Journal article
Arenicolins: C‑Glycosylated Depsides from Penicillium arenicola
Journal of natural products (Washington, D.C.), Vol.83(3), pp.668-674
03/27/2020
DOI: 10.1021/acs.jnatprod.9b01099
PMCID: PMC7495882
PMID: 31999116
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.
Details
- Title: Subtitle
- Arenicolins: C‑Glycosylated Depsides from Penicillium arenicola
- Creators
- Bruno Perlatti - Texas Therapeutic Institute, The Brown Foundation Institute of Molecular MedicineNan Lan - Texas Therapeutic Institute, The Brown Foundation Institute of Molecular MedicineCody E Earp - Department of ChemistrySolmaz AghaAmiri - The Brown Foundation Institute of Molecular Medicine, McGovern Medical SchoolServando Hernandez Vargas - The Brown Foundation Institute of Molecular Medicine, McGovern Medical SchoolAli Azhdarinia - The Brown Foundation Institute of Molecular Medicine, McGovern Medical SchoolGerald F Bills - Texas Therapeutic Institute, The Brown Foundation Institute of Molecular MedicineJames B Gloer - Department of Chemistry
- Resource Type
- Journal article
- Publication Details
- Journal of natural products (Washington, D.C.), Vol.83(3), pp.668-674
- DOI
- 10.1021/acs.jnatprod.9b01099
- PMID
- 31999116
- PMCID
- PMC7495882
- NLM abbreviation
- J Nat Prod
- ISSN
- 0163-3864
- eISSN
- 1520-6025
- Publisher
- American Chemical Society and American Society of Pharmacognosy
- Grant note
- DOI: 10.13039/100012615, name: University of Texas Health Science Center at Houston; DOI: 10.13039/100000057, name: National Institute of General Medical Sciences, award: R01 GM121458
- Language
- English
- Date published
- 03/27/2020
- Academic Unit
- Chemistry
- Record Identifier
- 9984216578402771
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