Literature DB >> 17125221

A chemical study of cyclic depsipeptides produced by a sponge-derived fungus.

Taro Amagata1, Brandon I Morinaka, Akiko Amagata, Karen Tenney, Frederick A Valeriote, Emil Lobkovsky, Jon Clardy, Phillip Crews.   

Abstract

Two novel cyclic depsipeptides, guangomides A (1) and B (2), together with a new destruxin derivative (3) were isolated from the cytotoxic extract obtained from the saltwater culture of an unidentifiable sponge-derived fungus. The new structures were elucidated on the basis of analysis of extensive 1D and 2D NMR data sets, and the absolute configurations of 2S, 9S, 13S, 19S, 24R, 28R of 1 were determined on the basis of the combined X-ray and Marfey's method structure analysis. Identical absolute configurations were assumed for 2. The cytotoxicity of the extract was found to be due to brefeldin A, while 1 and 2 showed weak antibacterial activity against Staphylococcus epidermidis and Enterococcus durans.

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Year:  2006        PMID: 17125221      PMCID: PMC3014288          DOI: 10.1021/np060178k

Source DB:  PubMed          Journal:  J Nat Prod        ISSN: 0163-3864            Impact factor:   4.050


  18 in total

1.  N-Methylsansalvamide, a cytotoxic cyclic depsipeptide from a marine fungus of the genus fusarium.

Authors:  M Cueto; P R Jensen; W Fenical
Journal:  Phytochemistry       Date:  2000-10       Impact factor: 4.072

2.  Isolation of dolastatin 10 from the marine cyanobacterium Symploca species VP642 and total stereochemistry and biological evaluation of its analogue symplostatin 1.

Authors:  H Luesch; R E Moore; V J Paul; S L Mooberry; T H Corbett
Journal:  J Nat Prod       Date:  2001-07       Impact factor: 4.050

3.  Chondramides, novel cyclodepsipeptides from myxobacteria, influence cell development and induce actin filament polymerization in the green alga Micrasterias.

Authors:  A Holzinger; U Lütz-Meindl
Journal:  Cell Motil Cytoskeleton       Date:  2001-02

4.  Roseocardin, a novel cardiotonic cyclodepsipeptide from Trichothecium roseum TT103.

Authors:  A Tsunoo; M Kamijo; N Taketomo; Y Sato; K Ajisaka
Journal:  J Antibiot (Tokyo)       Date:  1997-12       Impact factor: 2.649

5.  Highly N-methylated linear peptides produced by an atypical sponge-derived Acremonium sp.

Authors:  Claudia M Boot; Karen Tenney; Frederick A Valeriote; Phillip Crews
Journal:  J Nat Prod       Date:  2006-01       Impact factor: 4.050

6.  Probing host-selective phytotoxicity: synthesis of destruxin B and several natural analogues.

Authors:  D E Ward; Y Gai; R Lazny; M S Pedras
Journal:  J Org Chem       Date:  2001-11-16       Impact factor: 4.354

7.  The chondramides: cytostatic agents from myxobacteria acting on the actin cytoskeleton.

Authors:  F Sasse; B Kunze; T M Gronewold; H Reichenbach
Journal:  J Natl Cancer Inst       Date:  1998-10-21       Impact factor: 13.506

8.  (-)-Doliculide, a new macrocyclic depsipeptide enhancer of actin assembly.

Authors:  Ruoli Bai; David G Covell; Chunfeng Liu; Arun K Ghosh; Ernest Hamel
Journal:  J Biol Chem       Date:  2002-06-20       Impact factor: 5.157

9.  Stereochemistry of kahalalide F.

Authors:  Isabelle Bonnard; Ignacio Manzanares; Kenneth L Rinehart
Journal:  J Nat Prod       Date:  2003-11       Impact factor: 4.050

10.  A further study of the cytotoxic constituents of a milnamide-producing sponge.

Authors:  Rachel N Sonnenschein; Jarrett J Farias; Karen Tenney; Susan L Mooberry; Emil Lobkovsky; Jon Clardy; Phillip Crews
Journal:  Org Lett       Date:  2004-03-04       Impact factor: 6.005

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  14 in total

1.  Phylogenetically diverse cultivable fungal community and polyketide synthase (PKS), non-ribosomal peptide synthase (NRPS) genes associated with the South China Sea sponges.

Authors:  Kang Zhou; Xia Zhang; Fengli Zhang; Zhiyong Li
Journal:  Microb Ecol       Date:  2011-04-26       Impact factor: 4.552

2.  Unraveling the Numerous Biosynthetic Products of the Marine Sediment-Derived Fungus, Aspergillus insulicola.

Authors:  Q X Wu; X J Jin; M Draskovic; M S Crews; K Tenney; F A Valeriote; X J Yao; P Crews
Journal:  Phytochem Lett       Date:  2012-03-01       Impact factor: 1.679

Review 3.  Marine natural product peptides with therapeutic potential: Chemistry, biosynthesis, and pharmacology.

Authors:  Vedanjali Gogineni; Mark T Hamann
Journal:  Biochim Biophys Acta Gen Subj       Date:  2017-08-24       Impact factor: 3.770

4.  Azonazine, a novel dipeptide from a Hawaiian marine sediment-derived fungus, Aspergillus insulicola.

Authors:  Quan-Xiang Wu; Mitchell S Crews; Marija Draskovic; Johann Sohn; Tyler A Johnson; Karen Tenney; Frederick A Valeriote; Xiao-Jun Yao; Leonard F Bjeldanes; Phillip Crews
Journal:  Org Lett       Date:  2010-10-15       Impact factor: 6.005

5.  Recovery and phylogenetic diversity of culturable fungi associated with marine sponges Clathrina luteoculcitella and Holoxea sp. in the South China Sea.

Authors:  Bo Ding; Ying Yin; Fengli Zhang; Zhiyong Li
Journal:  Mar Biotechnol (NY)       Date:  2010-11-19       Impact factor: 3.619

6.  Cyclodepsipeptides, sesquiterpenoids, and other cytotoxic metabolites from the filamentous fungus Trichothecium sp. (MSX 51320).

Authors:  Arlene A Sy-Cordero; Tyler N Graf; Audrey F Adcock; David J Kroll; Qi Shen; Steven M Swanson; Mansukh C Wani; Cedric J Pearce; Nicholas H Oberlies
Journal:  J Nat Prod       Date:  2011-10-06       Impact factor: 4.050

Review 7.  Marine Cyclic Peptides: Antimicrobial Activity and Synthetic Strategies.

Authors:  Ricardo Ribeiro; Eugénia Pinto; Carla Fernandes; Emília Sousa
Journal:  Mar Drugs       Date:  2022-06-15       Impact factor: 6.085

8.  Anti-inflammatory effects of peptides from a marine algicolous fungus Acremonium sp. NTU492 in BV-2 microglial cells.

Authors:  George Hsiao; Shih-Wei Wang; Yin-Ru Chiang; Wei-Chiung Chi; Yueh-Hsiung Kuo; Do Anh Phong; Chia-Yu Chen; Tzong-Huei Lee
Journal:  J Food Drug Anal       Date:  2020-06-15       Impact factor: 6.157

Review 9.  Marine pharmacology in 2005-6: Marine compounds with anthelmintic, antibacterial, anticoagulant, antifungal, anti-inflammatory, antimalarial, antiprotozoal, antituberculosis, and antiviral activities; affecting the cardiovascular, immune and nervous systems, and other miscellaneous mechanisms of action.

Authors:  Alejandro M S Mayer; Abimael D Rodríguez; Roberto G S Berlinck; Mark T Hamann
Journal:  Biochim Biophys Acta       Date:  2009-03-19

Review 10.  Nonribosomal Peptides from Marine Microbes and Their Antimicrobial and Anticancer Potential.

Authors:  Shivankar Agrawal; Debabrata Acharya; Alok Adholeya; Colin J Barrow; Sunil K Deshmukh
Journal:  Front Pharmacol       Date:  2017-11-21       Impact factor: 5.810

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