Biogenetical related highly oxygenated macrocyclic diterpenes from sea spurge Euphorbia paralias.
A new tricyclic diterpenoid, named pre-segetanin (1), and two new diterpenes, named segetanin A and B (2 and 3), the latter based on the rare segetane skeleton, have been identified from the whole plant of sea spurge along with four known segetane diterpenes (4-7). Among them, pre-segetanin (1) has an unprecedented carbon skeleton, whose isolation provides a first insight into the biosynthesis of diterpenoids with a segetane skeleton. The stereostructure elucidation of the isolated metabolites was determined by extensive spectroscopic analysis, including 1D and 2D NMR (COSY, TOCSY, HSQC, HMBC, and ROESY) and HRFABMS experiments.
Barile
Elisa
E
Dipartimento di Scienze e Tecnologie Agroalimentari, Ambientali e Microbiologiche, Università del Molise, Via F. De Sanctis, 86100 Campobasso, Italy.
Lanzotti
Virginia
V
D004224:Diterpenes / Q000737:chemistry* / Q000302:isolation & purification; D028481:Euphorbia / Q000737:chemistry*; D047028:Macrocyclic Compounds / Q000737:chemistry*; D009682:Magnetic Resonance Spectroscopy; D015394:Molecular Structure
D004224:Diterpenes; D047028:Macrocyclic Compounds; C524022:pre-segetanin; C524023:segetanin A; C524021:segetanin B