Search

Your search keyword '"Yann Fromentin"' showing total 5 results
Start Over Author "Yann Fromentin" Topic biology.organism_classification
5 results on '"Yann Fromentin"'

1. Biotransformation of guttiferones, Symphonia globulifera metabolites, by Bipolaris cactivora , an endophytic fungus isolated from its leaves

Author

Pauline Menelle, Didier Buisson, Yann Fromentin, Kevin Cottet, Marie-Christine Lallemand, Jérôme Quintin, Joëlle Dupont, Cibles Thérapeutiques et conception de médicaments (CiTCoM - UMR 8038), Institut de Chimie du CNRS (INC)-Centre National de la Recherche Scientifique (CNRS)-Université de Paris (UP), Molécules de Communication et Adaptation des Micro-organismes (MCAM), Muséum national d'Histoire naturelle (MNHN)-Centre National de la Recherche Scientifique (CNRS), Centre d'Etudes et de Recherche sur le Médicament de Normandie (CERMN), Université de Caen Normandie (UNICAEN), Normandie Université (NU)-Normandie Université (NU), Institut de Systématique, Evolution, Biodiversité (ISYEB ), Muséum national d'Histoire naturelle (MNHN)-École pratique des hautes études (EPHE), and Université Paris sciences et lettres (PSL)-Université Paris sciences et lettres (PSL)-Sorbonne Université (SU)-Centre National de la Recherche Scientifique (CNRS)-Université des Antilles (UA)

Subjects
0303 health sciences, [SDV.BIO]Life Sciences [q-bio]/Biotechnology, biology, 010405 organic chemistry, Chemistry, Microorganism, Organic Chemistry, [CHIM.THER]Chemical Sciences/Medicinal Chemistry, Endophytic fungus, biology.organism_classification, 01 natural sciences, Biochemistry, Plant use of endophytic fungi in defense, 0104 chemical sciences, 03 medical and health sciences, chemistry.chemical_compound, Bipolaris cactivora, Biotransformation, Xanthone, Botany, Physical and Theoretical Chemistry, Symphonia globulifera, [SDV.MP.MYC]Life Sciences [q-bio]/Microbiology and Parasitology/Mycology, 030304 developmental biology
Abstract

International audience; The search for active microorganisms for the biotransformation of guttiferone A (1) and C (6) has been successfully undertaken from a collection of endophytic fungi of Symphonia globulifera. Of the twenty-five isolates obtained from the leaves, three are active and have been identified as Bipolaris cactivora. The products obtained are the result of xanthone cyclisation with the formation of two regioisomers among four possible and corresponding to 1,16-oxy-guttiferone and 3,16-oxy-guttiferone. The biotransformation conditions were studied. Interestingly, both oxy-guttiferones A are present in the plant, and the ratio of 3,16-oxy-guttiferone to 1,16-oxy-guttiferone is 4 : 1, very close to that observed by biotransformation (3.8 : 1). These results are consistent with the involvement of endophytes in their formation pathway from guttiferone A, in planta. Finally, biotransformation made it possible to obtain and describe for the first time oxy-guttiferones C.

Published
2021
Full Text
View/download PDF

2. Progress on PPAPs cyclization: Guttiferone A as a case study

Author

Marie-Christine Lallemand, Thomas Gaslonde, Yann Fromentin, François-Hugues Porée, Didier Buisson, Kevin Cottet, Pauline Menelle, Equipe Pharmacognosie (UMR 8638), Chimie Organique, Médicinale et Extractive et Toxicologie Expérimentale (COMETE - UMR 8638), Université Paris Descartes - Paris 5 (UPD5)-Centre National de la Recherche Scientifique (CNRS)-Université Paris Descartes - Paris 5 (UPD5)-Centre National de la Recherche Scientifique (CNRS), Synthèse et structure de molécules d'interet pharmacologique (SSMIP), Université Paris Descartes - Paris 5 (UPD5)-Centre National de la Recherche Scientifique (CNRS), Laboratoire de Chimie et de Biochimie Pharmacologiques et Toxicologiques (LCBPT - UMR 8601), Université Paris Descartes - Paris 5 (UPD5)-Institut de Chimie du CNRS (INC)-Centre National de la Recherche Scientifique (CNRS)-Université Paris Descartes - Paris 5 (UPD5)-Institut de Chimie du CNRS (INC)-Centre National de la Recherche Scientifique (CNRS), Université Paris Descartes - Paris 5 (UPD5)-Centre National de la Recherche Scientifique (CNRS)-Institut de Chimie du CNRS (INC), Centre National de la Recherche Scientifique (CNRS)-Institut de Chimie du CNRS (INC)-Université Paris Descartes - Paris 5 (UPD5)-Centre National de la Recherche Scientifique (CNRS)-Institut de Chimie du CNRS (INC)-Université Paris Descartes - Paris 5 (UPD5), and Université Paris Descartes - Paris 5 (UPD5)-Institut de Chimie du CNRS (INC)-Centre National de la Recherche Scientifique (CNRS)

Subjects
biology, 010405 organic chemistry, Chemistry, Stereochemistry, Antiparasitic, medicine.drug_class, [CHIM.ORGA]Chemical Sciences/Organic chemistry, Organic Chemistry, 010402 general chemistry, biology.organism_classification, 01 natural sciences, Biochemistry, 0104 chemical sciences, 3. Good health, Drug Discovery, medicine, Organic chemistry, Symphonia globulifera, ComputingMilieux_MISCELLANEOUS
Abstract

Guttiferone A and cyclized analogs are naturally occurring polycyclic polyprenylated acyl phloroglucinols possessing antiparasitic activities. Naturally occurring xanthones possess increased activity, but are either rare or difficult to synthesize. In this paper, three optimized methodologies to access natural, hydroxylated and non-natural xanthonic skeletons from guttiferone A are described. These compounds will serve as starting materials for further SAR studies.

Published
2017
Full Text
View/download PDF

3. Isolation of Guttiferones from Renewable Parts of Symphonia globulifera by Centrifugal Partition Chromatography

Author

Marie-Christine Lallemand, Yann Fromentin, Christophe Duplais, Raphaël Grougnet, Guillaume Odonne, Marina Kritsanida, Kevin Cottet, Sylvie Michel, Equipe Pharmacognosie (UMR 8638), Chimie Organique, Médicinale et Extractive et Toxicologie Expérimentale (COMETE - UMR 8638), Centre National de la Recherche Scientifique (CNRS)-Institut de Chimie du CNRS (INC)-Université Paris Descartes - Paris 5 (UPD5)-Centre National de la Recherche Scientifique (CNRS)-Institut de Chimie du CNRS (INC)-Université Paris Descartes - Paris 5 (UPD5), Centre National de la Recherche Scientifique (CNRS)-Institut de Chimie du CNRS (INC)-Université Paris Descartes - Paris 5 (UPD5), USR 3456 Ethnoecologie et dynamiques culturelles, Centre National de la Recherche Scientifique (CNRS), Ecologie des forêts de Guyane (UMR ECOFOG), Centre de Coopération Internationale en Recherche Agronomique pour le Développement (Cirad)-Institut National de la Recherche Agronomique (INRA)-AgroParisTech-Université de Guyane (UG)-Centre National de la Recherche Scientifique (CNRS)-Université des Antilles (UA), Université Paris Descartes - Paris 5 (UPD5)-Centre National de la Recherche Scientifique (CNRS)-Université Paris Descartes - Paris 5 (UPD5)-Centre National de la Recherche Scientifique (CNRS), and Université Paris Descartes - Paris 5 (UPD5)-Centre National de la Recherche Scientifique (CNRS)

Subjects
Centrifugal partition chromatography, Ethyl acetate, Pharmaceutical Science, Analytical Chemistry, Benzophenones, chemistry.chemical_compound, [CHIM.ANAL]Chemical Sciences/Analytical chemistry, Clusiaceae, Drug Discovery, Centrifugation, Density Gradient, Organic chemistry, Symphonia globulifera, Chromatography, High Pressure Liquid, ComputingMilieux_MISCELLANEOUS, Pharmacology, Solvent system, Chromatography, Molecular Structure, biology, Chemistry, Organic Chemistry, biology.organism_classification, Complementary and alternative medicine, Molecular Medicine, Methanol
Abstract

The aim of this study was to investigate the species Symphonia globulifera , a source of polycyclic polyprenylated acyl phloroglucinols such as guttiferone A, which is known to exhibit a variety of biological activities including noticeable antileishmanial properties. Our goal was the identification and the quantification of guttiferone A in different renewable parts of S. globulifera and its preparative isolation. To the best of our knowledge, there is no data concerning its mechanism of action. Consequently, it is particularly interesting to isolate it in gram quantities in order to establish structure activity relationship studies. After performing high-performance liquid chromatography profiles detecting the presence of guttiferone A and proceeding to its quantification, a centrifugal partition chromatography methodology using a two-phase solvent system of cyclohexane/ethyl acetate/methanol/water (20 : 1 : 20 : 1, v/v/v/v) was applied to each extract. In conclusion, a centrifugal partition chromatography system has been developed to ensure a fast, reliable, and scalable way to isolate, with a high level of purity, guttiferone A from five renewable parts of S. globulifera . Moreover, this methodology can be extended to the isolation of other polycyclic polyprenylated acyl phloroglucinols such as guttiferones B, C, and D.

Published
2015
Full Text
View/download PDF

4. Comparative LC–MS-based metabolite profiling of the ancient tropical rainforest tree Symphonia globulifera

Author

Christophe Duplais, Olivier Laprévote, Marie-Christine Lallemand, Guillaume Odonne, Sylvie Michel, Kevin Cottet, Yann Fromentin, Grégory Genta-Jouve, Equipe Pharmacognosie (UMR 8638), Chimie Organique, Médicinale et Extractive et Toxicologie Expérimentale (COMETE - UMR 8638), Université Paris Descartes - Paris 5 (UPD5)-Centre National de la Recherche Scientifique (CNRS)-Université Paris Descartes - Paris 5 (UPD5)-Centre National de la Recherche Scientifique (CNRS), USR 3456 Ethnoecologie et dynamiques culturelles, Centre National de la Recherche Scientifique (CNRS), Ecologie des forêts de Guyane (UMR ECOFOG), Centre de Coopération Internationale en Recherche Agronomique pour le Développement (Cirad)-Institut National de la Recherche Agronomique (INRA)-AgroParisTech-Université de Guyane (UG)-Centre National de la Recherche Scientifique (CNRS)-Université des Antilles (UA), Institut de Chimie des Substances Naturelles (ICSN), Université Paris Descartes - Paris 5 (UPD5)-Institut de Chimie du CNRS (INC)-Centre National de la Recherche Scientifique (CNRS)-Université Paris Descartes - Paris 5 (UPD5)-Institut de Chimie du CNRS (INC)-Centre National de la Recherche Scientifique (CNRS), Centre National de la Recherche Scientifique (CNRS)-Institut de Chimie du CNRS (INC), and Université des Antilles (UA)-Université de Guyane (UG)-Centre National de la Recherche Scientifique (CNRS)-AgroParisTech-Centre de Coopération Internationale en Recherche Agronomique pour le Développement (Cirad)-Institut National de la Recherche Agronomique (INRA)

Subjects
Rainforest, Databases, Factual, Antiparasitic, medicine.drug_class, Xanthones, Plasmodium falciparum, Trypanosoma brucei brucei, Plant Science, Flowers, Horticulture, Trypanosoma brucei, Biochemistry, Plant Roots, Benzophenones, Metabolomics, Clusiaceae, parasitic diseases, Botany, medicine, Symphonia globulifera, Molecular Biology, ComputingMilieux_MISCELLANEOUS, biology, Molecular Structure, General Medicine, 15. Life on land, biology.organism_classification, French Guiana, [SDV.BV.PEP]Life Sciences [q-bio]/Vegetal Biology/Phytopathology and phytopharmacy, Plant Leaves, Phytochemical, Seeds, Plant Bark, Tropical rainforest
Abstract

In the last few years, several phytochemical studies have been undertaken on the tropical tree Symphonia globulifera leading to the isolation and characterisation of several compounds exhibiting antiparasitic activities against Plasmodium falciparum, Trypanosoma brucei and Leishmania donovani. The comparative LC-MS based metabolite profiling study conducted on the tree led to the identification of compounds originating from specific tissues. The results showed that renewable organs/tissues can be used as the starting material for the production of polycyclic poly-prenylated-acylphloroglucinols, therefore reducing impacts on biodiversity. This study also underlined the lack of knowledge on the secondary metabolites produced by S. globulifera since only a small number of the total detected features were putatively identified using the database of known compounds for the species.

Published
2014
Full Text
View/download PDF

5. Synthesis of novel guttiferone A derivatives: In-vitro evaluation toward Plasmodium falciparum, Trypanosoma brucei and Leishmania donovani

Author

Marie-Christine Lallemand, Philippe M. Loiseau, Philippe Grellier, Bruno Ndjakou Lenta, Sylvie Michel, Didier Buisson, Yann Fromentin, Jean Duplex Wansi, Elisabeth Mouray, Nicolas Gaboriaud-Kolar, Equipe Pharmacognosie (UMR 8638), Chimie Organique, Médicinale et Extractive et Toxicologie Expérimentale (COMETE - UMR 8638), Université Paris Descartes - Paris 5 (UPD5)-Centre National de la Recherche Scientifique (CNRS)-Université Paris Descartes - Paris 5 (UPD5)-Centre National de la Recherche Scientifique (CNRS), Université Paris Descartes - Paris 5 (UPD5), Université Sorbonne Paris Cité (USPC), Molécules de Communication et Adaptation des Micro-organismes (MCAM), Muséum national d'Histoire naturelle (MNHN)-Centre National de la Recherche Scientifique (CNRS), Laboratoire de Chimie et Biochimie des Substances Naturelles, Centre National de la Recherche Scientifique (CNRS), Université Paris Descartes - Paris 5 (UPD5)-Institut de Chimie du CNRS (INC)-Centre National de la Recherche Scientifique (CNRS)-Université Paris Descartes - Paris 5 (UPD5)-Institut de Chimie du CNRS (INC)-Centre National de la Recherche Scientifique (CNRS), Université Paris Descartes - Paris 5 (UPD5)-Institut de Chimie du CNRS (INC)-Centre National de la Recherche Scientifique (CNRS), Université Paris Descartes - Paris 5 (UPD5)-Centre National de la Recherche Scientifique (CNRS), Laboratoire de chimie et biochimie des substances naturelles, and Centre National de la Recherche Scientifique (CNRS)-Muséum national d'Histoire naturelle (MNHN)

Subjects
Antiparasitic, medicine.drug_class, Stereochemistry, [SDV]Life Sciences [q-bio], Plasmodium falciparum, Trypanosoma brucei brucei, Antiprotozoal Agents, Leishmania donovani, Trypanosoma brucei, 01 natural sciences, Benzophenones, Structure-Activity Relationship, 03 medical and health sciences, chemistry.chemical_compound, Parasitic Sensitivity Tests, Clusiaceae, parasitic diseases, Drug Discovery, medicine, [CHIM]Chemical Sciences, Symphonia globulifera, ComputingMilieux_MISCELLANEOUS, 030304 developmental biology, Pharmacology, 0303 health sciences, Natural product, Dose-Response Relationship, Drug, Molecular Structure, biology, 010405 organic chemistry, Chemistry, Organic Chemistry, General Medicine, biology.organism_classification, Semisynthesis, In vitro, 0104 chemical sciences, 3. Good health, [SDV.MP]Life Sciences [q-bio]/Microbiology and Parasitology, Biochemistry, Seeds
Abstract

The catechol pharmacomodulation of the natural product guttiferone A, isolated from the Symphonia globulifera tree, led to the semisynthesis of a collection of twenty derivatives. The ester and ether derivatives of guttiferone A were evaluated for their anti-plasmodial, trypanocidal and anti-leishmanial activities. Some compounds described below have shown potent antiparasitic activity against Plasmodium falciparum, Trypanosoma brucei and Leishmania donovani in a range from 1 to 5 μM. The evaluation of guttiferone A derivatives against VERO cells highlighted catechol modulations as an interesting tool to decrease the toxicity and keep the activity of this natural compound. The current study revealed new molecules as promising new antiparasitic drug candidates.

Published
2013
Full Text
View/download PDF

Catalog

Books, media, physical & digital resources
See catalog results