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Article

Swietenia mahagoni Leaves Extract: Antifungal, Insecticidal, and Phytochemical Analysis

by
Wael M. Khamis
1,
Ahmed A. Heflish
2,
Sarah El-Messeiry
3,
Said I. Behiry
2,*,
Abdulaziz A. Al-Askar
4,
Yiming Su
5,
Ahmed Abdelkhalek
6,* and
Mohamed K. Gaber
7
1
Plant Protection Research Institute, Agriculture Research Center, Al-Sabhia, Alexandria 21616, Egypt
2
Agricultural Botany Department, Faculty of Agriculture (Saba Basha), Alexandria University, Alexandria 21531, Egypt
3
Department of Genetics, Faculty of Agriculture, Alexandria University, Alexandria 21545, Egypt
4
Department of Botany and Microbiology, College of Science, King Saud University, P.O. Box 2455, Riyadh 11451, Saudi Arabia
5
Utah Water Research Laboratory, Department of Civil and Environmental Engineering, Utah State University, Logan, UT 84341, USA
6
Plant Protection and Biomolecular Diagnosis Department, ALCRI, City of Scientific Research and Technological Applications, Alexandria 21934, Egypt
7
Plant Production Department, Faculty of Agriculture (Saba Basha), Alexandria University, Alexandria 21531, Egypt
*
Authors to whom correspondence should be addressed.
Separations 2023, 10(5), 301; https://doi.org/10.3390/separations10050301
Submission received: 18 April 2023 / Revised: 7 May 2023 / Accepted: 8 May 2023 / Published: 9 May 2023
(This article belongs to the Special Issue Natural Plants as Source of Bioactive Compounds: Isolation, Identification and Biological Activity)
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Abstract

:
In this study, we investigated the antifungal properties of an acetone extract derived from the leaves of Swietenia mahagoni (SMAL) against two isolated fungi, Fusarium equiseti (OQ820153) and Rhizoctonia solani (OQ820152), from rice sheath. The extract was effective in inhibiting the growth of both fungi at the highest concentration tested, 3000 μg·mL−1. Laboratory tests on the LC20 of SMAL extract (49.86 mg·L−1) versus pyriproxyfen 10% EC (1.96 mg·L−1) were accomplished on Aphis gossypii Glover. The extract potently reduced the survival of the nymphs (49.58%) more than the other treatments. The longevity of nymphs treated with the extract had the highest prolongation at 9.67 days. The olfactory choice test exhibited the lowest aphid attraction percentage (23.33%). The HPLC of SMAL extract contained various phenolic compounds, and the most abundant found were catechin (752.64 µg·g−1), gallic acid, and chlorogenic acid, as well as flavonoids such as rutin (585.24 µg·g−1) and naringenin. A GC–MS analysis revealed n-hexadecanoic acid (37.1%) as the major compound, followed by oleic acid. These results suggest that SMAL extract has the potential to help plants fight against fungal and insect infections, making it a promising natural and renewable solution for long-term plant pest regulation.

Graphical Abstract

1. Introduction

The capacity to overcome medication resistance and the unpleasant side effects associated with antibiotics has led to a rise in the popularity of medicinal plants and other natural products in the last few years for treating a wide range of pathogenic diseases. Therefore, scientists are investigating new antimicrobial substances that have been used for centuries in alternative medicine. The phytochemical components included in plant extracts make them a less risky and more cost-effective choice. The identification of chemical compounds derived from herbal plants has sparked research into the phytocompounds [1,2,3] responsible for their biological properties.
The Swietenia mahagoni (L.) belongs to the Meliaceae family, which consists mainly of evergreen blooming plants. This family, which has around 50 genera and 550 species, has been widely farmed in South Asia and the Pacific region [4]. A broad variety of diseases are treated using various species from this family’s usage in traditional medicine. The bark of S. mahagoni is used as a spice and in spirits, while its seeds are employed for the treatment of malaria, diabetic complications, autoimmune disorders, viral infections, eating disorders, and hypertension [5]. The therapeutic properties of plants are attributed to their secondary metabolites, which can be used to produce natural antibiotics. The Meliaceae family contains various chemical compounds, including triterpenoids (limonoids), which are more abundant in this family than in others [6]. Over 300 limonoids have been extracted from this family, including seven from the extract of S. mahagoni seeds [7]. Different species of Swietenia contain in their various parts phenolic compounds, triterpenoids (limonoids), flavonoids, swiemahogins A and BC, and alkaloids [8,9].
According to the data from the United States Department of Agriculture (USDA) for the 2021–2022 marketing year, Egypt ranks as the 20th largest producer of rice in the world, with an estimated production of 4.2 million metric tons, out of a worldwide production of 513.85 million metric tons [10]. Sheath blight is an economically significant rice disease worldwide caused by the fungus Rhizoctonia solani and was reported in Egypt early in 2013 [11,12]. A mild pathogen in cereals, Fusarium equiseti is occasionally detected in association with kernels affected by Fusarium head blight [13]. However, recent research has suggested that the F. incarnatum-equiseti species complex may also be associated with the rice sheath rot disease [14]. Meanwhile, Tralamazza et al. [15] have reported that this species complex is associated with panicle infection in wild rice in Brazil. Numerous research studies have explored the effectiveness of different extracts against R. solani, revealing encouraging outcomes regarding their antifungal properties [16,17,18]. Antifungal properties towards the fungi Aspergillus flavus, Candida spp., and A. niger were detected using water, alcohol, ether, and chloroform-derived extracts of S. macrophylla leaves [19]. The methanolic extract of S. mahagoni leaves was shown to be more potent against C. albicans and A. niger when compared to a water-based extract and other solvent extracts [20]. Additionally, the antifungal properties of triterpenoids from Khaya senegalensis and S. mahagoni were investigated by Govindachari et al. [7].
One of the wide-ranging polyphagous insects that exhibit several sophisticated biotypes and plausible distinctions in host adaptation is the cotton aphid, Aphis gossypii Glover (Hemiptera: Aphididae). Its rapid reproduction and high insecticide resistance give rise to economic and ecological problems [21]. Moreover, the susceptibility to secondary infections like sooty mold and virus diseases would be able to accrete in the infected host plants [22]. Oil of mahogany from S. mahagoni showed the potent toxic and repellent effects on the nymphs of the bean aphid, Aphis craccivora Koch (Hemiptera: Aphididae). Therefore, mahogany oil was suggested for the management of bean aphid [23]. One of the commonly used insect growth regulators in the control of piercing-sucking insects is the pyriproxyfen, which proved a superior efficacy in reducing the population of cotton aphid, A. gossypii Glover [24]. This study aimed to isolate and molecularly identify the pathogens responsible for rice sheath blight and rot, examine the antifungal and insecticidal properties of the acetone extract obtained from Swietenia mahagoni leaves (SMAL) against fungal pathogens and the cotton aphid, Aphis gossypii Glover, and determine the primary phytochemical constituents present in the extract through HPLC and a GC–MS analysis.

2. Materials and Methods

2.1. Source of Phytopathogens

The fungal strains used in this study were isolated from rice sheath, morphologically identified at the genus level under a light microscope according to the fungal identification manual [25] and molecularly identified by amplifying the ITS region using the universal primers ITS1 and ITS4 [26]. All the PCR conditions were previously reported [27], and then the PCR products were purified and sequenced using Sanger’s method. The sequences were annotated, a BLAST search was performed on the GenBank portal to identify the tested fungi according to the NCBI database alignment, and then the fungal sequences were deposited in the GenBank database in order to get the accession numbers.

2.2. Preparation of Swietenia Mahagoni Extract

In this study, Swietenia mahagoni leaves were collected in the Alexandria governorate, Egypt, and air-dried for two weeks at 25 °C. The dried leaves were then finely ground into a powder using a grinding mill. One hundred grams of the powdered sample was soaked in 400 mL of 96% acetone for a week, the resulting mixture was filtered, and the S. mahagoni (SMAL) extract was concentrated using a rotary vacuum evaporator. To prepare the concentrations used in the study, all extracts were diluted with dimethyl sulfoxide (DMSO) [28].

2.3. Swietenia Mahagoni Extract (SMAL) Antifungal Activity

The potential of SMAL extract to combat the tested fungi was evaluated using the poisoned food technique [29]. Different concentrations of SMAL extract (1000, 2000, and 3000 μg mL−1) were mixed with potato dextrose agar (PDA) plates and compared to the negative control (PDA supplemented with DMSO). Circular disks (0.5 cm) of the fungi were placed on the PDA plates and incubated at 25 °C for 5 days. The experiment was repeated three times. The percentage of growth inhibition (%) was determined by calculating the effect of the SMAL extract on the hyphal growth of the fungi using the formula [(P − D)/P] × 100, where P represents the length of the fungal growth in the control and D represents the hyphal growth length [30].

2.4. Swietenia Mahagoni Extract (SMAL) Insecticidal Activity

2.4.1. Sampling and Rearing of Cotton Aphid

Samples of cotton aphid, Aphis gossypii Glover individuals, were collected from different regions in Al-Behera governorate. The collected samples of individual cotton aphids were reared on cotton seedlings (variety Giza 86) based on the rearing method performed by Gaimari and Turner [31]. These seedlings were grown in plastic pots (diameter, 10 cm; height, 8 cm) covered with muslin cloth and incubated in a purpose-built growth chamber supplied with a digital thermostat, hygrometer, and automatic shut-off 24 h timer. The aphid’s culture was incubated under rearing conditions of 25 ± 2 °C, 60% RH, and 16 h of light duration. Deteriorated seedlings caused by aphid feeding were replaced whenever needed by new, healthy ones. As the steady growth of aphids increased over time, sufficient quantities of seedlings were gradually introduced into the rearing space. Finally, a laboratory strain (LS) of A. gossypii Glover was obtained after approximately 7 successive generations.

2.4.2. Toxicity Studies

Slide dipping techniques performed by Stirbly et al. [32] were used to evaluate the toxicity of the SMAL extract and pyriproxyfen (Grendo 10% EC, a juvenile hormone analog obtained from Soltaire for Agriculture and Industrial Chemicals Co., Alexandria, Egypt) against A. gossypii Glover. Six gradual concentrations of each treatment were prepared in distilled water. A stereoscopic microscope and fine brush were used to transfer and fix twenty adult females on the upper side of double-faced Scotch tape. The Scotch tape was affixed to one side of a glass slide. Each concentration had three replicated slides that dipped for 10 s. In the control treatment, the slides were dipped in distilled water. The dipped slides were incubated, and the numbers of living and dead aphids were monitored at 24 h of exposure. Thereafter, mortality percentages were corrected based on Abbott’s [33] formula and subjected to a probit analysis [34].

2.4.3. Biological Aspects

A laboratory test was conducted according to the susceptibility test method of the Insecticide Resistance Action Committee (IRAC) [35]. Leaf disks obtained from newly leaves of cotton seedlings were dipped in the solution of each treatment at LC20 as well as distilled water for the control treatment. One leaf disk was placed upon the surface of a 1% solidified agar gel poured into the base of a glass container (diameter, 7 cm; height, 2.5 cm). Twenty newly emerged adult female aphids (LS) were transferred onto the leaf disks. Each container was covered with microholed gauze and fitted with lids. Each treatment was replicated three times. The treatments were incubated under the same previous laboratory conditions. Daily monitoring for the biological aspects was accomplished using a stereomicroscope. The longevity and survival percentages of adult females exposed to the LC20 of each treatment were monitored every 24 h after treatment. The daily production of newly born nymphs was counted to calculate the total reproduction rate per female. On the other hand, twenty of the first 24 h born nymphs from the adult females exposed to the LC20 of each treatment were monitored for their longevity and survival percentage. The total life duration, comprising the longevity of the nymphal and adult stages, was calculated according to Michelotto et al. [36].

2.4.4. Olfactory Response in Triplicate Choice Test

Twenty starved adult aphids were inserted in a central chamber amidst three lateral chambers, which connected with each of them via short tubular passages, according to Jaba et al. [37]. Each lateral chamber hosted 3 g of fresh, tender leaves treated with one of the tested compounds at LC20 versus distilled water in the control. An air compressor was used to blow air through slime hoses attached to each lateral chamber over the hosted leaves. The three-hosted leaves were inserted at the same time. This designed set of olfactometer was replicated three times. The number of aphids attracted to each chamber was recorded each hour up to 4 h. The retention time of aphid individuals required to attain their attraction response in each chamber was calculated at the end of the 4th hr. The equation of the olfactory response was expressed by the following equation, according to Weeks et al. [38] as follows:
Total attraction percentage = (100 × (T + C)/N)
where T is the number of aphides entering the chamber of hosted leaves; C: number of aphides entering the control chamber; N: total number of aphides in the olfactometer set.

2.5. HPLC Analysis

The HPLC instrument used in this study was an Agilent 1260 series, as noted in reference [39]. The column used had dimensions of 4.6 mm (diameter) × 250 mm (length) and a particle size of 5 μm. The mobile phase was composed of H2O (A) and 0.05% CF3COOH in CH3CN (B), and the flow rate was 0.9 mL/min. A stepwise gradient program was utilized to facilitate the separation of sample components. Specifically, from 0 to 5 min, the mobile phase contained 80% solvent A and 20% solvent B; from 5 to 8 min, it changed to 60% solvent A and 40% solvent B; from 8 to 12 min, the mobile phase remained at 60% solvent A and 40% solvent B; from 12 to 16 min, it returned to the initial condition of 82% solvent A and 18% solvent B; and from 16 to 20 min, it remained at 82% solvent A and 18% solvent B. Detection was performed using a multiwavelength detector monitored at 280 nm, with an injection volume of 5 μL and a column temperature of 40 °C. The analyzed compounds (standards) included 17 common phenolic and flavonoid components: apigenin, caffeic acid, catechin, chlorogenic acid, cinnamic acid, coumaric acid, daidzein, ellagic acid, ferulic acid, gallic acid, methyl gallate, naringenin, pyrocatechol, quercetin, rutin, syringic acid, and vanillin.

2.6. Gas Chromatography–Mass Spectrometry (GC–MS) Analysis

In this study, an Agilent 7000D GC–MS (Agilent technologies, Santa Clara, CA, USA) was used with a 5% diphenyl/95% dimethylpolysiloxane column packed with an HP-5MS capillary column. Pure helium gas (99.99%) was used as the carrier gas at a flow rate of 1 mL/min. The ionization energy was set at 70 eV, and the scan time was 0.2 s. The fragment range was set between 40 to 600 m/z. For each injection, 1 μL of the sample was used, with a split ratio of 10:1. The injector temperature was constant at 250 °C. The column oven temperature was set at 50 °C for 3 min, raised at 10 °C per min up to 280 °C, and then increased to 300 °C for 10 min. The identification of phytochemicals was based on the comparison of their retention time, peak area, and mass spectral patterns with those of authentic compounds stored in the mass spectral Wiley registry 8E, replib, and mainlib libraries.

2.7. Statistical Analyses

The obtained data were subjected to an analysis of variance (ANOVA), and means were compared using the LSD test for significance at 0.05 using SAS software [40].

3. Results

3.1. The Process of Isolating and Identifying Fungal Strains

After examining the isolation trails from the sheath of the rice plant, two pathogens were recovered. Upon initial identification using a light microscope, they were confirmed to be Fusarium and Rhizoctonia species. To further characterize these fungi, we performed a molecular analysis by sequencing the amplified ITS region. The resulting sequences were then compared to those in the Genbank portal, which revealed a homology of 100% with Fusarium equiseti and Rhizoctonia solani. To make these findings publicly available, we deposited the sequences of the two fungal organisms in the NCBI database under the accession numbers OQ820153 for F. equiseti and OQ820152 for R. solani.

3.2. Effect of the SMAL Extract on the Fungal Pathogens

Table 1 presents data on the in vitro growth inhibition percentage of two plant pathogenic fungi, Rhizoctonia solani and Fusarium equiseti, in response to different concentrations of Swietenia mahagoni leaf (SMAL) extract.
The results show that increasing the concentration of the leaf extract led to a higher inhibition percentage for both fungal strains. At a concentration of 1000 μg·mL−1, R. solani had an inhibition percentage of 18.21%, while F. equiseti had an inhibition percentage of 37.86%. At 2000 μg·mL−1, R. solani had a higher inhibition percentage of 53.22%, while F. equiseti had a slightly lower inhibition percentage of 36.07%. However, at the highest concentration tested (3000 μg·mL−1), both fungal strains had a high inhibition percentage of 77.50% and 82.50%, respectively. The control group (Nc, DMSO) did not show any inhibition of fungal growth, indicating that the observed effects were due to the SMAL extract and not any other factors. However, the data suggested that the SMAL extract had antifungal properties and could inhibit the growth of R. solani and F. equiseti in vitro.

3.3. Toxicity of the SMAL Extract on the Adults of Cotton Aphids

Toxicity studies were conducted to calculate the values of the LC20 and LC50 of the tested plant extracts in comparison to pyriproxyfen 10% EC, on the adult stage of Aphis gossypii Glover (LS) at 24 h of exposure under laboratory conditions (Table 2). Pyriproxyfen 10% EC showed the highest toxicity values of 4.18 and 1.96 mg·L−1, which transcended the Swietenia mahagoni extract toxic values of 197.70 and 49.86 mg·L−1 at LC50 and LC20, respectively.

3.4. Biological Aspects of Adult Females and Nymphal Stages of Aphis Gossypii Glover

Data of the reproduction activity of adult females and survival percentages of the developmental stages of A. gossypii Glover along their longevity period were evaluated under the exposure to the LC20 of the tested compounds (Table 3). Swietenia mahagoni extract had a potent effect that significantly reduced the survival percentages of the nymphal stage (49.58%), more than pyriproxyfen 10% EC (61.67%) and the control treatment (98.57%). All the tested compounds had no significant differences on the survival percentages of adult female stage. SMAL extract and pyriproxyfen 10% EC had equipollent effects that exceeded the control treatment in reducing the daily and total nymph production in addition to the reproductive period of the adult female.

3.5. Longevity of Developmental Stages and Total Life Duration of Aphis Gossypii Glover (LS)

The obtained data of the tested compounds at LC20 showed biological effects on the longevity of the adult and nymphal stages of A. gossypii Glover (LS) and consequently on its total life duration (Table 4). The results of the longevity of adults had no significant differences between all treatments, whilst nymphs treated with the SMAL extract had the highest prolongation of their longevity (9.67 days), more than pyriproxyfen 10% EC (8.67 days) in comparison to the control (7.00 days). Both SMAL extract and pyriproxyfen 10% EC had an equipollent prolongation for the total life duration at 15.67 and 14.33 days, respectively, in comparison to the control at 12.67 days.

3.6. Olfactory Response on the Adult Stage of Aphis Gossypii Glover

The lateral chamber that hosted the leaves treated with the SMAL extract possessed the lowest attraction percentage on aphid individuals (23.33%) compared to pyriproxyfen 10% EC (35.00%), which was on a par with the response of the control (40.00%). All the treatments had no significant differences for the retention times (Rt) of the submitted aphid individuals to achieve their attraction response over 4 h of exposure (Figure 1).

3.7. Swietenia Mahagoni Extract’s Polyphenolic Content

Table 5 provides a list of the phenolic and flavonoid components detected in the Swietenia mahagoni leaf (SMAL) extract, along with their respective areas and concentrations measured in µg·g−1 (Figure 2). Phenolic compounds are secondary metabolites widely distributed in plants that are important for their antioxidant and medicinal properties. The SMAL extract contained a variety of phenolic compounds, including gallic acid, chlorogenic acid, methyl gallate, caffeic acid, syringic acid, ellagic acid, coumaric acid, vanillin, ferulic acid, and cinnamic acid. The highest concentration of catechin was found at 752.64 µg·g−1, followed by gallic acid at 690.54 µg·g−1 and chlorogenic acid at 471.15 µg·g−1.
Flavonoids are a subclass of phenolic compounds that are widely distributed in plants and have been shown to have numerous health benefits. The SMAL extract contained several flavonoids, including rutin, naringenin, daidzein, and hesperetin. The highest concentration of rutin was found at 585.24 µg·g−1, followed by naringenin at 82.18 µg·g−1 (Table 5). Notably, some compounds such as pyro catechol, querectin, apigenin, and kaempferol were not detected in the extract. It is possible that these compounds were present in concentrations below the detection limit of the instrument used in this analysis.

3.8. Swietenia Mahagoni (SMAL) Extract’s GC–MS Content

The GC–MS chromatogram of the acetone leaf extract of Swietenia mahagoni (SMAL) recorded a total of 14 peaks corresponding to the bioactive compounds that were recognized by relating their peak retention time, relative abundance area (%), and compound class to that of the known compounds described by different mass spectral libraries (Figure 3). Overall, all the phytocompounds identified in the SMAL extract are presented in Table 6. The GC–MS analysis of the SMAL extract revealed the presence of several classes of compounds, including fatty acid derivatives, epoxy fatty acid esters, saturated and unsaturated fatty acids, triterpenoids, alkaloid derivatives, and a triacylglycerol. The major compounds identified were n-hexadecanoic acid, which accounted for 37.1% of the total area, and oleic acid, which accounted for 19.05% of the total area. 9,12-octadecadienoic acid and friedelan-3-one were also present in significant amounts, accounting for 6.24%, and 8.08% of the total area, respectively (Table 6).

4. Discussion

In recognition of their reliability, strength, ecological nature, and sustainable impact on the ecosystem, plant-based substances, particularly medicinal plants, have been introduced in the environmental field to treat various plant diseases. In addition, such substances may mitigate the negative effects of synthetic antimicrobials [41]. In the present investigation, qualitative evaluations of the bioactive substances in the acetone extract of Swietenia mahagoni leaves (SMAL) were performed using a variety of conventional assays, displaying the presence of a vast array of phytochemical components. The most significant biologically active substances were rutin, gallic acid, catechin, hexadecanionic acid, oleic acid, and triterpenes. These results are consistent with those of other investigators [42,43], and these molecules play a major role in the treatment of various plant pathogens. Chen et al. [9] explored the association among the botanical compound substances in the plant extract and its biological capability.
A study was conducted to investigate the antifungal properties of the methanolic extract obtained from the leaves of S. mahagoni (methSM). The study showed that fungal strains such as Candida albicans, Aspergillus flavus, and A. niger were highly susceptible to the extract at concentrations of 25 and 50 mg·mL−1, with inhibition zones (IZ) ranging from 12.0 to 22.1 mm. However, less activity was observed at a concentration of 15 mg·mL−1, with IZ ranging from 9.5 to 13.1 mm. Conversely, no antifungal activity was observed against A. fumigatus and C. glabrata [44]. However, our promising antifungal results are consistent with those obtained by previous studies, which showed that the methSM extract was effective against C. albicans and A. niger at a concentration of 100 mg·mL−1, with IZ ranging from 16 to 20 mm [20]. Other studies have also reported the antifungal properties of S. mahagoni and macrophylla methanol seed extract against C. albicans, Rhizopus spp., Fusarium, and Alternaria species [45,46].
The most potent molecules found in our SMAL-HPLC and GC–MS analyses, such as catechin, gallic acid, ferulic acid, and hexadecanoic acid have been studied for their antibacterial and antifungal properties [47,48,49]. The SMAL extract’s detected molecules (e.g., coumaric, caffeic, and ferulic acids) were found to have antifungal activity against Alternaria alternata when applied alone or synergistically [47]. Moreover, in contrast, the second constituent in SMAL’s GC–MS, oleic acid (monoene fatty acid), did not have a significant effect on the growth of R. solani or Pythium avenae but did reduce the mycelial growth of P. ultimum [50].
However, a sublethal concentration (LC20) of SMAL extract significantly decreased the survival percentages of A. gossypii Glover nymphs, with no discernible influence on the adult survival percentages. Certain HPLC–MS phytochemical components of Swietenia mahagoni extract, such as derivatives of dihydro-p-coumaric, cinnamic acid, and 7-hydroxycoumarin, may be one of the primary sources of toxic effects and viable insecticidal activities [51,52,53]. In addition, the SMAL extract was distinguished by derivatives of quercetin, in which it attained a good affinity on the active site of acetylcholinesterase but with a lower binding energy compared to chlorpyrifos against insect pests of the Hemiptera, Diptera, and Lepidoptera. On the contrary, quercetin was almost safe for natural enemies of Coleoptera and pollinators of Hymenoptera [54,55]. Moreover, the SMAL extract in this study featured derivatives of caffeic acid. Sequential binding of multiple molecules of caffeic acid was shown to possess a potent inhibitor of Helicoverpa armigera Hubner gut proteases’ activity and gene expression [56]. Ultimately, some of the moieties of the SMAL extract might share only a synergistic action, for instance, the synergistic effects of the derivatives of chlorogenic acid on quercetin [55], vanillin mixtures with imidacloprid or α-cypermethrin [57], and daidzein on the baculovirus biopesticide [58]. Moreover, the hesperidin–Mg complex was found to be a trigger for the insecticide’s potential against the adults of Bemisia tabaci Gennadius and Spodoptera frugiperda (J.E. Smith) [59]. On the other hand, the unsaturated free carboxylic fatty acids detected by GC–MS in the SMAL extract, exemplified in oleic acid, n-hexadecanoic acid, 9,12-octadecadienoic acid (Z,Z), and trans-13-octadecenoic acid, were thought to attain an insecticidal activity against A. gossypii Glover. These findings are in accordance with the investigations on the insecticidal activity of corresponding fatty acids on lepidopteran pests, such as S. littoralis Boisd. [60,61], Earias insulana Boisd. [62], and the hemipteran, A. gossypii Glover [63]. This phenomenon could be elucidated by the inferences of Eldesouky et al. [60] and Khamis et al. [61] stating that the ascendancy of the larvicidal activity against S. littoralis Boisd was correlated with the increases in the double-bond quantities in the fatty acid chains. Furthermore, the free carboxylic fatty acids could accomplish more toxicity than their methylated ones, as the free carboxyl group had a high tendency to obstruct the systemic constancy of target cells [61,64].
In this study, both the SMAL extract and pyriproxyfen realized equally prolonging effects on the longevity of the nymphal stages of A. gossypii Glover and its whole life duration. The LC20 of the SMAL extract and pyriproxyfen had equipollent effects on reducing the reproductive activity of the adult female more than the control. The biological aspects of the SMAL extract on cotton aphids may be attributed to particular HPLC–MS components that were investigated in several research studies. For instance, in polyphenols, gallic acid was found to exhibit antifeeding effects via jasmonic acid signals, which induced astragalin, naringenin, and epigallocatechin-3-gallate [65]. In addition, ellagic acid adversely increased larval mortality, reduced pupation, and prolonged the development of the immature stages of S. litura Fabricius [66]. Moreover, naringenin and quercetin increased the developmental duration, the pre-reproductive period, and mortality, while decreasing fecundity and the reproduction rate of the pea aphid, Acyrthosiphon pisum Harris.
In our study, the SMAL extract possessed a repellent response on the adult stage of A. gossypii compared to pyriproxyfen and the control treatment. The explication of these findings may be associated with the presence of specific HPLC–MS phytochemical moieties in the SMAL extract represented in pyrocatechol, catechin, and gallic acid [65,67,68]. The repellency and insecticidal activity of 1,2-benzenediol (pyrocatechol) were observed on insects due to the presence of two hydroxyl groups in the ortho-position [68]. Flavonoid derivatives, (+)-catechin, showed no fatal effects but potent repellency and antifeedant activity against Coptotermes curvignathus Holmgren (Isoptera: Rhinotermitidae) [67]. Gallic acid could induce the direct defense of Camellia sinensis against the larvae of Ectropis oblique, via stimulating the signals of jasmonic acid and the pathways of phenylpropanoid [65].
Overall, our data suggest that the tested compound has potential as a natural fungicide against R. solani and F. equiseti. Moreover, an insecticide could be used to kill cotton aphids. However, further studies are needed to determine the mechanism of action and potential applications of the tested extract in agriculture.

5. Conclusions

In summary, this study evaluated the antifungal and insecticidal properties of an acetone extract of Swietenia mahagoni leaves (SMAL). The extract showed a partial activity against the fungal growth of Rhizoctonia solani and was more potent toward Fusarium equiseti in vitro. The SMAL extract possessed plausible toxic effects on Aphis gossypii Glover. This extract potently reduced the survival percentages of the nymphs. It had obvious reductions in the nymph production and the reproductive period of the adult females. Additionally, the SMAL extract could attain the highest prolongation in the longevity of nymphs and the total life duration. Moreover, it exhibited the lowest attraction percentage in the olfactory choice test on the adult aphids. Therefore, the SMAL extract may be rationally included as part of the cotton aphid control programs. According to the HPLC and GC–MS analyses, the SMAL extract was found to contain high levels of catechin, gallic acid, rutin, n-hexadecanoic acid, and oleic acid. The results suggest that the SMAL extract could be a potential natural and renewable product to regulate plant infestation by fungi and A. gossypii Glover and could be used as a long-term approach instead of insecticides that negatively affect human health and the environment.

Author Contributions

Conceptualization, methodology, software, and investigation W.M.K., A.A.H., S.E.-M., A.A., A.A.A.-A., Y.S., S.I.B. and M.K.G.; writing—original draft preparation, W.M.K., A.A. and S.I.B.; project administration, A.A. and A.A.A.-A.; funding acquisition, A.A.A.-A. All authors have read and agreed to the published version of the manuscript.

Funding

This research was financially supported by the Researchers Supporting Project number. (RSP2023R505), King Saud University, Riyadh, Saudi Arabia.

Institutional Review Board Statement

Not applicable.

Informed Consent Statement

Not applicable.

Data Availability Statement

Not applicable.

Acknowledgments

The authors express their sincere thanks to the City of Scientific Research and Technological Applications (SRTA-City) and the Faculty of Agriculture (Saba Basha), Alexandria University, Egypt, for providing the necessary research facilities. The authors would like to extend their appreciation to the Researchers Supporting Project number (RSP2023R505), King Saud University, Riyadh, Saudi Arabia.

Conflicts of Interest

The authors declare no conflict of interest.

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Separations 10 00301 g001 550
Figure 1. Attraction percentages of the adults of Aphis gossypii Glover (LS) at the 4th hr of exposure to the tested compounds at LC20 in the olfactory choice test. 1 SD = standard deviation. 2 Rt = retention time (h). Means of attraction percentages and retention times followed by the same letters are not significantly different according to the LSD0.05.
Figure 1. Attraction percentages of the adults of Aphis gossypii Glover (LS) at the 4th hr of exposure to the tested compounds at LC20 in the olfactory choice test. 1 SD = standard deviation. 2 Rt = retention time (h). Means of attraction percentages and retention times followed by the same letters are not significantly different according to the LSD0.05.
Separations 10 00301 g001
Separations 10 00301 g002 550
Figure 2. Polyphenolic content detected in Swietenia mahagoni extract.
Figure 2. Polyphenolic content detected in Swietenia mahagoni extract.
Separations 10 00301 g002
Separations 10 00301 g003 550
Figure 3. Phytoconstituents detected in the acetone leaf extract of Swietenia mahagoni using gas chromatography–mass spectrometry.
Figure 3. Phytoconstituents detected in the acetone leaf extract of Swietenia mahagoni using gas chromatography–mass spectrometry.
Separations 10 00301 g003
Table
Table 1. In vitro growth inhibition percentage (%) of plant pathogenic fungi in response to Swietenia mahagoni leaf extract.
Table 1. In vitro growth inhibition percentage (%) of plant pathogenic fungi in response to Swietenia mahagoni leaf extract.
Treatments of Swietenia mahagoni Acetone Extract Conc. (μg·mL−1)Inhibition Percentage (%)
Rhizoctonia solaniFusarium equiseti
100018.21 c37.86 b
200053.22 b36.07 bc
300077.50 a82.50 a
* Nc0.00 d0.00 c
* Nc = negative control (DMSO). The different letters in each column mean the data were significantly different according to the LSD test at a 0.05 level of probability.
Table
Table 2. Toxicity of the tested compounds on adult Aphis gossypii Glover (LS) at 24 h of exposure.
Table 2. Toxicity of the tested compounds on adult Aphis gossypii Glover (LS) at 24 h of exposure.
Tested CompoundLethal Concentration (mg·L−1)Confidence Limits (mg·L−1)Slope ± SE **χ2 ***dfN ****
Swietenia mahagoni acetone extractLC2049.86(30.57–72.21)0.42 ± 0.059.794360
LC50197.70(155.12–251.96)
Pyriproxyfen10% ECLC201.96(1.62–2.38)0.71 ± 0.117.944360
LC504.18(3.67–4.77)
** Standard error, *** chi square, **** total numbers of aphids submitted to the toxicity test.
Table
Table 3. Effects of the LC20 of the tested compounds on the reproduction activity of the female and the survival percentages of the born nymphs of Aphis gossypii Glover (LS).
Table 3. Effects of the LC20 of the tested compounds on the reproduction activity of the female and the survival percentages of the born nymphs of Aphis gossypii Glover (LS).
TreatmentsNymph Production/Female (Days) ± SD 1Reproductive Period (Days) ± SDTotal Mean of Survival% ± SD 1
DailyTotalAdult StageNymphal Stage
Swietenia mahagoni acetone extract0.38 b ± 0.301.50 b ± 0.302.33 b ± 0.5862.36 a ± 13.9649.58 c ± 3.82
Pyriproxyfen 10% EC0.50 b ± 0.582.01 b ± 0.583.00 ba ± 0.0067.92 a ± 4.0261.67 b ± 1.44
Control3.94 a ± 1.5515.77 a ± 1.553.67 a ± 0.5876.33 a ± 5.9398.57 a ± 1.43
1 SD = standard deviation. Means of data in each column followed by the same letters are not significantly different according to the LSD0.05.
Table
Table 4. Effects of the LC20 of the tested compounds on the longevity of the developmental stages and the total life duration of Aphis gossypii Glover (LS).
Table 4. Effects of the LC20 of the tested compounds on the longevity of the developmental stages and the total life duration of Aphis gossypii Glover (LS).
TreatmentsLongevity (Days) ± SD 1Total Life Duration (Adult + Nymph) (Days) ± SD 1
Adult StageNymphal Stage
Swietenia mahagoni acetone extract6.00 a ± 0.009.67 a ± 0.5815.67 a ± 0.58
Pyriproxyfen 10% EC5.67 a ± 0.588.67 b ± 0.5814.33 a ± 1.15
Control5.67 a ± 0.587.00 c ± 0.0012.67 b ± 0.58
1 SD = standard deviation. Means of data in each column followed by the same letters are not significantly different according to the LSD0.05.
Table
Table 5. Phenolic and flavonoid components detected in Swietenia mahagoni extract.
Table 5. Phenolic and flavonoid components detected in Swietenia mahagoni extract.
CompoundsAreaConcentration (µg·g−1)
Gallic acid94.29690.54
Chlorogenic acid39.46471.15
Catechin34.57752.64
Methyl gallate51.39316.17
Caffeic acid11.0889.01
Syringic acid14.44128.93
Pyro catechol* ndnd
Rutin59.82585.24
Ellagic acid8.79146.29
Coumaric acid15.4640.62
Vanillin11.4058.30
Ferulic acid17.00119.16
Naringenin8.3282.18
Daidzein5.5327.91
Querectinndnd
Cinnamic acid15.5740.34
Apigeninndnd
Kaempferolndnd
Hesperetin4.4132.51
* nd = not detected.
Table
Table 6. GC–MS analysis of the acetone leaf extract of Swietenia mahagoni.
Table 6. GC–MS analysis of the acetone leaf extract of Swietenia mahagoni.
* RT (min)Relative Abundance %CompoundCompound Class
24.031.01Methyl 11,14-eicosadienoateFatty acid derivative
25.642.35Oxiraneundecanoic acid, 3-pentyl-,methyl esterEpoxy fatty acid ester
26.3537.1n-Hexadecanoic acidSaturated fatty acid
28.164.4Palmitic acidSaturated fatty acid
29.346.249,12-Octadecadienoic acidPolyunsaturated fatty acid
29.4919.05Oleic acidMonounsaturated fatty acid
31.242.24Glycidyl oleateEpoxy fatty acid ester
33.932.31α-N-NormethadolOpioid derivative
34.071.94Oleic anhydrideFatty acid derivative
40.138.08Friedelan-3-oneTriterpenoid
43.974.65Strychane 1-acetyl-20α-hydroxy-16-methyleneAlkaloid derivative
45.213.22TrilinoleinTriacylglycerol
45.512.08LupeolTriterpenoid
* RT = Retention time.
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Khamis, W.M.; Heflish, A.A.; El-Messeiry, S.; Behiry, S.I.; Al-Askar, A.A.; Su, Y.; Abdelkhalek, A.; Gaber, M.K. Swietenia mahagoni Leaves Extract: Antifungal, Insecticidal, and Phytochemical Analysis. Separations 2023, 10, 301. https://doi.org/10.3390/separations10050301

AMA Style

Khamis WM, Heflish AA, El-Messeiry S, Behiry SI, Al-Askar AA, Su Y, Abdelkhalek A, Gaber MK. Swietenia mahagoni Leaves Extract: Antifungal, Insecticidal, and Phytochemical Analysis. Separations. 2023; 10(5):301. https://doi.org/10.3390/separations10050301

Chicago/Turabian Style

Khamis, Wael M., Ahmed A. Heflish, Sarah El-Messeiry, Said I. Behiry, Abdulaziz A. Al-Askar, Yiming Su, Ahmed Abdelkhalek, and Mohamed K. Gaber. 2023. "Swietenia mahagoni Leaves Extract: Antifungal, Insecticidal, and Phytochemical Analysis" Separations 10, no. 5: 301. https://doi.org/10.3390/separations10050301

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