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. 2015 Oct 9;13(10):6274-90.
doi: 10.3390/md13106274.

Macrolactone Nuiapolide, Isolated from a Hawaiian Marine Cyanobacterium, Exhibits Anti-Chemotactic Activity

Shogo Mori  1 , Howard Williams  2 , Davey Cagle  3 , Kristopher Karanovich  4 , F David Horgen  5 , Roger Smith III  6 , Coran M H Watanabe  7
Affiliations

Macrolactone Nuiapolide, Isolated from a Hawaiian Marine Cyanobacterium, Exhibits Anti-Chemotactic Activity

Shogo Mori et al. Mar Drugs. .

Abstract

A new bioactive macrolactone, nuiapolide (1) was identified from a marine cyanobacterium collected off the coast of Niihau, near Lehua Rock. The natural product exhibits anti-chemotactic activity at concentrations as low as 1.3 μM against Jurkat cells, cancerous T lymphocytes, and induces a G2/M phase cell cycle shift. Structural characterization of the natural product revealed the compound to be a 40-membered macrolactone with nine hydroxyl functional groups and a rare tert-butyl carbinol residue.

Keywords: cell cycle; chemotaxis; cyanobacteria; macrolactone; polyketide.

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Figures

Figure 1
Figure 1
Evaluation of Jurkat cultures in the Boyden chamber assay. Images of microscope fields of the bottom well after 24 h of incubation. (a) Bottom well received no FBS and no test substance; (b) Bottom well received 10% FBS and no test substance; (c) Bottom well received 10% FBS and FTY720 (5 µg/mL); (d) Bottom well received 10% FBS and 13-F10 extract (25 µg/mL). Shrinkage of cells in (c) is indicative of cell death.
Figure 2
Figure 2
Cytotoxicity profile analysis of extracts: The turquoise bar represents samples where the percentage of live cells is ≥90% of the control. The black bar represents samples where the percentage of live cells is <90%. Controls included wells grown without FBS (−FBS) and with FTY720 (1 or 5 µg/mL). Sample codes are library plate number and coordinate on the plate. (a) Sample set 10- to 15- and (b) sample set 16- and 17-.
Figure 3
Figure 3
Evaluation of nuiapolide (1) activity at 1 µg/mL. Images of microscope fields of the bottom well after 24 h of incubation. (a) Bottom well received no FBS and no test substance; (b) Bottom well received 10% FBS and no test substance; (c) Bottom well received 10% FBS and FTY720 (5 µg/mL); (d) Bottom well received 10% FBS and nuiapolide (1) (1 µg/mL).
Figure 4
Figure 4
Cell cycle analysis of Jurkat cells treated with nuiapolide (1), 5 μg/mL. (a) Histograms of Jurkat cells stained with propidium iodide (numbers in the legend indicate the number of cells plotted for each treatment); (b) Table providing the % of cells distributed in each stage of the cell cycle.
Figure 5
Figure 5
Partial structure of nuiapolide (1) with key HMBC correlations.
Figure 6
Figure 6
Structure of nuiapolide (1) and caylobolides A (2) and B (3).
See this image and copyright information in PMC

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