Deodorizing Effects of Phlorotannins from Edible Brown Alga Eisenia bicyclis on Methyl Mercaptan

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 IC 50 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.

The Quest for Phenolic Compounds from Macroalgae: A Review of Extraction and Identification Methodologies

“…Thus, the use of either RP-SPE or RP-HPLC combined with NP-CC provides two dimensions of separation that, in many cases, replace the need for column approaches. Nonetheless, some studies have reported the use of RP-CC of phlorotannins [32,76,151,159,172,177,178,182] or coumarins and phenolic acids [21], mostly with octadecyl-derivatized stationary phases. This matrix is the most widespread RP phase since it provides excellent resolution for a wide variety of organic compounds while using aqueous and low toxicity polar solvents for elution (instead of the hydrophobic ones associated with NP-CC, which are costly, toxic, and polluting).…”

“…At last, size exclusion chromatography (SEC-CC) using Sephadex LH-20 has been repeatedly used in the fractionation of macroalgae polar extracts [60,76,77,88,115,151,156,157,174,175,[177][178][179][180][181][182]. The separation of compounds in Sephadex LH-20 is promoted by the metabolites' molecular size, but also by its solubility in the eluent.…”

“…Although has being a technique used to analyze crude extracts or fractions, in order to confirm the reliability of spectrophotometric analysis (as discussed above), NMR has been also used in the identification (or confirmation) of isolated phenolic compounds [21,27,156,176], as well as of isolated phlorotannins [32,33,43,45,46,60,62,73,101,115,116,153,154,[177][178][179]184,189,207,[215][216][217]. In fact, NMR analysis has allowed to identify different groups of isolated phlorotannins, in particular, phlorethols, fuhalols, fucols, fucophlorethols, and eckols [32,33,40,43,45,46,60,62,73,153,154,[177][178][179]184,207,[215][216][217].…”

“…Although 1 H NMR and/or 13 C NMR have been always used in macroalgae phenolic compounds identification, some authors have complemented their analysis with two-dimensional NMR (2D NMR), namely. heteronuclear multiple-quantum correlation (HMQC), heteronuclear multiple-bond correlation (HMBC), 1 H-1 H rotating frame nuclear overhauser effect spectroscopy (ROESY), or 1 H-1 H correlation spectroscopy (COSY) [32,40,62,73,115,177,178,184,207].…”

Deodorization films based on polyphenol compound‐rich natural deodorants and polycaprolactone for removing volatile sulfur compounds from kimchi

“…Various fruits and vegetables have been shown to lower the levels of volatiles (Mirondo & Barringer, 2016). Particularly, the deodorizing activity of natural polyphenols has been extensively evaluated (Kida et al., 2002; Kim et al., 2013; Lodhia et al., 2008; Makhotkina & Kilmartin, 2010; Munch & Barringer, 2014; Negishi et al., 2002; Negishi et al., 2004; Yasuda, & Arakawa, 1995). Green tea extract (GTE), black tea extract (BTE), and grape seed extract (GSE) contain high concentrations of flavonoids, such as catechins, and other polyphenol compounds with numerous reported beneficial effects on health (Gibis et al., 2016; Otton et al., 2018; Pan et al., 2016).…”