Discovery and biological evaluation of the novel naturally occurring diterpene pepluanone as antiinflammatory agent

G. Corea, E. Fattorusso, V. Lanzotti, P. Di Meglio, P. Maffia, G. Grassia, A. Ialenti, A. Ianaro

Research output: Contribution to journalArticle

41 Citations (Scopus)

Abstract

From the whole plant of Euphorbia peplus L., a new diterpene based on a rare pepluane skeleton, named pepluanone (1), was isolated together with a known pepluane diterpene (2). The stereostructure of pepluanone was determined on the basis of an extensive NMR study, MS data, and chemical reaction. The ability of these compounds to act as antiinflammatory agents has been evaluated for the first time by in vivo tests on carrageenin-induced rat paw edema, an experimental model of acute inflammation. Comparison of the bioactivity of pepluanone and compound 2 in terms of chemical structure, evidenced the high efficiency of pepluanone and the absence of appreciable activity for compound 2, thus giving a first insight into the structure−activity relationship. Further in vitro experiments performed on pepluanone let us hypothesize that its activity could be explained in reducing the production of nitric oxide, prostaglandin E2, and TNF-α by inhibiting the expression of inducible nitric oxide synthase, cyclooxygenase-2, and TNF-α mRNA through the down-regulation of NF-κB binding activity.
LanguageEnglish
Pages7055-7062
Number of pages8
JournalJournal of Medicinal Chemistry
Volume48
Issue number22
DOIs
Publication statusPublished - 2005

Fingerprint

Diterpenes
Anti-Inflammatory Agents
Tumor Necrosis Factor-alpha
Euphorbia
Carrageenan
Nitric Oxide Synthase Type II
Cyclooxygenase 2
Structure-Activity Relationship
Dinoprostone
Skeleton
Edema
Nitric Oxide
Theoretical Models
Down-Regulation
pepluanone
Inflammation
Messenger RNA

Keywords

  • antiinflammatory agents
  • pharmacy
  • medicine

Cite this

Corea, G., Fattorusso, E., Lanzotti, V., Di Meglio, P., Maffia, P., Grassia, G., ... Ianaro, A. (2005). Discovery and biological evaluation of the novel naturally occurring diterpene pepluanone as antiinflammatory agent. Journal of Medicinal Chemistry, 48(22), 7055-7062. https://doi.org/10.1021/jm050321r
Corea, G. ; Fattorusso, E. ; Lanzotti, V. ; Di Meglio, P. ; Maffia, P. ; Grassia, G. ; Ialenti, A. ; Ianaro, A. / Discovery and biological evaluation of the novel naturally occurring diterpene pepluanone as antiinflammatory agent. In: Journal of Medicinal Chemistry. 2005 ; Vol. 48, No. 22. pp. 7055-7062.
@article{edb1ffceeb284962835dd54754d65d1c,
title = "Discovery and biological evaluation of the novel naturally occurring diterpene pepluanone as antiinflammatory agent",
abstract = "From the whole plant of Euphorbia peplus L., a new diterpene based on a rare pepluane skeleton, named pepluanone (1), was isolated together with a known pepluane diterpene (2). The stereostructure of pepluanone was determined on the basis of an extensive NMR study, MS data, and chemical reaction. The ability of these compounds to act as antiinflammatory agents has been evaluated for the first time by in vivo tests on carrageenin-induced rat paw edema, an experimental model of acute inflammation. Comparison of the bioactivity of pepluanone and compound 2 in terms of chemical structure, evidenced the high efficiency of pepluanone and the absence of appreciable activity for compound 2, thus giving a first insight into the structure−activity relationship. Further in vitro experiments performed on pepluanone let us hypothesize that its activity could be explained in reducing the production of nitric oxide, prostaglandin E2, and TNF-α by inhibiting the expression of inducible nitric oxide synthase, cyclooxygenase-2, and TNF-α mRNA through the down-regulation of NF-κB binding activity.",
keywords = "antiinflammatory agents , pharmacy , medicine",
author = "G. Corea and E. Fattorusso and V. Lanzotti and {Di Meglio}, P. and P. Maffia and G. Grassia and A. Ialenti and A. Ianaro",
year = "2005",
doi = "10.1021/jm050321r",
language = "English",
volume = "48",
pages = "7055--7062",
journal = "Journal of Medicinal Chemistry",
issn = "0022-2623",
publisher = "American Chemical Society",
number = "22",

}

Corea, G, Fattorusso, E, Lanzotti, V, Di Meglio, P, Maffia, P, Grassia, G, Ialenti, A & Ianaro, A 2005, 'Discovery and biological evaluation of the novel naturally occurring diterpene pepluanone as antiinflammatory agent' Journal of Medicinal Chemistry, vol. 48, no. 22, pp. 7055-7062. https://doi.org/10.1021/jm050321r

Discovery and biological evaluation of the novel naturally occurring diterpene pepluanone as antiinflammatory agent. / Corea, G.; Fattorusso, E.; Lanzotti, V.; Di Meglio, P.; Maffia, P.; Grassia, G.; Ialenti, A.; Ianaro, A.

In: Journal of Medicinal Chemistry, Vol. 48, No. 22, 2005, p. 7055-7062.

Research output: Contribution to journalArticle

TY - JOUR

T1 - Discovery and biological evaluation of the novel naturally occurring diterpene pepluanone as antiinflammatory agent

AU - Corea, G.

AU - Fattorusso, E.

AU - Lanzotti, V.

AU - Di Meglio, P.

AU - Maffia, P.

AU - Grassia, G.

AU - Ialenti, A.

AU - Ianaro, A.

PY - 2005

Y1 - 2005

N2 - From the whole plant of Euphorbia peplus L., a new diterpene based on a rare pepluane skeleton, named pepluanone (1), was isolated together with a known pepluane diterpene (2). The stereostructure of pepluanone was determined on the basis of an extensive NMR study, MS data, and chemical reaction. The ability of these compounds to act as antiinflammatory agents has been evaluated for the first time by in vivo tests on carrageenin-induced rat paw edema, an experimental model of acute inflammation. Comparison of the bioactivity of pepluanone and compound 2 in terms of chemical structure, evidenced the high efficiency of pepluanone and the absence of appreciable activity for compound 2, thus giving a first insight into the structure−activity relationship. Further in vitro experiments performed on pepluanone let us hypothesize that its activity could be explained in reducing the production of nitric oxide, prostaglandin E2, and TNF-α by inhibiting the expression of inducible nitric oxide synthase, cyclooxygenase-2, and TNF-α mRNA through the down-regulation of NF-κB binding activity.

AB - From the whole plant of Euphorbia peplus L., a new diterpene based on a rare pepluane skeleton, named pepluanone (1), was isolated together with a known pepluane diterpene (2). The stereostructure of pepluanone was determined on the basis of an extensive NMR study, MS data, and chemical reaction. The ability of these compounds to act as antiinflammatory agents has been evaluated for the first time by in vivo tests on carrageenin-induced rat paw edema, an experimental model of acute inflammation. Comparison of the bioactivity of pepluanone and compound 2 in terms of chemical structure, evidenced the high efficiency of pepluanone and the absence of appreciable activity for compound 2, thus giving a first insight into the structure−activity relationship. Further in vitro experiments performed on pepluanone let us hypothesize that its activity could be explained in reducing the production of nitric oxide, prostaglandin E2, and TNF-α by inhibiting the expression of inducible nitric oxide synthase, cyclooxygenase-2, and TNF-α mRNA through the down-regulation of NF-κB binding activity.

KW - antiinflammatory agents

KW - pharmacy

KW - medicine

UR - http://dx.doi.org/10.1021/jm050321r

U2 - 10.1021/jm050321r

DO - 10.1021/jm050321r

M3 - Article

VL - 48

SP - 7055

EP - 7062

JO - Journal of Medicinal Chemistry

T2 - Journal of Medicinal Chemistry

JF - Journal of Medicinal Chemistry

SN - 0022-2623

IS - 22

ER -