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Planta Med 2016; 82(09/10): 897-902
DOI: 10.1055/s-0042-105157
Original Papers
Georg Thieme Verlag KG Stuttgart · New York

Pitiamides A and B, Multifunctional Fatty Acid Amides from Marine Cyanobacteria

Weijing Cai
1   Department of Medicinal Chemistry, University of Florida, Gainesville, Florida, USA
2   Center for Natural Products, Drug Discovery and Development (CNPD3), University of Florida, Gainesville, Florida, USA
,
James H. Matthews
1   Department of Medicinal Chemistry, University of Florida, Gainesville, Florida, USA
2   Center for Natural Products, Drug Discovery and Development (CNPD3), University of Florida, Gainesville, Florida, USA
,
Valerie J. Paul
3   Smithsonian Marine Station, Fort Pierce, Florida, USA
,
Hendrik Luesch
1   Department of Medicinal Chemistry, University of Florida, Gainesville, Florida, USA
2   Center for Natural Products, Drug Discovery and Development (CNPD3), University of Florida, Gainesville, Florida, USA
› Author Affiliations
Further Information

Publication History

received 24 September 2015
revised 18 February 2016

accepted 04 March 2016

Publication Date:
02 May 2016 (online)

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Abstract

Two geometric isomers related to pitiamide A, termed 1E-pitiamide B (1) and 1Z-pitiamide B (2), were isolated from a marine cyanobacterium collected from the shallow reef flat at Piti Bomb Holes, Guam, Mariana Islands. The structures of these analogues were elucidated using 1D and 2D NMR analysis. Pitiamide A, which has been previously described, but has not been investigated in bioassays, was co-isolated. Pitiamides A and B were subjected to a biological evaluation and they both showed antiproliferative effects on HCT116 cells with IC50 values of 1–5 µM. Pitiamide A was investigated individually and caused plasma membrane hyperpolarization and an increase of intracellular calcium in HCT116 cells.

Key words

Marine cyanobacteria - fatty acid amides - pitiamides - antiproliferative activity - membrane hyperpolarization

Supporting Information

 

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