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Official Journal of the Japan Wood Research Society

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Antioxidant compounds from Eucalyptus grandis biomass by subcritical liquid water extraction

Abstract

The effectiveness of subcritical liquid water processing for extraction of antioxidants from the leaves of Eucalyptus grandis biomass was evaluated by determining the capability of the processed samples to scavenge peroxynitrite radicals in vitro, as compared with the extracts obtained by conventional extraction. Pyrogallol (1), 5-hydroxymethyl-2-furaldehyde (2), and 4,4,6,6-tetramethyl-3,5-dioxo-cyclohex-1-enecarboxylic acid (3) were identified as the major products obtained from the subcritical liquid water extracts. Among these, pyrogallol (1) exhibited stronger antioxidant activity than butylated hydroxytoluene, which was used as a standard for the antioxidant activity measurement.

References

  1. Elliot WR, Jones DL (1986) Encyclopedia of Australian plants suitable for cultivation, vol 4. Lothian, Melbourne

    Google Scholar 

  2. Lassak EV, McCarthy T (1983) Australian medicinal plants. Methuen, Sydney

    Google Scholar 

  3. Boland DJ, Brophy JJ (1991) Eucalyptus leaf oils: use, chemistry, distillation and marketing. Inkata, Melbourne

    Google Scholar 

  4. Ghisalberti EL (1996) Bioactive acylphloroglucinol derivatives from Eucalyptus species. Phytochemistry 41:7–22

    Article  CAS  PubMed  Google Scholar 

  5. Yamashita N, Etoh H, Sakata K, Ina H, Ina K (1989) New acylated rhaponticin isolated from Eucalyptus rubida as a repellent against the blue mussel, Mytilus edulis. Agric Biol Chem 53:2827–2829

    CAS  Google Scholar 

  6. Nishizawa M, Emura M, Kan Y, Yamada H, Ogawa K, Hamanaka N (1992) Macrocarpals: HIV-RTase inhibitors of Eucalyptus globules. Tetrahedron Lett 33:2983–2986

    Article  CAS  Google Scholar 

  7. Murata M, Yamakoshi Y, Homma S, Arai K, Nakamura Y (1992) Macrocarpals, antibacterial compounds from Eucalyptus inhibit aldose reductase. Biosci Biotech Biochem 56:2062–2063

    Article  CAS  Google Scholar 

  8. Osawa T, Namiki M (1981) A novel type of antioxidant isolated from leaf wax of Eucalyptus species. Agric Biol Chem 46:735–739

    Google Scholar 

  9. Takasaki M, Konoshima T, Shingu T, Tokuda H, Nishino H, Iwashima A, Kozuka M (1990) Structures of euglobals-G1,-G2, and-G3 from Eucalyptus grandis, three new inhibitors of Epstein Barr virus activation. Chem Pharm Bull 38:1444–1446

    Article  CAS  PubMed  Google Scholar 

  10. Yoshida S, Asami T, Kawano T, Yoneyama K, Crow WD, Paton DM, Takahashi N (1988) Photosynthetic inhibitors in Eucalyptus grandis. Phytochemistry 27:1943–1946

    Article  CAS  Google Scholar 

  11. Lee SM, Na MK, An RB, Min BS, Lee HK (2003) Antioxidant activity of two phloroglucinol derivatives from Dryopteris crassirhizoma. Biol Pharm Bull 26:1354–1356

    Article  CAS  PubMed  Google Scholar 

  12. Athanasas K, Magiatis P, Fokialakis N, Skaltsounis AL, Pratsinis H, Kletsas D (2004) Hyperjovinols A and B: two new phloroglucinol derivatives from Hypericum jovis with antioxidant activity in cell cultures. J Nat Prod 67:973–977

    Article  CAS  PubMed  Google Scholar 

  13. Kruse A, Dinjus E (2007) Hot compressed water as reaction medium and reactant: properties and synthesis reactions. J Supercrit Fluid 39:362–380

    Article  CAS  Google Scholar 

  14. Pongnaravane B, Goto M, Sasaki M, Anekpankul T, Pavasant P, Shotipruk A (2006) Extraction of anthraquinones from roots of Morinda citrifolia by pressurized hot water: antioxidant activity of extracts. J Supercrit Fluid 37:390–396

    Article  CAS  Google Scholar 

  15. Rodriguez-Meizoso I, Marin FR, Herrero M, Senorans FJ, Reglero G, Cifuentes A, Ibanez E (2006) Subcritical water extraction of nutraceuticals with antioxidant activity from Oregano. Chemical and functional characterization. J Pharm Biomed Anal 41:1560–1565

    Article  CAS  PubMed  Google Scholar 

  16. Ibañez E, Kubátová A, Señoráns FJ, Cavero S, Reglero G, Hawthorne SB (2003) Subcritical water extraction of antioxidant compounds from rosemary plants. J Agric Food Chem 51:375–382

    Article  PubMed  Google Scholar 

  17. Niwa T, Doi U, Kato Y, Osawa T (2001) Antioxidative properties of phenolic antioxidants isolated from corn steep liquor. J Agric Food Chem 49:177–182

    Article  CAS  PubMed  Google Scholar 

  18. Jimenez-Carmona MM, Luque de Castro MD (1999) Isolation of eucalyptus essential oil for GC-MS analysis by extraction with subcritical water. Chromatographia 50:578–582

    Article  CAS  Google Scholar 

  19. Andre-Barres C, Najjar F, Bottalla AL, Massou S, Zedde C, Baltas M, Gorrichon L (2005) Fe(II)-induced reduction of labelled endoperoxides. NMR degradation studies on G3 factor and its methyl ether. J Org Chem 70:6921–6924

    Article  CAS  PubMed  Google Scholar 

  20. Smith RM, Burgess RJ (1996) Superheated water — a clean eluent for reversed-phase high-performance liquid chromatography. Anal Commun 33:327–329

    Article  CAS  Google Scholar 

  21. Rovio S, Hartonen K, Holm Y, Hiltunen R, Riekkola ML (1999) Extraction of clove using pressurized hot water. Flavour Frag J 14:399–404

    Article  CAS  Google Scholar 

  22. Fagerson IS (1969) Thermal degradation of carbohydrates: a review. J Agric Food Chem 17:747–750

    Article  CAS  Google Scholar 

  23. Bolte ML, Crow WD, Yoshida S (1982) Plant growth regulators in Eucalyptus grandis. Reaction of the G-regulators with nucleophiles. Aust J Chem 35:1431–1437

    Article  CAS  Google Scholar 

  24. Kalsi PS, Singh J, Crow WD, Chhabra BR (1987) Biometric synthesis of 2,3-dioxabicyclo (4,4,0) decanes as plant growth regulators. Phytochemistry 26:3367–3369

    Article  CAS  Google Scholar 

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Correspondence to Hideo Etoh.

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This research was presented at the conference of the Japan Society for Bioscience, Biotechnology, and Agrochemistry (JSBBA) in Tokyo, March 2007.

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Kulkarni, A., Suzuki, S. & Etoh, H. Antioxidant compounds from Eucalyptus grandis biomass by subcritical liquid water extraction. J Wood Sci 54, 153–157 (2008). https://doi.org/10.1007/s10086-007-0916-6

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  • DOI: https://doi.org/10.1007/s10086-007-0916-6

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