Potential of natural products of herbal origin as monoamine oxidase inhibitors

Current Pharmaceutical Design

Volumn 22, Issue 3, 2016, Pages 268-276

  Orhan, Ilkay Erdogan ^a  

^a GAZI UNIVERSITY   (Turkey)

Author keywords

Alkaloid; Coumarin; Enzyme inhibition; Flavonoid; MAO; Monoamine oxidase; Natural compounds

Indexed keywords

ALKALOID DERIVATIVE; COUMARIN DERIVATIVE; FLAVONOID; IRIDOID; MONOAMINE OXIDASE INHIBITOR; NATURAL PRODUCT; PHENOL DERIVATIVE; QUINONE DERIVATIVE; STILBENOID DERIVATIVE; TERPENE DERIVATIVE; UNCLASSIFIED DRUG; XANTHONE DERIVATIVE; PLANT MEDICINAL PRODUCT;

ARTICLE; DRUG ACTIVITY; DRUG STRUCTURE; ENZYME INHIBITION; IC50; PRIORITY JOURNAL; CHEMICAL STRUCTURE; CHEMISTRY; DRUG DEVELOPMENT; ISOLATION AND PURIFICATION; MEDICINAL PLANT;

DRUG DISCOVERY; MOLECULAR STRUCTURE; MONOAMINE OXIDASE INHIBITORS; PLANT PREPARATIONS; PLANTS, MEDICINAL;

EID: 84962554120     PISSN: 13816128     EISSN: 18734286     Source Type: Journal    
DOI: 10.2174/1381612822666151112150612     Document Type: Article

References (71)

1. Fowler J, Logan J, Volkow ND, Wang GJ, MacGregor RR, Ding YS. Monoamine oxidase: radiotracer development and human studies. Methods 2002; 27: 263-7.
2. Westlund KN, Denney RM, Kochersperger LM, Abell CW, Denney RM. Distinct monoamine oxidase A and B populations in primate brain. Science 1985; 230: 181-3.
3. Bolasco A, Carradori S, Fioravanti R. Focusing on new monoamine oxidase inhibitors. Expert Opin Ther Patents 2010; 20: 909-39.
4. Shih JC, Chen K, Ridd MJ. Monoamine oxidase: from genes to behavior. Annu Rev Neurosci 1999; 22: 197-217.
5. Tipton KF, O’Carrol AM, McCrodden JM. The catalytic behavior of monoamine oxidase. J Neurotransm 1987; 23: 25-35.
6. Richard BS. Radical ideas about monoamine oxidase. Acc Chem Res 1995; 28: 335-42.
7. Wouters J. Structural aspects of monoamine oxidase and its reversible inhibition. Curr Med Chem 1998; 5: 137-62.
8. Crane GE. Psychiatric side effects of iproniazide. Am J Psychiatry 1956; 112: 494-7.
9. Yamada M, Yasuhara H. Clinical pharmacology of MAO inhibitors: safety and future. Neurotoxicology 2004; 25: 243-50.
10. Herraiz T, Chaparro C. Human monoamine oxidase enzymatic activity is inhibited by tobacco smoke: β-carboline alkaloids act as potent and reversible inhibitors. Biochem Biophys Res Commun 2005; 326: 378-86.
11. Youdim MBH, Edmondson D, Tipton KF. The therapeutic potential of monoamine oxidase inhibitors. Nat Rev Neurosci 2006; 7: 295-309.
12. Singh A, Naidu PS, Kulkarni SK. Quercetin potentiates L-Dopa reversal of drug-induced catalepsy in rats: possible COMT/MAO inhibition. Pharmacology 2003; 68: 81-8.
13. O’Brien EM, Kiely KA, Tipton KF. A discontinuous luminometric assay for monoamine oxidase. Biochem Pharmacol 1993; 46: 1301-6.
14. Malorni W, Giammarioli AM, Matarrese P, et al. Protection against apoptosis by monoamine oxidase inhibitors. FEBS Lett 1998; 462: 155-9.
15. Strolin-Benedetti M, Dostert PL. Monoamine oxidase: from physiology and pathophysiology to the design and clinical application of reversible inhibitors. Adv Drug Res 1992; 23: 65-125.
16. Pacher P, Kecskemeti V. Trends in the development of new antidepressants. Is there a light at the end of the tunnel? Curr Med Chem 2004; 11: 925-43.
17. Hulsken S, Märtin A, Mohajeri MH, Homberg JR. Food-derived serotonergic modulators: Effects on mood and cognition. Nutr Res Rev 2013; 26: 223-34.
18. Bet PM, Hugtenburg JG, Penninx BWJH, Hoogendijk WJG. Side effects of antidepressants during long-term use in a naturalistic setting. Eur Neuropsychopharmacol 2013; 23: 1443-51.
19. Delogu G, Viña D, Serra S, Lamela M. Herbal natural products as a source of monoamine oxidase inhibitors: A review. Curr Topics Med Chem 2012; 12: 2131-44.
20. Jäger AK, Saaby L. Flavonoids and the CNS. Molecules 2011; 16: 1471-85.
21. Grosso C, Valentão P, Ferreres F, Andrade PB. The use of flavonoids in central nervous system disorders. Curr Med Chem 2013; 20: 4694-719.
22. Thiede HM, Walper A. Inhibition of MAO and COMT by Hypericum extracts and hypericin. J Geriatr Psych Neurol 1994; 7: S54-6.
23. Kubin A, Wierrani F, Burner U, Alth G, Grünberger W. Hypericin - The facts about a controversial agent. Curr Pharm Des 2005; 11: 233-53.
24. Pan X, Kong LD, Zhang Y, Cheng CHK, Tan RX. In vitro inhibition of rat monoamine oxidase by liquiritigenin and isoliquiritigenin isolated from Sinofranchetia chinensis. Acta Pharmacol Sin 2000; 21: 949-53.
25. Sloley BD, Urichuk LJ, Morley P, et al. Identification of kaempferol as a monoamine oxidase inhibitor and potential neuroprotectant in extracts of Ginkgo biloba leaves. J Pharm Pharmacol 2000; 52: 451-9.
26. Lee MH, Lin RD, Shen LY, Yang LL, Yen KY, Hou WC. Monoamine oxidase B and free radical scavenging activities of natural flavonoids in Melastoma candidum D. Don. J Agric Food Chem 2001; 49: 5551-5.
27. Hong SS, Hwang JS, Lee SA, Han XH, Ro JS, Lee KS. Inhibitors of monoamine oxidase activity from the fruits of Crataegus pinnatifida Bunge. Korean J Pharmacogn 2002; 33: 285-90.
28. Chimenti F, Cottiglia F, Bonsignore L, et al. Quercetin as the active principle of Hypericum hircinum exerts a selective inhibitory activity against MAO-A: Extraction, biological analysis, and computational study. J Nat Prod 2006; 69: 945-9.
29. Saaby L, Rasmussen HB, Jäger AK. MAO-A inhibitory activity of quercetin from Calluna vulgaris (L.) Hull. J Ethnopharmacol 2009; 121: 178-81.
30. Yoshino S, Hara A, Sakakibara H, et al. Effect of quercetin and glucuronide metabolites on the monoamine oxidase-A reaction in mouse brain mitochondria. Nutrition 2011; 27: 847-52.
31. Demirkiran O. Three new benzophenone glycosides with MAO-A inhibitory activity from Hypericum thasium Griseb. Phytochem Lett 2012; 5: 700-4.
32. Xiang HH, Seong SH, Ji SH, Myung KL, Bang YH, Ro JS. Monoamine oxidase inhibitory components from Cayratia japonica. Arch Pharm Res 2007; 30: 13-7.
33. Haraguchi H, Tanaka Y, Kabbash A, Fujioka T, Ishizu T, Yagi A. Monoamine oxidase inhibitors from Gentiana lutea. Phytochemistry 2004; 65: 2255-60.
34. Hwang JS, Lee SA, Seong SH, et al. Monoamine oxidase inhibitory components from the roots of Sophora flavescens. Arch Pharm Res 2005; 28: 190-4.
35. Hou WC, Lin RD, Chen CT, Lee MH. Monoamine oxidase B (MAO-B) inhibition by active principles from Uncaria rhynchophylla. J Ethnopharmacol 2005; 100: 216-20.
36. Mazzio EA, Harris N, Soliman KF. Food constituents attenuate monoamine oxidase activity and peroxide levels in C6 astrocyte cells. Planta Med 1998; 64: 603-6.
37. Xiang HH, Seong SH, Ji SH, et al. Monoamine oxidase inhibitory constituents from the fruits of Cudrania tricuspidata. Arch Pharm Res 2005; 28: 1324-7.
38. Han XH, Hwang JH, Hong SS, et al. Monoamine oxidase inhibitory flavonoids from the root bark of Cudrania tricuspidata. Nat Prod Sci 2010; 16: 75-9.
39. Olsen HT, Stafford GI, van Staden J, Christensen SB, Jäger K. Isolation of the MAO-inhibitor naringenin from Mentha aquatica L. J Ethnopharmacol 2008; 117: 500-2.
40. Tomić M, Tovilović G, Butorović B, et al. Neuropharmacological evaluation of diethylether extract and xanthones of Gentiana kochiana. Pharmacol Biochem Behav 2005; 81: 535-42.
41. Urbain A, Marston A, Sintra Grilo L, et al. Xanthones from Gentianella amarella ssp. acuta with acetylcholinesterase and monoamine oxidase inhibitory activities. J Nat Prod 2008; 71: 895-7.
42. Moon UR, Sircar D, Barthwal R, et al. Shoot cultures of Hoppea fastigiata (Griseb.) C.B. Clarke as potential source of neuroprotective xanthones. J Nat Med 2015; 69: 375-86.
43. Kim JH, Son YK, Kim GH, Hwang KH. Xanthoangelol and 4- hydroxyderricin are the major active principles of the inhibitory activities against monoamine oxidases on Angelica keiskei K. Biomol Ther 2013; 21: 234-40.
44. Zhou CX, Kong LD, Ye C, Cheng CHK, Tan RX. Inhibition of xanthine and monoamine oxidases by stilbenoids from Veratrum taliense. Planta Med 2001; 67: 158-61.
45. Kong LD, Cheng CHK, Tan RX. Inhibition of MAO A and B by some plant-derived alkaloids, phenols and anthraquinones. J Ethnopharmacol 2004; 91: 351-5.
46. Bhutani MK, Bishnoi M, Kulkarni SK. Anti-depressant like effect of curcumin and its combination with piperine in unpredictable chronic stress-induced behavioral, biochemical and neurochemical changes. Pharmacol Biochem Behav 2009; 92: 39-43.
47. Kim JH, Kim GH, Hwang KH. Monoamine oxidase and dopamine β-hydroxylase inhibitors from the fruits of Gardenia jasminoides. Biomol Ther 2012; 20: 214-9.
48. Kaya D, Jäger AK, Yalçin FN, Ersöz T. MAO-A inhibition profiles of some benzophenone glucosides from Gentiana verna subsp. pontica. Nat Prod Commun 2014; 9: 505-6.
49. Patil PO, Bari SB, Firke SD, Deshmukh PK, Donda ST, Patil DA. A comprehensive review on synthesis and designing aspects of coumarin derivatives as monoamine oxidase inhibitors for depression and Alzheimer's disease. Bioorg Med Chem 2013; 21: 2434-50.
50. Orhan IE, Gulcan HO. Coumarins: auspicious cholinesterase and monoamine oxidase inhibitors. Curr Topics Med Chem 2015; 15: 1673-82.
51. Kong LD, Tan RX, Woo AYH, Cheng CHK. Inhibition of rat brain monoamine oxidase activities by psoralen and isopsoralen: Implications for the treatment of affective disorders. Pharmacol Toxicol 2001; 88: 75-80.
52. Huong DTL, Dat NT, Minh CV, Kang JS, Kim YH. Monoamine oxidase inhibitors from Aquilaria agallocha. Nat Prod Sci 2002; 8: 30-3.
53. Young SJ, Huong DTL, Ki Hwan B, Myung KL, Young HK. Monoamine oxidase inhibitory coumarin from Zanthoxylum schinifolium. Planta Med 2002; 68: 84-5.
54. Giovine A, Renis M, Bertolino A. In vivo and in vitro studies on the effect of tetrahydropapaveroline and salsolinol on COMT and MAO activity in rat brain. Pharmacology 1976; 14: 86-94.
55. Lee MK, Lee SS, Ro JS, Lee KS, Kim HS. Inhibitory effects of bioactive fractions containing protoberberine alkaloids from the roots of Coptis japonica on monoamine oxidase activity. Nat Prod Sci 1999; 5: 159-61.
56. Lee SS, Kai M, Lee MK. Inhibitory effects of sanguinarine on monoamine oxidase activity in mouse brain. Phytother Res 2001; 15: 167-9.
57. Schwarz MJ, Houghton PJ, Rose S, Jenner P, Lees AD. Activities of extract and constituents of Banisteriopsis caapi relevant to Parkinsonism. Pharmacol Biochem Behav 2003; 75: 627-33.
58. Herraiz T, Chaparro C. Analysis of monoamine oxidase enzymatic activity by reversed-phase high performance liquid chromatography and inhibition by β-carboline alkaloids occurring in foods and plants. J Chrom A 2006; 1120: 237-43.
59. Herraiz T, González D, Ancín-Azpilicueta C, Arán VJ, Guillén H. β-Carboline alkaloids in Peganum harmala and inhibition of human monoamine oxidase (MAO). Food Chem Toxicol 2010; 48: 839-45.
60. Lee SA, Hong SS, Han XH, et al. Piperine from the fruits of Piper longum with inhibitory effect on monoamine oxidase and antidepressant- like activity. Chem Pharm Bull 2005; 53: 832-5.
61. Farias FM, Passos CS, Arbo MD, et al. Strictosidinic acid, isolated from Psychotria myriantha Mull. Arg. (Rubiaceae), decreases serotonin levels in rat hippocampus. Fitoterapia 2012; 83: 1138-43.
62. Dos Santos Passos C, Soldi TC, Torres Abib R, et al. Monoamine oxidase inhibition by monoterpene indole alkaloids and fractions obtained from Psychotria suterella and Psychotria laciniata. J Enzyme Inhib Med Chem 2013; 28: 611-8.
63. Dhingra D, Valecha R. Evidence for involvement of the monoaminergic system in antidepressant-like activity of an ethanol extract of Boerhaavia diffusa and its isolated constituent, punarnavine, in mice. Pharm Biol 2014; 52: 767-74.
64. Zhi KK, Yang ZD, Shi DF, Yao XJ, Wang MG. Desmodeleganine, a new alkaloid from the leaves of Desmodium elegans as potential monoamine oxidase inhibitor. Fitoterapia 2014; 98: 160-5.
65. Krejcova P, Kucerova P, Stafford GI, Jager AK, Kubec R. Antiinflammatory and neurological activity of pyrithione and related sulfur- containing pyridine N-oxides from Persian shallot (Allium stipitatum). J Ethnopharmacol 2014; 154: 176-82.
66. Dittmann K, Gerhäuser C, Klimo K, Hamburger M. HPLC-based activity profiling of Salvia miltiorrhiza for MAO A and iNOS inhibitory activities. Planta Med 2004; 70: 909-13.
67. Kim JH, Kim GH, Hwang KH. Monoamine oxidase and dopamine β-hydroxylase inhibitors from the fruits of Gardenia jasminoides. Biomol Ther 2012; 20: 214-9.
68. Singh R, Ramakrishna R, Bhateria M, Bhatta RS. In vitro evaluation of Bacopa monniera extract and individual constituents on human recombinant monoamine oxidase enzymes. Phytother Res 2014; 28: 1419-22.
69. Okuyama E, Homma M, Satoh Y, et al. Monoamine oxidase inhibitory naphthoquinone and/or naphthalene dimers from Lemuni Hitam (Diospyros sp.), a Malaysian herbal medicine. Chem Pharm Bull 1999; 47: 1473-76.
70. Lee MK, Hwang BY, Lee SA, et al. 1-Methyl-2-undecyl-4(1H)- quinolone as an irreversible and selective inhibitor of type B monoamine oxidase. Chem Pharm Bull 2003; 51: 409-11.
71. Woo HC, Seong SH, Lee SA, et al. Monoamine oxidase inhibitory naphthoquinones from the roots of Lithospermum erythrorhizon. Arch Pharm Res 2005; 28: 400-4.