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Bioassay-Guided Extraction and Isolation of Natural Herbicides from Dried Zanthoxylum limonella Alston Fruits
(2025-01-01)
Chotpatiwetchkul, Warot
;
Charoenying, Patchanee
;
Teerarak, Montinee
;
Meesin, Jatuporn
;
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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Enantioselective and synergistic herbicidal activities of common amino acids against Amaranthus tricolor and Echinochloa crus-galli
(2021-04-01)
Chotsaeng, Nawasit
;
Laosinwattana, Chamroon
;
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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Inhibitory effects of a variety of aldehydes on Amaranthus tricolor l. And echinochloa crus-galli (L.) beauv.
(2018-01-01)
Chotsaeng, Nawasit
;
Laosinwattana, Chamroon
;
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 (Tween<sup>fi</sup> 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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