Literature DB >> 20701935

Two cytotoxic stereoisomers of malyngamide C, 8-epi-malyngamide C and 8-O-acetyl-8-epi-malyngamide C, from the marine cyanobacterium Lyngbya majuscula.

Harald Gross1, Kerry L McPhail, Douglas E Goeger, Frederick A Valeriote, William H Gerwick.   

Abstract

Two epimers of malyngamide C, 8-O-acetyl-8-epi-malyngamide C (1) and 8-epi-malyngamide C (3) have been isolated along with known compounds 6-O-acetylmalyngamide F (5), H (6), J (7) K (8), and characterized from a Grenada field collection of the marine cyanobacterium Lyngbya majuscula. The structures of these compounds were deduced by 1D and 2D NMR spectroscopic and mass spectral data interpretation. Absolute configurations were determined by a combination of CD-spectroscopy, chemical degradation and the variable temperature Mosher's method. Compounds 1-5, 7 and 8 displayed moderate cytotoxicity to NCI-H460 human lung tumor and neuro-2a cancer cell lines, with IC(50) values ranging between 0.5 and 20 microg/mL.
Copyright © 2010 Elsevier Ltd. All rights reserved.

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Year:  2010        PMID： 20701935      PMCID： PMC2952490          DOI： 10.1016/j.phytochem.2010.07.001

Source DB:  PubMed          Journal:  Phytochemistry        ISSN： 0031-9422            Impact factor:   4.072


  14 in total

1.  Two new malyngamides from a Madagascan Lyngbya majuscula.

Authors:  K E Milligan; B Márquez; R T Williamson; M Davies-Coleman; W H Gerwick
Journal:  J Nat Prod       Date:  2000-07       Impact factor: 4.050

Review 2.  Nitrogen-containing metabolites from marine cyanobacteria.

Authors:  W H Gerwick; L T Tan; N Sitachitta
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3.  Feasibility of drug screening with panels of human tumor cell lines using a microculture tetrazolium assay.

Authors:  M C Alley; D A Scudiero; A Monks; M L Hursey; M J Czerwinski; D L Fine; B J Abbott; J G Mayo; R H Shoemaker; M R Boyd
Journal:  Cancer Res       Date:  1988-02-01       Impact factor: 12.701

4.  Malyngamide H, an ichthyotoxic amide possessing a new carbon skeleton from the Caribbean cyanobacterium Lyngbya majuscula.

Authors:  J Orjala; D Nagle; W H Gerwick
Journal:  J Nat Prod       Date:  1995-05       Impact factor: 4.050

5.  Detection of sodium channel toxins: directed cytotoxicity assays of purified ciguatoxins, brevetoxins, saxitoxins, and seafood extracts.

Authors:  R L Manger; L S Leja; S Y Lee; J M Hungerford; Y Hokama; R W Dickey; H R Granade; R Lewis; T Yasumoto; M M Wekell
Journal:  J AOAC Int       Date:  1995 Mar-Apr       Impact factor: 1.913

6.  New malyngamides from the Hawaiian cyanobacterium Lyngbya majuscula.

Authors:  Y Kan; B Sakamoto; T Fujita; H Nagai
Journal:  J Nat Prod       Date:  2000-12       Impact factor: 4.050

7.  Malyngamides M and N from the Hawaiian Red Alga Gracilaria coronopifolia

Authors: 
Journal:  J Nat Prod       Date:  1998-01-23       Impact factor: 4.050

8.  Isolation and biological evaluation of 8-epi-malyngamide C from the Floridian marine cyanobacterium Lyngbya majuscula.

Authors:  Jason C Kwan; Max Teplitski; Sarath P Gunasekera; Valerie J Paul; Hendrik Luesch
Journal:  J Nat Prod       Date:  2010-03-26       Impact factor: 4.050

9.  Palmyramide A, a cyclic depsipeptide from a Palmyra Atoll collection of the marine cyanobacterium Lyngbya majuscula.

Authors:  Masatoshi Taniguchi; Joshawna K Nunnery; Niclas Engene; Eduardo Esquenazi; Tara Byrum; Pieter C Dorrestein; William H Gerwick
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  12 in total

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3.  Ketoreductase Domain Dysfunction Expands Chemodiversity: Malyngamide Biosynthesis in the Cyanobacterium Okeania hirsuta.

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4.  Quantitative molecular networking to profile marine cyanobacterial metabolomes.

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Review 6.  Cyanobacteria-From the Oceans to the Potential Biotechnological and Biomedical Applications.

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7.  Three New Malyngamides from the Marine Cyanobacterium Moorea producens.

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Review 9.  Marine cyanobacteria compounds with anticancer properties: a review on the implication of apoptosis.

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Review 10.  Cannabinomimetric Lipids: From Natural Extract to Artificial Synthesis.

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Journal:  Nat Prod Bioprospect       Date:  2018-01-16
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