Three hydroxylated lupeol-based triterpenoid esters isolated from the Eastern Nigeria mistletoe parasitic on Kola acuminata

Natural Product Research

Volumn 26, Issue 19, 2012, Pages 1775-1781

  Omeje, Edwin Ogechukwu ^a   Osadebe, Patience Ogoamaka ^a   Esimone, Charles Okechukwu ^b   Nworu, Chukwuemeka Sylvester ^a   Kawamura, Akira ^c   Proksch, Peter ^d  

^a UNIVERSITY OF NIGERIA   (Nigeria)

^b NNAMDI AZIKIWE UNIVERSITY   (Nigeria)

^c CITY UNIVERSITY OF NEW YORK   (United States)

^d HEINRICH HEINE UNIVERSITY   (Germany)

Author keywords

dihydroxylated lupeol; Eastern Nigeria; Kola acuminata; Loranthus micranthus; mistletoe; triterpenoid esters

Indexed keywords

ARACHIDIC ACID; CARBONYL DERIVATIVE; FATTY ACID ESTER; FUNCTIONAL GROUP; HYDROXYL GROUP; LONG CHAIN FATTY ACID; LUPEOL; PALMITIC ACID; STEARIC ACID; TRITERPENOID;

ARTICLE; BIOLOGICAL ACTIVITY; COLA; FRACTIONATION; HETERONUCLEAR SINGLE QUANTUM COHERENCE; HYDROXYLATION; KOLA ACUMINATA; LORANTHUS MICRANTHUS; NONHUMAN; NUCLEAR OVERHAUSER EFFECT; PLANT LEAF; VISCUM ALBUM;

COLA; ESTERS; HEXANES; LORANTHACEAE; MAGNETIC RESONANCE SPECTROSCOPY; MOLECULAR STRUCTURE; NIGERIA; PENTACYCLIC TRITERPENES; PLANTS, MEDICINAL; SPECTROPHOTOMETRY, ULTRAVIOLET;

COLA ACUMINATA; LORANTHUS MICRANTHUS;

EID: 84866557733     PISSN: 14786419     EISSN: 14786427     Source Type: Journal    
DOI: 10.1080/14786419.2011.603316     Document Type: Article

References (58)

1. Ademiluyi, A.O., & Oboh, G. (2008). Antioxidant properties of methanolic extracts of mistletoes (Viscum album) from cocoa and cashew trees in Nigeria. African Journal of Biotechnology, 7, 3138-3142.
2. Badria, F.A., Mikhaeil, B.R., Maatoog, G.T., & Amer, M.M.A. (2003). Immunomodulatory triterpenoids from oleogum resins of Boswellia carterii Birdwood. Z. Naturfursch, 58C, 505-516. (Pubitemid 36971451)
3. Becker, H. (1986). Botany of European mistletoe (Viscum album L.). Oncology, 43, 2-7. (Pubitemid 17211611)
4. Bloksma, N., Scmeirmann, P., & De-Peuver, M. (1982). Stimulation of humoral and cellular immune response by Viscum preparations. Planta Medica, 46, 221-227. (Pubitemid 13194113)
5. Bussing, A. (2000). Biological and pharmacological properties of Viscum album L. In A. Bussing (Ed.), Mistletoe: The genus Viscum (Medicinal and aromatic plants-industrial profiles) (pp. 123-182). Amsterdam, Netherlands: Harwood Academic Publishers.
6. Bussing, A., Regnery, A., & Schweizer, K. (1995). Effects of Viscum album L. on cyclophosphamide-treated peripheral blood mononuclear cells in vitro: Sister chromatid exchanges and activation/proliferation marker expression. Cancer Letters, 94, 199-205.
7. Dzubak, P., Hajduch, M., Vydra, D., Hustova, A., Kvasnica, M., Biedermann, D., . . ., Sarek, J. (2006). Pharmacological activities of natural triterpenoids and their therapeutic implications. Natural Product Reports, 23, 394-411. (Pubitemid 43847140)
8. Ferná ndez, T., Wagner, M.L., Varela, B.G., Ricco, R.A., Hajos, S.E., & Gurni, A.A. (1998). Study of an Argentine mistletoe, the hemiparasite Ligaria cunneifolia (R.et P.) Tiegh. (Loranthaceae). Journal of Ethnopharmacology, 62, 25-34. (Pubitemid 28369720)
9. Fotie, J., Bohle, S., Leimanis, M.L., Jean, F., Bohle, D.S., Leimanis, M.L., . . ., Nkengfack, A.E. (2006). Lupeol long-chain fatty acid esters with antimalarial activity from Holarrhena floribunda. Journal of Natural Product, 69, 62-67. (Pubitemid 43241756)
10. Fukunaga, T., Kajikawa, I., Nishiya, K., Takeya, K., & Itokawa, H. (1989a). Studies on the constituents of the Japanese mistletoe, Viscum album L. var coloratum Ohwi grown on different host trees. Chemical and Pharmaceutical Bulletin, 37, 1300-1303.
11. Fukunaga, T., Kajikawa, I., Nishiya, K., Takeya, K., & Itokawa, H. (1989b). Studies on the constituents of the Japanese mistletoe, Viscum album L, var. coloratum Ohwi grown on different host trees and their antimicrobial and hypotensive properties. Chemical and Pharmaceutical Bulletin, 37, 1543-1546. (Pubitemid 19176829)
12. Fukunaga, T., Nishiya, K., Kajikawa, I., Wantanabe, Y., Suzuki, N., Takeya, K., & Itokawa, H. (1988). Chemical studies on the constituents of Hyphear tanakae HOSOKAWA from different host trees. Chemical and Pharmaceutical Bulletin, 36, 1180-1184.
13. Furukawa, S., Takagi, N., Ikeda, T., Ono, M., Nafady, A.M., Nohara, T., . . ., Yamada, H. (2002). Two novel long-chain alkanoic acid esters of lupeol from Alecrim-propolis. Chemical and Pharmaceutical Bulletin, 50, 439-440. (Pubitemid 41685656)
14. Gallo, M.B.C., & Sarachine, M.J. (2009). Biological activities of lupeol. International Journal of Biomedical and Pharmaceutical Sciences, 3, 44-66.
15. Gill, F.B. (1973). The Machiavellian mistletoes. Frontiers, 38, 2-5.
16. Griggs, P. (1991). Mistletoe, myth, magic and medicine. The Biochemist, 13, 3-4.
17. Hajto, T., Hostanska, K., Fischer, J., & Lentzen, H. (1996). Investigations of cellular parameters to establish the response of a biomodulator: Galactoside-specific lectin from Viscum album plant extract. Phytomedicine, 3, 129-137. (Pubitemid 126491965)
18. Hajto, T., Hostanska, K., & Saller, R. (1996). Mistletoe therapy from the pharmacologic perspective. (Artielein german) Forsh Complementaried, 6, 186-194.
19. Hajto, T., Hostanska, K., & Gabius, H.J. (1989). Modulatory potency of the -galactoside specific lectin from mistletoe extracts (Iscador) on the host defense system in vivo in rabbits and patients. Cancer Research, 49, 4803-4808. (Pubitemid 19213628)
20. Khwaja, T.A., Dias, C.B., & Pentecost, S. (1986). Recent studies on the anticancer activities of mistletoe (Viscum album) and its alkaloids. Oncology, 43, 42-50. (Pubitemid 17211616)
21. Obatomi, A.K., Bikomo, P.O., & Temple, V.J. (1994). Anti-diabetic properties of the African mistletoe in streptozotocin-induced diabetic rats. Journal of Ethnopharmacology, 43, 13-17. (Pubitemid 24186505)
22. Obatomi, A.K., Oye, A.A.A., & Temple, V.J. (1997). Reduction in serum glucose and cholesterol levels in experimental diabetic rats treated with extracts of African mistletoe (Loranthus bengwensis). Medical Science Research, 25, 651-654. (Pubitemid 27480520)
23. Ofem, O.E., Eno, A.E., Imoru, J., Nkanu, E., Unoh, F., & Ibu, J.O. (2007). Effects of crude aqueous leaf extract of Viscum album (mistletoe) in hypertensive rats. Indian Journal of Pharmacology, 39, 15-19. (Pubitemid 46381927)
24. Omeje, E.O., Osadebe, P.O., & Umeyor, C.E. (2008). Extracts of Eastern Nigeria mistletoe up-regulates cellular and humoral immune response in mice. Recent Progress in Medicinal Plants; Ethnomedicine; Source and Mechanism I, 27, 473-485.
25. Osadebe, P.O., & Omeje, E.O. (2009a). Comparative acute toxicities and immunomodulatory potentials of five Eastern Nigeria mistletoes. Journal of Ethnopharmacology, 126, 287-293.
26. Osadebe, P.O., & Omeje, E.O. (2009b). Main immunomodulatory constituents of Eastern Nigeria mistletoe, Loranthus micranthus Linn. Asian Pacific Journal of Tropical Medicine, 2, 11-18.
27. Osadebe, P.O., Okide, G.B., & Akabogu, I.C. (2004). Study on anti-diabetic activities of crude methanolic extracts of Loranthus micranthus (Linn) sourced from five different host trees. Journal of Ethnopharmacology, 95, 133-138. (Pubitemid 39422659)
28. Osadebe, P.O., & Uzochukwu, I.C. (2006). Chromatographic and antimotility studies on the extracts of Loranthus micranthus. Journal of Pharmaceutical and Allied Sciences, 3, 263-268.
29. Ribereau-Gayon, G., Jung, M.L., Baudino, S., Sallé, G., & Beck, J.P. (1986). Effects of mistletoe (Viscum album L.) extracts on cultured tumor cells. Experientia, 42, 594-599.
30. Ademiluyi, AO, and, Oboh, G. 2008. Antioxidant properties of methanolic extracts of mistletoes (Viscum album) from cocoa and cashew trees in Nigeria. African Journal of Biotechnology, 7: 3138-3142.
31. Badria, FA, Mikhaeil, BR, Maatoog, GT, and, Amer, MMA. 2003. Immunomodulatory triterpenoids from oleogum resins of Boswellia carterii Birdwood. Z. Naturfursch, 58C: 505-516. (Pubitemid 36971451)
32. Becker, H. 1986. Botany of European mistletoe (Viscum album L.). Oncology, 43: 2-7. (Pubitemid 17211611)
33. Bloksma, N, Scmeirmann, P, and, De-Peuver, M. 1982. Stimulation of humoral and cellular immune response by Viscum preparations. Planta Medica, 46: 221-227. (Pubitemid 13194113)
34. Bssing, A. 2000. Biological and pharmacological properties of Viscum album L. In Mistletoe: The genus Viscum (Medicinal and aromatic plants-industrial profiles), Edited by: Bssing, A. 123-182. Amsterdam, Netherlands: Harwood Academic Publishers.
35. Bssing, A, Regnery, A, and, Schweizer, K. 1995. Effects of Viscum album L. on cyclophosphamide-treated peripheral blood mononuclear cells invitro: sister chromatid exchanges and activation/proliferation marker expression. Cancer Letters, 94: 199-205.
36. Dzubak, P, Hajduch, M, Vydra, D, Hustova, A, Kvasnica, M, Biedermann, D, Sarek, J. 2006. Pharmacological activities of natural triterpenoids and their therapeutic implications. Natural Product Reports, 23: 394-411. (Pubitemid 43847140)
37. Fernández, T, Wagner, ML, Varela, BG, Ricco, RA, Hajos, SE, and, Gurni, AA. 1998. Study of an Argentine mistletoe, the hemiparasite Ligaria cunneifolia (R.et P.) Tiegh. (Loranthaceae). Journal of Ethnopharmacology, 62: 25-34. (Pubitemid 28369720)
38. Fotie, J, Bohle, S, Leimanis, ML, Jean, F, Bohle, DS, Leimanis, ML, Nkengfack, AE. 2006. Lupeol long-chain fatty acid esters with antimalarial activity from Holarrhena floribunda. Journal of Natural Product, 69: 62-67. (Pubitemid 43241756)
39. Fukunaga, T, Kajikawa, I, Nishiya, K, Takeya, K, and, Itokawa, H. 1989a. Studies on the constituents of the Japanese mistletoe, Viscum album L. var coloratum Ohwi grown on different host trees. Chemical and Pharmaceutical Bulletin, 37: 1300-1303.
40. Fukunaga, T, Kajikawa, I, Nishiya, K, Takeya, K, and, Itokawa, H. 1989b. Studies on the constituents of the Japanese mistletoe, Viscum album L, var. coloratum Ohwi grown on different host trees and their antimicrobial and hypotensive properties. Chemical and Pharmaceutical Bulletin, 37: 1543-1546. (Pubitemid 19176829)
41. Fukunaga, T, Nishiya, K, Kajikawa, I, Wantanabe, Y, Suzuki, N, Takeya, K, and, Itokawa, H. 1988. Chemical studies on the constituents of Hyphear tanakae HOSOKAWA from different host trees. Chemical and Pharmaceutical Bulletin, 36: 1180-1184.
42. Furukawa, S, Takagi, N, Ikeda, T, Ono, M, Nafady, AM, Nohara, T, Yamada, H. 2002. Two novel long-chain alkanoic acid esters of lupeol from Alecrim-propolis. Chemical and Pharmaceutical Bulletin, 50: 439-440. (Pubitemid 41685656)
43. Gallo, MBC, and, Sarachine, MJ. 2009. Biological activities of lupeol. International Journal of Biomedical and Pharmaceutical Sciences, 3: 44-66.
44. Gill, FB. 1973. The Machiavellian mistletoes. Frontiers, 38: 2-5.
45. Griggs, P. 1991. Mistletoe, myth, magic and medicine. The Biochemist, 13: 3-4.
46. Hajto, T, Hostanska, K, Fischer, J, and, Lentzen, H. 1996. Investigations of cellular parameters to establish the response of a biomodulator: galactoside-specific lectin from Viscum album plant extract. Phytomedicine, 3: 129-137. (Pubitemid 126491965)
47. Hajto, T, Hostanska, K, and, Saller, R. 1996. Mistletoe therapy from the pharmacologic perspective. (Artielein german) Forsh Complementaried, 6: 186-194.
48. Hajto, T, Hostanska, K, and, Gabius, HJ. 1989. Modulatory potency of the -galactoside specific lectin from mistletoe extracts (Iscador) on the host defense system invivo in rabbits and patients. Cancer Research, 49: 4803-4808. (Pubitemid 19213628)
49. Khwaja, TA, Dias, CB, and, Pentecost, S. 1986. Recent studies on the anticancer activities of mistletoe (Viscum album) and its alkaloids. Oncology, 43: 42-50. (Pubitemid 17211616)
50. Obatomi, AK, Bikomo, PO, and, Temple, VJ. 1994. Anti-diabetic properties of the African mistletoe in streptozotocin-induced diabetic rats. Journal of Ethnopharmacology, 43: 13-17. (Pubitemid 24186505)
51. Obatomi, AK, Oye, AAA, and, Temple, VJ. 1997. Reduction in serum glucose and cholesterol levels in experimental diabetic rats treated with extracts of African mistletoe (Loranthus bengwensis). Medical Science Research, 25: 651-654. (Pubitemid 27480520)
52. Ofem, OE, Eno, AE, Imoru, J, Nkanu, E, Unoh, F, and, Ibu, JO. 2007. Effects of crude aqueous leaf extract of Viscum album (mistletoe) in hypertensive rats. Indian Journal of Pharmacology, 39: 15-19. (Pubitemid 46381927)
53. Omeje, EO, Osadebe, PO, and, Umeyor, CE. 2008. Extracts of Eastern Nigeria mistletoe up-regulates cellular and humoral immune response in mice. Recent Progress in Medicinal Plants; Ethnomedicine; Source and Mechanism I, 27: 473-485.
54. Osadebe, PO, and, Omeje, EO. 2009a. Comparative acute toxicities and immunomodulatory potentials of five Eastern Nigeria mistletoes. Journal of Ethnopharmacology, 126: 287-293.
55. Osadebe, PO, and, Omeje, EO. 2009b. Main immunomodulatory constituents of Eastern Nigeria mistletoe, Loranthus micranthus Linn. Asian Pacific Journal of Tropical Medicine, 2: 11-18.
56. Osadebe, PO, Okide, GB, and, Akabogu, IC. 2004. Study on anti-diabetic activities of crude methanolic extracts of Loranthus micranthus (Linn) sourced from five different host trees. Journal of Ethnopharmacology, 95: 133-138. (Pubitemid 39422659)
57. Osadebe, PO, and, Uzochukwu, IC. 2006. Chromatographic and antimotility studies on the extracts of Loranthus micranthus. Journal of Pharmaceutical and Allied Sciences, 3: 263-268.
58. Ribereau-Gayon, G, Jung, ML, Baudino, S, Sallé, G, and, Beck, JP. 1986. Effects of mistletoe (Viscum album L.) extracts on cultured tumor cells. Experientia, 42: 594-599.