TECOMELLA UNDULATA (SM.) SEEM.- GC-MS ANALYSIS OF FLAVONOIDS AND INHIBITORY ACTIVITY AGAINST PATHOGENIC MICROBES

TECOMELLA UNDULATA (SM.) SEEM.- GC-MS ANALYSIS OF FLAVONOIDS AND INHIBITORY ACTIVITY AGAINST PATHOGENIC MICROBES

Richa Bhardwaj ^{* 1} and R. A. Sharma ²

Department of Botany ¹, IIS University, Jaipur - 302020, Rajasthan, India.

Department of Botany ², University of Rajasthan, Jaipur - 302007, Rajasthan, India.

ABSTRACT: Tecomella undulata (Sm.) seem is a monotypic genus belonging to family Bignoniaceae. The plant holds the tremendous potential of medicinal value and has been traditionally used in various ailments like syphilis, leukoderma, blood disorders, to name a few. The plant has gained prominence due to the presence of some prominent secondary metabolites. The present study focuses on the GC-MS analysis of extracts of all the plant parts of T. undulata, which revealed the presence of certain bioactive compounds like Quericitin, Kaempferol, stigmasterol, sitosterol, thiazoline, phytol, pthalic acid, methyl alpha ketopalmitate and so forth. A total of about 20 bioactive compounds were identified. The antimicrobial activity of the extracts was assayed against pathogenic bacteria and fungi. The flavonoids from leaf extracts showed highest antimicrobial activity against C. albicans, S. aureus, E. coli, and B. subtilis. This also correlates with the highest amount of Flavonoids present in leaves followed by the amount present in roots. The study thus infers that the presence of bioactive components may be the principle behind the antimicrobial property of different plant parts, and therefore Tecomella forms a potential plant for herbal drug formulation.

Tecomella undulata, Bioactive compounds, GC-MS, Antimicrobial activity

INTRODUCTION: Awareness of medicinal plant usage is a result of the many years of struggles against illnesses due to which man learned to pursue drugs in barks, seeds, fruit bodies, and other parts of the plants. A natural product is a chemical compound or substance produced by a living organism like microorganisms, marine organisms, animal sources, plant sources. The definition of natural products is usually restricted to mean purified organic compounds isolated from natural sources that are produced by the pathways of primary or secondary metabolism.

The importance of medicinal plants in traditional healthcare practices has provided clues to new areas of research and in biodiversity conservation is now well recognized ^{1, 2}. Many conventional drugs originate from plant sources, the emergence of new herbal genomics research, medicinal plant genomics consortium, together with advances in other omics information may help for the speedy discovery of previously unknown metabolic pathways and enzymes ³. Because of the absence of an efficient excretory system plant produced secondary metabolites, secondary metabolites include volatile oils, flavonoids, alkaloids, glycosides, tannins, resins etc. that have been successfully exploited for vital sources for food additives, flavors, and industrially important pharmaceuticals ⁴.

The genus Tecomella undulata is a tree species that produce quality timber. In Rajasthan, it is mainly found in western parts distributed in Barmer, Jaisalmer, Jodhpur, Pali, Ajmer, Nagaur, Bikaner, Churu, and Sikar districts. Tecomella undulata belongs to family Bignoniaceae (Jacaranda family). The Bignoniaceae family comprising of about 110 genera and 650 species is a family of flowering plants, commonly known as the Trumpet Creeper family, Jacaranda family, Bignonia family, or the Catalpa family. Roheda is mainly used as a source of timber.  Its wood is strong, tough, and durable, excellent for firewood and charcoal. Roheda plays an important role in ecology. It acts as a soil-binding tree by spreading a network of lateral roots.

The species has been identified as an important factor for environmental conservation in arid zones as a stabilizer of shifting sand dunes, providing shelter for wildlife. It is also a very useful species for afforestation of the drier tracts due to its drought and fire-resistant properties ^{5, 6}. Flavonoids are phenolic substances isolated from a wide range of vascular plants, with over 8000 individual compounds known. A variety of in-vitro and in-vivo experiments have shown that selected flavonoids possess antiallergic, anti-inflammatory, antiviral and antioxidant activities, significant anticancer activity including anticarcinogenic properties, certain flavonoids possess potent inh-ibitory activity against a wide array of enzymes ^{7, 8}.

According to the IUPAC nomenclature, they can be classified into flavonoids or bioflavonoids., iso-flavonoids, derived from 3-phenylchromen-4-one (3-phenyl-1,4-benzopyrone) structure, neoflavo-noids, derived from 4-phenylcoumarine (4-phenyl-1,2-benzopyrone) structure. Three flavonoid classes above are all ketone-containing compounds, and as such, are anthoxanthins (flavones and flavonols). This class was the first to be termed bioflavonoids ^{9, 10}.

MATERIALS AND METHODS:

Plant Material: The different plant parts (roots, stems, leaves, and bark) of Tecomella undulata were collected in the month of October-December from the University of Rajasthan campus. It was washed with tap water, dried at room temperature and ground to a fine powder. The species specimen was submitted to the herbarium, Department of Botany, University of Rajasthan. Jaipur, Rajasthan, India, and got the voucher specimen no. RUBL211300.

Chemicals: All the chemicals used were of analytical grade and purchased from Hi-Media from Hi-media Laboratory Pvt. Ltd. Mumbai.

Tests for Flavonoids:

Shinoda's Test: To 2 ml of the test solution, a fragment of magnesium metal (mg++) ribbon was added into the test tube, followed by the dropwise addition of concentrated conc. HCl. The resulting pink/ scarlet/ crimson of occasionally green/ blue colors indicated the presence of flavonoids ¹¹.

NaOH Tests: To 2-3 ml. of extract, few drops of sodium hydroxide solution were added into a test tube. Formation of intense yellow color that became colorless on the addition of a few drops of dilute HCl indicates the presence of flavonoids ¹².

GC-MS Analysis of Flavonoids:

GC-MS Conditions: GCMS-QP 2010 Plus was used for identification and quantification of phytoconstituents, using MS libraries previously compiled from purchased standards. For the acquisition of an electron ionization mass spectrum, an ion source temperature of 250 °C was used. The GC was equipped with a SE-30 capillary column, a split injection piece (270 °C), and direct GC-MS coupling (280 °C). Helium (1.2 mL/min) was used as the carrier gas with a split ratio of 1:10. The oven temperature program for analyzing the extracts utilized an initial oven temperature of 100 °C, maintained for 2 min, followed by a steady climb to 200 °C at a rate of 7 °C/min allowed to increase to 190 °C at a rate of 30 °C/min. This oven temperature was again maintained at 190 °C for 5 min and then allowed to increase to 300 °C at a rate of 7 °C/min.

This oven temperature was maintained for 2 min and finally ramped to 300 °C at a rate of 10 °C/min and maintained for a further 22 min. Injection temperature was 270 °C and volume 250 °C and 1 μL, respectively. The total GC running time was about 43.28 min. The MS operating conditions were as follows, Interference temperature of 260 °C, Ion source temperature of 250 °C, mass scan (m/z)-40-450, solvent cut time 7 min, scan speed 2000 amu/s total MS running time-50.28 min and Threshold -1000.

Identification: GC-MS is a valuable aid for identifying unknown peaks as well as for confirming the identification of identified phytoconstituents. In some cases, when no identical spectra were found, the structural type of the corresponding component was suggested only on the basis of its mass spectral fragmentation and retention data. Identification of components was based on directs comparison of the retention times and mass spectral data with those for standard compounds and computer matching with the library (Wiley library, NIST data bank, database NIST 98) as well as by comparison of the retention time.

Sources of Test Organisms:

Fungi: The fungal strains Aspergillus niger (NCIM 0616), Fusarium oxysporium (NCIM 1228), Trichoderma reesei (NCIM 0992), Penicillium funiculosum (NCIM 1075), Candida albicans (NCIM- 3501), Trichoderma viride are procured from the National Institute for Complementary Medicine.

Bacteria: The bacterial strains Escherichia coli (MTCC 1652), Staphylococcus aureus (MTCC 0087) (Gram+ve), Pseudomonas aeruginosa (MTCC 4646) (Gram+ve), Bacillus subtilis (MTCC 0121), Klebsiella pneumoniae (MTCC-0109) (Gram–ve) and Streptomyces albudencus (MTCC 1764), Enterococcus faecalis (ATCC- 29212) (gram+ve) were procured from the microbial type culture collection (Institute of Microbial Technology, Chandigarh, India).

Culture of Test Microbes: For the cultivation of bacteria, Nutrient Broth Medium (NB) was prepared using 8% Nutrient Broth (Difco) in distilled water and agar-agar and sterilized at 15 lbs psi for 25-30 min. Agar test plates were prepared by pouring ~15 ml of NBM into the petri dishes (10 mm) under aseptic conditions. A peptone saline solution was prepared (by mixing 3.56 g KH₂PO₄ + 7.23 g NaH₂PO₄ + 4.30 g, NaCl + 1 g peptone in 1000 ml of distilled water, followed by autoclaving) and the bacterial cultures were maintained on this medium by regular sub-culturing and incubation at 37 °C for 24 h. However, for the cultivation of fungi, Potato Dextrose Agar (PDA) medium was prepared by mixing 100 ml potato infusion + 20 g agar + 20 g glucose, followed by autoclaving) and the test fungi were incubated at 27 °C for 48 h and the cultures were maintained on the same medium by regular sub-culturing.

Fungicidal and Bactericidal Assay: For both fungicidal and bactericidal assays agar well diffusion method was adopted ^{13, 14}, because of reproducibility and precision. The different test organism was proceeded separately using a sterile swab over previously sterilized culture medium plates, and the zone of inhibition were measured around wells in solidified medium (5 mm in diameter), which were containing 2mg/ml and 4mg/ml of the test extracts, control solvent or steptomycin (1mg/ml) or ketokenazol (1mg/ml) as reference separately. These plates were initially placed at low temperature for 1 hr, so as to allow the maximum diffusion of the compounds from the wells into the plate and later, incubated at 37 °C for 24 h in case of bacteria and 48 h at 27 °C for fungi, after which the zones of inhibition could be easily observed. Three replicates of each test extract were examined, and the mean values were then referred.

RESULTS AND DISCUSSION: Flavonoids have been reported to be an important constituent of medicinal plants, flavonoids have been assayed for their antioxidant activity ^{15, 16}. Various techniques have been employed for the quantification of flavonoids which include advanced techniques like HPLC RP-HPLC, microwave-assisted extraction ^{17, 18}.

TABLE 1: CHROMATOGRAPHIC DATA AND COLOUR REACTION OF THE FLAVONOIDS ISOLATED FROM TECOMELLA UNDULATA

Abbreviations :BeAW⁺ = Benzene : Acetic acid : Water (125 : 72 : 3); BAW* = n-Butanol : Acetic acid : Water : (4: 1:5); TBA⁺⁺  =  t-Butanol : Acetic acid : Water (3:1:1) BK = Black; BN = Brown; BT = bright, BL = blue, GY = Grey; DL = dull; GN = green; YW = yellow

Isolated flavonoid content in T. undulata is recorded as, amongst the free form of flavonoids extracted, in the plant parts kaempferol was obtained in maximum mount while luteolin is observed in minimum amount. (in roots; kaemp-ferol; 0.12 mg/gdw > quercetin; 0.09 mg/gdw > luteolin; 0.06 mg/gdw), (in stems; kaempferol; 0.09 mg/gdw > quercetin; 0.08 mg/gdw > luteolin; 0.07 mg/gdw), (in Bark; kaempferol; 0.11 mg/gdw > quercetin; 0.07 mg/gdw > luteolin; 0.06 mg/gdw) (in leaves; kaempferol; 0.23 mg/gdw > quercetin; 0.16 mg/gdw > luteolin; 0.13 mg/gdw) maximum amount of total free flavonoids was observed in leaves (leaves; 0.52 mg/gdw > roots; 0.27 mg/gdw stems; 0.24 mg/gdw = Bark; 0.24 mg/gdw).

Amongst the bound form of flavonoids in roots kaempferol was reported in maximum amount while quercetin was observed in minimum amount (kaempferol; 0.08 mg/gdw > quercetin; 0.06 mg/gdw > Luteolin; 0.05 mg/gdw) while in stems and leaves kaempferol was observed in higher amount while Quercetin was observed in lower amount (kaempferol; 0.07 mg/gdw > Luteolin; 0.06 mg/gdw > quercetin; 0.05 mg/gdw) in Bark kaempferol is observed in higher amount while luteolin in lower amount (kaempferol; 0.08 mg/gdw > quercetin; 0.06 mg/gdw > Luteolin; 0.04 mg/gdw) in leaves Quercetin is obserbved to be maximum while luteolin is minimum. (Quercetin; 0.12 mg/gdw > kaempferol; 0.10 mg/gdw > Luteolin; 0.09 mg/gdw). Maximum amount of total bound form of flavonoids was observed in leaves (leaves; 0.31 mg/gdw > root; 0.19 mg/gdw > stems; 0.18 mg/gdw = bark; 0.18 mg/gdw).

The total flavonoid content (F+B) was observed maximum in leaves and minimum in stems (leaves; 0.83 mg/gdw > root; 0.46 mg/gdw > stems; 0.42 mg/gdw = Bark; 0.42 mg/gdw). Other flavonoids have also been reported. Content higher than presently investigated have been reported in various plant parts of Tecomella in earlier studies; similarly, total flavonoid content has also been reported. Leaves and flowers of Tecomella undulata have been shown to have significant antioxidant activity due to the higher content of flavonoids present, the maximum amount of flavonoids are reported in leaves of Tecomella undulata. Accumulation of flavonoids is also affected due to seasonal variations.

TABLE 2: ISOLATED FLAVONOID CONTENT (mg/gdw*) IN TECOMELLA UNDULATA

The eluted compounds from TLC were pooled together according to their TLC behavior and isolate them with the solvents and evaporated yielding three flavonoids kaempferol, quercetin, and luteolin. The spectral analyses of the active constituent, (a) Luteolin (b) quercetin and (c) kaempferol from the different plant parts of Tecomella undulata are shown below: -

Luteolin: yellow needles on crystallization (mp 280° - 320°C).

UV light absorption MeOH: 242 sh, 253 sh, 267 sh, 291 sh, 349 sh.

IR: vcm^–1/ max KBr: 3400, 3423, 3100 (O–H), 1070, 1150, 1010(C=O), 1656, 1620, 1612 (C=C), 1514(aromatic), 1103, 1862, 1839, 1562.

¹HNMR (300MHz, CDCl₃): 3.42, (H₁), 3.49 (H₂), 3.56 (H₃), 6.30 (H₄), 3.68 (H₅), 3.85 (H₆), 5.10 (H₇), 6.63 (H₈), 6.83 (H₉), 6.95(H₁₀), 7.41(H₁₁), 7.43(H₁₂).

¹³C NMR (300MHz, CDCl₃): 122.6 (C₁), 113.8 (C₂), 76.8 (C₃), 70.3 (C₄), 77.4 (C₅), 100.5 (C₆), 163.9 (C₇), 95.8 (C₈), 158.0(C₉), 106.3 (C₁₀), 165.8 (C₁₁), 146.3(C₁₂), 150.4 (C₁₃), 121.1 (C₁₄), 119.0 (C₁₅).

Quercetin: yellowish needles on crystallization (mp 312°-313°C).

UV light absorption MeOH: 255 sh, 301 sh, 374 sh, 440 sh.

IR: vcm^–1/ max KBr: 3420, 3380(O–H), 2800 (C-H), 2100 (C=C), 1680 (C=O), 1610 (C≡C), 1560, 1510, 1450, 1400 (aromatic), 1385, 1310, 1270, 1180, 1010.

¹HNMR (300MHz, CDCl₃): 2.45, (H₁), 2.55 (H₂), 6.79 (H₃), 6.98 (H₄), 6.49 (H₅), 2.33 (H₆), 6.38 (H₇), 2.36 (H₈), 5.37 (H₉), 1.4 (H₁₀).

¹³C NMR (300MHz, CDCl₃): 137.3 (C₁), 137.9 (C₂), 14.2 (C₃), 127.0 (C₄), 126.1 (C₅), 133.8 (C₆), 142.4 (C₇), 158.2 (C₈), 114.6(C₉), 134.5 (C₁₀), 123.0 (C₁₁), 138.0 (C₁₂), 121.1 (C₁₃), 149.4 (C₁₄), 108.9 (C₁₅), 127.8.

Kaempferol: Brownish needles on crystallization (mp 312°-313°C). UV light absorption MeOH: 253 sh, 269 sh, 305 sh, 374 sh, 424 sh.

IR: vcm^–1/ max KBr: 3420 (O–H), 2830 (C-H), 2240 (C=C), 1700 (C=O), 1600, 1610 (C≡C), 1560, 1510, 1450, 1400 (aromatic), 1385, 1310, 1270, 1180, 1010, 815.

¹HNMR (300MHz, CDCl₃): 2.35(H₁), 7.01(H₂), 7.18 (H₃), 6.29 (H₄), 6.37 (H₅), 2.35 (H₆), 5.39 (H₇), 5.36 (H₈), 7.18 (H₉), 7.01 (H₁₀).

¹³C NMR (300MHz, CDCl₃): 1.36 (C₁), 129.8 (C₂), 126.8 (C₃), 131.9 (C₄), 147.4 (C₅), 154.2 (C₆), 114.6 (C₇), 137.5 (C₈), 124.0 (C₉), 136.0 (C₁₀), 121.1 (C₁₁), 149.4 (C₁₂), 106.9 (C₁₃), 131.9 (C₁₄), 126.1 (C₁₅).

TABLE 3: SPECTRAL STUDIES OF ISOLATED FLAVONOIDS FROM TECOMELLA UNDULATA

GC-MS analysis of the extracted flavonoids from various plant parts of Tecomella undulata namely root, stem, bark, and leaf, was carried out. Various constituents obtained are reported, GC-MS spectra of flavonoids from roots, stem, bark, and leaves are shown in Tables 4, 5, 6, and 7.

TABLE 4: RETENTION TIME, MOLECULAR WEIGHT AND % AREA BY SETTING THE TOTAL PEAK AREA TO 100% OF FLAVONOIDS IDENTIFIED BY GC-MS IN LEAVES OF TECOMELLA UNDULATA

TABLE 5: RETENTION TIME, MOLECULAR WEIGHT AND % AREA BY SETTING THE TOTAL PEAK AREA TO 100% OF FLAVONOIDS IDENTIFIED BY GC-MS IN BARK OF TECOMELLA UNDULATA

TABLE 6: RETENTION TIME, MOLECULAR WEIGHT AND % AREA BY SETTING THE TOTAL PEAK AREA TO 100% OF FLAVONOIDS IDENTIFIED BY GC-MS IN ROOTS OF TECOMELLA UNDULATA

TABLE 7: RETENTION TIME, MOLECULAR WEIGHT AND % AREA BY SETTING THE TOTAL PEAK AREA TO 100% OF FLAVONOIDS IDENTIFIED BY GC-MS IN STEMS OF TECOMELLA UNDULATA

The active principles in the plants may not be major compound(s) in it but the activity of a compound may be masked by some other components in an extract ^{20, 21}. To evaluate the biological or pharmacological importance ^{22, 23} various activities such as antibacterial, antifungal, antiviral, antitumor, anti-inflammatory, antipyretic and analgesic were tested by a number of workers, with an aim to identify the active principle(s) and their bioefficacy ²⁴.

Table 8 shows detailed investigation of antimicrobial assay of crude extracts of flavonoids of Tecomella undulata.

Antifungal activity of the flavonoids extracted from different plant parts when tested against Fusarium showed that root showed maximum inhibition while stem showed minimum inhibition (Root; IZ=14.66 ± 2.51 mm > bark; IZ= 13.00 ± 2.00 mm > Leaf; IZ=12.66 ± 2.08 mm > Stem; IZ=11.00 ± 1.00 mm). When tested against Penicilium funiculosum, bark showed maximum inhibition while leaf showed mini (Bark; IZ =16.33 ± 1.00 mm > root; IZ = 14.66 ± 3.05 mm > stem; IZ = 9.66 ± 0.57 mm > leaf; IZ = 0.00 mm). Against Candida albicans leaf extract showed maximum inhibition while bark showed minimum (Leaf; IZ = 26.66 ± 2.08 mm > stem; IZ = 14.00 ± 1.00 mm > root; IZ = 13.33 ± 1.52 mm > bark; IZ = 12.67 ± 1.053 mm). Against T. virdae, bark showed maximum inhibition while stem showed minimum inhibition. (Bark; IZ = 26.00 ± 2.00 mm > leaf; IZ = 15.66 ± 2.08 mm > root; IZ = 14.33 ± 0.57 mm > Stem; IZ = 12.33 ± 2.51 mm).

Antibacterial activity of flavonoids against S. aureus was shown maximum by leaf whereas minimum by root (Leaf; IZ = 27.33 ± 2.08 mm > stem; IZ = 16.33 ± 1.52 mm > bark; IZ = 16.00 ± 1.00 mm > root; 0.00 mm). While against E. coli leaf showed maximum activity and root showed minimum inhibition (Leaf; IZ = 21.00 ± 1.00 mm > bark; IZ = 14.66 ± 1.52 mm > stem; IZ = 14.33 ± 2.08 mm > root; IZ = 14.00 ± 1.00 mm). Against enterococcus, none of the extracts showed any activity (Root, stem, bark, leaf; IZ = 0.00 mm). Against Bacillus subtilis, leaf showed maximum activity and stem showed minimum activity (Leaf; IZ = 20.66 ± 1.15 mm > bark; IZ = 17.00 ± 2.64 mm > root; IZ = 16.66 ± 1.52 mm > stem; IZ = 15.00 ± 1.00 mm). Against Klebsiella pneumonia, bark showed maximum whereas root and stem showed minimum inhibitory activity (Bark; IZ = 13.00 ± 1.73 mm > leaf; IZ = 11.66 ± 2.88 mm > root, stem; IZ = 0.00 mm).

TABLE 8: BACTERICIDAL AND FUNGICIDAL EFFICACY OF FLAVONOIDS CRUDE EXTRACTS OF TECOMELLA UNDULATA

CONCLUSION: The current investigation reveals the high amount of flavonoid in leaves which also show high inhibitory activity against C. albicans and S. aureus. A variety of Compounds with high Pharmacological Value were identified to be present in different plant parts of Tecomella undulata. Roheda is therefore a pack of bioactive components which can be further investigated for curing of ailments, which so far have not found a cure and put to Pharmacological use.

ACKNOWLEDGEMENT: I would like to acknowledge the Department of Botany University of Rajasthan for providing us with the lab facilities to carry out the research work. AIRF JNU Delhi for providing us the facility of GC-MS, and Seminal Applied Sciences Jaipur to provide us the facility to carry the work on pathogenic microorganisms.

CONFLICTS OF INTEREST: Nil

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    How to cite this article:

    Bhardwaj R and Sharma RA: Tecomella undulata (SM.) seem.- GC-MS analysis of flavonoids and inhibitory activity against pathogenic microbes. Int J Pharm Sci & Res 2020; 11(11): 5659-68. doi: 10.13040/IJPSR.0975-8232.11(11).5659-68.

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