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Singh A, Mazumder A, Das S, Kanda A. Preparation, In Vivo and Molecular Docking Study of Nano-Emulsion Obtained From the Isolated Phytoconstituents of Symplocos racemosa for Mitigating Depression. Chem Biodivers 2025:e202500262. [PMID: 40079725 DOI: 10.1002/cbdv.202500262] [Citation(s) in RCA: 0] [Impact Index Per Article: 0] [Reference Citation Analysis] [Abstract] [Key Words] [Track Full Text] [Journal Information] [Subscribe] [Scholar Register] [Received: 01/21/2025] [Revised: 03/04/2025] [Accepted: 03/13/2025] [Indexed: 03/15/2025]
Abstract
Depression is a prevalent, chronic, and debilitating disorder characterized by high treatment resistance. Symplocos racemosa, containing phenols and triterpenoids, acts as an antidepressant by elevating brain monoamine levels. This study aimed to enhance the targeted delivery of S. racemosa via nano-emulsion and improve its therapeutic efficacy against depression. In addition, it sought to elucidate the molecular mechanisms underlying its effects through molecular docking studies. S. racemosa bark was extracted using methanol and ethyl acetate, yielding six phytoconstituents (ellagic acid, betulinic acid, acetyl oleanolic acid, salireposide, oleanolic acid, and symlocoside) through column chromatography. Molecular docking against MAO-A was performed to confirm significant binding affinity. A chitosan-loaded herbal nano-emulsion containing these phytoconstituents was formulated for enhanced brain delivery tested using animal studies using forced swim test (FST) and actophotometer models. Docking studies confirmed that all the components exhibit a good binding toward MAO-A, comparable to standard moclobemide, and among all salireposide has the most significant and better binding affinity, higher than moclobemide. Nano-emulsion, at both dosages, reduced the immobility time in the FST and increased the locomotor activity in the actophotometer of depressed mice. Nano-emulsion of isolated phytoconstituents from S. racemosa exhibited synergistic effects, effectively managing depression by inhibiting MAO-A.
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Affiliation(s)
- Archna Singh
- Department of Pharmacology, Noida Institute of Engineering and Technology (Pharmacy Institute), Greater Noida, Uttar Pradesh, India
| | - Avijit Mazumder
- Department of Pharmacology, Noida Institute of Engineering and Technology (Pharmacy Institute), Greater Noida, Uttar Pradesh, India
| | - Saumya Das
- Department of Pharmacology, Noida Institute of Engineering and Technology (Pharmacy Institute), Greater Noida, Uttar Pradesh, India
| | - Anmol Kanda
- Department of Pharmacology, Noida Institute of Engineering and Technology (Pharmacy Institute), Greater Noida, Uttar Pradesh, India
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Kepawou MG, Nguemdjo Chimeze VW, Kamdem MHK, Ambamba Akamba BD, Melogmo YKD, Nkoumou AH, Wakeu BNK, Talla RM, Foudjo Melacheu GL, Mpho Mmutlane E, Ndinteh DT, Mbazoa CD, Wandji J. Antibacterial activities of phytochemical constituents from the leaves of Coula edulis (Olacaceae) and In silico investigations of ursolic acid. Nat Prod Res 2025:1-7. [PMID: 39883100 DOI: 10.1080/14786419.2025.2458671] [Citation(s) in RCA: 0] [Impact Index Per Article: 0] [Reference Citation Analysis] [Abstract] [Key Words] [Track Full Text] [Journal Information] [Subscribe] [Scholar Register] [Received: 06/29/2024] [Revised: 01/17/2025] [Accepted: 01/22/2025] [Indexed: 01/31/2025]
Abstract
From the leaves of Coula edulis, fourteen compounds were isolated and identified: D-mannitol (1), a mixture of β-sitosterol (2) and stigmasterol (3), α-amyrin (4), betulin (5), lupeol (6), lupenone (7), betulinic acid (8), taraxerol (9), 3β-(E)-coumaroyltaraxerol (10), 3β-(Z)-coumaroyltaraxerol (11), ursolic acid (12), stigmasterol 3-O-β-D-glucoside (13), and β-sitosterol 3-O-β-D-glucoside (14). These compounds were analysed through NMR spectroscopy (both 1D and 2D) and by comparing them to previously published data. Compounds 1, 4, 5, and 7-9 have been identified from this species for the first time. Antibacterial activity was assessed, with compound 12 displaying the best efficacy against Staphylococcus aureus (MIC: 15.6 μg/mL). Molecular docking of compound 12 led to twenty lead compounds, among which 12 F displayed the highest score (-10.1 kcal/mol). Most lead compounds showed better scores compared to Vancomycin (-8.8 kcal/mol). Biovia Discovery Studio analysis reveals lead compounds interacting with CASTp-predicted active pocket amino acids.
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Affiliation(s)
- Manuela Guaelle Kepawou
- Laboratory of Natural Products and Heterocyclic Synthesis, Department of Organic Chemistry, Faculty of Sciences, The University of Yaoundé 1, Yaoundé, Cameroon
- Drug Discovery and Smart Molecules Research Laboratory, Department of Chemical Sciences, University of Johannesburg, Doornfontein, Johannesburg, South Africa
- Center for Natural Product Research (CNPR), Chemical Sciences Department, University of Johannesburg, Doornfontein, Johannesburg, South Africa
| | - Valery Wilfried Nguemdjo Chimeze
- Laboratory of Natural Products and Heterocyclic Synthesis, Department of Organic Chemistry, Faculty of Sciences, The University of Yaoundé 1, Yaoundé, Cameroon
| | - Michael Hermann Kengne Kamdem
- Drug Discovery and Smart Molecules Research Laboratory, Department of Chemical Sciences, University of Johannesburg, Doornfontein, Johannesburg, South Africa
- Center for Natural Product Research (CNPR), Chemical Sciences Department, University of Johannesburg, Doornfontein, Johannesburg, South Africa
- Research Center for Synthesis and catalysis; Department of Chemical Sciences, University of Johannesburg-Kingsway Campus, Auckland Park, South Africa
| | | | | | - Adolph Hugues Nkoumou
- Laboratory of Natural Products and Heterocyclic Synthesis, Department of Organic Chemistry, Faculty of Sciences, The University of Yaoundé 1, Yaoundé, Cameroon
| | - Brussine Nadège Kweka Wakeu
- Laboratory of Natural Products and Heterocyclic Synthesis, Department of Organic Chemistry, Faculty of Sciences, The University of Yaoundé 1, Yaoundé, Cameroon
| | - Rostan Mangoua Talla
- Laboratory of Natural Products and Heterocyclic Synthesis, Department of Organic Chemistry, Faculty of Sciences, The University of Yaoundé 1, Yaoundé, Cameroon
| | - Gertrude Laura Foudjo Melacheu
- Laboratory of Natural Products and Heterocyclic Synthesis, Department of Organic Chemistry, Faculty of Sciences, The University of Yaoundé 1, Yaoundé, Cameroon
| | - Edwin Mpho Mmutlane
- Center for Natural Product Research (CNPR), Chemical Sciences Department, University of Johannesburg, Doornfontein, Johannesburg, South Africa
| | - Derek Tantoh Ndinteh
- Center for Natural Product Research (CNPR), Chemical Sciences Department, University of Johannesburg, Doornfontein, Johannesburg, South Africa
- Research Center for Synthesis and catalysis; Department of Chemical Sciences, University of Johannesburg-Kingsway Campus, Auckland Park, South Africa
| | - Céline Djama Mbazoa
- Laboratory of Natural Products and Heterocyclic Synthesis, Department of Organic Chemistry, Faculty of Sciences, The University of Yaoundé 1, Yaoundé, Cameroon
| | - Jean Wandji
- Laboratory of Natural Products and Heterocyclic Synthesis, Department of Organic Chemistry, Faculty of Sciences, The University of Yaoundé 1, Yaoundé, Cameroon
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Wawoczny A, Gillner D. The Most Potent Natural Pharmaceuticals, Cosmetics, and Food Ingredients Isolated from Plants with Deep Eutectic Solvents. JOURNAL OF AGRICULTURAL AND FOOD CHEMISTRY 2023. [PMID: 37433265 PMCID: PMC10375538 DOI: 10.1021/acs.jafc.3c01656] [Citation(s) in RCA: 11] [Impact Index Per Article: 5.5] [Reference Citation Analysis] [Abstract] [Key Words] [Track Full Text] [Subscribe] [Scholar Register] [Indexed: 07/13/2023]
Abstract
There is growing interest in reducing the number of synthetic products or additives and replacing them with natural ones. The pharmaceutical, cosmetic, and food industries are especially focused on natural and bioactive chemicals isolated from plants or microorganisms. The main challenge here is to develop efficient and ecological methods for their isolation. According to the strategies and rules of sustainable development and green chemistry, green solvents and environmentally friendly technologies must be used. The application of deep eutectic solvents as efficient and biodegradable solvents seems to be a promising alternative to traditional methods. They are classified as being green and ecological but, most importantly, very efficient extraction media compared to organic solvents. The aim of this review is to present the recent findings on green extraction, as well as the biological activities and the possible applications of natural plant ingredients, namely, phenolics, flavonoids, terpenes, saponins, and some others. This paper thoroughly reviews modern, ecological, and efficient extraction methods with the use of deep eutectic solvents (DESs). The newest findings, as well as the factors influencing the efficiency of extraction, such as water content, and hydrogen bond donor and acceptor types, as well as the extraction systems, are also discussed. New solutions to the major problem of separating DESs from the extract and for solvent recycling are also presented.
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Affiliation(s)
- Agata Wawoczny
- Department of Organic Chemistry, Bioorganic Chemistry and Biotechnology, Faculty of Chemistry, Silesian University of Technology, 44-100 Gliwice, Poland
- Biotechnology Centre, Silesian University of Technology, 44-100 Gliwice, Poland
| | - Danuta Gillner
- Department of Organic Chemistry, Bioorganic Chemistry and Biotechnology, Faculty of Chemistry, Silesian University of Technology, 44-100 Gliwice, Poland
- Biotechnology Centre, Silesian University of Technology, 44-100 Gliwice, Poland
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Mouzié CM, Guefack MGF, Kianfé BY, Serondo HU, Ponou BK, Siwe-Noundou X, Teponno RB, Krause RWM, Kuete V, Tapondjou LA. A New Chalcone and Antimicrobial Chemical Constituents of Dracaena stedneuri. Pharmaceuticals (Basel) 2022; 15:725. [PMID: 35745644 PMCID: PMC9228254 DOI: 10.3390/ph15060725] [Citation(s) in RCA: 5] [Impact Index Per Article: 1.7] [Reference Citation Analysis] [Abstract] [Key Words] [Grants] [Track Full Text] [Download PDF] [Figures] [Journal Information] [Subscribe] [Scholar Register] [Received: 03/04/2022] [Revised: 04/08/2022] [Accepted: 04/10/2022] [Indexed: 02/01/2023] Open
Abstract
Microbial infections are leading causes of death and morbidity all over the world due to the development of the resistance to antibiotics by certain microorganisms. In this study, the chemical exploration of the ethanol (EtOH) extract of the aerial part of Dracaena stedneuri (Dracaenaceae) led to the isolation of one previously unreported chalcone derivative, i.e., 2',4'-dihydroxy-2,3'-dimethoxychalcone (1), together with 12 known compounds: 8-(C)-methylquercetagetin-3,6,3'-trimethyl ether (2), methylgalangine (3), quercetin (4), kaempferol (5), 6,8-dimethylchrysin (6), ombuine-3-O-rutinoside (4',7-dimethylquercetin-3-O-α-L-rhamnopyranosyl-(1 → 6) -β-D-glucopyranoside) (7), alliospiroside A (8), β-sitosterol 3-O-glucopyranoside (9), ishigoside (10), betulinic acid (11), oleanolic acid (12), and lupeol (13). The structures were determined by spectroscopic and spectrometric analysis including 1- and 2-Dimensional Nuclear Magnetic Resonance (1D- and 2D-NMR), High-Resolution Electrospray Ionization Mass Spectrometry (HRESIMS), and comparison with literature data. The isolated secondary metabolites and crude extract displayed antibacterial activity against some multidrug-resistant strains with minimal inhibitory concentration (MIC) values ranging from 32 to 256 μg/mL. The antibacterial activity of compound 13 against Enterobacter aerogenes ATCC13048 (MIC value: 32 μg/mL) was higher than that of chloramphenicol used as the reference drug (MIC = 64 μg/mL).
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Affiliation(s)
- Cédric M. Mouzié
- Department of Chemistry, Faculty of Science, University of Dschang, Dschang P.O. Box 67, Cameroon; (C.M.M.); (B.Y.K.); (H.U.S.); (B.K.P.); (L.A.T.)
| | - Michel-Gael F. Guefack
- Department of Biochemistry, Faculty of Science, University of Dschang, Dschang P.O. Box 67, Cameroon; (M.-G.F.G.); (V.K.)
| | - Boris Y. Kianfé
- Department of Chemistry, Faculty of Science, University of Dschang, Dschang P.O. Box 67, Cameroon; (C.M.M.); (B.Y.K.); (H.U.S.); (B.K.P.); (L.A.T.)
| | - Héritier U. Serondo
- Department of Chemistry, Faculty of Science, University of Dschang, Dschang P.O. Box 67, Cameroon; (C.M.M.); (B.Y.K.); (H.U.S.); (B.K.P.); (L.A.T.)
- Higher Pedagogical Institute of Bukavu, Bukavu P.O. Box 854, Democratic Republic of the Congo
| | - Beaudelaire K. Ponou
- Department of Chemistry, Faculty of Science, University of Dschang, Dschang P.O. Box 67, Cameroon; (C.M.M.); (B.Y.K.); (H.U.S.); (B.K.P.); (L.A.T.)
| | - Xavier Siwe-Noundou
- Pharmaceutical Sciences Department, School of Pharmacy, Sefako Makgatho Health Sciences University, Pretoria 0204, South Africa
| | - Rémy B. Teponno
- Department of Chemistry, Faculty of Science, University of Dschang, Dschang P.O. Box 67, Cameroon; (C.M.M.); (B.Y.K.); (H.U.S.); (B.K.P.); (L.A.T.)
| | - Rui W. M. Krause
- Department of Chemistry, Faculty of Science, Rhodes University, Gahamstown 6139, South Africa;
| | - Victor Kuete
- Department of Biochemistry, Faculty of Science, University of Dschang, Dschang P.O. Box 67, Cameroon; (M.-G.F.G.); (V.K.)
| | - Léon A. Tapondjou
- Department of Chemistry, Faculty of Science, University of Dschang, Dschang P.O. Box 67, Cameroon; (C.M.M.); (B.Y.K.); (H.U.S.); (B.K.P.); (L.A.T.)
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Olanlokun JO, Okoro PO, Olorunsogo OO. The roles of betulinic acid on circulating concentrations of creatine kinase and immunomodulation in mice infected with chloroquine-susceptible and resistant strains of Plasmodium berghei. J Parasit Dis 2022; 46:124-132. [PMID: 35299933 PMCID: PMC8901915 DOI: 10.1007/s12639-021-01407-9] [Citation(s) in RCA: 2] [Impact Index Per Article: 0.7] [Reference Citation Analysis] [Abstract] [Key Words] [Track Full Text] [Journal Information] [Subscribe] [Scholar Register] [Received: 02/03/2021] [Accepted: 05/24/2021] [Indexed: 01/08/2023] Open
Abstract
Complete malarial therapy depends largely on the immunological and inflammatory response of the host to the invading potentials of malarial parasite. In this study, we evaluated the roles of betulinic acid on immunological response, anti-inflammatory potentials, cardiac and skeletal muscle tissue damage in mice infected with chloroquine susceptible (NK 65) and resistant (ANKA) strains of Plasmodium berghei. Serum Interleukins 1β and 6 (IL-1β, IL-6), tumour necrosis factor alpha (TNF-α), immunoglobulins G and M (IgG and IgM), C-reactive protein (CRP) and creatine kinase (CK) were determined using ELISA technique. Aspartate aminotransferase (AST), alanine aminotransferase (ALT) and gamma glutammyl transferase (GGT) were determined using ELISA technique. The results showed that betulinic acid decreased the levels of IL-1β, IL-6, TNF-α and CRP relative to the infected control. The IgG and IgM levels significantly increased in both models while CK did not decrease significantly in both models although serum AST, ALT and GGT significantly decreased compared to the infected control. These results showed that betulinic acid possessed anti-inflammatory, immunomodulatory and remediating effects on tissue damage. Furthermore, the decrease in activity of CK brought about by betulinic acid is indicative of decrease in cardiac and skeletal muscle injury which is a major pathological concern in Plasmodium infection and treatment.
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Affiliation(s)
- John Oludele Olanlokun
- Laboratories for Biomembrane Research and Biotechnology, Department of Biochemistry, University of Ibadan, Ibadan, Nigeria
| | - Praise Oghenegare Okoro
- Laboratories for Biomembrane Research and Biotechnology, Department of Biochemistry, University of Ibadan, Ibadan, Nigeria
| | - Olufunso Olabode Olorunsogo
- Laboratories for Biomembrane Research and Biotechnology, Department of Biochemistry, University of Ibadan, Ibadan, Nigeria
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Olanlokun JO, Okoro PO, Lawal OS, Bodede O, Olotu F, Idowu TO, Prinsloo G, Soliman ME, Olorunsogo OO. Betulinic acid purified from Alstonia boonei inhibits folate biosynthesis in malarial Plasmodium, enhances mitochondrial pore opening and F1F0 ATPase in mice. J Mol Struct 2021. [DOI: 10.1016/j.molstruc.2021.130454] [Citation(s) in RCA: 0] [Impact Index Per Article: 0] [Reference Citation Analysis] [Track Full Text] [Journal Information] [Subscribe] [Scholar Register] [Indexed: 10/21/2022]
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Omara T, Kiprop AK, Kosgei VJ. Albizia coriaria Welw ex Oliver: a review of its ethnobotany, phytochemistry and ethnopharmacology. ADVANCES IN TRADITIONAL MEDICINE 2021. [DOI: 10.1007/s13596-021-00600-8] [Citation(s) in RCA: 5] [Impact Index Per Article: 1.3] [Reference Citation Analysis] [Track Full Text] [Journal Information] [Subscribe] [Scholar Register] [Indexed: 01/24/2023]
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