Abstract
In this study, 5 sterols were isolated and purified from Laminaria japonica, commonly known as edible brown seaweed, and their structures were identified based on detailed chemical methods and spectroscopic analyses. Spectroscopic analyses characterized 5 sterols as 29-Hydroperoxy-stigmasta-5,24(28)-dien-3β-ol, saringosterol (24-vinyl-cholest-5-ene-3β,24-diol), 24-methylenecholesterol, fucosterol (stigmasta-5,24-diene-3β-ol), and 24-Hydroperoxy-24-vinyl-cholesterol. The bioactivities of these sterols were tested using lipid peroxidation (LPO) and cyclooxygenase (COX-1 and -2) enzyme inhibitory assays. Fucosterol exhibited the highest COX-1 and -2 enzyme inhibitory activities at 59 and 47%, respectively. Saringosterol, 24-methylenecholesterol and fucosterol showed higher LPO inhibitory activity at >50% than the other compounds. In addition, the results of molecular docking revealed that the 5 sterols were located in different pocket of COX-1 and -2 and fucosterol with tetracyclic skeletons and olefin methine achieved the highest binding energy (-7.85 and -9.02 kcal/mol) through hydrophobic interactions and hydrogen bond. Our results confirm the presence of 5 sterols in L. japonica and its significant anti-inflammatory and antioxidant activity.
Highlights
Laminaria japonica, a commercial edible brown seaweed, is widely cultivated and consumed as a health food resource in China, Japan, and Korea
Positive controls for the COX and lipid peroxidation (LPO) assays aspirin, naproxen, Celebrex1, ibuprofen, TBHQ (t-butylhydroquinone), butylated hydroxyanisole (BHA), butylated hydroxytoluene (BHT) and cholesterol were purchased from Sigma-Aldrich Chemical Company
The results of molecular docking predicted that 5 sterols were located in different pocket of COX-1 and -2 and confirmed that fucosterol with tetracyclic skeletons and olefin methine achieved the best COX-1 and -2 enzyme inhibitory activities through hydrophobic interactions and hydrogen bond
Summary
A commercial edible brown seaweed, is widely cultivated and consumed as a health food resource in China, Japan, and Korea. L. japonica is one of the most important marine medicinal foodstuffs and a rich source of various functional compounds, which have been widely investigated by both in vitro and in vivo experiments [1,2,3,4]. HRMS data were obtained at the Michigan State University Mass Spectrometry Facility, which is supported, in part, by a grant (DRR-00480) from the Biotechnology Research Technology Program, National Centre for Research Resources, National Institutes of Health
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