• Fisheries and Aquatic Sciences
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• v.14 no.3
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• pp.198-204
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• 2011

The brown seaweed Ecklonia cava is known to be a rich source of phlorotannins that have diverse biological activities. Among the phlorotannins in E. cava, concentrations of dieckol and phlorofucofuroeckol-A, which were identified as major active components, were determined in different parts of the tissue. We compared the efficacy of different pretreatments for their extraction. A high-performance liquid chromatography (HPLC) method to determine phlorotannin concentrations showed good accuracy (92.64 and 94.02%, respectively), precision (3.92 and 3.94%, respectively), and linearity (r>0.996). Mature thalli contained 1.5-fold more dieckol (1.82 mg/g-dry tissue) than young thalli. In the tissues of E. cava, blade tissue contained more phlorotannins than the stipe or holdfast. Among differently dried thalli, approximately 90% or more dieckol and phlorofucofuroeckol-A were extracted from shadow-dried tissue as compared with lyophilized tissue. In sun-dried and oven-dried thalli, approximately 60% of the phlorotannins were extracted. Thalli washed with fresh water, boiled thalli, and steamed thalli showed reduced extraction of the compounds.

• Journal of Marine Bioscience and Biotechnology
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• v.1 no.2
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• pp.126-135
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• 2006

Phlorotannins which is oligomeric polyphenol of phloroglucinol unit were isolated from solvent fractions of methanolic extract of the brown alga, Ecklonia cava (EC). The inhibitory effects of phlorotannins from EC solvent fractions on oxidative stress were examined in human dermal fibroblasts (HDFs) related to wrinkle formation. Among the solvent fractions, phlorotannins from ethyl acetate fraction exerted the highest scavenging effect on DPPH radical, hydroxyl radical and alkyl radical analyzed by electron spin resonance (ESR) spectroscopy. The levels of intracellular reactive oxygen species (ROS) and lipid peroxidation were measured using 2',7'-dichlorofluorescin diacetate (DCFH-DA) and diphenyl-1-pyrenylphosphine (DPPP), respectively. Their levels were significantly decreased in the presence of phlorotannins from ethyl acetate fraction, compared with other fractions obtained from EC extract (P < 0.01). Furthermore, intracellular glutathione (GSH) level was significantly increased in a time dependent manner by the phlorotannins. Therefore, these results suggest that phlorotannins from EC extract could have a therapeutic potential for prevention and treatment of several diseases such as wrinkle formation related to oxidative stress.

• Fisheries and Aquatic Sciences
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• v.18 no.2
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• pp.165-171
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• 2015

Abalone containing phlorotannins is produced by feeding the phlorotannin-rich brown seaweed Eisenia bicyclis after 4 days of starvation. Reverse-phase high-performance liquid chromatography (RP-HPLC) was used to isolate and quantify phlorotannins, which were identified by mass spectrometry and [$^1H$]-nuclear magnetic resonance to be the P1 compound, 7-phloroeckol, and eckol. When E. bicyclis was used as feed, P1 compound accumulated to an average of 1.60 mg/g dry weight of abalone muscle tissue after 18 d, 7-phloroeckolol to 0.21 mg/g after 16 d, and eckol to 0.22 mg/g after 12 d. Saccharina japonica was used as a control feed, and the abalone showed little or no accumulation of phlorotannins in muscle tissue. Feed consumption and growth rate were very similar when either E. bicyclis or S. japonica was fed for 20 d. Half-maximal reductions in the levels of P1 compound, 7-phloroeckol, and eckol accumulation were attained in 1.5, 1.9, and 3.4 days, respectively, after the feed was switched from E. bicyclis to S. japonica. Value-added abalone containing bioactive phlorotannins can be produced by simply changing the feed to the phlorotannin-rich E. bicyclis 18 d prior to harvesting.

• Korean Journal of Fisheries and Aquatic Sciences
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• v.47 no.4
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• pp.356-362
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• 2014

Phlorotannins, the major constituent in brown algae, possess various biological activities; however, there is little information their toxicological effects. To assess the safety of phlorotannins, we investigated the acute oral toxicity of a high-purity phlorotannin preparation (PRT; total phlorotannin content 90%) in beagle dogs. Six beagle dogs (3 males, 3 females) were assigned randomly to three experimental groups. PRT was administered at oral doses of 250, 500, and 750 mg/kg by capsule. Vomiting by male and female beagles was observed with 500 and 750 mg/kg on the first day. In addition, one beagle given 750 mg/kg had soft stool and diarrhea on days 3 and 13. No deaths or abnormal clinical signs were observed during the experiment. All groups showed similar body weight gain and food consumption. Our acute toxicity study showed that PRT did not cause any toxicological effects in beagle dogs.

• ALGAE
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• v.27 no.1
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• pp.9-19
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• 2012

Phlorotannins are common metabolites produced in kelps that can have deterrent functions against grazers. The factors dictating seasonal patterns of phlorotannin content in northeastern Pacific kelps are not well understood. This study assessed density and grazing of the gastropod Lacuna vincta on the annual canopy-forming kelp Nereocystis luetkeana and the perennial understory species Agarum clathratum, Saccharina latissima and S. groenlandica in Kachemak Bay, Alaska. In addition, we assessed seasonal patterns of environmental variables as possible drivers of phlorotannin concentrations. Phlorotannins occurred in all species, with overall lowest levels in N. luetkeana, and with different seasonal patterns among the four species. Lacuna vincta was most dense on N. luetkeana thalli in the summer and had highest grazing rates on this low-phlorotannin species. However, correlations between L. vincta density and phlorotannin content of each kelp species were not significant. Except for N. luetkeana, there were no correlations between phlorotannin levels and environmental variables. We suggest that kelp life history traits may be more important for phlorotannin patterns in these kelp species than grazers or environmental drivers.

• Journal of Life Science
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• v.25 no.7
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• pp.780-785
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• 2015

Dietary intake and bioavailability of phorotannins in abalone was investigated after feeding with the phlorotannin-rich brown seaweed Ecklonia stolonifera after 4 days starvation. Reverse-phase high-performance liquid chromatography (RP-HPLC) affords isolation and quantification of the major phlorotannins of 7-phloroeckol and eckol, which were identified by mass spectrometry and nuclear magnetic resonance. Abalone growth and feed consumption rates were similar when fed either with the E. stolonifera or the common feed seaweed Saccharina japonica for 20 days. Throughout the feeding period, 7-phloroeckolol was accumulated in the abalone flesh tissue up to an average of 0.58±0.13 mg/g dry weight after 6 days. Eckol was reached to 0.25±0.05 mg/g dry tissue after 6 days, and maintained the level until end of feeding period. By feeding S. japonica as a control, no phlorotannins were detected in the abalone tissues. Both of the abalone, fed with E. stolonifera or S. japonica, had enzymes that decomposed 7-phloroeckol and eckol in muscle tissues, with similar degradation rates of −0.05 or less and −0.05 mg/ml/hr, respectively. Phlorotannins were reduced by constitutive enzymes in abalone tissues. Therefore, value-added abalone containing bioactive phlorotannins can be produced by simply changing the feed to the phlorotannin-rich brown seaweed E. stolonifera 6 days before harvest.

• Korean Journal of Pharmacognosy
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• v.37 no.2 s.145
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• pp.92-96
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• 2006

Six phlorotannins were isolated from Ecklonia cava, a brown alga belonging to Alariaceae, collected offshore Jeju Island. Among the phlorotannins, dieckol showed strong elastase inhibition and hyaluronidase ingibition.

• ALGAE
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• v.30 no.3
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• pp.241-246
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• 2015

This research was conducted to develop effective and safe marine-derived antiviral compounds against norovirus. The ethyl acetate (EtOAc)-extract from Eisenia bicyclis exhibited strong antiviral activity against murine norovirus (MNV) as a norovirus surrogate. Among the phlorotannins from E. bicyclis, dieckol (DE) and phlorofucofuroeckol-A (PFF) were known to possess the strongest antibacterial activity. In this study, DE and PFF were evaluated for antiviral activity against MNV. DE and PFF exhibited strong anti-MNV activity with 50% effective concentration ($EC_{50}$) of $0.9{\mu}M$. However, PFF exhibited more effective antiviral activity against MNV with higher selective index (668.87) than that of DE (550.60), due to its lower cell toxicity against RAW 264.7. This is the first report on the anti-MNV activity of phlorotannins from seaweed. The results obtained in this study suggest that the phlorotannins could be used as a potential source of natural antiviral agents.

• ALGAE
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• v.20 no.1
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• pp.69-75
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• 2005

Hizikia fusiformis is well known edible brown seaweed both in Korea and Japan. It has been intensively studied due to its pronounced health benefits. In this study, the radical scavenging (antioxidative) activities of its hydrophilic phlorotannin constituents were studied. An aqueous extract/original extract (OE) of H. fusiformis was initially prepared with heat, enzymes and pH control treatments. Then the original extract was further fractionated (with methylene chloride and methanol) and crude hydrophilic phlorotannin extract (CHPE) was prepared. The radical scavenging activities of both OE and CHPE were determined by using electron spin resonance (ESR) spectrophotometric assays such as 1,1-diphenyl-2-picrylhydrazyl (DPPH), hydroxyl and alkyl radical assays. The CHPE reported significantly (p < 0.05) higher total phenolic (phlorotannins) content (1.23 mg ${\cdot}ml^{-1}$) than that of the OE (0.21 mg ${\cdot}ml^{-1}$). Both OE and CHPE have reported good radical scavenging activities and those activities were dose-dependent. The CHPE have demonstrated significantly higher radical scavenging activities than that of the OE. In comparison, the DPPH radical (6 $\times$ 10$^{-5}$ M) scavenging activities of all the CHPE concentrations (0.25, 0.5 and 1 mg ${\cdot}ml^{-1}$) tested were significantly higher (37.3, 78.2 and 91.6%, respectively) than that of the OE counterparts (11.4, 34.6 and 61.7%, respectively). Alkyl radical scavenging percentages of CHPE at 0.0625, 0.125, 0.25 and 0.5 mg${\cdot}ml^{-1}$ were significantly higher (34.3, 69.2, 80.4 and 88.7%, respectively) than that of the OE (16.6, 41.4, 62.3 and 77.4%, respectively). The percentages of hydroxyl radical scavenging activities of CHPE at the concentrations of 0.25, 0.5 and 1 mg ${\cdot}ml^{-1}$ were 32.5, 59.4 and 84.2 % respectively. Moreover, the hydroxyl radical scavenging activity of OE was quite lower than that of the CHPE. Therefore, these results suggest that the hydrophilic phlorotannins of H. fusiformis are potential radical scavengers thus, a great source of antioxidative nutraceuticles.

• Fisheries and Aquatic Sciences
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• v.16 no.1
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• pp.1-5
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• 2013

To assess the feasibility of phlorotannins from Eisenia bicyclis as cancer chemopreventative agents, we tested whether they induced quinone reductase (QR) in Hepa1c1c7 cells. The ethyl acetate (EtOAc) soluble fraction obtained from E. bicyclis exhibited a QR induction activity in Hepa1c1c7 cells. Successive column chromatography of the active EtOAc fraction resulted in the isolation of four phlorotannins. Their structures were elucidated using one- and two-dimensional nuclear magnetic resonance spectroscopic techniques and characterized as phloroglucinol (1), dioxinodehydroeckol (2), dieckol (3), and fucofuroeckol-A (4). Among these compounds, fucofuroeckol-A (4) showed moderate QR induction activity, and dioxinodehydroeckol (2) exhibited potent QR induction potency with $2.05{\pm}0.04$ fold induction at a concentration of $50{\mu}M$ compared to the dimethyl sulfoxide solvent-treated control cells. However, phloroglucinol (1) and dieckol (3) exerted no detectable QR induction activity in Hepa1c1c7 cells. These results suggest that dioxinodehydroeckol could serve as a useful cancer chemopreventive chemical.