Journal article
Broomeanamides: Cyclic Octapeptides from an Isolate of the Fungicolous Ascomycete Sphaerostilbella broomeana from India
Journal of natural products (Washington, D.C.), Vol.84(7), pp.2028-2034
07/23/2021
DOI: 10.1021/acs.jnatprod.1c00414
PMCID: PMC8314271
PMID: 34191504
Appears in UI Libraries Support Open Access
Abstract
The genus Sphaerostilbella comprises fungi that colonize basidiomata of wood-inhabiting fungi, including important forest pathogens. Studies of fermentation cultures of an isolate (TFC201724) collected on the foothills of Himalayas, and closely related to S. broomeana isolates from Europe, led to the identification of a new cyclic octapeptide along with two closely related analogues (1–3) and four dioxopiperazines (4–7). The structure of the lead compound, broomeanamide A (1), was assigned mainly by analysis of 2D NMR and HRESIMS data. The structure consisted of one unit each of N-MeVal, Ala, N-MePhe, Pro, Val, and Ile and two N-MeLeu units. The amino acid sequence was determined on the basis of 2D NMR and HRESIMSMS data. NMR and HRMS data revealed that the other two new peptides have the same amino acid composition except that the Ile unit was replaced with Val in one instance (2) and the N-MeVal unit was replaced with Val in the other (3). The absolute configuration of 1 was assigned by analysis of the acid hydrolysate by application of Marfey’s method using both C18 and C3 bonded-phase columns. Broomeanamide A (1) showed antifungal activity against Cryptococcus neoformans and Candida albicans, with MIC values of 8.0 and 64 μg/mL, respectively.
Details
- Title: Subtitle
- Broomeanamides: Cyclic Octapeptides from an Isolate of the Fungicolous Ascomycete Sphaerostilbella broomeana from India
- Creators
- Dulamini I Ekanayake - Department of ChemistryBruno Perlatti - Texas Therapeutic Institute, The Brown Foundation Institute of Molecular MedicineDale C Swenson - Department of ChemistryKadri Põldmaa - University of TartuGerald 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.84(7), pp.2028-2034
- DOI
- 10.1021/acs.jnatprod.1c00414
- PMID
- 34191504
- PMCID
- PMC8314271
- NLM abbreviation
- J Nat Prod
- ISSN
- 0163-3864
- eISSN
- 1520-6025
- Publisher
- American Chemical Society
- Grant note
- DOI: 10.13039/100000097, name: National Center for Research Resources, award: S10 RR023384, S10 RR025500; DOI: 10.13039/100000057, name: National Institute of General Medical Sciences, award: R01 GM121458; DOI: 10.13039/100000001, name: National Science Foundation, award: CHE-1828117; name: Estonian Science Agency, award: PRG1170; name: Kay and Ben Fortson Endowment, award: none; DOI: 10.13039/501100008530, name: European Regional Development Fund, award: none
- Language
- English
- Date published
- 07/23/2021
- Academic Unit
- Chemistry
- Record Identifier
- 9984216684102771
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