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. 2011 Nov;72(16):2068-74.
doi: 10.1016/j.phytochem.2011.07.014. Epub 2011 Aug 16.

Pitipeptolides C-F, antimycobacterial cyclodepsipeptides from the marine cyanobacterium Lyngbya majuscula from Guam

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Pitipeptolides C-F, antimycobacterial cyclodepsipeptides from the marine cyanobacterium Lyngbya majuscula from Guam

Rana Montaser et al. Phytochemistry. 2011 Nov.

Abstract

Pitipeptolides A (1) and B (2) are cyclic depsipeptides isolated from the marine cyanobacterium Lyngbya majuscula from Piti Bomb Holes, Guam. Additional analogues have now been isolated by revisiting larger collections of the same cyanobacterium. The four identified analogues, pitipeptolides C-F (3-6), are the tetrahydro analogue (3), an analogue with a lower degree of methylation (4) as well as two homologues (5 and 6) of pitipeptolide A. Their structures were elucidated using 2D NMR experiments, chiral HPLC analysis and comparison with pitipeptolide A. The identified analogues showed weaker cytotoxic activities compared to the two major parent compounds, pitipeptolides A (1) and B (2), against HT-29 colon adenocarcinoma and MCF7 breast cancer cells. On the other hand, pitipeptolide F (6) was the most potent pitipeptolide in a disc diffusion assay against Mycobacterium tuberculosis. The latter finding suggests that the structure of pitipeptolides could be optimized for selective antibacterial activity.

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Figures

Figure 1
Figure 1
Structures of pitipeptolides A–F (1–6).
Figure 2
Figure 2
ESI-MS/MS fragmentation patterns of pitipeptolides C–F (3–6).
Figure 3
Figure 3
Structural comparison between pitipeptolide A (1) and antanapeptin A (7). Subunit sequences are shown below the structures; dotted lines indicate connected residues. The absolute configuration of the Hmoya unit in 7 is still unknown.

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