Elysiapyrones from Elysia diomedea. Do such metabolites evidence an enzymatically assisted electrocyclization cascade for the biosynthesis of their bicyclo[4.2.0]octane core?
[structure: see text] Biogenetically interesting polypropionate-derived metabolites 1 and 2, featuring an unprecedented skeleton, have been isolated from the sea slug Elysia diomedea. Their enantiomeric character indicates that the current spontaneous electrocyclization cascade biogenetic hypothesis for the bicyclo[4.2.0]octane core must be enzymatically aided. These compounds are isomeric with the 15-nor-9,10-deoxytridachione/15-norphotodeoxytridachione pair of metabolites and encourage speculation about their biosynthetic relationship.
Cueto
Mercedes
M
Instituto de Productos Naturales y Agrobiología del CSIC, Avda. Astrofísico F. Sánchez 3, 38206 La Laguna, Tenerife, Spain.
D'Croz
Luis
L
Maté
Juan L
JL
San-Martín
Aurelio
A
Darias
José
J
D000818:Animals; D019086:Bridged Bicyclo Compounds, Heterocyclic / Q000737:chemistry*; D003500:Cyclization; D004563:Electrochemistry; D017665:Hydroxyl Radical; D009682:Magnetic Resonance Spectroscopy; D008968:Molecular Conformation; D008974:Mollusca / Q000737:chemistry*; D013237:Stereoisomerism
D019086:Bridged Bicyclo Compounds, Heterocyclic; C509577:elysiapyrone A; C509578:elysiapyrone B; D017665:Hydroxyl Radical