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

ABSTRACT: 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 ?M.

SUBMITTER: Samy MN 

PROVIDER: S-EPMC6630352 | biostudies-literature | 2019 Jun

REPOSITORIES: biostudies-literature

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Osmanicin, a Polyketide Alkaloid Isolated from <i>Streptomyces osmaniensis</i> CA-244599 Inhibits Elastase in Human Fibroblasts.

Samy Mamdouh N MN   Le Goff Géraldine G   Lopes Philippe P   Georgousaki Katerina K   Gumeni Sentiljana S   Almeida Celso C   González Ignacio I   Genilloud Olga O   Trougakos Ioannis I   Fokialakis Nikolas N   Ouazzani Jamal J  

Molecules (Basel, Switzerland) 20190615 12

The strain <i>Streptomyces osmaniensis</i> 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 (<b>1</b>), streptazolin (<b>2</b>), streptazone C (<b>3</b>), streptazone B<sub>1</sub> (<b>4</b>), streptenol C (<b>5</b>), nocardamine (<b>6</b>) and desmethylenylnocardamine (<b>7</b>). Os  ...[more]

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