibols from two unidentified fungi of the order Hypocreales with cytotoxic, antibiotic, and anthelmintic activities.

Authors:  Sloan Ayers; Brandie M Ehrmann; Audrey F Adcock; David J Kroll; Esperanza J Carcache de Blanco; Qi Shen; Steven M Swanson; Joseph O Falkinham; Mansukh C Wani; Sheila M Mitchell; Cedric J Pearce; Nicholas H Oberlies
Journal:  J Pept Sci       Date:  2012-06-29       Impact factor: 1.905

7.  High-resolution MS, MS/MS, and UV database of fungal secondary metabolites as a dereplication protocol for bioactive natural products.

Authors:  Tamam El-Elimat; Mario Figueroa; Brandie M Ehrmann; Nadja B Cech; Cedric J Pearce; Nicholas H Oberlies
Journal:  J Nat Prod       Date:  2013-08-16       Impact factor: 4.050

8.  Biosynthesis of Fluorinated Peptaibols Using a Site-Directed Building Block Incorporation Approach.

Authors:  José Rivera-Chávez; Huzefa A Raja; Tyler N Graf; Joanna E Burdette; Cedric J Pearce; Nicholas H Oberlies
Journal:  J Nat Prod       Date:  2017-06-08       Impact factor: 4.050

  8 in total

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