Nature‐Inspired Chemistry of Complex Alkaloids: Combining Targeted Molecular Networking Approach and Semisynthetic Strategy to Access Rare Communesins in a Marine‐Derived Penicillium expansum.
- Resource Type
- Article
- 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
- Source
- Chemistry - A European Journal. 7/6/2023, Vol. 29 Issue 38, p1-9. 9p.
- Subject
- *COMPLEX compounds
*APPLE blue mold
*NATURAL products
*STRUCTURE-activity relationships
*ALKALOIDS
*CELL lines
*NEW product development
- Language
- ISSN
- 0947-6539
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. [ABSTRACT FROM AUTHOR]