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Published in: Comparative Clinical Pathology 2/2020

01-04-2020 | Leishmania | Original Article

Antifungal and antileishmanial activities of fractions and isolated isoflavanquinones from the roots of Abrus precatorius

Authors: Emeka E. Okoro, Malik S. Ahmad, Omolaja R. Osoniyi, Funmilayo D. Onajobi

Published in: Comparative Clinical Pathology | Issue 2/2020

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Abstract

Neglected tropical diseases hinder social and economic growth in many tropical areas. We report leishmanicidal activities of isoflavanquinones and antifungal potentials of fractions from methanol root extract of Abrus precatorius. Agar dilution method was used to determine antifungal properties while 96-well dilution protocol was adopted for antileishmanial activities. Ethyl acetate fraction of A. precatorius root extract showed moderate activity against M. canis and F. solani with percentage inhibition of 42.5% and 55.0% respectively while other fractions were inactive. Crude extract, n-hexane, and ethyl acetate fractions demonstrated potent antileishmanial activities with IC50 values of 22.20 ± 0.540 μg/mL, 19.35 ± 0.670 μg/mL, and 6.32 ± 0.001 μg/mL respectively, against L. major. The ethyl acetate fraction, which was the most active fraction, was subjected to successive column chromatography followed by preparative recycling HPLC in order to isolate the active constituents. Structures were established by HR-ESIMS, 1D and 2D NMR (1H, 13C, COSY, NOESY, HMBC, HSQC) spectroscopy. Two compounds were obtained and identified as isoflavanquinones: abruquinone A (1) and abruquinone B (2). Compounds 1 and 2 demonstrated significant (p < 0.05) antileishmanial activity against L. major (IC50 6.35 ± 0.005 μg/mL and 6.32 ± 0.008 μg/mL respectively) and L. tropica (IC50 6.29 ± 0.015 μg/mL and 6.31 ± 0.005 μg/mL, respectively). This appears to be the first report of antileishmanial activity of compounds 1 and 2 from the genus Abrus against cutaneous leishmaniasis and validates the use of A. precatorius in treating dermatology diseases.
Literature
go back to reference Advait SN, Shilpi K, Arun BK, Frantisek S, Andriy B, Casey JM, Valentina M (2014) Recent developments in drug discovery for leishmaniasis and human African trypanosomiasis. Chem Rev 114:11305–11347CrossRef Advait SN, Shilpi K, Arun BK, Frantisek S, Andriy B, Casey JM, Valentina M (2014) Recent developments in drug discovery for leishmaniasis and human African trypanosomiasis. Chem Rev 114:11305–11347CrossRef
go back to reference Alvar J, Ve'lez I, Bern C, Herrero M, Desjeux P, Cano J, den Boe M (2012) Leishmaniasis worldwide and global estimates of its incidence. PLoS One 7(5):e35671CrossRef Alvar J, Ve'lez I, Bern C, Herrero M, Desjeux P, Cano J, den Boe M (2012) Leishmaniasis worldwide and global estimates of its incidence. PLoS One 7(5):e35671CrossRef
go back to reference Androula P, Helena CM (2010) Leishmaniasis, an emerging infection in travelers. Int J Inf Secur 14:e1032–e1039 Androula P, Helena CM (2010) Leishmaniasis, an emerging infection in travelers. Int J Inf Secur 14:e1032–e1039
go back to reference Aziz AR, Volodymyr S, Surendra KJ, Babu LT, Shabana IK, Melissa RJ, Ilias M (2011) Antiparasitic and antimicrobial isoflavanquinones from Abrus schimperi. Nat Prod Commun 6(11):1645–1650 Aziz AR, Volodymyr S, Surendra KJ, Babu LT, Shabana IK, Melissa RJ, Ilias M (2011) Antiparasitic and antimicrobial isoflavanquinones from Abrus schimperi. Nat Prod Commun 6(11):1645–1650
go back to reference Bhardwaj D, Bisht M, Mehta C (1980) Flavonoids from Abrus precatorius. Phytochemistry 19:2040–2041CrossRef Bhardwaj D, Bisht M, Mehta C (1980) Flavonoids from Abrus precatorius. Phytochemistry 19:2040–2041CrossRef
go back to reference Choi Y, Hussain R, Pezzuto J, Kinghorn A, Morton J (1989) Abrusosides A-D, four novel sweet-tasting triterpene glycosides from the leaves of Abrus precatorius. J Nat 52:1118–1127CrossRef Choi Y, Hussain R, Pezzuto J, Kinghorn A, Morton J (1989) Abrusosides A-D, four novel sweet-tasting triterpene glycosides from the leaves of Abrus precatorius. J Nat 52:1118–1127CrossRef
go back to reference Choudhary M, Dur-e-Shahwar PZ, Jabbar A, Ali I, Atta-ur-Rahman (1995) Antifungal steroidal lactones from Withania coagulance. Phytochemistry 40(4):1243–1246CrossRef Choudhary M, Dur-e-Shahwar PZ, Jabbar A, Ali I, Atta-ur-Rahman (1995) Antifungal steroidal lactones from Withania coagulance. Phytochemistry 40(4):1243–1246CrossRef
go back to reference Chutima L, Sinenart S, Prasat K (2004) Antitubercular and antiplasmodial constituents of Abrus precatorius. Planta Med 70:276–278CrossRef Chutima L, Sinenart S, Prasat K (2004) Antitubercular and antiplasmodial constituents of Abrus precatorius. Planta Med 70:276–278CrossRef
go back to reference Gadadhar SS, Karande AA (2013) Abrin immunotoxin: targeted cytotoxicity and intracellular trafficking pathway. PLoS One 8(3):e58304CrossRef Gadadhar SS, Karande AA (2013) Abrin immunotoxin: targeted cytotoxicity and intracellular trafficking pathway. PLoS One 8(3):e58304CrossRef
go back to reference Gathirwa J, Rukunga G, Mwitari P, Mwikwabe N, Kimani C, Muthaura C, Omar S (2011) Traditional herbal antimalarial therapy in Kilifi District, Kenya. J Ethnopharmacol 134:434–442CrossRef Gathirwa J, Rukunga G, Mwitari P, Mwikwabe N, Kimani C, Muthaura C, Omar S (2011) Traditional herbal antimalarial therapy in Kilifi District, Kenya. J Ethnopharmacol 134:434–442CrossRef
go back to reference Ghosal S, Dutta S (1971) Alkaloids of Abrus precatorius. Phytochemistry 10:195–198CrossRef Ghosal S, Dutta S (1971) Alkaloids of Abrus precatorius. Phytochemistry 10:195–198CrossRef
go back to reference Holetz FB, Perrini GL, Sanches NR, Coritez DAG, Nakamura CV, Filho BPD (2002) Screening of some plants used in the Brazilian Folk Medicine for the treatment of Infectious Diseases. Mem I Oswaldo Cruz 97:7CrossRef Holetz FB, Perrini GL, Sanches NR, Coritez DAG, Nakamura CV, Filho BPD (2002) Screening of some plants used in the Brazilian Folk Medicine for the treatment of Infectious Diseases. Mem I Oswaldo Cruz 97:7CrossRef
go back to reference Kalpesh M, Mehta M, Mendpara N, Garmit S, Shah G (2010) Determination of antibacterial activity of MIC of crude extract of Abrus precatorius L. Bitotechnol Adv 10:2 Kalpesh M, Mehta M, Mendpara N, Garmit S, Shah G (2010) Determination of antibacterial activity of MIC of crude extract of Abrus precatorius L. Bitotechnol Adv 10:2
go back to reference Kerry O, Deanna AS, Annette F, Dora M, Michael GR, Mary EB, David MG (2008) Molecular phylogenetic diversity, multilocus haplotype nomenclature, and in vitro antifungal resistance within the Fusarium solani dpecies complex. J Clin Microbiol 46(8):2477–2490CrossRef Kerry O, Deanna AS, Annette F, Dora M, Michael GR, Mary EB, David MG (2008) Molecular phylogenetic diversity, multilocus haplotype nomenclature, and in vitro antifungal resistance within the Fusarium solani dpecies complex. J Clin Microbiol 46(8):2477–2490CrossRef
go back to reference Kishur SC, Ramakant S, Pradeep SP, Vidyadhish AK (2012) Pharmacological activities of Abrus precatorius Linn – a review. Int J Ayurvedic Herb Med 2(2):336–348 Kishur SC, Ramakant S, Pradeep SP, Vidyadhish AK (2012) Pharmacological activities of Abrus precatorius Linn – a review. Int J Ayurvedic Herb Med 2(2):336–348
go back to reference Kuo SC, Chen SC, Chen LH, Wu JB, Wang JP, Teng CM (1995) Potent antiplatelet, anti-inflammatory and antiallergic isoflavanquinones from the roots of Abrus precatorius. Planta Med 61(4):307–312CrossRef Kuo SC, Chen SC, Chen LH, Wu JB, Wang JP, Teng CM (1995) Potent antiplatelet, anti-inflammatory and antiallergic isoflavanquinones from the roots of Abrus precatorius. Planta Med 61(4):307–312CrossRef
go back to reference Lubna M, Syed AS, Rashida A, Syed GS, Rahil A (2018) Antibacterial and antifungal activities of the polyphenolic fractions isolated from the seed coat of Abrus precatorius and Caesalpinia crista. Nat Prod Res 32(23):2835–2839CrossRef Lubna M, Syed AS, Rashida A, Syed GS, Rahil A (2018) Antibacterial and antifungal activities of the polyphenolic fractions isolated from the seed coat of Abrus precatorius and Caesalpinia crista. Nat Prod Res 32(23):2835–2839CrossRef
go back to reference Lunder M (1992) Is Microsporum canis infection about to become a serious dermatological problem? Dermatology 184:87–89CrossRef Lunder M (1992) Is Microsporum canis infection about to become a serious dermatological problem? Dermatology 184:87–89CrossRef
go back to reference Max G, Mark H, Wiliam E, Thomas H, John SL, Elizabeth RS, Richard JS (2013) Review: drug discovery algorithm for cutaneous leishmaniasis. Am J Trop Med Hyg 88(2):216–221CrossRef Max G, Mark H, Wiliam E, Thomas H, John SL, Elizabeth RS, Richard JS (2013) Review: drug discovery algorithm for cutaneous leishmaniasis. Am J Trop Med Hyg 88(2):216–221CrossRef
go back to reference Menan H, Banzouzi J, Hocquette A, Pelissier Y, Blache Y, Kone M, Valentin A (2006) Antiplasmodial activity and cytotoxicity of plants used in West Africa traditional medicine for the treatment of malaria. J Ethnopharmacol 105:131–136CrossRef Menan H, Banzouzi J, Hocquette A, Pelissier Y, Blache Y, Kone M, Valentin A (2006) Antiplasmodial activity and cytotoxicity of plants used in West Africa traditional medicine for the treatment of malaria. J Ethnopharmacol 105:131–136CrossRef
go back to reference Messori A, Fadda V, Maratea D, Trippoli S, Marinaj C (2013) Nephrotoxicity of different formulations of amphotericin B: summarizing evidence by network meta-analysis. Clin Infect Dis 57(12):1783–1784CrossRef Messori A, Fadda V, Maratea D, Trippoli S, Marinaj C (2013) Nephrotoxicity of different formulations of amphotericin B: summarizing evidence by network meta-analysis. Clin Infect Dis 57(12):1783–1784CrossRef
go back to reference Michael S, Michael AK, Richard BB (1985) Pentamidine: a review. Clin Infect Dis 7(5):625–634CrossRef Michael S, Michael AK, Richard BB (1985) Pentamidine: a review. Clin Infect Dis 7(5):625–634CrossRef
go back to reference Reithinger R, Dujardin J, Louzir H, Pirmez C, Alexander B, Brooker S, Lockwood D (2007) Cutaneous leishmaniasis. Clin Dermatol 25:203–211CrossRef Reithinger R, Dujardin J, Louzir H, Pirmez C, Alexander B, Brooker S, Lockwood D (2007) Cutaneous leishmaniasis. Clin Dermatol 25:203–211CrossRef
go back to reference Song C, Hu Z (1998) Abruquinone A, B, D, E, F, and G from the root of Abrus precatorius. Acta Bot Sin 40:734–739 Song C, Hu Z (1998) Abruquinone A, B, D, E, F, and G from the root of Abrus precatorius. Acta Bot Sin 40:734–739
go back to reference Xiao Z, Wang F, Sun A, Li C, Huang C, Zhang S (2012) A new triterpenoid saponin from Abrus precatorius Linn. Molecules 17:295–302CrossRef Xiao Z, Wang F, Sun A, Li C, Huang C, Zhang S (2012) A new triterpenoid saponin from Abrus precatorius Linn. Molecules 17:295–302CrossRef
go back to reference Yoshie H, Melanie R, Samad NE, Stefanie Z, Tsholofelo M, Dashnie N, Mathias H (2013) Antiprotozoal isoflavanquinones from Abrus precatorius ssp. Africanus. Planta Med 79:492–498CrossRef Yoshie H, Melanie R, Samad NE, Stefanie Z, Tsholofelo M, Dashnie N, Mathias H (2013) Antiprotozoal isoflavanquinones from Abrus precatorius ssp. Africanus. Planta Med 79:492–498CrossRef
Metadata
Title
Antifungal and antileishmanial activities of fractions and isolated isoflavanquinones from the roots of Abrus precatorius
Authors
Emeka E. Okoro
Malik S. Ahmad
Omolaja R. Osoniyi
Funmilayo D. Onajobi
Publication date
01-04-2020
Publisher
Springer London
Published in
Comparative Clinical Pathology / Issue 2/2020
Print ISSN: 1618-5641
Electronic ISSN: 1618-565X
DOI
https://doi.org/10.1007/s00580-019-03073-z

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