Abstract
In search for new deodorizing compounds, we were identified three phlorotannins; eckol (1), dioxinodehydroeckol (2) and dieckol (3) from edible brown seaweed Eisenia bicyclis and characterized by Fast-atom bombardment mass spectrometry (FAB-MS) and nuclear magnetic resonance (NMR). The deodorizing activity of those compounds was evaluated against methyl mercaptan, which is well known as a major causative material of halitosis and off-flavor. Among them, compound 3 exhibited the highest deodorizing activity against methyl mercaptan at the IC50 values of 26.71 ± 4.16 µg mL-1, followed by compound 2 (40.57 ± 0.63 µg mL-1) and compound 1 (43.62 ± 1.52 µg mL-1). Thus, these results suggest that the phlorotannins derived from E. bicyclis can be an effective deodorizing constituent in the food industry and pharmaceutical industries.
Highlights
Volatile sulfide compounds (VCSs) such as hydrogen sulfide, dimethyl sulfide, and methyl mercaptan have been known as major compounds causing off-flavor from foods and the industrial sites (Tanabe et al, 2012)
The IC50 values of the EtOAc, n-butanol and DCM -soluble extracts were estimated to possess about 2 times to 8 times more strong deodorizing activity than sodium copper chlorophyllin, which is most widely known as a deodorant for halitosis
Lee et al (1999) reported that deodorizing activity of benxethonium, sodium fluoride, and cetylpyridinium chloride, which are used as the inhibitors of halitosis and antibacterial ingredients for commercial mouthwashes, against methyl mercaptan was less than 50% at concentration of 5 mg mL-1
Summary
Volatile sulfide compounds (VCSs) such as hydrogen sulfide, dimethyl sulfide, and methyl mercaptan have been known as major compounds causing off-flavor from foods and the industrial sites (Tanabe et al, 2012). It is generated through an enzymatic modification of sulfur containing amino acids (cysteine and methionine), which are made available following proteolytic degradation of proteins (Hughes & McNab, 2008; Ali & Nozaki, 2007). It is considered that methylmercaptan might relate to the conversion of phenolic hydroxyl group into quinone and the subsequent formation of thio ether with benzene ring due to the nucleophilic addition of methylthio group (Hiramoto et al, 2006)
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