GC-MS analysis of bioactive compounds in ethanolic extract on different parts of Ziziphus mauritiana

##plugins.themes.bootstrap3.article.main##

LARBENNO PAULOI
RAFIDAH MD SALIM
LIEW KANG CHIANG
MURNI SUNDANG
NOR AZIZUN RUSDI
MANDY MAID
SHIRLEY MARYLINDA BAKANSING
JANSHAH MOKTAR

Abstract

Abstract. Pauloi L, Salmim RM, Chiang LK, Sundang M, Rusdi NA, Maid M, Bakansing SM, Moktar J. 2024. GC-MS analysis of bioactive compounds in ethanolic extract on different parts of Ziziphus mauritiana. Biodiversitas 25: 3442-3453. Ziziphus mauritiana Lam., a tropical fruit-bearing tree commonly known as Bidara tree in Malaysia, has a long and rich history of use in traditional medicine. Cultures across the globe have utilized various parts of the plant, including its leaves, bark, fruit, and roots, to address a wide range of health issues, such as digestive disorders, skin conditions, and inflammatory ailments. This study aimed to comprehensively analyze the bioactive compounds present in different parts of Z. mauritiana using Gas Chromatography-Mass Spectrometry. Ethanolic extracts were prepared from the leaves, bark, stem, root, and fruit of the plant, and their chemical compositions were meticulously analyzed. The GC-MS analysis revealed a diverse array of bioactive chemicals belonging to various chemical classes, including organic acids, esters, silanes, and thiodipropionates. Notably, many of these identified compounds have demonstrated promising antibacterial, antioxidant, anti-inflammatory, and anticancer properties in previous scientific studies. The presence of these bioactive substances provides scientific support for the traditional medicinal uses of Z. mauritiana and underscores its potential as a valuable source for developing novel therapeutic agents. Further research is warranted to fully elucidate the individual bioactivities and potential synergistic effects of these compounds, paving the way for harnessing the full therapeutic potential of Z. mauritiana for improving human health and well-being.

##plugins.themes.bootstrap3.article.details##

References
Abdallah EM. 2017. Antibacterial activity of fruit methanol extract of Ziziphus spina-christi from Sudan. Intl J Curr Microbiol Appl Sci 6 (5): 38-44. DOI: 10.20546/ijcmas.2017.605.005.
Abubakar YS. 2021. Proximate and selected mineral elements analysis of Nigerian Ziziphus spina-christi (L.) wild edible fruit pulp. Earthline J Chem Sci 5 (1): 231-240. DOI: 10.34198/ejcs.5121.231240.
Adilah HN, Saleh MI, Az-Zahra NDA, Cho E, Sinaga E. 2023. Total phenolic and total flavonoid content, antioxidant activity, and nutritional profile of Ziziphus mauritiana fruit juice. Intl J Biol Phys Chem Stud 5 (1): 01-08. DOI: 10.32996/ijbpcs.2023.5.1.1.
Ahmed WA, Salih N, Salimon J. 2023. Synthesis, characterization, tribological and rheological properties of di (2-butyl octyl) dicarboxylate esters for environmentally friendly biolubricant applications. Biointerface Res Appl Chem 1: 2783. DOI: 10.33263/BRIAC133.278.
Akanda MKM, Hasan AN. 2021. Characterization of pharmacological properties of methanolic seed and stem bark extracts of Ziziphus mauritiana (BAU Kul) using in-vitro and in-vivo animal (Swiss albino male mice) model. Clin Phytosci 7: 8. DOI: 10.1186/s40816-020-00246-0.
Akassh M, Fathima T, Mruthunjaya K. 2020. Health promoting effects of Ziziphus mauritiana: An overview. Intl J Res Pharm Sci 11: 1067-1072. DOI: 10.26452/ijrps.v11i1.1937.
Al Bratty M, Makeen HA, Alhazmi HA, Syame SM, Abdalla AN, Homeida HE, Sultana S, Ahsan W, Khalid A. 2020. Phytochemical, cytotoxic, and antimicrobial evaluation of the fruits of miswak plant, Salvadora persica L. J Chem 1: 4521951. DOI: 10.1155/2020/4521951.
Babu PS, Krishna V, Bhavya DC. 2023. Hepatoprotective activity of Tridecan-1-ol isolatedfrom Flaveria trinervia (Speng). C. Mohr. GSC Biol Pharm Sci 22: 271-279. DOI: 10.30574/gscbps.2023.22.3.0093.
Benidir M, El Massoudi S, El Ghadraoui L, Lazraq A, Benjelloun M, Errachidi F. 2020. Study of nutritional and organoleptic quality of formulated juices from jujube (Ziziphus lotus L.) and dates (Phoenix dactylifera L.) fruits. Sci World J 1: 9872185. DOI: 10.1155/2020/9872185
Byalt VV, Korshunov MV. 2021. Ziziphus mauritiana Lam. f. pendula VV Byalt & Korshunov (Rhamnaceae), a new form of an alien species newly recorded for the United Arab Emirates. Skvortsovia: Intl J Salicol Plant Biol 7 (2): 30-40. DOI: 10.51776/2309-6500.
Campana R, Mangiaterra G, Tiboni M, Frangipani E, Biavasco F, Lucarini S, Citterio B. 2020. A fluorinated analogue of marine bisindole alkaloid 2, 2-Bis (6-bromo-1 H-indol-3-yl) ethanamine as potential anti-biofilm agent and antibiotic adjuvant against Staphylococcus aureus. Pharmaceuticals 13 (9): 210. DOI: 10.3390/ph13090210.
Chen YH, Chang YC, Chen YH, Zheng LG, Huang PC, Huynh TH, Peng BR, Chen YY, Wu YJ, Fang LS, Su JH. 2020. Natural products from octocorals of the genus Dendronephthya (Family Nephtheidae). Molecules 24: 5957. DOI: 10.3390/molecules25245957.
Diamante C, Zondlo Fiume M, Bergfeld WF, Belsito DV, Hill RA, Klaassen CD, Liebler DC, Marks JG, Shank RC, Slaga TJ, Snyder PW. 2010. Final safety assessment of thiodipropionic acid and its dialkyl esters as used in cosmetics. Intl J Toxicol 29: 137S-50S. DOI: 10.1177/109158181037315.
Egbe NE, Garba S, Adamu A, Aliyu F. 2022. Phytochemical screening, in vitro antioxidant and gc-ms analysis of Ziziphus mauritiana leaves extract. Bima J Sci Technol 6: 80-90. DOI: 10.56892/bima.v6i03.48.
Ekiert HM, Szopa A. 2023. Biological activities of natural products III. Molecules 28 (12): 4854. DOI: 10.3390/molecules28124854.
Ferdosi MF, Javaid A, Khan IH, Khan S, Shad N. 2021. Analysis of n-butanol flower extract of Cassia fistula through GC-MS and identification of antimicrobial compounds. Pak J Pyhtopathol 33 (1): 103-107. DOI: 10.33866/phytopathol.033.01.0661.
Gregory GJ, Boas KE, Boyd EF. 2021. The organosulfur compound dimethylsulfoniopropionate (DMSP) is utilized as an osmoprotectant by Vibrio species. Appl Environ Microbiol 87 (5): e02235-20. DOI: 10.1128/AEM.02235-20.
Hassan AA, Abd-Elaziz GO. 2020. Genotoxicity and antimicrobial activity of Myrtus communis L., Ziziphus spina-christi (L.) Willd and Cassia angustifolia Vahl extracts. Bangladesh J Bot 49 (3): 557-566. DOI: 10.3329/bjb.v49i3.49640.
Hogue C. 2018. Siloxanes are candidates for tight control in EU. Chem Eng News 96 (27): 15-15. DOI: 10.1021/cen-09627-polcon4.
Huang L, Zhu X, Zhou S, Cheng Z, Shi K, Zhang C, Shao H. 2021. Phthalic acid esters: Natural sources and biological activities. Toxins 13 (7): 495. DOI: 10.3390/toxins13070495.
Jasim H, Hussein AO, Hameed IH, Kareem MA. 2015. Characterization of alkaloid constitution and evaluation of antimicrobial activity of Solanum nigrum using gas chromatography mass spectrometry (GC-MS). J Pharmacognosy Phytother 7: 56-72. DOI: 10.5897/JPP2015.0346.
Katz DH, Marcelletti JF, Khalil MH, Pope LE, Katz LR. 1991. Antiviral activity of 1-docosanol, an inhibitor of lipid-enveloped viruses including herpes simplex. Proc Nat Acad Sci U S A 88 (23): 10825-10829. DOI: 10.1073/PNAS.88.23.10825.
Keita S, Wele M, Cisse C, Togola I, Diarra N, Baba-Moussa L. 2020. Phytochemistry and biological activities of leaves and pulp extracts from Ziziphus mauritiana (Lam.) collected in Mali. J Adv Biol Biotechnol 23: 1-10. DOI: 10.9734/JABB/2020/v23i130133.
Khan MP, Ahmad M, Zafar M, Sultana S, Ali MI, Sun H. 2015. Ethnomedicinal uses of edible wild fruits (EWFs) in Swat Valley, Northern Pakistan. J Ethnopharmacol 173: 191-203. DOI: 10.1016/j.jep.2015.07.029.
Khromykh NO, Lykholat YV, Didur OO, Sklyar TV, Davydov VR, Lavrentiev? KV, Lykholat TY. 2022. Phytochemical profiles, antioxidant and antimicrobial activity of Actinidia polygama and A. arguta fruits and leaves. Biosyst Divers 30: 39-45. DOI: 10.15421/012205.
Kirby SA, Dowd CS. 2021. Phosphoryl prodrugs: Characteristics to improve drug development. Med Chem Res 31 (2): 207-216. DOI: 10.1007/s00044-021-02766-x.
Kishor R, Bharagava RN, Ferreira LF, Bilal M, Purchase D. 2021. Molecular techniques used to identify perfluorooctanoic acid degrading microbes and their application in a wastewater treatment reactor/plant. In: Shah MP, Rodriguez-Couto S (eds). Wastewater Treatment Reactors. Elsevier, Amstredam. DOI: 10.1016/B978-0-12-823991-9.00009-5.
Kushwaha P, Yadav SS, Singh V, Dwivedi LK. 2020. GC-MS analysis of bio-active compounds in methanolic extract of Ziziphus mauritiana fruit. Intl J Pharm Sci Res 10 (6): 2911-2916. DOI: 10.13040/IJPSR.0975-8232.10(6).2911-16.
Liaqat M, Mahmud TA, Ashraf MU, Muddassar MU, Imran M, Ahmad T, Mitu LI. 2017. Synthesis, characterization and biological activities of a novel mannich base 2- [(3, 4-dimethoxyphenyl) (pyrrolidinyl) methyl] cyclohexanone and its complexes with Cu (II), Ni (II), Co (II) and Fe (II) ions. Revista De Chimie 68 (12): 2845-2849. DOI: 10.37358/RC.17.12.5991.
Maruza IM, Musemwa L, Mapurazi S, Matsika P, Munyati VT, Ndhleve S. 2017. Future prospects of Ziziphus mauritiana in alleviating household food insecurity and illnesses in arid and semi-arid areas: A review. World Dev Perspect 5: 1-6. DOI: 10.1016/j.wdp.2017.01.001.
Mohamed KK, Banu RF, Kumar VA, Sundaram L, Thyagarajan SP. 2022. GC-MS and surface characteristics of polyvinyl siloxane-an in vitro analysis. J Chromatogr Sci 60 (2): 111-116. DOI: 10.1093/chromsci/bmab054.
Mohamed MF, Hassaneen HM, Elzayat EM, El-Hallouty SM, El-Manawaty M, Saleh FM, Mohamed Y, El-Zohiry D, Fahmy G, Abdelaal N, Hassanin N. 2019. Biological activity, apoptotic induction and cell cycle arrest of new hydrazonoyl halides derivatives. Anti-Cancer Agents Med Chem 19 (9): 1141-1149. DOI: 10.2174/1871520619666190306123658.
Mohd Jailani FNAM, Zaidan UH, Hanizam Abdul Rahim MB, Abd Gani SS, Halmi MI. 2020. Evaluation of constituents and physicochemical properties of Malaysian underutilized Ziziphus mauritiana (Bidara) for nutraceutical potential. Intl J Fruit Sci 20 (3): 394-402. DOI: 10.1080/15538362.2019.1641458.
Montiel MC, Máximo MF, Serrano-Arnaldos M, Ortega-Requena S, Murcia MD, Bastida J. 2019. Biocatalytic solutions to cyclomethicones problem in cosmetics. Eng Life Sci 19 (5): 370-388. DOI: 10.1002/ELSC.201800194.
Mukovoz PP, Slepukhin PA, Danilova EA, Aysuvakova OP, Glinushkin AP. 2008. Synthesis, structure, and biological activity of products of reactions of 3, 4-dioxohexane-1, 6-dioic acid esters with 2-aminophenol. Russian J General Chem 88: 1363-1368. DOI: 10.1134/S1070363218070022.
Nikonov AY, Sterkhova IV, Lazareva NF. 2021. 2, 2-Dimethyl-3-[(4-methylphenyl) sulfonyl]-2, 3-dihydro-1, 3, 2-benzoxazasilole: synthesis, properties, and structure. Russian Chem Bull 70 (2): 386-90. DOI: 10.1007/s11172-021-3097-3.
Paprocka R, Wiese-Szadkowska M, Ko?odziej P, Kutkowska J, Balcerowska S, Bogucka-Kocka A. 2023. Evaluation of biological activity of new 1, 2, 4-triazole derivatives containing propionic acid moiety. Molecules 28 (9): 3808. DOI: 10.3390/molecules28093808.
Prakash O, Usmani S, Singh R, Singh N, Gupta A, Ved A. 2021. A panoramic view on phytochemical, nutritional, and therapeutic attributes of Ziziphus mauritiana Lam.: A comprehensive review. Phytother Res 35 (1): 63-77. DOI: 10.1002/ptr.6769.
Quaranta A, Revol-Cavalier J, Wheelock CE. 2022. The octadecanoids: An emerging class of lipid mediators. Biochem Soc Transac 50 (6): 1569-1582. DOI: 10.1042/BST20210644.
Rashwan AK, Karim N, Shishir MR, Bao T, Lu Y, Chen W. 2020. Jujube fruit: A potential nutritious fruit for the development of functional food products. J Funct Foods 75: 104205. DOI: 10.1016/j.jff.2020.104205.
Ratto A, Honek JF. 2024. Oxocarbon acids and their derivatives in biological and medicinal chemistry. Curr Med Chem 31 (10): 1172-1213. DOI: 10.2174/0929867330666230313141452.
Rodrigues JL. 2022. Heterologous production of acrylic acid: Current challenges and perspectives. Synbio 1: 3-32. DOI: 10.3390/synbio1010002.
Roman G. 2015. Mannich bases in medicinal chemistry and drug design. Eur J Med Chem 89: 743-816. DOI: 10.1002/CHIN.201506309.
Sahu MK, Suthakaran S, Ghosh SC, Singh D, Das A, Jha H. 2023. Anticancer activity of secondary metabolite isolated from the rhizospheric fungus Fusarium oxysporum isolate-ABRF1, 2-propenoic acid, pentadecyl ester. Asian J Nat Prod Biochem 21 (2): 88-100. DOI: 10.13057/biofar/f210205.
Sangeetha C, Krishnamoorthy AS, Amirtham D. 2015. Antifungal bioactive compounds from Chinese caterpillar fungus (Ophiocordyceps sinensis (Berk.) GH Sung et al.) against plant pathogens. Madras Agric J 102: 1. DOI: 10.29321/MAJ.10.001133.
Sapijanskait?-Banevi? B, Grybait? B, Vaickelionien? R, Bružait? I. 2023. Synthesis, transformation and preliminary bioassay of 3-(thiazol-2-yl (p-tolyl) amino) propanoic acid derivatives. Chemija 34 (1): 57-69. DOI: 10.6001/chemija.2023.34.1.7.
Saribekova D, Kunik O, Harhaun R, Saleba L, Cavallaro G. 2021. The use of silicones as extractants of biologically active substances from vegetable raw materials. Appl Sci 11 (22): 10625. DOI: 10.3390/app112210625.
Seenivasan N. 2018. Phytochemical profiling of burrowing nematode (Radopholus similis) resistant and susceptible banana (Musa spp.) genotypes for detection of marker compounds. Fruits 73 (1): 48-59. DOI: 10.17660/th2018/73.1.6.
Shaaban MT, Ghaly MF, Fahmi SM. 2021. Antibacterial activities of hexadecanoic acid methyl ester and green?synthesized silver nanoparticles against multidrug?resistant bacteria. J Basic Microbiol 61 (6): 557-568. DOI: 10.1002/JOBM.202100061.
Shen C, Wang C, Zhao S, Guo Q. 2023. Acrylamide, acrylic acid, or 2?acrylamido?2?methyl?1?propanesulfonic acid induced cytotoxic in Photobacterium phosphoreum, PC12, and SK?N?SH cells. Environ Toxicol 38 (3): 489-499. DOI: 10.1002/tox.23673.
Sonawane U, Agarwal AK. 2023. Comparative spray atomization and evaporation characteristics of dimethyl ether and mineral diesel. J Energy Resour Technol 145 (12): 121201. DOI: 10.1115/1.4062619.
Soraya S, Sukara E, Sinaga E. 2022. Identification of chemical compounds in Ziziphus mauritiana Fruit juice by GC-MS and LC-MS/MS analysis. Intl J Biol Phys Chem Stud 4 (2): 11-19. DOI: 10.32996/ijbpcs.2022.4.2.2.
Srinivasulu K, Babu BH, Kumar KS, Reddy CB, Raju CN, Rooba D. 2008. Synthesis and bioactivity of 6?bromo?2?(substituted) ?3?(1?phenyl?ethyl) ?3, 4?dihydro?1H?isophosphinoline 2?chalcogenides. J Heterocycl Chem 45 (3): 751-757. DOI: 10.1002/CHIN.200839173.
Strobykina IY, Nemtarev AV, Garifullin BF, Voloshina AD, Sapunova AS, Kataev VE. 2019. Synthesis and biological activity of alkane-1, 1-diylbis (phosphonates) of diterpenoid isosteviol. Russian J Organic Chem 55: 17-24. DOI: 10.1134/S1070428019010044.
Sucheta, Tahlan S, Verma PK. 2007. Biological potential of thiazolidinedione derivatives of synthetic origin. Chem Central J 11: 130. DOI: 10.1186/S13065-017-0357-2.
Sudharsan S, Saravanan R, Shanmugam A, Vairamani S, Kumar RM, Menaga S, Ramesh N. 2011. Isolation and characterization of octadecanoic acid from the ethyl acetate root extract of Trigonella foneum graecum L. by using hydroponics method. Bioterrorism Biodefense 2 (1): 1-4. DOI: 10.4172/2157-2526.1000105.
Suriani NL. 2016. Identification of the substance bioactive leaf extract Piper caninum potential as botanical pesticides. Intl J Pure App Biosci 4 (4): 26-32. DOI: 10.18782/2320-7051.2337.
Terent? eva EO, Saidov AS, Khashimova ZS, Tseomashko NE, Sasmakov SA, Abdurakhmanov DM, Vinogradova VI, Azimova SS. 2017. Synthesis and biological activity of 1, 11-bis (6, 7-methylenedioxy-and 6, 7-dimethoxy-1, 2, 3, 4-tetrahydroisoquinolin-1-yl) undecanes. Chem Nat Compounds 53: 328-332. DOI: 10.1007/S10600-017-1981-8.
Tewari H, Jyothi KN, Kasana VK, Prasad AR, Prasuna AL. 2015. Insect attractant and oviposition enhancing activity of hexadecanoic acid ester derivatives for monitoring and trapping Caryedon serratus. J Stored Prod Res 61: 32-38. DOI: 10.1016/J.JSPR.2015.02.003.
Tian Z, Li Y, Zhou T, Ye X, Li R, Liu J. 2020. Structure dynamics reveal key residues essential for the sense of 1?dodecanol by Cydia pomonella pheromone binding protein 2 (CpomPBP2). Pest Manag Sci 76 (11): 3667-3675. DOI: 10.1002/PS.5915.
Tiwari AK, Gupta MK, Pandey G, Pandey PC. 2023. Siloxane-silver nanofluid as potential self-assembling disinfectant: A preliminary study on the role of functional alkoxysilanes. Nanoarchitectonics 1-15. DOI: 10.37256/nat.4120231576.
Tumosien? I, Jonuškien? I, Kantminien? K, Šiugždait? J, Mickevi?ius V, Beresnevi?ius ZJ. 2016. Synthesis and biological activity of 1, 3, 4-oxa (thia) diazole, 1, 2, 4-triazole-5-(thio) one and S-substituted derivatives of 3-((2-carboxyethyl) phenylamino) propanoic acid. Res Chem Intermediates 42: 4459-4477. DOI: 10.1007/S11164-015-2290-0.
Uygun Y, Bayrak H, Özkan H. 2013. Synthesis and biological activities of methylenebis-4H-1, 2, 4-triazole derivatives. Turk J Chem 37 (5): 812-823. DOI: 10.3906/KIM-1212-66.
Venn-Watson SK, Butterworth CN. 2022. Broader and safer clinically-relevant activities of pentadecanoic acid compared to omega-3: Evaluation of an emerging essential fatty acid across twelve primary human cell-based disease systems. PLoS One 17 (5): e0268778. DOI: 10.1371/journal.pone.0268778.
Wang H, Tian N, Chu D, Yan H. 2024. Synthesis and biological evaluation of 3, 9-Dioxatetraasteranes as potential inhibitors of epidermal growth factor receptor. Letters Drug Design Discover 21 (3): 552-558. DOI: 10.2174/1570180819666220928151144.
Winchester WR, Seymour J. 2022. Computational and dynamic NMR investigation of 2, 2?dimesityl?1, 1, 1, 3, 3, 3?hexamethyltrisilane. Magn Reson Chem 58 (4): 312-318. DOI: 10.1002/mrc.4991.
Wohlgemuth R. 2023. Advances in the synthesis and analysis of biologically active phosphometabolites. Intl J Mol Sci 24 (4): 3150. DOI: 10.3390/ijms24043150.
Yadav SM, Sharma VK, Sharma PK, Sharma J. 2022. Pharmacognostical, phytochemical, antimicrobial and hepatoprotective screening of some plants of family rhamnaceae. Intl J Health Sci (III): 4890-4911. DOI: 10.53730/ijhs.v6nS3.6985.
Yamini DP, Singh AK, Panigrahi HK. Morphological evaluation of tree, leaf and branch characteristics in indigenous ber (Ziziphus mauritiana Lamk.) at Bemetara district of Chhattisgarh. Intl J Adv Biochem Res 8 (8): 376-379. DOI: 10.33545/26174693.2024.v8.i8e.1760.
Yusof MY, Ramli MA. 2021. Local wisdom of Tahlil and Tunggu Kubur practices in death custom among The Malays in Malaysia. UMRAN-J Islamic Civilizational Stud 8: 39-48. DOI: 10.11113/umran2021.8n2.396.
Zablotskaya A, Segal I, Popelis Y, Grinberga S, Shestakova I, Nikolajeva V, Eze D. 2013. Silyl modification of biologically active compounds. 13. Synthesis, cytotoxicity and antibacterial action of N?methyl?N?(2?triorganylsiloxyethyl) ?1, 2, 3, 4?tetrahydro (Iso) Quinolinium Iodides. Appl Organometal Chem 27 (2): 114-124. DOI: 10.1002/AOC.2952.
Zhou Y, Cao F, Luo F, Lin Q. 2022. Octacosanol and health benefits: Biological functions and mechanisms of action. Food Biosci 47: 101632. DOI: 10.1016/j.fbio.2022.101632.

Most read articles by the same author(s)