Polychlorinated cyclopentenes from a marine derived Periconia sp. (strain G1144). (July 2022)

• Record Type: Journal Article
• Authors: Cank, Kristóf B.; Shepherd, Robert A.; Knowles, Sonja L.; Rangel-Grimaldo, Manuel; Raja, Huzefa A.; Bunch, Zoie L.; Cech, Nadja B.; Rice, Christopher A.; Kyle, Dennis E.; Falkinham, Joseph O.; Burdette, Joanna E.; Oberlies, Nicholas H.
• Is Part Of: Phytochemistry. Volume 199(2022)
• Publication Date: 2022-07
• Subjects: Periconia sp. -- Marine fungi -- GIAO NMR calculations -- Halogenated cyclopentenes; Botanical chemistry -- Periodicals; Biochemistry -- Periodicals; Botany -- Periodicals; Chimie végétale -- Périodiques; 572.2
• DOI: 10.1016/j.phytochem.2022.113200
• Languages: English
• ISSNs: 0031-9422

Abstract

Abstract: Studies on an organic extract of a marine fungus, Periconia sp. (strain G1144), led to the isolation of three halogenated cyclopentenes along with the known and recently reported rhytidhyester D; a series of spectrometric and spectroscopic techniques were used to elucidate these structures. Interestingly, two of these compounds represent tri-halogenated cyclopentene derivatives, which have been observed only rarely from Nature. The relative and absolute configurations of the compounds were established via mass spectrometry (MS), nuclear magnetic resonance (NMR) spectroscopy, Mosher's esters method, optical rotation and GIAO NMR calculations, including correlation coefficient calculations and the use of both DP4+ and dJ DP4 analyses. Several of the isolated compounds were tested for activity in anti-parasitic, antimicrobial, quorum sensing inhibition, and cytotoxicity assays and were shown to be inactive. Graphical abstract: Image 1 Highlights: Periconia spp. are capable of biosynthesizing halogenated polyketide derivatives. Cryptosporiopsinol B, C, D and rhytidhyester D were isolated from a marine derived Periconia sp. Relative configurations were established via MS and NMR techniques. Absolute configurations were solved via Mosher's esters method and NMR calculations.