Terpenoids from Stinking toe (Hymneae courbaril) fruits with cyclooxygenase and lipid peroxidation inhibitory activities

Food Chemistry

Volumn 105, Issue 2, 2007, Pages 485-490

  Jayaprakasam, Bolleddula ^a   Alexander Lindo, Ruby L ^b   DeWitt, David L ^c   Nair, Muraleedharan G ^a  

^a Bioactive Natural Products and Phytoceuticals   (United States)

^b UNIVERSITY OF THE WEST INDIES   (Jamaica)

^c Michigan State University   (United States)

Author keywords

Cyclooxygenase inhibition; Diterpenoids; Hymenaea courbaril; Lipid peroxidation inhibition; Sucrose

Indexed keywords

13 LABDA 7,13 DIEN 15 OIC ACID; ACETYLSALICYLIC ACID; CARBON 13; CROTOMACHLIN; CYCLOOXYGENASE 1; CYCLOOXYGENASE 2; DITERPENOID; IBUPROFEN; LABD 13 EN 8 OL 15 OIC ACID; LABD 13 EN 8 OL 15 OIC ACID METHYL ESTER; LABDANOLIC ACID; LINOLENIC ACID; PROSTAGLANDIN SYNTHASE; PROSTAGLANDIN SYNTHASE INHIBITOR; PROTON; ROFECOXIB; SESQUITERPENE; SPATHULENOL; SUCROSE; TERPENOID DERIVATIVE; UNCLASSIFIED DRUG;

ANTIINFLAMMATORY ACTIVITY; ARTICLE; CARBON NUCLEAR MAGNETIC RESONANCE; CELL STRAIN HCT116; CELL STRAIN MCF 7; CONTROLLED STUDY; DRUG ISOLATION; DRUG PURIFICATION; ENZYME INHIBITION; FRUIT; HUMAN; HUMAN CELL; HYMNEAE COURBARIL; LIPID PEROXIDATION; MEDICINAL PLANT; NONHUMAN; PROTON NUCLEAR MAGNETIC RESONANCE;

HYMENAEA COURBARIL;

EID: 34447266444     PISSN: 03088146     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.foodchem.2007.04.004     Document Type: Article

References (30)

1. Abdel-Kader M., Berger J.M., Slebodnick C., Hoch J., Malone S., Wisse J.H., et al. Isolation and absolute configuration of ent-halimane diterpenoids from Hymenaea courbaril from the suriname rain forest. Journal of Natural Products 65 (2002) 11-15
2. Akihisa T., Yasukawa K., and Tokuda H. Potentially cancer chemopreventive and anti-inflammatory terpenoids from natural sources. In: Atta-ur-Rahman (Ed). Studies in natural products chemistry (Part J) Vol. 29 (2003), Elsevier, Amsterdam 73-126
3. Ames B.N., Shigenaga M.K., and Hagen T.M. Oxidants, antioxidants and degenerative disorders diseases of aging. Proceedings of National Academy of Sciences 90 (1993) 7915-7922
4. Arckcoll D.B. Some leguminous trees providing useful fruits in the north of Brazil. Pesquisa Agropecuaria Brasilia 19 (1984) 231-234
5. Arora A., Nair M.G., and Strasburg G.M. Antioxidant activities of isoflavones and their biological metabolites in a liposomal system. Archives of Biochemistry and Biophysics 356 (1998) 133-141
6. Braga F.C., Wagner H., Lombardi J.A., and DeOliveira A.B. Screening of Brazilian plant species for in vitro inhibition of 5-lipooxygenase. Phytomedicine 6 (2000) 447-452
7. Carman R.M., and Duffield A.R. The optical rotation of some C15-oxygenated labda-8 (17), 13-dienes. Australian Journal of Chemistry 48 (1995) 1357-1366
8. Castro J.M., Salido S., Altarejos J., Nogueras M., and Sanchez A. Synthesis of ambrox from labdanolic acid. Tetrahedron 58 (2002) 5941-5949
9. Chang Y.K., Silva M.R., Gutkoski L.C., Sebio L., and Da Silva M.A.A.P. Development of extruded snacks using jatobá (Hymenaea stigonocarpa Mart) flour and cassava starch blends. Journal of the Science of Food and Agriculture 78 (1998) 59-66
10. Duke, J.A. & Wain, K.K. Medicinal Plants of the World. http://www.hort.purdue.edu/newcrop/duke_energy/Hymenaea_courbaril. html#Folk%20Medicine.
11. Henry G.E., Momin R.A., Nair M.G., and Dewitt D.L. Antioxidant and cyclooxygenase activities of fatty acids found in food. Journal of Agricultural and Food Chemistry 50 (2002) 2231-2234
12. Herlem D., Huu K.-F., and Kende A.S. Studies toward the total synthesis of diterpenes in the labdane series III. Synthesis of two epimeric 6,7,8-trihydroxylabdadienes. Tetrahedron 50 (1994) 2055-2070
13. 13C NMR spectral analysis of eperuane diterpenes. Phytochemistry 16 (1977) 1842-1844
14. Jayaprakasam B., Strasburg G.A., and Nair M.G. Potent lipid peroxidation inhibitors from Withania somnfera fruits. Tetrahedron 60 (2004) 3109-3121
15. Jayaprakasam B., Zhang Y., and Nair M.G. Tumor cell proliferation and cyclooxygenase enzyme inhibitory compounds in Amaranthus tricolor. Journal of Agricultural and Food Chemistry 52 (2004) 6939-6943
16. Karl-Heinz W., and Ibrahim E. Biological relevance of terpenoids: overview focusing on mono, di and tetraterpenes. Annals of Nutrition & Metabolism 47 (2003) 95-106
17. Khoo S.F., and Oehlschlager A.C. Structure and stereochemistry of the diterpenes of Hymenaea courbaril (Caesalpinioideae) seed pod resin. Tetrahedron 29 (1973) 3379-3388
18. 13C reassignment by two-dimensional NMR spectroscopy. Nuclear Magnetic Resonance in Chemistry 28 (1990) 124-128
19. Lee Y.T., and Langenheim J.H. Systematics of the genus Hymenaea L. (Leguminosae, Caesalpinioideae, Detarieae) Vol. 69 (1975), Chemistry of California Press Ltd. pp. 1-109
20. Little, E. L. & Wadsworth, F. H. (1964). Common trees of Puerto Rico and the Virgin Islands. Ag. Handbook 249, USDA, Washington, DC.
21. Marsaioli A.J., Leitao Filho H., and De Paiva Campello J. Diterpenes in the bark of Hymenaea coubaril. Phytochemistry 14 (1975) 1882-1883
22. Mitchell J.A., and Warner T.D. Cyclooxygease-2: pharmacology, physiology, biochemistry and relevance to NSAID therapy. British Journal of Pharmacology 128 (1999) 1121-1132
23. Mukherjee D., Nissen S.E., and Topol E.J. Risk of cardiovascular events associated with selective COX-2 inhibitors. Journal of American Medical Association 286 (2001) 954-959
24. Nogueira R.T., Shephered G.J., Laverde Jr. A., Marsaioli A.J., and Imamura P.M. Clerodane-type diterpenes from the seed pods of Hymenaea courbaril var. stilbocarpa. Phytochemistry 58 (2001) 1153-1157
25. Sivarajah K., Lasker J.M., and Eling T.E. Prostaglandin synthetase-dependent cooxidation of (±)-benzo(a)pyrene-7,8-dihydrodiol by human lung and other mammalian tissues. Cancer Research 41 (1981) 1834-1839
26. Smith W.L., DeWitt D.L., and Garavito R.M. Cyclooxygenases: structural, cellular, and molecular biology. Annual Reviews of Biochemistry 69 (2000) 145-182
27. Surh Y.-J., Chun K.-S., Cha H.-H., Han S.S., Keum Y.-S., Park K.-K., et al. Molecular mechanisms underlying chemopreventive activities of anti-inflammatory phytochemicals: down-regulation of COX-2 and iNOS through suppression of NF-κB activation. Mutation Research 480-481 (2001) 243-268 and references cited therein
28. Teramoto T., Yuno T., Morita H., Katsumura S., Sakaguchi K., and Isoe S. Synthesis of (±)-crotomachlin. Synlett (1996) 141-142
29. Witsberger, D., Current, D., & Archer, E. (1982). Arboles del Parque Deininger. Ministerio de Educación, El Salvador, pp. 146-147.
30. Zhang Y., DeWitt D.L., Murugesan S., and Nair M.G. Cyclooxygenase-2 enzyme inhibitory triterpenoids from Picrorhiza kurroa seeds. Life Sciences 27 (2005) 3222-3230