Total Synthesis of (+)-Penicyclone A and Evaluation of Biological Activity Including Intermediate Compounds

Duvnjak, Mirko; Talajić, Gregor; Baranašić, Jurica; Baus Topić, Nea; Čipčić Paljetak, Hana; Cindro, Nikola (2025) Total Synthesis of (+)-Penicyclone A and Evaluation of Biological Activity Including Intermediate Compounds. International Journal of Molecular Sciences, 26 (14). ISSN 1422-0067

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Abstract

Penicyclone A is a polyketide compound with a unique and intriguing structure recently isolated from the fungus Penicillium sp. F23-2 during an OSMAC (one-strain-many-compounds) campaign. The compound demonstrated significant antimicrobial activity without exhibiting any cytotoxic effects, which prompted us to pursue total synthesis of the reported enantiomer. Upon completion of the synthesis, we observed that our synthetic compound lacked antimicrobial activity. Further analysis suggested that the natural product may have, in fact, been the opposite enantiomer to that reported. This observation led us to synthesize the antipodal enantiomer using our previously developed synthetic sequence and to evaluate the biological activity (via antibacterial and cytotoxicity assays) of both the final compound and the selected intermediates from both enantiomeric series.

Item Type:	Article
Uncontrolled Keywords:	double Grignard reaction; fungus metabolite; natural product; polyketide; total synthesis
Subjects:	NATURAL SCIENCES > Chemistry > Organic Chemistry
Divisions:	Division of Molecular Biology
Projects:	Project title Project leader Project code Project type Totalna sinteza bioaktivnih metabolita – Od dubokomorskih mikroorganizama do nove klase antibiotika i sintetskih metodologija (ToSiAn) Nikola Cindro NPOO.C3.2.R2-I1.06.0043 EK Mikroorganizmi kao izvor novih klasa antibiotika – Od totalne sinteze do novog kemijskog prostora i metodologije Nikola Cindro IP-2024-05-5352 HrZZ Razvoj karijera mladih istraživača - izobrazba novih doktora znanosti (NPOO-DOK-2023-10) na projektu ToSiAn Nikola Cindro NPOO-DOK-2023-10-ToSiAn EK
Depositing User:	Lorena Palameta
Date Deposited:	30 Jul 2025 08:02
URI:	http://fulir.irb.hr/id/eprint/9931
DOI:	10.3390/ijms26146643

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