Natural products chemistry and taxonomy of the marine cyanobacterium Blennothrix cantharidosmum.
A Papua New Guinea field collection of the marine cyanobacterium Blennothrix cantharidosmum was investigated for its cytotoxic constituents. Bioassay-guided isolation defined the cytotoxic components as the known compounds lyngbyastatins 1 and 3. However, six new acyl proline derivatives, tumonoic acids D-I, plus the known tumonoic acid A were also isolated. Their planar structures were defined from NMR and MS data, while their stereostructures followed from a series of chiral chromatographies, degradation sequences, and synthetic approaches. The new compounds were tested in an array of assays, but showed only modest antimalarial and inhibition of quorum sensing activities. Nevertheless, these are the first natural products to be reported from this genus, and this inspired a detailed morphologic and 16S rDNA-based phylogenetic analysis of the producing organism.
Clark
Benjamin R
BR
Scripps Institution of Oceanography, University of California San Diego, 9500 Gilman Drive, La Jolla, California 92093-0212, USA.
Engene
Niclas
N
Teasdale
Margaret E
ME
Rowley
David C
DC
Matainaho
Teatulohi
T
Valeriote
Frederick A
FA
Gerwick
William H
WH
D000818:Animals; D000962:Antimalarials / Q000737:chemistry / Q000302:isolation & purification / Q000494:pharmacology; D000458:Cyanobacteria / Q000737:chemistry* / Q000235:genetics; D004269:DNA, Bacterial / Q000032:analysis / Q000235:genetics; D004354:Drug Screening Assays, Antitumor; D008235:Lyngbya Toxins / Q000737:chemistry / Q000302:isolation & purification / Q000494:pharmacology; D008826:Microbial Sensitivity Tests; D015394:Molecular Structure; D009842:Oligopeptides / Q000737:chemistry / Q000302:isolation & purification*; D010219:Papua New Guinea; D010456:Peptides, Cyclic / Q000737:chemistry / Q000302:isolation & purification*; D011392:Proline / Q000031:analogs & derivatives / Q000737:chemistry; D053038:Quorum Sensing / Q000187:drug effects; D012336:RNA, Ribosomal, 16S / Q000032:analysis / Q000235:genetics
D000962:Antimalarials; D004269:DNA, Bacterial; D008235:Lyngbya Toxins; D009842:Oligopeptides; D010456:Peptides, Cyclic; D012336:RNA, Ribosomal, 16S; C115557:lyngbyastatin 1; C481240:lyngbyastatin 3; C532610:tumonoic acid D; D011392:Proline