Journal
JOURNAL OF NATURAL PRODUCTS
Volume 78, Issue 8, Pages 1957-1962Publisher
AMER CHEMICAL SOC
DOI: 10.1021/acs.jnatprod.5b00293
Keywords
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Funding
- National Institutes of Health
- NIGMS [P41GM086210]
- NCI [R01CA172310]
- University of the Philippines Office of the Vice Chancellor for Research and Development
- UP Balik Ph.D. program
- NATIONAL CANCER INSTITUTE [R01CA172310] Funding Source: NIH RePORTER
- NATIONAL INSTITUTE OF GENERAL MEDICAL SCIENCES [P41GM086210] Funding Source: NIH RePORTER
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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 He La 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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