Journal article
Anti-Cryptococcus Phenalenones and Cyclic Tetrapeptides from Auxarthron pseudauxarthron
Journal of natural products (Washington, D.C.), Vol.80(7), pp.2101-2109
07/28/2017
DOI: 10.1021/acs.jnatprod.7b00341
PMCID: PMC5629637
PMID: 28657331
Abstract
Auxarthrones A-E (1-5), five new phenalenones, and two new naturally occurring cyclic tetrapeptides, auxarthrides A (7) and B (8), were obtained from three different solvent extracts of cultures of the coprophilous fungus Auxarthron pseudauxarthron. Auxarthrones C (3) and E (5) possess an unusual 7a,8-dihydrocyclopenta[a]phenalene-7,9-dione ring system that has not been previously observed in natural products. Formation of 1-5 was found to be dependent on the solvent used for culture extraction. The structures of these new compounds were elucidated primarily by analysis of NMR and MS data. Auxarthrone A (1) was obtained as a mixture of chromatographically inseparable racemic diastereomers (1a and 1b) that cocrystallized, enabling confirmation of their structures by X-ray crystallography. The absolute configurations of 7 and 8 were assigned by analysis of their acid hydrolysates using Marfey's method. Compound 1 displayed moderate antifungal activity against Cryptococcus neoformans and Candida albicans, but did not affect human cancer cell lines.
Details
- Title: Subtitle
- Anti-Cryptococcus Phenalenones and Cyclic Tetrapeptides from Auxarthron pseudauxarthron
- Creators
- Yan Li - Texas Therapeutic Institute, The Brown Foundation Institute of Molecular Medicine, University of Texas Health Science Center at Houston , Houston, Texas 77054, United StatesQun Yue - Texas Therapeutic Institute, The Brown Foundation Institute of Molecular Medicine, University of Texas Health Science Center at Houston , Houston, Texas 77054, United StatesDinith R Jayanetti - Department of Chemistry, University of Iowa , Iowa City, Iowa 52242, United StatesDale C Swenson - Department of Chemistry, University of Iowa , Iowa City, Iowa 52242, United StatesGeoffrey A Bartholomeusz - Department of Experimental Therapeutics, Division of Cancer Medicine, The University of Texas MD Anderson Cancer Center , Houston, Texas 77054, United StatesZhiqiang An - Texas Therapeutic Institute, The Brown Foundation Institute of Molecular Medicine, University of Texas Health Science Center at Houston , Houston, Texas 77054, United StatesJames B Gloer - Department of Chemistry, University of Iowa , Iowa City, Iowa 52242, United StatesGerald F Bills - Texas Therapeutic Institute, The Brown Foundation Institute of Molecular Medicine, University of Texas Health Science Center at Houston , Houston, Texas 77054, United States
- Resource Type
- Journal article
- Publication Details
- Journal of natural products (Washington, D.C.), Vol.80(7), pp.2101-2109
- DOI
- 10.1021/acs.jnatprod.7b00341
- PMID
- 28657331
- PMCID
- PMC5629637
- NLM abbreviation
- J Nat Prod
- ISSN
- 0163-3864
- eISSN
- 1520-6025
- Publisher
- United States
- Grant note
- R01 GM121458 / NIGMS NIH HHS
- Language
- English
- Date published
- 07/28/2017
- Academic Unit
- Chemistry
- Record Identifier
- 9983985958102771
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