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Development of a Melia azedarach L. based natural herbicide: formulation and efficacy studies
(2025-08-01)
Wichittrakarn, Pattharin
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Manichart, Nutcha
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Laosinwattana, Chamroon
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Charoenying, Patchanee
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Sikhao, Potjana
This study evaluated the phytotoxic activity of Melia azedarach L. leaf extract against Echinochloa crus-galli and Phaseolus lathyroides. Crude extracts were obtained using sequential solvent separation, of which the dichloromethane fraction exhibited the highest phytotoxicity for both weed species. However, P. lathyroides appeared more sensitive to the extracts compared to E. crus-galli. GC-MS analysis of the dichloromethane crude extract identified phytol (29.14 %), linolenic acid (21.74 %), and palmitic acid (7.20 %) as the main chemical components. Three formulations, a soluble liquid (SL), pellet, and wettable powder, were developed and evaluated for their effects on seed germination and seedling growth. The SL formulation showed the highest efficacy in inhibiting germination (p < 0.05). Further testing of its pre-emergence utility via soil application in greenhouse conditions confirmed the herbicidal efficacy, effectively suppressing P. lathyroides emergence (36.8 % over control) and reducing growth parameters. Mechanistic assays showed the SL product to affect seed imbibition, α-amylase activity, and cell division in a dose-dependent manner, suggesting these as potential mechanisms of action. This study highlights the potential of a M. azedarach-based SL product as an alternative to synthetic herbicides, potentially leading to the development of a new botanical herbicide.
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Synthesis and Cytotoxicity Evaluation of Novel C-3 Aminocarbamate Pregnenolone Derivatives
(2025-03-06)
Charoenying, Patchanee
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Chotsaeng, Nawasit
Cancer is one of the leading causes of death worldwide. There are many ongoing studies in the search for new treatments or drugs to combat cancer. Similarly, in this research, twelve 3-aminocarbamate pregnenolones (2a–2l) were designed, synthesized, and evaluated for their cytotoxicity against five cancer cell lines: Human hepatocellular carcinoma (HepG2), Human colon adenocarcinoma (HT-29), Human oral cavity carcinoma (KB), Human breast adenocarcinoma (MCF-7), Murine leukemia (P388), and one normal cell line, African green monkey kidney fibroblast (Vero), using the MTT assay. Notably, 3-aminobenzylcarbamate pregnenolone (2b), 3-diaminoheptylcarbamate pregnenolone (2f), and 3-diaminopropanolcarbamate derivative (2i) were the most potent against these cancer cell lines. Specifically, for P388 cell lines, these compounds were more potent than the positive control drug, vinblastine sulfate salt. Results from the SAR study demonstrated that the length of the alkyl chain of diaminocarbamate derivatives was crucial for their anticancer properties. These findings will be useful in the future research and development of anticancer drugs.
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Bioassay-Guided Extraction and Isolation of Natural Herbicides from Dried Zanthoxylum limonella Alston Fruits
(2025-01-01)
Chotpatiwetchkul, Warot
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Charoenying, Patchanee
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Teerarak, Montinee
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Meesin, Jatuporn
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Jongkon, Nathjanan
Weeds are problematic plant species around the world. Various strategies exist for controlling weeds, but chemical treatment remains the preferred method, particularly when using natural substances. In this research, a crude aqueous-methanol extract from dried Zanthoxylum limonella fruits was acid-base partitioned into four fractions: neutral extract (NE), acid extract (AE), basic extract (BE), and aqueous extract (AQ). These fractions were further separated into seventeen subfractions: NEF1 to NEF7, AEF1 to AEF5, and BEF1 to BEF5, which were then tested for herbicidal activity against the growth of Chinese amaranth (Amaranthus tricolor) and barnyard grass (Echinochloa crus-galli). Active subfractions were isolated via column chromatography and identified using spectroscopic methods, yielding seven active compounds: xanthoxyline (1), tambulin (2), atanine (3), prudomestin (4), skimmianine (5), p-methoxybenzoic acid (6), and methyl caffeate (7). Compounds 2–7 had not been previously reported in Z. limonella. Xanthoxyline (1) was identified as the most potent botanical herbicide, fully inhibiting seed germination of Chinese amaranth and barnyard grass. This compound also decreased seed imbibition and α-amylase activity in both species. Molecular docking studies on the α-amylase enzyme (PDB ID: 1BG9) revealed that the aromatic, hydroxy, and carbonyl groups of xanthoxyline (1) interact with the enzyme's active sites.
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Antioxidant and Antibacterial Activities of Jasminum officinale L. f. var. grandiflorum (L.) Kob. Leaf Extracts
(2024-05-01)
Charoenying, Patchanee
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Laosinwattana, Chamroon
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Chotsaeng, Nawasit
The investigation of phytochemicals and their effects on plants is currently receiving significant attention due to the well-known fact that plants contain secondary metabolites that have high levels of usefulness in various applications. These applications include food additives, biopesticides, and pharmaceuticals. In a recent study, we thoroughly examined the total phenolic content (TPC), and the antioxidant, and antibacterial properties of Jasminum officinale L.f. var. grandiflorum (L.) Kob. (also known as Spanish jasmine) leaf extracts, providing valuable insights into its potential benefits. Our study performed a crude methanol (ME) extraction of Spanish jasmine leaves with acid-base solvent partitioning, resulting in an acidic fraction (AE), a neutral fraction (NE), and an aqueous fraction (AQ). The Folin-Ciocalteu method was used to determine the TPC of the extracts. The AE fraction displayed the highest TPC (79.8±0.61 mgGAE/g dry weight), followed by the NE and AQ fractions. The extracts were further evaluated for their antioxidant activity using the DPPH assay. The AE fraction had the highest antioxidant activity with an EC<inf>50</inf> value of 4.6±0.40 µg/mL. The main active compound, oleuropein, was isolated and determined using spectral data. The isolated compound displayed excellent antioxidant activity with an EC<inf>50</inf> value of 13.0±0.06 µg/mL. Moreover, the antibacterial activity of the Spanish jasmine leaf extracts was calculated using the disc diffusion method based on the minimum inhibitory concentration. The AE fraction exhibited activity against the Gram-negative bacteria, Vibrio parahaemolyticus, with a MIC value of 0.78 µg/mL. The AE fraction also displayed the highest degree of activity against Staphylococcus strains, including drug-resistant strains (MRSA and VRSA), with a MIC range of 0.39-12.5 µg/mL. It is important to highlight that the AE fraction demonstrated the highest level of activity against all VRSA strains tested despite their resistance to vancomycin and oxacillin. These findings strongly indicate that Spanish jasmine leaves possess potent natural antioxidant and antibacterial properties, positioning them as a highly promising plant source.
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Structure-Activity Relationship Study of Xanthoxyline and Related Small Methyl Ketone Herbicides
(2022-08-23)
Chotpatiwetchkul, Warot
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Chotsaeng, Nawasit
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Laosinwattana, Chamroon
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Charoenying, Patchanee
Xanthoxyline (1), a small natural methyl ketone, was previously reported as a plant growth inhibitor. In this research, related methyl ketones bearing electron-donating and electron-withdrawing groups, together with heteroaromatics, were investigated against seed germination and seedling growth of Chinese amaranth (Amaranthus tricolor L.) and barnyard grass [Echinochloa crus-galli (L.) Beauv]. The structure-activity relationships (SARs) of methyl ketone herbicides were clarified, and which types and positions of substituents were crucially important for activity were also clarified. Indole derivatives, namely, 3-acetylindole (43) and 3-acetyl-7-azaindole (44) were found to be the most active methyl ketones that highly suppressed plant growth at low concentrations. The molecular docking on the 4-hydroxyphenylpyruvate dioxygenase (HPPD) enzyme indicated that carbonyl, aromatic, and azaindole were key interactions of HPPD inhibitors. This finding would be useful for the development of small ketone herbicides.
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The Allelopathic Activity of Extracts and Isolated from Spirulina platensis
(2022-06-01)
Charoenying, Patchanee
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Laosinwattana, Chamroon
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Chotsaeng, Nawasit
We determined the allelopathic effects of crude organic (hexane, ethyl acetate, and methanol) extracts of the cyanobacterial Spirulina platensis on barnyardgrass (Echinochloa crus-galli (L.) Beauv.) and Chinese amaranth (Amaranthus tricolor L.). The crude ethyl acetate extract showed the highest inhibitory activity and was subsequently fractionated by column chromatography into 23 fractions based on thin-layer chromatography band pattern similarities. Four concentrations (2000, 1000, 500, and 250 ppm) of each fraction were tested for their allelopathic activity. Fractions E6 and E13 exhib-ited the most significant inhibitory effects against Chinese amaranth. The constituents of the highly active E6F3-E6F5 fractions determined by GC-MS, chromatography, and spectroscopy included the fatty acids, γ-linolenic acid 15, oleic acid 12, and predominantly palmitic acid 7; minor constituents included 2-ethyl-3-methylmaleimide 9 and C<inf>11</inf> norisoprenoids (dihydroactinidiolide 10 and 4-oxo-β-ionone 13). Isolation of E13 fraction by column chromatography revealed four C<inf>13</inf> norisoprenoids: 3-hydroxy-β-ionone 17, 3-hydroxy-5α,6α-epoxy-β-ionone 18, 3-hydroxy-5β,6β-epoxy-β-ionone 19, and loliolide 20. Their structures were elucidated by NMR spectroscopy. All six isolated noriso-prenoids inhibited seed germination and seedling growth of Chinese amaranth at concentrations of 250–1000 ppm. Allelochemicals from S. platensis could be utilized in the development of novel bioactive herbicides.
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Allelopathic potential of subfractions from aqueous extract of spirulina platensis and denatured c-phycocyanin
(2022-01-01)
Charoenying, Patchanee
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Laosinwattana, Chamroon
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Chotsaeng, Nawasit
In this laboratory bioassay, crude aqueous extract of Spirulina platensis (Nordst) Geitl. was extracted with 90% aqueous ethanol and 80% aqueous ethanol to achieve three subfractions, green powder (F1), pale-green powder (F2) and deep-blue powder (F3). Each of these subfractions was evaluated for allelopathic activity on Chinese amaranth (Amaranthus tricolor L.) and barnyardgrass (Echinochloa crus-galli (L.) Beauv.). The plant seeds were germinated in vials with three subfractions (250-2000 mg/l concentrations) and distilled water was used as a negative control. The results indicated that subfraction F3 had the highest inhibitory effect on both of the tested plants. All subfractions had an absorbance ratio (A620/A280) lower than the original aqueous extract, suggesting that a denaturation event of the C-phycocyanin (C-PC) component had occurred during the extraction process. After heating a commercial C-PC solution at 90oC for 3 h, the absorbance ratio changed to 0.46, and likewise allelopathic assay revealed that the decolorized C-PC solution retained its allelopathic potential on the tested plants. To confirm these findings, S. platensis powder was extracted with distilled water at 90oC for 3 h and tested for its allelopathic potential using standard Petri dish assay at concentrations of 0.625-5%. The results showed that the hot aqueous extract had an absorbance ratio of 0.38, and its allelopathic activities were similar to those of the aqueous extract. Furthermore, it was found that although C-PC in aqueous extractions denatured, it still retained its allelopathic potential on the tested plants.
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Enantioselective and synergistic herbicidal activities of common amino acids against Amaranthus tricolor and Echinochloa crus-galli
(2021-04-01)
Chotsaeng, Nawasit
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Laosinwattana, Chamroon
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Charoenying, Patchanee
Amino acids have a wide range of biological activities, which usually rely on the stereoiso-mer presented. In this study, glycine and 21 common α-amino acids were investigated for their herbicidal property against Chinese amaranth (Amaranthus tricolor L.) and barnyard grass (Echinochloa crus-galli (L.) Beauv.). Both D-and L-isomers, as well as a racemic mixture, were tested and found that most compounds barely inhibited germination but moderately suppressed seedling growth. Various ratios of D:L-mixture were studied and synergy between enantiomers was found. For Chinese amaranth, the most toxic D:L-mixtures were at 3:7 (for glutamine), 8:2 (for methionine), and 5:5 (for tryptophan). For barnyard grass, rac-glutamine was more toxic than the pure forms; however, D-tryptophan exhibited greater activity than racemate and L-isomer, indicating the sign of enantioselective toxicity. The mode of action was unclear, but D-tryptophan caused bleaching of leaves, indicating pigment synthesis of the grass was inhibited. The results highlighted the enan-tioselective and synergistic toxicity of some amino acids, which relied upon plant species, chemical structures, and concentrations. Overall, our finding clarifies the effect of stereoisomers, and provides a chemical clue of amino acid herbicides, which may be useful in the development of herbicides from natural substances.
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Herbicidal Activity of Flavokawains and Related trans-Chalcones against Amaranthus tricolor L. And Echinochloa crus-galli (L.) Beauv.
(2019-12-10)
Chotsaeng, Nawasit
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Laosinwattana, Chamroon
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Charoenying, Patchanee
Flavokawains have a broad spectrum of biological activities; however, the herbicidal activity of these naturally occurring chalcones has been less investigated. Flavokawains and their analogues were prepared by the Claisen-Schmidt condensation reaction between xanthoxyline (or aromatic ketones) and a variety of aromatic and heteroaromatic aldehydes. These compounds were then evaluated for their inhibitory effect against representative dicot and monocot plants. Among 45 synthetic chalcones, derivatives containing phenoxyacetic acid, 4-(N,N-dimethylamino)phenyl, N-methylpyrrole, or thiophenyl groups inhibited the germination and growth of Chinese amaranth (Amaranthus tricolor L.) with moderate to high degrees compared to commercial butachlor. For barnyardgrass (Echinochloa crus-galli (L.) Beauv.), most of the thiophenyl chalcones interrupted shoot and root emergence. This finding highlighted the importance of functional groups on the herbicidal activity of chalcones. The level of inhibition also depended on the applied concentrations, plant species, and plant organs. (E)-2-(2-(3-Oxo-3-(thiophen-2-yl)prop-1-enyl)phenoxy)acetic acid (14f) was the most active compound among 45 derivatives. This chalcone could be a promising structure for controlling the germination and growth of weeds. The structure-activity relationship results provide useful information about the development of active chalconoids as novel natural product-like herbicides.
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Inhibitory effects of a variety of aldehydes on Amaranthus tricolor l. And echinochloa crus-galli (L.) beauv.
(2018-01-01)
Chotsaeng, Nawasit
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Laosinwattana, Chamroon
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Charoenying, Patchanee
Thirty-seven commercial aldehydes containing aliphatic chains and aromatic rings as well as heteroaromatic rings were evaluated for their inhibitory activities against Chinese amaranth (Amaranthus tricolor L.) and barnyardgrass (Echinochloa crus-galli (L.) Beauv). Polysorbate 80 (Tweenfi 80) was used as a surfactant and the research was preliminarily conducted at 400 µM of all aldehydes. Among these aldehydes, (E)-cinnamaldehyde (7) showed the greatest inhibitory effect on seed germination, shoot and root growth of Chinese amaranth by 54.55%, 75.53%, and 85.13% respectively. Similarly, (E)-crotonaldehyde (5), a related α,β-unsaturated aldehyde, inhibited the germination and seedling growth of the tested species at a high percentage. Apart from these two unsaturated aldehydes, no other aliphatic aldehydes had a harmful effect on Chinese amaranth. In terms of benzaldehyde (6), it had no effect on the tested plant; however, many of its derivatives displayed some inhibitory activity. Furthermore, for the ten common heteroaromatic aldehydes, picolinaldehyde (32) had a high inhibitory effect on Chinese amaranth which closely related to the effect of (E)-crotonaldehyde (5) and (E)-cinnamaldehyde (7), whereas, other heteroaromatic aldehydes showed lower effects. In the case of a monocot plant, barnyardgrass, no tested aldehydes reduced seed germination, however, (E)-cinnamaldehyde (7), 2,4,6-trimethoxybenzaldehyde (16) and 4-(dimethylamino)benzaldehyde (24) could inhibit the seedling growth of the plant with low to moderate levels. The herbicidal effects of the most active aldehydes were then further investigated in order to find the minimum concentration of these aldehydes suppressing the germination and growth of the tested plants. At concentrations as low as 50–100 µM some aldehydes could inhibit the seedling growth of the tested species. The structure-activity relationship (SAR) study reported here demonstrates the chemical clues governing the inhibitory activity of aldehydes which could be utilized in the development of highly effective herbicides in the near future.

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