Isolation and structural characterization of new, highly functionalized diterpenes from Euphorbia serrulata

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Abstract

Five new diterpene polyesters, 1-5, with jatrophane skeletons were isolated from the fresh whole plants of Euphorbia serrulata. The structure elucidation was performed by means of UV/VIS spectroscopy, HR-ESI-MS, and advanced two-dimensional NMR methods, including 1H-NMR, JMOD, 1H,1H-COSY, NOESY, HMQC, and HMBC experiments. The relative configurations of 1-5 and their conformations in solution were analyzed on the basis of NOESY measurements. As a result of detailed NMR studies, complete 1H and 13C chemical-shift assignments of the compounds were possible. The isolated compounds differ stereochemically and do not comprise a uniform series regarding the configurations at C(2), C(6), and C(13). Compound 5 possesses the new structural feature of a double bond with (Z)-configuration in the macrocyclic ring of the jatrophane skeleton, while compound 2 has a C=C bond in the five-membered ring, this being the first observation of this structural feature in the type of macrocyclic Euphorbiaceae diterpenes.

Original languageEnglish
Pages (from-to)280-289
Number of pages10
JournalHelvetica Chimica Acta
Volume86
Issue number2
DOIs
Publication statusPublished - jan. 1 2003

ASJC Scopus subject areas

  • Catalysis
  • Biochemistry
  • Drug Discovery
  • Physical and Theoretical Chemistry
  • Organic Chemistry
  • Inorganic Chemistry

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