Search: WFRF:(Bjerketorp Joakim) >
Antibacterial Isoqu...
Antibacterial Isoquinoline Alkaloids from the Fungus Penicillium Spathulatum Em19
-
- Nord, Christina (author)
- Swedish Univ Agr Sci, Uppsala BioCtr, Dept Mol Sci, POB 7015, SE-75007 Uppsala, Sweden
-
- Levenfors, Jolanta J. (author)
- Swedish Univ Agr Sci, Uppsala BioCtr, Dept Mol Sci, POB 7015, SE-75007 Uppsala, Sweden;Ultupharma AB, Sodra Rudbecksgatan 13, SE-75236 Uppsala, Sweden
-
- Bjerketorp, Joakim (author)
- Swedish Univ Agr Sci, Uppsala BioCtr, Dept Mol Sci, POB 7015, SE-75007 Uppsala, Sweden;Ultupharma AB, Sodra Rudbecksgatan 13, SE-75236 Uppsala, Sweden
-
show more...
-
- Sahlberg, Christer (author)
- Medivir AB, POB 1086, SE-14122 Huddinge, Sweden
-
- Guss, Bengt (author)
- Swedish Univ Agr Sci, Dept Biomed Sci & Vet Publ Hlth, POB 7036, SE-75007 Uppsala, Sweden
-
- Öberg, Bo (author)
- Uppsala universitet,Preparativ läkemedelskemi,Ultupharma AB, Sodra Rudbecksgatan 13, SE-75236 Uppsala, Sweden
-
- Broberg, Anders (author)
- Swedish Univ Agr Sci, Uppsala BioCtr, Dept Mol Sci, POB 7015, SE-75007 Uppsala, Sweden
-
show less...
-
(creator_code:org_t)
- 2019-12-17
- 2019
- English.
-
In: Molecules. - : MDPI. - 1431-5157 .- 1420-3049. ; 24:24
- Related links:
-
https://doi.org/10.3...
-
show more...
-
https://uu.diva-port... (primary) (Raw object)
-
https://www.mdpi.com...
-
https://urn.kb.se/re...
-
https://doi.org/10.3...
-
show less...
Abstract
Subject headings
Close
- 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, Acinetobacterbaumannii, Enterobactercloacae, Klebsiellapneumonia, Pseudomonasaeruginosa, and Staphylococcusaureus. Compound 2 was more potent than 1 against all tested pathogens, with minimal inhibitory concentrations down to 1 mu g/mL (5 mu M) against S. aureus, but 2 was also more cytotoxic than 1 (50% inhibitory concentrations 112 and 11 mu M 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.
Subject headings
- NATURVETENSKAP -- Kemi -- Organisk kemi (hsv//swe)
- NATURAL SCIENCES -- Chemical Sciences -- Organic Chemistry (hsv//eng)
Keyword
- antibiotic resistance
- antibacterial secondary metabolites
- secondary metabolism
- Penicillium
- isoquinoline alkaloids
- dehydroalanine
Publication and Content Type
- ref (subject category)
- art (subject category)
Find in a library
-
Molecules
(Search for host publication in LIBRIS)
To the university's database