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Jaboticabin and flavonoids from the ripened fruit of black rasberry (Rubus coreanum)

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Abstract

The ethyl acetate (EtOAc) layer of ripened fruits of black raspberry (Rubus coreanum) had higher DPPH radical scavenging activity than was detected in other layers. Six phenolic compounds were purified and isolated from the EtOAc layer of ripened black raspberry fruits via octadecyl silane (ODS)-column chromatography and amide column-HPLC using a guided DPPH radical scavenging assay. These compounds were identified as 4-hydroxybenzoic acid (1), 2-O-(3′,4′-dihydroxybenzoyl)-4,6-dihydroxyphenylmethylacetate (2, jaboticabin), phloridzin (3), kaempferol 3-O-β-d-glucopyranoside (4), quercetin 3-O-β-d-glucuronic acid methyl ester (5), and quercetin (6), based on MS and NMR analysis. Three compounds (1, 5, and 6) had been identified previously in this plant, but other compounds (2–4) were newly isolated from this plant. Compound 2, 5, and 6 evidenced higher DPPH radical scavenging activity than α-tocopherol at the same concentration.

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References

  1. Eu GS, Chung BY, Bandopadhyay R, Yoo NH, Choi DC, Yun SY. Phylogenic relationships of Rubus species revealed by randomly amplified polymorphic DNA markers. J. Crop Sci. Biotech. 11: 39–44 (2008)

    Google Scholar 

  2. Park JH, Lee HS, Mun HC, Kim DH, Seong NS, Jung HG, Bang JK, Lee HY. Effect of ultrasonification process on enhancement of immuno-stimulatory activity of Ephedera sinica Stapf and Rubus coreanus Miq. Korean J. Biotechnol. Bioeng. 19: 113–117 (2004)

    Google Scholar 

  3. Kim SJ, Lee HJ, Park KH, Rhee CO, Lim IJ, Chung HJ, Moon JH. Isolation and identification of low molecular phenolic antioxidants from ethylacetate layer of Korean black raspberry (Rubus coreanus) wine. Korean J. Food Sci. Technol. 40: 129–134 (2008)

    Google Scholar 

  4. Lee MK, Lee HS, Choi GP, Oh DH, Kim JD, Yu CY, Lee HY. Screening of biological activities of the extracts from Rubus coreanus Miq. Korean J. Med. Crop Sci. 11: 5–12 (2003)

    Google Scholar 

  5. Cha HS, Park MS, Park KM. Physiological activities of Rubus coreanus Miquel. Korean J. Food Sci. Technol. 33: 409–415 (2001)

    Google Scholar 

  6. Yoon I, Cho JY, Kook JH, Wee JH, Jang MY, Ahn TH, Park KH. Identification and activity of antioxidative compounds from Rubus coreanum fruit. Korean J. Food Sci. Technol. 34: 898–904 (2002)

    Google Scholar 

  7. Yoon I, Wee JH, Ahn TH, Park KH. Isolation and identification of quercetin with antioxidative activity from the fruits of Rubus coreanum Miquel. Korean J. Food Sci. Technol. 35: 499–502 (2003)

    Google Scholar 

  8. Chung TH, Kim JC, Lee CY, Moon MK, Chae SC, Lee IS, Kim SH, Hahn KS, Lee IP. Potential antiviral effects of Terminalia chebula, Sanguisorba officinalis, Rubus coreanus, and Rheum palmatum against duck hepatitis B virus (DHBV). Phytother. Res. 11: 179–182 (1997)

    Article  Google Scholar 

  9. Ohtani K, Miyajima C, Takahasi T, Kasai R, Tanaka O, Hahn DR, Naruhashi N. A dimeric triterpene-glycoside from Rubus coreanus. Phytochemistry 29: 3275–3280 (1990)

    Article  CAS  Google Scholar 

  10. Kim YH, Kang SS. Triterpenoids from Rubi fructus (bogbunja). Arch. Pharm. Res. 16: 109–113 (1993)

    Article  CAS  Google Scholar 

  11. Lee YA, Lee MW. Tannins from Rubus coreanum. Korean J. Pharmacogn. 26: 27–30 (1995)

    CAS  Google Scholar 

  12. Pang GC, Kim MS, Lee MW. Hydrolyzable tannins from the fruits of Rubus coreanum. Korean J. Pharmacogn. 27: 366–370 (1996)

    CAS  Google Scholar 

  13. Choi JW, Lee KT, Ha JH, Yun SY, Ko CD, Jung HJ, Park HJ. Antinociceptive and anti-inflammatory effects of niga-ichigoside F1 and 23-hydroxytormentic acid obtained from Rubus coreanus. Biol. Pharm. Bull. 26: 1436–1441 (2003)

    Article  CAS  Google Scholar 

  14. Nam JH, Jung HJ, Choi JW, Lee KT, Park HJ. The anti-gastropathic and anti-rheumatic effect of niga-ichigoside F1 and 23-hydroxytormentic acid isolated from the ripe fruits of Rubus coreanus in a rat model. Biol. Pharm. Bull. 29: 967–970 (2006)

    Article  CAS  Google Scholar 

  15. Abe N, Nemoto A, Tsuchiya Y, Hojo H, Hirota A. Studies of the 1,1-diphenyl-2-picrylhydrazyl radical scavenging mechanism for a 2-pyrone compound. Biosci. Biotech. Bioch. 64: 306–333 (2000)

    Article  CAS  Google Scholar 

  16. Takao T, Kitatani F, Watanabe N, Yagi A, Sakata K. A simple screening method for antioxidants and isolation of several antioxidants produced by marine bacteria from fish and shellfish. Biosci. Biotech. Bioch. 58: 1780–1783 (1994)

    Article  CAS  Google Scholar 

  17. Cho JY, Ji SH, Moon JH, Lee KH, Jung KH, Park KH. A novel benzoyl glucoside and phenolic compounds from the leaves of Camellia japonica. Food Sci. Biotechnol. 17: 1060–1065 (2008)

    CAS  Google Scholar 

  18. Foo LY, Newman R, Waghorn G, Mcnabb WC, Ulyatt MJ. Proanthocyanidins from Lotus corniculatus. Phytochemistry 41: 617–624 (1996)

    Article  CAS  Google Scholar 

  19. Nawwar MAM, Souleman AMA, Buddrus J, Linscheid M. Flavonoids from the flowers of Tamarix nilotica. Phytochemistry 23: 2347–2349 (1984)

    Article  CAS  Google Scholar 

  20. Neamati N, Hong H, Mazumder A, Wang S, Sunder S, Nicklaus MC, Milne GWA, Proksa B, Pommier Y. Depsides and depsidones as inhibitors of HIV-1 intergrase: Discovery of novel inhibitors through 3D database searching. J. Med. Chem. 40: 942–951 (1997)

    Article  CAS  Google Scholar 

  21. Reynertson KA, Wallace AM, Adachi S, Gil RR, Yang H, Basile MJ, D’Armiento J, Weinstein BW, Kenelly EJ. Bioactive depsides and anthocyanins from jaboticaba (Myrciaria cauliflora). J. Nat. Prod. 69: 1228–1230 (2006)

    Article  CAS  Google Scholar 

  22. Kim SJ, Cho JY, Wee JH, Jang MY, Kim C, Rim YS, Shin SC, Ma SJ, Moon JH, Park KH. Isolation and characterization of antioxidative compounds from the aerial parts of Angelica keiskei. Food Sci. Biotechnol. 14: 58–63 (2005)

    CAS  Google Scholar 

  23. Wee JH, Moon JH, Eun JB, Chung JH, Kim YG, Park KH. Isolation and identification of antioxidants from peanut shells and the relationship between structure and antioxidant activity. Food Sci. Biotechnol. 16: 116–122 (2007)

    CAS  Google Scholar 

  24. Kim MS, Pang GC, Lee MW. Flavonoids from the leaves of Rubus coreanum. Yakhak Hoeji 41: 1–6 (1997)

    CAS  Google Scholar 

  25. Turner A, Chen SN, Nikolic D, van Breemen R, Farnswort NR, Pauli GF. Coumaroyl iridoids and a depside from cranberry (Vaccinium macrocarpon). J. Nat. Prod. 70: 253–258 (2007)

    Article  CAS  Google Scholar 

  26. Wurms KV, Cooney JM. Isolation of a new phenolic compound, 3,5-dihydroxy-2-(methoxycarbonylmethyl) 3,4-dihydroxbenzoate, from leaves of Axtinidia chinensis (kiwifruit). Asian J. Biochem. 1: 325–332 (2006)

    Article  CAS  Google Scholar 

  27. Yamamoto N, Moon JH, Tsushida T, Nagao A, Terao J. Inhibitory effect of quercetin metabolites and their related derivatives on copper-induced lipid peroxidation in human low-density lipoprotein. Arch. Biochem. Biophys. 372: 347–354 (1999)

    Article  CAS  Google Scholar 

  28. Ueda H, Yamazaki C, Yamazaki M. A hydroxyl group of flavonoids affects oral anti-inflammatory activity and inhibition of systemic tumor necrosis factor-a production. Biosci. Biotech. Bioch. 68: 199–125 (2004)

    Article  Google Scholar 

  29. Murakami A, Ashida H, Terao J. Multitargeted cancer prevention by quercetin. Cancer Lett. 269: 315–325 (2003)

    Article  Google Scholar 

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Cho, JY., Yoon, I., Jung, DH. et al. Jaboticabin and flavonoids from the ripened fruit of black rasberry (Rubus coreanum). Food Sci Biotechnol 21, 1081–1086 (2012). https://doi.org/10.1007/s10068-012-0140-z

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  • DOI: https://doi.org/10.1007/s10068-012-0140-z

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