Thalassospiramides A and B, immunosuppressive peptides from the marine bacterium Thalassospira sp.
[structure: see text] Two new cyclic peptides, thalassospiramides A and B (1 and 2), were isolated from a new member of the marine alpha-proteobacterium Thalassospira. The thalassospiramides, the structures of which were assigned by combined spectral and chemical methods, bear unusual gamma-amino acids and show immunosuppressive activity in an interleukin-5 production inhibition assay (IC50 = 5 muM for thalassospiramide B).
Oh
Dong-Chan
DC
Center for Marine Biotechnology and Biomedicine, Scripps Institution of Oceanography, University of California-San Diego, La Jolla, California 92093, USA.
Strangman
Wendy K
WK
Kauffman
Christopher A
CA
Jensen
Paul R
PR
Fenical
William
W
D000586:Amination; D000818:Animals; D006900:Hydroxylation; D007166:Immunosuppressive Agents / Q000737:chemistry* / Q000378:metabolism / Q000494:pharmacology; D008214:Lymphocytes / Q000187:drug effects; D009682:Magnetic Resonance Spectroscopy; D051379:Mice; D015394:Molecular Structure; D009792:Oceans and Seas; D010421:Pentanoic Acids / Q000737:chemistry; D010456:Peptides, Cyclic / Q000096:biosynthesis / Q000737:chemistry* / Q000494:pharmacology; D012244:Rhodospirillaceae / Q000737:chemistry* / Q000378:metabolism
D007166:Immunosuppressive Agents; D010421:Pentanoic Acids; D010456:Peptides, Cyclic; C520245:thalassospiramide A; C520244:thalassospiramide B