Natural Product Sciences

The Korean Society of Pharmacognosy (한국생약학회)
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A Novel Bromoindole Alkaloid from a Korean Colonial Tunicate Didemnum sp.

  • Hahn, Dongyup (School of Earth and Environmental Sciences, Seoul National University) ;
  • Kim, Geum Jin (College of Pharmacy, Yeungnam University) ;
  • Choi, Hyukjae (College of Pharmacy, Yeungnam University) ;
  • Kang, Heonjoong (School of Earth and Environmental Sciences, Seoul National University)
  • Received : 2015.07.31
  • Accepted : 2015.08.18
  • Published : 2015.12.31
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Abstract

Chemical investigation on a colonial marine tunicate, Didemnum sp. led to the isolation of a series of indole alkaloids including a new (1) and two known metabolites (2-3). Based on the spectroscopic analysis including 1D and 2D NMR along with MS spectra, the structure of 1 (16-epi-18-acetyl herdmanine D) was elucidated as a new amino acid derivative. The absolute configuration of 1 was determined by comparison of specific rotation with the known compound. The structures of compounds 2 and 3 were also identified as bromoindole containing compounds N-(6-bromo-1H-indole-3-carbonyl)-L-arginine and (6-bromo-^1H-indol-3-yl) oxoacetamide, respectively, based on $^1H$ and $^{13}C$ NMR data, MS data and specific rotation value. Their pharmacological potentials as antibacterial agents and FXR antagonists were investigated, but no significant activity was found. However, the structural similarity of compound 1 to compound 4 suggested the anti-inflammatory potential of compound 1.

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Cited by

  1. Marine natural products vol.34, pp.3, 2015, https://doi.org/10.1039/c6np00124f
  2. Secondary Metabolites of the Genus Didemnum : A Comprehensive Review of Chemical Diversity and Pharmacological Properties vol.18, pp.6, 2020, https://doi.org/10.3390/md18060307
  3. Marine Indole Alkaloids-Isolation, Structure and Bioactivities vol.19, pp.12, 2021, https://doi.org/10.3390/md19120658