SAPONINS AND SAPOGENINS OF AGAVE WITH RESPECT TO DIVERSE PHARMACOLOGICAL ROLE OF HECOGENIN

Pharmacological Role of Hecogenin

  • DEEPA K. INGAWALE (MANDLIK) Bharati Vidyapeeth University (Deemed to be University), Poona College of Pharmacy, Erandawane, Pune 411038, Maharashtra, India

Abstract

The review outlines the current understandings of saponins and sapogenins in agave species with special focus on pharmacological role of hecogenin in numerous preclinical studies. A systematic literature survey was done on the pharmacological activities of hecogenin during the past 40 y with electronic databases like PubMed, Science Direct, Wiley, SciFinder, Google Scholar, Web of Science and Scopus. Hecogenin, a steroidal sapogenin found abundantly in the leaves of Agave genus species such as, Agave sisalana, Agave cantala, Agave aurea and many more. This phytosteroid (hecogenin) is used as initial material for the synthesis of steroidal drugs in the pharmaceutical industry. Hecogenin has exhibited potential role in the management of a number of disorders such as inflammation, arthritis, cancer, gastric ulcer, cardiotonic and larvicidal activity. In this review, we have summarized the saponins and sapogenins present in the Agave species and pharmacological roles of hecogenin with their mechanism of action.

Keywords: Agave genus, Saponin, Sapogenin, Hecogenin, Pharmacological activities

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References

1. Hackman DA, Giese N, Markowitz JS, McLean A, Ottariano SG, Tonelli C, et al. Agave (Agave americana): an evidence-based systematic review by the natural standard research collaboration. J Herb Pharmacother 2006;6:101-22.
2. Nava Cruz NY, Medina Morales MA, Martinez JL, Rodriguez R, Aguilar CN. Agave biotechnology: an overview. Crit Rev Biotechnol 2015;35:546-9.
3. Mellado Mojica E, Lopez MG. Identification, classification, and discrimination of agave syrups from natural sweeteners by infrared spectroscopy and HPAEC-PAD. Food Chem 2015;167:349-57.
4. Jones HD, Furbeck GN, Colorado R. Isolation and study of the saponin content of the juice and leaf of the agave plant, Maguey, Manso fino. J Am Pharm Assoc 1932;21:787-93.
5. Marker RE, Wagner RB, Ulshafer PR, Wittbecker EL, Goldsmith DPJ, Ruof CH. Steroidal sapogenins. J Am Chem Soc 1947;69:2167-230.
6. Simmons Boyce J, Tinto WF. Steriodal saponins and sapogenins from the Agavaceae family. Nat Prod Commun 2007;2:99-114.
7. Santos Zea L, Maria Leal Diaz A, Cortes Ceballos E, Gutierrez Uribe JA. Agave (Agave spp.) and its traditional products as a source of bioactive compounds. Curr Bioact Compd 2012;8:218-31.
8. Guclu Ustundag O, Mazza G. Saponins: properties, applications and processing. Crit Rev Food Sci Nutr 2007;47:231-58.
9. Thakur M, Melzig MF, Fuchs H, Weng A. Chemistry and pharmacology of saponins: special focus on cytotoxic properties. Bot: Targets Ther 2011;1:19-29.
10. Elekofehinti OO. Saponins: anti-diabetic principles from medicinal plants: a review. Pathophysiol 2015;22:95-103.
11. Jiang S, Fan J, Wang Q, Ju D, Feng M, Li J, et al. Diosgenin induces ROS dependent autophagy and cytotoxicity via mTOR signaling pathway in chronicmyeloid leukemia cells. Phytomedicine 2016;23:243-52.
12. Huang B, Du D, Zhang R, Wu X, Xing Z, He Y, et al. Synthesis, characterization and biological studies of diosgenyl analogues. Bioorganic Med Chem Lett 2012;22:7330-4.
13. Chen Y, Tang YM, Yu SL, Han YW, Kou JP, Liu BL, et al. Advances in the pharmacological activities and mechanisms of diosgenin. Chin J Nat Med 2015;13:578-87.
14. Cerqueira GS, Silva GDS, Vasconcelos ER, Fragoso de FAP, Arcanjo MB, Silveira MD, et al. Effects of hecogenin and its possible mechanism of action on experimental models of gastric ulcer in mice. ?Eur J Pharmacol 2012;683:260-9.
15. de Oliveira Rocha HA, Souza do Amaral V. Effect of hecogenin on DNA instability. Toxicol Rep 2016;3:539-43.
16. Ingawale DK, Patel SS. Anti-in?ammatory potential of hecogenin in experimental animals: possible involvement of inflammatory cytokines and myeloperoxidase. Drug Res 2016;66:644-56.
17. Ingawale DK, Patel SS. Hecogenin exhibits anti-arthritic activity in rats through suppression of pro-inflammatory cytokines in complete freund's adjuvant induced arthritis. Immunopharmacol Immunotoxicol 2018;401:59-71.
18. Elsayed HE, Ebrahim HY, Haggag EG, Kamal AM, El Sayed KA. Rationally designed hecogenin thiosemicarbazone analogs as novel MEK inhibitors for the control of breast malignancies. Bioorganic Med Chem 2017;25:6297-312.
19. Hernandez Valle E, Herrera Ruiz M, Salgado GR, Zamilpa A, Ocampo ML, Aparicio AJ, Tortoriello J, et al. Anti-inflammatory effect of 3-O-[(6'-O-Palmitoyl)-?-d-glucopyranosyl Sitosterol] from Agave angustifolia on ear edema in mice. Molecules 2014;19:15624-37.
20. Ahumada Santos YP, Montes Avila J, de Jesus Uribe Beltran M, Diaz Camacho SP, Lopez Angulo G, Vega Avina R, et al. Chemical characterization, antioxidant and antibacterial activities of six Agave species from Sinaloa, Mexico. Ind Crop Prod 2013;49:143-9.
21. Morales Serna JA, Jimenez A, Estrada Reyes R, Marquez C, Cardenas J, Salmon M. Homoisoflavanones from Agave tequilana weber. Molecules 2010;15:3295-301.
22. Almaraz Abarca N, Delgado Alvarado EA, Antonio Avila Reyes J, Uribe Soto JN, Gonzalez Valdez LS. The phenols of the genus Agave (Agavaceae). J Biomat Nanobiotechnol 2013;4:9-16.
23. Rizwan K, Zubair M, Rasool N, Riaz M, Zia-Ul-Haq M, de Feo V. Phytochemical and biological studies of Agave attenuata. Int J Mol Sci 2012;13:6440-51.
24. Agrawal PK, Jain DC, Pathak AK. NMR spectroscopy of steroidal sapogenins and steroidal saponins: an update. Magn Reson Chem 1995;33:923-53.
25. Paik SY, Kok KH, Beak SM, Paek SH, Kim JA. The essential oils from Zanthoxylum schinifolium pericarp induce apoptosis of HepG2 human hepatoma cells through increased production of reactive oxygen species. Biol Pharm Bull 2005;28:802-7.
26. Eskander J, Lavaud C, Harakat D. Steroidal saponins from the leaves of Agave macroacantha. Fitoterapia 2010;81:371-4.
27. Santos J, Vieira I, Braz Filho R, Branco A. Chemicals from Agave sisalana biomass: isolation and identification. Int J Mol Sci 2015;16:8761-71.
28. Gama KB, Quintans JS, Antoniolli AR, Quintans Junior LJ, Santana WA, Branco A, et al. Evidence for the involvement of descending pain-inhibitory mechanisms in the antinociceptive effect of hecogenin acetate. J Nat Prod 2013;76:559-63.
29. Corbiere C, Liagre B, Bianch A, Bordji K, Dauça M, Netter P, Beneytout JL. Different contribution of apoptosis to the anti-proliferative effects of diosgenin and other plant steroids, hecogenin and tigogenin, on human 1547 osteosarcoma cells. Int J Oncol 2003;22:899-905.
30. Quintans JSS, Barreto RSS, de Lucca W, Villarreal CF, Kaneto CM, Soares MBP, et al. Evidence for the involvement of spinal cord-inhibitory and cytokines modulatory mechanisms in the anti-hyperalgesic effect of hecogenin acetate, a steroidal sapogenin-acetylated, in mice. Molecules 2014;19:8303-16.
31. Morikawa T, Li N, Nagatomo, A Matsuda H, Li X, Yoshikawa M. Triterpene saponins with gastroprotective effects from tea seed (the seeds of Camellia sinensis). J Nat Prod 2006;69:185-90.
32. Serafini LJ, Quintans MR, Antoniolli JSS, Viana dos Santos MR, Quintans Junior LJ. Mapeamento de tecnologias patenteaveis com o uso da hecogenina. Rev Geintec 2012;2:427-35.
33. Vinueza D, Lopez E, Acosta K, Abdo S. Assessment of anti-inflammatory activity and cytotoxicity of freeze dried hydroalcoholic extract of bidens andicola on isolated neutrophils. Asian J Pharm Clin Res 2017;10:160-3.
34. Akanda MR, Park BY. Involvement of MAPK/NF-kappab signal transduction pathways: Camellia japonica mitigates inflammation and gastric ulcer. Biomed Pharmacother 2017;95:1139-46.
35. Yoshimura M, Furue H. Mechanisms for the anti-nociceptive actions of the descending noradrenergic and serotonergic systems in the spinal cord. J Pharmacol Sci 2006;101:107-17.
36. Oliveira L, Lacerda D, Nunes F. Effects of hecogenin on larvicidal activity against Aedes aegypti mosquito, the dengue vector. BMC Proc 2014;8:P33.
37. Khazaei M, Salehi H. Protective effect of Falcaria vulgaris extract on ethanol induced gastric ulcer in rat. Iranian J Pharmacol Ther 2006;5:1-4.
38. Sonnenberg A. Geographic and temporal variations in the occurrence of peptic ulcer disease. Scand J Gastroenterol Suppl 1996;110:11-24.
39. Shristi B, Neha J, Indu BP, Rajesh G. A review on some Indian medicinal plants for antiulcer activity. J Sci Res Pharm 2012;1:6-9.
40. Griffin MR, Scheiman JM. Prospects for changing the burden of nonsteroidal anti-inflammatory drug toxicity. Am J Med 2001;110:33S-7S.
41. Akah PA, Orisakwe OE, Gamanies KS, Shittu A. Evaluation of nigerian traditional medicines: II. Effects of some Nigerian folk remedies on peptic ulcer. J Ethnopharmacol 1998;62:123-7.
42. Hawkins C, Hanks GW. The gastroduodenal toxicity of nonsteroidal anti-inflammatory drugs. A review of the literature. J Pain Symptom Manage 2000;202:140-51.
43. Smolen JS, Aletaha D, Koeller M, Weisman MH, Emery P. Emery, new therapies for treatment of rheumatoid arthritis. Lancet 2007;370:1861-74.
44. Nishat F, Syeda JF. Pharmacological screening for anti-arthritic activity of Moringa oleifera. Asian J Pharm Clin Res 2016;9:106-11.
45. Tastekin N, Aydogdu N, Dokmeci D, Usta U, Birtane M, Erbas H, et al. Protective effects of l-carnitine and alpha-lipoic acid in rats with adjuvant arthritis. Pharmacol Res 2007;56:303-10.
46. Liagre B, Vergne Salle P, Leger DY, Beneytout JL. Inhibition of human rheumatoid arthritis synovial cell survival by hecogenin and tigogenin is associated with increased apoptosis, p38 mitogen-activated protein kinase activity and upregulation of cyclooxygenase-2. Int J Mol Med 2007;20:451-60.
47. Saka S, Singh AN, Sharma N. Potential anti-cancer superfoods: a minireview. Int J Curr Pharm Res 2016;8:19-21
48. Torre LA, Bray F, Siegel RL, Ferlay J, Lortet Tieulent J, Jemal A. Global cancer statistics. CA Cancer J Clin 2012;652:87-108.
49. Cruz MS, Cabral Barroso S, Navoni JA, Rocha Silva Teles MM, Barbosa-Filho JM, de Oliveira Rocha HA, et al. Effect of hecogenin on DNA instability. Toxicol Rep 2016;3:539-43.
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INGAWALE (MANDLIK), D. K. “SAPONINS AND SAPOGENINS OF AGAVE WITH RESPECT TO DIVERSE PHARMACOLOGICAL ROLE OF HECOGENIN”. International Journal of Pharmacy and Pharmaceutical Sciences, Vol. 12, no. 2, Jan. 2020, pp. 1-7, doi:10.22159/ijpps.2020v12i2.35789.
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