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Isolation and Identification of Adenosine and Phlomuroside from the Aerial Parts of Oryza sativa L.

벼(Oryza sativa L.)의 지상부로부터 adenosine과 phlomuroside의 분리 및 동정

  • Jeong, Rak-Hun (Department of Oriental Medicinal Materials & Processing and Graduate School of Biotechnology, Kyung Hee University) ;
  • Lee, Dae-Young (Herbal Crop Utilization Research Team, National Institute of Horticultural and Herbal Science, RDA) ;
  • Cho, Jin-Gyeong (Department of Oriental Medicinal Materials & Processing and Graduate School of Biotechnology, Kyung Hee University) ;
  • Baek, Yoon-Su (Department of Oriental Medicinal Materials & Processing and Graduate School of Biotechnology, Kyung Hee University) ;
  • Seo, Kyeong-Hwa (Department of Oriental Medicinal Materials & Processing and Graduate School of Biotechnology, Kyung Hee University) ;
  • Lee, Dong-Geol (R&D center, GFC Co., Ltd.) ;
  • Kang, Hee-Cheol (R&D center, GFC Co., Ltd.) ;
  • Kim, Ji-Young (Department of Oriental Medicinal Materials & Processing and Graduate School of Biotechnology, Kyung Hee University) ;
  • Baek, Nam-In (Department of Oriental Medicinal Materials & Processing and Graduate School of Biotechnology, Kyung Hee University)
  • Received : 2014.04.15
  • Accepted : 2014.06.10
  • Published : 2014.12.31

Abstract

Fresh and chopped aerial parts of Oryza sativa were extracted in 80% aqueous mehthanol, and the concentrated extract was successively partitioned in n-hexane, ethyl acetate (EtOAc), n-butanol (n-BuOH), and $H_2O$ fractions. From the n-BuOH fraction, two compounds were isolated through repeated silica gel and ODS column chromatography (c.c.). Based on nuclear magnetic resonance (NMR), mass spectrometry and infrared spectroscopy spectroscopic data, the compounds were identified to be adenosine (1) and phlomuroside (2). Especially, the configuration of both the anomer hydroxyl groups was determined as ${\beta}$ from the coupling constants of the anomer protons (J =6.0 and 7.6 Hz) in the $^1H-NMR$ spectra. This is the first report for the isolation of these compounds from Oryza sativa L.

벼 지상부를 MeOH 수용액으로 추출하고 이 추출물을 n-hexane, EtOAc, n-BuOH, 및 $H_2O$ 분획으로 나누었다. n-BuOH 분획에 대하여 silica gel, ODS 및 Sephadex LH-20 column chromatography를 반복실시 하여 2종의 화합물을 분리하였다. NMR, IR 및 MS data를 해석하여 각각 adenosine (1)과 phlomuroside (2)로 구조 동정 하였다. 이들 화합물들은 벼에서는 처음으로 분리되었다.

Keywords

References

  1. Ardiansyah, Shirakawa H, Shimeno T, Koseki T, Shiono Y, Murayama T et al. (2009) Adenosine, an identified active component from the Driselasetreated fraction of rice bran, is effective at improving metabolic syndrome in stroke-prone spontaneously hypertensive rats. J Agric Food Chem 57, 2558-64. https://doi.org/10.1021/jf803347c
  2. Chung HS and Woo WS (2001) A quinolone alkaloid with antioxidant activity from the aleurone layer of anthocyanin-pigmented rice. J Nat Prod 64, 1579-80. https://doi.org/10.1021/np010324g
  3. Chung IM, Ali M, Ahmad A, Lim JD, Yu CY, and Kim JS (2006) Chemical constituents of rice (Oryza sativa) hulls and their herbicidal activity against Duckweed (Lemna paucicostata Hegelm 381). Phytochem Anal 17, 36-45. https://doi.org/10.1002/pca.879
  4. Chung IM, Ali M, and Ahmad A (2005) Oryzasesterpenolide from the hulls of Oryza sativa and complete NMR assignments of momilactones A, B and tricin. Asian J Chem 17, 2467-78.
  5. Ciuffreda P, Casati S, and Manzocchi A (2007) Complete $^1H$ and $^{13}C$ NMR spectral assignment of ${\alpha}$- and ${\beta}$-adenosine, 2'-deoxyadenosine and their acetate derivatives. Magn Res Chem 45, 781-4. https://doi.org/10.1002/mrc.2036
  6. Gadangi P, Longaker M, Naime D, Levin RI, Recht PA, Montesinos MC et al. (1996) The Anti-inflammatory mechanism of sulfasalazine is related to adenosine release at inflamed sites. J Immunology 156, 1937-41.
  7. Jeong RH, Lee DY, Cho JG, Lee SM, Kang HC, Seo WD et al. (2011) A New flavonolignan from the aerial parts of Oryza sativa L. inhibits NO production in RAW 264.7 macrophage cells. J Korean Soc Appl Biol Chem 54, 865-70. https://doi.org/10.3839/jksabc.2011.132
  8. Jeong RH, Lee DY, Cho JG, Seo KH, Lee JW, Lee MH et al. (2014) New flavonolignan glucoside from the aerial parts of Oryza sativa. Chem Nat Comp 49, 1003-5. https://doi.org/10.1007/s10600-014-0809-z
  9. Jun HJ, Lee JH, Cho BR, Seo WD, Kang HW, Kim DW et al. (2012) Dual inhibition of a-oryzanol on cellular melanogenesis: Inhibition of tyrosinase activity and reduction of melanogenic gene expression by a protein kinase A-dependent mechanism. J Nat Prod 75, 1706-11. https://doi.org/10.1021/np300250m
  10. Lee SC, Chung IM, Jin YJ, Song SY, Park BS, Cho KH et al. (2008) Momilactone B, an allelochemical of rice hulls, induces apoptosis on human lymphoma cells (Jurkat) in a micromolar concentration. Nutr Cancer 60, 542-51. https://doi.org/10.1080/01635580801927445
  11. Lee TB (2003) In coloured flora of Korea. HyangMunSa, Korea.
  12. Li XS, Zhou XJ, Zhang XJ, Su J, Li Xj, Yan YM et al. (2001) Sesquiterpene and norsesquiterpene derivatives from Sanicula lamelligera and their biological evaluation. J Nat Prod 74, 1521-5.
  13. Macias FA, Chinchilla N, Varela RM, and Molinillo JMG (2005) Bioactive compounds from Oryza sativa L. Steroids 71, 603-8.
  14. Moon KI, Min BS, Lee HK, and Zee OP (2002) Antioxidant compounds of Oryza sativa L. Kor J Pharmacogn 33, 173-6.
  15. Shalini V, Bhaskar S, Kumar KS, Mohanlal S, Jayalekshmy A, and Helen A (2012) Molecular mechanisms of anti-inflammatory action of the flavonoid, tricin from Njavara rice (Oryza sativa L.) in human peripheral blood mononuclear cells: possible role in the inflammatory signaling. Int Immunopharmacol 14, 32-8 https://doi.org/10.1016/j.intimp.2012.06.005
  16. Song MC, Yang HJ, Jeong TS, Kim KT, and Baek NI (2008) Heterocyclic compounds from Chrysanthemum coronarium L. and their inhibitory activity on hACAT-1, hACAT-2, and LDL oxidation. Arch Pharm Res 31, 573-8. https://doi.org/10.1007/s12272-001-1195-4
  17. Yalcin FN, Ersoz TF, Akbay P, Calis I, Donmez AA, and Sticher O (2003) Phenolic, megastigmane, nucleotide, acetophenon and monoterpene glycosides from Phlomis samia and P. carica. Turk J Chem 27, 703-11.
  18. Zhang Y, Cichewicz RH, and Nair MG (2004) Lipid peroxidation inhibitory compounds from daylily (Hemerocallis fulva) leaves. Life Sciences 75, 753-63. https://doi.org/10.1016/j.lfs.2004.03.002

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