Aaptocarbamates A-G, chlorinated terpene carbamates with antiosteoclastogenic activities from the marine sponge Aaptos sp.

Six undescribed chlorinated sesquiterpene carbamates, aaptocarbamates A-F, and a chlorinated tris-norsesquiterpene carbamate, aaptocarbamate G, were isolated from the marine sponge Aaptos sp. collected in Indonesia. Aaptocarbamates D-F and G possess tetrahydrofurans and a tetrahydrofuranone, respectively. The relative configurations of the tetrahydrofuran units were determined by the NOE correlations and DFT-based calculation of the 13C chemical shifts. This is the first time that chlorinated terpene carbamates have been reported from natural sources. Various aaptamine derivatives have been reported from the Aaptos sponges so far, the isolation of chlorinated terpene carbamates is very rare. Aaptocarbamates A, B, and D showed 60% inhibition of the RANKL-induced formation of multinucleated osteoclasts in RAW264 macrophages at 20 μM. Copyright © 2023 Elsevier Ltd. All rights reserved.

Citation

Ahmed H El-Desoky, Keisuke Eguchi, Ippei Kagiyama, Yuki Hitora, Hikaru Kato, Yuji Ise, Fitje Losung, Remy E P Mangindaan, Sachiko Tsukamoto. Aaptocarbamates A-G, chlorinated terpene carbamates with antiosteoclastogenic activities from the marine sponge Aaptos sp. Phytochemistry. 2023 Dec;216:113872

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PMID: 37769957

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