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Journal article

Cyclopiamines C and D: Epoxide Spiroindolinone Alkaloids from Penicillium sp. CML 3020

From

Department of Biotechnology and Biomedicine, Technical University of Denmark1

Natural Product Discovery, Section for Microbial and Chemical Ecology, Department of Biotechnology and Biomedicine, Technical University of Denmark2

Universidade Federal de São Paulo3

German Cancer Research Center4

Department of Chemistry, Technical University of Denmark5

Organic Chemistry, Department of Chemistry, Technical University of Denmark6

Fungal Chemodiversity, Section for Microbial and Chemical Ecology, Department of Biotechnology and Biomedicine, Technical University of Denmark7

Universidade Federal de Viçosa8

Cyclopiamines C (1) and D (2) were isolated from the extract of Penicillium sp. CML 3020, a fungus sourced from an Atlantic Forest soil sample. Their structures and relative configuration were determined by 1D and 2D NMR, HRMS, and UV/vis data analysis. Cyclopiamines C and D belong to a small subset of rare spiroindolinone compounds containing an alkyl nitro group and a 4,5-dihydro-1H-pyrrolo[3,2,1-ij]quinoline-2,6-dione ring system.

NMR and MS/HRMS data confirmed the presence of an epoxide unit (C-17-O-C-18) and a hydroxy group at C-5, not observed for their known congeners. Cytotoxic and antimicrobial activities were evaluated.

Language: English
Publisher: American Chemical Society and American Society of Pharmacognosy
Year: 2018
Pages: 785-790
ISSN: 15206025 and 01633864
Types: Journal article
DOI: 10.1021/acs.jnatprod.7b00825
ORCIDs: Kildgaard, Sara , Larsen, Thomas O. , Gotfredsen, Charlotte H. , Frisvad, Jens Christian and Nielsen, Kristian Fog

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