Characterization of metabolites produced by shegilla dysenteriae and determination of its anti fungal activity.

Characterization of Metabolites Produced by Shegilla
dysenteriae and Determination of Its Anti-Fungal Activity
Fatima Moeen Abbas1
, Rafid Hadi Hameed2
, Imad Hadi Hameed3
1
Department of Biology, College of Science for Women, University of Babylon, Hillah city, Iraq, 2
Ministry of Public
Health, Maysan Health Department, Mesan Governorate, Iraq, 3
Biomedical Science Department, University of
Babylon, College of Nursing, Hillah City, Iraq
ABSTRACT
Shigella species generally invade the epithelial lining of the colon, causing severe inflammation and death of
the cells lining the colon. This inflammation results in the diarrhea and even dysentery that are the hallmarks
of Shigella infection. The aims of our research were analysis of the secondary metabolite products and
evaluation antifungal activity. Forty bioactive compounds were identified in the methanolic extract of Shegilla
dysenteriae. GC-MS analysis of Shegilla dysenteriae revealed the existence of the 1-Deoxy-d-mannitol,
γ-Thionodecalactone, Hexaborane, 1-Propanamine, 3-(methylthio), 1H-Pyrrole, 1-pentyl, 2-Propanone,
1-(N-cyanomethylimino-), 1-Pentanol, 5-methoxy, 2-Methyl-4-methoxy-1-butanol, Benzeneethanamine,
2-Butanamine , (S), L-valine , N-glycyl, N-carbobenzyloxy-l-tyrosyl-l-valine, DL-Isoleucine, and 3-Buten-
2-one, 4-(dimethylamino)-3-[(1-methylethyl). Daucus carota was very highly active (6.953±0.22) mm.
The results of anti-fungal activity produced by Shegilla dysenteriae showed that the volatile compounds
were highly effective to suppress the growth of Aspergillus flavus (6.00±0.22). Based on the significance
of employing bioactive compounds in pharmacy to produce drugs for the treatment of many diseases, the
purification of compounds produced by Shegilla dysenteriae can be useful.
Keywords: Shegilla dysenteriae, GC-MS, Anti-microbial, Secondary metabolites.
INTRODUCTION
Shigella infection is typically by ingestion.
Depending on the health of the host, fewer than 100
bacterial cells can be enough to cause an infection. Some
strains of Shigella produce toxins which contribute to
disease during infection. Shigella species invade the host
through the M-cells interspersed in the gut epithelia of
the small intestine, as they do not interact with the apical
surface of epithelial cells, preferring basolateral side1-
5
. After invasion, Shigella cellsmultiply intracellularly and
spread to neighboring epithelial cells, resulting in
tissue destruction and characteristic pathology of
Corresponding author:
Imad Hadi Hameed.
Biomedical Science Department, University of
Babylon, College of Nursing, Hillah City, Iraq; Phone
number: 009647716150716;
E-mail: imad_dna@yahoo.com
shigellosis. Shigella uses a type-III secretion system,
which acts as a biological syringe to translocate toxic
effector proteins to the target human cell. The effector
proteins can alter the metabolism of the target cell, for
instance leading to the lysis of vacuolar membranes
or reorganization of actin polymerization to facilitate
intracellular motility of Shigella bacteria inside
the host cell 6-9
. The most common symptoms
are diarrhea, fever, nausea, vomiting, stomach cramps,
and flatulence. It is also commonly known to cause
large and painful bowel movements. Virulent Shigella
strains produce disease after invading the intestinal
mucosa; the organism only rarely penetrates beyond the
mucosa. The stool may contain blood, mucus, or pus.
Hence, Shigella cells may cause dysentery. Shigella is
implicated as one of the pathogenic causes of reactive
arthritis worldwide.
DOI Number: 10.5958/0976-5506.2018.00486.2

Indian Journal of Public Health Research & Development, May 2018, Vol. 9, No. 5 453
MATERIALS AND METHOD
Detection of secondary metabolites
Shegilla dysenteriae metabolites were separated
from the liquid culture and evaporated to dryness
with a rotary evaporator at 45Cº. The residue was
dissolved in 1 ml methanol, filtered through a 0.2 μm
syringe filter, and stored at 4ºC for 24 h before being
used for gas chromatography mass spectrometry10-22
.
The identification of the components was based on
comparison of their mass spectra with those of NIST
mass spectral library as well as on comparison of
their retention indices either with those of authentic
compounds or with literature values23-35
.
Materials of Plants Collection and Preparation
In our research, all plant samples were dried at room
temperature for fifteen days and when properly dried the
leaves were powdered using clean pestle and mortar, and
the powdered plant was size reduced with a sieve36-39
.
The fine powder was then packed in airtight container
to avoid the effect of humidity and then stored at room
temperature.
Gas chromatography – Mass Spectrum analysis
Interpretation of mass spectrum was conducted
using the database of National Institute of Standards
and Technology (NIST, USA). The database consists of
more than 62,000 patterns of known compounds. The
spectrum of the extract was matched with the spectrum
of the known components stored in the NIST library.
Shegilla dysenteriae GC–MS analysis were carried out
in a GC system (Agilent 7890A series, USA) 40-42
. The
flow rate of the carrier gas, helium (He) was set to beat 1
mL min−1, split ratio was 1:50. The injector temperature
was adjusted at 250◦C, while the detector temperature
was fixed to280◦C.
Determination of antibacterial and antifungal
activity
Five-millimeter diameter wells were cut from the
agar using a sterile cork-borer, and 25 μl of the plant
samples solutions were delivered into the wells. The
plates were incubated for 48 h at room temperature.
Antimicrobial activity was evaluated by measuring
the zone of inhibition against the test microorganisms.
The studied fungi, Microsporum canis, Streptococcus
faecalis, Aspergillus flavus, Aspergillus fumigatus,
Candida albicans, Penicillium expansum, Trichoderma
horzianum, Aspergillus niger and Aspergillus terreus
were isolated and maintained in potato dextrose agar
slants. Spores were grown in a liquid culture of potato
dextrose broth (PDB) and incubated at 25ºC in a shaker
for 16 days at 130 rpm. The extraction was performed
by adding 25 ml methanol to 100 ml liquid culture in
an Erlenmeyer flask after the infiltration of the culture
43-45
. The antifungal activity was evaluated by measuring
the inhibition-zone diameter observed after 48 h of
incubation.
Data analysis
All the measurements were replicated three times
for each assay and the results are presented as mean ±
SD and mean ± SE. IBM SPSS 20 version statistical
software package was used for statistical analysis of
percentage inhibition and disease incidence and disease
severity in each case.
RESULTS AND DISCUSSION
Gas chromatography and mass spectroscopy
analysis of compounds was carried out in
methanolic extract of Shegilla dysenteriae, shown
in Table 1. Peaks were determined to be 1-Deoxy-
d-mannitol, γ-Thionodecalactone, Hexaborane,
1-Propanamine , 3-(methylthio), 1H-Pyrrole , 1-pentyl,
2-Propanone, 1-(N-cyanomethylimino-), 1-Pentanol
, 5-methoxy, 2-Methyl-4-methoxy-1-butanol,
Benzeneethanamine, 2-Butanamine , (S), L-valine ,
N-glycyl, N-carbobenzyloxy-l-tyrosyl-l-valine, DL-
Isoleucine, and 3-Buten-2-one , 4-(dimethylamino)-
3-[(1-methylethyl). The results of anti-fungal activity
produced by Shegilla dysenteriae showed that the
volatile compounds were highly effective to suppress the
growth of Aspergillus flavus (6.00±0.22) mm, Table 2.
Shegilla dysenteriae produce many important secondary
metabolites with high biological activities. In agar well
diffusion method the selected medicinal plants Ricinus
communis, Datura stramonium, Linum usitatissimum,
Diplotaxis cespitosa, Cassia angustifolia, Celosia
argentea, Apium graveolens, Brassica rapa, Cichorium
endivia, Anethum graveolens, Plantago major, Linum
usitatissimum, A. esculentus, Malva sylvestris, Cordia
myxa, Malva parviflora, Mentha pulegium, Daucus
carota, Vitex agnus-castus, Sambucus nigra, C.
morifolium, Equisetum arvense, Portulaca oleracea,
Malva neglecta, L. angustifolia, Althaea Officinalis, and

454 Indian Journal of Public Health Research & Development, May 2018, Vol. 9, No. 5
Melissa officinalis were effective against Staphylococcus aureus, Table 3. Aspergillus flavus was very highly active
(6.00±0.22) mm against Pseudomonas aeruginosa.
Table 1. Major chemical compounds identified in methanolic extract of Shegilla dysenteriae.
Molecular WeightRT (min)Phytochemical compound
Serial
No.
164.0684743.110Alpha-l-rhamnopyranose1.
166.0841243.1611-Deoxy-d-mannitol2.
186.10783614.949γ-Thionodecalactone3.
76.1340833.482Hexaborane4.
105.061223.8481-Propanamine , 3-(methylthio)-5.
137.1204493.9451H-Pyrrole , 1-pentyl-6.
110.04801274.0882-Propanone, 1-(N-cyanomethylimino-)7.
102.11569834.2371,5-Pentanediamine8.
118.09937954.4321-Pentanol , 5-methoxy-9.
118.09937954.5922-Methyl-4-methoxy-1-butanol10.
248.177634.7462H-Pyran , tetrahydro-2-(2,5-undecadiynyloxy)-11.
121.08914954.941Benzeneethanamine12.
111.10479935.1478-Azabicyclo[5.1.0]octane13.
195.1259295.233Benzenemethanol , 2-(2-aminopropoxy)-3-methyl-14.
97.08914955.5022,5-Dimethyl-1-pyrroline15.
148.0654936.057Cycloheptanol , 2-chloro-,trans-16.
281.0025756.331Phenylhydrazine , 4-nitro-N2-(chloro)(2-thienyl)meth)17.
73.08914956.6922-Butanamine , (S)-18.
174.1004426.955L-valine , N-glycyl-19.
117.05784947.1615H-1-Pyrindine20.
132.0898787.487Ornithine21.
117.07897858.277DL-Valine22.
136.0524299.0492,7-Dioxa-tricyclo[4.4.0.0(3,8)]deca-4,9-diene23.
221.1051939.198Benzenemethanol , α-(2-nitrocyclopentyl)24.
414.1790879.747N-carbobenzyloxy-l-tyrosyl-l-valine25.
338.11149.890N-Carbobenzyloxy-glycylglutamine 26.
594.3682259.988Di-[1,3,2]-oxazino[6,5-f:5’,6’-H]quinoxaline27.
131.09462811.046DL-Isoleucine28.
168.0283412.168Uric acid29.
154.07422712.826Pyrrolo[1,2-a]pyrazine-1,4-dione , hexahydro-30.
154.07422713.592Pyrrolo[1,2-a]pyrazine-1,4-dione , hexahydro-3-(2-me31.
154.17215114.308: 2-Undecene , (Z)32.
230.19942915.046Dihexylamine , N-nitro-33.
170.08037615.704Uracil , 1,3-dimethyl-6-hydrazino-34.
170.14191315.7323-Buten-2-one , 4-(dimethylamino)-3-[(1-methylethyl)35.
184.1463316.362Oxacyclododecan-2-one36.
170.02623216.5568H-[1,2,5]Thiadiazolo[3,4-e][1,4]diazepin-8-one , 437.
226.16812816.7742,5-Piperazinedione , 3,6-bis(2-methylpropyl)-38.
185.14157919.709Methyl 2-diethylamino-3-methyl-but-2-enoate39.
388.1746720.173
L-Prolinamide , 5-oxo-L-prolyl-L-phenylalanyl-4-hydro
40.

Table 2. Antifungal activity of Shegilla dysenteriae metabolite products.
Fungi
Antibiotics / Shegilla dysenteriae metabolite products
Shegilla dysenteriae
metabolite products
Amphotericin B Fluconazol
Miconazole
nitrate
Microsporum canis 2.80±0.18 ª 2.11±0.11 3.06±0.17 2.97±0.17
Streptococcus faecalis 3.01±0.19 3.03±0.16 2.88±0.15 1.81±0.10
Aspergillus flavus 6.00±0.22 2.75±0.12 3.97±0.19 3.06±0.18
Aspergillus fumigatus 5.91±0.21 2.38±0.11 2.76±0.16 2.04±0.16
Candida albicans 5.53±0.19 3.55±0.19 2.85.±0.13 1.85±0.10
Penicillium expansum 4.00±0.17 3.10±0.18 3.02±0.18 1.99±0.10
Trichoderma horzianum 3.87±0.19 1.09±0.09 3.84±0.19 2.98±0.17
Aspergillus niger 5.00±0.19 2.00±0.10 2.95±0.17 2.03±0.15
Aspergillus terreus 4.83±0.18 2.83±0.11 3.07±0.19 3.00±0.18
ª The values ( average of triplicate) are diameter of zone of inhibition at 100 mg/mL crude extract and 30 μg/mL
of (Amphotericin B; Fluconazol and Miconazole nitrate).
Table 3. Zone of inhibition (mm) of test different bioactive compounds and standard antibiotics of
medicinal plants to Shegilla dysenteriae.
Plant
Inhibition
(mm)
Plant
Inhibition
(mm)
Ricinus communis 2.951±0.17 Cordia myxa 2.881±0.16
Datura stramonium 3.617±0.19 Malva parviflora 3.704±0.19
Linum usitatissimum 4.991±0.20 Mentha pulegium 6.100±0.21
Diplotaxis cespitosa 5.984±0.21 Daucus carota 6.953±0.22
Cassia angustifolia 5.977±0.21 Vitex agnus-castus 5.800±0.20
Celosia argentea 3.271±0.18 Sambucus nigra 2.952±0.16
Apium graveolens 4.880±0.20 C. morifolium 5.996±0.20
Brassica rapa 6.274±0.22 Equisetum arvense 5.851±0.21
Cichorium endivia 5.628±0.21 Portulaca oleracea 6.000±0.22
Anethum graveolens 5.749±0.20 Malva neglecta 5.572±0.19
Plantago major 4.951±0.19 L. angustifolia 2.871±0.16
Linum usitatissimum 4.000±0.18 Althaea Officinalis 6.002±0.20
A. esculentus 5.981±0.21 Melissa officinalis 6.704±0.22
Malva sylvestris 6.400±0.22 Control 0.00
CONCLUSION
Forty bioactive chemical constituents have been
identified from methanolic extract of the Pseudomonas
aeruginosa by gas chromatogram mass spectrometry
(GC-MS). In vitro antifungal and antibacterial evaluation
of secondary metabolite products of Pseudomonas
aeruginosa forms a primary platform for further
phytochemical and pharmacological investigation for the
development of new potential antimicrobial compounds.
Financial Disclosure: There is no financial
disclosure.
Conflict of Interest: None to declare.
Ethical Clearance: All experimental protocols

were approved under the Department of Biology, College
of Science, Hillah city, Iraq and all experiments were
carried out in accordance with approved guidelines.
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