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European Journal of Applied Sciences – Vol. 10, No. 2

Publication Date: April 25, 2022

DOI:10.14738/aivp.102.12172. Opondo, F. A., K’Owino, I. O., Chepkwony, S. C., Kosgei, V. J. (2022). In Vitro Antibacterial Activity of Essential Oils from Tithonia

Diversifolia Leaves and Flowers Against Ralstonia Solanacearum. European Journal of Applied Sciences, 10(2). 523-539.

Services for Science and Education – United Kingdom

In Vitro Antibacterial Activity of Essential Oils from Tithonia

Diversifolia Leaves and Flowers Against Ralstonia Solanacearum

Florence Atieno Opondo

Department of Chemistry and Biochemistry

School of Sciences and Aerospace, Moi University

P.O.BOX 3900-30100, Eldoret, Kenya

Africa Center of Excellence II in Phytochemicals Textiles and

Renewable Energy (ACEII-PTRE), Moi University

P.O.BOX 3900-30100, Eldoret, Kenya

Isaac Odhiambo K’Owino

Department of Chemistry and Biochemistry

School of Sciences and Aerospace, Moi University

P.O.BOX 3900-30100, Eldoret, Kenya

Africa Center of Excellence II in Phytochemicals Textiles and

Renewable Energy (ACEII-PTRE), Moi University

P.O.BOX 3900-30100, Eldoret, Kenya

Department of Chemistry, Faculty of Science

Masinde Muliro University of Science and Technology

P.O.BOX 190-50100 Kakamega, Kenya

Sarah Cherono Chepkwony

Department of Chemistry and Biochemistry

School of Sciences and Aerospace, Moi University

P.O.BOX 3900-30100, Eldoret, Kenya

Africa Center of Excellence II in Phytochemicals Textiles and

Renewable Energy (ACEII-PTRE), Moi University

P.O.BOX 3900-30100, Eldoret, Kenya

Viola Jepchumba Kosgei

Department of Chemistry and Biochemistry

School of Sciences and Aerospace, Moi University

P.O.BOX 3900-30100, Eldoret, Kenya

Africa Center of Excellence II in Phytochemicals Textiles and

Renewable Energy (ACEII-PTRE), Moi University

P.O.BOX 3900-30100, Eldoret, Kenya

ABSTRACT

Bacterial wilt disease caused by Ralstonia solanacearum is a major constraining

factor in the production of tomatoes in Kenya, leading to an overreliance on

synthetic pesticides. As a result, there is increased research on bio-pesticides as

safer alternatives. The present study, therefore, characterized and evaluated in

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European Journal of Applied Sciences (EJAS) Vol. 10, Issue 2, April-2022

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vitro antibacterial activity of essential oils from Tithonia diversifolia leaves and

flowers against R. solanacearum. Hydrodistilled essential oils were characterized

through Gas Chromatography-Mass spectrometry (GC-MS) while functional groups

were confirmed using Fourier Transform Infrared Spectroscopy (FT-IR).

Antibacterial activity was performed using the disc diffusion method and minimum

inhibitory concentration evaluated using broth dilution. Hydrodistilled leaves of T.

diversifolia yielded 0.18 + 0.08 % (v/w); 0.10 + 0.07 % w/w as compared to 0.15 +

0.09 % (v/w); 0.08 + 0.03 % w/w in the leaves . GC-MS profiling revealed the major

compounds were (Z,Z,Z)-9,12,15- Octadecatrienoic acid ethyl ester(18%), palmitic

acid (16%), spathulenol (12%), Cis- 9,12,15- Octadecatrienoic acid (8.14%),

tetrateracontane (6%) and 1-Octen-3yl-acetate (5.22%) in the leaves ad α-linolenic

acid trimethylester(33%), Z,Z Hexadecadienoic acid(26%), octadecanoic acid

trimethylester (9%), palmitelaidic acid (8.49%), Germacrene D(5.45%), azelaic

acid (5.02%) and caryophyllene oxide (5.00%) in the flowers. Antibacterial activity

showed that T. diversifolia essential oils had mean inhibition zones of 12.61+ 0.22

mm and 11.82 + 0.76 mm from the leaves and flowers respectively, in comparison

to metham sodium which gave inhibition zone of 25.78 ±0.29 mm (p = 0.001). Based

on the results, this study gives credence to T. diversifolia essential oils as viable

antibacterial agents.

Keywords: In vitro; antibacterial activity; Spathulenol; Tithonia diversifolia; Ralstonia

solanacearum

INTRODUCTION

Bacterial wilt caused by soil-borne bacterium Ralstonia solanacearum is one of the most

devastating bacterial disease limiting tomato production in tropical, subtropical, and warm

temperate regions of the World [1-4]. The bacterium is classified as the World’s most

destructive phytopathogenic bacteria causing tomato yield losses due to its lethality,

persistence, wide host range in solanaceous crops, ability to grow endophytically, survive in

soil, broad geographic distribution, and versatile methods of transmission [1-6]. Additionally,

R. solanacearum can survive in plant debris, infected plants host weeds, and spread from one

field to another by irrigation or floodwater, soil, farm equipment, and remaining crops from the

previous seasons, hence it is difficult to manage [3-4]. Despite the availability of several

methods for the management of bacterial wilt disease in tomatoes including chemicals,

biological agents, cultural and physical practices [3], the disease has not been successfully

managed in Sub-Saharan Africa [2,7]. Emerging trends in physical practices for control of R.

solanacearum include solarization, hot water treatment of infected soil, planting in the cold

season, soil fumigation, and soil drenching [3]. Some of the aforementioned methods including

planting tomato, potato and tobacco crops during winter when the temperatures are low and

the bacterium is inactive6, may not be viable in Sub-Saharan Africa where temperatures are

usually high all year round. In addition, wet conditions and moderate temperatures in Sub- Saharan Africa usually favor the survival of the bacteria [7]. As a result, synthetic pesticides

continue to be overused for plant disease management and pest control due to their efficacy,

reliability, rapidity of action, and quick knockdown effect [8-9]. However, control of R.

solanacearum using synthetic pesticides has far-reaching implications such as environmental

pollution, contamination of groundwaters, accumulation of toxic residues in food, and

elimination of non-target organisms [9-12]. Biopesticides on the other hand are less toxic, less

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Opondo, F. A., K’Owino, I. O., Chepkwony, S. C., Kosgei, V. J. (2022). In Vitro Antibacterial Activity of Essential Oils from Tithonia Diversifolia Leaves

and Flowers Against Ralstonia Solanacearum. European Journal of Applied Sciences, 10(2). 523-539.

URL: http://dx.doi.org/10.14738/aivp.102.12172

persistent, environment-friendly, safe to humans and non-target organisms, economically

affordable, highly effective, and target specific [8-13].

Application of biopesticides includes the use of bio-control agents like Bacillus

amyloliquefaciens [5] and Pseudomonas fluorescens [14] and plant extracts like Amomum

nilgiricum [15] for control of R. solanacearum. Furthermore, biopesticides have been appraised

to be less persistent in the environment as they are often degraded rapidly by sunlight, or

moisture, are less phytotoxic, and are consequently potentially less of a threat to the

environment and human health [8]. Additionally, they contain a mixture of compounds, which

can work together synergistically in reducing a pathogen or pest with varying modes of action

[16]. In this context, plant extracts contain Phyto complex of active compounds which could be

contributing to the overall biological effect against bacteria through the collective effect of all

its components, some of which will cooperate and some might modulate, while others will act

on different, distantly connected targets, ultimately generating synergistic activity of the

phytoconstituents [16-17]. Essential oils, in particular, have been demonstrated to be effective

antibacterial agents because their lipophilic characteristics contribute to their being capable of

destroying the cell wall of bacteria [18]. Additionally, they contain a large number of

phytochemicals and hence it is most likely that the reported antibacterial activity of essential

oils is due to the synergistic effect of all the constituents and not attributed to one mechanism

[18]. Therefore, using essential oils as biopesticides could lead to reduced occurrence of

pathogen and pest resistance development. As a result, the use of essential oils has been on the

increase as an emerging, potential, and alternative approach in disease management for R.

solanacearum [12, 19-20]. Essential oils are naturally occurring volatile substances obtained

from a variety of plants including T. diversifolia [21].

T. diversifolia (Hemsl.) A. Gray (Asteraceae) is a shrub and a member of the sunflower family

and is native to North and Central America [21-22]. Although this species is native to the

lowlands of southeastern Mexico and Central America, it has now been naturalized in different

regions of the world including Africa and Asia [22], where they have become an ecological,

agricultural, and economic burden [23].

Despite the negative effects of the invasive shrub, ethno pharmacologically, T. diversifolia has

been exploited in folkloric medicinal practices as well as in remediation of heavy metals from

the soil [21, 23].

In Nigeria, T. diversifolia has been reported to be used by herbal medicine practitioners in the

treatment of menstrual pain, treatment of wounds, and diabetes mellitus [22]. In Mexico where

this plant originates from, it is used to treat sprains, bone fractures, bruises and contusions [22].

In Kenya, T. diversifolia locally known as maruru, maua and amalulu (for Luhya tribe), maua

makech (Luo), amaua amaroro (Kisii) and mula (Kamba) all implying that the plant is bitter to

the taste are effectively used for treatment of snake envenomation [24-25]. Among the Kalenjin

community in Kenya, T. diversifolia is commonly known as mauat ne ng’wan meaning bitter

flowers, and is used to treat diarrhea.

Biological activities of T. diversifolia includes anti-inflammatory, analgesic, antimalarial,

antiviral, antidiabetic, antidiarrhoeal, antimicrobial, antispasmodic, vasorelaxant, cancer- chemo preventive, insecticidal, antiemetic, and antiamoebic properties [21-22, 26-27]. Most of

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the pharmacological activities of T. diversifolia have been attributed to sesquiterpene, lactones,

diterpenes, flavonoids and some chlorogenic acid derivatives present in the leaves of this

species [21]. T. diversifolia essential oils consist of terpenes, terpenoids and lactones [28]. These

compounds have been demonstrated to possess antibacterial, antifungal and insecticidal

activities [23, 28]. In a previous study, Farias et al., [26] demonstrated antimicrobial activity of

T. diversifolia leaf essential oils against Staphylococcus aureus, Escherichia coli, and

Pseudomonas aeruginosa and reported that the observed antimicrobial activity was due to the

presence of the main chemical constituents including α-pinene, Limonene, (Z)-β-ocimene, p- cymen-8-ol, Piperitone, (E)-nerolidol and Spathulenol. In another study, Agboola et al., [28],

evaluated the chemical composition and antimicrobial activity of T. diversifolia essential oils

they reported that secondary metabolites present in the oils including monoterpenes,

sesquiterpenes, alcohols, and aldehydes proved effective against Escherichia coli, Proteus

mirabi, Bacillus megaterium, Klebsiella pneumonia, Bacillus cereus and Streptococcus pyrogens

thereby, unlocking the potential of the oils for bio-pesticide production. In a recent study,

Njuguna et al., [29], investigated the contact toxicity of essential oils from the T. diversifolia

leaves against Thrips tabaci, Bemisia tabaci, and Aphis gosypii and reported that the essential

oils possessed remarkable insecticidal activity which could be employed as a safer alternative

to synthetic pesticides. In this context, the current research evaluated the chemical composition

of T. diversifolia essential oils and investigated their antibacterial potential against R.

solanacearum in vitro, with the aim of developing natural, green, and sustainable biopesticides

for application in the management of bacterial wilt disease in tomato.

MATERIALS AND METHODS

Sample collection and preparation

Fresh leaves and flowers from T. diversifolia were collected from Maseno in Kisumu County GPS

location, 0°02'10.2"S34°45'18.8" E, in Kenya. All the plant samples collected were taken to the

Chemistry laboratory at Moi University. Voucher specimens of the plant species were deposited

at the laboratory of Biological Sciences of Moi University. The fresh samples from T. diversifolia

were then washed using distilled water to remove dust and immediately chopped into small

sizes and placed into 1000 mL clevenger apparatus for hydrodistillation.

Extraction

Essential oils from the fresh leaves and flowers of T. diversifolia were extracted separately via

hydrodistillation using clevenger apparatus according to the methods of Liu et al., [30], as

described by Wanzala et al., [31]. Briefly, 1 kg of freshly chopped T. diversifolia leaves and

flowers were separately weighed and hydrodistilled with 1500mL of distilled water using

clevenger apparatus for 8 hours. After hydrodistillation was completed, the volatile essential

oils were removed from the top of the hydrosol, dried over anhydrous sodium sulfate (Na2SO4),

and stored in sealed amber bottles at 4 °C awaiting chemical and bioassay analyses.

GCMS Analysis of essential oils and solvent extracts

GC-MS analyses was performed with a Clarus 500 GC gas chromatograph (Perkin Elmer Inc.,

USA) coupled with a Clarus 500 MS quadrupole mass spectrometer (Perkin Elmer Inc., USA).

Gas chromatography was carried out on a fused-silica capillary column (Elite-5 ms,

60 m×0.25 mm, 0.25 μm film thickness, Perkin Elmer Inc, USA). The gas chromatograph was

equipped with an electronically controlled split/splitless injection port while the carrier gas

was helium with a constant flow of 1.2 mL/min. The GC oven temperature was set at 200 ͦC for

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Opondo, F. A., K’Owino, I. O., Chepkwony, S. C., Kosgei, V. J. (2022). In Vitro Antibacterial Activity of Essential Oils from Tithonia Diversifolia Leaves

and Flowers Against Ralstonia Solanacearum. European Journal of Applied Sciences, 10(2). 523-539.

URL: http://dx.doi.org/10.14738/aivp.102.12172

4 min and programmed in the range 200 ͦC -330 ̊C at a rate of 5 ̊C /min and finally held constant

at 330 ͦC for 15 min. Ionization was performed in the electron impact mode at 70 eV, while

detection was carried out in scan mode from m/z 35- 700 atomic mass units ( a.m.u). Relative

percentage amounts were obtained directly from GC peak areas while retention time was

recorded in minutes. Components present in the essential oils were identified by matching of

mass spectral data with MS library NIST 08 (NIST/EPA/NIH) and comparing the MS

fragmentation patterns with those reported in the literature.

Fourier Transform Infrared (FT-IR) spectroscopy

The essential oils were characterized to confirm the functional groups in the compounds

identified by GC- MS analysis. The essential oils, from T. diversifolia leaves and flowers, were

analyzed using an Attenuated Total Reflectance- Fourier Transform Infrared (ATR-FTIR)

spectrophotometer, NICOLET 6700 Thermo Scientific 2009-27701 Model. The FT-IR spectra

were recorded in the spectral range 4000 to 500 cm-1 and scanning was performed with a

resolution of 4 cm−1 for 100 scans. The functional groups of compounds present in the essential

oils were determined by comparing the wavenumbers in the spectra with those on an IR

correlation chart and comparison of spectral data with those reported in previous studies.

Bactericidal Activity

Isolation and characterization of Ralstonia solanacearum strains

All experiments were performed using highly virulent R. solanacearum strain race 3 biovar III

which was isolated from ten diseased potato plants from Timboroa, Uasin Gishu County, and

deposited at the Biological sciences Laboratory at Moi University. Collected potato tubers were

sterilized with 1% Sodium Hypochlorite (NaOCl) solution for 2 min, followed by three repeated

washings with distilled water and blot dried according to the methods of Singh as described by

[32]. The plant sections (0.5 cm) were then placed inside test tubes containing distilled water

and then be plated onto 2, 3, 5 triphenyl tetrazolium chloride (Kelman’s TZC agar) medium

(glucose 10 g, peptone 10 g, casein hydrolysate 1 g, agar 18 g, distilled water 1000 ml). An

aliquot of 5 ml TZC solution filter-sterilized was added to autoclaved medium to give a final

concentration of 0.005% v/v, followed by incubation of the plates at 28 ̊C for 48 hours [32].

The virulent colonies in the medium were characterized by dull white color, fluidal, irregularly

round with light pink centers which were further streaked on TZC medium to get pure colonies

of the bacterium. Isolated pure colonies of R. solanacearum were refrigerated at 20 ̊C to

maintain their virulence. To revive an isolate, the stored bacteria were streaked on a TZC agar

medium and well-separated fluidal colonies were selected. Preparation of R. solanacearum

bacterial suspension was performed by pouring sterile distilled water over 24hr old bacterial

growths on nutrient agar slants, and the suspension was adjusted to an optical density (O.D)

0.5 in Spectrophotometer ( Beckham Coulter DU 700) to obtain a bacterial population of 1 x 108

colony-forming unit per milliliter of the suspension (optical density at 600 nm). Profiling of the

pathogen was performed morphologically using culture techniques and biochemical tests

including Gram staining test, Potassium hydroxide test, Catalase oxidase test, Gas production

test, Starch hydrolysis test, and sugar utilization test according to Manual of Systematic

Bacteriology as described by [32].

In vitro disc diffusion experiments

The antibacterial activity of the essential oils from T. diversifolia leaves and flowers were tested

in vitro against R. solanacearum according to the disk diffusion method described by [33].

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Briefly, a single colony of the isolate containing 1x 108 Colony Forming Units (CFU) at 0.5 optical

density measured at 600nm was grown on casamino acid peptone glucose medium (CPG) at 28

°C for 48 hours. Each bacterial suspension (200 μl) was then spread on nutrient agar plates and

5mm diameter disks containing 50 μL of essential oil were placed on the surface of the prepared

agar plates. Sterile 1% dimethyl sulphoxide was used as negative control while Metham sodium

(125 μg/mL) a known soil fumigant [1]. was used as a positive control. The plates were then

incubated at 28°C for 24 hours after which diameters of inhibition zones were measured in

millimeters using Vernier calipers. All experiments were performed in triplicate.

Minimum inhibitory concentration

Minimum inhibitory concentration (MIC) was evaluated using the broth microdilution method

using a 96 well microtiter plate as described by [34], with a few modifications on the synthetic

fumigant used. Briefly, 50μL of essential oil was added from the 1st to the 10th well on each row

and diluted two-fold using 1% DMSO in the concentration range 1.953- 1000 μg/mL. Negative

control (1% DMSO) and positive control (metham sodium) were also prepared in the same

concentration range. Then, 50μL of 1x 10-8 CFU of freshly prepared R. solanacearum colonies

were added to each well followed by incubation at 28 °C for 24 hours. Finally, 50 μL of 0.01%

Tetrazolium chloride medium (TZC) was added to each well followed by incubation at 28 °C

for one hour after which MIC was evaluated by visual observation of the color change of the

Tetrazolium chloride medium.

Statistical analysis

Data on the in vitro antibacterial activities of T. diversifolia essential oils against R. solanacearum

were analyzed statistically using Minitab version 17 software at a 99% confidence interval.

Data from mean inhibition zones from three replicate experiments on the four treatments

bioassayed were analyzed and the standard mean error was computed. The difference between

the means was analyzed using One Way Analysis of Variance (ANOVA). Means of inhibition

diameters were separated using Tukey’s honestly significant difference test [33]. p-values

<0.01 were considered statistically significantly different [35].

RESULTS AND DISCUSSIONS

Extraction of essential oils

Essential oils from leaves and flowers of T.diversifolia, were hydrodistilled using clevenger

apparatus. Data obtained was tabulated as shown below:

Table 1: Percentage yield for essential oils

Plant extracts Part of the plant % yield (Volume/

weight)

% yield (Weight/

weight)

T.diversifolia Leaves 0.18+ 0.08 0.10+ 0.07

Flowers 0.15 + 0.09 0.08 + 0.03

Percentage yield of the essential oils was calculated in volume by weight and weight by weight

(Igwaran et al., 2017) as shown in equations1 and 2 below:

% Essential oil yield (v/w) = !"#$%& "( &)&*+,-# ",# (%#)

0&,12+ "( 3#-*+ )-%3#& (1)

(Equation 1)

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Opondo, F. A., K’Owino, I. O., Chepkwony, S. C., Kosgei, V. J. (2022). In Vitro Antibacterial Activity of Essential Oils from Tithonia Diversifolia Leaves

and Flowers Against Ralstonia Solanacearum. European Journal of Applied Sciences, 10(2). 523-539.

URL: http://dx.doi.org/10.14738/aivp.102.12172

% Essential oil yield (w/w) = 4&,12+ "( &)&*+,-# ",# (1)

56&)2 0&,12+ "( 3#-*+ )-%3#& (1)

(Equation 2)

Leaves of T. diversifolia gave the highest percentage yields of 0.18 + 0.04 % (v/w); 0.10 + 0.02

% w/w as compared to the flowers which yielded 0.15 + 0.07 % (v/w); 0.08 + 0.01 % w/w on

a fresh weight basis, however there was no statistical significant difference between leaves and

flowers essential oils yields (p˃ 0.01). Similar results were obtained by [36], who reported

essential oils yields of 0.18% v/w in T. diversifolia leaves essential oils. Contrary, Moronkola et

al., [37], performed hydrodistillation of air-dried plant material from T. diversifolia and

reported essential oil yields of 0.019 and 0.1% w/w in the leaves and flowers respectively. In

another study, [38], reported essential oils yields of 0.12% v/w while performing

hydrodistillation of air-dried leaves of T. diversifolia. The low yields reported in the leaves and

flowers may be due to the fact that air-dried plant materials were used for hydrodistillation

contrary to the fresh leaves and flowers used in this current research. It is noteworthy that

studies performed using fresh leaves of T. diversifolia leaves and flowers reported higher

essential oils [26,36], suggesting that the sample preparation process is a significant factor that

affects essential oils yields. Other factors known to affect T. diversifolia essential oils yields

include the geographical location, climatic conditions, type of soil, and phenotypic

characteristics of the plant [21,39].

GC MS analysis

GC MS analysis of T. diversifolia essential oils tentatively identified 21 compounds in the leaves

and 8 compounds in the flowers as shown in Tables 2 and 3 respectively. The relative amounts

were based on the relative percentage area computed directly from the area under the GC

spectra (Figure 1 and Figure 2). Compounds were listed according to their elution order on a

non-polar fused-silica capillary column (table 2). GC MS profiling revealed that the essential oil

constituents of the leaves was dominated by fatty acids (74.2%), oxygenated sesquiterpenes

(12%), and oxygenated monoterpenes (10.48%) (Table 4), whereby the major compounds

present were found to be (Z,Z,Z)-9,12,15- Octadecatrienoic acid ethyl ester(18%), palmitic acid

(16%)(1aS,4aS,7R,7aS,7bS)-1,1,7-Trimethyl-4-methylenedecahydro-1H-cyclopropa[e]azulen- 7-ol (spathulenol) (12%), Cis- 9,12,15- Octadecatrienoic acid (8.14%), tetrateracontane (6%)

and 1-Octen-3ylcetate (5.22%).The major chemical constituents in the flowers' essential oils

were fatty acids (86.73%), sesquiterpene hydrocarbons (5.45%), and oxygenated

sesquiterpenes (5%), as evidenced by the presence of α-linolenic acid trimethylester(33%),

Z, Z Hexadecadienoic acid(26%), octadecanoic avid trimethylester (9%), palmitelaidic acid

(8.49%) and S, 1Z, 6Z) -8 Isopropyl-1 methyl-5- methylenecyclodeca-1,6-diene (Germacrene

D)(5.45%) azelaic acid (5.02%) and caryophyllene oxide (5.00%) (Table 3). Minor compounds

assayed in the leaf essential oils included α-pinene (1.17%), β-pinene (1.17%), 1-octen-3-ol

(2.21%), 2-octen-1-ol (1.17%) and bicycloheptane (0.63%). Similar findings were observed by

Farias et al., [26], who reported that α- pinene, Limonene, (Z)-β-ocimene, Piperitone, and

Spathulenol were some of the major chemical constituents identified in T. diversifolia leaves. In

another study, contrary to our results, Wanzala et al., [31], analyzed the aerial parts of T.

diversifolia growing on the southern slopes of Mount Elgon in western Kenya and reported that,

α- pinene, β-pinene, iso caryophyllene, nerolidol, 1-tridecanol, limonene, sabinene, α-copaene,

α-gurjunene, and cyclodecene are pre-dominantly distributed. In a recent study, Njuguna et al.,

[29], while evaluating the qualitative and quantitative profiling of essential oils from air-dried

leaves of T. diversifolia collected from Kandara in Murang’a County, Kenya reported that 3-

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carene was the most abundant compound in the essential oils. Major differences were observed

in the essential oils composition of T. diversifolia growing in the Maseno region, Kisumu County,

Kenya as compared to other regions in Vietnam [38], and Brazil [39], as reported in previous

studies. This could be attributed to environmental conditions, ecological conditions, climatic

factors, geographical distribution, extraction method, sample preparation protocols, and part

of the plant assayed [21, 26, 39].

Figure 1: GC spectrum of T. diversifolia leaf essential oils

20211027 , 27-Oct-2021 + 17:07:12

6.40 11.40 16.40 21.40 26.40 31.40 36.40 41.40 46.40

0 Time

100

%

TDEOL3 02 Scan EI+

TIC

2.10e9

26.14

23.18

12.72

10.07

2.81

6.07 5.27 6.77 10.20

22.46

14.01

25.85

23.39

25.29

34.97

32.36

29.46 28.59

28.06 30.44

34.83 36.22

37.82

39.77

42.21

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Opondo, F. A., K’Owino, I. O., Chepkwony, S. C., Kosgei, V. J. (2022). In Vitro Antibacterial Activity of Essential Oils from Tithonia Diversifolia Leaves

and Flowers Against Ralstonia Solanacearum. European Journal of Applied Sciences, 10(2). 523-539.

URL: http://dx.doi.org/10.14738/aivp.102.12172

Table 2: GC-MS Analysis of compounds present in T. diversifolia leaves essential oils

Peak

no

Retention

time

Compound Relative percentage area

1 5.27 alpha.-Pinene 1.17

2 6.07 1-Octen-3-ol 2.21

3 6.65 beta.-Pinene 0.22

4 6.77 2-Octen-1-ol, (Z)- 3.42

5 10.07 1-Octen-3-yl-acetate 5.22

6 10.20 Bicyclo(3.1.1)heptane-2,3-diol,

2,6,6-trimethyl- 0.63

7 12.72 Spathulenol 12

8 14.01 Azelaic acid bis trimethylester 1

9 22.46 n-Hexadecanoic acid 2

10 23.18 Palmitic acid 16

11 23.39 Palmitic acid, ethylester 7.12

12 25.29 (Z,Z,Z)-9,12,15- Octadecatrienoic

acid methyl ester

2

13 25.85 Cis- 9,12,15- Octadecatrienoic acid 8.14

14 26.14 (Z,Z,Z)-9,12,15- Octadecatrienoic

acid ethyl ester

18

15 28.06 Hexadecanoic acid cyclohexylester 2

16 28.59 Tetracosane 5.94

17 29.48 Heptacosane 2

18 30.44 Hentriacontane 1

19 32.36 Tetratriacontane 1

20 34.97 Tetratetracontane 6

21 37.82 Tetracosanoic acid 2

Figure 2 :GC spectrum for T. diversifolia flowers essential oils

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Table 3: GC-MS analysis of compounds present in T. diversifolia flower essential oils

Retention

time

Retention time Compound Relative percentage

area

1 12.63 Caryophyllene oxide 5

2 13.45 Germacrene D 5.45

3 14.59 Azelaic acid bis trimethylester 5.02

4 16.50 Palmitelaidic acid 8.49

5 16.58 (Z,Z)-Hexadecadienoic acid -

trimethylester

26

6 17.73 α-Linolenic acid, trimethylester 33

7 17.84 Octadecanoic acid trimethyl ester 9

8 25.07 Hexadecanoic acid cyclohexylester 5.22

Table 4: Analysis of chemical constituents present in T. diversifolia leaf and flower essential

oils

Chemical compound group Leaf Area % Flower Area %

Monoterpene hydrocarbons 1.39 -

Oxygenated monoterpenes 10.48 -

Sesquitrepene hydrocarbons - 5.45

Oxygenated sesquiterpenes 12 5

Fatty acids 74.2 86.73

Total 98.07% 97.18%

FTIR analysis

Characterization of T. diversifolia leaf essential oils using FTIR-ATR gave significant broadband

at 3410.87 cm-1 in the region 3450 cm-1 to 3300 cm-1 representing –OH stretching vibrations

of essential oils and two peaks at 2918.78 cm-1 and 2848.07 cm-1 depicting C-H stretching

vibrations (Table 6). There was a significantly strong peak at 1710.63 cm-1 in the leaf essential

oils which is a typical -C=O stretching bands [40], attributed to the presence of spathulenol

which was one of the principal phytoconstituents identified by GC-MS analysis. Other

vibrational frequencies were observed at 1466. 11 cm-1, 1317.82 cm-1, 1183.24 cm-1 and

1020.51 cm-1 as summarized on Table 6 below. In the flowers, significant peaks were observed

at 3375.51 cm-1, 2921.58 cm-1 , 2851.01 cm-1 , 1713.63 cm-1,1195.02 cm-1 and 1018.23 cm-1

(Table 6). Similar results were reported by [41-42].

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Opondo, F. A., K’Owino, I. O., Chepkwony, S. C., Kosgei, V. J. (2022). In Vitro Antibacterial Activity of Essential Oils from Tithonia Diversifolia Leaves

and Flowers Against Ralstonia Solanacearum. European Journal of Applied Sciences, 10(2). 523-539.

URL: http://dx.doi.org/10.14738/aivp.102.12172

Table 6: FTIR analysis of T. diversifolia leaf and flower essential oils

Major absorption bands (cm-1)

T. diversifolia leaves

essential oils

T. diversifolia flowers

essential oils

Functional groups

3410.87 3375.51 -OH group

2918. 78 2921.58 -C-H stretching vibrations

2848.07 2851.01 -C-H stretching vibrations

1710.63 1713.63 -C=O stretching

1466.11 1442.54 -CHbending vibrations

1317.82 1309.47 -CH bending vibrations

1183.24 1195.02 C-O stretching vibrations

1020.51 1018.23 C-O-C stretching vibrations

In vitro Antibacterial activity

Highly virulent R. solanacearum strain race 3 biovar III were isolated from ten diseased potato

plants from Timboroa, Uasin Gishu County, and were characterized using biochemical tests. The

wild R. solanacearum colonies gave positive results for the catalase oxidase test and potassium

hydroxide solubility tests as shown in Figures 5a and 5b below and were found to be gram- negative as depicted in figure 5c and 5d. Similar results were obtained by Khasabulli et al., [32],

who reported that the positive catalase test could be attributed to the presence of catalase

enzyme in R. solanacearum because Gram-negative bacteria undergo aerobic respiratory

metabolism hence the Production of gas bubbles was observed.

a b

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Figure 5 a) Potassium hydroxide solubility test, b) Catalase oxidase test, c) Gram staining of R.

solanacearum, Magnification x 10, d) Gram staining of R. solanacearum, Magnification x 100

R. solanacearum colonies were identified by their large and elevated size, fluidal nature, and

color [43], characterized by dull white color, fluidal, irregularly round with light pink centers

as shown in Figure 6 a below. The virulent colonies were further steaked on TZC Kelman’s

medium to get pure colonies of the bacterium as depicted in Figure 6 b. Virulent colonies of R.

solanacearum were identified by their large and elevated size, fluidal nature, and if they were

either entirely white, or with a pale red center while the mutant and non-virulent strains of R.

solanacearum were uniformly round and dark red, smaller in size, and butyrous or dry on TZC

medium (Figures 6a and 6b). Similar results were obtained by [32, 43], who reported that the

virulent R. solanacearum colonies were characterized by fluidal whitish with a pink center,

indicating virulent species.

Figure 6: a) Virulent and avirulent colonies of R. solanacearum isolates b) Culturing of R.

solanacearum bacterium on TZC Kelman’s Agar medium

In vitro antibacterial activity of the essential oils from T. diversifolia leaves and flowers against

R. solanacearum was analyzed using the disk diffusion quadrat method. The data obtained was

tabulated as shown in Table 7 and illustrated in Figure 7.

c

d

a

b

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Opondo, F. A., K’Owino, I. O., Chepkwony, S. C., Kosgei, V. J. (2022). In Vitro Antibacterial Activity of Essential Oils from Tithonia Diversifolia Leaves

and Flowers Against Ralstonia Solanacearum. European Journal of Applied Sciences, 10(2). 523-539.

URL: http://dx.doi.org/10.14738/aivp.102.12172

Table 7: In vitro antibacterial activity of T. diversifolia essential oils against R. solanacearum

after 24 hours of incubation at 28°C

SNO Treatment Diameter of inhibition zones

in (mm)

1 1% DMSO 5±0.22c

2 TDEOL 11.82 ±0.47b

3 TDEOF 12.61 ±0.22b

4 METHAM SODIUM 25.78 ±0.29a

Values are the mean of three replicates ± standard error.

Values within columns followed by different letters are significantly different at P ≤ 0.01

according to Tukey’s honestly significant difference test

Figure 7: Antibacterial activity of T. diversifolia essential oils against R. solanacearum in vitro

Mean zone of inhibition results revealed that essential oils from the leaves of T.diversifolia

exhibited the highest antibacterial activity of 12.61 ±0.22 in the leaves, as compared to 11.82

±0.76 in the flowers. The MIC for T. diversifolia essential oils against R. solanacearum was 250

μg/mL in the leaves and 500 μg/mL in the flowers (Table 8) while the MIC for Metham sodium

was 125 μg/mL. Statistical analysis of the antibacterial activity of T. diversifolia essential oils in

comparison to Metham sodium which was the positive control revealed that there was a

statistically significant difference between the antibacterial activity of T. diversifolia leaves in

comparison to metham sodium (p = 0.001). Similarly, a statistically significant difference was

observed between the antibacterial activity of Metham sodium and the antibacterial activity of

T.diversifolia flowers essential oils (p = 0.0009) as shown in table 7. A comparison of bioactivity

between the T. diversifolia leaf and flower essential oils and 1% DMSO which was the negative

control (Table 7), revealed that there was a significant difference in bioactivity with p < 0.01.

The observed antibacterial activity of T. diversifolia essential oils could be attributed to

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phytochemicals including monoterpene hydrocarbons, oxygenated monoterpenes, and

sesquiterpene Hydrocarbons, oxygenated sesquiterpenes, and fatty acids as depicted by GC-MS

profiling of the major phyto compounds and confirmed by FTIR analysis.

Table 8: Minimum inhibition concentration (MIC) values for T. diversifolia essential oils, DMSO,

and Metham sodium against R. solanacearum after 24 hours of incubation

Treatments Concentration μg/mL

1.953 3.906 7.8185 15.625 31.25 62.5 125 250 500 1000

1% DMSO + + + + + + + + + +

TDLEO + + + + + + + + - -

TDFEO + + + + + + + - - -

METHAM

SODIUM

+ + + + + + - - - -

KEY

+ bacterial growth appears

- no bacterial growth

Essential oils contain monoterpenes, diterpenes, and sesquiterpenes which serve as defense

molecules in different plant parts [19], and hence the bioactivity of T. diversifolia essential oils

against gram-negative. R. solanacearum bacterium in vitro could be attributed to the presence

of the major chemical constituents including (1aS,4aS,7R,7aS,7bS)-1,1,7-Trimethyl-4-

methylenedecahydro-1H-cyclopropa[e]azulen-7-ol, 0Z- Octen-1-ol, (24.22%), (Z,Z,Z)-9,12,15-

Octadecatrienoic acid ethyl ester), Cis- 9,12,15- Octadecatrienoic acid(12%), 1-Octen-3ylcetate

and (S, 1Z, 6Z) -8 Isopropyl-1 methyl-5- methylenecyclodeca-1,6-diene, which could be causing

the synergistic antibacterial effect. Additionally, minor compounds profiled including α-pinene,

β-pinene in the leaves, and caryophyllene oxide in the flowers are known antibacterial agents

[44] and could be responsible for the observed antibacterial activity against R. solanacearum in

vitro. These results are in agreement with a previous study by [26], who reported that the main

compounds found in T. diversifolia essential oils including α-pinene, Limonene, (Z)-β-ocimene,

p-cymen-8-ol, Piperitone, (E)-nerolidol, and Spathulenol could be responsible for the

antimicrobial activity against Staphylococcus aureus, Escherichia coli, and Pseudomonas

aeruginosa. In another study, Li and Yu [45], demonstrated that R. solanacearum is susceptible

to the presence of essential oils in vitro. The findings in this current research revealed that T.

diversifolia leaf and flower essential oils possess remarkable in vitro antibacterial activity

against R. solanacearum and hence, could be used to make viable formulations to combat the

devastating tomato bacterial wilt disease.

CONCLUSION

This study demonstrated that T. diversifolia leaf and flower essential oils possess

phytochemicals including monoterpene hydrocarbons, oxygenated monoterpenes,

sesquiterpene hydrocarbons, oxygenated sesquiterpenes, and fatty acids. Additionally, in vitro

antibacterial activity showed that the profiled phytochemicals possessed remarkable

antibacterial activity against R. solanacearum. Based on the observed antibacterial activity of

the T. diversifolia leaves and flowers essential oils, this study emphasizes the great potential of

these essential oils for commercial applications in the management of phytopathogenic

bacteria and corroborates the extensive use of T. diversifolia in folkloric medicine.

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Opondo, F. A., K’Owino, I. O., Chepkwony, S. C., Kosgei, V. J. (2022). In Vitro Antibacterial Activity of Essential Oils from Tithonia Diversifolia Leaves

and Flowers Against Ralstonia Solanacearum. European Journal of Applied Sciences, 10(2). 523-539.

URL: http://dx.doi.org/10.14738/aivp.102.12172

ACKNOWLEDGMENT

The authors are grateful to the World Bank, through the Africa Center of Excellence II in

Phytochemicals, Textiles and Renewable Energy (ACEII-PTRE), and Moi University for funding

this work. The Authors also acknowledge LERMab for the GC-MS profiling and FT-IR analysis

that was performed in the (LERMAB), research group laboratory, at the University of Lorraine,

France.

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