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Antibacterial Isoquinoline Alkaloids from the Fungus Penicillium Spathulatum Em19

Nord, Christina and Levenfors, Jolanta and Bjerketorp, Joakim and Sahlberg, Christer and Guss, Bengt and Öberg, Bo and Broberg, Anders (2019). Antibacterial Isoquinoline Alkaloids from the Fungus Penicillium Spathulatum Em19. Molecules. 24 , 1-11
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Abstract

In the search for new microbial antibacterial secondary metabolites, two new compounds (1 and 2) were isolated from culture broths of Penicillium spathulatum Em19. Structure determination by nuclear magnetic resonance and mass spectrometry identified the compounds as 6,7-dihydroxy-5,10-dihydropyrrolo[1,2-b]isoquinoline-3-carboxylic acid (1, spathullin A) and 5,10-dihydropyrrolo[1,2-b]isoquinoline-6,7-diol (2, spathullin B). The two compounds displayed activity against both Gram-negative and -positive bacteria, including Escherichia coli, Acinetobacter baumannii, Enterobacter cloacae, Klebsiella pneumonia, Pseudomonas aeruginosa, and Staphylococcus aureus. Compound 2 was more potent than 1 against all tested pathogens, with minimal inhibitory concentrations down to 1 µg/mL (5 µM) against S. aureus, but 2 was also more cytotoxic than 1 (50% inhibitory concentrations 112 and 11 µM for compounds 1 and 2, respectively, towards Huh7 cells). Based on stable isotope labelling experiments and a literature comparison, the biosynthesis of 1 was suggested to proceed from cysteine, tyrosine and methionine via a non-ribosomal peptides synthase like enzyme complex, whereas compound 2 was formed spontaneously from 1 by decarboxylation. Compound 1 was also easily oxidized to the 1,2-benzoquinone 3. Due to the instability of compound 1 and the toxicity of 2, the compounds are of low interest as possible future antibacterial drugs.

Authors/Creators:Nord, Christina and Levenfors, Jolanta and Bjerketorp, Joakim and Sahlberg, Christer and Guss, Bengt and Öberg, Bo and Broberg, Anders
Title:Antibacterial Isoquinoline Alkaloids from the Fungus Penicillium Spathulatum Em19
Year of publishing :2019
Volume:24
Page range:1-11
Number of Pages:11
Publisher:MDPI
ISSN:1420-3049
Language:English
Publication Type:Journal article
Refereed:Yes
Article category:Scientific peer reviewed
Version:Published version
Copyright:Creative Commons: Attribution 4.0
Full Text Status:Public
Subjects:(A) Swedish standard research categories 2011 > 1 Natural sciences > 106 Biological Sciences (Medical to be 3 and Agricultural to be 4) > Microbiology (Microbiology in the medical area to be 30109)
Keywords:antibiotic resistance, antibacterial secondary metabolites, secondary metabolism, Penicillium, isoquinoline alkaloids, dehydroalanine
URN:NBN:urn:nbn:se:slu:epsilon-p-103675
Permanent URL:
http://urn.kb.se/resolve?urn=urn:nbn:se:slu:epsilon-p-103675
Additional ID:
Type of IDID
DOI10.3390/molecules24244616
ID Code:16595
Faculty:NJ - Fakulteten för naturresurser och jordbruksvetenskap
VH - Faculty of Veterinary Medicine and Animal Science
Department:(NL, NJ) > Department of Molecular Sciences
(VH) > Dept. of Biomedical Sciences and Veterinary Public Health
Deposited By: SLUpub Connector
Deposited On:05 Mar 2020 07:51
Metadata Last Modified:20 Mar 2020 08:17

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