During investigation of the secondary metabolism of four strains of Penicillium arenicola, two new depsides, arenicolins A (1) and B (2), were isolated and characterized. Their structures were established mainly by analysis of NMR and HRMS data and by comparison with known compounds. These depsides incorporate intriguing structural features, including dual alkyl side chains and a C-glycosyl unit, with 1 also containing an acylated 2-hydroxymethyl-4,5,6-trihydroxycyclohexenone moiety. Although the arenicolins were produced by all strains tested, arenicolin A (1) was obtained using only one of five medium compositions employed, while arenicolin B (2) was produced in all media tested. Neither compound showed antibacterial or antifungal activity, but 1 exhibited cytotoxicity toward mammalian cell lines, including colorectal carcinoma (HCT-116), neuroblastoma (IMR-32), and ductal carcinoma (BT-474), with IC50 values of 7.3, 6.0, and 9.7 μM, respectively.
cytotoxicity, anticancer activity, Penicillium arenicola, arenicolins
NCBI PubMed ID: 31999116Publication DOI: 10.1021/acs.jnatprod.9b01099Journal NLM ID: 7906882Publisher: American Society of Pharmacognosy
Correspondence: James Gloer
Institutions: Department of Chemistry, UniVersity of Iowa, Iowa City, USA, Texas Therapeutic Institute, The Brown Foundation Institute of Molecular Medicine, University of Texas Health Science Center at Houston, Houston, USA, The Brown Foundation Institute of Molecular Medicine, McGovern Medical School, University of Texas Health Science Center at Houston, Houston, USA
Methods: 13C NMR, 1H NMR, NMR-2D, HPLC, UV, extraction, optical rotation measurement, cell growth, HPLC-MS, HR-ESI-MS, cytotoxicity assay, evaporation, antimicrobial assay, flash chromatography, HPLC-DAD, HPLC-ELSD, ECD
Found