Cytotoxic Triterpenoid from Rubus coreanus Miq

  • Lee, Dae-Young (Graduate School of Biotechnology and Plant Metabolism Research Center, Kyung Hee University) ;
  • Kim, Dong-Hyun (School of Chemistry, University of Manchester) ;
  • Bang, Myun-Ho (Graduate School of Biotechnology and Plant Metabolism Research Center, Kyung Hee University) ;
  • Song, Myoung-Chong (Graduate School of Biotechnology and Plant Metabolism Research Center, Kyung Hee University) ;
  • Kwak, Ho-Young (Graduate School of Biotechnology and Plant Metabolism Research Center, Kyung Hee University) ;
  • Yoo, Ki-Hyun (Graduate School of Biotechnology and Plant Metabolism Research Center, Kyung Hee University) ;
  • Chung, In-Sik (Graduate School of Biotechnology and Plant Metabolism Research Center, Kyung Hee University) ;
  • Kim, Kyong-Tai (Department of Life Science, Division of Molecular and Life Science, Pohang University of Science and Technology) ;
  • Baek, Nam-In (Graduate School of Biotechnology and Plant Metabolism Research Center, Kyung Hee University)
  • Published : 2007.12.31

Abstract

Dried unripe fruits of Rubus coreanus Miq. were extracted with 80% aqueous MeOH and the concentrated extract was partitioned with EtOAc and $H_2O$. From the EtOAc fraction, four triterpenoids were isolated through repeated silica gel, ODS and Sephadex LH-20 column chromatographies. From the result of physico-chemical data including NMR, MS aud IR, the chemical structures of the compounds were determined as tormentic acid (1), myrianthic acid (2), hovenic acid (3) and 2${\alpha}$,3${\beta}$,19${\beta}$,23-tetrahydroxylolean-12-en-28-oic acid (4). Compounds 3 and 4 were isolated for the first time from this plant. All isolated compounds were evaluated for cytotoxic activity against human colon carcinoma cells using in vitro three-[4,5-dimethylthiazole-2-yl]-2,5-diphenyltetrazolium bromide (MTT) assay, compound 3 showed a higher cytotoxicity ($IC_{50}$ = 7.8 ${\mu}M$) than doxorubicin ($IC_{50}$= 50 ${\mu}M$).

Keywords

References

  1. Jeung BS and Sin MK (1990) Hang Yak Dae Sa Jeun. p. 652, Young Lim Sa, Seoul, Korea
  2. Lee TB (2003) In Coloured Flora of Korea. pp. 536, Hyang Mun Sa, Seoul, Korea
  3. Perry LM and Metzger J (1980) Medicinal Plants of East and Southeast Asia, Attributed Aroperties and Uses. p. 346, Cambridge MIT Press
  4. Kim TJ (1996) Korean Resources: Plant 2. pp. 165, Seoul National University Press, Seoul, Korea
  5. Kwon KH, Cha WS, Kim DC, and Shin HJ (2006) A research and application of active ingredients in Bokbunja (Rubus coreanus Miquel). Korean J Biotechnol Bioeng 21, 405-409
  6. Kwon YW, Kim YS, Song GS, and Hong SP (2004) Quality characteristics of bread with Rubi Frutus (Rubus coeranus Miquei) Juice. Korean J Food Nutr 17, 272- 277
  7. Cha HW, Park MS, and Park KM (2001) Physiological activities of Rubus coreanus Miquel. Korean J Food Sci Tech 33, 409-415
  8. Choi J, Lee KT, Ha J, Yun SY, Ko CD, and Jung HJ (2003) Antinociceptive and antiinflammatory effects of Nigaichigoside F1 and 23-hydroxytormentic acid obtained from Rubus coreanus. Biol Pham Bull 26, 1436-1441 https://doi.org/10.1248/bpb.26.1436
  9. Pang GC, Kim MS, and Lee MW (1996) Hydrolyzable tannins from the fruits of Rubus coreanus. Korean J Pharmacogn 27, 366-370
  10. Kitajma J and Tanaka Y (1993) Constituents of Prunus zippeliana leaves and branches. Chem Pham Bull 41, 2007- 2009 https://doi.org/10.1248/cpb.41.2007
  11. Hirai N, Sugie M, Wada M, Lahlou EH, Kamo T, Yoshida R, Tsuda M, and Ohigashi H (2000) Triterpene phytoalexins from strawberry fruit. Biosci Biotech Biochem 64, 1707-1712 https://doi.org/10.1271/bbb.64.1707
  12. Yoshikawa K, Kimura Y, Kondo E, and Arihara, S (1998) A lupane-triterpene and a 3($2\rightarrow1$) abeolupane glucoside from Hovenia trichocarea. Phytochemistry 49, 2057- 2060 https://doi.org/10.1016/S0031-9422(98)00409-9
  13. Josssang A, Seuleiman M, Maidou E, and Bodo B (1996) Pentacyclic triterpenes from Combetum nigrican. Phytochemistry 41, 591-594 https://doi.org/10.1016/0031-9422(95)00641-9
  14. Ma CM, Cai SQ, Cui JR, Wang RQ, Tu PF, Hattori M, and Daneshtalab M (2005) The cytotoxic activity of ursolic acid derivatives. Eur J Med Chem 40, 582-589 https://doi.org/10.1016/j.ejmech.2005.01.001
  15. Tian Z, Lin G, Zheng RX, Huang F, Yang MS, and Xiao PG (2006) Anti-hepatoma activity and mechanism of ursolic acid and its derivatives isolated from Aralia decaisneana. World J Gastroenterol 12, 874-879 https://doi.org/10.3748/wjg.v12.i6.874