Chemical constituents and antimicrobial activities of some isolated compounds from the Cameroonian species of Senna alata (Cassia alata L. Roxb synonym, The plant list 2013). (Leguminosae)
الموضوعات :
Simplice Chimi Fotso
1
(Analytical, Structural and Materials Chemistry Laboratory, Department of Chemistry, Faculty of Science, University of Douala, P.O. Box 24157, Douala, Cameroon)
Alain Tcho Tadjong
2
(Department of Chemistry, Faculty of Science, University of Buea, P.O. Box 63, Buea, Cameroon)
Willifred Dongmo Tekapi Tsopgni
3
(Analytical, Structural and Materials Chemistry Laboratory, Department of Chemistry, Faculty of Science, University of Douala, P.O. Box 24157, Douala, Cameroon)
Bruno Lenta
4
(Higher Teachers Training College, University of Yaounde I, P.O. Box 47, Yaounde, Cameroon)
Celine Nkenfou
5
(Head Systems Biology Laboratory CIRCB, of Yaounde I, P.O. Box 3077, Yaounde-Messa, Yaounde, Cameroon)
Jean Duplex Wansi
6
(Analytical, Structural and Materials Chemistry Laboratory, Department of Chemistry, Faculty of Science, University of Douala, P.O. Box 24157, Douala, Cameroon)
Flavien Aristide A. Toze
7
(Analytical, Structural and Materials Chemistry Laboratory, Department of Chemistry, Faculty of Science, University of Douala, P.O. Box 24157, Douala, Cameroon)
الکلمات المفتاحية: Leguminosae, Extraction, <i>Senna alata</i> (<i>Cassia alata</i> L. Roxb, Antimicrobial Activity, synonym), chemical constituents,
ملخص المقالة :
One fatty acid (1), one monoglycol ester (2), three diterpenes (3-5), four steroids (6-9), four triterpenes (10-13), three flavonoids (14-16), three anthraquinones (17-19) and one benzoquinone (20), were isolated from the methanolic extract of the leaves and trunk of Senna alata. These compounds were obtained by extensive silica gel chromatography and their structures elucidated by 1D and 2D nuclear magnetic resonance (NMR) as well as comparison with literature data. Compounds (2-4) have been reported for the first time from this species. Some isolated compounds and methanolic crude extract of leaves and trunk were screened in vitro for their antimicrobial activities. Kaempferol (16) exhibited strong activity against all the tested strains, with MIC values varying from 15.5 to 31.2 µg/mL, emodin (18) was active with a strong activity (7.8 µg/mL) exhibited on Pseudomonas aeruginosa. The trunk crude extract showed a strong activity with MIC values varying from 15.6 to 62.5 µg/mL.
Adjanahoun, E., Ahyi, M.R.A., Ake-Assi, L., Elewude, J.A., Fadoju, S.O., Gbile, Z.O., Goudole, E., Johnson, C.L.A., Keita, A., Morakinyo, O., Ojewole, J.A.O., Olatunji, A.O., Sofowora, E.A., 1991. Traditional Medicine and Pharmacopoeia. Contribution to Ethnobotanical Floristic Studies in Western Nigeria, Organization of African Unity Scientific, Technical and Research Commission, OAU/STRC Pub., Lagos, Nigeria, p. 420.
Arunava, G., Aminata, S., Porika, V., Pulok, K., Mukherjee, Pradeep, K.D., 2010. Isolation of taraxerol from Coccinia grandis and its standardization. J. Planar Chromatogr.-Mod. TLC. 23(5), 323-325.
Castilho, R.O., Kaplan, M.A.C., 2008. Chemical constituents of Licania tomentosa Benth. (Chrysobalanaceae). Quim. Nova 31(1), 66-69.
Vargas, F.D.S., De Almeida, P.D.O., Aranha, E.S.P., Boleti, A.P.D.A., Newton, P., De Vasconcellos, M.C., Veiga, V.F., Jr., Lima, E.S., 2015. Biological activities and cytotoxicity of diterpenes from Copaifera spp. oleoresins. Molecules 20(4), 6194-210.
Eloff, J.N., 1998. A sensitive and quick microplate method to determine the minimal inhibitory concentration of plant extracts for bacteria. Planta Med. 64(8), 771-713.
Esposito , F., Sanna, C., Del Vecchio, C., Cannas, V., Venditti, A., Corona, A., Bianco, A., Serrilli, A.M., Guarcini, L., Parolin, C., Ballero, M., Tramontano, E., 2013. Hypericum hircinum L. components as new single-molecule inhibitors of both HIV-1 reverse transcriptase-associated DNA polymerase and ribonuclease H activities. Pathog. Dis. 68(3), 116-24.
Kalidhar, S.B., 1993. Alatinone, an Anthraquinone from Cassia alata. Phytochemistry 32(6), 1616-1617.
Igoli, J.O., Ogaji, O.G., Igoli, N.P., Tor-Anyiin, T.A., 2005. Traditional medicinal practices among the Igede people of Nigeria (part II). Afr. J. Tradit. Complement. Altern. Med., 2(2), 134-152.
Ross, I.A., 2003. Chemical Constituents, Traditional and Modern Medicinal Uses. Medicinal plants of the world, Vol. 1
Kuete, V., 2010. Potential of Cameroonian plants and derived products against microbial infections: A review. Planta Med. 76(14), 1479-1491.
Liu, H.C., Jin, Y.S., Chenhai, S., 2013. Study on triterpenoid and flavonoid contents of Rabdosia japonica. Acad. J. Second Mil. Med. Univ. 34(10), 1121-1124.
Maiyo, F., Moodley, R., Singh, M., 2016. Phytochemistry, cytotoxicity and apoptosis studies of β-sitosterol-3- O-glucoside and β-amyrin from Prunus africana. Afr. J. Tradit. Complement. Altern. Med. 105-112. doi: 10.21010/ajtcam.
Makinde, A.A., Igoli, J.O., TA’Ama, L.S., Shaibu, J., Garba, A., 2007. Antimicrobial activity of Cassia alata. Afr. J. Biotechnol. 6(13), 1509-1510.
Mbouangouere, R.N., Tane, P., Ngamga, D., Djemgou, P., Choudhary, M.I., Ngadjui, B.T., 2007. Piptaderol from Piptadenia africana. Afr. J. Tradit. Complement. Altern. Med. 4(3), 294-298.
Mohammadhosseini, M., 2017. The ethnobotanical, phytochemical and pharmacological properties and medicinal applications essential oils and extracts if different Ziziphora species. Ind. Crop Prod. 105(1), 164-192.
Mohammadhosseini, M., Sarker, S.D., Akbarzadeh, A., 2017. Chemical composition of the essential oils and extracts of Achillea species and their biological activities: A review. J. Ethnopharmacol. 199, 257-315.
Mohammadhosseini, M., Venditti, A., Sarker, S.D., Nahar, L., Akbarzadeh, A., 2019. The genus Ferula: Ethnobotany, phytochemistry and bioactivities- A review. Ind. Crop Prod. 129, 350-394.
Moreno-Anzúrez, N.E., Marquina, S.A.L., Zamilpa, A., Castillo-España, P., Perea-Arango, I., Torres, P.N., Herrera-Ruiz, M., Díaz G.E.R., García, J.T., Arellano-García, J., 2017. A cytotoxic and anti-inflammatory campesterol derivative from genetically transformed hairy roots of Lopezia racemosa Cav. (Onagraceae). Molecules 22(1), 118. doi: 10.3390/molecules28085103.
Kupchan, S.M., Obasi, M.E., 1960. A note on the occurrence of 2,6-dimethoxybenzoquinone in Rauwolfia vomitoria. J. Am. Pharm. Assoc. 49(4), 257-258.
Muhammad, I., Abdur, R., Tareq, A-I., Muhammad, N., Mohammad, A.S., Imtiaz, A.K., Ali, I., Ilkay, E.O., Muhammad, R., Muhammad, A., Tanweer, A.G., Mohammad, S.M., 2020. Luteolin, a flavonoid as an anticancer agent: A review. Biomed. Pharmacother. 112. doi: 10.1016/j. biopha.2019.108612.
Nguyen, C.T.T., Ninh, T.S., Do, T.T., Nguyen, M.C., 2016. Kaempferol and kaempferol glycosides from Phyllanthus acidus leaves. Vietnam J. Chem. Int. Ed. 54(6), 790-793.
Oluwole, S.O., Funmilayo, E. A., Abimbola, P.O., Deborah, T.B., 2020. Ethnobotanical, description and biological activities of Senna alata. Hindawi. Evid. Based Complement. Alternat. Med. 1-12. doi: org/10.1155/2020/2580259.
Patocka, J., 2003. Biologically active pentacyclic triterpenes and their current medicine signification. J. Appl. Biomed. 1, 7-12. doi: 10.3275/jab.2003.002
Pavunraj, M., Ramasubbu, G., Baskar, K., 2017. Leucas aspera (Willd.) L.: Antibacterial, antifungal and mosquitocidal activities. Trends Phytochem. Res. 1, 135-142.
Prakash, C.V.S., Zhijie, G., Sidney, M., Hecht, S.H., Jones, D.G.I., Kingston, 2003. A new acylated oleanane triterpenoid from Couepia polyandra that inhibits the lyase activity of DNA polymerase. J. Nat. Prod. 66(11), 1463-1465. doi: org/10.1021/np0301893.
Prateeksha, Mohd, A.Y., Brahma, N.S., Surya, S., Ravindra, N.K., Saba, S., Ahmed, M.A-A., Leonardo, F.F., Kavya, D., Vijai, K.G., 2019. Review. Chrysophanol: A natural anthraquinone with multifaceted biotherapeutic potential. Biomolecules 9(2), 68. doi: org/10.3390/biom9020068
Qu, C., Yue, S.J., Lin, H., Kai, J., Shang, G.X., Tang, Y.P., Tao, W.W., Duan, J.A., 2015. Chemical constituents of Carthamus tinctorius L. Chin. Tradit. Herbal Drugs. 46(13), 1872-1877. doi: 107501/J.issn.0253-2670.2015.13.003
Refaz, A.D., Rabiya, M., Abid, A.S., Shakeel, R., Abid, H., Qazi, P.H., 2017. Emodin, isolated and characterized from an endophytic fungus Polyporales sp., induces apoptotic cell death in human lung cancer cells through the loss of mitochondrial membrane potential. J. Phytopharmacol. 6(5), 288-292.
Shabina, P., Anwar, S., 2015. A review on in vitro culture of Cassia alata Linn (Senna alata). Analysis of metabolites and biological activities. J. Functional Environ. Bot. 5(2), 78-86. doi: 10.5958/2231-1750.2015.00016.5.
The Plant List, 2013. Version 1.1. Published on the Internet; http://www.theplantlist.org/.
Wansi, J.D., Sewald, N., Lutfun, N., Claire, M., Satyajit, S.D., 2018. Bioactive essential oils from the Cameroonian rain forest: A review- Part I. Trends Phytochem. Res. 2(4), 187-234.
Wansi, J.D., Sewald, N., Lutfun, N., Claire, M., Satyajit, S.D., 2019. Bioactive essential oils from the Cameroonian rain forest: A review- Part II. Trends Phytochem. Res. 3(2), 3-52.
Yarimar, R., Rodrigues, J., Arvelo, F., Usubillaga, A., Monsalve, M., NardyDiez, I.G-C., 2008. Cytotoxic and apoptosis-inducing effect of ent-15-oxo-kaur-16-en-19-oic acid, a derivative of grandiflorolic acid from Espeletia schultzii. Phytochemistry 69, 432-438.
Yigang, H., Qianhao, Y., Junhui, Y., Daoyu, Z., Pei, L., Hongping, Y., Youshui, G., Changqing, Z., Yixuan, C., 2020. Chrysophanic acid shifts the differentiation tendency of BMSCs to prevent alcohol-induced osteonecrosis of the femoral head. Cell Prolif. 1-12. doi: 10.1111/cpr.12871.
