Publications by authors named "Patchanee Charoenying"

6 Publications

  • Page 1 of 1

Enantioselective and Synergistic Herbicidal Activities of Common Amino Acids Against and .

Molecules 2021 Apr 4;26(7). Epub 2021 Apr 4.

Department of Chemistry, School of Science, King Mongkut's Institute of Technology Ladkrabang, Bangkok 10520, Thailand.

Amino acids have a wide range of biological activities, which usually rely on the stereoisomer presented. In this study, glycine and 21 common α-amino acids were investigated for their herbicidal property against Chinese amaranth ( L.) and barnyard grass ( (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, -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 enantioselective 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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http://dx.doi.org/10.3390/molecules26072071DOI Listing
http://www.ncbi.nlm.nih.gov/pmc/articles/PMC8038461PMC
April 2021

Herbicidal Activity of Flavokawains and Related -Chalcones against L. and (L.) Beauv.

ACS Omega 2019 Dec 27;4(24):20748-20755. Epub 2019 Nov 27.

Department of Chemistry, Faculty of Science, Integrated Applied Chemistry Research Unit, Faculty of Science, and Department of Plant Production Technology, Faculty of Agricultural Technology, King Mongkut's Institute of Technology Ladkrabang, Bangkok 10520, Thailand.

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-(,-dimethylamino)phenyl, -methylpyrrole, or thiophenyl groups inhibited the germination and growth of Chinese amaranth ( L.) with moderate to high degrees compared to commercial butachlor. For barnyardgrass ( (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. ()-2-(2-(3-Oxo-3-(thiophen-2-yl)prop-1-enyl)phenoxy)acetic acid () 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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http://dx.doi.org/10.1021/acsomega.9b03144DOI Listing
http://www.ncbi.nlm.nih.gov/pmc/articles/PMC6906942PMC
December 2019

Inhibitory Effects of a Variety of Aldehydes on Amaranthus tricolor L. and Echinochloa crus-galli (L.) Beauv.

Molecules 2018 Feb 21;23(2). Epub 2018 Feb 21.

Department of Chemistry, Faculty of Science, King Mongkut's Institute of Technology Ladkrabang, Bangkok 10520, Thailand.

Thirty-seven commercial aldehydes containing aliphatic chains and aromatic rings as well as heteroaromatic rings were evaluated for their inhibitory activities against Chinese amaranth ( L.) and barnyardgrass ( (L.) Beauv). Polysorbate 80 (Tween 80) was used as a surfactant and the research was preliminarily conducted at 400 μM of all aldehydes. Among these aldehydes, ()-cinnamaldehyde () 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, ()-crotonaldehyde (), 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 (), 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 () had a high inhibitory effect on Chinese amaranth which closely related to the effect of ()-crotonaldehyde () and ()-cinnamaldehyde (), whereas, other heteroaromatic aldehydes showed lower effects. In the case of a monocot plant, barnyardgrass, no tested aldehydes reduced seed germination, however, ()-cinnamaldehyde (), 2,4,6-trimethoxybenzaldehyde () and 4-(dimethylamino)benzaldehyde () 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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http://dx.doi.org/10.3390/molecules23020471DOI Listing
http://www.ncbi.nlm.nih.gov/pmc/articles/PMC6016959PMC
February 2018

Herbicidal Activities of Some Allelochemicals and Their Synergistic Behaviors toward Amaranthus tricolor L.

Molecules 2017 Oct 27;22(11). Epub 2017 Oct 27.

Department of Chemistry, Faculty of Science, King Mongkut's Institute of Technology Ladkrabang, Bangkok 10520, Thailand.

Seven allelochemicals, namely -(+)-limonene (), vanillin (), xanthoxyline (), vanillic acid (), linoleic acid (), methyl linoleate (), and (±)-odorine (), were investigated for their herbicidal activities on Chinese amaranth ( L.). At 400 μM, xanthoxyline () showed the greatest inhibitory activity on seed germination and seedling growth of the tested plant. Both vanillic acid () and (±)-odorine () inhibited shoot growth, however, apart from xanthoxyline (), only vanillic acid () could inhibit root growth. Interestingly, -(+)-limonene () lightly promoted root length. Other substances had no allelopathic effect on seed germination and seedling growth of the tested plant. To better understand and optimize the inhibitory effects of these natural herbicides, 21 samples of binary mixtures of these seven compounds were tested at 400 μM using 0.25% (/) Tween 80 as a control treatment. The results showed that binary mixtures of -(+)-limonene:xanthoxyline (:), vanillin:xanthoxyline (:), and xanthoxyline:linoleic acid (:) exhibited strong allelopathic activities on germination and seedling growth of the tested plant, and the level of inhibition was close to the effect of xanthoxyline () at 400 µM and was better than the effect of xanthoxyline () at 200 µM. The inhibition was hypothesized to be from a synergistic interaction of each pair of alleochemicals. Mole ratios of each pair of allelochemicals ((:), (:), and (:)) were then evaluated, and the best ratios of the binary mixtures :, : and : were found to be 2:8, 2:8, and 4:6 respectively. These binary mixtures significantly inhibited germination and shoot and root growth of Chinese amaranth at low concentrations. The results reported here highlight a synergistic behavior of some allelochemicals which could be applied in the development of potential herbicides.
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http://dx.doi.org/10.3390/molecules22111841DOI Listing
http://www.ncbi.nlm.nih.gov/pmc/articles/PMC6150416PMC
October 2017

Evaluation of allelopathic, decomposition and cytogenetic activities of Jasminum officinale L. f. var. grandiflorum (L.) Kob. on bioassay plants.

Bioresour Technol 2010 Jul 3;101(14):5677-84. Epub 2010 Mar 3.

Faculty of Agricultural Technology, King Mongkut's Institute of Technology Ladkrabang, Bangkok 10520, Thailand.

Methanolic extracts prepared from dried leaves of Jasminum officinale f. var. grandiflorum (L.) Kob. (Spanish jasmine) inhibited seed germination and stunted both root and shoot length of the weeds Echinochloa crus-galli (L.) Beauv. and Phaseolus lathyroides L. The main active compound was isolated and determined by spectral data as a secoiridoid glucoside named oleuropein. In addition, a decrease in allelopathic efficacy appeared as the decomposition periods increased. The mitotic index in treated onion root tips decreased with increasing concentrations of the extracts and longer periods of treatment. Likewise, the mitotic phase index was altered in onion incubated with crude extract. Furthermore, crude extract produced mitotic abnormalities resulting from its action on chromatin organization and mitotic spindle.
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http://dx.doi.org/10.1016/j.biortech.2010.02.038DOI Listing
July 2010

Indole synthesis by controlled carbolithiation of o-aminostyrenes.

J Org Chem 2004 Nov;69(23):7836-46

Centre for Synthesis and Chemical Biology, Conway Institute, Department of Chemistry, University College Dublin, Belfield, Dublin 4, Ireland.

An effective synthesis of the functionalized indole ring system has been developed from substituted o-aminostyrene starting material. Our methodology involves a novel cascade reaction sequence of alkyllithium addition to the styrene double bond and subsequent trapping of the intermediate organolithium with a suitable electrophile, followed by an in situ ring closure and dehydration to generate the indole ring. This new reaction sequence allows for the introduction of molecular diversity at all positions on the indole scaffold. The procedure was shown to be successful with a range of both C and N substituents on the o-aminostyrenes. The reaction sequence was tolerant to the reactivity range of alkyllithiums such as tert-, sec-, and n-butyllithium. The electrophiles used were DMF, which generated indole products with C-2 unsubstituted, and nitriles, which incorporated the nitrile substituent at C-2. The o-aminostyrene starting materials were generated by a Pd-catalyzed cross-coupling reaction of a vinyl boronic acid equivalent with the readily available substituted o-bromoanilines.
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http://dx.doi.org/10.1021/jo048723eDOI Listing
November 2004