Literature DB >> 21705224

Porpoisamides A and B, two novel epimeric cyclic depsipeptides from a Florida Keys collection of Lyngbya sp.

Theresa Meickle1, Sarath P Gunasekera, Yanxia Liu, Hendrik Luesch, Valerie J Paul.   

Abstract

NMR-guided fractionation of a non-polar extract of a Florida Keys collection of Lyngbya sp. resulted in the isolation of two novel epimeric cyclic depsipeptides, porpoisamides A (1) and B (2). The planar structures of these compounds were determined using NMR spectroscopic techniques. The absolute configurations of amino and hydroxy acid subunits were assigned by enantioselective HPLC analysis. These compounds showed weak cytotoxicity towards HCT-116 colorectal carcinoma and U2OS osteosarcoma cells. The porpoisamides are a unique pair of cyclic depsipeptides that are epimeric at C-2 of the β-amino acid, 3-amino-2-methyloctanoic acid. Published by Elsevier Ltd.

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Year:  2011        PMID: 21705224      PMCID: PMC3197893          DOI: 10.1016/j.bmc.2011.05.051

Source DB:  PubMed          Journal:  Bioorg Med Chem        ISSN: 0968-0896            Impact factor:   3.641


  12 in total

1.  Synthesis and gas chromatography/mass spectrometry analysis of stereoisomers of 2-hydroxy-3-methylpentanoic acid.

Authors:  O A Mamer
Journal:  Methods Enzymol       Date:  2000       Impact factor: 1.600

2.  Isolation and structure determination of obyanamide, a novel cytotoxic cyclic depsipeptide from the marine cyanobacterium Lyngbya confervoides.

Authors:  Philip G Williams; Wesley Y Yoshida; Richard E Moore; Valerie J Paul
Journal:  J Nat Prod       Date:  2002-01       Impact factor: 4.050

Review 3.  Bioactive natural products from marine cyanobacteria for drug discovery.

Authors:  Lik Tong Tan
Journal:  Phytochemistry       Date:  2007-03-02       Impact factor: 4.072

Review 4.  New peptides isolated from Lyngbya species: a review.

Authors:  Li Liu; Kathleen S Rein
Journal:  Mar Drugs       Date:  2010-06-09       Impact factor: 5.118

5.  Grassypeptolides A-C, cytotoxic bis-thiazoline containing marine cyclodepsipeptides.

Authors:  Jason C Kwan; Ranjala Ratnayake; Khalil A Abboud; Valerie J Paul; Hendrik Luesch
Journal:  J Org Chem       Date:  2010-11-04       Impact factor: 4.354

6.  Ulongamides A-F, new beta-amino acid-containing cyclodepsipeptides from Palauan collections of the marine cyanobacterium Lyngbya sp.

Authors:  Hendrik Luesch; Philip G Williams; Wesley Y Yoshida; Richard E Moore; Valerie J Paul
Journal:  J Nat Prod       Date:  2002-07       Impact factor: 4.050

7.  Ulongapeptin, a cytotoxic cyclic depsipeptide from a Palauan marine cyanobacterium Lyngbya sp.

Authors:  Philip G Williams; Wesley Y Yoshida; Michael K Quon; Richard E Moore; Valerie J Paul
Journal:  J Nat Prod       Date:  2003-05       Impact factor: 4.050

8.  Isolation of homodolastatin 16, a new cyclic depsipeptide from a Kenyan collection of Lyngbya majuscula.

Authors:  Michael T Davies-Coleman; Thomas M Dzeha; Christopher A Gray; Sonja Hess; Lewis K Pannell; Denver T Hendricks; Catherine E Arendse
Journal:  J Nat Prod       Date:  2003-05       Impact factor: 4.050

9.  The guineamides, novel cyclic depsipeptides from a Papua New Guinea collection of the marine cyanobacterium Lyngbya majuscula.

Authors:  Lik Tong Tan; Namthip Sitachitta; William H Gerwick
Journal:  J Nat Prod       Date:  2003-06       Impact factor: 4.050

10.  Total structure determination of grassypeptolide, a new marine cyanobacterial cytotoxin.

Authors:  Jason C Kwan; James R Rocca; Khalil A Abboud; Valerie J Paul; Hendrik Luesch
Journal:  Org Lett       Date:  2008-01-26       Impact factor: 6.005

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  2 in total

Review 1.  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

Review 2.  Marine Natural Peptides: Determination of Absolute Configuration Using Liquid Chromatography Methods and Evaluation of Bioactivities.

Authors:  Ye' Zaw Phyo; João Ribeiro; Carla Fernandes; Anake Kijjoa; Madalena M M Pinto
Journal:  Molecules       Date:  2018-01-31       Impact factor: 4.411

  2 in total

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