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Molecules 2018, 23(12), 3187; https://doi.org/10.3390/molecules23123187

Scalalactams A–D, Scalarane Sesterterpenes with a γ-Lactam Moiety from a Korean Spongia Sp. Marine Sponge

1
Department of Convergence Study on the Ocean Science and Technology, Korea Maritime and Ocean University, Busan 49112, Korea
2
The Center for Marine Natural Products and Drug Discovery, School of Earth and Environmental Science, Seoul National University, NS-80, Seoul 08826, Korea
3
School of Food Science and Biotechnology, Kyungpook National University, Daegu 41566, Korea
4
Institute of Agricultural Science & Technology, Kyungpook National University, Daegu 41566, Korea
5
New Drug Development Center, Daegu-Gyeongbuk Medicinal Innovation Foundation, Daegu 41061, Korea
6
Basic Research & Innovation Division, Amorepacific R&D Unit, Yongin 17074, Korea
7
College of Pharmacy, Yeungnam University, Gyeongsan 38541, Korea
8
Graduate School of Industrial Pharmaceutical Sciences, Ewha Womans University, Seoul 03760, Korea
9
Department of Chemistry and Nanoscience, Ewha Womans University, Seoul 03760, Korea
10
Research Institute of Oceanography, Seoul National University, NS-80, Seoul 08826, Korea
These authors contributed equally to this work.
*
Authors to whom correspondence should be addressed.
Received: 16 October 2018 / Revised: 30 November 2018 / Accepted: 30 November 2018 / Published: 3 December 2018
(This article belongs to the Section Natural Products Chemistry)
PDF [306 KB, uploaded 3 December 2018]   |  

Abstract

Intensive study on the chemical components of a Korean marine sponge, Spongia sp., has led to the isolation of four new scalarane sesterterpenes, scalalactams A–D (14). Their chemical structures were elucidated from the analysis of spectroscopic data including 1D-and 2D-NMR as well as MS data. Scalalactams A–D (14) possess a scalarane carbon skeleton with a rare structural feature of a γ-lactam moiety within the molecules. Scalalactams A and B (1 and 2) have an extended isopropanyl chain at the lactam ring, and scalalactams C and D (3 and 4) possess a phenethyl group at the lactam ring moiety. Scalalactams A–D (14) did not show FXR antagonistic activity nor cytotoxicity up to 100 μM.
Keywords: scalarane sesterterpenes; scalalactams; marine natural products; marine sponge; Spongia sp scalarane sesterterpenes; scalalactams; marine natural products; marine sponge; Spongia sp
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This is an open access article distributed under the Creative Commons Attribution License which permits unrestricted use, distribution, and reproduction in any medium, provided the original work is properly cited (CC BY 4.0).

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Yang, I.; Lee, J.; Lee, J.; Hahn, D.; Chin, J.; Won, D.H.; Ko, J.; Choi, H.; Hong, A.; Nam, S.-J.; Kang, H. Scalalactams A–D, Scalarane Sesterterpenes with a γ-Lactam Moiety from a Korean Spongia Sp. Marine Sponge. Molecules 2018, 23, 3187.

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