INTRODUCTION:

Natural products derived from plants have long been recognized for their potential therapeutic properties^1,2. Ficus sycomorus commonly known as the sycamore fig is widely distributed in various regions of Africa, known for its diverse therapeutic properties, and qualities, and traditionally employed for treating several diseases^3-7. In recent years, there has been an increasing interest in exploring the phytochemical composition of medicinal plants to understand their therapeutic potential^8-10.

Ficus sycomorus plays a multifaceted role both ecologically and culturally. Ecologically, its fig fruits provide a vital food source for numerous animals, contributing to the balance of the ecosystem, while its deep root system serves to stabilize riverbanks and prevent soil erosion, making it indispensable in riparian habitats. Culturally, Ficus sycomorus holds deep significance across Africa and the Middle East, particularly in ancient Egypt, where it symbolized fertility, protection, and regeneration. It remains culturally important today, associated with prosperity and spiritual beliefs, and is utilized in various traditional practices such as forage, crafts, and shade provision, underscoring its enduring cultural relevance and practical utility¹¹.

Its medicinal properties have been explored, with extracts showing potential antioxidant, anti-inflammatory, and antimicrobial effects. As ongoing research uncovers more about its biological properties and traditional uses, the sycamore fig remains a compelling subject of study with implications for conservation, cultural heritage, and human health⁸.

Due to its potential, phytochemical analysis—which involves the detection, identification, and quantification of various bioactive compounds—particularly secondary metabolites like alkaloids, flavonoids, tannins, and phenolic compounds found in extracts of these plants' stem bark and leaves—has attracted attention. It also plays a critical role in comprehending the potential medical applications of these plants^12,13. Whereas qualitative screening clarifies whether a certain phytochemical ingredient is present or absent, quantitative screening determines the relative quantity of each phytochemical constituent in the plant material^14-16. Furthermore, a thorough examination of the chemical makeup and structural identification of particular individual compounds present in plant extracts can be achieved via spectroscopic characterization with techniques such as Fourier-transform infrared spectroscopy (FTIR) and gas chromatography-mass spectrometry (GC-MS)^17,18.

This work aims to bridge the existing knowledge regarding the composition of phytochemicals and spectroscopic characteristics of extracts from Ficus sycomorus stem bark and leaves. Integrating FTIR, GC-MS analysis, and phytochemical screening will enable a comprehensive investigation of these plant extracts. This will open up new paths for natural product research and development and illuminate any potential therapeutic qualities of the extracts. The goal is to improve our knowledge of the chemical makeup and possible bioactive compounds found in these extracts which will ultimately allow for further investigation into the therapeutic use of these plants and may result in the creation of novel therapeutic agents or the study of formulations based on natural products for a range of medical conditions.

MATERIALS AND METHODS:

Materials:

Chloroform, Sulphuric acid, Aluminum trichloride, ammonia, acetic anhydride, hydrochloric acid, potassium ferrocyanide, ferric chloride, methanol, iodine, sodium hydroxide, sodium carbonate, wargners reagent, buljets reagent, vanillin reagent, folins phenol reagent, sodium dihydrogen orthophosphate (All purchased from Sigma Aldrich, Germany) were among the chemicals been employed.

Methods:

Sample collection:

The collection of F. sycomorus leaves and stem barks was conducted at Wudil, located in Kano state, Nigeria. They were verified at the Bayero University Kano, Nigeria, biological science department's herbarium section, where a voucher with specimen number BUKHAN 109 was provided. The science faculty at Kano State University of Science and Technology in Wudil authorized this study.

Extraction of F. sycomorus:

The samples were shed dried for about 2 weeks and then were size reduced into fine powder. 300g and 290g of the fine powder of stem bark and leaves respectively were macerated in 2L hydro-alcoholic solvent (containing 70% methanol in water) in an amber air tide maceration container, The mixture was left to stand for a week before being filtered through fine cotton sieve material and a pressure-sanction machine¹⁹. The extracts were then dried using a water bath at 65ºC.

Qualitative analysis:

The presence or absence of specific chemicals in F. sycomorus extracts was ascertained using qualitative analysis. Standard operating procedures as follows were adhered. Qualitative analysis of various compounds in the plant extracts was conducted using specific methods. Anthraquinones were detected by treating stem-bark and leaf filtrates with diluted sulfuric acid and diluted ammonia, with the presence of a rose-pink coloring indicating a positive reaction. Yellow precipitates upon the addition of lead acetate solution indicated the presence of polyphenols, while the emergence of a blue-black or brownish-green hue after the addition of ferric chloride confirmed the existence of tannins. Flavonoids were identified by the yellow hue observed after adding diluted ammonia and concentrated sulfuric acid. The reddish-brown hue at the interface layer created by combining filtrate, chloroform, and concentrated sulfuric acid suggested the presence of terpenoids. Cardiac glycosides were detected through the formation of a brown ring upon mixing filtrates with glacial acetic acid, ferric chloride solution, and concentrated sulfuric acid. The presence of anthocyanins was indicated by a reddish-pink tint turning blue-violet upon the addition of HCl and ammonia to the aqueous filtrates. Phytosterols were detected by a color change from violet to blue or green after mixing methanolic extract with H2SO4 and acetic anhydride. Flavonols, flavones, triterpenoids, phlobatannins, coumarins, chalcones, quinones, saponins, and alkaloids were also qualitatively analyzed using specific reagents and observations for color changes or precipitate formation. These analyses provide insights into the diverse chemical composition of the plant extracts^15,20.

Quantitative analysis:

Quantitative analysis of various compounds from plant extracts was conducted using specific methods. Flavonoids were assessed by mixing plant extracts with acetic acid and aluminum trichloride solution, followed by spectrophotometric measurement at 415nm. Alkaloids were extracted by filtering a mixture of powdered drugs in acetic acid and ethanol, with subsequent precipitation, washing, drying, and weighing of the alkaloid residue. Tannins were evaluated by mixing the sample with FeCl3 and potassium ferrocyanide, and absorbance was measured at 720nm. Saponins were detected by adding vanillin solution and sulfuric acid to plant extract, with absorbance measured at 544nm after incubation. Total phenolics were determined by adding Na3CO2 and Folin's phenol reagent to the extract and measuring absorbance at 725 nm. Anthraquinones were extracted by soaking the sample in water, followed by thermal treatment, filtration, and spectrophotometric measurement at 450 nm. Cardiac glycosides were analyzed using Buljets reagent method, with absorbance measured to calculate the percentage of total glycosides. These analyses provide insights into the chemical composition and potential bioactive compounds present in the plant extracts^21,22.

FT-IR analysis:

An IR spectrum in the 4000-400 cm-1 range was collected using a Perkin-Elmer Fourier Transform spectrometer equipped with a DTGs detector. The process involved mixing powdered ingredients with dry potassium bromide pellets and applying pressure to form a transparent disk. Each spectrum was scanned 100 times to accurately determine frequencies for specific bands within a range of 0.01 cm-1, achieving a spectral resolution of 4 cm-1²³.

GC-MS analysis:

A gas chromatography-mass spectrometry (GC-MS) analysis was performed following the specified technique. The analysis employed a column temperature of 80°C, an injection temperature of 250°C, a pressure of 108.0 KPa, a total flow rate of 6.2ml/min, and a linear velocity of 46.3cm/s. The compounds were identified by comparing their molecular weight, formula, and retention time with known compounds in the library data using Shimadzu software. This approach guaranteed accurate and dependable compound identification^24-26.

RESULTS:

Percentage yield:

The stem-bark of F. sycomorus had a percentage yield of 17.92%, while the leaves had a percentage yield of 17.80% (Table 1).

Table 1: Percentage yield and physical characteristic of the methanol extract of F. sycomorus stem-bark and leaves

Plant	Sample (g)	Weight of extract (g)	yield (%)	color	Texture
Stem bark	300	53.78	17.92	brownish	crystalline
Leaves	290	51.75	17.80	brownish	crystalline

Phytochemical screening:

Qualitative screening:

Qualitative analysis showed presence of alkaloid, anthocyanins, anthraquinones, cardiac glycoside, chalcone, coumarins, flavonoid, quinine, saponin, tanins and terpenoids while the leaves indicated the presence of alkaloid, anthocyanins, cardiac glycoside, flavonoid, flavonones and flavonols, phenols, phytosterols, quinine, saponin, tanins and terpenoids (Table 2).

Table 2: Qualitative Phytochemicals screening of methanol extract of F. sycomorus stem bark and leaves

Phytochemicals	Stem bark	Leaves
Alkaloid	+	+
Anthocyanins	+	+
Anthraquinones	+	–
Cardiac glycoside	+	+
Chalcone	+	–
Coumarins	+	–
Flavonoid	+	+
Flavonols and flavonones	–	+
Phenols	–	+
Phlobatannins	–	–
Phytosterols	–	+
Quinine	+	+
Saponin	+	+
Tannins	+	+
Terpenoids	+	+

(+) Indicates the presence of Phytochemicals, (-) Indicates the absence of Phytochemicals

Quantitative analysis:

The quantitative test gave concentration in mg/g of the following from stem-bark and leaves respectively; Alkaloid; 36.880±0.2500 and 313.497±1.528, Anthraquinones; 0.001±0.000 and 0.081±0.000, cardiac glycoside; 1.552±0.269 and 11.467±0.197, Flavonoid; 3.650±0.220 and 3.139±4.106, phenolics; 17.380±1.258 and 106.207±92.528, saponins; 0.174±0.000 and 0.079 ±0.006, and tannins; 46.923±0.186 and 247.547±4.640 (Table 3).

Table 3: Quantitative Phytochemicals of methanol extract of F. sycomorus stem bark and leaves

Phytochemicals		Concentration	(mg/g)
	Stem bark			Leaves
Alkaloid	36.880±0.250			313.497±1.528
Anthraquinones	0.001±0.000			0.081±0.001
Cardiac glycoside	1.552±0.269			11.467±0.197
Flavonoid	3.650±0.220			3.139±4.106
Phenolics	17.380±1.258			106.207±92.528
Saponins	0.174±0.000			0.079 ±0.006
Tannins	46.923±0.186			247.547±4.640

Results are in mean ± standard deviation

FT-IR analysis:

The FT-IR analysis of the stem bark revealed specific functional groups at certain frequencies. At 3238 cm^-1, a N-H stretch bond was observed, indicating the presence of 1,2 amines and amide. Additionally, at 1521 cm^-1, there was an N-O asymmetric stretch, suggesting the presence of a nitro group. The frequency of 1369 cm^-1 corresponded to a C-H rock, indicating the presence of alkanes. A C-N stretch bond with aliphatic amines was observed at 1249 cm^-1, and at 821 cm^-1, a C-Cl bond indicated the presence of an alkyl halides functional group (as shown in Table 4).

In the case of the leaves, the FT-IR analysis revealed functional groups at different frequencies. At 3238 cm^-1, an O-H, H bond was observed, suggesting the presence of alcohols and phenol functional groups. At 1607 cm-1, a C=C bond indicated the presence of an alkene functional group. The frequency of 2117 cm-1 corresponded to an HC≡C-CH bond, suggesting the presence of alkynes. At 1526 cm^-1, a C-N bond indicated the presence of aliphatic amines, while at 1048 cm^-1, an N=O bond indicated the presence of nitro groups (as shown in Table 5).

Table 4: Probable functional groups obtained from the FT-IR analysis of F. sycomorus stem bark and leaves

Absorption Ranges	Frequencies (CM^-1)	Bond Types	Functional group
Stem bark extract
3400-3250	3238	N-H stretch	1◦, 2◦ amines, amides
1550-1475	1521	N-O asymmetric stretch	Nitro compound
1370-1350	1369	C-H rock	Alkanes
1250-1020	1249	C-N stretch	Aliphatic amines
850-550	821	C-CL	Alkyl halides
Leaves extract
3200-3500	3238	O-H, H- bonded	Alcohols, phenol
1600-1675	1607	C=C propene	Alkene
2100-2260	2117	HC≡C-CH	Alkynes
1020-1050	1048	C-N	Aliphatic amines
1500-1600	1526	N=O	Nitro groups

Figure 1: FT-IR of F. sycomorus stem bark

Figure 2: FT-IR of F. sycomorus leaves

GC-MS analysis:

The GC-MS analysis of the stem bark revealed the probable presence of various compounds at specific retention times and with specified areas. These compounds include isobutyl amine, propenamide, sucrose, pologalitol, amyl nitrite, glucose, 3-methylheptyl acetate, undecanoic acid, methoxy ethane, methyl guanidine, and acetic acid aminooxy (as shown in Table 6).

On the other hand, the GC-MS analysis of the leaves indicated the presence of different compounds. These compounds included guanidine methyl, aminoacetonitrile, propanamide, amyl nitrate, urea, pentanoic acid, 4-methyl carbonyl sulfide, methanamine, N-hydroxy-N-methyl 2-propenamides, acetic acid, and benzaldehyde-2-nitroso (as shown in Table 7).

Table 6: Probable peaks obtained from the GC-MS analysis of F. sycomorus stem bark

S. No	Retention time	Area	Library/ID
1	75.707	0.96	isobutyl amine
2	81.030	1.69	propanamide
3	83.270	3.09	sucrose
4	83.752	1.70	pologalitol
5	84.919	2.90	amyl nitrite
6	85.242	1.89	glucose
7	88.191	0.92	3-meyhylheptyl acetate
8	90.708	1.77	undecanoic acid
9	93.214	4.09	methoxy ethane
10	94.404	1.74	methyl guanidine
11	96.792	1.65	acetic acid aminooxy

Table 7: Probable peaks obtained from the GC-MS analysis of F. sycomorus leaves

S. No	Retention time	Area	Library/ID
1	92.123	2.49	Guanidine methyl
2	68.602	5.14	Aminoacetonitrile
3	93.582	3.64	Propanamide
4	39.714	3.4	Amyl nitrate
5	39.339	3.28	Urea
6	83.729	6.93	Pentanoic acid, 4-methyl
7	60.779	2.95	Carbonyl sulfide
8	71.51	3.26	Methanamine, N-hydroxy-N-methyl
9	55.116	2.51	2-propenamides
10	75.211	1.62	Acetic acid
11	90.618	1.14	benzaldehyde-2-nitroso

Figure 3: GC-MS of F. sycomorus stem bark

Figure 4: GC-MS of F. sycomorus leaves

DISCUSSION:

The brownish crystalline extract obtained from the dried aqueous methanolic extracts of F. sycomorus stem bark and leaves had a yield percentage of 17.92% and 17.80%, respectively. As shown in Table 2, a qualitative phytochemical investigation has revealed the presence of eleven (11) noteworthy phytochemicals in the stem bark and leaves. Rich constituents such as alkaloids, anthocyanins, anthraquinones, cardiac glycosides, chalcones, coumarins, flavonoids, quinine, saponins, tannins, and terpenoids are all present in the stem bark. Alkaloids, anthocyanins, cardiac glycosides, flavonoids, flavonones, flavonols, phenols, phytosterols, quinine, saponins, tannins, and terpenoids are just a few of the phytochemicals that are abundant in the leaves (refer to Tables 4 and 5). It is clear that F. sycomorus has enormous phytochemical reserves in both its stem bark and leaves.Upon closer examination, certain distinctions between the stem bark and leaves emerge. The stem bark lacks flavonols, flavones, phenols, and phytosterols, which are abundantly present in the leaves. On the other hand, the leaves are devoid of anthraquinones, chalcones, and coumarins, which are prominently found in the stem bark. Interestingly, both the stem bark and leaves do not contain phlobatannins. This significant finding provides valuable insights into which parts of the plant should be targeted for further studies regarding the quantity and isolation of each phytochemical.

The yield of flavonoids from the extract of stem bark and leaves was 3.65mg/g and 3.139mg/g, respectively, suggesting a nearly comparable amount. The health benefits of flavonoids, which have different phenolic structures, are well known. Flavonoids are now essential parts of many pharmacological, cosmetic, nutraceutical, and medical uses. They have become more important because to their remarkable qualities, which include antioxidative, anti-inflammatory, anti-mutagenic, and anti-carcinogenic qualities, as well as their capacity to modify important cellular enzyme performance.

Anthraquinone compounds, mostly found in fruits, stems, vegetables and leaves, were also examined in this study. Stem bark yielded 0.001mg/g of anthraquinone, whereas the leaves exhibited a significantly higher quantity of 0.081mg/g. This disparity may be attributed to the high presence of chlorophylls in the leaves. While traditionally they are used for their anti-inflammatory properties, the in vivo anti-inflammatory activity and molecular mechanisms of anthraquinones remain partially elucidated²⁷.

Moving on to cardiac glycosides, which are widely employed to represent a diverse range of steroid derivatives known for their ability to enhance the force of myocardial contraction and elicit distinct electrophysiological effects.

The application of FT-IR analysis revealed an array of functional groups, each characterized by its unique vibrational patterns. Among these groups were the presence of alkanes, alkyl halides, and aliphatic amines, evoking a sense of chemical richness and complexity.

Additionally, the utilization of GC-MS further unveiled a fascinating spectrum of compounds within the sample. Compounds such as isobutylamine, propanamide, sucrose, pologalitol, amyl nitrite, glucose, 3-methylheptyl acetate, undecanoic acid, methoxyethane, methyl guanidine, and acetic acid aminooxy were detected. Notably, several of these compounds exhibit remarkable therapeutic activities. For instance, methyl guanidine has been renowned for its potent anti-inflammatory effects. Recent evidence suggests that methyl guanidine significantly inhibits iNOS activity and TNF-release, offering potential therapeutic implications²⁸.

An key enzyme involved in the generation of nitric oxide (NO), inducible nitric oxide synthase (iNOS) is crucial for the regulation of blood pressure, inflammation, infection, and the development and progression of malignant illnesses, among other physiological situations²⁹. Superfluous nitrous oxide generation has been associated with tissue injury and organ dysfunction, including the hypotensive and vasoplegic states typical of septic shock. In pathological circumstances, iNOS is regarded as a detrimental enzyme and has been suggested as a primary cause of cardiovascular disorders like atherosclerosis³⁰.

Tumor necrosis factor (TNF), a protein involved in inflammation and immune response coordination, can have both beneficial and detrimental effects depending on the context. While high levels of TNF can signify inflammation and aid in healing processes, they can also lead to unpleasant symptoms such as low blood pressure, fever, muscle aches, and loss of appetite. Methyl guanidine has been shown to attenuate inflammation and tissue damage associated with endotoxic shock, demonstrating its potential therapeutic value in regulating TNF levels³¹.

Undecanoic acid, another compound detected in the analysis, has been reported as an active ingredient in medications for treating skin infections. It possesses properties that alleviate itching, burning, and irritation commonly associated with various skin problems, including fungal infections like athlete's foot and ringworm³². Amyl nitrite, on the other hand, finds medical application in the treatment of heart disease and angina. Additionally, it serves as an antidote for cyanide poisoning³³.

The FTIR results showcasing various functional groups align remarkably well with the compounds identified in the GCMS analysis. Noteworthy correlations can be observed, such as the presence of nitro compounds corresponding to amyl nitrite in the FTIR results, the presence of alkanes coinciding with glucose, and aliphatic amines resonating with methyl guanidine. This striking connection between the results highlights a certain degree of certainty and strengthens the reliability of the findings.

CONCLUSION:

This study concludes that a wide range of phytochemicals, including alkaloids, anthocyanins, cardiac glycosides, flavonoids, phenolics, saponins, tannins, and terpenoids, are present in the stem bark and leaves of F. sycomorus. Flavonoids are important for generating health benefits, as evidenced by their comparable yields. By emphasizing molecules with potential therapeutic applications, including anti-inflammatory, anesthetic, and antibacterial capabilities, the application of FT-IR and GC-MS techniques offered insightful information about the complex chemical composition. The findings' dependability is increased by the correlation that was found between functional groups and chemicals. As a result of this study's emphasis on the beneficial medical qualities of F. sycomorus, more investigation is necessary to determine the species' abundance, isolation techniques, and its uses in medicine. This could reveal novel therapeutic compounds.

CONFLICT OF INTEREST:

The authors have no conflicts of interest regarding this investigation.

ACKNOWLEDGEMENT:

The authors would like to thank the department of Biochemistry, Kano state university of science and technology, Wudil, Kano, Nigeria.

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Received on 07.12.2023 Modified on 16.03.2024

Research J. Pharm. and Tech 2024; 17(7):3134-3140.

DOI: 10.52711/0974-360X.2024.00490