Antibacterial Bicyclic Fatty Acids from a Korean Colonial Tunicate Didemnum sp

Hiyoung Kim; Tae Gu Lee; Inho Yang; Weihong Wang; Jungwook Chin; Jusung Lee; Boon Jo Rho; Hyukjae Choi; Sang-Jip Nam; Dongyup Hahn; Heonjoong Kang

doi:10.3390/md19090521

Antibacterial Bicyclic Fatty Acids from a Korean Colonial Tunicate Didemnum sp

Mar Drugs. 2021 Sep 16;19(9):521. doi: 10.3390/md19090521.

Authors

Hiyoung Kim^{1

2}, Tae Gu Lee³, Inho Yang⁴, Weihong Wang^{1

5}, Jungwook Chin⁶, Jusung Lee¹, Boon Jo Rho⁷, Hyukjae Choi⁸, Sang-Jip Nam⁹, Dongyup Hahn¹⁰, Heonjoong Kang^{1

5

11}

Affiliations

¹ Laboratory of Marine Drugs, School of Earth and Environmental Sciences, Seoul National University, NS-80, Seoul 08826, Korea.
² Department of Biomedical Science and Engineering, Konkuk University, Seoul 05029, Korea.
³ Safety Research Team, Crop Protection Research Institute, FarmHannong Co., Ltd., Nonsan 33010, Korea.
⁴ Department of Convergence Study on the Ocean Science and Technology, Korea Maritime and Ocean University, Busan 49112, Korea.
⁵ Research Institute of Oceanography, Seoul National University, Seoul 08826, Korea.
⁶ New Drug Development Center, Daegu-Gyeongbuk Medical Innovation Foundation, Daegu 41061, Korea.
⁷ Natural History Museum, Ewha Womans University, Seoul 03760, Korea.
⁸ College of Pharmacy, Yeungnam University, Gyeongsan 38541, Korea.
⁹ Department of Chemistry and Nano Science, Ewha Womans University, Seoul 03760, Korea.
¹⁰ School of Food Science and Biotechnology & Department of Integrative Biology, Kyungpook National University, Daegu 41566, Korea.
¹¹ Interdisciplinary Graduate Program in Genetic Engineering, Seoul National University, NS-80, Seoul 08826, Korea.

Abstract

Five new bicyclic carboxylic acids were obtained by antibacterial activity-guided isolation from a Korean colonial tunicate Didemnum sp. Their structures were elucidated by the interpretation of NMR, MS and CD spectroscopic data. They all belong to the class of aplidic acids. Three of them were amide derivatives (1-3), and the other two were dicarboxylic derivatives (4 and 5). The absolute configurations were determined by a bisignate pattern of CD spectroscopy, which revealed that the absolute configurations of amides were opposite to those of dicarboxylates at every stereogenic centers. Compound 2 exhibited the most potent antibacterial activity (MIC, 2 μg/mL).

Keywords: Didemnum; antibacterial; bicyclic fatty acids; colonial tunicate.

MeSH terms

Animals
Anti-Bacterial Agents / chemistry*
Anti-Bacterial Agents / pharmacology*
Fatty Acids / chemistry*
Fatty Acids / pharmacology*
Molecular Structure
Staphylococcus aureus / drug effects
Urochordata / chemistry*

Substances

Anti-Bacterial Agents
Fatty Acids

Abstract

MeSH terms

Substances

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