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Donghaecyclinones A–C: New Cytotoxic Rearranged Angucyclinones from a Volcanic Island-Derived Marine Streptomyces sp.

1
Natural Products Research Institute, College of Pharmacy, Seoul National University, Seoul 08826, Korea
2
Department of Agricultural Biotechnology, College of Agriculture & Life Sciences, Seoul National University, Seoul 08826, Korea
3
Research Institute of Pharmaceutical Sciences, College of Pharmacy, Seoul National University, Seoul 08826, Korea
*
Author to whom correspondence should be addressed.
Mar. Drugs 2020, 18(2), 121; https://doi.org/10.3390/md18020121
Received: 16 January 2020 / Revised: 8 February 2020 / Accepted: 10 February 2020 / Published: 18 February 2020
Chemical profiling of the Streptomyces sp. strain SUD119, which was isolated from a marine sediment sample collected from a volcanic island in Korea, led to the discovery of three new metabolites: donghaecyclinones A–C (13). The structures of 13 were found to be rearranged, multicyclic, angucyclinone-class compounds according to nuclear magnetic resonance (NMR) and mass spectrometry (MS) analyses. The configurations of their stereogenic centers were successfully assigned using a combination of quantum mechanics–based computational methods for calculating the NMR shielding tensor (DP4 and CP3) as well as electronic circular dichroism (ECD) along with a modified version of Mosher’s method. Donghaecyclinones A–C (13) displayed cytotoxicity against diverse human cancer cell lines (IC50: 6.7–9.6 μM for 3). View Full-Text
Keywords: molecular modeling; electronic circular dichroism; quantum mechanics-based computation; angucyclinone; Streptomyces; cytotoxicity molecular modeling; electronic circular dichroism; quantum mechanics-based computation; angucyclinone; Streptomyces; cytotoxicity
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Bae, M.; An, J.S.; Hong, S.-H.; Bae, E.S.; Chung, B.; Kwon, Y.; Hong, S.; Oh, K.-B.; Shin, J.; Lee, S.K.; Oh, D.-C. Donghaecyclinones A–C: New Cytotoxic Rearranged Angucyclinones from a Volcanic Island-Derived Marine Streptomyces sp.. Mar. Drugs 2020, 18, 121.

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