Oleanolic acid synthetic oligoglycosides: A review on recent progress in biological activities

Pharmazie

Volumn 69, Issue 7, 2014, Pages 483-495

  Xu, Kuo ^a   Chu, Fuhao ^a   Li, Guoliang ^a   Xu, Xin ^a   Wang, Penglong ^a   Song, Jixiang ^a   Zhou, Sen ^a   Lei, Haimin ^a  

^a BEIJING UNIVERSITY OF CHINESE MEDICINE   (China)

Author keywords

[No Author keywords available]

Indexed keywords

ALPHA GLUCOSIDASE; ALPHA GLUCOSIDASE INHIBITOR; CARBON; OLEANOLIC ACID; OLEANOLIC ACID DERIVATIVE; BIOLOGICAL PRODUCT; GLYCOSIDE; HERBACEOUS AGENT;

ANTIBACTERIAL ACTIVITY; ANTIDIABETIC ACTIVITY; ANTIFUNGAL ACTIVITY; ANTINEOPLASTIC ACTIVITY; BIOLOGICAL ACTIVITY; DRUG SYNTHESIS; GLYCOSYLATION; HEMOLYSIS; HUMAN; NONHUMAN; OSTEOPOROSIS; REVIEW; STRUCTURE ACTIVITY RELATION; ANIMAL; CARBOHYDRATE ANALYSIS; CHEMISTRY; MOLECULAR GENETICS; SYNTHESIS;

ANIMALS; BIOLOGICAL PRODUCTS; CARBOHYDRATE SEQUENCE; DRUGS, CHINESE HERBAL; GLYCOSIDES; HUMANS; MOLECULAR SEQUENCE DATA; OLEANOLIC ACID; STRUCTURE-ACTIVITY RELATIONSHIP;

EID: 84904564557     PISSN: 00317144     EISSN: None     Source Type: Journal    
DOI: 10.1691/ph.2014.3933     Document Type: Review

References (71)

1. Ali MS, Jahangir M, Hussan SS, Choudhary MI (2002) Inhibition of α-glucosidase by oleanolic acid and its synthetic derivatives. Phytochemistry 60: 295-299. (Pubitemid 34947536)
2. Anderson E, Jiang X, Liu X, Visnick M (2011) Antioxidant inflammation modulators: Oleanolic acid derivatives with saturation in the C-ring. US Patent 7915402 Mar 29, 2011.
3. Anderson E, Jiang X, Visnick M (2012) Antioxidant inflammation modulators: Oleanolic acid derivatives with amino and other modifications at C-17. US Patent 8124799 Feb 28, 2012.
4. Anderson E, Jiang X, Liu X, Visnick M (2012) Antioxidant inflammation modulators: Oleanolic acid derivatives with saturation in the C-ring. US Patent 8124656 Feb 28, 2012.
5. Anderson E, Jiang X, Visnick M (2012) Antioxidant inflammation modulators: Oleanolic acid derivatives with amid acid and other modulators at C-17. US Patent 20120214814 Aug 23, 2012.
6. Chen L, Zhang Y, Kong X, Lan E, Huang Z, Peng S, Kaufman DL, Tian J (2008) Design, synthesis, and antihepatocellular carcinoma activity of nitric oxide releasing derivatives of oleanolic acid. J Med Chem 51: 4834-4838.
7. Cheng K, Liu J, Liu X, Li H, Sun H, Xie J (2009) Synthesis of glucoconjugates of oleanolic acid as inhibitors of glycogen phosphorylase. Carbohyd Res 344: 841-850.
8. Cheriti A, Babadjamian A, Balansard G (1994) Preparation of lactone derivatives on glycosidation of oleanolic acid under triflic catalysis. J Nat Prod 57: 1160-1163. (Pubitemid 24279034)
9. Dharmappa KK, Kumar RV, Nataraju A, Mohamed R, Shivaprasad HV, Vishwanath BS (2009) Anti-inflammatory activity of oleanolic acid by inhibition of secretory phospholipase A2 . Planta Med 75: 211-215.
10. Fai YM, Tao CC (2009) A review of presence of oleanolic acid in natural products. Sample Review for Natura Proda Medica 2: 77-290.
11. Guo T, Liu Q, Wang P, Zhang L, Zhang W, Li Y (2009) Facile synthesis of three bidesmosidic oleanolic acid saponins with strong inhibitory activity on pancreatic lipase. Carbohyd Res 344: 1167-1174.
12. Han BH, Kim-Cho MS, Han YN, Park MH (1984) Studies on triterpenoid corticomimetics (2) synthesis of 11-oxo-oleanolic acid derivatives and their anti-inflammatory activities. Korean Biochem J 17: 91-97.
13. Honda T, Honda Y, Jr FGF, Gribble GW, Suh N, Place AE, Rendi MH, Sporn MB (2002) A novel dicyanotriterpenoid, 2-cyano-3, 12-dioxooleana-1, 9(11)-dien-28-onitrile, active at picomolar concentrations for inhibition of nitric oxide production. Bioorg Med Chem Lett 12: 1027-1030. (Pubitemid 34242794)
14. Horiuchi K, Shiota S, Hatano T, Yoshida T, Kuroda T, Tsuchiya T (2007) Antimicrobial activity of oleanolic acid from Salvia officinalis and related compounds on vancomycin-resistant enterococci (VRE). Biol Pharm Bull 30: 1147-1149. (Pubitemid 46883872)
15. Huang Z, Fu J, Ding Y, Lai Y, Peng S, Zhang Y (2011) Synthesis and antihuman hepatocellular carcinoma activity of new nitric oxide-releasing glycosyl derivatives of oleanolic acid. Sciencepaper Online. Available at: http://www.paper.edu.cn/releasepaper/content/201101-1023. Accessed on 1 Jan 2011.
16. Huang Z, Fu J, Liu L, Sun Y, Lai Y, Ji H, Knaus EE, Tian J, Zhang Y (2012) Glycosylated diazeniumdiolate-based oleanolic acid derivatives: Synthesis, in vitro and in vivo biological evaluation as anti-human hepatocellular carcinoma agents. Org Biomol Chem 10: 3882-3891.
17. Huang Z, Zhang Y, Zhao L, Jing Y, Lai Y, Zhang L, Guo Q, Yuan S, Zhang J, Chen L, Peng S, Tian J (2010) Synthesis and anti-human hepatocellular carcinoma activity of new nitric oxide-releasing glycosyl derivatives of oleanolic acid. Org Biomol Chem 8: 632-639.
18. Huang X, Cheng S, DuY, Bing F (2009) Synthesis of oleanolic acid saponins mimicking components of Chinese folk medicine Di Wu. Carbohyd Res 344: 1153-1158.
19. Jiang X, Liu X, Greiner J, Szucs SS, Visnick M (2011) Antioxidant inflammation modulators: C-17 homologated oleanolic acid derivatives. US Patent 7943778 May 17, 2011.
20. Khathi A, Masola B, Musabayane CT (2013) Effects of Syzygium aromaticum-derived oleanolic acid on glucose transport and glycogen synthesis in the rat small intestine. J Diabetes 5: 80-87.
21. Kuttan G, Pratheeshkumar P, Manu KA,KuttanR(2011) Inhibition of tumor progression by naturally occurring terpenoids. Pharm Biol 49: 995-1007.
22. Lee W, Yang EJ, Ku SK, Song KS, Bae JS (2013) Anti-inflammatory effects of oleanolic acid on LPS-induced inflammation in vitro and in vivo. Inflammation 36: 94-102.
23. Li CX, Zang J, Wang P, Zhang XL, Guan HS, Li YX (2006) Synthesis of two natural oleanolic acid saponins. Chinese J Chem 24: 509-517.
24. Li J, Guo WJ, Yang QY (2002) Effects of ursolic acid and oleanolic acid on human colon carcinoma cell line HCT15. World J Gastroenterol 8: 493-495. (Pubitemid 34692749)
25. Li JF, Chen SJ, Zhao Y, Li JX (2009) Glycoside modification of oleanolic acid derivatives as a novel class of anti-osteoclast formation agents. Carbohyd Res 344: 599-605.
26. Li JX, Hareyama T, Tezuka Y, Zhang Y, Miyahara T, Kadota S (2005) Five newoleanolic acid glycosides from Achyranthes bidentata with inhibitory activity on osteoclast formation. Planta Med 71: 673-679. (Pubitemid 41133079)
27. Liu J (1995) Pharmacology of oleanolic acid and ursolic acid. J Ethnopharmacol 49: 57-68.
28. Liu J (2005) Oleanolic acid and ursolic acid: Research perspectives. J Ethnopharmacol 100: 92-94.
29. Liu Q, Wang P, Zhang L, Guo T, Lv G, Li Y (2009) Concise synthesis of two natural triterpenoid saponins, oleanolic acid derivatives isolated from the roots of Pulsatilla chinensis. Carbohyd Res 344: 1276-1281.
30. Liu QC (2010) Synthesis and biological evaluation of several natural saponins and analogues. M. D. Thesis, Ocean University of China.
31. Melo CL, Queiroz MGR, Fonseca SGC, Bizerra AMC, Lemos TLG, Melo TS, Santos FA, Rao VS (2010) Oleanolic acid, a natural triterpenoid improves blood glucose tolerance in normal mice and ameliorates visceral obesity in mice fed a high-fat diet. Chem-Biol Interact 185: 59-65.
32. Meng YQ, Nie HH, Wang XC, Li D, Ge CX, Zhao N, Chen H, Cao B (2011) Synthesis of glucoconjugates of oleanolic acid as inhibitors of glycogen phosphorylase. Acta Pharm Sinica 46: 1215-1220.
33. Ngubane PS, Masola B, Musabayane CT (2011) The effects of Syzygium aromaticum-derived oleanolic acid on glycogenic enzymes in streptozotocin- induced diabetic rats. Renal Failure 33: 434-439.
34. Parkin DM, Bray F, Ferlay J, Pisani P (2005) Global cancer statistics, 2002. Ca-Cancer J Clin 55: 74-108. (Pubitemid 40372904)
35. Patil CR, Jadhav RB, Singh PK, Mundada S, Patil PR (2010) Protective effect of oleanolic acid on gentamicin induced nephrotoxicity in rats. Phytother Res 24: 33-37.
36. Pei SC, Wu JB, Lei F, Qian S, Hai L, Wu Y (2012) Synthesis of oleanolic disaccharide derivatives. Chinese Chem Lett 23: 403-406.
37. Pollier J, Goossens A (2012) Oleanolic acid. Phytochemistry 77: 10-15.
38. Pratheeshkumar P (2011) Oleanolic acid induces apoptosis by modulating p53, Bax, Bcl-2 and caspase-3 gene expression and regulates the activation of transcription factors and cytokine profile in B16F. JEPTO 30: 21-31.
39. Qian S, Wu Y, He YX, Wang ZY, Yang WY, Chen X (2012) Synthesis and biological evaluation of oleanane triterpenoid with γ-lactone functionality in ring C. Chem J Chinese U 33: 969-975.
40. Qian S, Li JH, Zhang YW, Chen X, Wu Y (2010) Synthesis and α- glucosidase inhibitory activity of oleanolic acid derivatives. J Asian Nat Prod Res 12: 20-29.
41. Qu F, Li YX, Zhang YC, Zang J (2003) Synthesis of oleanolic acid glycoconjugate. Chines J Org Chem 23: 249-257.
42. Rong ZT, Gong XJ, Sun HB, Li YM, Ji H (2011) Protective effects of oleanolic acid on cerebral ischemic damage in vivo and H2O 2-induced injury in vitro. Pharm Biol 49: 78-85.
43. Saito S, Ebashi J, Sumita S, Furumoto T, Nagamura Y, Nishida K, Isiguro I (1993) Comparison of cytoprotective effects of saponins isolated from leaves of Aralia elata Seem. (Araliaceae) with synthesized bisdesmosides of oleanoic acid. Chem Pharm Bull 41: 1395-401. (Pubitemid 23285539)
44. Seebacher W, Weis R, Jurenitsch J, Rauchensteiner K, Haslinger E (1999) Synthesis and haemolytic activity of oleanolic acid trisaccharides. Monatsh Chem 130: 1383-1391.
45. Seebacher W, Haslinger E, Rauchensteiner K, Jurenitsch J, Presser A, Weis R (1999) Synthesis and haemolytic activity of Randianin isomers. Monatsh Chem 130: 887-897.
46. Sha Y, Yan MC, Liu J, Liu Y, Cheng MS (2008) Facile synthesis of oleanolic acid monoglycosides and diglycosides. Molecules 13: 1472-1486.
47. Shode FO,Koorbanally N, Mpiana PT, Tshibangu DST, Oyedeji OO, Habila JD (2012) In vitro anti-sickling activity of betulinic acid, oleanolic acid and their derivatives. US Patent 20120237629 Sep. 20, 2012.
48. Shyu MH, Kao TC, Yen GC (2010) Oleanolic acid and ursolic acid induce apoptosis in HuH7 human hepatocellular carcinoma cells through a mitochondrial-dependent Pathway and downregulation of XIAP. J Agric Food Chem 58: 6110-6118.
49. Somsak L, Czifrak K, Toth M, Bokor E, Chrysina ED, Alexacou KM, Hayes JM, Tiraidis C, Lazoura E, Leonidas DD, Zographos SE, Oikonomakos NG (2008) New inhibitors of glycogen phosphorylase as potential antidiabetic agents. Curr Med Chem 15: 2933-2983.
50. Sultana N, Ata A (2008) Oleanolic acid and related derivatives as medicinally important compounds. J Enzym Inhib Med C 23: 739-756.
51. Sun J, Han X, Yu B (2003) Synthesis of a typical N-acetylglucosamine- containing saponin, oleanolic acid 3-yl α-L-arabinopyranosyl-(1→2)- α-L-arabinopyranosyl-(1→6)-2- acetamido-2-deoxy-β-D- glucopyranoside. Carbohyd Res 338: 827-833. (Pubitemid 36398001)
52. Szakiel A, Grzelak A, Dudek P, Janiszowska W (2003) Biosynthesis of oleanolic acid and its glycosides in Calendula officinalis suspension culture. Plant Physiol Biochem 41: 271-275. (Pubitemid 36524566)
53. Szakiel A, Ruszkowski D, Janiszowska W (2005) Saponins in Calendula officinalis L.-structure, biosynthesis, transport and biological activity. Phytochem Rev 4: 151-158. (Pubitemid 41752173)
54. Szakiel A, Ruszkowski D, Grudniak A, Kurek A, Wolska KI, Doligalska M, Janiszowska W (2008) Antibacterial and antiparasitic activity of oleanolic acid and its glycosides isolated from Marigold (Calendula officinalis). Planta Med 74: 1709-1715.
55. Tsai S, Yin M (2012) Anti-oxidative, anti-glycative and anti-apoptotic effects of oleanolic acid in brain of mice treated by D-galactose. Eur J Pharmacol 689: 81-88.
56. Tsai S, Yin M (2008) Antioxidative and anti-Inflammatory protection of oleanolic acid and ursolic acid in PC12 cells. J Food Sci 73: 174-178.
57. Wang J (2004) Preparation of glucosamine oligosaccharides and their triterpene saponins. S. M. Thesis, Ocean University of China.
58. Wang X, Bai H, Zhang X, Liu J, Cao P, Liao N, Zhang W, Wang Z, Hai C (2013) Inhibitory effect of oleanolic acid on hepatocellular carcinoma via ERK-p53-mediated cell cycle arrest and mitochondrial-dependent apoptosis. Carcinogenesis 34: 1323-1330.
59. Wang X, Li YL, Wu H, Liu JZ, Hu JX, Liao N, Peng J, Cao PP, Liang X, Hai CX (2011) Antidiabetic effect of oleanolic acid: A promising use of a traditional pharmacological agent. Phytother Res 25: 1031-1040.
60. Wang X, Liu R, Zhang W, Zhang X, Liao N, Wang Z, Li W, Qin X, Hai C (2013) Oleanolic acid improves hepatic insulin resistance via antioxidant, hypolipidemic and anti-inflammatory effects. Mol Cell Endocrinol 376: 70-80.
61. Wang X, Ye X, Liu R, Chen H, Bai H, Liang X, Zhang X, Wang Z, Li W, Hai C (2010) Antioxidant activities of oleanolic acid in vitro: Possible role of Nrf2 and MAP kinases. Chem-Biol Interact 184: 328-337.
62. Wang Z, Hsu C, Huang C, Yin M (2010) Anti-glycative effects of oleanolic acid and ursolic acid in kidney of diabetic mice. Eur J Pharmacol 628: 255-260.
63. Wei J, Liu H, Liu M, Wu N, Zhao J, Xiao L, Han L, Chu E, Lin X (2012) Oleanolic acid potentiates the antitumor activity of 5-fluorouracil in pancreatic cancer cells. Oncol Rep 28: 1339-1345.
64. Wen X, Sun H, Liu J, Cheng K, Zhang P, Zhang L, Hao J, Zhang L, Ni P, Zographos SE, Leonidas DD, Alexacou KM, Gimisis T, Hayes JM, Oikonomakos NG (2008) Naturally occurring pentacyclic triterpenes as inhibitors of glycogen phosphorylase: synthesis, structure-activity relationships, and X-ray crystallographic studies. J Med Chem 51: 3540-3554. (Pubitemid 351875009)
65. Yadava RN, Jharbade J (2007) A new bioactive triterpenoid saponin from the seeds of Lactuca scariola Linn. Nat Prod Res 21: 500-506. (Pubitemid 47393739)
66. Yan MC (2008) Design, synthesis and bioactivity investigation of oleanolic acid derivatives. M. D. Thesis, Shenyang Pharmaceutical University.
67. Yan S, Huang C, Wu S, Yin M (2010) Oleanolic acid and ursolic acid induce apoptosis in four human liver cancer cell lines. Toxicol in Vitro 24: 842-848.
68. Yu B, Sun J (2009) Current synthesis of triterpene saponins. Chem Asian J 4: 642-654.
69. Zhang Y, Li J, Zhao J,Wang S, Pan Y, Tanaka K, Kadota S (2005) Synthesis and activity of oleanolic acid derivatives, a novel class of inhibitors of osteoclast formation. Bioorg Med Chem Lett 15: 1629-1632. (Pubitemid 40312543)
70. Zhao H, Zong G, Zhang J, Wang D, Liang X (2011) Synthesis and anti-fungal activity of seven oleanolic acid glycosides. Molecules 16: 1113-1128.
71. Zhou R, Zhang Z, Zhao L, Jia C, Xu S, Mai Q, Lu M, Huang M, Wang L, Wang X, Jin D, Bai X (2011) Inhibition of mTOR signaling by oleanolic acid contributes to its anti-tumor activity in osteosarcoma cells. J Orthop Res 29: 846-852.