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Isolation and Structural Characterization of New, Highly Functionalized Diterpenes from Euphorbia serrulata

✍ Scribed by Dóra Rédei; Judit Hohmann; Ferenc Evanics; Peter Forgo; Pál Szabó; Imre Máthé

Publisher
John Wiley and Sons
Year
2003
Tongue
German
Weight
133 KB
Volume
86
Category
Article
ISSN
0018-019X

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✦ Synopsis

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 ^1^H‐NMR, JMOD, ^1^H,^1^H‐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 ^1^H and ^13^C 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.

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