Antimicrobial activity, bioactive constituents, and functional groups in aqueous methanol extract of Polyalthia longifolia (Sonn.) thwaites leaves
Feyisara Banji Adaramola1, Roger Murugas Cooposamy2, Olufunmiso Olusola Olajuyigbe3
1 Department of Basic Sciences, Chemistry Unit, School of Science and Technology, Babcock University, Ilisan Remo, Ogun State, Nigeria
2 Department of Nature Conservation, Faculty of Natural Sciences, Mangosuthu University of Technology, Durban, South Africa
3 Department of Nature Conservation, Faculty of Natural Sciences, Mangosuthu University of Technology, Durban, South Africa; Department of Microbiology, School of Science and Technology, Babcock University, Ilisan Remo, Ogun State, Nigeria
|Date of Submission||03-Mar-2020|
|Date of Decision||15-Apr-2020|
|Date of Acceptance||15-Jul-2020|
|Date of Web Publication||11-Nov-2021|
Olufunmiso Olusola Olajuyigbe
Department of Microbiology, School of Science and Technology, PMB 4005, Babcock University, Ilisan-Remo, Ogun State
Source of Support: None, Conflict of Interest: None
| Abstract|| |
Background: Polyalthia longifolia is an ornamental plant with various applications in traditional medicine. There is a need to identify its bioactive compounds to justify its medicinal use. Objectives: In this study, the functional groups and bioactive compounds in aqueous methanol extract of P. longifolia leaves and its antimicrobial potential were investigated. Materials and Methods: Bioactive constituents of the extract were assayed with gas chromatography-mass spectrometry (GC-MS) and functional groups by Fourier transform infra-red (FT-IR), while its phytochemical screening and antimicrobial activity were investigated in vitro using standard protocols. Results: Qualitative phytochemical screening showed the presence of therapeutically important phytochemicals, namely, alkaloids, steroidal and cardiac glycosides, saponins, triterpenes, steroids, phytosterols, resins, phenols, flavonoids, tannins, and diterpenes. The extract showed promising bactericidal and fungicidal properties against the test organisms. Staphylococcus aureus was the most resistant of all the test organisms, while other test organisms were significantly inhibited by the extract in a concentration-dependent fashion. FT-IR analysis showed different characteristic peak values confirming the presence of important functional groups, namely, alcohol, alkane, ester, alkene, nitro compounds, amine, carboxylic acid, aromatics, and alkyl halide in the extract. GC-MS analysis identified 25 bioactive compounds in the leave extract. Some of these compounds include 2-methoxy-4-vinylphenol, copaene, aromadendrene, alpha-curcumene, caryophyllene oxide, palmitic acid methyl ester, cis-Z-alpha-Bisabolene epoxide, phytol, alpha-Santoline alcohol, and linolenic acid ethyl ester reportedly possessing antimicrobial, antioxidant, antigenotoxic, antiproliferative, anti-inflammatory, anticarcinogenic, cardio-protective, insecticidal, pesticidal, nematicidal, antiandrogenic, antiviral, and analgesic activities. Conclusion: This study underscores the vast therapeutic importance of P. longifolia leaves as an important source of potentially useful bioactive principles.
Keywords: Aqueous methanol extract, antimicrobial, bioactive compounds, functional group, Polyalthia longifolia
|How to cite this article:|
Adaramola FB, Cooposamy RM, Olajuyigbe OO. Antimicrobial activity, bioactive constituents, and functional groups in aqueous methanol extract of Polyalthia longifolia (Sonn.) thwaites leaves. Phcog Mag 2021;17:594-604
|How to cite this URL:|
Adaramola FB, Cooposamy RM, Olajuyigbe OO. Antimicrobial activity, bioactive constituents, and functional groups in aqueous methanol extract of Polyalthia longifolia (Sonn.) thwaites leaves. Phcog Mag [serial online] 2021 [cited 2021 Nov 30];17:594-604. Available from: http://www.phcog.com/text.asp?2021/17/75/594/330229
- The leaves of Polyalthia longifolia could be used in the treatment of infections in ethnomedicine
- There are bioactive compounds of therapeutic values in its extract
- The potential effectiveness of this plant in the treatment of microbial infections could be related to the pharmacological activities of the identified bioactive compounds.
- Investigating the pharmacological activities of unknown bioactive compounds such as 4, 8, 8-trimethyl-2-methylene-Bicyclo[5.2.0] nonane, 4-methylene-1-methyl-2-(2-methyl-1-propen-1-yl)-1-vinyl-Cycloheptane, 3-(4-Hydroxybutyl)-2-methylcyclohexanone, 1, 4, 4a, 5, 6, 9, 10, 10a-octahydro-11,11-dimethyl-1,4-Methanocycloocta[d] pyridazine, and Guaia-1 (10),11-diene could be a baseline for further study in the discovery of novel drug compounds.
- The study could form the basis for selecting this plant species for further investigation in the discovery of novel drug compounds to be used in the treatment of infections.
Abbreviations used: FT-IR: Fourier transform-infrared; KBr: Potassium bromide; GC-MS: Gas chromatography-mass spectrophotometry; NIST: National Institute of Standards and Technology; DMSO: Dimethyl sulfoxide.
| Introduction|| |
For several years, plants and plant products have played significantly positive roles in the health of humans and their environment. They have continually provided human with oxygen for breathing and provided nutrients through edible plants parts and bioactive ingredients as medicine for human health care. Human's continuous search for safer, cheaper, and a more readily available medicine with little or no side effects has made medicinal plants of very great importance. This is because medicinal plants possess several phytochemicals, which have shown laudable efficacy in combating both infectious and lifestyle diseases. It is, therefore, not surprising that in spite of the current huge scientific development, the role of medicinal plants remains significant in providing health care for about 80% of human population, especially in the developing nations. In fact, medicinal plants are a source of inspiration for many modern-day drug formulations. In the pharmaceutical industry, medicinal plants form an essential part of research and developments focusing on isolation or direct use of bioactive principles, the development of semi-synthetic drugs, or active screening of natural products to obtain synthetic pharmacologically potent compounds. While their medicinal properties have been attributed to the presence of phytochemicals exerting definite physiological influence on human body, various pharmacological studies have recognized the relevance and importance of medicinal plants as potential sources of bioactive compounds., Consequently, Mukherjee et al. and Sheeja and Kuttan reported that plant-sourced bioactive compounds have resulted in the discovery of new drugs effective for protection against and treatment of various diseases including cancer and Alzheimer's disease although beneficial pharmacological effects of plants and plant materials typically result from the combined effects of bioactive compounds such as alkaloids, steroids, tannins, glycosides, volatile oils, fixed oils, resins, phenols, and flavonoids, which are present in different plants' tissues including leaves, flowers, bark, seeds, fruits, and roots.
Polyalthia longifolia belonging to the family Annonaceae is one of such plants with both ornamental and numerous medicinal importance. The genus Polyalthia has about 120 species widely distributed in Africa, South-Eastern Asia, Australia, and New Zealand. Although this plant is ornamental, P. longifolia finds its reference in Indian medicinal literature owing to its popular Hindi name Ashoka and a number of biologically active principles that have been identified in this plant., In traditional medicine, different parts of the plant have been exploited for the treatment of many ailments such as septic infection, diarrhea, cancer, and hepatosplenomegaly. In India, fever, mouth ulcer, uterus-related ailments, gonorrhea, and heart diseases are being treated with the leaves, while the stem bark are used to treat hypertension and diabetes. As an antipyretic agent in traditional medicine, it is pharmacologically active as antimicrobial,, and cytotoxic, with hypotensive effect. Furthermore, Osuntokun et al. reported that its fruits, stem bark, roots, and leaves have been used in ethnomedicine for their potent antibacterial, antifungal, antidiabetic, anti-inflammatory, and antioxidant activities in Nigeria. Considering ethnotherapeutic relevance of this plant, identifying potentially bioactive compounds of therapeutic importance in its parts becomes essential. This study, therefore, investigated the bioactive principles and antimicrobial potentials of aqueous methanol extract of P. longifolia leaves in vitro.
| Materials and Methods|| |
Collection of plant sample
Fresh and mature leaves of P. longifolia were obtained from its tree within Babcock University campus where it was growing in its natural habitat. The leaves were thoroughly washed with copious amount of water and dried at room temperature for 2 weeks. They were subsequently pulverized with a LEXUS MG-2053 OPTIMA laboratory grinder and kept in polyethylene bags for further use.
Extraction of leaf sample
Fifty grams of the pulverized leaves was macerated in 400 mL of methanol (80%) for 72 h with intermittent shaking. The mixture was filtered at three consecutive times with Whatman No 1 filter paper plucked with cotton wool and the filtrates were combined. The combined filtrate was evaporated to dryness under reduced pressure with rotary evaporator EYELA N-1001 at 40°C. The dried extract was kept in an airtight glass tube and stored in the refrigerator at 4°C for further use.
Functional group analysis by Fourier transform infrared
In order to determine the chemical bonds/functional groups present in the methanol extract of P. longifolia leaves, the extract was subjected to Fourier transform infrared (FT-IR) spectroscopic analysis. Ten mg of the powdered extract was then encapsulated in 100 mg of potassium bromide (KBr) pellet to obtain translucent sample discs. The encapsulated powdered sample was loaded in a Bruker FT-IR spectrophotometer (PerkinElmer, City, Country Waltham, MA, USA) for analysis by scanning at wavelengths ranging from 300 to 3500 cm−1 at a resolution of 4 cm−1. The percentage of transmission was recorded against the wave numbers. Peak values were recorded, and the functional groups were predicted.
Gas chromatography mass spectrometry analysis of the extract
Bioactive compounds in methanol extract of P. longifolia leaves were identified by gas chromatography mass spectrometry (GC-MS) equipped with GCMS-QP2010 : SHIMADZU (Shimadzu Corporation). The GC-MS was equipped with a split injector and an ion-trap mass spectrometer detector with a fused-silica capillary column of 1.00 μm thickness, 30 mm × 0.25 mm dimension, and a programmed temperature ranging from 60°C to 250°C at 3.0°C/min. The injector temperature was 250°C, while the detector temperature was 200°C. Helium served as the carrier gas at 46.3 cm/s flow rate. Comparing average peak area of individual compound with the total area, the relative percentage of each identified compound was determined. Identification of components was done through computerized matching of their spectra with the spectra of known compounds from the spectra Library of National Institute of Standards and Technology (NIST, 2009). The fragmentation patterns of the compounds eluted were identified by comparison with known data from the database.
The presence of secondary metabolites including alkaloids, tannins, flavonoids, phenolics, steroids, glycosides, saponins, terpenoids, reducing sugar, fixed oil, resin, anthraquinone, phlobatannins, and phytosterols in the aqueous methanol extract of P. longifolia leaves was determined by preliminary screening of its phytochemical according to the methods of Trease and Evans and Rajeshwari et al.
Antimicrobial activity assay
The antimicrobial activity of P. longifolia leave aqueous methanol extract against clinical isolates of Gram-negative and Gram-positive bacteria and a fungus was carried out using agar diffusion method. These organisms including Staphylococcus aureus ATCC 6538, Enterococcus faecalis ATCC 29212, Bacillus cereus ATTC 10702R, Klebsiella pneumoniae ATCC 10031, Proteus vulgaris ATCC 6830R, Pseudomonas aeruginosa ATCC 19582, and Candida albicans obtained from Babcock University Teaching Hospital Laboratory, Ilisan-Remo, Ogun State, Nigeria. The test bacteria were grown in nutrient broth for 24 h, while the fungus was grown in potato dextrose broth for 5 days. The inocula of the test organisms were prepared using the colony suspension method. Colonies picked from 24-h-old cultures grown on nutrient agar were used to make suspensions of the test organisms in saline solution to give an optical density of approximately 0.1 at 600 nm. The suspension was then diluted 1:100 by transferring 0.1 ml of the bacterial suspension to 9.9 ml of sterile nutrient broth before being used. This assay was carried out according to the method described by Srinivasulu et al., Olajuyigbe and Afolayan, and Adaramola et al. Briefly, sterile Mueller–Hinton agar (Oxoids Ltd., Basingstoke, Hampshire, UK) plates were swabbed with the resultant saline suspension of each adjusted bacterial strain, while sterile potato dextrose agar plates were swabbed with the adjusted C. albicans. The wells were then bored into the agar medium using a heat-sterilized 6-mm cork borer. The wells were filled with 100 μl of each extract concentration along with 100 μL of ciprofloxacin (2.5 μg/ml) and fluconazole taking care not to allow spillage of the solutions onto the surface of the agar. The culture plates were allowed to stand on the laboratory bench for 1 h to allow proper diffusion of these solutions before being incubated at 37°C for 24 h for the bacterial isolates and 3–5 days for the fungus. Dimethyl sulfoxide served as the blank, while ciprofloxacin (for bacteria) and fluconazole (for fungi) were used as standard drugs. After the incubation period, the diameter of each zone of inhibition was recorded and expressed in millimeter. Minimum inhibitory concentration of the extract on the organisms was carried out at lower concentrations as described above. The entire microbial assay was conducted under strict aseptic conditions, and all analyses were carried out in triplicates.
| Results|| |
The results of preliminary phytochemical screening of the leave extract as presented in [Table 1] showed the presence of pharmacologically important phytochemicals such as alkaloids, steroidal and cardiac glycosides, saponins, triterpenes, steroids, phytosterols, resins, phenols, flavonoids, tannins, diterpenes, and carbohydrates, which could account for the antimicrobial activites of the plant. However, anthranol glycosides, fixed oil, anthraquinone, and phlobatannins were not detected in the leaf extract.
|Table 1: Phytochemicals in aqueous methanol extract of Polyalthia longifolia leaves|
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Fourier transform infra-red analysis
The FT-IR spectrum of aqueous methanol extract of P. longifolia leave is presented in [Figure 1], while the peak value data and the probable functional groups present in the extract are presented in [Table 2]. The FT-IR analysis indicated the presence of O–H (alcohol), –C–H (alkane), C=O (ester), C=C (alkene), N–O (nitro compound), C–N (amine), O–H bending (carboxylic acid), C–H bending (aromatics), and C–Cl (alkyl halide) in methanol extract. The presence of these functional groups could be responsible for the various pharmacological properties of P. longifolia leave.
|Figure 1: Fourier transform infrared spectrum of aqueous methanol extract of Polyalthia longifolia leaves|
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|Table 2: Functional groups in aqueous methanol extract of Polyalthia longifolia leaves|
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In the present study, the growth inhibitory ability of P. longifolia leaf methanol extract against test organisms is shown in [Table 3]. The results showed that S. aureus was the most resistant of all the test organisms because it showed no inhibition zones from 10 to 40 mg/mL concentrations but produced 15 ± 1.00 mm inhibition zone at 50 mg/mL extract's concentration. However, other test organisms were significantly inhibited by the extract at the concentrations ranging between 10 and 50 mg/L and mostly in a concentration-dependent trend. Meanwhile, inhibition zones of the test organisms ranged from 22 to 25 ± 1.00, 20–25 ± 1.00, 15–21 ± 1.00, 18–26 ± 1.00, 21–25 ± 1.00, and 18–26 ± 1.00 mm for E. faecalis, B. cereus, P. aeruginosa, K. pneumoniae, P. vulgaris, and C. albicans, respectively. The MIC values were obtained as 5 mg/mL for S. aureus and P. vulgaris; 3 mg/ml for E. faecalis; 1 mg/mL for B. cereus, P. aeruginosa, and K. pneumoniae; and 0.5 mg/mL for C. albicans.
|Table 3: Susceptibility of test microbial isolates to aqueous methanol extract of Polyalthia longifolia leaves|
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Gas chromatography-mass spectrometric analysis
[Figure 2] shows the GC-MS chromatogram of the extract, with peaks indicating the presence of 25 different compounds. The individual compounds with their respective properties are presented in [Table 4], while their biological activities are presented in [Table 5]. The most predominant compound identified in the leaf extract was 1,4-methanocycloocta[d] pyridazine, 1, 4, 4a, 5, 6, 9, 10, 10a-octahydro-11,11-dimethyl-(17.87%), while the least predominant compound was copaene (0.38%). Other compounds identified with relatively high concentration include aromadendrene (3.68%), caryophyllene oxide (3.40%), patchoulane (4.47%), 1-Octadecyne (3.12%), 16, 17-dimethyl-Pregn-4-ene-1, 20-Dione (2.74%), 4-methylene-1-methyl-2-(2-methyl-1-propen-1-yl)-1-vinyl-Cycloheptane (4.05%), phytol (5.68%), 1, 4, 4a, 5, 6, 7, 8, 8a-octahydro-9,9-dimethyl-1,4-Methanophthalazine, (3.60%), 4, 8, 8-trimethyl-2-methylene-Bicyclo [5.2.0] nonane (14.72%), 4-methylene-1-methyl-2-(2-methyl-1-propen-1-yl)-1-vinyl-Cycloheptane (6.90%), and 3-(4-Hydroxybutyl)-2-methylcyclohexanone (11.68%). The antimicrobial activity shown by the extract was further confirmed by the presence of therapeutically important compounds such as 2-Methoxy-4-vinylphenol, phytol, palmitic acid methyl ester, caryophyllene oxide, alpha-Curcumene, alpha-Santoline alcohol, aromadendrene, and copaene with reported antimicrobial properties, as shown in [Table 5].
|Figure 2: Gas chromatography-mass spectrometry chromatogram of aqueous methanol extract of Polyalthia longifolia leaves|
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|Table 4: Bioactive compounds identified in aqueous methanol extract of Polyalthia longifolia leaves|
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|Table 5: Bioactivity of compounds identified in aqueous methanol extract of Polyalthia longifolia leaves|
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| Discussion|| |
Phytotherapy, the use of plants and plant products in the management of disease, has gained significant attention in recent times. This could be attributed to their effectiveness as therapeutic tools in combating myriads of diseases. Medicinal plants are considered a repository of a vast array of bioactive principles such as ascorbic acid, carotenoids, alkaloids, tannins, flavonoids, phenolics, sterols, steroids, glycosides, saponins, terpenoids, and antocyanins, among others. The medicinal properties of plants are justifiably attributed, among other things, to these bioactive constituents, which have been shown to possess biological and therapeutic activities such as antimalaria, anti-inflammatory, anticancer, antibacterial, antifungal, antiviral, insecticidal, antioxidant, immune system stimulation, platelet aggregation reduction, and hormone metabolism modulation properties., In the present study, hydro-methanol extract of P. longifolia leaf assayed for the presence of various phytochemicals indicated the presence of specific bioactive compounds, functional groups, as well as its antimicrobial potential against clinical isolates.
Although phytochemicals are essential and required for sustenance of human life, they also possess important properties to prevent and protect human from all kinds of diseases. Alkaloids are a crucial drug source and reportedly possess antimicrobial, antioxidant, cytotoxic, anti-arrythmic, antihypertensive, anticancer, hypoglycemic, and antimalaria activities., While glycosides are employed in the treatment of congestive heart failure and cardiac arrhythmia, saponins possess hypocholesterolemic, antioxidant, antidiabetic, anti-inflammatory, immunostimulant, hypoglycemic, anticarcinogenic, and antifungal properties., Terpenes have excellent antioxidant activity. Steroids possess analgesic properties, and phytosterols have been reported to possess anti-inflammatory, anti-neoplastic, anti-pyretic, and immuno-modulating activities. Resins are known to possess antiseptic and antibacterial activities. Phenolic compounds possess several biological functions such as antioxidant, anticarcinogenic, and anti-inflammatory properties, which are attributed to their fundamental reducing abilities. Flavonoids have been studied extensively as antioxidant agents playing crucial functions in decreasing the risk of coronary heart disease, diabetes, hypertension, and certain forms of cancer in human beings., Tannins are used in antidiarrheal, hemostatic, and anti-hemorrhoidal formulations. The presence of these biologically important phytochemicals in P. longifolia leaf extract, therefore, underscores its medicinal values. However, the FT-IR spectroscopy which has proven to be a sensitive and valuable tool for identifying and characterizing functional groups or chemical bonds present in an unknown mixture of natural products and GC-MS able to identify various bioactive compounds in plant materials have helped in identifying the chemical makeups of the methanolic extract of P. longifolia. The therapeutic properties of these important bioactive constituents including antioxidant, antigenotoxic, antiproliferative, anti-inflammatory, anticarcinogenic, cardioprotective, insecticidal, pesticidal, nematicidal, antiandrogenic, antiviral, and analgesic based on reports from other studies underscore the veracity of this plant's usefulness in traditional medicine, while other compounds identified in the extract without biological activities found in literature could also contribute individually or synergistically to the pharmacological activities of the extract.
As it is crucial to investigate the potential pharmacological importance of these compounds to further identify more potential therapeutic activities of the extract, the ability of the extract to show antibacterial activity against multidrug-resistant clinical bacterial isolate is significant as the emergence and high prevalence of multidrug resistance among various strains of micro-organisms have become a serious public health concern. This is due to the inappropriate and continuous use of commercially available synthetic antimicrobials without prescriptions in treating infectious diseases. In addition to causing multidrug resistance necessitating the search for better alternative medicines from plants, these synthetic drugs are not without other adverse effects including addiction and high toxicity. However, plant-based remedies have provided enormous relief as their bioactive constituents have shown significant therapeutic potentials with minimal or lesser side effects as compared to synthesized drugs. Consequently, plant-based therapy has become a crucial component of traditional medical practices while serving as a major source of bioactive compounds for several major pharmaceutical drugs used in treating numerous diseases. Thus, plants are considered important sources of potentially useful bioactive principles for the development of new therapeutic agents.
Considering the level of poverty and knowledge about the relevance of medicinal plants in ethnomedicine especially in the developing nations, the use of medicinal plants as an alternative approach to therapy is complementary in achieving primary health-care delivery. While several biological activities including antimicrobial potential of plant extracts have been attributed to the presence of secondary metabolites which are known for their various pharmacological efficacies, their useful medicinal properties have been ascribed to the combined effects of these secondary metabolites. Antimicrobial activity of various extracts of P. longifolia leave have been reported by several authors., From this study, the bactericidal and fungicidal activities indicated by the extract could be associated with the presence of bioactive principles such as alkaloids, phenols, flavonoids, saponins, and tannins in the extract.
| Conclusion|| |
This study confirmed the presence of various pharmacologically important principles with a wide range of bioactivities including antimicrobial, antioxidant, antigenotoxic, antiproliferative, anti-inflammatory, anticarcinogenic, cardio-protective, insecticidal, pesticidal, nematicidal, antiandrogenic, antiviral, and analgesic activities in the aqueous methanol extract of P. longifolia leaves. Some of these compounds include 2-methoxy-4-vinylphenol, copaene, aromadendrene, alpha-curcumene, caryophyllene oxide, palmitic acid methyl ester, cis-Z-alpha-Bisabolene epoxide, phytol, alpha-Santoline alcohol, and linolenic acid ethyl ester. In addition, the antibacterial and antifungal activities of the extract against the test clinical isolates may be attributed to the presence of the aforementioned compound identified in the extract. This study underscores the medicinal veracity of P. longifolia leaf and thus suggests that the plant would make a good prospect for the isolation of bioactive compounds essential in drug formulation and its development.
The authors hereby acknowledge each contribution made toward the successful completion of this study
Financial support and sponsorship
Conflicts of interest
There are no conflicts of interest.
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[Figure 1], [Figure 2]
[Table 1], [Table 2], [Table 3], [Table 4], [Table 5]