Isolation and Structure Determination of New Jatrophane Diterpenoids from Euphorbia platyphyllos L.

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Abstract

Three new, highly functionalized jatrophane diterpenes (1-3) have been isolated from the whole, dried plants of Euphorbia platyphyllos L., together with one known jatrophane polyester (4). The structures were established by UV/VIS spectroscopy, HR-ESI-MS, and advanced two-dimensional NMR, including 1H-NMR, JMOD, 1H,1H-COSY, HMQC, and HMBC experiments. Stereochemical studies and conformational analyses were performed by means of NOESY experiments. Interestingly, compounds 1-4 do not represent a stereochemically uniform series because they differ in the orientations of the Me groups at C(2), C(6), and C(13). A similar observation was reported earlier for Euphorbia serrulata, whose diterpenes are related to the compounds obtained from E. platyphyllos. This chemical relationship is of taxonomic importance and supports the botanical similarity of the two species.

Original languageEnglish
Pages (from-to)3386-3393
Number of pages8
JournalHelvetica Chimica Acta
Volume86
Issue number10
DOIs
Publication statusPublished - 2003

Fingerprint

Euphorbia
Diterpenes
isolation
Nuclear magnetic resonance
nuclear magnetic resonance
Polyesters
polyesters
Ultraviolet spectroscopy
Spectrum Analysis
Experiments
spectroscopy
jatrophane
Proton Magnetic Resonance Spectroscopy
vitamin B 12 factor III

ASJC Scopus subject areas

  • Chemistry(all)

Cite this

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title = "Isolation and Structure Determination of New Jatrophane Diterpenoids from Euphorbia platyphyllos L.",
abstract = "Three new, highly functionalized jatrophane diterpenes (1-3) have been isolated from the whole, dried plants of Euphorbia platyphyllos L., together with one known jatrophane polyester (4). The structures were established by UV/VIS spectroscopy, HR-ESI-MS, and advanced two-dimensional NMR, including 1H-NMR, JMOD, 1H,1H-COSY, HMQC, and HMBC experiments. Stereochemical studies and conformational analyses were performed by means of NOESY experiments. Interestingly, compounds 1-4 do not represent a stereochemically uniform series because they differ in the orientations of the Me groups at C(2), C(6), and C(13). A similar observation was reported earlier for Euphorbia serrulata, whose diterpenes are related to the compounds obtained from E. platyphyllos. This chemical relationship is of taxonomic importance and supports the botanical similarity of the two species.",
author = "J. Hohmann and P. Forg{\'o} and Dezs{\"o} Csupor and G. Schlosser",
year = "2003",
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journal = "Helvetica Chimica Acta",
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TY - JOUR

T1 - Isolation and Structure Determination of New Jatrophane Diterpenoids from Euphorbia platyphyllos L.

AU - Hohmann, J.

AU - Forgó, P.

AU - Csupor, Dezsö

AU - Schlosser, G.

PY - 2003

Y1 - 2003

N2 - Three new, highly functionalized jatrophane diterpenes (1-3) have been isolated from the whole, dried plants of Euphorbia platyphyllos L., together with one known jatrophane polyester (4). The structures were established by UV/VIS spectroscopy, HR-ESI-MS, and advanced two-dimensional NMR, including 1H-NMR, JMOD, 1H,1H-COSY, HMQC, and HMBC experiments. Stereochemical studies and conformational analyses were performed by means of NOESY experiments. Interestingly, compounds 1-4 do not represent a stereochemically uniform series because they differ in the orientations of the Me groups at C(2), C(6), and C(13). A similar observation was reported earlier for Euphorbia serrulata, whose diterpenes are related to the compounds obtained from E. platyphyllos. This chemical relationship is of taxonomic importance and supports the botanical similarity of the two species.

AB - Three new, highly functionalized jatrophane diterpenes (1-3) have been isolated from the whole, dried plants of Euphorbia platyphyllos L., together with one known jatrophane polyester (4). The structures were established by UV/VIS spectroscopy, HR-ESI-MS, and advanced two-dimensional NMR, including 1H-NMR, JMOD, 1H,1H-COSY, HMQC, and HMBC experiments. Stereochemical studies and conformational analyses were performed by means of NOESY experiments. Interestingly, compounds 1-4 do not represent a stereochemically uniform series because they differ in the orientations of the Me groups at C(2), C(6), and C(13). A similar observation was reported earlier for Euphorbia serrulata, whose diterpenes are related to the compounds obtained from E. platyphyllos. This chemical relationship is of taxonomic importance and supports the botanical similarity of the two species.

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JO - Helvetica Chimica Acta

JF - Helvetica Chimica Acta

SN - 0018-019X

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