Antineoplastic diterpene-benzoate macrolides from the Fijian red alga Callophycus serratus.
[structures: see text] Three diterpene-benzoate natural products, with novel carbon skeletons and an unusual proposed biosynthesis, were isolated from extracts of the Fijian red alga Callophycus serratus and identified by a combination of X-ray crystallographic, NMR, and mass spectral analyses. Bromophycolide A (1) displayed cytotoxicity against several human tumor cell lines via specific apoptotic cell death. This represents the first discovery of natural products incorporating a diterpene and benzoate skeleton into a macrolide system.
Kubanek
Julia
J
School of Biology and School of Chemistry and Biochemistry, Georgia Institute of Technology, Atlanta, Georgia 30332, USA. julia.kubanek@biology.gatech.edu
Prusak
Anne C
AC
Snell
Terry W
TW
Giese
Rachel A
RA
Hardcastle
Kenneth I
KI
Fairchild
Craig R
CR
Aalbersberg
William
W
Raventos-Suarez
Carmen
C
Hay
Mark E
ME
D000900:Anti-Bacterial Agents / Q000737:chemistry / Q000302:isolation & purification / Q000494:pharmacology; D019380:Anti-HIV Agents / Q000737:chemistry / Q000302:isolation & purification / Q000494:pharmacology; D000970:Antineoplastic Agents / Q000737:chemistry / Q000302:isolation & purification* / Q000494:pharmacology; D001565:Benzoates / Q000737:chemistry / Q000302:isolation & purification* / Q000494:pharmacology; D004224:Diterpenes / Q000737:chemistry / Q000302:isolation & purification* / Q000494:pharmacology; D024881:Drug Resistance, Bacterial; D004354:Drug Screening Assays, Antitumor; D005367:Fiji; D006801:Humans; D018942:Macrolides / Q000737:chemistry / Q000302:isolation & purification* / Q000494:pharmacology; D008826:Microbial Sensitivity Tests; D015394:Molecular Structure; D019906:Nuclear Magnetic Resonance, Biomolecular; D000461:Rhodophyta / Q000737:chemistry*; D014407:Tumor Cells, Cultured
D000900:Anti-Bacterial Agents; D019380:Anti-HIV Agents; D000970:Antineoplastic Agents; D001565:Benzoates; D004224:Diterpenes; D018942:Macrolides; C512010:bromophycolide A