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Papers by Emanuele Arlandini

Research paper thumbnail of Identification of New Diterpenoids from Euphorbia calyptrata Cell Cultures

Four new diterpenoids, helioscopinolides F (2), H (4), I (5), and L (6), were isolated from three... more Four new diterpenoids, helioscopinolides F (2), H (4), I (5), and L (6), were isolated from three different cultured cell lines of Euphorbia calyptrata var. involucrata. Helioscopinolide B (1) and jolkinolide E (3), previously found in Euphorbia helioscopia and Euphorbia jolkini, respectively, were also isolated from the same cultures. Structures were identified by spectroscopic methods.

Research paper thumbnail of An Easy Entry to (1S, 2S) and (1R, 2R)- Threo -Ifenprodil

Synthetic Communications, 2000

ABSTRACT

Research paper thumbnail of Acrolein sequestering ability of the endogenous tripeptide glycyl-histidyl-lysine (GHK): Characterization of conjugation products by ESI-MSn and theoretical calculations

Journal of Pharmaceutical and Biomedical Analysis, 2008

Acrolein (ACR) is a well-known carbonyl toxin produced by lipid peroxidation of polyunsaturated f... more Acrolein (ACR) is a well-known carbonyl toxin produced by lipid peroxidation of polyunsaturated fatty acids, which is involved in several life-threatening pathologies such as Alzheimer disease, arteriosclerosis, diabetes, and nephropathy. The aim of this work was to study the quenching ability of the endogenous tripeptide glycyl-histidyl-lysine (GHK), a liver cell growth factor isolated from human plasma, towards the electrophilic aldehyde ACR and to characterize the reaction products by electrospray mass spectrometry (ESI-MS/MS infusion experiments; positive ion mode). The reaction of ACR (30 microM) with GHK (0.1, 0.25, 0.5, 1.0 mM) was followed by measuring aldehyde consumption by reverse-phase HPLC (phosphate buffer, pH 7.4); after 4h, when the aldehyde had completely disappeared; the reaction products were checked by ESI-MS/MS. Several products were detected in the GHK+ACR reaction (1:1). This indicates a complex reaction cascade involving the sequential addition of ACR (up to 3 mol) to the tripeptide GHK and, in particular, to the epsilon-amino group of the lysine residue and to the N(tau) and N(pi) of the histidine moiety. The Michael addition of two molecules of ACR to the epsilon-amino group of the lysine residue is followed by aldol condensation and dehydration to give the N-(3-formyl-3,4-dehydropiperidino) derivative. The results confirm that the ESI-MS/MS approach in a direct infusion experiment permits rapid profiling of the products of the GHK+ACR reaction. They firstly point to the potential medicinal use of GHK in the prevention of carbonyl stress-linked pathologies, and--second--help shed light on the physiological role of this histidine-containing tripeptide which is claimed to be an endogenous growth factor, but has never been shown to be an ACR quencher.

Research paper thumbnail of Structure Elucidation of Helioscopinolides D and E from Euphorbia calyptrata Cell Cultures

Journal of Natural Products, 1991

... DANIELA BORGHI,~ LUCA BAUMER, MARZIA BALLABIO, EMANUELE ARLANDINI, RID Analytical Chemistry N... more ... DANIELA BORGHI,~ LUCA BAUMER, MARZIA BALLABIO, EMANUELE ARLANDINI, RID Analytical Chemistry NICOLEITA CRESPI PERELLINO, RID Biotecbnology, Fannitalia C Erba, Erbamnt Group ... Y. Shizuri, S. Kosemura, S. Yamamura, S. Ohba, M. Ito, and Y. Saito, Chem. ...

Research paper thumbnail of Identification of New Diterpenoids from Euphorbia calyptrata Cell Cultures

Journal of Natural Products, 1996

Four new diterpenoids, helioscopinolides F (2), H (4), I (5), and L (6), were isolated from three... more Four new diterpenoids, helioscopinolides F (2), H (4), I (5), and L (6), were isolated from three different cultured cell lines of Euphorbia calyptrata var. involucrata. Helioscopinolide B (1) and jolkinolide E (3), previously found in Euphorbia helioscopia and Euphorbia jolkini, respectively, were also isolated from the same cultures. Structures were identified by spectroscopic methods.

Research paper thumbnail of Unexpected Reaction between DCC and Cephalosporanic Acid Sulphones

Research paper thumbnail of D1 Agonist and/or D2 antagonist dopamine receptor properties of a series of ergoline derivatives: a structure–activity study

European Journal of Medicinal Chemistry, 1999

A series of (3,5-dioxopiperazin-1-yl)ergoline derivatives has been synthesised and evaluated in v... more A series of (3,5-dioxopiperazin-1-yl)ergoline derivatives has been synthesised and evaluated in vitro and in vivo for their dopaminergic D 1 and D 2 components. The structural contributions to the pharmacological profile of the ergoline skeleton, its substituents on positions 1, 2, 6, 9, and the 3,5-dioxopiperazin-1-yl portion of the molecule were examined. Structure-activity relationships within this series suggested that substitution on the ergoline skeleton in position 1 or 2 and on the 3,5-dioxopiperazin-4-nitrogen generated compounds with a spectrum of dopamine agonistic/antagonistic activity sensitive to both the nature and position of substituents. © Elsevier, Paris ergoline derivatives / structure-affinity relationship / dopaminergic / antidopaminergic activity

Research paper thumbnail of Identification of New Diterpenoids from Euphorbia calyptrata Cell Cultures

Four new diterpenoids, helioscopinolides F (2), H (4), I (5), and L (6), were isolated from three... more Four new diterpenoids, helioscopinolides F (2), H (4), I (5), and L (6), were isolated from three different cultured cell lines of Euphorbia calyptrata var. involucrata. Helioscopinolide B (1) and jolkinolide E (3), previously found in Euphorbia helioscopia and Euphorbia jolkini, respectively, were also isolated from the same cultures. Structures were identified by spectroscopic methods.

Research paper thumbnail of An Easy Entry to (1S, 2S) and (1R, 2R)- Threo -Ifenprodil

Synthetic Communications, 2000

ABSTRACT

Research paper thumbnail of Acrolein sequestering ability of the endogenous tripeptide glycyl-histidyl-lysine (GHK): Characterization of conjugation products by ESI-MSn and theoretical calculations

Journal of Pharmaceutical and Biomedical Analysis, 2008

Acrolein (ACR) is a well-known carbonyl toxin produced by lipid peroxidation of polyunsaturated f... more Acrolein (ACR) is a well-known carbonyl toxin produced by lipid peroxidation of polyunsaturated fatty acids, which is involved in several life-threatening pathologies such as Alzheimer disease, arteriosclerosis, diabetes, and nephropathy. The aim of this work was to study the quenching ability of the endogenous tripeptide glycyl-histidyl-lysine (GHK), a liver cell growth factor isolated from human plasma, towards the electrophilic aldehyde ACR and to characterize the reaction products by electrospray mass spectrometry (ESI-MS/MS infusion experiments; positive ion mode). The reaction of ACR (30 microM) with GHK (0.1, 0.25, 0.5, 1.0 mM) was followed by measuring aldehyde consumption by reverse-phase HPLC (phosphate buffer, pH 7.4); after 4h, when the aldehyde had completely disappeared; the reaction products were checked by ESI-MS/MS. Several products were detected in the GHK+ACR reaction (1:1). This indicates a complex reaction cascade involving the sequential addition of ACR (up to 3 mol) to the tripeptide GHK and, in particular, to the epsilon-amino group of the lysine residue and to the N(tau) and N(pi) of the histidine moiety. The Michael addition of two molecules of ACR to the epsilon-amino group of the lysine residue is followed by aldol condensation and dehydration to give the N-(3-formyl-3,4-dehydropiperidino) derivative. The results confirm that the ESI-MS/MS approach in a direct infusion experiment permits rapid profiling of the products of the GHK+ACR reaction. They firstly point to the potential medicinal use of GHK in the prevention of carbonyl stress-linked pathologies, and--second--help shed light on the physiological role of this histidine-containing tripeptide which is claimed to be an endogenous growth factor, but has never been shown to be an ACR quencher.

Research paper thumbnail of Structure Elucidation of Helioscopinolides D and E from Euphorbia calyptrata Cell Cultures

Journal of Natural Products, 1991

... DANIELA BORGHI,~ LUCA BAUMER, MARZIA BALLABIO, EMANUELE ARLANDINI, RID Analytical Chemistry N... more ... DANIELA BORGHI,~ LUCA BAUMER, MARZIA BALLABIO, EMANUELE ARLANDINI, RID Analytical Chemistry NICOLEITA CRESPI PERELLINO, RID Biotecbnology, Fannitalia C Erba, Erbamnt Group ... Y. Shizuri, S. Kosemura, S. Yamamura, S. Ohba, M. Ito, and Y. Saito, Chem. ...

Research paper thumbnail of Identification of New Diterpenoids from Euphorbia calyptrata Cell Cultures

Journal of Natural Products, 1996

Four new diterpenoids, helioscopinolides F (2), H (4), I (5), and L (6), were isolated from three... more Four new diterpenoids, helioscopinolides F (2), H (4), I (5), and L (6), were isolated from three different cultured cell lines of Euphorbia calyptrata var. involucrata. Helioscopinolide B (1) and jolkinolide E (3), previously found in Euphorbia helioscopia and Euphorbia jolkini, respectively, were also isolated from the same cultures. Structures were identified by spectroscopic methods.

Research paper thumbnail of Unexpected Reaction between DCC and Cephalosporanic Acid Sulphones

Research paper thumbnail of D1 Agonist and/or D2 antagonist dopamine receptor properties of a series of ergoline derivatives: a structure–activity study

European Journal of Medicinal Chemistry, 1999

A series of (3,5-dioxopiperazin-1-yl)ergoline derivatives has been synthesised and evaluated in v... more A series of (3,5-dioxopiperazin-1-yl)ergoline derivatives has been synthesised and evaluated in vitro and in vivo for their dopaminergic D 1 and D 2 components. The structural contributions to the pharmacological profile of the ergoline skeleton, its substituents on positions 1, 2, 6, 9, and the 3,5-dioxopiperazin-1-yl portion of the molecule were examined. Structure-activity relationships within this series suggested that substitution on the ergoline skeleton in position 1 or 2 and on the 3,5-dioxopiperazin-4-nitrogen generated compounds with a spectrum of dopamine agonistic/antagonistic activity sensitive to both the nature and position of substituents. © Elsevier, Paris ergoline derivatives / structure-affinity relationship / dopaminergic / antidopaminergic activity