Issue

Vol. 32 No. 8 (2020): Vol 32 Issue 8, 2020

Creative Commons License

This work is licensed under a Creative Commons Attribution 4.0 International License.

Annonaine an Alkaloid from the Leaves of Custard Apple (Annona squamosa): A Comprehensive Review on its Phytochemicals and Pharmacological Activities

https://doi.org/10.14233/ajchem.2020.22696
S. Dash
School of Pharmacy and Life Sciences, Centurion University of Technology and Management, Khurda-752050, India
https://orcid.org/0000-0003-1618-6746
B. Kar
School of Pharmacy and Life Sciences, Centurion University of Technology and Management, Khurda-752050, India
https://orcid.org/0000-0002-4530-1005
N. Sahoo
School of Pharmacy and Life Sciences, Centurion University of Technology and Management, Khurda-752050, India
G. Pattnaik
School of Pharmacy and Life Sciences, Centurion University of Technology and Management, Khurda-752050, India

Corresponding Author(s) : S. Dash

sdash1983@gmail.com

Asian Journal of Chemistry, Vol. 32 No. 8 (2020): Vol 32 Issue 8, 2020

Abstract

Annona squamosa is most widely distributed in tropical and subtropical region native to tropical America comes under the Annonaceae family. It is a widely used tree having edible fruits called as custard apple which is eatable. Annona squamosa plant also contains 35-42 mg/100 g of vitamin C and significant value of nutrient like thiamine, amino acid, riboflavin, niacin, calcium, potassium and dietary fibers. It also contains the phytoconstituents like diterpenes, alkaloids, cyclopeptides and annonaceous acetogenins proved by phytochemistry  investigations. The plant Annona squamosa show a number of pharmacological activities like insecticidal, anticancer, hypoglycemic, antioxidant, antimalarial, analgesic and wound healing activity. The vermicidal effect of leaves is responsible for the treatment of tumors, wounds and other skin infections. A number of alkaloids were isolated from the leaves of plant. Most of them belong to aporphine group of alkaloids. Among all the phytoconstituents an alkaloid Annonaine, plays a vital role for its biological activity. The present review represents the phytochemical constituents, biological action, traditional as well as medicinal uses of Annona squamosa. Sugar apple might be the better explored plant part used in treatment of many disorders and the present critical study will hopefully provide a disease free and healthy life to the human society. 

Keywords

Annona squamosa Traditional medicine Phytochemicals Alkaloid annonaine Pharmacological activity
Dash, S. ., Kar, B. ., Sahoo, N., & Pattnaik, G. . (2020). Annonaine an Alkaloid from the Leaves of Custard Apple (Annona squamosa): A Comprehensive Review on its Phytochemicals and Pharmacological Activities. Asian Journal of Chemistry, 32(8), 1824–1836. https://doi.org/10.14233/ajchem.2020.22696
Download Citation
Endnote/Zotero/Mendeley (RIS)
BibTeX
References
  1. S.Z. Moghadamtousi, B.H. Goh, C.K. Chan, T. Shabab and H.A. Kadir, Molecules, 18, 10465 (2013); https://doi.org/10.3390/molecules180910465
  2. M. Zahid, M. Mujahid, P.K. Singh, S. Farooqui, K. Singh and S. Parveen, Int. J. Pharm. Sci. Res., 9, 1745 (2018).
  3. K.R. Kirtikar and B.D. Basu, Indian Medicinal Plants, Lalit Mohan Basu: Allahabad, India, edn 2, vol. 1, 66 (1980).
  4. S.B. Vohora, I. Kumar and S. Naqvi, Planta Med., 28, 97 (1975); https://doi.org/10.1055/s-0028-1097835
  5. R.K. Gupta, A.N. Kesari, P.S. Murthy, R. Chandra, V. Tandon and G. Watal, J. Ethnopharmacol., 99, 75 (2005); https://doi.org/10.1016/j.jep.2005.01.048
  6. T.R. Seetharaman, Fitoterapia, 57, 189 (1986).
  7. D.S. Bhakuni, S. Tewari and M.M. Dhar, Phytochemistry, 11, 1819 (1972); https://doi.org/10.1016/0031-9422(72)85042-8
  8. P. Forgacs, J.F. Desconclois, R. Provost, R. Tiberghien and A. Touché, Phytochemistry, 19, 1251 (1980); https://doi.org/10.1016/0031-9422(80)83102-5
  9. D.S. Raj, J.J. Vennila, C. Aiyavu and K. Panneerselvam, Int. J. Integr. Biol., 5, 182 (2009).
  10. S. Srivastava, V.K. Lal and K.K. Pant, J. Pharm. Res., 4, 4596 (2011).
  11. J.F. Morton, Sugar Apple, In: Fruits of Warm Climate, Published by Julia F. Morton, 20534 SW 92 Ct. Miami, FL USA, pp 69-72 (2013). ISBN: 0-9610184-1-0.
  12. Germplasm Resources Information Network (GRIN), Taxonomy for Plants USDA, ARS, National Genetic Resources Program, pp 7-11 (1997).
  13. Natural Resources Conservation Service (NRCS), Plants Profile Annona squamosa, United States Department of Agriculture, p 4-17 (2008).
  14. R. Wunderlin and B. Hansen, Synonyms of Annona squamosa: Atlas Florida Vasc Plants, 4, 24-27 (2008).
  15. J.H. Crane, C.F. Balerdi and I. Maguire, Sugar Apple Growing in the Florida Home Landscape, 4, 4-19 (1994).
  16. M. Arif, M. Kamal, T. Jawaid, M. Khalid, K.S. Saini, A. Kumar and M. Ahmad, Asian J. Biomed. Pharm. Sci., 6, 14 (2016).
  17. S. Gajalakshmi, R. Divya, V.D. Deepika, S. Mythili and A. Sathiavelu, Int. J. Pharm. Sci. Rev. Res., 10, 24 (2011).
  18. A. Shirwaikar, K. Rajendran, C.D. Kumar and R. Bodla, J. Ethnopharmacol., 91, 171 (2004); https://doi.org/10.1016/j.jep.2003.12.017
  19. W. Yu, M. Ma, X. Chen, J. Min, L. Li, Y. Zheng, Y. Li, J. Wang and Q. Wang, Am. J. Chin. Med., 45, 1 (2017); https://doi.org/10.1142/S0192415X1750001X
  20. M.M. Rahman, S. Parvin, M.E. Haque, M.E. Islam and M.A. Mosaddik, Fitoterapia, 76, 484 (2005); https://doi.org/10.1016/j.fitote.2005.04.002
  21. R.K. Gupta, A.N. Kesari, S. Diwakar, A. Tyagi, V. Tandon, R. Chandra and G. Watal, J. Ethnopharmacol., 118, 21 (2008); https://doi.org/10.1016/j.jep.2008.03.008
  22. R. Vijayalakshmi and T. Nithiya, World J. Res. Pharm. Pharm. Sci., 4, 1257 (2015).
  23. A.F. Dos Santos and A.E.G. Sant’Ana, Phytomedicine, 8, 115 (2001); https://doi.org/10.1078/0944-7113-00008
  24. J.L. Landolt, K.I. Ahammadsahib, R.M. Hollingworth, R. Barr, F.L. Crane, N.L. Buerckv, G.P. McCabe and J.L. McLaughlin, Chem. Biol. Interact., 98, 1 (1995); https://doi.org/10.1016/0009-2797(95)03628-Y
  25. I.B. ba Ndob, P. Champy, C. Gleye, G. Lewin and B. Akendengué, Phytochem. Lett., 2, 72 (2009); https://doi.org/10.1016/j.phytol.2008.11.006
  26. J.D. Patel and V. Kumar, J. Pharm. Res., 1, 34 (2008).
  27. N. Pandey and D. Barve, Int. J. Res. Pharm. Biomed. Sci., 2, 2229 (2011).
  28. M.J. Chavan, P.S. Wakte and D.B. Shinde, Phytomedicine, 17, 149 (2010); https://doi.org/10.1016/j.phymed.2009.05.016
  29. L.R. Sun, H. Zhu, L.S. Gan, J.X. Mo, F. Feng and C.X. Zhou, China J. Chin. Mater. Med., 37, 2100 (2012).
  30. K.R. Kirtikar and B.D. Basu, Indian Medicinal Plants, Prabasi Press: Allahabad, India (1918).
  31. A.C. Santos, Philipine J. Sci., 43, 561 (1930).
  32. H.T. Li, H.M. Wu, H.L. Chen, C.M. Liu and C.Y. Chen, Molecules, 18, 8257 (2013);https://doi.org/10.3390/molecules18078257
  33. B.H. Chen, H.W. Chang, H.M. Huang, I.W. Chong, J.S. Chen, C.-Y. Chen and H.-M. Wang, J. Agric. Food Chem., 59, 2284 (2011); https://doi.org/10.1021/jf103488j
  34. C.Y. Chen, T.Z. Liu, W.C. Tseng, F.J. Lu, R.P. Hung, C.H. Chen and C.-H. Chen, Food Chem. Toxicol., 46, 2694 (2008); https://doi.org/10.1016/j.fct.2008.04.024
  35. M.C. Zafra-Polo, M.C. González, E. Estornell, S. Sahpaz and D. Cortes, Phytochemistry, 42, 253 (1996); https://doi.org/10.1016/0031-9422(95)00836-5
  36. A. Bermejo, B. Figadère, M.C. Zafra-Polo, I. Barrachina, E. Estornell and D. Cortes, Nat. Prod. Rep., 22, 269 (2005); https://doi.org/10.1039/B500186M
  37. N. Kojima and T. Tanaka, Molecules, 14, 3621 (2009); https://doi.org/10.3390/molecules14093621
  38. J.L. McLaughlin, J. Nat. Prod., 71, 1311 (2008); https://doi.org/10.1021/np800191t
  39. M. Carmen Zafra-Polo, B. Figadère, T. Gallardo, J.R. Tormo and D. Cortes, Phytochemistry, 48, 1087 (1998); https://doi.org/10.1016/S0031-9422(97)00917-5
  40. F.Q. Alali, X.-X. Liu and J.L. McLaughlin, J. Nat. Prod., 62, 504 (1999); https://doi.org/10.1021/np980406d
  41. D.J. Craik, N.L. Daly, T. Bond and C. Waine, J. Mol. Biol., 294, 1327 (1999); https://doi.org/10.1006/jmbi.1999.3383
  42. Y.C. Wu, Y.C. Hung, F.R. Chang, M. Cosentino, H.K. Wang and K.H. Lee, J. Nat. Prod., 59, 635 (1996); https://doi.org/10.1021/np960416j
  43. C.X. Zhou, L.R. Sun, F. Feng, J.X. Mo, H. Zhu, B. Yang, Q.-J. He and L.-S. Gan, Helv. Chim. Acta, 96, 656 (2013); https://doi.org/10.1002/hlca.201200249
  44. Y.Y. Chen, G.G. Bai and Y. Chen, Zhong Yao Cai, 38, 1430 (2015).
  45. S.H. Yeh, F.R. Chang, Y.C. Wu, Y.L. Yang, S.K. Zhuo and T.L. Hwang, Planta Med., 71, 904 (2005); https://doi.org/10.1055/s-2005-871234
  46. Y.L. Yang, F.R. Chang, C.C. Wu, W.Y. Wang and Y.-C. Wu, J. Nat. Prod., 65, 1462 (2002); https://doi.org/10.1021/np020191e
  47. D.K. Yadav, N. Singh, K. Dev, R. Sharma, M. Sahai, G. Palit and R. Maurya, Fitoterapia, 82, 666 (2011); https://doi.org/10.1016/j.fitote.2011.02.005
  48. V.K. Soni, D.K. Yadav, N. Bano, P. Dixit, M. Pathak, R. Maurya, M. Sahai, S.K. Jain and S. Misra-Bhattacharya, Fitoterapia, 83, 110 (2012); https://doi.org/10.1016/j.fitote.2011.09.019
  49. M. Jayendra and Y. Kumar, Int. J. Chem. Anal. Sci., 4, 161 (2013); https://doi.org/10.1016/j.ijcas.2013.08.005
  50. M. You, D.B.M. Wickramaratne, G.L. Silva, H. Chai, T.E. Chagwedera, N.R. Farnsworth, G.A. Cordell, A.D. Kinghorn and J.M. Pezzuto, J. Nat. Prod., 58, 598 (1995); https://doi.org/10.1021/np50118a021
  51. P.K. Bhaumik, B. Mukherjee, J.P. Juneau, N.S. Bhacca and R. Mukherjee, Phytochemistry, 18, 1584 (1979); https://doi.org/10.1016/S0031-9422(00)98511-X
  52. X. Li, X.L. Chen, J.W. Chen and D.D. Sun, Chem. Nat. Compd., 46, 101 (2010); https://doi.org/10.1007/s10600-010-9538-0
  53. D.C. Hopp, F.Q. Alali, Z.M. Gu and J.L. McLaughlin, Bioorg. Med. Chem., 6, 569 (1998); https://doi.org/10.1016/S0968-0896(98)00018-2
  54. Y. Chen, J.W. Chen and X. Li, Phytochem. Lett., 5, 33 (2012); https://doi.org/10.1016/j.phytol.2011.08.015
  55. F. Yuan, G.G. Bai, Y. Chen, Y.J. Miao, J.W. Chen and X. Li, Bioorg. Med. Chem. Lett., 25, 787 (2015); https://doi.org/10.1016/j.bmcl.2014.12.088
  56. Y. Chen, J.W. Chen and X. Li, J. Nat. Prod., 74, 2477 (2011); https://doi.org/10.1021/np200708q
  57. Y. Chen, J.W. Chen, J.H. Zhai, Y. Wang, S.L. Wang and X. Li, Food Chem. Toxicol., 58, 394 (2013); https://doi.org/10.1016/j.fct.2013.05.028
  58. C.M. Li, N.H. Tan, Q. Mu, H.L. Zheng, X.J. Hao and Y. Wu, Phytochemistry, 45, 521 (1997); https://doi.org/10.1016/S0031-9422(96)00829-1
  59. Y.L. Yang, K.F. Hua, P.H. Chuang, S.H. Wu, K. Wu, F.-R. Chang and Y. Wu, J. Agric. Food Chem., 56, 386 (2008); https://doi.org/10.1021/jf072594w
  60. H. Morita, Y. Sato and J. Kobayashi, Tetrahedron, 55, 7509 (1999); https://doi.org/10.1016/S0040-4020(99)00372-5
  61. S. Garg and D. Gupta, J. Essent. Oil Res., 17, 257 (2005); https://doi.org/10.1080/10412905.2005.9698894
  62. C.S. Meira, E.T. Guimarães, T.S. Macedo, T.B. Da Silva, L.R. Menezes, E.V. Costa and M.B.P. Soares, J. Essent. Oil Res., 27, 160 (2015); https://doi.org/10.1080/10412905.2014.982876
  63. M.J. Chavan, D.B. Shinde and S.A. Nirmal, Nat. Prod. Res., 20, 754 (2006); https://doi.org/10.1080/14786410500138823
  64. E.H.A. Andrade, M.G.B. Zoghbi, J.G.S. Maia, H. Fabricius and F. Marx, J. Food Compos. Anal., 14, 227 (2001); https://doi.org/10.1006/jfca.2000.0968
  65. H. Morita, Y. Sato, K.L. Chan, C.Y. Choo, H. Itokawa, K. Takeya and J. Kobayashi, J. Nat. Prod., 63, 1707 (2000); https://doi.org/10.1021/np000342i
  66. T.H. Yang and C.M. Chen, J. Chin. Chem. Soc., 17, 243 (1970); https://doi.org/10.1002/jccs.197000031
  67. Y. Yang, F. Chang and Y. Wu, Helv. Chim. Acta, 87, 1392 (2004); https://doi.org/10.1002/hlca.200490127
  68. H. Morita, T. Iizuka, C.Y. Choo, K.L. Chan, K. Takeya and J. Kobayashi, Bioorg. Med. Chem. Lett., 16, 4609 (2006); https://doi.org/10.1016/j.bmcl.2006.06.008
  69. Y.L. Yang, K.F. Hua, P.H. Chuang, S.H. Wu, K.Y. Wu, F.R. Chang and Y.-C. Wu, J. Agric. Food Chem., 56, 386 (2008); https://doi.org/10.1021/jf072594w
  70. R.-W. Jiang, Y. Lu, Z.-D. Min and Q.-T. Zheng, J. Mol. Struct., 655, 157 (2003); https://doi.org/10.1016/S0022-2860(03)00227-8
  71. F. Lieb, M. Nonfon, U. Wachendorff-Neumann and D. Wendisch, Planta Med., 56, 317 (1990); https://doi.org/10.1055/s-2006-960968
  72. T.G. McCloud, D.L. Smith, C.J. Chang and J.M. Cassady, Experientia, 43, 947 (1987); https://doi.org/10.1007/BF01951681
  73. Y. Fujimoto, T. Eguchi, K. Kakinuma, N. Ikekawa, M. Sahai and Y.K. Gupta, Chem. Pharm. Bull. (Tokyo), 36, 4802 (1988); https://doi.org/10.1248/cpb.36.4802
  74. H. Araya, M. Sahai, S. Singh, A.K. Singh, M. Yoshida, N. Hara and Y. Fujimoto, Phytochemistry, 61, 999 (2002); https://doi.org/10.1016/S0031-9422(02)00351-5
  75. X.H. Li, Y.H. Hui, J.K. Rupprecht, Y.M. Liu, K.V. Wood, D.L. Smith, C.-J. Chang and J.L. McLaughlin, J. Nat. Prod., 53, 81 (1990); https://doi.org/10.1021/np50067a010
  76. D.C. Hopp, F.Q. Alali, Z.M. Gu and J.L. McLaughlin, Phytochemistry, 47, 803 (1998); https://doi.org/10.1016/S0031-9422(97)00822-4
  77. D.C. Hopp, L. Zeng, Z.M. Gu, J.F. Kozlowski and J.L. McLaughlin, J. Nat. Prod., 60, 581 (1997); https://doi.org/10.1021/np9701283
  78. D.C. Hopp, L. Zeng, Z. Gu and J.L. McLaughlin, J. Nat. Prod., 59, 97 (1996); https://doi.org/10.1021/np960124i
  79. S. Bhadra and S.K. Sen, Environ. Ecol., 17, 710 (2002).
  80. R. Yang, X. Zheng, H. Xie, S. Wu and X. Wei, Yunnan Zhi Wu Yan Jiu, 21, 381 (1999).
  81. L. Born, F. Lieb, J.P. Lorentzen, H. Moeschler, M. Nonfon, R. Söllner and D. Wendisch, Planta Med., 56, 312 (1990); https://doi.org/10.1055/s-2006-960967
  82. A. Gypser, C. Bulow and H.D. Scharf, Tetrahedron, 51, 1921 (1995); https://doi.org/10.1016/0040-4020(94)01073-9
  83. H. Araya, N. Hara, Y. Fujimoto, A. Srivastava and M. Sahai, Chem. Pharm. Bull. (Tokyo), 42, 388 (1994); https://doi.org/10.1248/cpb.42.388
  84. R.Z. Yang, X.C. Zheng, G.W. Qin and R.S. Xu, Acta Bot. Sin., 36, 809 (1994).
  85. B.V.V. Pardhasaradhi, M. Reddy, A.M. Ali, A.L. Kumari and A. Khar, Indian J. Biochem. Biophys., 42, 167 (2004).
  86. M.T.S. Saleem, Int. J. Appl. Res. Nat. Prod., 1, 1 (2008).
  87. C. Shenoy, M.B. Patil and R. Kumar, Res. J. Pharmacog. Phytochem., 1, 1 (2009).
  88. S. Singh, Int. J. Pharma Bio Sci., 2, 1183 (2011).
  89. L.P. Padhi, J. Agricultural Tech., 7, 133 (2011).
  90. M. Kaleem, M. Asif, Q.U. Ahmed and B. Bano, Singapore Med. J., 47, 670 (2006).
  91. M. Mujeeb, S.A. Khan, M. Ali, A. Mall and A. Ahmad, Pharm. Res., 2, 59 (2009).
Read More
Author biographies is not available.
Statistic
Read Counter : 9 Download : 16