Marilines A–C: Novel Phthalimidines from the Sponge‐Derived Fungus Stachylidium sp. |
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| Authors: | Dr Celso Almeida Yasmin Hemberger Sven Marcel Schmitt Sarah Bouhired Lavanya Natesan Dr Stefan Kehraus Dr Konstantinos Dimas Prof?Dr Michael Gütschow Prof?Dr Gerhard Bringmann Prof?Dr Gabriele M König |
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| Institution: | 1. Institute for Pharmaceutical Biology, University of Bonn, Nussallee 6, 53115 Bonn (Germany), Fax: (+49)?228‐733250;2. Current address: Laboratory of Tropical Bioorganic Chemistry, Faculty of Natural Exact Sciences and Technology, University of Panama (Panama);3. Institute of Organic Chemistry, University of Würzburg, Am Hubland, 97074 Würzburg (Germany), Fax: (+49)?931‐3184755;4. Laboratory of Pharmacology, Faculty of Medicine, University of Thessaly, Biopolis, 41110 Larissa (Greece);5. Pharmaceutical Institute, Pharmaceutical Chemistry I, University of Bonn, An der Immenburg 4, 53121 Bonn (Germany) |
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| Abstract: | A marine‐derived fungus of the genus Stachylidium was isolated from the sponge Callyspongia cf. C. flammea. Chemical investigation of the bioactive fungal extract led to the isolation of the novel phthalimidine derivatives marilines A1 ( 1 a ), A2 ( 1 b ), B ( 2 ), and C ( 3 ). The absolute configurations of the enantiomeric compounds 1 a and 1 b were assigned by a combination of experimental circular dichroism (CD) investigations and quantum chemical CD calculations. The skeleton of marilines is most unusual, and its biosynthesis is suggested to require uncommon biochemical reactions in fungal secondary metabolism. Both enantiomers, marilines A1 ( 1 a ) and A2 ( 1 b ), inhibited human leukocyte elastase (HLE) with an IC50 value of 0.86 μM . |
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| Keywords: | CD spectroscopy human leukocyte elastase marine fungus phthalimidine Stachylidium |
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