Analysis on the Structure of Phlorethols Isolated From the Warm-Temperate Brown Seaweed Sargassum carpophyllum and Their Antioxidant Properties

Abstract

The brown seaweed Sargassum carpophyllum J. Agardh is an unused warm-temperate species in the family Sargassaceae that has been expanding its distribution along the coastal areas of Japan in recent years. In this study, 3 types of phlorotannins were identified from the EtOAc fraction of the 80% MeOH extract of S. carpophyllum. From the spectroscopic (1H NMR, 13C NMR, and HMBC) and ESI/MS data and comparison with those of prior literature, it was demonstrated that the compounds are oligomers of phlorethol, which is one of the subclasses of phlorotannins, that is triphlorethol B (phloroglucinol trimer), tetraphlorethol C (phloroglucinol tetramer), and pentaphlorethol A (phloroglucinol pentamer). Among the phlorethols, tetraphlorethol C and pentaphlorethol A were isolated and identified for the first time from a brown seaweed collected from the East China Sea, including the coastal areas of Japan. The identified phlorethols were tested for their antioxidant properties. In the antioxidant assay using liposomes, the phlorethols showed comparable inhibitory effects to epigallocatechin gallate (tea polyphenol) and α-tocopherol (liposoluble vitamin) on lipid peroxidation by 4 mM 2,2′-azobis(2-methylpropionamidine) dihydrochloride. In addition, it was revealed that pentaphlorethol A has a superoxide anion scavenging activity (50% effective concentration: 21 μM) higher than that (50% effective concentration: 46 μM) of ascorbic acid (hydrosoluble vitamin).