Amantelides A and B, Polyhydroxylated Macrolides with Differential Broad-Spectrum Cytotoxicity from a Guamanian Marine Cyanobacterium

J Nat Prod. 2015 Aug 28;78(8):1957-62. doi: 10.1021/acs.jnatprod.5b00293.

Lilibeth A Salvador-Reyes ¹, Jennifer Sneed ², Valerie J Paul ², Hendrik Luesch

Affiliations

1 Marine Science Institute, University of the Philippines , Velasquez Street, UP Diliman, Quezon City 1101, Philippines.
2 Smithsonian Marine Station , 701 Seaway Drive, Fort Pierce, Florida 34949, United States.

PMID: 26204500 DOI: 10.1021/acs.jnatprod.5b00293

Abstract

Cytotoxicity-guided fractionation of a Guamanian cyanobacterial collection yielded the new compounds amantelides A (1) and B (2). These polyketides are characterized by a 40-membered macrolactone ring consisting of a 1,3-diol and contiguous 1,5-diol units and a tert-butyl substituent. Amantelide A (1) displayed potent cytotoxicity with submicromolar IC₅₀ against HT29 colorectal adenocarcinoma and HeLa cervical carcinoma cell lines. Acetylation of the hydroxy group at C-33 in 2 caused a close to 10-fold decrease in potency. Exhaustive acetylation of the hydroxy groups abrogated the antiproliferative activity of amantelide A (1) by 20-67-fold. Further bioactivity assessment of 1 against Bacterial pathogens and marine fungi indicated a broad spectrum of bioactivity.

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