Lipophilic extractives from the bark of Eucalyptus grandis x globulus, a rich source of methyl morolate: Selective extraction with supercritical CO 2

Industrial Crops and Products

Volumn 43, Issue 1, 2013, Pages 340-348

  Patinha, D J S ^a   Domingues, R M A ^a   Villaverde, J J ^a   Silva, A M S ^b   Silva, C M ^a   Freire, C S R ^a   Neto, C Pascoal ^a   Silvestre, A J D ^a  

^a UNIVERSITY OF AVEIRO   (Portugal)

^b UNIVERSITY OF AVEIRO   (Portugal)

Author keywords

Eucalyptus grandis x globulus; Inner and outer barks; Methyl 3 hydroxyolean 18 en 28 oate; Methyl morolate; Supercritical CO 2 extraction; Triterpenic acids

Indexed keywords

GLOBULUS; INNER AND OUTER BARKS; METHYL 3-HYDROXYOLEAN-18-EN-28-OATE; METHYL MOROLATE; SUPERCRITICAL CO;

GAS CHROMATOGRAPHY; TISSUE;

CARBON DIOXIDE;

BARK; BIOCHEMICAL COMPOSITION; CARBON DIOXIDE; EVERGREEN TREE; EXTRACTION METHOD; GAS CHROMATOGRAPHY; MASS SPECTROMETRY; NUCLEAR MAGNETIC RESONANCE; PHYTOCHEMISTRY; PLANT EXTRACT; TERPENE;

PORTUGAL;

EUCALYPTUS; EUCALYPTUS GRANDIS;

EID: 84864925214     PISSN: 09266690     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.indcrop.2012.06.056     Document Type: Article

References (46)

1. Assimopoulou A.N., Papageorgiou V.P. GC-MS analysis of penta- and tetra-cyclic triterpenes from resins of Pistacia species. Part I. Pistacia lentiscus var. Chia. Biomed. Chromatogr. 2005, 19(4):285-311.
2. Barbosa L.C.A., Maltha C.R.á., Cruz M.P. Chemical composition of lipophilic and polar extractives of Eucalyptus grandis. Sci. Eng. J. 2005, 15(2):13-20.
3. Bishayee A., Ahmed S., Brankov N., Perloff M. Triterpenoids as potential agents for the chemoprevention and therapy of breast cancer. Front. Biosci. 2011, 16:980-996.
4. Budzikiewicz H., Wilson J.M., Djerassi C. Mass spectrometry in structural and stereochemical problems. 32. Pentacyclic triterpenes. J. Am. Chem. Soc. 1963, 85(22):3688.
5. Burnouf-Radosevich M., Delfel N.E., England R. Gas chromatography-mass spectrometry of oleanane-type and ursane-type triterpenes - application to chenopodium-quinoa triterpenes. Phytochemistry 1985, 24(9):2063-2066.
6. Cannon J.R., Metcalf B.W., Raston C.L., White A.H. Isolation o 3Beta-hydroxyolean-18-en-28-oic acid (morolic acid) from Eucalyptus grossa and the crysta-structure of methyl morolate acetate. Aust. J. Chem. 1981, 34(5):1134-1144.
7. 2 extracts. Ind. Crop. Prod. 2005, 21(1):65-69.
8. CELPA Boletim estatístico 2009 2010, Indústria Papeleira Portuguesa, Lisboa.
9. Choi Y.H., Kim J.W., Noh M.J., Choi F.S., Yoo K.P. Comparison of supercritical carbon dioxide extraction with solvent extraction of nonacosan-10-ol, alpha-amyrin acetate, squalene and stigmasterol from medicinal plants. Phytochem. Anal. 1997, 8(5):233-237.
10. Corma A., Iborra S., Velty A. Chemical routes for the transformation of biomass into chemicals. Chem. Rev. 2007, 107(6):2411-2502.
11. Cossalter C., Pye-Smith C. Fast-Wood Forestry: Myths and Realities 2003, Centre for International Forestry Research, Bogor, E-book available from: http://environment.yale.edu/tfd/uploads/Cossalter_and_Pye-Smith_2003.pdf (viewed April 2009).
12. Domingues R.M.A., Patinha D.J.S., Sousa G.D.A., Villaverde J.J., Silva C.M., Freire C.S.R., Silvestre A.J.D., Neto C.P. Eucalyptus biomass residues from agro-forest and pulping industries as sources of high-value triterpenic compounds. Cell. Chem. Technol. 2011, 45(7-8):475-481.
13. Domingues R.M.A., Sousa G.D.A., Freire C.S.R., Silvestre A.J.D., Neto C.P. Eucalyptus globulus biomass residues from pulping industry as a source of high value triterpenic compounds. Ind. Crop. Prod. 2009, 31(1):65-70.
14. Domingues R.M.A., Sousa G.D.A., Silva C.M., Freire C.S.R., Silvestre A.J.D., Neto C.P. High value triterpenic compounds from the outer barks of several Eucalyptus species cultivated in Brazil and in Portugal. Ind. Crop. Prod. 2011, 33(1):158-164.
15. Ekman R. The suberin monomers and triterpenoids from the outer bark of Betula - verrucosa Ehrh. Holzforschung 1983, 37(4):205-211.
16. Fernandes P., Cabral J.M.S. Phytosterols: applications and recovery methods. Bioresour. Technol. 2007, 98(12):2335-2350.
17. Forrester D.I., Medhurst J.L., Wood M., Beadle C.L., Valencia J.C. Growth and physiological responses to silviculture for producing solid-wood products from Eucalyptus plantations: an Australian perspective. Forest Ecol. Manage. 2010, 259(9):1819-1835.
18. Freire C.S.R., Pinto P.C.R., Santiago A.S., Silvestre A.J.D., Evtuguin D.V., Neto C.P. Comparative study of lipophilic extractives of hardwoods and corresponding ECF bleached kraft pulps. BioResources 2006, 1(1):3-17.
19. Freire C.S.R., Silvestre A.J.D., Neto C.P. Identification of new hydroxy fatty acids and ferulic acid esters in the wood of Eucalyptus globulus. Holzforschung 2002, 56(2):143-149.
20. Freire C.S.R., Silvestre A.J.D., Neto C.P., Cavaleiro J.A.S. Lipophilic extractives of the inner and outer barks of Eucalyptus globulus. Holzforschung 2002, 56(4):372-379.
21. Freire C.S.R., Silvestre A.J.D., Pereira C.C.L., Neto C.P., Cavaleiro J.A.S. New lipophilic components of pitch deposits from an Eucalyptus globulus ECF bleached kraft pulp mill. J. Wood Chem. Technol. 2002, 22(1):55-66.
22. Gupta M.B., Nath R., Gupta G.P., Bhargava K.P. Anti-ulcer activity of some plant triperpenoids. Indian J. Med. Res. 1981, 73(April):649-652.
23. Gutierrez A., del Rio J.C., Gonzalez-Vila F.J., Martin F. Chemical composition of lipophilic extractives from Eucalyptus globulus Labill wood. Holzforschung 1999, 53(5):481-486.
24. Gutierrez R.M.P. Pentacyclic triterpenes from Cirsium pascuarense. J. Chil. Chem. Soc. 2005, 50(3):587-589.
25. Hart N.K., Lamberto J. Morolic acid (3-Hydroxyolean-18-en-28-oic acid) from bark of Eucalyptus papuana F Muell. Aust. J. Chem. 1965, 18(1):115-116.
26. Herrero M., Mendiola J.A., Cifuentes A., Ibáñez E. Supercritical fluid extraction: recent advances and applications. J. Chromatogr. A 2010, 1217(16):2495-2511.
27. Ito J., Chang F.R., Wang H.K., Park Y.K., Ikegaki M., Kilgore N., Lee K.H. Anti-AIDS agents. 48. Anti-HIV activity of moronic acid derivatives and the new melliferone-related triterpenoid isolated from Brazilian propolis. J. Nat. Prod. 2001, 64(10):1278-1281.
28. Kondo M., MacKinnon S.L., Craft C.C., Matchett M.D., Hurta R.A.R., Neto C.C. Ursolic acid and its esters: occurrence in cranberries and other Vaccinium fruit and effects on matrix metalloproteinase activity in DU145 prostate tumor cells. J. Sci. Food Agric. 2011, 91(5):789-796.
29. Limami Y., Pinon A., Leger D.Y., Mousseau Y., Cook-Moreau J., Beneytout J.L., Delage C., Liagre B., Simon A. HT-29 colorectal cancer cells undergoing apoptosis overexpress COX-2 to delay ursolic acid-induced cell death. Biochimie 2011, 93(4):749-757.
30. Liu J. Pharmacology of oleanolic acid and ursolic acid. J. Ethnopharmacol. 1995, 49(2):57-68.
31. Nunez M.J., Reyes C.P., Jimenez I.A., Moujir L., Bazzocchi I.L. Lupane triterpenoids from Maytenus species. J. Nat. Prod. 2005, 68(7):1018-1021.
32. Pelillo M., Iafelice G., Marcon E., Caboni M.F. Identification of plant sterols in hexaploid and tetraploid wheats using gas chromatography with mass spectrometry. Rapid Commun. Mass Spectrom. 2003, 17(20):2245-2252.
33. Pereira C., Meireles M. Supercritical fluid extraction of bioactive compounds: fundamentals, applications and economic perspectives. Food Bioprocess Technol. 2010, 3(3):340-372.
34. Pietarinen S.P., Willfor S.M., Ahotupa M.O., Hemming J.E., Holmbom B.R. Knotwood and bark extracts: strong antioxidants from waste materials. J. Wood Sci. 2006, 52(5):436-444.
35. Qian K.D., Kuo R.Y., Chen C.H., Huang L., Morris-Natschke S.L., Lee K.H. Anti-AIDS agents 81. Design, synthesis, and structure-activity relationship study of betulinic acid and moronic acid derivatives as potent HIV maturation inhibitors. J. Med. Chem. 2010, 53(8):3133-3141.
36. Rencoret J., Gutierrez A., del Rio J.C. Lipid and lignin composition of woods from different eucalypt species. Holzforschung 2007, 61(2):165-174.
37. Reverchon E., De Marco I. Supercritical fluid extraction and fractionation of natural matter. J. Supercrit. Fluids 2006, 38(2):146-166.
38. Rios M.Y., Salinas D., Villarreal M.L. Cytotoxic activity of moronic acid and identification of the new triterpene 3,4-seco-olean-18-ene-3,28-dioic acid from Phoradendron reichenbachianum. Planta Med. 2001, 67(5):443-446.
39. Santos R.C., Salvador J.A.R., Cortes R., Pachon G., Marin S., Cascante M. New betulinic acid derivatives induce potent and selective antiproliferative activity through cell cycle arrest at the S phase and caspase dependent apoptosis in human cancer cells. Biochimie 2011, 93(6):1065-1075.
40. Santos S.A.O., Freire C.S.R., Domingues M.R.M., Silvestre A.J.D., Neto C.P. Characterization of phenolic components in polar extracts of Eucalyptus globulus Labill. Bark by high-performance liquid chromatography-mass spectrometry. J. Agric. Food Chem. 2011, 59(17):9386-9393.
41. Seebacher W., Simic N., Weis R., Saf R., Kunert O. Complete assignments of H-1 and C-13 NMR resonances of oleanolic acid, 18 alpha-oleanolic acid, ursolic acid and their 11-oxo derivatives. Magn. Reson. Chem. 2003, 41(8):636-638.
42. Stryjek R., Vera J.H. PRSV: an improved Peng-Robinson equation of state for pure compounds and mixtures. Can. J. Chem. Eng. 1986, 64(2):323-333.
43. Tarvainen M., Suomela J.-P., Kallio H., Yang B. Triterpene acids in Plantago major: identification, quantification and comparison of different extraction methods. Chromatographia 2010, 71(3):279-284.
44. Trabado G.I., Wilstermann D. Eucalyptus universalis. Global Cultivated Eucalypt Forest Map 2008 2008, Available from: http://www.git-forestry.com/ (accessed April 2012).
45. Yu-hong Z., Tao Y., Yang W. Extraction of betulin from bark of Betula platyphylla by supercritical carbon dioxide extraction. J. Forest Res. 2003, 14(3):202-204.
46. Zhang P., Hao J., Liu J., Zhang L., Sun H. Efficient synthesis of morolic acid and related triterpenes starting from betulin. Tetrahedron 2009, 65(22):4304-4309.