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

Shogo Mori; Howard Williams; Davey Cagle; Kristopher Karanovich; F David Horgen; Roger Smith III; Coran M H Watanabe

doi:10.3390/md13106274

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

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

Authors

Shogo Mori¹, Howard Williams², Davey Cagle³, Kristopher Karanovich⁴, F David Horgen⁵, Roger Smith III⁶, Coran M H Watanabe⁷

Affiliations

¹ Department of Chemistry, Texas A&M University, College Station, TX 77843, USA. smori@mail.chem.tamu.edu.
² Department of Chemistry, Texas A&M University, College Station, TX 77843, USA. williams@cbnmr.chem.tamu.edu.
³ Department of Natural Sciences, Hawaii Pacific University, Kaneohe, HI 96744, USA. dcagle@my.hpu.edu.
⁴ Department of Natural Sciences, Hawaii Pacific University, Kaneohe, HI 96744, USA. kkaranovich@gmail.com.
⁵ Department of Natural Sciences, Hawaii Pacific University, Kaneohe, HI 96744, USA. dhorgen@hpu.edu.
⁶ Department of Veterinary Pathology, Texas A&M University, College Station, TX 77843, USA. ROSmith@cvm.tamu.edu.
⁷ Department of Chemistry, Texas A&M University, College Station, TX 77843, USA. watanabe@mail.chem.tamu.edu.

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.

Publication types

Research Support, N.I.H., Extramural
Research Support, Non-U.S. Gov't

MeSH terms

Cell Division / drug effects
Cell Migration Inhibition / drug effects
Chemotaxis / drug effects*
Cyanobacteria / chemistry*
G2 Phase / drug effects
Hawaii
Humans
Jurkat Cells
Leukemia, T-Cell / drug therapy
Macrolides / chemistry
Macrolides / isolation & purification
Macrolides / pharmacology*

Substances

Macrolides
nuiapolide

Abstract

Publication types

MeSH terms

Substances

Grants and funding