Browse > Article

Peroxynitrite scavengers from Phellinus linteus  

Jeong, Da-Mi (Division of Food Science and Biotechnology, Pukyong National University)
Jung, Hyun-Ah (Division of Food Science and Biotechnology, Pukyong National University)
Kang, Hye-Sook (Division of Food Science and Biotechnology, Pukyong National University)
Choi, Jae-Sue (Division of Food Science and Biotechnology, Pukyong National University)
Publication Information
Natural Product Sciences / v.14, no.1, 2008 , pp. 1-11 More about this Journal
Abstract
Peroxynitrite ($(ONOO^-)$ is a cytotoxic species formed from nitric oxide and superoxide anion, which are highly implicated in the pathogenesis of oxidative stress-mediated diseases. The aim of this study was to investigate the scavenging effects of Phellinus linteus on authentic $ONOO^-$, and further phytochemical studies are planned that will attempt to identify the active principles. From the active EtOAc fraction, a mixture of fungisterol and 5-dihydroergosterol (1), a mixture of betulin and 1,2-benzenedicarboxylic acid bis (2-methyl heptyl) ester (2), protocatechualdehyde (3), protocatechuic acid (4), cirsiumaldehyde (5), hispidin (6), caffeic acid (7), phelligridin D (8), uracil (9), gallic acid (10), 2,5-dihydroxybenzoic acid (11), ferulic acid (12), 2,3-dihydroxybenzaldehyde (13), arbutin (14), isoferulic acid (15), guanosine (16), and ellagic acid (17) were isolated, and their structures were characterized based on spectroscopic data. All compounds except 3, 6, 7 and 16 were isolated for the first time from P. linteus. Compounds 3, 4, 6-8, 10-15, and 17 showed potent scavenging activity on $ONOO^-$, with $IC_{50}$ values of $2.06\;{\pm}\;0.10$, $3.45\;{\pm}\;0.57$, $0.71\;{\pm}\;0.05$, $2.78\;{\pm}\;0.36$, $5.42\;{\pm}\;0.26$, $1.13\;{\pm}\;0.02$, $1.82\;{\pm}\;0.17$, $0.91\;{\pm}\;0.19$, $1.59\;{\pm}\;0.09$, $1.88\;{\pm}\;0.07$, $1.22\;{\pm}\;0.37$, and $2.01\;{\pm}\;0.02\;{\mu}M$, respectively, as compared to the positive control, DL-penicillamine, with an $IC_{50}$ value of $5.04\;{\pm}\;0.06\;{\mu}M$.
Keywords
Phellinus linteus; peroxynitrite scavengers;
Citations & Related Records
Times Cited By KSCI : 9  (Citation Analysis)
Times Cited By SCOPUS : 1
연도 인용수 순위
1 Kim, D.H., Choi, H.J., and Bae, E.A., Effect of artificially cultured Phellinus linteus on harmful intestinal bacterial enzymes and rat intestinal a-glucosidases. J. Food Hyg. Safety 13, 20-23 (1998)
2 Klotz, L.O. and Sies, H., Defenses against peroxynitrite: selenocompounds and flavonoids. Toxicol. Lett. 140, 125-132 (2003)   DOI   ScienceOn
3 Lee, S.H., Shim, S.H., Kim, J.S., and Kang, S.S., Constituents from the fruiting bodies of Ganoderma applanatum and their aldose reductase inhibitory activity. Arch. Pharm. Res. 29, 479-483 (2006a)   과학기술학회마을   DOI   ScienceOn
4 Okai, Y. and Higashi-Okai, K., Radical-scavenging activity of hot water extract of Japanese rice bran-association with phenolic acids. J. UOEH. 28, 1-12 (2006)   DOI   PUBMED
5 Pannala, A., Rice-Evans, C.A., Halliwell, B., and Singh, S., Inhibition of peroxynitrite mediated tyrosine nitration by catechin polyphenols. Biochem. Biophy. Res. Commun. 232, 164-168 (1997)   DOI   ScienceOn
6 Pannala, A., Razaq, R., Halliwell, B., Singh S, and Rice-Evans, C.A., Inhibition of peroxynitrite dependent tyrosine nitration by hydroxycinnamates: Nitration or electron donation? Free Radic. Biol. Med. 24, 594-606 (1998)   DOI   ScienceOn
7 Pozharitskaya, O.N., Ivanova, S.A., Shikov, A.N., Makarov, V.G., and Galambosi, B., Separation and evaluation of free radical-scavenging activity of phenol components of green, brown, and black leaves of Bergenia crassifolia by using HPTLC-DPPH method. J. Sep. Sci. 30, 2447-2452 (2007)   DOI   ScienceOn
8 Shon, Y.H. and Nam, K.S., Antimutagenicity and induction of anticarcinogenic phase II enzymes by basidiomycetes. J. Ethnopharmacol. 77, 103-109 (2001)   DOI   ScienceOn
9 Darley-Usmar, V., Wiseman, H., and Halliwell, B., Nitric oxide and oxygen radicals: a question of balance. FEBS Lett. 369, 131-135 (1995)   DOI   ScienceOn
10 Han, S.B., Lee, C.W., Kang, J.S., Yoon, Y.D., Lee, K.H., Lee, K., Park, S. K., and Kim, H.M., Acidic polysaccharide from Phellinus linteus inhibits melanoma cell metastasis by blocking cell adhesion and invasion. Int. Immunopharmacol. 6, 697-702 (2006)   DOI   ScienceOn
11 Ikekawa, T., Nakanish, M., Uehara, N., Chihara, G., and Fukuoka, F., Antitumor action of some Basidiomycetes, especially Phellinus linteus. Gann. 59, 155-157 (1968)
12 Kerry, N. and Rice-Evans, C.A., Inhibition of peroxynitrite-mediated oxidation of dopamine by flavonoid and phenolic antioxidants and their structural relationships. J. Neruochem. 73, 247-253 (1999)   DOI
13 Cho, J.H., Cho, S.D., Hu, H., Kim, S.H., Lee, S.K., Lee, Y.S., and Kang, K.S., The roles of ERK 1/2 and p38 MAP kinases in the preventive mechanisms of mushroom Phellinus linteus against the inhibition of gap junctional intercellular communication by hydrogen peroxide. Carcinogenesis 23, 1163-1169 (2002)   DOI   ScienceOn
14 Cha, B.C., Lee, H.W., and Rhim, T.J., Antioxidnat constituents and activities of acorn hull and chestnut hull. Yakhak Hoeji 47, 212-217 (2003)
15 Sies, H. and Masumoto, H., Ebselen as a glutathione peroxidase mimic and as a scavenger of peroxynitrite. Adv. Pharmacol. 38, 229-246 (1997)   PUBMED
16 Aoki, T., Takagi, K., Hirata, T., and Suga, T., Two naturally ocuuurring acyclic diterpene and norditerpene aldhydes from Tetragonia tetragonoides. Phytochemistry 21, 1361-1363 (1982)   DOI   ScienceOn
17 Kooy, N.W., Royall, J.A., Ischiropoulos, H., and Beckman, J.S., Peroxynitrite-mediated oxidation of dihydrorhodamine 123. Free Radic. Biol. Med. 16, 149-156 (1994)   DOI   ScienceOn
18 Sun, L.X., Fu, W.W., Ren, J., Xu, L., Bi, K.S., and Wang, M.W., Cytotoxic constituents from Solanum lyratum. Arch. Pharm. Res. 29, 135-139 (2006)   DOI   ScienceOn
19 Tipoe, G.L., Leung, T. M., Hung, M. W., and Fung, M. L., Green tea polyphenols as an anti-oxidant and anti-inflammatory agent for cardiovascular protection. Cardiovasc. Hematol. Disord. Drug Targets. 7, 135-144 (2007)   DOI   ScienceOn
20 Yun-Choi, H.S., Pyo, M.K., and Park, K.M., Cirsiumaldehyde from Gastrodia elata, Nat. Prod. Sci. 3, 104-105 (1997)   과학기술학회마을
21 Salah, N., Miller, N.J., Paganga, G., Tijburg, L., Bolwell, G.P., and Rice- Evans, C., Polyphenolic flavanols as scavengers of aqueous phase radicals and as chain-breaking antioxidants. Arch. Biochem. Biophys. 322, 339-346 (1995)   DOI   ScienceOn
22 Lee, I.K., Jung, J.Y., Seok, S.J., Kim, W.G., and Yun, B.S., Free radical scavengers from the medicinal mushroom Inonotus xeranticus and their proposed biogenesis. Bioorg. Med. Chem. Lett. 16, 5621-5624 (2006b)   DOI   ScienceOn
23 Song, S.S., Kim, S.H., Sa, J.H., Jin, C., Lim, C.J., and Park, E.H., Antiangiogenic, antioxidant and xanthine oxidase inhibition activities of the mushroom Phellinus linteus. J. Ethnopharmocol. 88, 113-116 (2003)   DOI   ScienceOn
24 Han, S.B., Lee, C.W., Jeon, Y.J., Hong, N.D., Yoo, I.D., Yang, K.H., and Kim, H.M., The inhibitory effect of polysaccharides isolated from Phellinus linteus on tumor growth and metastasis. Immunopharmacol. 41, 157-164 (1999)   DOI   ScienceOn
25 Aruoma, O.I., Spencer, J.P., and Mahmood, N., Protection against oxidative damage and cell death by the natural antioxidant ergothioneine. Food Chem. Toxicol. 37, 1043-1053 (1999)   DOI   ScienceOn
26 Nakamura, T., Matsugo, S., Uzuka, Y., Matsuo, S., and Kawagishi, H., Fractionation and anti-tumor activity of the mycelia of liquid-cultured Phellinus linteus. Biosci. Biotechnol. Biochem. 68, 868-872 (2004)   DOI   ScienceOn
27 Park, H.W., Baek, N.I., Kim, S.H., Kwon, B.M., Chung, I.S., Park, M.H., Kim, S.H., and Kim, D.K., Phytochemical components from the whole plants of Arabis glabra (L.) Bernh. Kor. J. Pharmacogn. 35, 320-323 (2004c)   과학기술학회마을
28 Park, W.Y., Lee, S.C., Ahn, B.T., Lee, S.H., Ro, J.S., and Lee, K.S., Phenolic compounds from Acaloha australis L. Kor. J. Pharmacogn. 24, 20-24 (1993)
29 Rosecke, J. and Konig, W.A., Constituents of various wood-rotting basidiomycetes. Phytochemistry 54, 603-610 (2000)   DOI   ScienceOn
30 Mo, S., Wang, S., Zhou, G., Yang, Y., Li, Y., Chen, X., and Shi, J., Phelligridins D-F: cytotoxic pyrano[4,3-c][2]benzopyran-1,6-dione and furo[3,2-c]pyran-4-one derivatives from the fungus Phellinus igniarius. J. Nat. Prod. 67, 823-828 (2004)   DOI   ScienceOn
31 Choi, C.W., Jung, H.A., Kang, S.S., and Choi, J.S., Antioxidant constituents and a new triterpenoid glycoside from Flos lonicerae. Arch. Pharm. Res. 30, 1-7 (2007)   DOI   ScienceOn
32 Park, I.H., Jeon, S.Y., Lee, H.J., Kim, S.I., and Song, K.S., A betasecretase (BACE1) inhibitor hispidin from the mycelial cultures of Phellinus linteus. Planta Med. 70, 143-146 (2004a)   DOI   ScienceOn
33 Singh, N., Mahmood, U., Kaul, V.K., and Jirovetz, L., A new phthalic acid ester from Ajuga bracteosa. Nat. Prod. Res. 20, 593-597 (2006)   DOI   ScienceOn
34 Im, K.R., Jeong, T.S., Kwon, B.M., Baek, N.I., Kim, S.H., and Kim, D.K., Acyl-CoA: Cholesterol acyltransferase inhibitors from Llex macropoda. Arch. Pharm. Res. 29, 191-194 (2006)   DOI   ScienceOn
35 Kooy, N.W., Royall, J.A., Ye, Y.Z., Kelly, D.R., and Beckman, J.S., Evidence for in vivo peroxynitrite production in human acute lung injury. Am. J. Respir. Crit. Care Med. 151, 1250-1254 (1995)   PUBMED
36 Sandoval, M., Zhang, X.J., Liu, X., Mannick, E.E., Clark, D.A., and Miller, M.J., Peroxynitrite-induced apoptosis in T84 and RAW 264.7 cells: attenuation by L-ascorbic acid. Free Radic. Biol. Med. 22, 489- 495 (1997)   DOI   ScienceOn
37 Park, I.H., Chung, S.K., Lee, K.B., Yoo, Y.C., Kim, S.K., Kim, G.S., and Song, K.S., An antioxidant hispidin from the mycelial cultures of Phellinus linteus. Arch. Pharm. Res. 27, 615-618 (2004b)   과학기술학회마을   DOI   ScienceOn
38 Rice-Evans, C.A., Miller, N.J., and Paganga, G., Structure-antioxidant relationships of flavonoids and phenolic acids. Free Radic. Biol. Med. 20, 933-956 (1996)   DOI   ScienceOn
39 Kim, H.G., Yoon, D.H., Lee, W.H., Han, S.K., Shrestha, B., Kim, C.H., Lim, M.H., Chang, W., Lim, S., Choi, S., Song, W.O., Sung, J.M., Hwang, K.C., and Kim, T.W., Phellinus linteus inhibits inflammatory mediators by suppressing redox-based NF-kappaB and MAPKs activation in lipopolysaccharide-induced RAW 264.7 macrophage. J. Ethnopharmacol. 114, 307-315 (2007)   DOI   ScienceOn
40 Virag, L., Szabo, E., Gergely, P., and Szabo, C., Peroxynitrite-induced cytotoxicity: mechanism and opportunities for intervention. Toxicol. Lett. 140, 113-124 (2003)   DOI   ScienceOn
41 Szabo, C., The role of peroxynitrite in the pathophysiology of shock, inflammation and ischemia-reperfusion injury. Shock 6, 79-88 (1996)   DOI   ScienceOn
42 Nishida, J. and Kawabata, J., DPPH radical scavenging reaction of hydroxyl- and methoxychalcones. Biosci. Biotechnol. Biochem. 70, 193-202 (2006)   DOI   ScienceOn
43 Kang, H.S., Choi, J.H., Cho, W.K., Park, J.C., and Choi, J.S., A sphingolipid and tyrosinase inhibitors from the fruiting body of Phellinus linteus. Arch. Pharm. Res. 27, 742-750 (2004)   과학기술학회마을   DOI   ScienceOn
44 Lee, Y.S., Lee, H.S., Shin, K.H., Kim, B.K., and Lee, S.H., Constituents of the Halophyte Salicornia herbacea. Arch. Pharm. Res. 27, 1034- 1036 (2004)   DOI   ScienceOn
45 Hur, J.M., Yang, C.H., Han, S.H., Lee, S.H., You, Y.O., Park, J.C., and Kim, K.J., Antibacterial effect of Phellinus linteus against methicillinresistant Staphylococcus aureus. Fitoterapia 75, 603-605 (2004)   DOI   ScienceOn
46 Min, B.S., Yun, B.S., Lee, H.K., Jung, H.J., Jung, H.A., and Choi, J.S., Two novel furan derivatives from Phellinus linteus with anticomplement activity. Bioorg. Med. Chem. Lett. 16, 3255-3257 (2006)   DOI   ScienceOn
47 Pryor, W. and Squadrito, G., The chemistry of peroxynitrite: a product from the reaction of nitric oxide with superoxide. Am. J. Physiol. 268, 699-722 (1996)
48 Hamauzu, Y., Inno, T., Kume, C., Irie, M., and Hiramatsu, K., Antioxidant and antiulcerative properties of phenolics from Chinese quince, quince, and apple fruits. J. Agric. Food Chem. 54, 765-772 (2006)   DOI   ScienceOn
49 Huh, J., Dong-Eui-Bo-Gam, Namsandang Press, Seoul, 1981, p. 26
50 Rhee, Y.K., Han, M.J., Park, S.Y., and Kim, D.H., In vitro and In vivo antitumor activity of the fruit body of Phellinus linteus. Korean J. Food Sci. Technol. 32, 477-480 (2000)
51 Beckman, J.S., Beckman, T.W., Chen, J., Marshall, P.A., and Freeman, B.A., Apparent hydroxyl radical production by peroxynitrite: Implication for endothelial injury from nitric oxide and superoxide. Proc. Nat. Acad. Sci. 87, 1620-1624 (1990)
52 Lim, E.K., Higgins, G.S., Li, Y., and Bowles, J., Regioselectivity of glucosylation of caffeic acid by a UDP-glucose:glucosyltransferase is maintained in planta. Biochem. J. 373, 987-992 (2003)   DOI   ScienceOn
53 Guo, J., Zhu, T., Collins, L., Xiao, Z.X., Kim, S.H., and Chen, C.Y., Modulation of lung cancer growth arrest and apoptosis by Phellinus linteus. Mol. Carcinog. 46, 144-154 (2007)   DOI   ScienceOn
54 Hisatomi, E., Matsui, M., Kubota, K., and Kobayashi, A., Antioxidative activity in the pericarp and seed of Japanese pepper (Xanthoxylum piperitum DC). J. Agric. Food Chem. 48, 4924-4928 (2000)   DOI   ScienceOn
55 Kim, J.E., Kim, A.R., Chung, H.Y., Han, S.Y., Kim, B.S., and Choi, J.S., In vitro peroxynitrite scavenging activity of diarylheptanoids from Curcuma longa. Phytother. Res. 17, 481-484 (2003)   DOI   ScienceOn
56 Shin, J.Y., Lee, S., Bae, I.Y., Yoo, S.H., and Lee, H.G., Structural and biological study of c arboxymethylated Phellinus linteus polysaccharides. J. Agric. Food Chem. 55, 3368-3372 (2007)   DOI   ScienceOn
57 Boersma, B.J., Patel, R.P., Kirk, M., Jackson, P.L., Muccio, D., Darley- Usmar, V.M., and Barnes, S., Chlorination and nitration of soy isoflavones. Arch. Biochem. Biophys. 368, 265-275 (1999)   DOI   ScienceOn
58 Pollard, S.E., Kuhnle, G.G., Vauzour, D., Vafeiadou, K., Tzounis, X., Whiteman, M., Rice-Evans, C., and Spencer, J.P., The reaction of flavonoid metabolites with peroxynitrite. Biochem. Biophys. Res. Commun. 350, 960-968 (2006)   DOI   ScienceOn
59 Teijeira, M., Santana, L., and Uriarte, E., Assignment of the $^{13}C$-NMR spectra of some adenine, hypoxanthine and guanine carbonucleosides. Magn. Reson. Chem. 35, 806-807 (1997)   DOI   ScienceOn
60 Ho, S.C., Tsai, T.H., Tsai, P.J., and Lin, C.C., Protective capacities of certain spices against peroxynitrite-mediated biomolecular damage. Food Chem. Toxicol. 30, Epub ahead of print (2007)