2. Academic Validation
  3. Arenicolins: C-Glycosylated Depsides from Penicillium arenicola

Arenicolins: C-Glycosylated Depsides from Penicillium arenicola

  • J Nat Prod. 2020 Mar 27;83(3):668-674. doi: 10.1021/acs.jnatprod.9b01099.
Bruno Perlatti 1,  Nan Lan 1,  Cody E Earp 2,  Solmaz AghaAmiri 3,  Servando Hernandez Vargas 3,  Ali Azhdarinia 3,  Gerald F Bills 1,  James B Gloer 2
Affiliations

Affiliations

  • 1 Texas Therapeutic Institute, The Brown Foundation Institute of Molecular Medicine, University of Texas Health Science Center at Houston, Houston, Texas 77054, United States.
  • 2 Department of Chemistry, University of Iowa, Iowa City, Iowa 52242, United States.
  • 3 The Brown Foundation Institute of Molecular Medicine, McGovern Medical School, University of Texas Health Science Center at Houston, Houston, Texas 77054, United States.
PMID: 31999116 DOI: 10.1021/acs.jnatprod.9b01099
Abstract

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.

Figures