Phytochemical analysis and in vitro antimicrobial screenings of the methanolic stem bark extract and constituents of Parkia bicolor A. Chev. (Leguminosae)
Subject Areas : Phytochemistry: Isolation, Purification, CharacterizationAicha De Nkainsa 1 , Simplice Chimi Fotso 2 , Angelbert Awantu Fusi 3 , Francioli Korokoro 4 , Toze Flavien Aristide Alfred 5 , Jean Duplex Wansi 6 , Paul Désiré Dzeufiet Djomeni 7 , Alain Bertrand Dongmo 8 , Théophile Dimo 9
1 - Laboratory of Physiology, Department of Animal Biology, Faculty of Science, the University of Yaounde, Cameroon
2 - Laboratory of Chemistry, Department of Chemistry, Faculty of Science, the University of Douala, Cameroon
3 - Department of Chemistry, Faculty of Science, the University of Bamenda, Bambili, Cameroon
4 - Laboratory of Biochemistry, Department of Biochemistry, Faculty of Science, the University of Douala, Cameroon
5 - Laboratory of Chemistry, Department of Chemistry, Faculty of Science, the University of Douala, Cameroon
6 - Laboratory of Chemistry, Department of Chemistry, Faculty of Science, the University of Douala, Cameroon
7 - Laboratory of Physiology, Department of Animal Biology, Faculty of Science, the University of Yaounde, Cameroon
8 - Laboratory of Physiology and Animal Biology, Department of Animal Organisms Biology, Faculty of Science, the University of Douala, Cameroon
9 - Laboratory of Physiology, Department of Animal Biology, Faculty of Science, the University of Yaounde, Cameroon
Keywords: Ethnopharmacology, Antimicrobial Activity, <i>Parkia bicolor</i> A. Chev, Leguminosae, Secondary metabolites,
Abstract :
The phytochemical study of the methanolic extract of the stem bark of Parkia bicolor A. Chev. (Leguminosae) led to the isolation and characterization of ellagic acid (1), 3,3’-dimethoxyel lagic acid (2), 3,3’,4,4’-tetramethoxyellagic acid (3), 3-glucopyranoside-3’-methoxyellagic acid (4), gallic acid (5), methylgallate (6), oleanolic acid (7), erythrodiol (8), β-amyrin (9), β-sitosterol (10), stigmasterol (11) and stigmasterol-3-O-β-D-glucopyranoside (12). The structures of these compounds were determined by spectroscopic analyses of 1D and 2D NMR and EI- and ESI-MS and comparison with the reported data. Compounds 1-4 are reported here from this species for the first time. The crude methanolic extract and isolated compounds 1-6 were submitted to micro dilution assay against the Gram negative bacteria Escherichia coli ATCC 8739 and Salmonella typhi clinical strain as well as the Gram positive bacterium Staphylococcus aureus clinical strain. While the methanolic extract showed moderate to significant antibacterial activ ity against above tests strain with MICs in the range of 64-128 μg/mL, compound 4 displayed the best activity against Salmonella typhi and Staphylococcus aureus clinical strains with an MIC of 33.4 μM against both, compared to gentamycin with 0.1-2.0 μM. Compounds 1-3 and 5, 6 showed moderate to weak antibacterial activity with MICs in the range of 44.6 ± 0.9 to 376.4 ± 1.5 μM. MBCs were above the MICs in the range of 128-512 μg/mL for the methanolic extract resulting in MBCs/MICs in the range of 2 to 8. In antifungal assays, the methanolic extract when tested at 50 mg/mL gave growth inhibition of 34.3, 31.3, 28.3, 33.1, 30.6 and 22.4 % against Aspergillus flavus strain 1, Aspergillus flavus strain 2, Aspergillus niger, Aspergillus gandidus, Ab sidia sp < /em>. and Penicillium sp < em>., respectively. When tested at 2 mg/mL, 4-glucopyranoside-4’-me thoxyellagic acid (4) showed a moderate inhibition potency against all the fungal strains with growth inhibition of 24.50 to 40.40% compared to fluconazole with 100% at 2 mg/mL.
Abioye, E.O., Akinpelu, D.A, Aiyegoro, O.A, Adegboye, M.F, Oni, M.O., Okoh, A.I., 2013. Preliminary phytochemical screening and antibacterial properties of crude stem bark extracts and fractions of Parkia biglobosa (Jacq.). Molecules 18(7), 8485-8499.
Agunu, A., Yusuf, S., Andrew, G.O., Zezi, A.U., Abdurahman, E.M., 2005. Evaluation of five medicinal plants used in diarrhoea treatment in Nigeria. J. Ethnopharmacol. 101(1-3), 27-30.
Ahmad, N.I., Rahman, S.A., Leong, Y.-H., Azizul, N.H., 2019. A review on the phytochemicals of Parkia speciosa, stinky beans as potential phytomedicine. J. Food Sci. Nutr. Res. 2(3), 151-173.
Ajaiyeoba, E.O., 2002. Phytochemical and antibacterial properties of Parkia biglobosa and Parkia bicolor leaf extracts. Afr. J. Biomed. Res., 5(3), 125-129.
Bag, P.K., Roy, N., Acharyya, S., Saha, D.R., Koley, H., Sarkar, P., Bhowmik, P., 2019. In vivo fluid accumulation-inhibitory, anticolonization and anti-inflammatory and in vitro biofilm-inhibitory activities of methyl gallate isolated from Terminalia chebula against fluoroquinolones resistant Vibrio cholerae.Microb. Pathogenesis 128, 41-46.
CLSI. Methods for Dilution Antimicrobial Susceptibility Tests for Bacteria That Grow Aerobically; Approved Standard—Tenth Edition. CLSI document M07-A10. Wayne, PA: Clinical and Laboratory Standards Institute; 2015.
De, R., Sarkar, A., Ghosh, P., Ganguly, M., Karmakar, B.C., Saha, D.R., Halder, A., Chowdhury, A., Mukhopadyay, A.K., 2018. Antimicrobial activity of ellagic acid against Helicobacter pylori isolates from India and during infections in mice. J. Antimicrob. Chemother. 73(6), 1595-1603.
De Cock, P., 2012. Erythrodiol. In: Sweeteners and Sugar Alternatives in Food Technology, Second Edition, Chapter 10. Dr Kay O´Donnell, Dr. Malcolm W. Kearsley (Eds.)
Dhaouadi, K., Raboudi, F., Estevan, C., Barrajon, E., Vilanova, E., Hamdaoui, M., Fattouch, S., 2010. Cell viability effects and antioxidant and antimicrobial activities of Tunisian date syrup (Rub El Tamer) polyphenolic extracts. J. Agric. Food Chem.59(1), 402-406.
Djeugap, J.F., Fontem, D.A., Tapondjou, A.L., 2011. Efficacité in vitro et in vivo des extraits de plants contre le mildiou (Phytophthora infestans) de la morelle noire. Int. J. Biol. Chem. Sci. 5(6), 2205-2213.
Djeussi, D.E, Noumedem J.A.K., Seukep, J.A., Fankam, A.G., Voukeng I.K., Tankeo, S.B., Nkuete, H.L., Kuete, V., 2013. Antibacterial activities of selected edible plants extracts against multidrug-resistant Gram-negative bacteria. BMC Complement. Altern. Med., 13, 164-172.
Duker-Eshun, G., Beni, C.T., Asomaning, W.A., Akuamoah, R.K., 2001. Chemical investigations of the stem-bark of Parkia clappertoniana Keay. J. Ghana Sci. Assoc. 3(2), 95-101.
Fotie, J., Nkengfack A.E., Peter, M.G.., Heydenreich, M., Fomum, Z.T., 2004. Chemical Constituents of the Ethyl Acetate Extracts of the Stem Bark and Fruits of Dichrostachys Cinerea and the Roots of Parkia bicolor. Bull. Chem. Soc. Ethiop. 18(1), 111-115.
Hagos, T.H., 1962. A revision of the genus Parkia R.Br. (Mim.) in Africa. Acta Bot. Neerl. 11(3), 231-265.
Hopkins, H.C., 1986. Parkia (Leguminosae: Mimosoideae). Flora Neotrópica Monograph, 43-117.
Jabeen, K., Javaid, A., Ahmad, E., Athar, M., 2011. Antifungal compounds from Melia azederach leaves for management of Ascochyta rabiei, the cause of chickpea blight. Nat. Prod. Res. 25(3), 264-276.
Lahlou, M., 2004. Methods to study the photochemistry and bioactivity of essential oils. Phytother. Res. 18, 435-448.
Lawal, I.O., Uzokwe, N.E., Igboanugo, A.B.I., Adio, A.F., Awosan, E.A., Nwogwugwu, J.O., Faloya, B., Olantunji, B.P., Adesoga, A.A., 2010. Ethno medicinal information on collation and identification of some medicinal plants in research institutes of South-west Nigeria. Afr. J. Pharm. Pharmacol. 4(1), 1-7.
Lee, D.-S., Eom, S.-H., Kim, Y.-M., Kim, H.-S., Yim, M.-J., Lee, S.-H., Kim, D.-H., Je, J.-Y., 2014. Antibacterial and synergic effects of gallic acid-grafted-chitosan with β-lactams against methicillin-resistant Staphylococcus aureus (MRSA). Can. J. Microbiol. 60(10), 629-638.
Lemmens, R.H.M.J., 2008. Parkia filicoidea Welw. ex Oliv. Record from PROTA4U, in: Louppe, D., Oteng-Amoako, A.A. & Brink, M. (Editors). PROTA (Plant Resources of Tropical Africa/Ressources végétales de l’Afrique tropicale), Wageningen, Netherlands. Protologue: Fl. Trop. Afr. 2, 324 (1871).
Leroux, P., Gredt, M., Fritz, R., 1978. Laboratory Investigations on Stems of Some Phytopathogenic Fungi (Botrytis, Monilia, Sclerotinia, Rhizoctonia) Resistant to Dichlozolin, Dicyclidin, Iprodione, Vinchlozolin and Aromatic Hydrocarbon Fungicides. Institut National de la Recherche Agronomique (I.N.R.A.), Versailles (France). Lab. de Phytopharmacie, 30, 881-889. (French)
Lima, V.N., Oliveira-Tintino, C.D.M., Santos, E.S., Morais, L.P., Tintino, S.R., Freitas, T.S., Geraldo, Y.S., Pereira, R.L.S., Cruz, R.P., Menezes, I.R.A., Coutinho, H.D.M., 2016. Antimicrobial and enhancement of the antibiotic activity by phenolic compounds: gallic acid, caffeic acid and pyrogallol. Microb. Pathog. 99, 56-61.
Liu, C., Chen, C., Mo, H., Ma, H., Yuan, E., Li, Q., 2014. Characterization and DPPH radical scavenging activity of gallic acid-lecithin complex. Trop. J. Pharm. Res. 13(8), 1333-1338.
Matsuzawa, T., 2007. Assessment of the Planted Trees in Green Corridor Project. Pan-Africa News, 14(2), 27-29.
Michiels, J.E., Van den Berg, B., 2016. Molecular mechanisms and clinical implications of bacterial persistance. Drug Resist. Updat. 29(2016), 76-89.
Mouokeu R.S, Ngono N.A.R, Lunga P.K, Koanga M.M, Tiabou A.T, Njateng G.S.S, Tamokou J.D.D, Kuiate J.R., 2011. Antibacterial and dermal toxicological profiles of ethyl acetate extract from Crassocephalum bauchiense (Hutch.) Milne-Redh (Asteraceae). BMC Complement. Altern. Med. 11, 43-10.
Mouokeu, R.S., Ngane, R.A.N., Njateng, G.S.S., Kamtchueng, M.O., Kuiate, J.-R., 2014. Antifungal and antioxidant activity of Crassocephalum bauchiense (Hutch.) Milne-Redh ethyl acetate extract and fractions (Asteraceae). BMC Res. Notes 7(244), 1-7.
Oh, E. and Jeon, B., 2015. Synergistic anti-Campylobacter jejuni activity of fluoroquinolone and macrolide antibiotics with phenolic compounds. Front. Microbiol. 13(6), 1129-1150
Paranagama, P.A., Abeysekera, K.H.T., Abeywickrama, K., Nugaliyadde L., 2003. Fungicidal and anti-aflatoxigenic effects of the essential oil of Cymbopogon citratus (DC.) Stapf. (Lemongrass) against Aspergillus flavus Link. isolated from stored rice. Lett. Appl. Microbiol. 37(1), 86-90.
Park, S.N., Lim, Y.K., Choi, M.H., Cho, E., Bang, I.S., Kim, J.M., Ahn, S.J., Kook, J. K., 2018. Antimicrobial mechanism of oleanolic and ursolic acids on Streptococcus mutans UA159. Curr. Microbiol. 75(1), 11-19.
Salie, F., Eagles, P.F.K., Leng H.M.J., 1996. Preliminary antimicrobial screening of four South African Asteraceae species. J. Ethnopharmacol. 52, 27-33.
Sykes, J.E., Rankin, S.C., 2014. Isolation and identification of Aerobic and Anaerobic Bacteria. In: Canine and Feline Infectious Diseases. St. Louis: Elsevier Inc., 17-28.
Shao, D., Li, J., Li, J., Tang, R., Liu, L., Shi, J., Huang, Q., Yang, H., 2015. Inhibition of gallic acid on the growth and biofilm formation of Escherichia coli and Streptococcus mutans. J. Food Sci. 80(6), 1299-1305.
Tchinda, A.T., 2008. Parkia bicolor A. Chev. In: Louppe, D., Oteng-Amoako, A.A., Brink, M. (Editors). Plant Resources of Tropical Africa 7(1). Timbers 1. Prota Foundation, Wageningen, Netherlands/Backhuys Publishers, Leiden, Netherlands / CTA, Wageningen, Netherlands, pp. 415-420.
The Plant List, 2013. Version 1.1. Published on the Internet; http://www.theplantlist.org/
Udobi, C.E. Onaolapo, J.A., 2009. Phytochemical analysis and antibacterial evaluation of the leaf stem bark and root of the African locust bean (Parkia biglobosa). J. Med. Plants Res. 3(5), 338-344.
World Health Organization (WHO), 2017. Global Priority List of Antibiotic-Resistant Bacteria to Guide Research, Discovery, and Development of New Antibiotics. Essential Medicines and Health Products, 7 p.
Ye, G., Peng, H., Fan, M., Huang, C.-G., 2007. Ellagic acid derivatives from the stem bark of Dipentodon sinicus. Chem. Nat. Compd. 43(2), 125-127.