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Osmanicin, a Polyketide Alkaloid Isolated from Streptomyces osmaniensis CA-244599 Inhibits Elastase in Human Fibroblasts

1
Institut de Chimie des Substances Naturelles ICSN, Centre National de la Recherche Scientifique, Avenue de la Terrasse, 91198 Gif-sur-Yvette, France
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Department of Pharmacognosy & Natural Products Chemistry, Faculty of Pharmacy, National and Kapodistrian University of Athens, 15771 Athens, Greece
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Department of Cell Biology and Biophysics, Faculty of Biology, National and Kapodistrian University of Athens, 15784 Athens, Greece
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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. View Full-Text
Keywords: Streptomyces osmaniensis; in situ solid-phase extraction; osmanicin; alkaloids; elastase inhibition Streptomyces osmaniensis; in situ solid-phase extraction; osmanicin; alkaloids; elastase inhibition
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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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