Identification of amphilectosins as key intermediates in pseudopterosin biosynthesis.
Amphilectosins A and B have been identified from the organic extract of Pseudopterogorgia elisabethae collected in the Florida Keys, along with seco-pseudopterosins and pseudopterosins. The structures of the amphilectosins, "C-12-C-13 dehydro seco-pseudopterosins", suggested that these metabolites provide the biosynthetic link between the seco-pseudopterosins (serrulatane diterpenes) and pseudopterosins (amphilectane diterpenes). This biosynthetic relationship was confirmed through various radiolabeling experiments. Incubation studies with the amphilectosins revealed the selective transformation of amphilectosin A to pseudopterosin Y and the transformation of amphilectosin B to pseudopterosin F, which suggests that the alpha/beta stereochemistry for the isobutenyl group in the pseudopterosins arises from the selective ring closure of the cis- and trans-amphilectosins.
Ferns
Tyrone A
TA
Department of Chemistry and Biochemistry, Center of Excellence in Biomedical and Marine Biotechnology, Florida Atlantic University, Boca Raton, Florida 33431, USA.
Kerr
Russell G
RG
D000818:Animals; D037421:Anthozoa / Q000737:chemistry / Q000378:metabolism; D004224:Diterpenes / Q000097:blood / Q000737:chemistry* / Q000378:metabolism*; D006027:Glycosides / Q000096:biosynthesis* / Q000097:blood / Q000737:chemistry* / Q000378:metabolism*; D015394:Molecular Structure
D004224:Diterpenes; D006027:Glycosides; C504695:amphilectosin A; C504696:amphilectosin B; C049922:pseudopterosins