Literature DB >> 26115570

Verruculides A and B, two new protein tyrosine phosphatase 1B inhibitors from an Indonesian ascidian-derived Penicillium verruculosum.

Hiroyuki Yamazaki1, Wataru Nakayama2, Ohgi Takahashi2, Ryota Kirikoshi2, Yuta Izumikawa2, Kohei Iwasaki2, Kengo Toraiwa2, Kazuyo Ukai2, Henki Rotinsulu3, Defny S Wewengkang4, Deiske A Sumilat5, Remy E P Mangindaan5, Michio Namikoshi2.   

Abstract

Two new merosesquiterpenes, verruculides A (1) and B (2), were isolated from a culture broth of the Indonesian ascidian-derived Penicillium verruculosum TPU1311, together with three known congeners, chrodrimanins A (3), B (4), and H (5). The structures of 1 and 2 were assigned on the basis of their spectroscopic data (1D and 2D NMR, HRMS, UV, CD, and IR). Compound 2 had a linear sesquiterpene moiety and was considered to be the derivative of the biosynthetic precursor for 1 and 3-5. Compounds 1, 3, and 5 inhibited the activity of protein tyrosine phosphatase 1B (PTP1B) with IC50 values of 8.4, 8.5, and 14.9 μM, respectively. Compound 2 showed 40% inhibition at 23.1 μM, while 4 was not active at 20.7 μM.
Copyright © 2015 Elsevier Ltd. All rights reserved.

Entities:  

Keywords:  Ascidian-derived fungus; Inhibitor; Penicillium verruculosum; Protein tyrosine phosphatase 1B; Verruculide

Mesh:

Substances:

Year:  2015        PMID: 26115570     DOI: 10.1016/j.bmcl.2015.06.026

Source DB:  PubMed          Journal:  Bioorg Med Chem Lett        ISSN: 0960-894X            Impact factor:   2.823


  14 in total

Review 1.  Peculiarities of meroterpenoids and their bioproduction.

Authors:  Jianying Han; Lan Jiang; Lixin Zhang; Ronald J Quinn; Xueting Liu; Yunjiang Feng
Journal:  Appl Microbiol Biotechnol       Date:  2021-05-03       Impact factor: 4.813

2.  Biphenyl ether derivatives with protein tyrosine phosphatase 1B inhibitory activity from the freshwater fungus Phoma sp.

Authors:  Deiske A Sumilat; Hiroyuki Yamazaki; Syu-Ichi Kanno; Ryo Saito; Yuta Watanabe; Michio Namikoshi
Journal:  J Antibiot (Tokyo)       Date:  2017-01-11       Impact factor: 2.649

3.  Cladosporamide A, a new protein tyrosine phosphatase 1B inhibitor, produced by an Indonesian marine sponge-derived Cladosporium sp.

Authors:  Henki Rotinsulu; Hiroyuki Yamazaki; Shino Sugai; Natsuki Iwakura; Defny S Wewengkang; Deiske A Sumilat; Michio Namikoshi
Journal:  J Nat Med       Date:  2018-03-05       Impact factor: 2.343

4.  An epigenetic modifier induces production of (10'S)-verruculide B, an inhibitor of protein tyrosine phosphatases by Phoma sp. nov. LG0217, a fungal endophyte of Parkinsonia microphylla.

Authors:  Juliana R Gubiani; E M Kithsiri Wijeratne; Taoda Shi; Angela R Araujo; A Elizabeth Arnold; Eli Chapman; A A Leslie Gunatilaka
Journal:  Bioorg Med Chem       Date:  2017-02-03       Impact factor: 3.641

5.  Characterization of a bioactive meroterpenoid isolated from the marine-derived fungus Talaromyces sp.

Authors:  Xuan Hong; Xiaoqing Guan; Qiliang Lai; Dehua Yu; Zhongwei Chen; Xiaoteng Fu; Beibei Zhang; Changkun Chen; Zongze Shao; Jinmei Xia; Jiang-Jiang Qin; Weiyi Wang
Journal:  Appl Microbiol Biotechnol       Date:  2022-04-13       Impact factor: 4.813

Review 6.  Bioactive Compounds Produced by Strains of Penicillium and Talaromyces of Marine Origin.

Authors:  Rosario Nicoletti; Antonio Trincone
Journal:  Mar Drugs       Date:  2016-02-18       Impact factor: 5.118

Review 7.  A Review of Terpenes from Marine-Derived Fungi: 2015-2019.

Authors:  Minghua Jiang; Zhenger Wu; Heng Guo; Lan Liu; Senhua Chen
Journal:  Mar Drugs       Date:  2020-06-18       Impact factor: 5.118

8.  Exploiting the Potential of Meroterpenoid Cyclases to Expand the Chemical Space of Fungal Meroterpenoids.

Authors:  Takaaki Mitsuhashi; Lena Barra; Zachary Powers; Volga Kojasoy; Andrea Cheng; Feng Yang; Yoshimasa Taniguchi; Takashi Kikuchi; Makoto Fujita; Dean J Tantillo; John A Porco; Ikuro Abe
Journal:  Angew Chem Int Ed Engl       Date:  2020-10-22       Impact factor: 15.336

Review 9.  Marine Natural Products from Tunicates and Their Associated Microbes.

Authors:  Chatragadda Ramesh; Bhushan Rao Tulasi; Mohanraju Raju; Narsinh Thakur; Laurent Dufossé
Journal:  Mar Drugs       Date:  2021-05-26       Impact factor: 5.118

Review 10.  Ascidian Toxins with Potential for Drug Development.

Authors:  Dianne J Watters
Journal:  Mar Drugs       Date:  2018-05-13       Impact factor: 5.118

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