Nature‐Inspired Chemistry of Complex Alkaloids: Combining Targeted Molecular Networking Approach and Semisynthetic Strategy to Access Rare Communesins in a Marine‐Derived Penicillium expansum - Archive ouverte HAL Accéder directement au contenu
Article Dans Une Revue Chemistry - A European Journal Année : 2023

Nature‐Inspired Chemistry of Complex Alkaloids: Combining Targeted Molecular Networking Approach and Semisynthetic Strategy to Access Rare Communesins in a Marine‐Derived Penicillium expansum

Thi Phuong Thuy Hoang
  • Fonction : Auteur
Catherine Roullier
Laurent Evanno
Isabelle Kerzaon
Thibaut Robiou Du Pont
  • Fonction : Auteur
El‐hassane Nazih
  • Fonction : Auteur
Yves François Pouchus
Samuel Bertrand
Erwan Poupon
Olivier Grovel

Résumé

Abstract Communesins are rare alkaloids isolated from fungi of the genus Penicillium . In this work, the extract of a marine‐derived Penicillium expansum strain was studied using targeted molecular networking approach allowing to detect 65 communesins including 55 new ones. A fragmentation pattern for dimethylvinyl communesins was established and a script was implemented allowing to predict the structure and map all communesins in a global molecular network. A semisynthetic strategy was carried out to obtain some minor congeners from the two isolated communesins A and B. Nine communesins were then synthetised: two of them were already described as produced by the studied strain; four are new natural products which occurrence in the extracts was confirmed; three are new semi‐synthetic analogues never described so far. These communesins were evaluated for their cytotoxicity on two human cancer cell lines KB and MCF‐7 leading to a preliminary study of their structure‐activity relationships.

Dates et versions

hal-04485716 , version 1 (01-03-2024)

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Citer

Thi Phuong Thuy Hoang, Catherine Roullier, Laurent Evanno, Isabelle Kerzaon, Emmanuel Gentil, et al.. Nature‐Inspired Chemistry of Complex Alkaloids: Combining Targeted Molecular Networking Approach and Semisynthetic Strategy to Access Rare Communesins in a Marine‐Derived Penicillium expansum. Chemistry - A European Journal, 2023, 29 (38), ⟨10.1002/chem.202300103⟩. ⟨hal-04485716⟩
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