Penicillactonin and preaustinoid C, lactone-containing metabolites from a hot spring sediment Penicillium sp.

Raha Orfali, Shagufta Perveen, Jiangnan Peng, Ali S Alqahtani, Fahd A Nasr, Mohammad Z Ahmed, Paolo Luciano, Giuseppina Chianese, Areej M Al-Taweel, Orazio Taglialatela-Scafati

Journal: Fitoterapia 2022;163():105330

PMID: 36220499

Full Text on Elsevier Science View on PubMed

Abstract

Phytochemical investigation of Penicillium sp. RO-11 strain, collected from the sediments of a hydrothermal spring located in the southwestern area of Saudi Arabia, afforded, along with previously isolated compounds, the undescribed polyketides penicillactonin (1), penipyranicin D (4) and isopyrenulin B (5) and the undescribed meroterpenoid preaustinoid C (7). The structures of these compounds were elucidated based on data from mass spectrometry, 1D and 2D NMR, and comparison between experimental and calculated ECD spectra. Penicillactonin and preaustinoid C bring unprecedented structural features, for which a biosynthetic rationale is proposed, further extending the chemodiversity associated to Penicillium fungi. Preaustinoid C showed significant activity against LPS-induced NO production and selective effect on IL-2 and IFN-γ gene regulation in activated Jurkat cells.

Address: Department of Pharmacognosy, College of Pharmacy, King Saud University, P. O. Box 22452, Riyadh 11495, Saudi Arabia.; Department of Chemistry, School of Computer, Mathematical and Natural Sciences, Morgan State University, Baltimore, MD 21251, USA.; Department of Pharmacy, School of Medicine and Surgery, University of Naples Federico II, Via Montesano 49, 80131 Naples, Italy.; Department of Pharmacy, School of Medicine and Surgery, University of Naples Federico II, Via Montesano 49, 80131 Naples, Italy. Electronic address: [email protected].

DOI: 10.1016/j.fitote.2022.105330

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MeSH Terms: Humans, Penicillium, Lactones, Hot Springs, Molecular Structure, Polyketides