Antiradical, antibacterial activities and in silico molecular docking of ethyl-β-D-fructofuranoside from hydro-ethanolic crude extract of Erythrina excelsa stem bark - 2025
Antiradical, antibacterial activities and in silico molecular docking of ethyl-β-D-fructofuranoside from hydro-ethanolic crude extract of Erythrina excelsa stem bark
Yaya, Joël Abel Gbaweng; Nyemb, Jean Noël; Olboungou, Nelson Mandelaet al.
[en] The aim of the present study was to isolate and characterize compounds responsible of the antiradical and antibacterial activities in the hydro-ethanolic crude extract of Erythrina excelsa stem bark. Chemical investigation of this polar extract resulted in the isolation of a fructose derivative identified as ethyl-β-D-fructofuranoside (3) and an alkaloid designated L-(+)-Abrine (4); two compounds isolated here for the first time from the genus Erythrina, along with a mixture of sitosterol 3-O-β-D-glucopyranoside (2) and stigmasterol 3-O-β-D-glucopyranoside (1). Their structures were determined using spectroscopic methods (IR, 1 & 2D NMR) as well as HR-ESI-MS and literature data. The hydro-ethanolic extract and compound 3 were tested for antibacterial activity on Escherichia coli, Salmonella typhi, Salmonella typhimurium and Salmonella enterica, and for antioxidant activity using free radical scavenging (DPPH) and Ferric Reducing Ability Power (FRAP). Compound 3 showed good antiradical potential (IC50 21.11 ± 0.53 μg/mL) and moderate antibacterial activity against all the tested bacteria with MIC of 200 μg/mL. For the FRAP method, hydro-ethanolic extract showed weak activity with value of 425 mg GAE/g, while Ethyl-β-D-fructofuranoside (3) exhibited a very good reducing power (40 mg GAE/g). Ethyl-β-D-fructofuranoside (3) could, therefore, be responsible for the antiradical activity of the hydro-ethanolic crude extract.
Disciplines :
Pharmacy, pharmacology & toxicology
Author, co-author :
Yaya, Joël Abel Gbaweng ; Department of Chemistry, Faculty of Science, University of Ngaoundere, Ngaoundere, Cameroon ; Centre for Research on Medicinal Plants and Traditional Medicine, Institute of Medical Research and Medicinal Plants Studies, Yaounde, Cameroon
Nyemb, Jean Noël ; Department of Refining and Petrochemistry, National Advanced School of Mines and Petroleum Industries, The University of Maroua, Kaele, Cameroon
Olboungou, Nelson Mandela; Department of Chemistry, Faculty of Science, University of Ngaoundere, Ngaoundere, Cameroon
Abdou, Jean Pierre ; Department of Chemistry, Faculty of Science, University of Ngaoundere, Ngaoundere, Cameroon ; Centre for Research on Medicinal Plants and Traditional Medicine, Institute of Medical Research and Medicinal Plants Studies, Yaounde, Cameroon
Ketsemen, Herve Landry ; Department of Organic Chemistry, Faculty of Science, Univesrsity of Yaounde 1, Yaounde, Cameroon
Kopa, Théodora Kowa ; Centre for Research on Medicinal Plants and Traditional Medicine, Institute of Medical Research and Medicinal Plants Studies, Yaounde, Cameroon
Toukam, Paul Djouonzo ; Centre for Research on Medicinal Plants and Traditional Medicine, Institute of Medical Research and Medicinal Plants Studies, Yaounde, Cameroon
Frederich, Michel ; Université de Liège - ULiège > Département de pharmacie > Pharmacognosie ; Université de Liège - ULiège > Unités de recherche interfacultaires > Centre Interdisciplinaire de Recherche sur le Médicament (CIRM)
Talla, Emmanuel ; Department of Chemistry, Faculty of Science, University of Ngaoundere, Ngaoundere, Cameroon
Language :
English
Title :
Antiradical, antibacterial activities and in silico molecular docking of ethyl-β-D-fructofuranoside from hydro-ethanolic crude extract of Erythrina excelsa stem bark
Abdou JP, Nyemb JN, Momeni J, Fadimatou A, Gbaweng AJY, Tsopmejio JP, Fawa G, Choudhary MI., 2022. A new cytotoxic ceramide from Dalbergia boehmii Taub. stem bark. Pharmacogn Res. 14(4):442–445. doi: 10.5530/pres.14.4.64.
Ahmad B, Naz S, Azam S, Khan I, Bashir S, Hassan F., 2015. Antimicrobial, phytotoxic, heamagglutination, insecticidal and antioxidant activities of the fruits of Sarcococca saligna (D. Don) Muel. Pak J Bot. 47:313–319.
Benzie IFF, Strain JJ., 1996. The ferric reducing ability of plasma (FRAP) as a measure of antioxidant power: the FRAP assay. Anal Biochem. 239(1):70–76. doi: 10.1006/abio.1996.0292.
Blois MS., 1958. Antioxidant determinations by the use of a stable free radical. Nature. 181(4617):1199–1200. doi: 10.1038/1811199a0.
Chew YL, Goh JK, Lim YY., 2009. Assessment of in vitro antioxidant capacity and polyphenolic composition of selected medicinal herbs from Leguminosae family in Peninsular Malaysia. Food Chem. 116(1):13–18. doi: 10.1016/j.foodchem.2009.01.091.
Clinical Laboratory Standard Institute (CLSI). 2008. Reference methods for dilution antimicrobial susceptibility tests for bacteria that grow aerobically: approved standard. 7th ed. Wayne (PA): Clinical Laboratory Standard Institute.
De Luca A, Sibilio G, de Luca P, del Guacchio E., 2018. DNA barcoding to confirm the morphological identification of the coral trees (Erythrina spp., Fabaceae) in the ancient gardens of Naples (Campania, Italy). Plants. 7(2):43. doi: 10.3390/plants7020043.
Finkel T, Holbrook NJ., 2000. Oxidants, oxidative stress and the biology of ageing. Nature. 408(6809):239–247. doi: 10.1038/35041687.
Hickey M, King C., 1981. One hundred families of flowering plants. Cambridge (UK): Cambridge University Press.
Jiofack T, Fokunang C, Guedje N, Kemeuze V, Fongnzossie E, Nkongmeneck BA, Mapongmetsem PM, Tsabang N., 2010. Ethnobotanical uses of medicinal plants of two ethnoecological regions of Cameroon. Int J Med Med Sci. 2:60–79.
Kuete V, Sandjo LP, Kwamou GM, Wiench B, Nkengfack AE, Efferth T., 2014. Activity of three cytotoxic isoflavonoids from Erythrina excelsa and Erythrina senegalensis (neobavaisoflavone, sigmoidin H and isoneorautenol) toward multi-factorial drug resistant cancer cells. Phytomedicine. 21(5):682–688. doi: 10.1016/j.phymed.2013.10.017.
Kwamou GMN, Sandjo LP, Kuete V, Wandja AAK, Tankeo SB, Efferth T, Augustin E, Nkengfack AE., 2015. Unprecedented new nonadecyl para-hydroperoxycinnamate isolated from Erythrina excelsa and its cytotoxic activity. Nat Prod Res. 29(10):921–925. doi: 10.1080/14786419.2014.959519.
Li H, Cheng K, Wong C, Fan K, Chen F, Jiang Y., 2007. Evaluation of antioxidant capacity and total phenolic content of different fractions of selected microalgae. Food Chem. 102(3):771–776. doi: 10.1016/j.foodchem.2006.06.022.
Lunga PK, Qin XJ, Yang XW, Kuiate JR, Du ZZ, Gatsing D., 2014. Antimicrobial steroidal saponin and oleanane-type triterpenoid saponins from Paullinia pinnata. BMC Complement Altern Med. 14(1):369. doi: 10.1186/1472-6882-14-369.
Majinda RTR, Cornelius CWW, Bernard FJ., 2005. Bioactive non-alkaloidal constituents from the genus Erythrina. Nat Prod Chem. 32:821–853. doi: 10.1016/S1572-5995(05)80070-5.
Matcheme M, Dabolé B, Moussa D, Nyemb JN, Talla E, Laurent S, Henoumont C, Venditti A., 2025. Chemical constituents from Cordia myxa L. (Boraginaceae) and their antibacterial activity. Nat Prod Res. 39(4):725–733. doi: 10.1080/14786419.2023.2288928.
Ngueu ST, Tchoumtchoua J, Njamen D, Halabalaki M, Laudenbach-Leschowski U, Diel P., 2016. Erythrina excelsa exhibits estrogenic effects in vivo and in vitro and is cytotoxic on breast and colon cancer cell lines. Pharm Biol. 54(5):835–844. doi: 10.3109/13880209.2015.1087037.
Niu Y, Wang B, Zhou L, Ma C, Waterhouse GIN, Liu Z, Ahmed AF, Sun-Waterhouse D, Kang W., 2021. Nigella sativa: a dietary supplement as an immune-modulator on the basis of bioactive components. Front Nutr. 8:722813. doi: 10.3389/fnut.2021.722813.
Nyemb JN, Djankou MT, Talla E, Tchinda AT, Ngoudjou DT, Iqbal J, Mbafor JT., 2018. Antimicrobial, α-Glucosidase and alkaline phosphatase inhibitory activities of bergenin, the major constituent of Cissus populnea roots. Med Chem. 08(02):426–430. doi: 10.4172/2161-0444.1000492.
Ogutu AI, Lilechi DB, Mutai C, Bii C., 2012. Phytochemical analysis and antimicrobial activity of Phytolacca dodecandra, Cucumis aculeatus and Erythrina excelsa. Int J Biol Chem Sci. 6(2):692–704.
Ombuna NM, Machocho AK, Ng’ang’a MM, Keru GK, Wanyonyi AW, Amuka O., 2016. Stem bark extracts of Erythrina excelsa (Bark) and their activities. J Med Plants Res. 10:686–694. doi: 10.5897/JMPR2016.6070.
Pillay CC, Jäger AK, Mulholland DA, van Staden J., 2001. Cyclooxygenase inhibiting and antibacterial activities of South African Erythrina species. J Ethnopharmacol. 74(3):231–237. doi: 10.1016/s0378-8741(00)00366-4.
Rudolph CJ, Yingtao Z, Ram J, Sharon WL, Shannon F, Pat S, John RB., 2009. Quantification of L-abrine in human and rat urine: a biomarker for toxin abrin. J Anal Toxicol. 33(2):77–84. doi: 10.1093/jat/33.2.77.
Samy RP, Thwin MM, Gopalakrishnakone P, Ignacimuthu S., 2008. Ethnobotanical survey of folk plants for the treatment of snakebites in southern part of Tamil Nadu. India J Ethnopharmacol. 115(2):302–312. doi: 10.1016/j.jep.2007.10.006.
Shaker S, Run-Zhu F, Hou-Jin L, Wen-Jian L., 2021. A pair of novel bisindole alkaloid enantiomers from marine fungus Fusarium sp. XBB-9. Nat Prod Res. 35(9):1497–1503. doi: 10.1080/14786419.2019.1655416.
Talla E, Nyemb J, Tiabou A, Djou S, Biyanzi P, Sophie L, Elst L, Tanyi J., 2016. Antioxidant activity and a new ursane-type triterpene from Vitellaria paradoxa (Sapotaceae) stem barks. EJMP. 16(3):1–20. doi: 10.9734/EJMP/2016/28847.
Tirado JO, Flores F, Maldonado S, Mihae R, Naranjo B, Muñoz D, Manjunatha B, Selvanayagam M, Rajeswari B., 2017. Molecular characterization and antioxidant potential of Andean chlorophytes from Ecuador. J Appl Pharm Sci. 7:56–60.
Tueche AB, Zingue S, Tchoupang EN, Gueyo TN, Gbaweng Yaya AJ, Njuh AN, Ntsa DM, Njamen D., 2018. Abyssinone V-4’-methyl ether isolated from Erythrina droogmansiana (Leguminosae) inhibits cell growth and mammary glands hyperplasia induced in Swiss mice by the 7,12-dimethylbenz(a)anthracene. Evid Based Complement Alternat Med. 2018(1):7959068. doi: 10.1155/2018/7959068.
Usha PTA, Jose S, Nisha AR., 2010. Antimicrobial drug resistance. A global concern. Veter W. 3(3):138–139.
Yaya GAJ, Hadidjatou D, Zingué S, Talla E, Tchinda TA, Frédérich M, Mbafor JT., 2020. Excelsanone, a new isoflavonoid from Erythrina excelsa (Fabaceae), with in vitro antioxidant and in vitro cytotoxic effects on prostate cancer cells lines. Nat Prod Res. 34(5):659–667. doi: 10.1080/14786419.2018.1495639.
