• Title, Summary, Keyword: phloroglucinol

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The Screening of Nitrite Scavenging Effect of Marine, Algae and Active Principles of Ecklonia Stolonifera

  • CHOI Jae Sue;LEE Ji Hyeon;JUNG Jee Hyung
    • Korean Journal of Fisheries and Aquatic Sciences
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    • v.30 no.6
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    • pp.909-915
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    • 1997
  • The nitrite scavenging effect of methanol extracts of marine algae were evaluated to discover new natural nitrite scavengers. Among the tested seaweeds, Ecklonia stolonifera, an edible brown algae, showed the strongest scavenging effect. The MeOH extract was then sequentially partitioned into $CH_2Cl_2,\;CH_2Cl_2$ insoluble interface, EtOAc, n-BuOH, and $H_2O$ layers. The EtOAc and n-BuOH fraction demonstrated high levels of nitrite-scavenging activity while the $CH_2Cl_2,\;CH_2Cl_2$ insoluble interface, and $H_2O$ fractions were inactive. A column chromatography of the EtOAc fraction through silica gel and Sephadex LH-20 yielded phloroglucinol and a new compound tentatively named phlorotannin A. The nitrite scavenging activity of phloroglucinol $(IC_{50}=3.9{\mu}g/ml)$ was more potent than that of L-ascorbic acid $(IC_{50}=65.0{\mu}g/ml)$. However, phlorotannin A $(IC_{50}=193.2{\mu}g/ml)$ showed only low levels of activity. From the above results, it is possible to suggest that both the MeOH extract and their fractions and isolated phloroglucinol and phlorotannin A obtained from E. stolonifera may be applicable as scavengers of nitrite, which is a precursor for the formation of carcinogenic N-nitroso compounds.

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Effect of TIBA, PCIB and phloroglucinol on somatic embryo maturation and germination in Japanese larch (Larix leptolepis) (낙엽송의 체세포배 발생 및 발아에 미치는 TIBA, PCIB 및 phloroglucinol의 효과)

  • Kim, Yong-Wook;Moon, Heung-Kyu
    • Journal of Plant Biotechnology
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    • v.36 no.3
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    • pp.230-235
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    • 2009
  • The effect of auxin transport inhibitor (TIBA and PCIB) or auxin synergist (phloroglucinol) on somatic embryo maturation and germination in Japanese larch (Larix leptolepis) was examined. The addition of 15.8 mg/L ABA+5.0 mg/L PCIB showed most promoted the maturation of cotyledon -staged somatic embryos (177.7/90 mg ESM). In contrast, with treatment of 5.0 mg/L PCIB or 5.0 mg/L TIBA, no somatic embryos were obtained. Considering from this result, PCIB or TIBA alone could not substitute for exogenously supplied ABA for maturation of somatic embryos. In the test of below concentration of 5.0 mg/L PCIB, the highest results were recorded in 15.8 mg/L ABA+2.0 mg/L PCIB (109.3/90 mg ESM) or 15.8 mg/L ABA+5.0 mg/L PCIB (103.7/90 mg ESM). However, 5.0 mg/L phloroglucinol (0/90 mg ESM) or no ABA addition (3/90 mg ESM) had little influence on somatic embryos maturation. In germination study, the highest frequency of plantlet regeneration obtained from the somatic embryos which had matured on 15.8 mg/L ABA+5.0 mg/L PCIB (67.9%). However, either 5.0 mg/L PCIB nor 5.0 mg/L TIBA resulted in obtained from plantlets.

Identification of Phenolic Antioxidative Components in Crataegus pinnatifida Bunge (산사 항산화성 물질의 분리 및 동정)

  • Kim, Jeong-Sook;Lee, Gee-Dong;Kwon, Joong-Ho;Yoon, Hyung-Sik
    • Applied Biological Chemistry
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    • v.36 no.3
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    • pp.154-157
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    • 1993
  • Based upon the antioxidative effectiveness of ether extracts of defated Crataegus pinnatifida B., phenolic antioxidative components were separated by gel column chromatography and identified by MS and H-NMR. Two or three individual compounds were found in free, soluble and insoluble bound phenolic acids, respectively and they were identified as caffeic acid, protocatechuic acid, phloroglucinol and pyrogallol.

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Antioxidative Effectiveness and Oxidized Products in Mixture of Methyl Linoleate and Phenolic Compounds (Methyl Linoleate에 대한 Phenol성 물질의 항산화성과 산화 생성물)

  • Kim, Jeong-Sook;Lee, Gee-Dong;Kwon, Joong-Ho;Yoon, Hyung-Sik
    • Korean Journal of Food Science and Technology
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    • v.25 no.4
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    • pp.379-385
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    • 1993
  • Antioxidative effectiveness and oxidized products in mixture of methyl linoleate(ML) and phenolic compounds were investigated under oxygen blowing at $37^{\circ}C$ for 9 days. Caffeic acid (3,4-dihydroxy cinnamate ; CML) and phloroglucinol(1,3,5-trihydroxy benzene ; PML) showed higher antioxidative effectiveness for methyl linoleate than 0.05% ${\alpha}-tocopherol$ (TML). Oxidized products in ML group were methyl 8-(2-furyl)-octanoate, 9,13-trans, cis hydroperoxide isomer, 9,13-trans, trans hydroperoxide isomer, and 9-TMSO-12,13-epoxy-10-octadecenoate. In CML group the oxidized products were methyl-8-(2-furyl)-octanoate, 9-trans, cis hydroperoxide isomer and 9-trans, trans hydroperoxide isomer, but 13-hydroxy isomer was not identified. It was shown that CML were oxidized more slowly than ML group and at 6th day of oxidation, caffeic quinone was found to be major oxidized product of caffeic acid. Oxidixed Products in PML group were methyl-8-(2-furyl)-octanoate, 9-trans, cis hydroperoxide isomer, and 9-trans, trans hydroperoxide isomer but phloroglucinol was not oxidized even at the 9th day of reaction.

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Inhibitory Effects of the Methanolic Extract of an Edible Brown Alga, Ecklonia stolonifera and Its Component, Phloroglucinol on Aflatoxin $B_1$ Mutagenicity In Vitro (Ames Test) and on Benzo(a)pyrene or N-Methyl N-nitrosourea Clastogenicity In Vivo (Mouse Micronucleus Test)

  • Lee, Ji-Hyeon;Kim, Nam-Deuk;Choi, Jae-Sue;Kim, Young-Jin;Heo, Moon-Young;Lim, Sun-Young;Park, Kun-Young
    • Natural Product Sciences
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    • v.4 no.2
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    • pp.105-114
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    • 1998
  • The antimutagenic activity of a methanol extract of Ecklonia stolonifera (Laminariaceae) against aflatoxin $B_1\;(AFB_1)$ was demonstrated with the Salmonella typhimurium assay. The numbers of revertants per plate decreased significantly when this extract was added to the assay system using S. Salmonella typhimurium TA100. The methanol extract also exhibited significant inhibitory effects on the micronuclei formation in mouse peripheral blood reticulocytes and the DNA damage in mouse spleen lymphocytes induced by N-methyl-N-nitrosourea (MMU) and benzo(a)pyrene (B(a)P). The MeOH extract was then sequentially partitioned with $CH_2Cl_2,\;CH_2Cl_2$ insoluble intermediate, EtOAc, n-BuOH, and $H_2O$. All fractions possessed antimutagenic activity but the $H_2O$ fraction was inactive. Among active fractions, the EtOAc and $CH_2Cl_2$ insoluble intermediate fractions showed the highest activity. Column chromatography using $SiO_2$ and Sephadex LH-20 yielded phloroglucinol from the EtOAc fraction. Phloroglucinol also demonstrated significant antimutagenic activity, and inhibitory effects on the micronuclei formation in mouse peripheral blood reticulocytes and DNA damage in mouse spleen lymphocytes induced by MMU and B(a)P.

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Tyrosinase Inhibitors Isolated from the Edible Brown Alga Ecklonia stolonifera

  • Kang, Hye-Sook;Kim, Hyung-Rak;Byun, Dae-Seok;Son, Byeng-Wha;Nam, Taek-Jeong;Choi , Jae-Sue
    • Archives of Pharmacal Research
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    • v.27 no.12
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    • pp.1226-1232
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    • 2004
  • Extracts from seventeen seaweeds were determined for tyrosinase inhibitory activity using mushroom tyrosinase with L-tyrosine as a substrate. Only one of them, Ecklonia stolonifera OKAMURA (Laminariaceae) belonging to brown algae, showed high tyrosinase inhibitory activity. Bioassay-guided fractionation of the active ethyl acetate (EtOAc) soluble fraction from the methanolic extract of E. stolonifera, led us to the isolation of phloroglucinol derivatives [phloroglucinol (1), eckstolonol (2), eckol (3), phlorofucofuroeckol A (4), and dieckol (5)]. Compounds 1~5 were found to inhibit the oxidation of L-tyrosine catalyzed by mushroom tyrosinase with $IC_{50}$ values of 92.8, 126, 33.2, 177, and 2.16 ${\mu}g$ /mL, respectively. It was compared with those of kojic acid and arbutin, well-known tyrosinase inhibitors, with $IC_{50}$ values of 6.32 and 112 ${\mu}g$ / mL, respectively. The inhibitory kinetics analyzed from Lineweaver-Burk plots, showed compounds 1 and 2 to be competitive inhibitors with $K_i$ of $2.3{\times}10^{-4}\;and\;3.1{times}10^{-4}$ M, and compounds 3~5 to be noncompetitive inhibitors with $K_i$ of $1.9{\times}10^{-5},\;1.4{\times}10^{-3}\;and\;1.5{\times}10^{-5}$ M, respectively. This work showed that phloroglucinol derivatives, natural compounds found in brown algae, could be involved in the control of pigmentation in plants and other organisms through inhibition of tyrosinase activity using L-tyrosine as a substrate.

Protective effect of phloroglucinol against gamma radiation-induced oxidative stress in hair follicles (방사선으로 인한 산화적 손상에서 phloroglucinol의 모낭 보호 효과)

  • Kim, Areum;Bing, So Jin;Cho, Jinhee;Herath, KHINM;Jeon, You-Jin;Lee, Byung-Gul;Park, Jae-Woo;Jee, Youngheun
    • Korean Journal of Veterinary Research
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    • v.56 no.1
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    • pp.29-35
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    • 2016
  • When exposed to gamma-rays, hair follicular cells immediately go through apoptosis, which hampers their rapid differentiation essential for the regeneration of hair. Phloroglucinol (PG) is a phenolic compound of Ecklonia cava, brown algae abundant in Jeju island, Korea. Containing plentiful polyphenols, PG is known for its instructive effects by inhibiting apoptosis, scavenging oxygen radicals, and protecting cells against oxidative stress. In this study, we demonstrate that PG rescues radiosensitive hair follicular cells from gamma radiation-induced apoptosis and DNA damage. To identify protective capacity of PG on hair follicles, we irradiated with 8.5 Gy (1.5 Gy/min) of gamma-rays to the whole body of C57BL/6 mice at day 6 after depilation with or without PG. In mice exposed to radiation, the expression of proapoptotic molecule p53 was downregulated in the skin of PG treated group. On immunohistochemical observation of the skin, PG inhibited the immunoreactivity of p53 and cleaved caspase-3. PG treatment protected hair follicular cells from cell death due to gamma-radiation. Our results suggest that PG presents radioprotective effects by inhibiting apoptosis of radiosensitive hair follicular cells and can protect hair follicular cells from gamma-ray induced damage.

Evaluation of antioxidant properties of a new compound, pyrogallol-phloroglucinol-6,6'-bieckol isolated from brown algae, Ecklonia cava

  • Kang, Sung-Myung;Lee, Seung-Hong;Heo, Soo-Jin;Kim, Kil-Nam;Jeon, You-Jin
    • Nutrition Research and Practice
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    • v.5 no.6
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    • pp.495-502
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    • 2011
  • In this study, antioxidant and free radical scavenging activities of the natural antioxidative compound, pyrogallol-phloroglucinol-6,6'-bieckol (PPB) isolated from brown algae, Ecklonia cava was assessed in vitro by measuring the radical scavenging activities (DPPH, alkyl, hydroxyl, and superoxide) using electron spin resonance (ESR) spectrometry, intracellular reactive oxygen species (ROS) scavenging activity, and DNA damage assay. According to the results of these experiments, the scavenging activity PPB against difference radicals was in the following order: DPPH, alkyl, hydroxyl, and superoxide radicals ($IC_{50}$; 0.90, 2.54, 62.93 and $109.05{\mu}M$). The antioxidant activities of PPB were higher than that of the commercial antioxidant, ascorbic acid. Furthermore, PPB effectively inhibited DNA damage induced by $H_2O_2$. These results suggest that the natural antioxidative compound, PPB, can be used by the natural food industry.

The Antioxidant Activity of Ecklonia stolonifera

  • Lee, Ji-Hyeon;Park, Jong-Cheol;Choi, Jae-Sue
    • Archives of Pharmacal Research
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    • v.19 no.3
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    • pp.223-227
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    • 1996
  • The antioxidant activity of Ecklonia stolonifera was determined by measuring lipid peroxide produced when a mouse liver homogenate was exposed to the air at $37^{\circ}C$ using 2-thiobarbituric acid (TBA) and the radical scavenging effect on 1,1-diphenyl-2-picrylhydrazyl (DPPH) radical. The methanol extract of Ecklonia stolonifera showed strong antioxidant activity. And the methanol extract was fractionated with several solvents. With regard their fractions, the antioxidative activity were in the order of ethyl acetate>dichloromethane insoluble intermediated phase>dichloromethane>n-butanol>water fraction. The ethyl acetate soluble fraction exhibiting the strongest antioxidant activity was further purified by repeated silica gel and Sephadex LH-20 column chromatography. Antioxidant phloroglucinol was isolated and identified by$ ^1H-NMR\; and\; ^{13}C-NMR$. Its antioxidant activity was simlilar to that of L-ascorbic acid.

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