Abstract
The roots of Broussonetia papyrifera were extracted into four different polar solvents: chloroform, 50% ethanol in water, ethanol, and water. The ethanol extract showed the most potent inhibition (72.3% at 20 g/mL) against xanthine oxidase (XOD). Chromatography of EE yielded nine phenolic phytochemicals, which were confirmed as broussochalcone A (1), broussochalcone B (2), 3,4-dihydroxyisolonchocarpin (3), 4-hydroxyisolonchocarpin (4), 3-′(3-methylbut-2-enyl)-3′,4′,7-trihydroxyflavane (5), kazinol A (6), kazinol B (7), kazinol E (8), and broussoflavan A (9). All isolated compounds (19) possessed potent antioxidant activities against 2,2-diphenyl-l-picrylhydrazyl and 2,2′-azino-bis-ethylbenzthiazoline-6-sulfonic acid (ABTS) radicals with IC50 values ranging from 5.8 to 252.8M. Although most compounds exhibited potent inhibition with IC50 values ranging 0.6–164 M against XOD, compounds 1 and 3 were found to be the principal contributors to the XOD inhibition in ethanol extract. The analysis of K I and K IS values proved that the two most promising compounds (1 and 3), present at high concentrations in the root barks as analyzed by using high-performance liquid chromatography analysis, were reversible mixed type I inhibitors.
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References
Blois MA (1958) Antioxidant determination by the use of a stable free radical. Nature 181, 1199–1200.
Chen RM, Hu LH, An TY, Li J, and Shen Q (2002) Natural PTP1B inhibitors from Broussonetia papyrifera. Bioorg Med Chem Lett 12, 3387–3390.
Chiari ME, Vera DMA, Palacios SM, and Carpinella MC (2011) Tyrosinase inhibitory activity of a 6-isoprenoid-substituted flavanone isolated from Dalea elegans. Bioorg Med Chemt 19 3474–3482.
Choi SY, Chung MJ, Seo WD, Shin JH, Shon MY, and Sung NJ (2006) Inhibitory effects of Orostachys japonicas extracts on the formation of N-nitrosodimethylamine. J Agric Food Chem 54, 6075–6078.
Dagne E, Bekele A, and Waterman PG (1989) The flavonoids of Millettia ferruginea subsp. ferruginea and subsp. darassana in Ethiopia. Phytochemistry 28, 1897–1900.
Fang SC, Shieh BJ, and Lin CN (1994) Phenolic constituents of Formosan Broussonetia papyrifera. Phytochemistry 37, 851–853.
Fellegrin N, Ke R, Yang M, and Rice EC (1999) Screening of dietary carotenoids and carotenoid-rich fruit extracts for antioxidant activities applying 2,2′-azinobis(3-ethylbenzothiazoline-6-sulfonic acid) radical cation decolorization assay. Methods Enzymol 299, 379–389.
Filho RB, Gottiieb OR, Mourao AP, Rocha AID, and Oliveira FS (1975) Flovonoids from Derris species. Phytochemistry 14, 1454–1456.
Fukai T and Nomura T (1985) Components of Broussonetia papyrifera (L.) Vent. I. structures of two new isoprenylated flavonols and two chalcone derivatives. Chem Pharm Bull 33, 3250–3256.
Halliwell B (1991) Drug antioxidant effects: a basis for drug selection. Drugs 42, 569–650.
Harris MD, Siegel LB, and Alloway JA (1999) Gout and hyperuricemia. Am Fam Physician 59, 925–934.
Ikauta J, Hano Y, Nomura T, Kawakami Y, and Sato T (1986) Components of Broussonetia kazinoki SIEB. I. Structure of two new isoprenylated flavans and five new isoprenylated 1,3-diphenylpropane derivatives. Chem Pharm Bull 34, 1968–1979.
Ikut J, Hano Y, and Nomura T (1985) Compounds of Broussonetia papyrifera (L.) Vent. 2. Structure of two new isoprenylated flavans, kazinols A and B. Heterocycles 23, 2835–2842.
Kim JY, Jeong HJ, Park JY, Kim YM, Park SJ, Cho JK et al. (2012) Selective and slow-binding inhibition of shikonin derivatives isolated from Lithospermum erythrorhizon on glycosyl hydrolase 33 and 34 sialidases. Bioorg Med Chem 20 1740–8.
Kong LD, Cai Y, Huang WW, Cheng CHK, and Tan RX (2000) Inhibition of xanthine oxidase by some Chinese medicinal plants used to treat gout. J Ethnopharmacol 73, 199–207.
Kramer HM and Curhan G (2002) The association between gout and nephrolithiasis: The National Health and Nutrition Examination Survey III, 1988–1994. Am J Kidney Dis 40, 37–42.
Lee JH, Baek IY, Ko JM, Kang NS, Shin SH, Lim SG et al. (2008) Antioxidant and tyrosinase inhibitory activities from seed coat of brown soybean. Food Sci Biotechnol 17, 1–7.
Lin LW, Chen HY, Wu CR, Liao PM, Lin YT, Hsieh MT et al. (2008) Comparision with various parts of Broussonetia papyrifera as to the antinociceptive and anti-inflammatory activities in rodents. Biosci Biotechnol Biochem 72, 2377–2384.
Matsumoto J, Fujimoto T, Takino C, Saitoh M, Hano Y, Fukai T et al. (1985) Components of Broussonetia papyrifera (L.) Vent. I. Structures of two new isoprenylated flavonols and two chalcone derivatives. Chem Pharm Bull 33, 3250–3256.
Ryu HW, Curtis LMJ, Jung SI, Jeong IY, Kim DS, Kang KY et al. (2012) Anticholinesterase potential of flavonols from paper mulberry (Broussonetia papyrifera) and their kinetic studies. Food Chem 132, 1244–1250.
Ryu HW, Lee BW, Curtis LMJ, Jung SI, Ryu YB, Lee WS et al. (2010) Polyphenols from Broussonetia papyrifera displaying potent aglucosidase inhibition. J Agric Food Chem 58, 202–208.
Shon HY, Son KH, Kwon CS, Kwon GS, and Kang SS (2004) Antimicrobial and cytotoxic activity of 18 prenylated flavonoids isolated from medicinal plants: Morus alba L., Morus mongolica Schneider, Broussnetia papyrifera (L.) Vent, Sophora flavescens Ait and Echinosophora koreensis Nakai. Phytomedicine 11, 666–672.
Tomita M, Mizuno S, Yamanaka H, Hosoda Y, Sakuma K, Matuoka Y et al. (2000) Does hyperuricemia affect mortality? A prospective cohort study of Japanese male workers. J Epidemiol 10, 403–409.
Yu BP (1994) Cellular defenses against damage from reactive oxygen species. Physiol Rev 74, 139–162.
Zhang PC, Wang S, Wu Y, Chen RY, and Yu DQ (2001) Five new diprenylated flavonols from the leaves of Broussonetia kazinoki. J Nat Prod 64, 1206–1209.
Zheng ZP, Cheng KW, Chao J, Wu J, and Wang M (2008) Tyrosinase inhibitors from paper mulberry (Boussonetia papyrifera). Food Chem 106, 529–535.
Zhang JP, Chen QX, Song KK, and Xie JJ (2006) Inhibitory effects of salicylic acid family compounds on the diphenolase activity of mushroom tyrosinase. Food Chem 95, 579–584.
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Ryu, H.W., Lee, J.H., Kang, J.E. et al. Inhibition of xanthine oxidase by phenolic phytochemicals from Broussonetia papyrifera . J Korean Soc Appl Biol Chem 55, 587–594 (2012). https://doi.org/10.1007/s13765-012-2143-0
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DOI: https://doi.org/10.1007/s13765-012-2143-0