Literature DB >> 33746553

New analogs of pochonicine, a potent β-N-acetylglucosaminidase inhibitor from fungus Pochonia suchlasporia var. suchlasporia TAMA 87.

Yuhichi Mushiake1, Aya Tsuchida1, Asami Yamada1, Hiroshi Kanzaki1, Toru Okuda2, Teruhiko Nitoda1.   

Abstract

Three novel analogs of pochonicine (1) were isolated from a solid fermentation culture of the fungal strain Pochonia suchlasporia var. suchlasporia TAMA 87, and their structures were elucidated as 7-deoxypochonicine (2), 6-deoxypochonicine (3), and 6,7-dideoxypochonicine (4). These analogs were found to possess the same stereochemistry as pochonicine. Comparison of β-N-acetylglucosaminidase (GlcNAcase) inhibitory activity between these analogs and pochonicine suggested that the C-6 hydroxy group of pochonicine was essential to its potent GlcNAcase inhibitory activity and that the C-7 hydroxy group also contributed to the activity, but to a lesser extent than the C-6 hydroxy group. © Pesticide Science Society of Japan 2021. This is an open access article distributed under the Creative Commons Attribution-NonCommercial-NoDerivatives 4.0 International (CC BY-NC-ND 4.0) License (https://creativecommons.org/licenses/by-nc-nd/4.0/).

Entities:  

Keywords:  Pochonia suchlasporia; chitinolytic enzyme; fungi; pochonicine; solid state fermentation; β-N-acetylglucosaminidase inhibitor

Year:  2021        PMID: 33746553      PMCID: PMC7953029          DOI: 10.1584/jpestics.D20-086

Source DB:  PubMed          Journal:  J Pestic Sci        ISSN: 1348-589X            Impact factor:   2.529


  8 in total

1.  A potent insect chitinase inhibitor of fungal origin.

Authors:  Teruhiko Nitoda; Hirokazu Usuki; Hiroshi Kanzaki
Journal:  Z Naturforsch C J Biosci       Date:  2003 Nov-Dec

Review 2.  Developing inhibitors of glycan processing enzymes as tools for enabling glycobiology.

Authors:  Tracey M Gloster; David J Vocadlo
Journal:  Nat Chem Biol       Date:  2012-07-18       Impact factor: 15.040

3.  Pochonicine, a polyhydroxylated pyrrolizidine alkaloid from fungus Pochonia suchlasporia var. suchlasporia TAMA 87 as a potent beta-N-acetylglucosaminidase inhibitor.

Authors:  Hirokazu Usuki; Miho Toyo-oka; Hiroshi Kanzaki; Toru Okuda; Teruhiko Nitoda
Journal:  Bioorg Med Chem       Date:  2009-08-31       Impact factor: 3.641

4.  TMG-chitotriomycin as a probe for the prediction of substrate specificity of β-N-acetylhexosaminidases.

Authors:  Hiroto Shiota; Hiroshi Kanzaki; Tadashi Hatanaka; Teruhiko Nitoda
Journal:  Carbohydr Res       Date:  2013-04-27       Impact factor: 2.104

5.  TMG-chitotriomycin, an enzyme inhibitor specific for insect and fungal beta-N-acetylglucosaminidases, produced by actinomycete Streptomyces anulatus NBRC 13369.

Authors:  Hirokazu Usuki; Teruhiko Nitoda; Misato Ichikawa; Nahoko Yamaji; Takashi Iwashita; Hajime Komura; Hiroshi Kanzaki
Journal:  J Am Chem Soc       Date:  2008-02-29       Impact factor: 15.419

6.  Synthesis of eight stereoisomers of pochonicine: nanomolar inhibition of β-N-acetylhexosaminidases.

Authors:  Jian-She Zhu; Shinpei Nakagawa; Wei Chen; Isao Adachi; Yue-Mei Jia; Xiang-Guo Hu; George W J Fleet; Francis X Wilson; Teruhiko Nitoda; Graeme Horne; Renate van Well; Atsushi Kato; Chu-Yi Yu
Journal:  J Org Chem       Date:  2013-09-30       Impact factor: 4.354

7.  Phylogenetic analyses suggest multiple changes of substrate specificity within the glycosyl hydrolase 20 family.

Authors:  Jari Intra; Giulio Pavesi; David S Horner
Journal:  BMC Evol Biol       Date:  2008-07-22       Impact factor: 3.260

8.  A new asteltoxin analog with insecticidal activity from Pochonia suchlasporia TAMA 87.

Authors:  Syaefudin Suminto; Eri Takatsuji; Ayako Iguchi; Hiroshi Kanzaki; Toru Okuda; Teruhiko Nitoda
Journal:  J Pestic Sci       Date:  2020-05-20       Impact factor: 2.529

  8 in total
  1 in total

1.  New ways and new hopes for IGR development.

Authors:  Marek Jindra
Journal:  J Pestic Sci       Date:  2021-02-20       Impact factor: 2.529

  1 in total

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