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Introduction
Heterocyclic 1,2 nuclei are crucial building blocks for the development of numerous therapeutic medicines and play a significant role in medicinal chemistry. The central core of numerous significant biological molecules known as chalcones is an aromatic ketone. The α,β-unsaturated carbonyl system of chalcones and its analogues is recognized as a crucial framework and has been used as a precursor for molecules with physiological activity. The parent compound in the chalcone series is benzylidene acetophenone. Chalcones3,4,5,6,7,8 are the biogenetic precursors of flavonoids and isoflavonoids ,the natural and synthetic products that have been reviewed for their wide range of pharmacological activity9,10, medicinal11,12, and agricultural activities. Literature survey also reveals various biological activities13,14,15,16 like antibacterial17,18,19, antioxidant20, antifungal21,22,23,24,25,26, tubulin polymerisation inhibitors27, potent antitumor activity28, antimalarial agent29, antimicrobial30,31,32, anticancer33,34,35, antitubercular36, anti-infective properties37 in-vivo38, as well as in-vitro conditions39.
Plant pathology is the study of the causes, progression, and management of plant diseases. Plant diseases can be brought on by environmental factors or pathogenic organisms like fungi, bacteria, viruses, etc. Plants suffering from these diseases may grow more slowly or even die. Fungi were the first class of agents identified as causing plant diseases.
Materials and Methods
In our previous work, a series of novel substituted chalcones40 (listed in Table 1) were prepared by treating different aromatic aldehydes with different substituted acetophenones in presence of ethyl alcohol and aqueous potassium hydroxide (KOH) solution. These synthesized compounds were characterized by IR and 1H NMR spectra and assayed for their antibacterial activities. In continuation with our previous work, we undertake the antifungal activities these compounds.
Table 1: List of Synthesized Chalcones.
|
Sr No |
Code |
Synthesized Chalcones |
|
1 |
AM1 |
3-(2,3-Dichlorophenyl)-1-(4-methylphenyl)prop-2-en-1-one |
|
2 |
AM2 |
3-(4-Fluorophenyl)-1-phenylprop-2-en-1-one |
|
3 |
AM3 |
1-(2,4-Dihydroxyphenyl)-3-(3-nitrophenyl)prop-2-en-1-one |
|
4 |
AM4 |
1-(4-Methylphenyl)-3-(3-nitrophenyl)prop-2-en-1-one |
|
5 |
AM5 |
3-(4-Methoxyphenyl)-1-phenylprop-2-en-1-one |
|
6 |
AM6 |
1-(4-Bromophenyl)-3-(4-hydroxyphenyl)prop-2-en-1-one |
|
7 |
AM7 |
3-(4-Methoxyphenyl)-1-(4-methylphenyl)prop-2-en-1-one |
|
8 |
AM8 |
1-(4-Bromophenyl)-3-phenylprop-2-en-1-one |
|
9 |
B4 |
1-(3-Aminophenyl)-3-(4-chlorophenyl)prop-2-en-1-one |
|
10 |
G |
3-(4-Hydroxyphenyl)-1-(4-methylphenyl)prop-2-en-1-one |
|
11 |
H |
3-(2,3-Dichlorophenyl)-1-(2,4-dihydroxyphenyl)prop-2-en-1-one |
|
12 |
I |
3-(4-Chlorophenyl)-1-(4-methylphenyl)prop-2-en-1-one |
|
13 |
J |
1-(3-Aminophenyl)-3-(2,3-dichlorophenyl)prop-2-en-1-one |
|
14 |
K |
3-(2,3-Dichlorophenyl)-1-(4-methylphenyl)prop-2-en-1-one |
|
15 |
L |
3-(3-Nitrophenyl)-1-phenylprop-2-en-1-one |
|
16 |
M |
1-(3-Methylphenyl)-3-phenylprop-2-en-1-one |
|
17 |
N |
3-(4-Nitrophenyl)-1-phenylprop-2-en-1-one |
|
18 |
O |
1-(4-Bromophenyl)-3-(4-methoxyphenyl)prop-2-en-1-one |
|
19 |
P |
3-(4-Chlorophenyl)-1-(2,4-dihydroxyphenyl)prop-2-en-1-one |
Results
The synthesized chalcone derivatives were screened for their antifungal assay against some ornamental plant pathogens viz. Candida albicans, Trichophyton rubrum, Aspergillus niger, and Trichophyton mentagoforum.
Table 2: Impact of test compounds against plant pathogens (Fungi).
|
Test Compound |
Candida albicans |
Trichophyton rubrum |
Aspergillus Niger |
Trichophyton mentagoforum |
|
Compound 1 |
20mm |
16 mm |
19 mm |
20 mm |
|
Compound 2 |
19 mm |
— |
20 mm |
22 mm |
|
Compound 3 |
15 mm |
20 mm |
23 mm |
24 mm |
|
Compound 4 |
21 mm |
19 mm |
21 mm |
23 mm |
|
Compound 5 |
14 mm |
18 mm |
16 mm |
25 mm |
|
Compound 6 |
19 mm |
18 mm |
— |
26 mm |
|
Compound 7 |
— |
15 mm |
— |
28 mm |
|
Compound 8 |
15 mm |
— |
— |
— |
|
Compound 9 |
14 mm |
20 mm |
20 mm |
13 mm |
|
Compound 10 |
16 mm |
22 mm |
— |
22 mm |
|
Compound 11 |
— |
18 mm |
20 mm |
17 mm |
|
Compound 12 |
20 mm |
— |
18 mm |
22 mm |
|
Compound 13 |
18 mm |
20 mm |
— |
21 mm |
|
Compound 14 |
18 mm |
22 mm |
— |
18 mm |
|
Compound 15 |
21 mm |
18 mm |
17 mm |
24 mm |
|
Compound 16 |
19 mm |
17 mm |
20 mm |
17 mm |
|
Compound 17 |
20 mm |
19 mm |
18 mm |
16 mm |
|
Compound 18 |
13 mm |
18 mm |
— |
18 mm |
|
Compound 19 |
— |
20 mm |
21 mm |
21 mm |
|
Reference Antibiotic |
38 mm (Fluconazole) |
39 mm (Fluconazole) |
16 mm (Fluconazole) |
18 mm (Fluconazole) |
|
Control Disc (Chloroform) |
— |
— |
— |
— |
Diameter of inhibition zone (mm)
Discussion
The synthesized compounds listed in Table 1, when assayed against the ornamental plant pathogens (fungi) viz. C.albicans, T.rubrum, A.niger, and T.mentagoforum showed moderate to excellent activities.
 |
Figure 1: Pictorial presentation of the Impact of test compounds against experimented organisms |
In general, compounds in Table 2 showed good antifungal actions against all the test organisms viz. C.albicans, T.rubrum, A.niger, and T.mentagoforum. In general, test compounds 4, 15 and 16 showed very good activities against all the experimented organisms viz C.albicans, T. rubrum, A. niger, and T. mentagoforum. All the test compounds had shown comparatively excellent inhibitory activities against T. mentagoforum. The test compound 4 showed excellent antifungal activity against C.albicans. The test compounds10 and 14 were very active against T. rubrum. The test compound 3 showed very good activity against A. niger. The test compounds 6 and 7 showed excellent activity against T. mentagoforum. In case of A.niger, and T.mentagoforum, some test compounds showed higher antifungal actions than reference antibiotic Fluconazole.
 |
Figure 2: Graphical representation of the Impact of test compounds against plant pathogens viz Candida albicans and Trichophyton rubrum. |
 |
Figure 3: Graphical representation of the Impact of test compounds against plant pathogens viz Aspergillus niger and Trichophyton mentagoforum |
Conclusion
Most of the test compounds were found to be highly active against the experimented fungi viz. C.albicans, T.rubrum, A.niger, and T.mentagoforum. Hence, all of these test compounds can be employed to treat diseases in ornamental plants brought on by these pathogens. Yet, it is advisable to do a more in-depth investigation in light of agricultural sciences.
Acknowledgement
The authors are grateful to Amolakchand Mahavidyalaya, Yavatmal for providing all the necessary facilities to carry out synthetic work. Samruddhi Microbial Diagnostic Lab., Amravati, Maharashtra for providing antifungal activities.
Conflict of Interest
There are no conflict of interest.
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