PHYTOCHEMICAL SCREENING, FUNCTIONAL GROUPS IDENTIFICATION BY FT-IR AND GC-MS ANYALYSIS OF CLERODENDRUM INFORTUNATUM L. LEAVES EXTRACT

PHYTOCHEMICAL SCREENING, FUNCTIONAL GROUPS IDENTIFICATION BY FT-IR AND GC-MS ANYALYSIS OF CLERODENDRUM INFORTUNATUM L. LEAVES EXTRACT

G. V. More, R. P. Limsay *, A. P. Somkuwar, S. A. Dubey and S. P. Mandhale

Department of Veterinary Pharmacology and Toxicology, Nagpur Veterinary College, MAFSU, Nagpur, Maharashtra, India.

ABSTRACT: The present investigation focuses on analysis of the active compounds present in the Clerodendrum infortunatum L. leaves extract of different solvents as Petroleum ether and methanol with help of the advance tools like GC-MS and FTIR which posses different pharmacological activities like wound healing, anti-inflammatory, anyalgesic, etc. The leaves were treated with petroleum ether followed by a 50% methanolic extract. The extractability percentage of the petroleum extract was 5.71%, whereas the methanolic extract had a value of 21.88%. The phytochemical study of extracts indicated the presence of alkaloids, glycosides, carbohydrates, phytosterol, phenolic compounds, tannins, and flavonoids. Fourier Transform Infrared Spectroscopy (FT-IR) analysis revealed functional groups of phenols, alcohols, alkane, carboxylic acids, and their esters, as well as primary amines and proteins in both 50% methanolic and petroleum ether extract. GC-MS analysis revealed presence of 51 compounds in petroleum ether and 27 compounds in 50% methanolic extract.

Keywords: Clerodendrum infortunatum L., GC-MS, FTIR, Flavonoids., etc

INTRODUCTION: It is being increasingly recognized that ethnopharmacology, which largely uses natural materials such as herbs and minerals, can contribute as a discovery engine to provide new leads and also offer quality-assured and standardized traditional medicines. There is a clear movement to build a golden triangle between traditional medicine, modern medicine, and modern science ¹⁷. Since, ancient times, people in India have treated different diseases and wounds with natural substances derived from plants. This practice is known as Ayurveda, a popular branch of Indian medicine.

Natural goods have been utilized for generations in many regions of the world; because of their relatively low side effects, natural products are starting to gain the same importance as alternative medicine. For these reasons, scientific research is being done on traditional and natural remedies to improve animal health. For the purpose of treating chronic illnesses, they are used directly as drugs in their crude or raw form ⁵.

FIG. 1: THE PLANT CLERODENDRUM INFORTUNATUM

Pharmacological research on Clerodendrum infortunatum L. shows that this plant has enormous promise for treating a wide range of ailments, including diabetes, malaria, coughs, wounds, and inflammation. Additionally, Clerodendrum infor-tunatum L. demonstrates anti-inflammatory, antibacterial, antioxidant, anti-diabetic, wound-healing, anti-venom, and anti-fertility properties ²⁵.

A vast genus of flowering plants, including herbs, shrubs, and small trees, Clerodendrum is a member of the Lamiaceae family and is found worldwide in tropical climates. For the first time, Linnaeus described the genus. Butterflies and hummingbirds frequent the plant blooms, while certain insect larvae eat specific types of Clero-dendrum. Numerous species of the genus have been used in traditional medicine across multiple nations. The pharmacological characteristics and phytochemical content of a select few species have been thoroughly investigated. Clerodendrum species have shown pharmacological qualities such as antibacterial, anticancer, antimalarial, antioxidant, antidiabetic, larvicidal, and antidiarrheal activity ²⁶.

The plant Clerodendrum infortunatum is known as Bhandir in Sanskrit and an old Sanskrit verse; describe its use in fever, skin diseases, rheumatoid arthritis, worm infestation, diabetes, bleeding disorders, etc ¹. The phytochemical analysis revealed the presence of alkaloids, carbohydrates, glycosides, amino acids, phytosterol, phenolic compounds, tannins, resins, and flavonoids in the 50% ethanolic and 50% methanolic extracts of C. infortunatum leaves. In dogs, the 10% concentration of methanolic extract ointment of C. infortunatum proved to be more effective than both the ethanolic extract ointment of C. infortunatum and the Povidone Iodine ointment ²⁴. Nowadays, there is a desire to stop the spread of antibiotic resistance and the growing importance of the health economy has a significant impact on the development of topical medications for wound healing. Topical medications need ways to guarantee that the active ingredient is sufficiently bioavailable inside the wound, such as on-site production and/or decreased degradation. In industrialized nations, chronic, non-healing skin lesions account for more than 3% of healthcare spending, and their frequency is on the rise. Two concurrent themes are now influencing advancements in the field of wound healing: the desire to stop the spread of antibiotic resistance and the growing use of value-based and health economics models. The development of new drugs that try to speed up wound healing frequently draws inspiration from the past. For example, plants that were traditionally used in Ayurvedic medicine to treat wounds are now being scientifically evaluated for medicinal ingredients, but those ingredients are now available in clinics ¹⁹.

MATERIALS AND METHODS:

Collection and Authentication of Plant Material and Preparation of Extracts: C. infortunatum leaves were procured from region of Wardha, Nagpur and Go- Vigyan Anushandhan Kendra, Devlapar, Nagpur. The collected plant material was identified as Clerodendrum infortunatum by the expert botanists of Department of Botany, Rashtrasant Tukdoji Maharaj Nagpur University (RTMNU), Nagpur. The authenticated herbarium sheet with voucher specimen number (261, 02/12/2023).

Properly cleaned, dried, and powdered leaves of the Clerodendrum infortunatum plant were subjected to extraction as per the method described by Sheel ²⁵. The accurately weighed powder was first defatted with petroleum ether in jumbo Soxhlet’s apparatus at approximately 80°C. The defatted leaf powder of the plant material was air dried and further subjected to 50% methanolic extraction (50 parts methanol with 50 parts distilled water) to obtain the desired fraction or extraction. For later usage, the extract was collected on clean, sterile pre-weighed petri plates and kept in an airtight desiccator for further use.

The percent extractability of extract was determined with following formula:

% Extractability = Weight of extract (gm) / Weight of powder used (gm) × 100

Qualitative Phytochemical Analysis, GC-MS analysis and (FT-IR) analysis of the Extracts: To determine the presence or absence of various phytoconstituents, the ethanolic and methanolic extracts of Clerodendrum infortunatum were subjected to a preliminary qualitative phytochemical examination using the technique outlined by ^{8, 27, 28}. The characteristics of functional groups in 50% hydromethanolic and petroleum ether extract of the leaf of C. infortunatum were identified using an FTIR spectrophotometer. It provides information about the structure of a molecule that could frequently be obtained from its absorption spectrum. 10 mg of plant extracts of the leaf were taken in a KBr vessel and placed in a sample cup of a diffuse reflectance accessory. A small quantity of the C. infortunatum extracts was mixed in dry potassium bromide (KBr). The mixture was thoroughly mixed in a mortar and pressed at a pressure of 6 bars within 2 min to form a KBr thin disc. Then the disc was placed in a sample cup of a diffuse reflectance accessory BRUKER, Alpha II, FT-IR spectrophotometer was used to identify the functional group available in the extracts. The leaf extracts of C. infortunatum were scanned from 400 to 4000 cm⁻¹ for 16 times to increase the signal-to-noise ratio. The peak values of the FTIR were recorded. The GC-MS analysis of extracts of leaves of C. infortunatum was carried out using SHIMADZU GCMS-QP2020 with a quadra pol 2020 MS detector. The capillary column was GCMS-QP2020   (30 m   250 µm   0.25 µm) composed of 5% phenyl methyl silox. The initial oven temperature was 40ºC for 1 minute which was raised at a rate of 20ºC/min up to 150ºC for 1 minute and then at a rate of 3ºC/min up to 280ºC for a hold time of 10 min. The injector volume was 4 µl. The gas was used as the carrier with a constant flow rate with a split ratio of 25:0. The MS operating conditions were; source temperature of 230ºC (max 250ºC), quad temperature of 150ºC (max 200ºC), solvent delay time of 3 min. Compounds were identified in terms of RT values and mass spectra with those obtained from the NIST search library. The obtained compounds were searched for detailed information.

RESULTS AND DISCUSSION:

Extraction Details: The leaves of Clerodendrum infortunatum were shade-dried, crushed, and defatted with petroleum ether and being extracted with Soxhlet's apparatus for 50% methanol. Table 1 shows the extract's physicochemical properties and extractability percentage.

TABLE 1:  EXTRACTABILITY PERCENTAGE AND PHYSICAL CHARACTERS OF PETROLEUM ETHER AND 50% METHANOLIC EXTRACT OF CLERODENDRUM INFORTUNATUM LEAVES

In the current investigation, the percentage extractability of petroleum ether and 50% methanolic extract was 5.71% and 21.88%, respectively. They found 4.8% and 5.46% extractability in a petroleum ether extract of C. infortunatum leaves ^{2, 9}. Similarly, Das, Prabhu and Baid showed extractability percentages of 13.50%, 17.07%, 15.55%, and 7.04% for various concentrations of methanolic extracts of C. infortunatum leaves ^{6, 24, 2}.

Qualitative Phytochemical Analysis of Petroleum Ether and 50% Methanolic Extract: A preliminary qualitative phytochemical analysis of the petroleum ether and 50% methanolic extracts of Clerodendrum infortunatum leaves was carried out. Table 2 shows the findings obtained when determining the presence of particular phytoconstituents and active principles.

TABLE 2: QUALITATIVE PHYTOCHEMICAL ANALYSIS OF PETROLEUM ETHER AND 50% METHANOLIC EXTRACT OF LEAVES OF CLERODENDRUM INFORTUNATUM

Preliminary phytochemical analysis of a petroleum ether extract of leaves revealed the presence of carbohydrates, flavonoids, glycosides, phytosterol, resins, fixed oils, and fats, while 50% methanolic extracts of C. infortunatum leaves revealed the presence of alkaloids, carbohydrates, glycosides, amino acids, phytosterol, phenolic compounds, tannins, resins, and flavonoids. Sheel, and Ram found alkaloids, steroids, flavonoids, carbohydrates, and tannins in a methanolic extract of C. infortunatum. In a broader sense, phytochemistry is concerned with the vast array of organic compounds that plants create and accumulate ^{24, 25}. Medicinal herbs have therapeutic qualities because they contain various complex chemical compounds with diverse compositions that occur as secondary plant metabolites in one or more parts of these plants ²⁰. Preliminary phytochemical investigation of different extracts of leaves of C. infortunatum L. shows the presence of sterols, carbohydrates, tannins, terpenoids, flavonoids, and saponin indicating the plant is a prominent model for various types of pharmacological activity ³¹.

Fourier Transform Infrared Spectroscopy (FT-IR) Analysis of Extracts: FTIR is a powerful versatile and non-destructive analytical technique used for the chemical characterization of different compounds and can provide fundamental information on the molecular structure of organic compounds in plant extracts. The infrared spectrum of gallic acid, quercetin, rutin, and tannic acid in the frequency range of 4000–400 cm⁻¹ was obtained to identify the characteristic absorption peaks corresponding to stretching vibrations of different functional groups are shown in Fig. and Fig. The IR spectrum petroleum ether and 50% methanolic extract displayed different peaks corresponding to different functional groups present in C. infortunatum in Table 3 and 4.

FIG. 2: FT-IR SPECTRA OF PETROLEUM EXTRACT OF CLERODENDRUM INFORTUNATUM

FIG. 3: FT-IR SPECTRA OF 50% METHANOLIC EXTRACT OF CLERODENDRUM INFORTUNATUM

TABLE 3: ALL POTENTIAL BANDS, CORRESPONDING FUNCTIONAL GROUPS, AND POSSIBLE COMPOUNDS IDENTIFIED IN THE PETROLEUM ETHER EXTRACT OF THE FORMULATION USING FT-IR SPECTROSCOPY

TABLE 4: ALL POTENTIAL BANDS, CORRESPONDING FUNCTIONAL GROUPS, AND POSSIBLE COMPOUNDS IDENTIFIED IN THE 50% METHANOLIC EXTRACT OF THE FORMULATION USING FT-IR SPECTROSCOPY

The current FT-IR investigation petroleum ether and 50% methanolic extracts revealed presence of functional groups like Alcohol (O-H), Alkane (C-H), Aliphatic ketone (C=O), Carbonyl (C=O), Amide (N-H), Nitro (N-O), Alkene (=C-H) and Alcohol (O-H), Alkane (C-H), Carbonyl (C=O), Amide (R ( C = O ) N R 1 R), Nitro (N-O), Aromatic (C=C), Alkene (=C-H) resp. At different frequencies. FTIR bands in the 4000-1500 cm⁻¹ range identified functional groups, whereas high absorption bands in the 1500-500 cm^-1 area identified fingerprints. The O-H and C-H stretching frequencies were identified in the 3700-2500 cm⁻¹ range, whereas the C-H stretching vibration occurred in the 2900-2800 cm⁻¹ region, which corresponded to the fingerprint region ⁷. 21 O-H and C-H stretching frequencies occur between 3700 and 2500 cm⁻¹, ²¹ whereas C-H stretching vibrations occur between 2900 and 2800 cm⁻¹. Thus, FTIR was utilized to determine the functional groups contained in various phytochemicals in plant samples.

The peak at 1734-1745 cm⁻¹ was identified as C=O ester and may be connected to pheophytin and chlorophyll. In this investigation, the peak was at 1743 cm⁻¹. Carotenoids were anticipated to be present in E. acoroides' dried leaf powder. The FTIR spectrum at 1654 cm⁻¹ indicates the C=O conjugate. The conjugated double bond in carotenoids has been identified as the structure responsible for light absorption. Prior research found that a peak at 1654 cm⁻¹ indicates chlorophyll and protein content ²².

The FTIR spectra of Clitoria ternatea leaf extract indicated the existence of phenols and alcohols, with peaks at 3389.57 cm^-1 representing the hydroxyl and O-H bonding frequencies, respectively. The peaks at 2925.41 cm^-1 and 2856.66 cm^-1 are ascribed to C-H stretching, indicating the presence of certain alkene compounds. The peak value of 1632.33 cm^-1 indicates primary amines. The peak value of 1409.06 cm^-1 indicates aromatic amines. The peak value at 1057.61 cm^-1 verifies aliphatic amines, 926.50 cm^-1 confirms carboxylic acids, and 869.00 cm^-1 confirms primary and secondary amines ¹⁴.

Gas Chromatography- Mass Spectrophotometry (GC-MS) Analysis: GC-MS is one of the most reliable biophysical methods for phytochemical profiling and the plant C. infortunatum showed the presence of several bioactive phytoconstituents like Octadecane, hexadecanoic acid, ecosinane, etc. When different parts of the plant are analyzed with GC-MS technique ^3, 11.

In the present study, the GC-MS analysis of 50% methanolic extract of C. infortunatum leaves revealed the presence of a total of 27 active phytocostitutes. The details of the compounds along with their synonyms, chemical formula, molecular weight, retention time, Peak Height, and area percentage (%) are listed in Table 5 and 6, its chromatogram is depicted in Fig. 4 and 5.

TABLE 5: DETAILS OF THE ACTIVE PRINCIPLES FOUND IN GC-MS ANALYSIS OF THE 50% METHANOLIC EXTRACT OF C. INFORTUNATUM LEAVES

TABLE 6: DETAILS OF THE ACTIVE PRINCIPLES FOUND IN GC-MS ANALYSIS OF THE PETROLEUM ETHER EXTRACT OF C. INFORTUNATUM LEAVES

Previous GC-MS investigations of the methanolic extracts of the leaves of Clerodendrum spp. reported many similar phytoconstituents in the plant, such as Octacosane, 2-methy, Eicosane, Neophytadiene, Hexadecane, 2,4-Di-tert-butylphen, Tridecane, 1-iodo, 3Oxatricyclo [3.2.1.0(2,4)] Octane. The GC-MS analysis revealed 16 peaks of several phytoconstituents, including acetamide, N, N-carbonyl bis-, 4Pyranone, 2,3-dihydro-, alpha-D-Galactofuranoside, methyl 2,3,5,6-tetra-Omethyl-, glycerin, xylitol, N, N-Dimethylglycine, 4H-Pyran-4-one, 2, 3-dihydro-3,5-dihydroxy-6-methyl-, Benzofuran,2,3-dihydro-,5-Hydroxymethylfurfural, 2(1H) Pyrimidinone, 1-methyl-,2, 4-Dihydroxy-5,6-dimethylpyrimidine, 3-Deoxyd-mannoic lactone, 1, 3-Methylene-d-arabitol, Orcinol, n-Hexadecanoic acid, Phenol,4,4'-(1-methyl ethylidene), etc ^{8, 18}.

FIG. 4: CHROMATOGRAM OF GC-MS SPECTRA OF 50% METHANOLIC EXTRACT OF CLERODENDRUM INFORTUNATUM

FIG. 5: CHROMATOGRAM OF GC-MS SPECTRA OF PETEROLEUM EXTRACT OF CLERODENDRUM INFORTUNATUM

Earlier phytochemical studies of Clerodendrum infortunatum revealed the presence of Terpenoid compounds (Clerodolone, Clerodone, Clerodol ¹⁶. In the Clerodendrum genus, the main chemical elements are phenolic compounds (acetone, methyl, and ethyl ester of caffeic acid), steroids (clerodolone, clerodole, sterol Clerosterol), and fixed oil glycerides of linolenic, oleic, stearic, and lignoceric acid ²³.

Plant furans have been linked to a variety of medicinal qualities, including anticancer, analgesic, anti-inflammatory, antibacterial, and anti-histaminic effects. Furans are heterocyclic chemicals found in many therapeutic medicines. Furan containing compounds are pharmacologically active and hence appear in a wide range of medicinal products ⁵. The plant P. zeyplanica (Chitra moalam) has several medicinal qualities, including anti-inflammatory, antiatherosclerotic, and antimicrobial action. The phytoconstituent heneicosane was isolated from the plant and suspected of having antibacterial and antifungal properties. Heneicosane displayed excellent antibacterial and antifungal efficacy at all doses ²⁹.

Medicinal herbs have therapeutic capabilities because they include a variety of chemical substances of varying compositions that are found as secondary plant metabolites in one or more portions of the plant. In a larger sense, phytochemistry is concerned with the great variety of organic substances produced and stored by plants ¹⁵.

Many phytoconstituents discovered in GC-MS analysis of extracts of C. infortunatum in this work were previously reported for varied pharmacological activities, such as 1,2 cyclop-nentanedione, which exhibits high antioxidant action ¹². 2-Methoxy-4-Vinylphenol reduces inflammation in wound healing by inhibiting NF-B and MAPK (Mitogen-Activated Protein Kinase) activation ¹⁰. Earlier literature clearly reveals that flavonoids are the major class of compounds that are mainly present in Clerodendrum species. Some of the major flavonoids present in the genus are cynaroside, 5 – hydroxyl – 4 – 7 – dimethoxy -methylflavone, kaempferol, salvigenin, 4-methyl scutellarein, 5,7,4-O-trihydroxyflavone, apigenin, luteolin, acacetin-7-O-glucuronide, hispidulin, 2-4-4trihydroxy 6-methyl chalcone, 7-hydroxy flavone, luteolin, naringin-4-O-glucopyranoside, pectolin-arigenin, cirsimaritin, cirsimaritin-4glucoside, quercetin-3-methyl ether which were isolated from C. inerme, C. phlomidis, C. petasites, C. trichotomum, C. mandarinorum and C. infortunatum ²⁶. The petroleum ether extract of Clerodendrum phlomidis had shown in GC-MS spectral studies the presence of three compounds are as follows: (1) Isopropyl Linoneate, (2) Hexadecanoic Acid, 2Hydroxyl-1-[Hydroxymethyl]Ethyl Ester, (3) 9-Octadecenoic Acid [Z]-, 2-Hydroxy-1-[Hydroxymethyl] EthylEster ³.

As reviewed more than 300 chemical constituents that had been isolated and identified from the genus of Clerodendrum, cataloged as 58 diterpenoids, 43 flavonoid and flavonoid glycosides, 40 phenylethanoid glycosides, 43 steroids, and steroid glycosides, 31 triterpenoids, 27 monoterpene and its derivatives, 13 cyclohexylethanoids, 4 anthraquinones, 3 sesquiterpene, 2 cyanogenic glycosides, and pharmacological studies indicated that the crude extracts and some special monomer compounds of the genus Clerodendrum exert various biological activities, such as anti-inflammatory and anti-nociceptive, antioxidant, anticancer, antimicrobial, antihypertensive, anti-obesity, anti-diarrheal, hepatoprotective, memory enhancing, and neuroprotective activities.

Terpenes, including monoterpene and its derivatives, sesquiterpene, diterpenoids, and triterpenoids, as the major characteristic constituents with significant biological activities, have great potential to be developed into new drugs, especially for anti-inflammatory, antioxidant, anticancer, and antimicrobial agents. In addition, important activities, such as anti-hypertensive, anti-obesity, and hepatoprotective activities indicated that the Clerodendrum genus can be a promising source of biologically active compounds for these diseases ³¹. Morpholine Derivatives gives a general overview of the various synthetic leads that contain the morpholine ring. It also covers the most effective molecules in each group and uses structure-activity relationship (SAR) to identify the active pharmacophores responsible for the antitubercular, antihyper-lipidemic, antiviral, anticancer, antioxidant, antimicrobial, and antileishmanial properties. The presence of morpholine nucleus as an active pharmacophore in this sizable pool of marketed medications illustrates the importance of morpholine in drug development ¹³. As GC-MS analysis of petroleum ether extract has detected Morpholin-3-one, 2-hydroxy-2,5,5-trimethyl at retention time 5.185 min contains Morpholine nucleus with N-H and -O- as functional group which possess anti-inflammatory and analgesic activity. FT-IR analysis shows the presence of phenols, carboxyl acids, alcohols, alkenes, and alkynes supports the qualitative analysis of extract as well as GC-MS analysis and their compounds also support the wound healing potential of the C. infortunatum extract formulations in cattle.

CONCULSION: The petroleum ether and 50% methanolic extracts of C. infortunatum abundantly possess several pharmacologically active phytoconstituents like flavonoids, tannins, etc. as supported by the preliminary qualitative phytochemical investigation and FT-IR and GC-MS analysis. As a result, the present study revealed the presence of bioactive phytoconstituents found in plant extracts when subjected to preliminary phytochemistry, detailed GC-MS, and FT-IR analysis.

ACKNOWLEDGEMENT: The authors are highly thankful to the Nagpur Veterinary College, MAFSU, Nagpur for providing necessary facilities for this work and are also thankful to RTMNU, Nagpur for their cooperation during the studies.

CONFLICTS OF INTEREST: The authors declare that there are no conflicts of interest.

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    How to cite this article:

    More GV, Limsay RP, Somkuwar AP, Dubey SA and Mandhale SP: Phytochemical screening, functional groups identification by FT-IR and GC-MS anyalysis of Clerodendrum infortunatum l. leaves extract. Int J Pharm Sci & Res 2024; 15(11): 3273-83. doi: 10.13040/IJPSR.0975-8232.15(11).3273-83.

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