Joël Doussot | Cnam Paris (original) (raw)

Papers by Joël Doussot

Research paper thumbnail of Development and validation of an efficient ultrasound assisted extraction of phenolic compounds from flax (Linum usitatissimum L.) seeds

Ultrasonics Sonochemistry, 2015

Research paper thumbnail of ChemInform Abstract: Regio- and Stereoselective Cyanation of Aromatic Steroids in the 9. alpha.- and 12α-Position by DDQ-TMSCN

ChemInform

ChemInform is a weekly Abstracting Service, delivering concise information at a glance that was e... more ChemInform is a weekly Abstracting Service, delivering concise information at a glance that was extracted from about 100 leading journals. To access a ChemInform Abstract of an article which was published elsewhere, please select a “Full Text” option. The original article is trackable via the “References” option.

Research paper thumbnail of ChemInform Abstract: Stereoselective Synthesis of 12α-Amino- and 12α- Aminomethyl 19-Norsteroids

ChemInform

ChemInform is a weekly Abstracting Service, delivering concise information at a glance that was e... more ChemInform is a weekly Abstracting Service, delivering concise information at a glance that was extracted from about 100 leading journals. To access a ChemInform Abstract of an article which was published elsewhere, please select a “Full Text” option. The original article is trackable via the “References” option.

Research paper thumbnail of ChemInform Abstract: Selective Opening of Substituted Styrenic Epoxides by Lithium Azide in the Presence of β-Cyclodextrin

ChemInform, 1995

ABSTRACT ChemInform is a weekly Abstracting Service, delivering concise information at a glance t... more ABSTRACT ChemInform is a weekly Abstracting Service, delivering concise information at a glance that was extracted from about 100 leading journals. To access a ChemInform Abstract of an article which was published elsewhere, please select a “Full Text” option. The original article is trackable via the “References” option.

Research paper thumbnail of ChemInform Abstract: Regio- and Stereoselective Opening of Phenyloxirane by Lithium Azide: A Direct Access to 2-Azido-1-phenylethanol

Research paper thumbnail of Kinetics of glucosylated and non-glucosylated aryltetralin lignans in Linum hairy root cultures

Phytochemistry, 2015

Due to their pronounced cytotoxic activity, a number of aryltetralin lignans (ATLs), such as podo... more Due to their pronounced cytotoxic activity, a number of aryltetralin lignans (ATLs), such as podophyllotoxin (PTOX), are used as antitumor compounds. The production of such molecules from entire plants or plant cell-tissue-organ cultures is thus of interest to the pharmaceutical industry. Hairy root cultures constitute a good tool not only for phytochemical production but also for investigating plant secondary metabolism. This work reports on the growth and ATL biosynthesis in two hairy root cultures of Linum album Kotschy ex Boiss. and Linum flavum. The kinetics of accumulation of the intermediates of MPTOX biosynthesis and of their glucosylated forms are described over a 21-day period of growth. An accumulation of non-glucosylated forms of the ATLs during the exponential phase of the cultures is followed by an accumulation of the glucosylated forms during the stationary phase. Our results show a strong coordination of the biosynthetic paths derived from deoxypodophyllotoxin via deoxypodophyllotoxin 6-hydroxylase and deoxypodophyllotoxin 7-hydroxylase, and a coordinated glucosylation of podophyllotoxin, methoxypodophyllotoxin, and 5'-demethoxymethoxypodophyllotoxin. Furthermore, our results suggest an important role of β-peltatin-6-glucoside formation in the control of ATL accumulation in Linum hairy root cultures.

Research paper thumbnail of ChemInform Abstract: Efficient Kinetic Resolution of Racemic 2-Nitro-cyclopent(or hex)-2-en-1-yl Acetates

Research paper thumbnail of Efficient kinetic resolution of racemic 3-nitro-cyclopent(or hex)-2-en-1-yl acetates

Tetrahedron: Asymmetry, 2000

Research paper thumbnail of Development and validation of an efficient ultrasound assisted extraction of phenolic compounds from flax (Linum usitatissimum L.) seeds

Ultrasonics Sonochemistry, 2015

Research paper thumbnail of ChemInform Abstract: Selective Synthesis of 1,1′-Binaphthalene Derivatives by Oxidative Coupling with TiCl4

ChemInform, 2000

ABSTRACT ChemInform is a weekly Abstracting Service, delivering concise information at a glance t... more ABSTRACT ChemInform is a weekly Abstracting Service, delivering concise information at a glance that was extracted from about 100 leading journals. To access a ChemInform Abstract of an article which was published elsewhere, please select a “Full Text” option. The original article is trackable via the “References” option.

Research paper thumbnail of Selective ring-opening reaction of styrene oxide with lithium azide in the presence of cyclodextrins in aqueous media

Tetrahedron: Asymmetry, 1992

Research paper thumbnail of Cisoid conjugated dithienylene compounds as precursors for electropolymerisation

Tetrahedron Letters, 1999

Research paper thumbnail of Selective synthesis of 1,1′-binaphthalene derivatives by oxidative coupling with TiCl4

Tetrahedron Letters, 2000

Research paper thumbnail of Regio- and Stereoselective Azidation of 19-Norsteroids

Research paper thumbnail of Selective Conversion of Benzylic C-H Bonds to an Amine Function by Oxidative Nucleophilic Substitution

Research paper thumbnail of Regio- and Stereoselective Cyanation of Aromatic Steroids in the 9α- and 12α-Position by DDQ-TMSCN

Research paper thumbnail of Regio- and Stereoselective Opening of Phenyloxirane by Lithium Azide: A Direct Access to 2-Azido-1-phenylethanol

Research paper thumbnail of Differential accumulation of monolignol-derived compounds in elicited flax (Linum usitatissimum) cell suspension cultures

Research paper thumbnail of 1 H and 13 C NMR study of a series of C-9-substituted 19-norsteroids

Journal of Physical Organic Chemistry, 2002

ABSTRACT The 1H and 13C NMR spectra of a series of 9-substituted 19-norsteroids were completely a... more ABSTRACT The 1H and 13C NMR spectra of a series of 9-substituted 19-norsteroids were completely assigned using a series of 2D NMR experiments, which included 1H–1H COSY, NOESY and 1H–13C heteronuclear HETCOR and HMQC. For second-order spin systems, chemical shifts and coupling constants were obtained by simulation of the experimental spectrum. Criteria were deduced to characterize the stereochemistry of these different compounds (multiplet pattern of H-8β and variation of chemical shifts). The results allow the easy determination of the configuration at C-9. Conformational changes resulting from the substitution were studied by NMR and molecular modeling calculations (AM1). Copyright © 2001 John Wiley & Sons, Ltd.

Research paper thumbnail of Podophyllotoxin and Deoxypodophyllotoxin in Juniperus bermudiana and 12 Other Juniperus Species: Optimization of Extraction, Method Validation, and Quantification

Journal of Agricultural and Food Chemistry, 2011

The lignans podophyllotoxin and deoxypodophyllotoxin are secondary metabolites with potent pharma... more The lignans podophyllotoxin and deoxypodophyllotoxin are secondary metabolites with potent pharmaceutical applications in cancer therapy. However, the supply of podophyllotoxin from its current natural source, Podophyllum hexandrum, is becoming increasingly problematic, and alternative sources are therefore urgently needed. So far, podophyllotoxin and deoxypodophyllotoxin have been found in some Juniperus species, although at low levels in most cases. Moreover, extraction protocols deserve optimization. This study aimed at developing and validating an efficient extraction protocol of podophyllotoxin and deoxypodophyllotoxin from Juniperus species and applying it to 13 Juniperus species, among which some had never been previously analyzed. Juniperus bermudiana was used for the development and validation of an extraction protocol for podophyllotoxin and deoxypodophyllotoxin allowing extraction yields of up to 22.6 mg/g DW of podophyllotoxin and 4.4 mg/g DW deoxypodophyllotoxin, the highest values found in leaf extract of Juniperus. The optimized extraction protocol and HPLC separation from DAD or MS detections were established and validated to investigate podophyllotoxin and deoxypodophyllotoxin contents in aerial parts of 12 other Juniperus species. This allowed either higher yields to be obtained in some species reported to contain these two compounds or the occurrence of these compounds in some other species to be reported for the first time. This efficient protocol allows effective extraction of podophyllotoxin and deoxypodophyllotoxin from aerial parts of Juniperus species, which could therefore constitute interesting alternative sources of these valuable metabolites.

Research paper thumbnail of Development and validation of an efficient ultrasound assisted extraction of phenolic compounds from flax (Linum usitatissimum L.) seeds

Ultrasonics Sonochemistry, 2015

Research paper thumbnail of ChemInform Abstract: Regio- and Stereoselective Cyanation of Aromatic Steroids in the 9. alpha.- and 12α-Position by DDQ-TMSCN

ChemInform

ChemInform is a weekly Abstracting Service, delivering concise information at a glance that was e... more ChemInform is a weekly Abstracting Service, delivering concise information at a glance that was extracted from about 100 leading journals. To access a ChemInform Abstract of an article which was published elsewhere, please select a “Full Text” option. The original article is trackable via the “References” option.

Research paper thumbnail of ChemInform Abstract: Stereoselective Synthesis of 12α-Amino- and 12α- Aminomethyl 19-Norsteroids

ChemInform

ChemInform is a weekly Abstracting Service, delivering concise information at a glance that was e... more ChemInform is a weekly Abstracting Service, delivering concise information at a glance that was extracted from about 100 leading journals. To access a ChemInform Abstract of an article which was published elsewhere, please select a “Full Text” option. The original article is trackable via the “References” option.

Research paper thumbnail of ChemInform Abstract: Selective Opening of Substituted Styrenic Epoxides by Lithium Azide in the Presence of β-Cyclodextrin

ChemInform, 1995

ABSTRACT ChemInform is a weekly Abstracting Service, delivering concise information at a glance t... more ABSTRACT ChemInform is a weekly Abstracting Service, delivering concise information at a glance that was extracted from about 100 leading journals. To access a ChemInform Abstract of an article which was published elsewhere, please select a “Full Text” option. The original article is trackable via the “References” option.

Research paper thumbnail of ChemInform Abstract: Regio- and Stereoselective Opening of Phenyloxirane by Lithium Azide: A Direct Access to 2-Azido-1-phenylethanol

Research paper thumbnail of Kinetics of glucosylated and non-glucosylated aryltetralin lignans in Linum hairy root cultures

Phytochemistry, 2015

Due to their pronounced cytotoxic activity, a number of aryltetralin lignans (ATLs), such as podo... more Due to their pronounced cytotoxic activity, a number of aryltetralin lignans (ATLs), such as podophyllotoxin (PTOX), are used as antitumor compounds. The production of such molecules from entire plants or plant cell-tissue-organ cultures is thus of interest to the pharmaceutical industry. Hairy root cultures constitute a good tool not only for phytochemical production but also for investigating plant secondary metabolism. This work reports on the growth and ATL biosynthesis in two hairy root cultures of Linum album Kotschy ex Boiss. and Linum flavum. The kinetics of accumulation of the intermediates of MPTOX biosynthesis and of their glucosylated forms are described over a 21-day period of growth. An accumulation of non-glucosylated forms of the ATLs during the exponential phase of the cultures is followed by an accumulation of the glucosylated forms during the stationary phase. Our results show a strong coordination of the biosynthetic paths derived from deoxypodophyllotoxin via deoxypodophyllotoxin 6-hydroxylase and deoxypodophyllotoxin 7-hydroxylase, and a coordinated glucosylation of podophyllotoxin, methoxypodophyllotoxin, and 5'-demethoxymethoxypodophyllotoxin. Furthermore, our results suggest an important role of β-peltatin-6-glucoside formation in the control of ATL accumulation in Linum hairy root cultures.

Research paper thumbnail of ChemInform Abstract: Efficient Kinetic Resolution of Racemic 2-Nitro-cyclopent(or hex)-2-en-1-yl Acetates

Research paper thumbnail of Efficient kinetic resolution of racemic 3-nitro-cyclopent(or hex)-2-en-1-yl acetates

Tetrahedron: Asymmetry, 2000

Research paper thumbnail of Development and validation of an efficient ultrasound assisted extraction of phenolic compounds from flax (Linum usitatissimum L.) seeds

Ultrasonics Sonochemistry, 2015

Research paper thumbnail of ChemInform Abstract: Selective Synthesis of 1,1′-Binaphthalene Derivatives by Oxidative Coupling with TiCl4

ChemInform, 2000

ABSTRACT ChemInform is a weekly Abstracting Service, delivering concise information at a glance t... more ABSTRACT ChemInform is a weekly Abstracting Service, delivering concise information at a glance that was extracted from about 100 leading journals. To access a ChemInform Abstract of an article which was published elsewhere, please select a “Full Text” option. The original article is trackable via the “References” option.

Research paper thumbnail of Selective ring-opening reaction of styrene oxide with lithium azide in the presence of cyclodextrins in aqueous media

Tetrahedron: Asymmetry, 1992

Research paper thumbnail of Cisoid conjugated dithienylene compounds as precursors for electropolymerisation

Tetrahedron Letters, 1999

Research paper thumbnail of Selective synthesis of 1,1′-binaphthalene derivatives by oxidative coupling with TiCl4

Tetrahedron Letters, 2000

Research paper thumbnail of Regio- and Stereoselective Azidation of 19-Norsteroids

Research paper thumbnail of Selective Conversion of Benzylic C-H Bonds to an Amine Function by Oxidative Nucleophilic Substitution

Research paper thumbnail of Regio- and Stereoselective Cyanation of Aromatic Steroids in the 9α- and 12α-Position by DDQ-TMSCN

Research paper thumbnail of Regio- and Stereoselective Opening of Phenyloxirane by Lithium Azide: A Direct Access to 2-Azido-1-phenylethanol

Research paper thumbnail of Differential accumulation of monolignol-derived compounds in elicited flax (Linum usitatissimum) cell suspension cultures

Research paper thumbnail of 1 H and 13 C NMR study of a series of C-9-substituted 19-norsteroids

Journal of Physical Organic Chemistry, 2002

ABSTRACT The 1H and 13C NMR spectra of a series of 9-substituted 19-norsteroids were completely a... more ABSTRACT The 1H and 13C NMR spectra of a series of 9-substituted 19-norsteroids were completely assigned using a series of 2D NMR experiments, which included 1H–1H COSY, NOESY and 1H–13C heteronuclear HETCOR and HMQC. For second-order spin systems, chemical shifts and coupling constants were obtained by simulation of the experimental spectrum. Criteria were deduced to characterize the stereochemistry of these different compounds (multiplet pattern of H-8β and variation of chemical shifts). The results allow the easy determination of the configuration at C-9. Conformational changes resulting from the substitution were studied by NMR and molecular modeling calculations (AM1). Copyright © 2001 John Wiley & Sons, Ltd.

Research paper thumbnail of Podophyllotoxin and Deoxypodophyllotoxin in Juniperus bermudiana and 12 Other Juniperus Species: Optimization of Extraction, Method Validation, and Quantification

Journal of Agricultural and Food Chemistry, 2011

The lignans podophyllotoxin and deoxypodophyllotoxin are secondary metabolites with potent pharma... more The lignans podophyllotoxin and deoxypodophyllotoxin are secondary metabolites with potent pharmaceutical applications in cancer therapy. However, the supply of podophyllotoxin from its current natural source, Podophyllum hexandrum, is becoming increasingly problematic, and alternative sources are therefore urgently needed. So far, podophyllotoxin and deoxypodophyllotoxin have been found in some Juniperus species, although at low levels in most cases. Moreover, extraction protocols deserve optimization. This study aimed at developing and validating an efficient extraction protocol of podophyllotoxin and deoxypodophyllotoxin from Juniperus species and applying it to 13 Juniperus species, among which some had never been previously analyzed. Juniperus bermudiana was used for the development and validation of an extraction protocol for podophyllotoxin and deoxypodophyllotoxin allowing extraction yields of up to 22.6 mg/g DW of podophyllotoxin and 4.4 mg/g DW deoxypodophyllotoxin, the highest values found in leaf extract of Juniperus. The optimized extraction protocol and HPLC separation from DAD or MS detections were established and validated to investigate podophyllotoxin and deoxypodophyllotoxin contents in aerial parts of 12 other Juniperus species. This allowed either higher yields to be obtained in some species reported to contain these two compounds or the occurrence of these compounds in some other species to be reported for the first time. This efficient protocol allows effective extraction of podophyllotoxin and deoxypodophyllotoxin from aerial parts of Juniperus species, which could therefore constitute interesting alternative sources of these valuable metabolites.