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.
Biogenetical related highly oxygenated macrocyclic diterpenes from sea spurge Euphorbia paralias / E., Barile; Lanzotti, Virginia. - In: ORGANIC LETTERS. - ISSN 1523-7060. - ELETTRONICO. - 9:(2007), pp. 3603-3606. [10.1021/ol701454v]
Biogenetical related highly oxygenated macrocyclic diterpenes from sea spurge Euphorbia paralias
LANZOTTI, VIRGINIA
2007
Abstract
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.I documenti in IRIS sono protetti da copyright e tutti i diritti sono riservati, salvo diversa indicazione.