Journal
BIOORGANIC CHEMISTRY
Volume 110, Issue -, Pages -Publisher
ACADEMIC PRESS INC ELSEVIER SCIENCE
DOI: 10.1016/j.bioorg.2021.104822
Keywords
Diketopiperazine; Aspergillus creber; Rhodomela confervoides; Endophytic fungus; ACE inhibitory activity
Funding
- National Natural Science Foundation of China (NSFC) [42006079, 41706182]
- Qingdao National Laboratory for Marine Science and Technology [OF2019NO03]
- Taishan Scholar Project from Shandong Province of China [ts201511060]
Ask authors/readers for more resources
Thirteen alkaloids, including three new diketopiperazines and ten known derivatives, were isolated from the marine red algal-derived fungus Aspergillus creber EN-602. Some of these compounds showed inhibitory activity against ACE and aquatic bacteria, with further investigation on their interactions through molecular docking simulations with ACE.
Thirteen alkaloids, which include three new diketopiperazines, namely, 3-hydroxyprotuboxepin K (4), 3,15dehydroprotuboxepin K (5), and versiamide A (6), together with ten known alkaloid derivatives (1-3 and 7-13), were isolated from the marine red algal-derived fungus Aspergillus creber EN-602. Versiamide A (6) represents the first example of a naturally occurring quinazolinone alkaloid with a diketopiperazine ring that is derived from phenylalanine (Phe) and leucine (Leu). The structures of these compounds were elucidated by detailed interpretation of their 1D/2D NMR spectroscopic and mass spectrometric data, while the absolute configurations of compounds 1-6 were established on the basis of X-ray crystallographic analysis and time-dependent density functional (TDDFT) calculations of the ECD spectra. Compounds 1, 2, and 4 exhibited inhibitory activity against the angiotensin converting enzyme (ACE) with IC50 values of 11.2, 16.0, and 22.4 mu M, respectively, and compounds 5 and 6 inhibited various aquatic bacteria with MIC values that ranged from 8 to 64 mu g/mL. The intermolecular interactions and potential binding sites between compounds 1-6 and ACE were investigated via molecular docking simulations.
Authors
I am an author on this paper
Click your name to claim this paper and add it to your profile.
Reviews
Recommended
No Data Available