Biological activities of lupeol

Systematic Reviews in Pharmacy

Volumn 2, Issue 2, 2011, Pages 96-103

  Wal, P ^a   Wal, A ^b   Sharma, G ^a   Rai, A K ^a  

^a PRANVEER SINGH INSTITUTE OF TECHNOLOGY   (India)

^b Jodhpur National University   (India)

Author keywords

Cancer; Chemoprevention; Inflammation; Lupeol

Indexed keywords

CALCIMYCIN; CARBOXYLYASE; DEXAMETHASONE; DOXORUBICIN; FAS ANTIGEN; FLICE INHIBITORY PROTEIN; IMMUNOGLOBULIN ENHANCER BINDING PROTEIN; LIPOXYGENASE; LIVER PROTECTIVE AGENT; LUPENONE; LUPEOL; LUPEOL 28 AL 20(29)EM 3 ONE; PHOSPHATIDYLINOSITOL 3 KINASE; RAS PROTEIN; TRITERPENOID; UNCLASSIFIED DRUG; VINCRISTINE;

ABDOMINAL CONSTRICTION; ABDOMINAL DISEASE; ANTIARTHRITIC ACTIVITY; ANTIINFLAMMATORY ACTIVITY; ANTINEOPLASTIC ACTIVITY; ARTHRITIS; ASTHMA; CANCER CELL CULTURE; CANCER INHIBITION; CELL CYCLE PROGRESSION; DRUG ACTIVITY; DRUG CYTOTOXICITY; DRUG STRUCTURE; EDEMA; ENZYME INHIBITION; HIGH PERFORMANCE LIQUID CHROMATOGRAPHY; IMMUNE RESPONSE; IMMUNOSUPPRESSIVE TREATMENT; IN VITRO STUDY; IN VIVO STUDY; INFLAMMATION; LIVER PROTECTION; LIVER TOXICITY; MALIGNANT NEOPLASTIC DISEASE; MASS SPECTROMETRY; NONHUMAN; PANCREAS CANCER; PRIORITY JOURNAL; PROSTATE CANCER; REVIEW; STRUCTURE ACTIVITY RELATION; ULTRAVIOLET RADIATION; WOUND HEALING;

EID: 80155145264     PISSN: 09758453     EISSN: 09762779     Source Type: Journal    
DOI: 10.4103/0975-8453.86298     Document Type: Review

References (99)

1. Ovesna Z, Vachalkova A, Horvathova K, Tothova D. Pentacyclic triterpenoic acids: New chemoprotective compounds. Minireview. Neoplasma 2004;51:327-33. (Pubitemid 39486104)
2. Liby KT, Yore MM, Sporn MB. Triterpenoids and rexinoids as multifunctional agents for the prevention and treatment of cancer. Nat Rev Cancer 2007;7:357-69. (Pubitemid 46652485)
3. Moreau RA, Whitaker BD, Hicks KB. Phytosterols, phytostanols, and their conjugates in foods: Structural diversity, quantitative analysis, and health-promoting uses. Prog Lipid Res 2002;41:457-500.
4. Roy SK, Ali M, Sharma MP, Ramachandram R. New pentacyclic triterpenes from the roots of Hemidesmus indicus. Pharmazie 2001;56:244-6. (Pubitemid 32209954)
5. Jiri P. Biologically active pentacyclic triterpenes and their current medicine. J Appl Biomed 2003;1:7-12.
6. Gawronska-Grzywacz M, Krzaczek T. Identification and determination of triterpenoids in Hieracium pilosella L. J Sep Sci 2007;30:746-50. (Pubitemid 46542085)
7. Imam S, Azhar I, Hasan MM, Ali MS, Ahmed SW. Two triterpenes lupanone and lupeol isolated and identified from Tamarindus indica linn. Pak J Pharm Sci 2007;20:125-7.
8. Sudhahar V, Kumar SA, Varalakshmi P. Role of lupeol and lupeol linoleate on lipemic-oxidative stress in experimental hypercholesterolemia. Life Sci 2006;78:1329-35. (Pubitemid 43199954)
9. Karikas GA, Euerby MR, Waigh RD. Constituents of the stems of Arbutus unedo. Planta Med 1987;53:223-4. (Pubitemid 17057087)
10. Dos Santos-Pereira A, de Aquino-Neto FR. Chemical composition of Tipuana tipu, a source for tropical honey bee products. Z Naturforsch 2003;58:201-6.
11. Zhang H, Shibuya M, Yokota S, Ebizuka Y. Oxidosqualene cyclases from cell suspension cultures of Betula platyphylla var. japonica: Molecular evolution of oxidosqualene cyclases in higher plants. Biol Pharm Bull 2003;26:642-50. (Pubitemid 39663556)
12. Nikiema JB, Vanhaelen-Fastre R, Vanhaelen M, Fontaine J, De Graef C, Heenen M. Effects of anti-inflammatory triterpenes isolated from Leptadenia hastata latex on keratinocyte proliferation. Phytother Res 2001;15:131-4.
13. Yamashita K, Lu H, Lu J, Chen G, Yokoyama T, Sagara Y, et al. Effect of three triterpenoids, lupeol, betulin, and betulinic acid on the stimulus induced superoxide generation and tyrosyl phosphorylation of proteins in human neutrophils. Clin Chim Acta 2002;325:91-6. (Pubitemid 35279630)
14. Aratanechemuge Y, Hibasami H, Sanpin K, Katsuzaki H, Imai K, Komiya T. Induction of apoptosis by lupeol isolated from mokumen (Gossampinus malabarica L. Merr) in human promyelotic leukemia HL-60 cells. Oncol Rep 2004;11:289-92.
15. Mutai C, Abatis D, Vagias C, Moreau D, Roussakis C, Roussis V. Cytotoxic lupane-type triterpenoids from Acacia mellifera. Photochemistry 2004;65:1159-64. (Pubitemid 38542754)
16. Geetha T, Varalaxmi P, Mary R. Effect of triterpenes from Crataeva nurvala stem bark on lipid peroxidation in adjuvant induced arthritis in rats. Pharmacol Res 1998;37:3.
17. Fernadez A, Alvarez A, Garco MD, Sonz MT. Anti-inflammatory effect of Pimenta racemosa var. ozua and isolation of the triterpene lupeol. Farmaco 2001;56:335-8. (Pubitemid 32463319)
18. Du SJ, Gariboldi P, Jommi G. Constituents of Shashen (Adenophora axilliflora). Planta Med 1986;52:317-20. (Pubitemid 16030210)
19. Martelanc M, Vovk I, Simonovska B. Determination of three major triterpenoids in epicuticular wax of cabbage (Brassica oleracea L.) by high-performance liquid chromatography with UV and mass spectrometric detection. J Chromatogr A 2007;1164:145-52. (Pubitemid 47284101)
20. Geetha T, Varalakshmi P. Anticomplement activity of triterpenes from Crataeva nurvala stem bark in adjuvant arthritis in rats. Gen Pharmacol 1999;32:495-7. (Pubitemid 29192843)
21. Bani S, Kaul A, Khan B, Ahmad SF, Suri KA, Gupta BD, et al. Suppression of T lymphocyte activity by lupeol isolated from Crataeva religiosa. Phytother Res 2006;20:279-87.
22. Latha RM, Lenin M, Rasool M, Varalakshmi P. A novel derivative pentacyclic triterpene and omega 3 fatty acid. Prostaglandins Leukot Essent Fatty Acids 2001;64:81-5.
23. Vasconcelos JF, Teixeira MM, Barbosa-Filho JM, Lúcio AS, Almeida JR, de Queiroz LP, et al. The triterpenoid lupeol attenuates allergic airway inflammation in a murine model. Int Immunopharmacol 2008;8:1216-21.
24. Lin WW, Karin M. A cytokine-mediated link between innate immunity, inflammation, and cancer. J Clin Invest 2007;117:1175-83. (Pubitemid 46718402)
25. Geetha T, Varalakshmi P. Anti-inflammatory activity of lupeol and lupeol linoleate in rats. J Ethnopharmacol 2001;76:77-80. (Pubitemid 32510734)
26. Singh S, Bani S, Singh GB, Gupta BD, Banerji SK, Singh B. Antiinflammatory activity of lupeol. Fitoterapia 1997;68:9-16.
27. Sunitha S, Nagaraj M, Varalakshmi P. Hepatoprotective effect of lupeol and lupeol linoleate on tissue antioxidant defence system in cadmiuminduced hepatotoxicity in rats. Fitoterapia 2001;72:516-23. (Pubitemid 32594803)
28. Fukuda Y, Sakai K, Matsunaga S, Tokuda H, Tanaka R. Cancer Lett 2006;240:94-101.
29. Yamashita K, Lu H, Lu J, Chen G, Yokoyama T, Sagara Y, et al. Effect of three triterpenoids, lupeol, betulin, and betulinic acid on the stimulusinduced superoxide generation and tyrosyl phosphorylation of proteins in human neutrophils. Clin Chim Acta 2002;325:91-6. (Pubitemid 35279630)
30. Harish BG, Krishna V, Santosh Kumar HS, Khadeer Ahamed BM, Sharath R, Kumara Swamy HM. Wound healing activity and docking of glycogensynthase-kinase- 3-beta-protein with isolated striterpenoid lupeol in rats. Phytomedicine 2008;15:763-7.
31. Setzer WN, Setzer MC. Plant-derived triterpenoids as potential antineoplastic agents. Mini Rev Med Chem 2003;3:540-56.
32. Bradford PG, Awad AB. Phytosterols as anticancer compounds. Mol Nutr Food Res 2007;51:161-70. (Pubitemid 47083247)
33. Waterman E, Lockwood B. Active components and clinical applications of olive oil. Altern Med Rev 2007;12:331-42.
34. Min BS, Gao JJ, Nakamura N, Hattori M. Triterpenes from the spores of Ganoderma lucidum and their cytotoxicity against meth-A and LLC tumor cells. Chem Pharm Bull (Tokyo) 2001;48:1026-33.
35. Nagumo A, Takanashi K, Hojo H, Suzuki Y. Cytotoxicity of Betulinic acidcteriohopane-32-ol against mouse leukemia L1210 and P388 cells in vitro. Toxicol Lett 2001;58:309-13.
36. Najid A, Simon A, Cook J, Chable-Rabinovitch H, Delage C, Chulia AJ, et al. Characterization of ursolic acid as a lipoxygenase and cyclooxygenase inhibitor using macrophages, platelets and differentiated HL60 leukemic cells. FEBS Lett 1992;299:213-7.
37. Novotny L, Vachalkova A, Biggs D. Ursolic acid: An antitumorigenic and chemopreventive activity. Neoplasma 2001;48:241-6. (Pubitemid 32802432)
38. Olukoga A, Donaldson D. Liquorice and its health implications. J R Soc Health 2000;120:83-9. (Pubitemid 30458457)
39. Patocka J. Anti-inflammatory triterpenoids from mysterious mushroom Ganoderma lucidum and their potential possibility in modern medicine. Acta Med 1999;42:123-5.
40. Lanzotti V. The analysis of onion and garlic. J Chromatogr A 2006;1112:3-22.
41. Bauvois B, Dauzonne D. Aminopeptidase-N/CD13 (EC 3.4.11.2) inhibitors: Chemistry, biological evaluations, and therapeutic prospects. Med Res Rev 2006;26:88-130. (Pubitemid 43986471)
42. Molno J, Gyoot N, Tanaka M, Hohmann J, Bergmann-Leitner E, Molnar P, et al. Inhibition of multidrug resistance of cancer cells by natural diterpenes triterpenes and carotenoids. Curr Pharm Des 2006;12: 287-311.
43. Cuendet M, Pezzuto JM. Antitumor activity of bruceantin: An old drug with new promise. J Nat Prod 2004;67:269-72. (Pubitemid 38282918)
44. Sporn MB, Suh N. Chemoprevention of cancer. Carcinogenesis 2000;21:525-30. (Pubitemid 30137938)
45. Devereux TR, Risinger JI, Barrett JC. Mutations and altered expression of the human cancer genes: What they tell us about causes. IARC Sci Publ 1999:19-42.
46. Coleman WB, Tsongalis GJ. The role of genomic instability in human carcinogenesis. Anticancer Res 1999;19:4645-64. (Pubitemid 30093479)
47. Depinho RA. The age of cancer. Nature 2000;408:248-54.
48. Ponder BA. Cancer genetics. Nature 2001;411:336-41. (Pubitemid 32467042)
49. Lira Wde M, dos Santos FV, Sannomiya M, Rodrigues CM, Vilegas W, Varanda EA. Modulatory effect of Byrsonima basiloba extracts on the mutagenicity of certain direct and indirect-acting mutagens in Salmonella typhimurium assays. J Med Food 2008;11:111-9. (Pubitemid 351450500)
50. Nigam N, Prasad S, Shukla Y. Preventive effects of lupeol on DMBA induced DNA alkylation damage in mouse skin. Food Chem Toxicol 2007;45:2331-5. (Pubitemid 47451582)
51. Sultana S, Saleem M, Sharma S, Khan N. Lupeol, a triterpene, prevents free radical mediated macromolecular damage and alleviates benzoyl peroxide induced biochemical alterations in murine skin. Indian J Exp Biol 2003;41:827-31. (Pubitemid 36953552)
52. Prasad S, Kumar Yadav V, Srivastava S, Shukla Y. Protective effects of lupeol against benzo[a] pyrene induced clastogenicity in mouse bone marrow cells. Mol Nutr Food Res 2008;52:1117-20.
53. Saleem M, Afaq F, Adhami VM, Mukhtar H. Lupeol modulates NFkappa B and PI3K/Akt pathways and inhibits skin cancer in CD-1 mice. Oncogene 2004;23:5203-14. (Pubitemid 38980353)
54. Basuroy UK, Gerner EW. Emerging concepts in targeting the polyamine metabolic pathway in epithelial cancer chemoprevention and chemotherapy. J Biochem 2006;139:27-33. (Pubitemid 43258843)
55. Saleem M, Maddodi N, Abu Zaid M, Khan N, bin Hafeez B, Asim M, et al. Lupeol inhibits growth of highly aggressive human metastatic melanoma cells in vitro and in vivo by inducing apoptosis. Clin Cancer Res 2008;14:2119-27. (Pubitemid 351551124)
56. Aratanechemuge Y, Hibasami H, Sanpin K, Katsuzaki H, Imai K, Komiya T. Induction of apoptosis by Lupeol isolated from mokumen (Gossampinus malabarica L. Merr) in human promyelotic leukemia HL-60 cells. Oncol Rep 2004;11:289-92.
57. Cmoch P, Pakulski Z, Swaczynová J, Strnad M. Synthesis of lupine typesaponins bearing mannosyl and 3, 6-branched trimannosyl residues and their evaluation as anticancer agents. Carbohydr Res 2008;343:995-1003.
58. Lambertini E, Lampronti I, Penolazzi L, Khan MT, Ather A, Giorgi G, et al. Expression of estrogen receptor alpha gene in breast cancer cells treated with transcription factor decoy is modulated by Bangladeshi natural plant extracts. Oncol Res 2005;15:69-79. (Pubitemid 40825918)
59. Aratanechemuge Y, Hibasami H, Sanpin K, Katsuzaki H, Imai K, Komiya T. Induction of apoptosis by lupeol isolated from mokumen (Gossampinus malabarica L. Merr) in human promyelotic leukemia HL-60 cells. Oncol Rep 2004;11:289-92.
60. Hata K, Hori K, Takahashi S. Differentiation-and apoptosis-inducing activities by pentacyclic triterpenes on a mouse melanoma cell line. J Nat Prod 2002;65:645-8. (Pubitemid 34547402)
61. Mutai C, Abatis D, Vagias C, Moreau D, Roussakis C, Roussis V. Cytotoxic lupane-type triterpenoids from Acacia mellifera. Phytochemistry 2004;65:1159-64. (Pubitemid 38542754)
62. Gauthier C, Legault J, Lebrun M, Dufour P, Pichette A. Glycosidation of lupane-type triterpenoids as potent in vitro cytotoxic agents. Bioorg Med Chem 2006;14:6713-25. (Pubitemid 44233310)
63. Liu W, Ho JC, Cheung FW, Liu BP, Ye W, Che C. Apoptotic activity of betulinic acid derivatives on murine melanoma B16 cell line. Eur J Pharmacol 2004;498:71-8. (Pubitemid 39208062)
64. Hata K, Hori K, Ogasawara H, Takahashi S. Antileukemia activities of Lup-28-al-20(29)-en-3-one, a lupine triterpene. Toxicol Lett 2003;143: 1-7. (Pubitemid 36412166)
65. Lee TK, Poon RT, Wo JY, Ma S, Guan XY, Myers JN, et al. Lupeol suppresses cisplatin-induced nuclear factor-kappaB activation in head and neck squamous cell carcinoma and inhibits local invasion and nodal metastasis in an orthotopic nude mouse model. Cancer Res 2007;67:8800-9. (Pubitemid 47437456)
66. Fortune JM, Osheroff N. Topoisomerase II as a target for anticancer drugs: When enzymes stop being nice. Prog Nucleic Acid Res Mol Biol 2000;64:221-53.
67. Kaufmann SH. Cell death induced by topoisomerasetargeted drugs: More questions than answers. Biochim Biophys Acta 1998;1400: 195-211. (Pubitemid 28475104)
68. Austin CA, Marsh KL. Eukaryotic DNA topoisomerase II beta. Bioessays 1998;20:215-26.
69. Drake FH, Hofmann GA, Mong SM, Bartus JO, Hertzberg RP, Johnson RK, et al. In vitro and intracellular inhibition of topoisomerase II by the antitumor agent merbarone. Cancer Res 1989;49:2578-83. (Pubitemid 19143380)
70. Wada S, Iida A, Tanaka R. Screening of triterpenoids isolated from Phyllanthus flexuosus for DNA topoisomerase inhibitory activity. J Nat Prod 2001;64:1545-7. (Pubitemid 34051976)
71. Jemal A, Siegel R, Ward E, Murray T, Xu J, Thun MJ. Cancer statistics 2007. CA Cancer J Clin 2007;57:43-66.
72. Yip-Schneider MT, Lin A, Marshall MS. Pancreatic tumor cells with mutant K-ras suppress ERK activity by MEK-dependent induction of MAP kinase phosphatase-2. Biochem Biophys Res Commun 2001;280:992-7. (Pubitemid 32924437)
73. Xiong HQ. Molecular targeting therapy for pancreatic cancer. Cancer Chemother Pharmacol 2004;54:S69-77. (Pubitemid 39517752)
74. Asano T, Yao Y, Zhu J, Li D, Abbruzzese JL, Reddy SA. The PI 3-kinase/Akt signaling pathway is activated due to aberrant Pten expression and targets transcription factors NF-kappaB and c-Myc in pancreatic cancer cells. Oncogene 2004;23:8571-80. (Pubitemid 39576463)
75. Stoll V, Calleja V, Vassaux G, Downward J, Lemoine NR. Dominant negative inhibitors of signalling through the phosphoinositol 3-kinase pathway for gene therapy of pancreatic cancer. Gut 2005;54:109-16. (Pubitemid 40007228)
76. Saleem M, Kaur S, Kweon M, Adhami VM, Afaq F, Mukhtar H. Lupeol, a fruit and vegetable based triterpene induces apoptotic death of human pancreatic adenocarcinoma cells via inhibition of Ras signaling pathway. Carcinogenesis 2005;26:1956-64. (Pubitemid 41631270)
77. Preetha SP, Kanniappan M, Selvakumar E, Nagaraj M, Varalakshmi P. Lupeol ameliorates aflatoxin B1-induced peroxidative hepatic damage in rats. Comp Biochem Physiol 2006;143:333-9. (Pubitemid 43850413)
78. Prasad S, Kalra N, Shukla Y. Hepatoprotective effects of lupeol and mango pulp extract of carcinogen induced alteration in Swiss albino mice. Mol Nutr Food Res 2007;51:352-9. (Pubitemid 47083670)
79. Sporn MB, Suh N. Chemoprevention of cancer. Carcinogenesis 2000;21:525-30. (Pubitemid 30137938)
80. Klein EA, Thompson IM. Update on chemoprevention of prostate cancer. Curr Opin Urol 2004;14:143-9. (Pubitemid 38582312)
81. Brawley OW, Parnes H. Prostate cancer prevention trials in the USA. Eur J Cancer 2000;36:1312-5.
82. Peter ME, Krammer PH. The CD95 (APO-1/Fas) DISC and beyond. Cell Death Differ 2003;10:26-35.
83. Ashkenazi A, Dixit VM. Death receptors: Signaling and modulation. Science 1998;281:1305-8. (Pubitemid 28406815)
84. Wu XX, Mizutani Y, Kakehi Y, Yoshida O, Ogawa O. Enhancement of Fas-mediated apoptosis in renal cell carcinoma cells by adriamycin. Cancer Res 2000;60:2912-8.
85. Suzuki A, Matsuzawa A, Iguchi T. Down regulation of Bcl-2 is the first step on Fas-mediated apoptosis of male reproductive tract. Oncogene 1996;13:31-7. (Pubitemid 26248542)
86. Hedlund TE, Duke RC, Schleicher MS, Miller GJ. Fasmediated apoptosis in seven human prostate cancer cell lines: Correlation with tumor stage. Prostate 1998;36:92-101. (Pubitemid 28311313)
87. Takayama H, Takakuwa T, Dong Z. Fas gene mutations in prostatic intraepithelial neoplasia and concurrent carcinoma: Analysis of laser captures micro dissected specimens. Lab Invest 2001;81:283-8. (Pubitemid 32245060)
88. Saleem M, Kweon M, Yun J, Adhami VM, Khan N, Syed DN, et al. A novel dietary triterpene lupeol induces Fas-mediated apoptotic death of androgen-sensitive prostate cancer cells and inhibits tumor growth in a xenograft model. Cancer Res 2005;65:11203-13. (Pubitemid 41713392)
89. Andrikopoulos NK, Kaliora AC, Assimopoulou AN, Papapeorgiou VP. Biological activity of some naturally occurring resins, gums, and pigments against in vitro LDL oxidation. Phytother Res 2003;17:501-7. (Pubitemid 36605902)
90. Saleem R, Ahmad SI, Ahmed M, Faizi Z, Zikr-ur-Rehman S, Ali M, et al. Hypotensive activity and toxicology of constituents from Bombax ceiba stem bark. Biol Pharm Bull 2003;26:41-6. (Pubitemid 39663640)
91. Moriarity DM, Huang J, Yancey CA, Zhang P, Setzer WN, Lawton RO, et al. Lupeol is the cytotoxic principle in the leaf extract of Dendropanax cf. querceti. Planta Med 1998;64:370-2. (Pubitemid 28234279)
92. Sturm S, Gil RR, Chai H, Ngassapa OD, Santisuk T, Reutrakul V, et al. Lupane derivatives from Lophopetalum wallichii with farnesyl protein transferase inhibitory activity. J Nat Prod 1996;59:658-63. (Pubitemid 26264629)
93. Kässmeyer S, Plendl J, Custodis P, Bahramsoltani M. New insights in vascular development vasculogenesis and endothelial progenitor cells. Anat Histol Embryol 2009;38:1-11.
94. Martin K. Targeting apoptosis with dietary bioactive agents. Exp Biol Med 2006;231:117-29. (Pubitemid 43213448)
95. Rodriguez M, Schaper J. Apoptosis: Measurement and technical issues. J Mol Cell Cardiol 2005;38:15-20. (Pubitemid 40038649)
96. Cowley S, Paterson H, Kemp P, Marshall CJ. Activation of MAP kinase kinase is necessary and sufficient for PC12 differentiation and for transformation of NIH 3T3 cells. Cell 1994;77:841-52. (Pubitemid 24187682)
97. Bode AM, Dong Z. Signal transduction pathways: Targets for chemoprevention of skin cancer. Lancet Oncol 2000;1:181-8.
98. Sobol RW, Prasad R, Evenski A, Baker A, Yang XP, Horton J, et al. The lyase activity of DNA repair protein-polymerase protects from DNA damage induced cytotoxicity. Nature 2000;405:807-10. (Pubitemid 30407855)
99. Aggarwal BB, Shishodia S. Molecular targets of dietary agents for prevention and therapy of cancer. Biochem Pharmacol 2006;71: 1397-421.