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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
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2. 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
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3. 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
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4. Acantholactone, a new manzamine related alkaloid with an unprecedented δ-lactone and ε-lactam ring system

Author

Yann Fromentin, Yike Zou, Amir E. Wahba, and Mark T. Hamann

Subjects
Circular dichroism, Molecular model, Chemistry, Stereochemistry, Alkaloid, Organic Chemistry, Absolute configuration, Ring (chemistry), Biochemistry, Article, chemistry.chemical_compound, Drug Discovery, Lactam, Two-dimensional nuclear magnetic resonance spectroscopy, δ lactone
Abstract

A new manzamine-related alkaloid with unprecedented δ-lactone and e-lactam rings called acantholactone (2), was isolated from the Indonesian sponge Acanthostrongylophora sp. The relative configuration of the two new ring systems was established through detailed analysis of NOESY correlations combined with molecular modeling studies. The absolute configuration of 2 was determined as 12S, 24R, 25R, 26R by comparing the computed electronic circular dichroism (ECD) spectra with experimental values.

Published
2013

5. Yeast-Mediated Xanthone Synthesis through Oxidative Intramolecular Cyclization

Author

Yann Fromentin, Marie-Christine Lallemand, Didier Buisson, Philippe Grellier, Jean Duplex Wansi, Molécules de Communication et Adaptation des Micro-organismes (MCAM), Muséum national d'Histoire naturelle (MNHN)-Centre National de la Recherche Scientifique (CNRS), and Grellier, Philippe

Subjects
Stereochemistry, Cell Survival, Xanthones, [SDV]Life Sciences [q-bio], Plasmodium falciparum, Trypanosoma brucei brucei, Oxidative phosphorylation, 010402 general chemistry, Norathyriol, 01 natural sciences, Biochemistry, chemistry.chemical_compound, Antimalarials, Biotransformation, Yeasts, Xanthone, [CHIM] Chemical Sciences, Chlorocebus aethiops, Animals, [CHIM]Chemical Sciences, Physical and Theoretical Chemistry, [SDV.MP] Life Sciences [q-bio]/Microbiology and Parasitology, Vero Cells, ComputingMilieux_MISCELLANEOUS, Molecular Structure, 010405 organic chemistry, Chemistry, Organic Chemistry, Intramolecular cyclization, Oxidation reduction, Yeast, 0104 chemical sciences, 3. Good health, [SDV] Life Sciences [q-bio], [SDV.MP]Life Sciences [q-bio]/Microbiology and Parasitology, Biocatalysis, Cyclization, Oxidation-Reduction
Abstract

Benzoylphloroglucinol derivatives are natural products showing diverse biological activities that could be modulated by structural modifications. For this purpose, we studied the biotransformation of guttiferone A and of maclurin using a combinatorial approach for screening active microorganism strains. We found a novel and unexpected yeast-catalyzed oxidation that has selectively given a new oxy-guttiferone A and norathyriol.

Published
2012

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