Lyngbyaloside B, a new glycoside macrolide from a Palauan marine cyanobacterium, Lyngbya sp.
A Palauan collection of the marine cyanobacterium Lyngbya sp., which had already afforded diverse peptide-based cytotoxins, also yielded a new glycoside macrolide exhibiting slight cytotoxicity. The compound was termed lyngbyaloside B (1) due to its structural analogy to the previously isolated lyngbyaloside (2). Lyngbyaloside B (1) appears to be only the third glycoside macrolide and second brominated compound of its kind from a marine cyanobacterium. Its gross structure was determined by a combination of NMR spectroscopy and mass spectrometric techniques. The relative stereochemistry for the 12 stereocenters is proposed on the basis of proton-proton spin-coupling constants and ROESY data.
Luesch
Hendrik
H
Department of Chemistry, University of Hawaii at Manoa, Honolulu, HI 96822, USA.
Yoshida
Wesley Y
WY
Harrigan
George G
GG
Doom
James P
JP
Moore
Richard E
RE
Paul
Valerie J
VJ
D000458:Cyanobacteria / Q000737:chemistry*; D004354:Drug Screening Assays, Antitumor; D006027:Glycosides / Q000737:chemistry / Q000302:isolation & purification* / Q000494:pharmacology; D006801:Humans; D020128:Inhibitory Concentration 50; D007624:KB Cells / Q000187:drug effects; D008235:Lyngbya Toxins / Q000737:chemistry / Q000302:isolation & purification* / Q000494:pharmacology; D018942:Macrolides / Q000737:chemistry / Q000302:isolation & purification* / Q000494:pharmacology; D008968:Molecular Conformation; D015394:Molecular Structure; D019906:Nuclear Magnetic Resonance, Biomolecular; D019029:Palau; D013237:Stereoisomerism; D014407:Tumor Cells, Cultured / Q000187:drug effects
D006027:Glycosides; D008235:Lyngbya Toxins; D018942:Macrolides; C473445:lyngbyaloside B