Macrocyclic diterpenoids from Euphorbia hyberna L. subsp. insularis and their reaction with oxyphilic reagents

G. Appendino; P. Spagliardi; M. Ballero; G. Seu

doi:10.1016/S0367-326X(02)00213-7

Macrocyclic diterpenoids from Euphorbia hyberna L. subsp. insularis and their reaction with oxyphilic reagents

G. Appendino
, P. Spagliardi
, M. Ballero
, G. Seu

Risultato della ricerca: Contributo su rivista › Articolo in rivista › peer review

Abstract

The aerial parts of Euphorbia hyberna subsp. insularis from Sardinia contain large amounts of macrocyclic diterpenoids of the jatrophane type, while phorboids could not be isolated. Treatment of the major constituent (1a) with various acidic and oxyphilic reagents was investigated, showing the surprising reluctance of the macrocyclic system to undergo transannular reactions. Dehydration, isomerization of the exocyclic double and acyl rearrangement were, however, observed after reduction of the 9-keto group.

Lingua originale	Inglese
pagine (da-a)	576-582
Numero di pagine	7
Rivista	Fitoterapia
Volume	73
Numero di pubblicazione	7-8
DOI	https://doi.org/10.1016/S0367-326X(02)00213-7
Stato di pubblicazione	Pubblicato - dic 2002
Pubblicato esternamente	Sì

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10.1016/S0367-326X(02)00213-7

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@article{58c105a3d36649159a80f9162a3301c3,

title = "Macrocyclic diterpenoids from Euphorbia hyberna L. subsp. insularis and their reaction with oxyphilic reagents",

abstract = "The aerial parts of Euphorbia hyberna subsp. insularis from Sardinia contain large amounts of macrocyclic diterpenoids of the jatrophane type, while phorboids could not be isolated. Treatment of the major constituent (1a) with various acidic and oxyphilic reagents was investigated, showing the surprising reluctance of the macrocyclic system to undergo transannular reactions. Dehydration, isomerization of the exocyclic double and acyl rearrangement were, however, observed after reduction of the 9-keto group.",

keywords = "Chemotaxonomy, Diterpenoids, Euphorbia hyberna subsp. insularis, Jatrophanes, Phorboids",

author = "G. Appendino and P. Spagliardi and M. Ballero and G. Seu",

note = "Funding Information: This work was supported by MURST (Fondi ex-40\%, Progetto Sostanze Naturali e Analoghi Sintetici con Attivit{\`a} Antitumorale). We are grateful to Dr Jasmin Jakupovic (AnalytiCon Discovery, Potsdam, Germany) for useful discussions on the structure elucidation of the compounds and to Dr R. Sestu and the Pro Loco Arzana for their hospitality and help during the collection of the plant material. ",

year = "2002",

month = dec,

doi = "10.1016/S0367-326X(02)00213-7",

language = "English",

volume = "73",

pages = "576--582",

journal = "Fitoterapia",

issn = "0367-326X",

publisher = "Elsevier B.V.",

number = "7-8",

}

TY - JOUR

T1 - Macrocyclic diterpenoids from Euphorbia hyberna L. subsp. insularis and their reaction with oxyphilic reagents

AU - Appendino, G.

AU - Spagliardi, P.

AU - Ballero, M.

AU - Seu, G.

N1 - Funding Information: This work was supported by MURST (Fondi ex-40%, Progetto Sostanze Naturali e Analoghi Sintetici con Attività Antitumorale). We are grateful to Dr Jasmin Jakupovic (AnalytiCon Discovery, Potsdam, Germany) for useful discussions on the structure elucidation of the compounds and to Dr R. Sestu and the Pro Loco Arzana for their hospitality and help during the collection of the plant material.

PY - 2002/12

Y1 - 2002/12

N2 - The aerial parts of Euphorbia hyberna subsp. insularis from Sardinia contain large amounts of macrocyclic diterpenoids of the jatrophane type, while phorboids could not be isolated. Treatment of the major constituent (1a) with various acidic and oxyphilic reagents was investigated, showing the surprising reluctance of the macrocyclic system to undergo transannular reactions. Dehydration, isomerization of the exocyclic double and acyl rearrangement were, however, observed after reduction of the 9-keto group.

AB - The aerial parts of Euphorbia hyberna subsp. insularis from Sardinia contain large amounts of macrocyclic diterpenoids of the jatrophane type, while phorboids could not be isolated. Treatment of the major constituent (1a) with various acidic and oxyphilic reagents was investigated, showing the surprising reluctance of the macrocyclic system to undergo transannular reactions. Dehydration, isomerization of the exocyclic double and acyl rearrangement were, however, observed after reduction of the 9-keto group.

KW - Chemotaxonomy

KW - Diterpenoids

KW - Euphorbia hyberna subsp. insularis

KW - Jatrophanes

KW - Phorboids

UR - https://www.scopus.com/pages/publications/0036915814

U2 - 10.1016/S0367-326X(02)00213-7

DO - 10.1016/S0367-326X(02)00213-7

M3 - Article

SN - 0367-326X

VL - 73

SP - 576

EP - 582

JO - Fitoterapia

JF - Fitoterapia

IS - 7-8

ER -

Macrocyclic diterpenoids from Euphorbia hyberna L. subsp. insularis and their reaction with oxyphilic reagents

Abstract

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