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- Title
Nature‐Inspired Chemistry of Complex Alkaloids: Combining Targeted Molecular Networking Approach and Semisynthetic Strategy to Access Rare Communesins in a Marine‐Derived Penicillium expansum.
- Authors
Hoang, Thi Phuong Thuy; Roullier, Catherine; Evanno, Laurent; Kerzaon, Isabelle; Gentil, Emmanuel; Robiou du Pont, Thibaut; Nazih, El‐Hassane; Pouchus, Yves François; Bertrand, Samuel; Poupon, Erwan; Grovel, Olivier
- 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.
- Subjects
COMPLEX compounds; APPLE blue mold; NATURAL products; STRUCTURE-activity relationships; ALKALOIDS; CELL lines; NEW product development
- Publication
Chemistry - A European Journal, 2023, Vol 29, Issue 38, p1
- ISSN
0947-6539
- Publication type
Article
- DOI
10.1002/chem.202300103