GC-MS Profiling, Antimicrobial Activity of Annona squamosa: An In-silico and Invitro Approach http://www.doi.org/10.26538/tjnpr/v7i8.19
Article Sidebar
Main Article Content
Abstract
Annona squamosa Linn. (Annonaceae) is a perennial plant that possesses anti-diabetic, antioxidant, anti-tumor, analgesic, and antimicrobial activity. The current study was designed to explore the phytochemicals using GC-MS analysis and to evaluate the antimicrobial activity followed by in-silico molecular docking study. The leaf powder of A. squamosa was successively extracted with n-hexane and methanol. The n-hexane fraction was subjected to GC-MS analysis. The extract was evaluated for antimicrobial activity to determine the zone of inhibition by disc diffusion method at concentrations of 12.5, 25, and 50 mg/ml. The minimum inhibitory
concentration was performed at 100, 50, 25, 12.5, 6.25, 3.12 and 1.56 mg/ml concentration, against gram-positive bacteria (Staphylococcus aureus ATCC-25923, Staphylococcus aureus ML-267, Staphylococcus aureus ATCC-29737, Staphylococcus aureus ATCC-29157, Bacillus subtilis-6633), and gram-negative organisms (Escherichia coli PBR-332, Escherichia coli JM-109, Klebsiella pneumoniae PB-12) using streptomycin (1 mg/ml) as standard. Insilico docking was carried out with AUTO-DOCK Tool 1.5.6 using Discovery Studio 3.5. The GC-MS study revealed 13 compounds, the major compounds were 16-hentriacontanone (41.95%); [(1R,2S,6S,7S,8S)-8-Isopropyl-1-methyl-3-methylene-tricyclo-[4.4.0.02,7]-decane] (15.91%) and caryophyllene (12.07%). The better zone of inhibition was found at a concentration of 50 mg/mL against all organisms whereas the Minimum Inhibitory Concentration was detected at 6.25mg/mL. The docking results revealed through Auto-Dock tool, a highest docking score of -5.2 each obtained from both the compounds caryophyllene and [(1R,2S,6S,7S,8S)-8-Isopropyl-1-methyl-3-methylenetricyclo-[4.4.0.02,7]-decane], which was compared to the that of standard trimethoprim as reported previously. The antimicrobial potential of A. squamosa leaf might be attributed to the synergistic influence of bioactive components identified from GC-MS analysis.
Article Details
This work is licensed under a Creative Commons Attribution-NonCommercial-NoDerivatives 4.0 International License.
References
Meher A, Behera B, Nanda BK. GC-MS investigation of phytocomponents present In Ethanolic extract of plant Ichnocarpus Frutescens (L.) W. T. Aiton aerial part. Int J Pharm Sci Res, 2019;10(10): 4711-4716.
Gundidza M. Antimicrobial activity of essential oil from Schinusmolle Linn. Cent Afr J Med. 1993;39(11):231-4.
Hassan A. Hemeg, Ihab M. Moussa, Sherin Ibrahim, Turki M. Dawoud, Jwaher H. Alhaji, Ayman S. Mubarak, Saleh A. Kabli,f Roua A. Alsubki, Azza M. Tawfik, Sherif A. Marouf. Antimicrobial effect of different herbal plant extracts against different microbial population. Saudi J Biol Sci. 2020 Dec; 27(12): 3221–3227. doi: 10.1016/j.sjbs.2020.08.015
Agrawal P, Rai V, Singh RB. Randomized placebocontrolled, single blind trial of holy basil leaves in patients with noninsulin-dependent diabetes mellitus. Int J. Clin PharmacolTher. 1996;34(9):406-9.
Dash S, Kar B, Sahoo N, Pattnaik G. Annonaine an Alkaloid from the Leaves of Custard Apple (Annona squamosa): A Comprehensive Review on its Phytochemicals and Pharmacological Activities. Asian J Chem. 2020; 32(8):1824-1836.
Shirwaikar A, Rajendran K, Kumar CD. Oral Antidiabetic Activity of Annona squamosa Leaf Alcohol Extract in NIDDM Rats. Pharm Biol. 2004; 42(1):30–35.
Marahatta AB, Aryal A, Basnyat RC. The phytochemical and nutritional analysis and biological activity of Annona squamosa Linn. Int J Herb Med. 2019; 7(4):19-28.
Zahid M, Mujahid M, Singh PK, Farooqui S, Singh K, Parveen S, Arif M. Annona Squamosa Linn. (Custard Apple): An Aromatic Medicinal Plant Fruit with immense Nutraceutical and Therapeutic Potentials. Int J Pharm Sci Res. 2018; 9(5):1745-1759.
Saha R. Pharmacognosy and pharmacology of Annona squamosa: A review. Int J Pharm Life Sci. 2011; 2(10):1183-1189.
Yang TH, Chen CM. Studies on the constituents of Annona squamosa L. J Chin Chem Soc. 1970; 17:243-250.
Safira A, Widayani P, An-Najaaty D, Rani CAM, Septiani M, Arengga Y, Putra S, Solikhah TI, Khairullah AR, Raharjo HM. A Review of an Important Plants: Annona squamosa Leaf. Pharmacogn J. 2022;14(2): 456-463.
Padhi LP, Panda SK, Dutta SK. In vitro evaluation of antibacterial potential of Annona squamosa L. and Annona reticulata L. from Similipal Biosphere Reserve, Orissa, India. J Agric Technol. 2011; 7,133.
Hota RN, Nanda BK, Behera BR, Bose A. Ameliorative effect of ethanolic extract of Limnophila rugosa (Scrophulariaceae) in paracetamol- and carbon tetrachlorideinduced hepatotoxicity in rats. Future J Pharm Sci. 2022; 8:6.
Sofowora A. Medicinal plants and Traditional Medicine in Africa, Spectrum Books Ltd (Pub), Ibadan; 1993.
Harborne JB. Phytochemical methods: A guide to modern techniques of plant analysis, Chapman and Hall Publication, London, UK, 1998;3.
Ayoola GA, Coker HAB, Adesegun SA, Adepoju BAA, Obaweya K, Ezennia EC, Atangbayila TO. Phytochemical screening and antioxidant activities of some selected medicinal plants used for malaria therapy in South Western Nigeria. Trop J Pharm Res. 2008; 7:1019-1024.
Evans WC. Pharmacology, Harcourt Brace and Company, Asia, Singapore, 1997;226.
Finar IL. Stereo chemistry and chemistry of natural products, second edition, Longman, Singapur, 1986;682.
Harborne JB. Phytochemical Methods, Springer (India) Pvt. Ltd, New Delhi, 2005;17.
Sangeetha VS, Babu M, Lawrence B. Phytochemical Analysis of Annona Reticulata L. Leaf Extracts. Int Res J Pharm App Sci. 2014; 4(5):4-8.
Mace GSL. Anaerobic bacteriology for clinical laboratories, Pharmacognosy. 1963; 23:89 - 91.
Ani NI, Okolo KO, Ofah RO. Evaluation of antibacterial, antioxidant, and anti-infammatory properties of GC/MS characterized methanol leaf extract of Terminalia superba (Combretaceae, Engl. & Diels). Future J Pharm Sci. 2023; 9:3.
El-Chaghaby GA, Ahmad AF, Ramis ES. Evaluation of the antioxidant and antibacterial properties of various solvents extracts of Annona squamosa L. leaves. Arab. J. Chem. 2014; 7:227-233.
Iyanda-Joel WO, Omonigbehin EA, Iweala EEJ, Chinedu SN. Antibacterial studies on fruit-skin and leaf extracts ofAnnona muricata in Ota, Nigeria. Earth Environ Sci. 2019; 331.
Brown-Driver V, Chen Z, Creighton C, Cunningham M, Finn J, Hilgers M, Kohnen L, Kwan B, Lam T, Li X, Nelson K, Shaw KJ, Stidham M, Trzoss M, Zhang J. Structure-based design of new DHFR-based antibacterial agents: 7-aryl-2,4-diaminoquinazolines. Bioorg Med Chem Lett. 2011; 21(18):5171-5176.
Ravishankara B, Riaz MVK, Vinaykumar NM, Shastri SL. Hepatoprotective activity and molecular docking studies of Chloroxylon swietenia DC. fruit extract phytocompounds. Int J Pharm Res. 2021; 13:2704–2717.
Sahoo S, Rath D, Kar DM, Pattanaik S. Hepatoprotective potency of Litsea glutinosa (L.) C.B. Rob. leaf methanol extract on H2O2-induced toxicity in HepG2 cells. J Ethnopharmacol. 2023; 304.
Wang L, Li YX, Ge WC, Yuan K. Chemical Composition and Antifungal Activity of Essential Oils of Eupatorium catarium and Eupatorium odoratum from China. Asian J Chem. 2014; 26(21):7168-7172.
Salvi P, Kumar G, Gandass N, Verma A, Rajarammohan S, Rai N, Gautam V. Antimicrobial Potential of Essential Oils from Aromatic Plant Ocimum sp.; A Comparative Biochemical Profiling and In-Silico Analysis. Agronomy. 2022; 12:627.
HoL J, Yang H, Lee HS, Hong SK. Chemical Composition and Antimicrobial Activity of Essential Oil from Cones of Pinus koraiensis. J Microbiol Biotechnol. 2008; 18(3): 497–502.
Andila P.S., Nugroho L.H. Antibacterial and phytochemical constituent of Etlingera rubroloba A.D. Poulsen extract, an endemic ginger from Wallacea Region, Indonesia. Biodiversitas. 2022;23(7): 646-3658.
Shafaghata A, Shafaghatlonbarb M. Antimicrobial Activity and Chemical Constituents of the Essential Oils from Flower, Leaf and Stem of Gypsophila bicolor from Iran. Nat Prod Commun. 2011; 6(2):275 - 276.
Silva DR, Endo EH, Filho BPD, Nakamura CV, De Souza A, Young MCM. Chemical Composition and Antimicrobial Properties of Piper ovatum Vahl. Molecules. 2009; 14: 1171-1182.
Taherkhani M, Rustaiyan A. Chemical Constituents, Antimicrobial Activity, Antioxidant and Total Phenolic Content Within the leaves of Thecocarpus meifolious Boiss, Umbelliferae Herbs Growing Wild in Iran. Asian J Chem. 2013; 25(13):173-7176.
Servi H, Vatansever C, Dogan A, Majeed VA. Antibacterial activity and essential oil composition of Calendula arvensis L. Int j second metab. 2020; 7(4):229–236.
Okagu IU, Ngwu UE, Odenigbo CJ. Bioactive Constituents of Methanol Extract of Xylopia aethiopica (UDA) Fruits from Nsukka, Enugu State, Nigeria. Open Access Library Journal, 2018;5.
Kumari N, Menghani E, Mithal R. GCMS analysis of compounds extracted from actinomycetes AIA6 isolates and study of its antimicrobial efficacy. Indian J Chem Technol. 2019;26:362-370.
Swamy MK., Arumugam G, Kaur R, Ghasemzadeh A, Yusoff MM, Sinniah UR. GC-MS Based Metabolite Profiling, Antioxidant and Antimicrobial Properties of Different Solvent Extracts of Malaysian Plectranthus amboinicus Leaves. Evid Based Complement Altern Med.
; Article ID 1517683.
Winslow LC, Kroll DJ. Herbs as medicines. Arch Intern Med. 1998; 158(20):2192–2199.
Zhang L, Yuan B, Wang H, Gao Y. Therapeutic effect of Agaricus brasiliensis on phenylhydrazine-induced neonatal jaundice in rats. Biomed Res Int. 2015; 1–6.
Yamunadevi M, Wesely EG, Johnson M. Phytochemical studies on the terpenoids of medicinally important plantAervalanata L. using HPTLC. Asian Pac J Trop Biomed. 2011; 220-225.
Yoon BK, Jackman JA, Valle-González ER, Cho NJ. Antibacterial free fatty acids and monoglycerides: biological activities, experimental testing, and therapeutic applications. Int J Mol Sci. 2018; 19(4):1-40.
Desbois AP, Smith VJ. Antibacterial free fatty acids: activities, mechanisms of action and biotechnological potential. Appl Microbiol Biotechnol. 2010; 85(6):629–1642.
Rogerson ML, Robinson BH, Bucak S, Walde P. Kinetic studies of the interaction of fatty acids with phosphatidylcholine vesicles (liposomes). Colloids Surf B. 2006; 48(1): 24–34.
Perigo CV, Torres RB, Bernacci LC, Guimaraes EF, Haber LL, Facanali R, Vieira MAR, Quecini V, Marques MOM. The chemical composition and antibacterial activity of eleven Piper species from distinct rainforest areas in Southeastern Brazil. Ind Crops Prod. 2016; 94: 528–539.
Swamy MK, Akhtar MS, Sinniah UR. Antimicrobial Properties of Plant Essential Oils against Human Pathogens and Their Mode of Action: An Updated Review. Evid Based Complement Altern Med. 2016; Article ID 3012462.
Berrin O, Ilhan G, Taner K, Erdem Y. Antiviral and antimicrobial activities of three sesquiterpene lactones fromCentaurea solstitialis L. ssp. Solstitialis. Microbiol Res. 2009; 164(5): 545-52.
Hang-Ying L, Wen-Qian Y, Xin-Zhu Z, Fei S, Tong S, HuiYing G, Jie Z, Li-Ming Z. Antibacterial and Antifungal Sesquiterpenoids: Chemistry, Resource, and Activity. Biomolecule. 2022; 12:1271.
Chopra I, Greenwood D. Nature Publishing Group. John Wiley and Sons, Limited; 2001.
Chan EWC, Lim YY, Omar M. Antioxidant and antibacterial activity of leaves of Etlingera species (Zingiberaceae) in Peninsular Malaysia. Food Chem. 2007; 2007104: 1586–1593.