As part of this study on the isolation of cholinesterase inhibitors from natural marine products, the bioactivity of the ethanolic extracts from 27 Korean seaweeds were screened using acetylcholinesterase (AChE) and butyrylcholinesterase (BChE) inhibitory assays. Ecklonia stolonifera exhibited promising inhibitory properties against both AChE and BChE. Bioassay-guided fractionation of the active n-hexane and ethyl acetate (EtOAc) soluble fractions, obtained from the ethanolic extract of E. stolonifera, resulted in the isolation of the sterols; fucosterol (1) and 24-hydroperoxy 24-vinylcholesterol (2), from the n-hexane fraction and the phlorotannins; phloroglucinol (3), eckstolonol (4), eckol (5), phlorofucofuroeckol-A (6), dieckol (7), triphlorethol-A (8), 2-phloroeckol (9) and 7-phloroeckol (10), from the EtOAc fraction. Of these, compounds 2, 9 and 10 were isolated from E. stolonifera for the first time. Compounds 4-7, 9 and 10 exhibited inhibitory potential against AChE, with 50% inhibition concentration (IC50) values of 42.66 Ϯ 8.48, 20.56 Ϯ 5.61, 4.89 Ϯ 2.28, 17.11 Ϯ 3.24, 38.13 Ϯ 4.95 and 21.11 Ϯ 4.16 mM, respectively; whereas, compounds 1, 2, 4 and 6 were found to be active against BChE, with IC50 values of 421.72 Ϯ 1.43, 176.46 Ϯ 2.51, 230.27 Ϯ 3.52 and 136.71 Ϯ 3.33 mM, respectively. It has been suggested that the inhibition of these enzymes by the sterols and phlorotannins derived from marine brown algae could be a useful approach for the treatment of Alzheimer's disease.
As part of our study of the isolation of antihypertensive agents derived from natural marine products, the bioactivity of 10 edible Korean seaweeds were screened by angiotensin converting enzyme (ACE) inhibitory and peroxynitrite assays. Among the crude extracts of selected seaweeds, including five Phaeophyta ( Ecklonia stolonifera , E. cava , Pelvetia siliquosa , Hizikia fusiforme , and Undaria pinnatifida ), four Rhodophyta ( Gigartina tenella , Gelidium amansii , Chondria crassicaulis , and Porphyra tenera ) and one Chlorophyta ( Capsosiphon fulvescens ), the ethanol extracts of E. stolonifera , E. cava , P. siliquosa , U. pinnatifida , and G. tenella exhibited significant inhibitory properties against ACE at more than 50% inhibition at a concentration of 163.93 µ g/mL. Phloroglucinol 1 , eckstolonol 2 , eckol 3 , phlorofucofuroeckol A 4 , and dieckol 5 had been isolated previously, and triphlorethol-A 6 and fucosterol 7 were isolated for the first time from E. stolonifera. Also, the ACE inhibitory and peroxynitrite scavenging properties of phlorotannins 1-6 were evaluated, along with fucosterol 7 obtained from E. stolonifera . Among profound peroxynitrite scavenging compounds 1-6 , phlorotannins 3 , 4 and 5 were also determined to manifest marked inhibitory activity against ACE, with 50% inhibition concentration (IC 50 ) values of 70.82 ± 0.25, 12.74 ± 0.15, and 34.25 ± 3.56 µ M, respectively.
We conducted this study to isolate novel anti-hyperlipidemic agents derived from natural marine products. To accomplish this, we investigated the effects of ethanolic (EtOH) extracts of Ecklonia stolonifera and its phlorotannin constituents, eckol and dieckol, on serum lipid levels in rats with hyperlipidemia that was induced by a high-cholesterol diet or poloxamer 407. Treatment with the EtOH extracts of E. stolonifera and its phlorotannin-rich ethyl acetate (EtOAc) and n-butanol (n-BuOH) fractions induced a significant reduction in triglycerides (TG), total cholesterol (TC), and low-density lipoprotein-cholesterol (LDL-C) levels, as well as a significant increase in the high-density lipoprotein-cholesterol (HDLC) level in hyperlipidemic rats. However, treatment with the water (H(2)O) fraction did not exert any significant effects on the serum levels of hyperlipidemic rats. In addition, eckol and dieckol isolated from the active EtOAc fraction induced a significant reduction in serum TG, TC, and LDL-C levels, as well as in the atherogenic index (A.I.). Furthermore, treatment with dieckol induced a greater decrease in the serum TG, TC, and LDL-C levels of hyperlipidemic rats than eckol or lovastatin, as well as an increase in the serum HDL-C levels. Taken together, these results suggest that phlorotannins such as eckol and dieckol have the potential for use for the prevention of hyperlipidemic atherosclerosis.
Amyloid beta peptide (Aβ) oligomers increase intracellular reactive oxygen species (ROS) and calcium cation (Ca(2+)) concentrations, which causes neuronal cell death in Alzheimer's disease (AD). Thus, the use of neuroprotective agents with antioxidative activity might be effective in the treatment of AD. In the present study, the neuroprotective effects of the methanol extract from edible brown alga Eisenia bicyclis (Laminariaceae) and its solvent soluble fractions together with the isolated phlorotannins on Aβ-induced toxicity were assessed by cell viability, intracellular ROS, and Ca(2+) levels in PC12 cells. The addition of the methanol extract as well as its ethyl acetate and n-butanol fractions of E. bicyclis markedly reversed the Aβ-induced toxicity. Among six phlorotannins, including phloroglucinol (1), dioxinodehydroeckol (2), eckol (3), phlorofucofuroeckol A (4), dieckol (5), and 7-phloroeckol (6), isolated from the most active ethyl acetate fraction, 3-6 significantly decreased Aβ-induced cell death. Furthermore, these compounds also inhibited intracellular ROS generation and Ca(2+) generation, indicating the neuroprotective effects may be mediated through reduced intracellular ROS and Ca(2+) generation. Thus, the results of the present study imply that E. bicyclis and its active components attenuated the oxidative stress and reduced neuronal cell death, suggesting that it may be used as a dietary neuroprotective agent in AD.
Deacetylation of chitin under autoclaving conditions (15 psi/121 degrees C) was evaluated for the preparation of chitosan under different NaOH concentrations and reaction times. Deacetylation was effectively achieved by treatment of chitin under elevated temperature and pressure with 45% NaOH for 30 min and a solids/solvent ratio of 1:15. Treated chitosan showed similar nitrogen content (7.42%), degree of deacetylation (90.4%), and molecular mass (1560 kDa) but significantly higher viscosity values (2025 cP) compared with those (7.40%, 87.6%, 1304 kDa, and 143 cP, respectively) of a commercial chitosan. Reduction of the solids/solvent ratio from 1:15 to 1:10 did not affect degree of deacetylation, viscosity, and molecular mass of chitosan.
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