Open AccessArenicolins: C-Glycosylated Depsides from Penicillium arenicola
Author(s) -
Bruno Perlatti,
Nan Li,
Cody E. Earp,
Solmaz AghaAmiri,
Servando Hernandez Vargas,
Ali Azhdarinia,
Gerald F. Bills,
James B. Gloer
Publication year - 2020
Publication title -
journal of natural products
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.976
H-Index - 139
eISSN - 1520-6025
pISSN - 0163-3864
DOI - 10.1021/acs.jnatprod.9b01099
Subject(s) - stereochemistry , penicillium , moiety , cytotoxicity , chemistry , antibacterial activity , biology , biochemistry , in vitro , bacteria , food science , genetics
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 IC 50 values of 7.3, 6.0, and 9.7 μM, respectively.