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 - 2003

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Euphorbia
Diterpenes
Skeleton
isolation
Nuclear magnetic resonance
Euphorbiaceae
musculoskeletal system
nuclear magnetic resonance
Polyesters
configurations
Spectrum Analysis
rings
Observation
polyesters
Chemical shift
Ultraviolet spectroscopy
chemical equilibrium
Conformations
spectroscopy
jatrophane

ASJC Scopus subject areas

  • Chemistry(all)

Cite this

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title = "Isolation and structural characterization of new, highly functionalized diterpenes from Euphorbia serrulata",
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.",
author = "D. R{\'e}dei and J. Hohmann and Ferenc Evanics and P. Forg{\'o} and P. Szab{\'o} and I. M{\'a}th{\'e}",
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T1 - Isolation and structural characterization of new, highly functionalized diterpenes from Euphorbia serrulata

AU - Rédei, D.

AU - Hohmann, J.

AU - Evanics, Ferenc

AU - Forgó, P.

AU - Szabó, P.

AU - Máthé, I.

PY - 2003

Y1 - 2003

N2 - 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.

AB - 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.

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