Isolation, Structure Elucidation and Antimicrobial Evaluation of Natural Pentacyclic Triterpenoids and Phytochemical Investigation of Different Fractions of <i>Ziziphus spina-christi</i> (L.) Stem Bark Using LCHRMS Analysis
<i>Ziziphus spina-christi</i> L. (ZSC-L) is a tree with thorny branches, belongs to the family Rhamnaceae and grows in the sub-tropics. The purpose of this research is to isolate and partially purify bioactive components from the crude ethanol extract of the stem bark of ZSC-L. Besides,...
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MDPI AG
2022-03-01
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| author | Essam N. Ads Syed I. Hassan Saravanan Rajendrasozhan Mona H. Hetta Shaza H. Aly Mohamed A. Ali |
| author_facet | Essam N. Ads Syed I. Hassan Saravanan Rajendrasozhan Mona H. Hetta Shaza H. Aly Mohamed A. Ali |
| author_sort | Essam N. Ads |
| collection | DOAJ |
| description | <i>Ziziphus spina-christi</i> L. (ZSC-L) is a tree with thorny branches, belongs to the family Rhamnaceae and grows in the sub-tropics. The purpose of this research is to isolate and partially purify bioactive components from the crude ethanol extract of the stem bark of ZSC-L. Besides, bioassay-guided fractionation of ZSC-L stem bark was conducted using different solvents. The solvents were reutilized to minimize the production cost and environmental harm. In addition, the antimicrobial activities of the fractions were analyzed, followed by metabolic profiling using LC-HRMS. The <i>n</i>-butanol fraction showed the highest antimicrobial efficacy, so it was subjected to further purification. For the first time, two major compounds were isolated from the stem bark of ZSC-L and identified as lupane-type pentacyclic triterpenoids betulinic acid and betulin. Both compounds were used as antibacterial and anticancer agents and considered as a green product as the extraction procedure reduced the use of hazardous chemicals. Metabolic characterization of ZSC-L and its bioactive fractions were performed using LC-HR-ESI-MS and the results revealed the dereplication of 36 compounds belonging to different chemical classes. Flavonoids and triterpenes were the most prominent metabolite classes in the different fractions. The molecular docking results were obtained by studying the interaction of betulin and betulinic acid with antimicrobial receptors (4UYM, 1IYL, 1AJ2, 6J7L, 1AD4, 2VEG) to support the in vitro results. Our study highlights that <i>Ziziphus spina-christi</i> and its phytoconstituents, especially triterpenoids, act as a promising antimicrobial candidate in pharmaceutical and clinical applications. |
| first_indexed | 2024-03-09T13:11:44Z |
| format | Article |
| id | doaj.art-88fdae6b73574e4285f8b020fd00d01c |
| institution | Directory Open Access Journal |
| issn | 1420-3049 |
| language | English |
| last_indexed | 2024-03-09T13:11:44Z |
| publishDate | 2022-03-01 |
| publisher | MDPI AG |
| record_format | Article |
| series | Molecules |
| spelling | doaj.art-88fdae6b73574e4285f8b020fd00d01c2023-11-30T21:41:26ZengMDPI AGMolecules1420-30492022-03-01276180510.3390/molecules27061805Isolation, Structure Elucidation and Antimicrobial Evaluation of Natural Pentacyclic Triterpenoids and Phytochemical Investigation of Different Fractions of <i>Ziziphus spina-christi</i> (L.) Stem Bark Using LCHRMS AnalysisEssam N. Ads0Syed I. Hassan1Saravanan Rajendrasozhan2Mona H. Hetta3Shaza H. Aly4Mohamed A. Ali5Department of Chemistry, Faculty of Science, Zagazig University, Zagazig 44519, EgyptDepartment of Chemistry, College of Science, Sultan Qaboos University, P.O. Box 50, Muscat P.C. 123, OmanDepartment of Chemistry, College of Sciences, University of Ha’il, Ha’il 55476, Saudi ArabiaDepartment of Pharmacognosy, Faculty of Pharmacy, Fayoum University, Fayoum 63514, EgyptDepartment of Pharmacognosy, Faculty of Pharmacy, Badr University in Cairo (BUC), Badr City 11829, EgyptSchool of Biotechnology, Badr University in Cairo (BUC), Badr City 11829, Egypt<i>Ziziphus spina-christi</i> L. (ZSC-L) is a tree with thorny branches, belongs to the family Rhamnaceae and grows in the sub-tropics. The purpose of this research is to isolate and partially purify bioactive components from the crude ethanol extract of the stem bark of ZSC-L. Besides, bioassay-guided fractionation of ZSC-L stem bark was conducted using different solvents. The solvents were reutilized to minimize the production cost and environmental harm. In addition, the antimicrobial activities of the fractions were analyzed, followed by metabolic profiling using LC-HRMS. The <i>n</i>-butanol fraction showed the highest antimicrobial efficacy, so it was subjected to further purification. For the first time, two major compounds were isolated from the stem bark of ZSC-L and identified as lupane-type pentacyclic triterpenoids betulinic acid and betulin. Both compounds were used as antibacterial and anticancer agents and considered as a green product as the extraction procedure reduced the use of hazardous chemicals. Metabolic characterization of ZSC-L and its bioactive fractions were performed using LC-HR-ESI-MS and the results revealed the dereplication of 36 compounds belonging to different chemical classes. Flavonoids and triterpenes were the most prominent metabolite classes in the different fractions. The molecular docking results were obtained by studying the interaction of betulin and betulinic acid with antimicrobial receptors (4UYM, 1IYL, 1AJ2, 6J7L, 1AD4, 2VEG) to support the in vitro results. Our study highlights that <i>Ziziphus spina-christi</i> and its phytoconstituents, especially triterpenoids, act as a promising antimicrobial candidate in pharmaceutical and clinical applications.https://www.mdpi.com/1420-3049/27/6/1805antimicrobial activitybutanol extractbetulinbetulinic acidLC-HRMSmolecular docking |
| spellingShingle | Essam N. Ads Syed I. Hassan Saravanan Rajendrasozhan Mona H. Hetta Shaza H. Aly Mohamed A. Ali Isolation, Structure Elucidation and Antimicrobial Evaluation of Natural Pentacyclic Triterpenoids and Phytochemical Investigation of Different Fractions of <i>Ziziphus spina-christi</i> (L.) Stem Bark Using LCHRMS Analysis Molecules antimicrobial activity butanol extract betulin betulinic acid LC-HRMS molecular docking |
| title | Isolation, Structure Elucidation and Antimicrobial Evaluation of Natural Pentacyclic Triterpenoids and Phytochemical Investigation of Different Fractions of <i>Ziziphus spina-christi</i> (L.) Stem Bark Using LCHRMS Analysis |
| title_full | Isolation, Structure Elucidation and Antimicrobial Evaluation of Natural Pentacyclic Triterpenoids and Phytochemical Investigation of Different Fractions of <i>Ziziphus spina-christi</i> (L.) Stem Bark Using LCHRMS Analysis |
| title_fullStr | Isolation, Structure Elucidation and Antimicrobial Evaluation of Natural Pentacyclic Triterpenoids and Phytochemical Investigation of Different Fractions of <i>Ziziphus spina-christi</i> (L.) Stem Bark Using LCHRMS Analysis |
| title_full_unstemmed | Isolation, Structure Elucidation and Antimicrobial Evaluation of Natural Pentacyclic Triterpenoids and Phytochemical Investigation of Different Fractions of <i>Ziziphus spina-christi</i> (L.) Stem Bark Using LCHRMS Analysis |
| title_short | Isolation, Structure Elucidation and Antimicrobial Evaluation of Natural Pentacyclic Triterpenoids and Phytochemical Investigation of Different Fractions of <i>Ziziphus spina-christi</i> (L.) Stem Bark Using LCHRMS Analysis |
| title_sort | isolation structure elucidation and antimicrobial evaluation of natural pentacyclic triterpenoids and phytochemical investigation of different fractions of i ziziphus spina christi i l stem bark using lchrms analysis |
| topic | antimicrobial activity butanol extract betulin betulinic acid LC-HRMS molecular docking |
| url | https://www.mdpi.com/1420-3049/27/6/1805 |
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