Osmanicin, a Polyketide Alkaloid Isolated from Streptomyces osmaniensis CA-244599 Inhibits Elastase in Human Fibroblasts
by
Mamdouh N. Samy 1
, Géraldine Le Goff 1, Philippe Lopes 1, Katerina Georgousaki 2, Sentiljana Gumeni 3, Celso Almeida 4, Ignacio González 4, Olga Genilloud 4, Ioannis Trougakos 3, Nikolas Fokialakis 2 and Jamal Ouazzani 1,*
Mamdouh N. Samy 1, Géraldine Le Goff 1, Philippe Lopes 1, Katerina Georgousaki 2, Sentiljana Gumeni 3, Celso Almeida 4, Ignacio González 4, Olga Genilloud 4, Ioannis Trougakos 3, Nikolas Fokialakis 2 and Jamal Ouazzani 1,*
1
Institut de Chimie des Substances Naturelles ICSN, Centre National de la Recherche Scientifique, Avenue de la Terrasse, 91198 Gif-sur-Yvette, France
2
Department of Pharmacognosy & Natural Products Chemistry, Faculty of Pharmacy, National and Kapodistrian University of Athens, 15771 Athens, Greece
3
Department of Cell Biology and Biophysics, Faculty of Biology, National and Kapodistrian University of Athens, 15784 Athens, Greece
4
Fundación MEDINA, Parque Tecnológico de Ciencias de la Salud, 18016 Granada, Spain
*
Author to whom correspondence should be addressed.
Molecules 2019, 24(12), 2239; https://doi.org/10.3390/molecules24122239
Received: 24 May 2019 / Revised: 11 June 2019 / Accepted: 12 June 2019 / Published: 15 June 2019
The strain Streptomyces osmaniensis CA-244599 isolated from the Comoros islands was submitted to liquid-state fermentation coupled to in situ solid-phase extraction with amberlite XAD-16 resin. Elution of the trapped compounds on the resin beads by ethyl acetate afforded seven metabolites, osmanicin (1), streptazolin (2), streptazone C (3), streptazone B1 (4), streptenol C (5), nocardamine (6) and desmethylenylnocardamine (7). Osmanicin (1) is a newly reported unusual scaffold combining streptazolin (2) and streptazone C (3) through a Diels-Alder type reaction. Experimental evidence excluded the spontaneous formation of 1 from 2 and 3. The isolated compounds were evaluated for their ability to inhibit elastase using normal human diploid fibroblasts. Compound 1 exhibited the most potent activity with an IC50 of 3.7 μM.
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Keywords:
Streptomyces osmaniensis; in situ solid-phase extraction; osmanicin; alkaloids; elastase inhibition
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MDPI and ACS Style
Samy, M.N.; Le Goff, G.; Lopes, P.; Georgousaki, K.; Gumeni, S.; Almeida, C.; González, I.; Genilloud, O.; Trougakos, I.; Fokialakis, N.; Ouazzani, J. Osmanicin, a Polyketide Alkaloid Isolated from Streptomyces osmaniensis CA-244599 Inhibits Elastase in Human Fibroblasts. Molecules 2019, 24, 2239.
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