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Journal articles on the topic '3-phenyllactic acid'

Author: Grafiati

Published: 7 June 2025

Last updated: 26 June 2025

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1

Wu, Zhe, Shengyang Xu, Ying Yun, Tingting Jia, and Zhu Yu. "Effect of 3-Phenyllactic Acid and 3-Phenyllactic Acid-Producing Lactic Acid Bacteria on the Characteristics of Alfalfa Silage." Agriculture 10, no. 1 (2019): 10. http://dx.doi.org/10.3390/agriculture10010010.

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In this study, an experiment was performed to evaluate the effect of lactic acid bacteria and 3-phenyllactic acid (PLA) on the fermentation quality and chemical composition of alfalfa silage. Several PLA-tolerant strains were screened from silages and identified. The selected strains (1 × 106 colony forming units/g fresh alfalfa) and PLA (1.0, 2.0, or 3.0 g/kg) were applied to alfalfa before ensiling. After 45 days of storage, the silages were unsealed and subjected to component analysis. Biochemical methods and 16S rDNA gene sequencing were used for the identification of the two strains as Lactobacillus plantarum. The characteristics of chemical and fermentation compounds indicated that PLA and the two strains efficiently improved the quality of the alfalfa silage. It can be concluded that the use of the strains and PLA can significantly improve the quality of silage.

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2

Wulandari, Sri, Fika Aryati, Adam M. Ramadhan, and Agung Rahmadani. "Sintesis Senyawa Phenyllactic Acid (2-Hydroxy-3-Phenylpropionic acid) dan Aktivitasnya sebagai Antibakteri." Jambura Journal of Chemistry 3, no. 2 (2021): 91–98. http://dx.doi.org/10.34312/jambchem.v3i2.11197.

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Phenyllactic acid merupakan asam organik yang banyak terdapat di madu dan dapat dihasikan dari fermentasi bakteri asam laktat pada makanan yang diproduksi oleh beberapa mikroorganisme. Phenyllactic acid memiliki aktivitas antimikroba spektrum luas terhadap bakteri dan jamur. Phenyllactic acid dapat disintesis berdasarkan reaksi diazotasi. Dalam penelitian ini, phenyllactic acid disintesis dari bahan dasar fenilalanin dan natrium nitrit dengan katalis asam sulfat pada suhu -5oC selama 2 jam. Hasil karakterisasi menggunakan MS, 1H-NMR dan 13C-NMR menunjukan telah terbentuknya senyawa phenyllactic acid dengan rendemen 40,6%. Dilakukan pengujian aktivitas antibakteri senyawa phenyllactic acid yang ditunjukkan dengan adanya zona hambat pada bakteri Escherichia coli dan Staphylococcus aureus pada konsentrasi 0,5% masing-masing sebesar 11.05 mm dan 12.02 mm.

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3

DIEULEVEUX, VIRGINIE, and MICHELINE GUÉGUEN. "Antimicrobial Effects of d-3-Phenyllactic Acid on Listeria monocytogenes in TSB-YE Medium, Milk, and Cheese." Journal of Food Protection 61, no. 10 (1998): 1281–85. http://dx.doi.org/10.4315/0362-028x-61.10.1281.

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d-3-Phenyllactic acid is a compound with anti-Listeria activity which is produced and secreted by the yeastlike fungus, Geotrichum candidum. This compound has a bactericidal effect independent of the physiological State of Listeria monocytogenes when added at a concentration of 7 mg/ml to tryptic soy broth supplemented with yeast extract (TSB-YE). An initial L. monocytogenes population of 105 CFU/ml was reduced 100-fold (2 log) after 4 days of culture at 25 °C in TSB-YE containing d-3-phenyllactic acid. The Listeria population was reduced 1,000-fold (3 log) when the compound was added during the exponential growth phase, and was reduced to less than 10 CFU/ml when it was added during the stationary phase. d-3-Phenyllactic acid had a bacteriostatic effect in UHT whole milk, reducing the population by 4.5 log, to give fewer cells than in the control after 5 days of culture. The results obtained with L. monocytogenes at concentrations of 105 and 103 CFU/ml in cheese curds were less conclusive. d-3-Phenyllactic acid was 10 times less active than nisin in our experimental conditions (TSB-YE at 25°C).

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4

Beloborodova, N. V., I. T. Bairamov, A. Yu Olenin, and N. I. Fedotcheva. "Exometabolites of some anaerobic microorganisms of human microflora." Biomeditsinskaya Khimiya 57, no. 1 (2011): 95–105. http://dx.doi.org/10.18097/pbmc20115701095.

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Some exometabolites produced by basic representatives of human anaerobic microflora were investigated, detected by gas chromatography - mass spectrometry (GC-MS). In vitro besides lactic acid Bifidobacterium and Lactobacillus generate substantial amounts of phenyllactic and p-hydroxyphenyllactic acids. Clostridium produced 2-hydroxybutyric acid and to a lesser extent lactic and phenyllactic acids. In contrast to С. perfringens, C. sporogenes generates substantial amount of phenylpropionic and p-hydroxyphenylpropionic acids and less p-hydroxyphenyllactic acid. С. perfringens produced minor amounts of 2-hydroxyglutaric acid. Bacteroids are potent producers of succinic and fumaric acids; they also contribute to production of significant portion of lactic acid. E. lentum generate lactic, phenyllactic and succinic acids and form a characteristic only for ones (from studied microorganisms) 2-hydroxyhexanic and 2-hydroxy-3-methylbutyric acids.

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5

Chen, Yu-Pei, Mingyu Li, Zirong Liu, Jinxiong Wu, Fangfang Chen, and Shudi Zhang. "Inhibition of Tyrosinase and Melanogenesis by Carboxylic Acids: Mechanistic Insights and Safety Evaluation." Molecules 30, no. 7 (2025): 1642. https://doi.org/10.3390/molecules30071642.

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It is well established that certain carboxylic acid compounds can effectively inhibit tyrosinase activity. This study investigated the mechanisms by which four carboxylic acid compounds—3-phenyllactic acid, lactic acid, L-pyroglutamic acid, and malic acid—inhibit tyrosinase and melanogenesis. IC50 values for mushroom tyrosinase inhibition ranged from 3.38 to 5.42 mM, with 3-phenyllactic acid (3.50 mM), lactic acid (5.42 mM), and malic acid (3.91 mM) exhibiting mixed-type inhibition, while L-pyroglutamic acid (3.38 mM) showed competitive inhibition, as determined by enzymatic kinetic analysis. Additionally, the acidification effects of lactic acid, L-pyroglutamic acid, and malic acid contributed to the reduction in tyrosinase activity. Furthermore, all four carboxylic acid compounds effectively inhibited DOPA auto-oxidation (IC50 = 0.38–0.66 mM), ranking in potency as follows: malic acid (0.38 mM) > lactic acid (0.57 mM) > 3-phenyllactic acid (0.63 mM) > L-pyroglutamic acid (0.66 mM). These compounds also demonstrated a dose-dependent reduction in melanin production in B16-F10 cells. Proteomic analysis further revealed that these compounds not only inhibit key proteins involved in melanin synthesis, such as tyrosinase, tyrosinase-related protein 1, and tyrosinase-related protein 2, but also potentially modulate other genes associated with melanogenesis and metabolism, including Pmel, Slc45a2, Ctns, Oca2, and Bace2. Network toxicology analysis indicated that these four compounds exhibit a low risk of inducing dermatitis. These findings suggest that these compounds may indirectly regulate melanin-related pathways through multiple mechanisms, highlighting their potential for further applications in cosmetics and pharmaceuticals.

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6

Chettu, Suresh Kumar, Rajesh Bagepalli Madhu, Gajendrasinh Balvantsinh Raolji, et al. "First total synthesis of cyclodepsipeptides clavatustide A and B and their enantiomers." RSC Advances 6, no. 66 (2016): 61555–65. http://dx.doi.org/10.1039/c6ra08861a.

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7

Broberg, Anders, Karin Jacobsson, Katrin Ström, and Johan Schnürer. "Metabolite Profiles of Lactic Acid Bacteria in Grass Silage." Applied and Environmental Microbiology 73, no. 17 (2007): 5547–52. http://dx.doi.org/10.1128/aem.02939-06.

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ABSTRACT The metabolite production of lactic acid bacteria (LAB) on silage was investigated. The aim was to compare the production of antifungal metabolites in silage with the production in liquid cultures previously studied in our laboratory. The following metabolites were found to be present at elevated concentrations in silos inoculated with LAB strains: 3-hydroxydecanoic acid, 2-hydroxy-4-methylpentanoic acid, benzoic acid, catechol, hydrocinnamic acid, salicylic acid, 3-phenyllactic acid, 4-hydroxybenzoic acid, (trans, trans)-3,4-dihydroxycyclohexane-1-carboxylic acid, p-hydrocoumaric acid, vanillic acid, azelaic acid, hydroferulic acid, p-coumaric acid, hydrocaffeic acid, ferulic acid, and caffeic acid. Among these metabolites, the antifungal compounds 3-phenyllactic acid and 3-hydroxydecanoic acid were previously isolated in our laboratory from liquid cultures of the same LAB strains by bioassay-guided fractionation. It was concluded that other metabolites, e.g., p-hydrocoumaric acid, hydroferulic acid, and p-coumaric acid, were released from the grass by the added LAB strains. The antifungal activities of the identified metabolites in 100 mM lactic acid were investigated. The MICs against Pichia anomala, Penicillium roqueforti, and Aspergillus fumigatus were determined, and 3-hydroxydecanoic acid showed the lowest MIC (0.1 mg ml−1 for two of the three test organisms).

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8

YU, Shuhuai, Houyi JIANG, Bo JIANG, and Wanmeng MU. "Characterization ofD-Lactate Dehydrogenase ProducingD-3-Phenyllactic Acid fromPediococcus pentosaceus." Bioscience, Biotechnology, and Biochemistry 76, no. 4 (2012): 853–55. http://dx.doi.org/10.1271/bbb.110955.

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9

Dieuleveux, V., S. Lemarinier, and M. Guéguen. "Antimicrobial spectrum and target site of d-3-phenyllactic acid." International Journal of Food Microbiology 40, no. 3 (1998): 177–83. http://dx.doi.org/10.1016/s0168-1605(98)00031-2.

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10

Dieuleveux, V., D. Van Der Pyl, J. Chataud, and M. Gueguen. "Purification and Characterization of Anti-Listeria Compounds Produced by Geotrichum candidum." Applied and Environmental Microbiology 64, no. 2 (1998): 800–803. http://dx.doi.org/10.1128/aem.64.2.800-803.1998.

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ABSTRACT Geotrichum candidum can produce and excrete compounds that inhibit Listeria monocytogenes. These were purified by ultrafiltration, centrifugal partition chromatography, thin-layer chromatography, gel filtration, and high-pressure liquid chromatography, and analyzed by liquid chromatography-mass spectrometry, infrared spectrometry, nuclear magnetic resonance spectrometry, and optical rotation. Two inhibitors were identified:d-3-phenyllactic acid and d-3-indollactic acid.

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11

Lavermicocca, Paola, Francesca Valerio, Antonio Evidente, Silvia Lazzaroni, Aldo Corsetti, and Marco Gobbetti. "Purification and Characterization of Novel Antifungal Compounds from the Sourdough Lactobacillus plantarum Strain 21B." Applied and Environmental Microbiology 66, no. 9 (2000): 4084–90. http://dx.doi.org/10.1128/aem.66.9.4084-4090.2000.

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ABSTRACT Sourdough lactic acid bacteria were selected for antifungal activity by a conidial germination assay. The 10-fold-concentrated culture filtrate of Lactobacillus plantarum 21B grown in wheat flour hydrolysate almost completely inhibited Eurotium repens IBT18000, Eurotium rubrum FTDC3228,Penicillium corylophilum IBT6978, Penicillium roqueforti IBT18687, Penicillium expansum IDM/FS2,Endomyces fibuliger IBT605 and IDM3812, Aspergillus niger FTDC3227 and IDM1, Aspergillus flavus FTDC3226,Monilia sitophila IDM/FS5, and Fusarium graminearum IDM623. The nonconcentrated culture filtrate ofL. plantarum 21B grown in whole wheat flour hydrolysate had similar inhibitory activity. The activity was fungicidal. Calcium propionate at 3 mg ml−1 was not effective under the same assay conditions, while sodium benzoate caused inhibition similar toL. plantarum 21B. After extraction with ethyl acetate, preparative silica gel thin-layer chromatography, and chromatographic and spectroscopic analyses, novel antifungal compounds such as phenyllactic and 4-hydroxy-phenyllactic acids were identified in the culture filtrate of L. plantarum 21B. Phenyllactic acid was contained at the highest concentration in the bacterial culture filtrate and had the highest activity. It inhibited all the fungi tested at a concentration of 50 mg ml−1 except forP. roqueforti IBT18687 and P. corylophilumIBT6978 (inhibitory concentration, 166 mg ml−1). L. plantarum 20B, which showed high antimold activity, was also selected. Preliminary studies showed that phenyllactic and 4-hydroxy-phenyllactic acids were also contained in the bacterial culture filtrate of strain 20B. Growth of A. niger FTDC3227 occurred after 2 days in breads started with Saccharomyces cerevisiae 141 alone or with S. cerevisiae andLactobacillus brevis 1D, an unselected but acidifying lactic acid bacterium, while the onset of fungal growth was delayed for 7 days in bread started with S. cerevisiae and selectedL. plantarum 21B.

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12

Yoo, Jeoung Ah, Young Muk Lim, and Min Ho Yoon. "Production and antifungal effect of 3-phenyllactic acid (PLA) by lactic acid bacteria." Journal of Applied Biological Chemistry 59, no. 3 (2016): 173–78. http://dx.doi.org/10.3839/jabc.2016.032.

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13

Mu, Wanmeng, Shuhuai Yu, Lanjun Zhu, Tao Zhang, and Bo Jiang. "Recent research on 3-phenyllactic acid, a broad-spectrum antimicrobial compound." Applied Microbiology and Biotechnology 95, no. 5 (2012): 1155–63. http://dx.doi.org/10.1007/s00253-012-4269-8.

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14

Modec, Barbara, and Darko Dolenc. "Oxidative cleavage of 3-phenyllactic acid in presence of molybdenum complexes." Inorganic Chemistry Communications 23 (September 2012): 50–53. http://dx.doi.org/10.1016/j.inoche.2012.06.003.

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15

Tong, Shengqiang, Xiaoping Wang, Mangmang Shen, et al. "Enantioseparation of 3-phenyllactic acid by chiral ligand exchange countercurrent chromatography." Journal of Separation Science 40, no. 8 (2017): 1834–42. http://dx.doi.org/10.1002/jssc.201601384.

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16

TEKEWE, A. "Development and validation of HPLC method for the resolution of drug intermediates: dl-3-Phenyllactic acid, dl-O-acetyl-3-phenyllactic acid and (±)-mexiletine acetamide enantiomers." Talanta 75, no. 1 (2008): 239–45. http://dx.doi.org/10.1016/j.talanta.2007.11.004.

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17

Yu, Shuhuai, Chen Zhou, Tao Zhang, Bo Jiang, and Wanmeng Mu. "3-Phenyllactic acid production in milk by SK25 during laboratory fermentation process." Journal of Dairy Science 98, no. 2 (2015): 813–17. http://dx.doi.org/10.3168/jds.2014-8645.

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18

Fan, Wenguang, Baoyu Li, Nana Du, et al. "Energy metabolism as the target of 3-phenyllactic acid against Rhizopus oryzae." International Journal of Food Microbiology 369 (May 2022): 109606. http://dx.doi.org/10.1016/j.ijfoodmicro.2022.109606.

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19

Cortés-Zavaleta, O., A. López-Malo, A. Hernández-Mendoza, and H. S. García. "Antifungal activity of lactobacilli and its relationship with 3-phenyllactic acid production." International Journal of Food Microbiology 173 (March 2014): 30–35. http://dx.doi.org/10.1016/j.ijfoodmicro.2013.12.016.

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20

Ayer, William A., Lois M. Browne, Meow-Chen Feng, Helena Orszanska, and Hussein Saeedi-Ghomi. "The chemistry of the blue stain fungi. Part 1. Some metabolites of Ceratocystis species associated with mountain pine beetle infected lodgepole pine." Canadian Journal of Chemistry 64, no. 5 (1986): 904–9. http://dx.doi.org/10.1139/v86-149.

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Metabolites formed in still culture by Ceratocystisclavigera, C. ips, and C. huntii, three of the four Ceratocystis species associated with the blue stain disease of pine, have been identified. In addition to the ubiquitous fungal metabolites ergosterol, ergosterol peroxide, and fatty acids we have isolated succinic acid, β-phenethyl alcohol (1), tryptophol (2), prolylleucyl anhydride (3), tyrosol (4), 3-phenylpropane-1,2-diol (5), 6,8-dihydroxy-3-methylisocoumarin (8), 6,8-dihydroxy-3-hydroxymethylisocoumarin (9), p-hydroxybenzaldehyde (10), phenylacetic acid (11), p-hydroxyphenylacetic acid (12), phenyllactic acid (13), p-hydroxyphenyllactic acid (14), and 2,3-dihydroxybenzoic acid (15). The complex formed by chelation of iron with 2,3-dihydroxybenzoic acid may be responsible, at least in part, for the blue staining of the sapwood of diseased pine.

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21

Mu, Wanmeng, Shuhuai Yu, Lanjun Zhu, Bo Jiang, and Tao Zhang. "Production of 3-phenyllactic acid and 4-hydroxyphenyllactic acid by Pediococcus acidilactici DSM 20284 fermentation." European Food Research and Technology 235, no. 3 (2012): 581–85. http://dx.doi.org/10.1007/s00217-012-1768-x.

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22

Kottgen, Peter, Anthony Linden, and Heinz Heimgartner. "Synthesis of a Regular 24-membered Cyclodepsipeptide by Direct Amide Cyclization." Zeitschrift für Naturforschung B 64, no. 6 (2009): 689–98. http://dx.doi.org/10.1515/znb-2009-0615.

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The synthesis of a 24-membered cyclic depsipeptide with an alternating sequence of phenyllactic acid and α-aminoisobutyric acid (Aib) is described. The linear precursor was prepared via the ‘azirine/oxazolone method’ using 2,2-dimethyl-3-amino-2H-azirines as building blocks for the α,α-disubstituted α-amino acid Aib. The macrolactonization leading to the cyclodepsipeptide was achieved by the ‘direct amide cyclization’, i. e., by treatment of a solution of the linear precursor in toluene with HCl gas.

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23

SCHWENNINGER, SUSANNE MIESCHER, CHRISTOPHE LACROIX, STEFAN TRUTTMANN, et al. "Characterization of Low-Molecular-Weight Antiyeast Metabolites Produced by a Food-Protective Lactobacillus-Propionibacterium Coculture." Journal of Food Protection 71, no. 12 (2008): 2481–87. http://dx.doi.org/10.4315/0362-028x-71.12.2481.

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We developed a pH-controlled batch fermentation process with separately immobilized cells of the protective coculture of Lactobacillus paracasei subsp. paracasei SM20 and Propionibacterium jensenii SM11 in supplemented whey permeate medium yielding cell-free supernatants with high antiyeast activity against Candida pulcherrima and Rhodotorula mucilaginosa. The antiyeast compounds were resistant to proteinase K and pronase E treatments and showed high heat resistance (121°C for 15 min). Diafiltration (1,000-Da cutoff) revealed that the inhibitory metabolites have low molecular weights. Partial purification of active compounds was achieved by a microplate bioassay controlled procedure with solid-phase extraction (C18) followed by (i) gel filtration chromatography or (ii) semipreparative reverse-phase high-performance liquid chromatography (C18). In addition to propionic, acetic, and lactic acids, 2-pyrrolidone-5-carboxylic acid, 3-phenyllactic acid, hydroxyphenyllactic acid, and succinic acid were identified by chromatography and mass spectrometry. Accurate quantifications revealed only low concentrations (up to 7 mM) of 2-pyrrolidone-5-carboxylic acid, 3-phenyllactic acid, and hydroxyphenyllactic acid produced during fermentation in contrast to relatively high MICs (50 to more than 500 mM) determined at different pH values (4.0, 5.0, and 6.0). Succinic acid was present at higher concentrations (29 mM) in cell-free supernatants but with comparable high MICs (200 to more than 500 mM and pH 4.0, 5.0, and 6.0). Although none of these compounds was the main substance responsible per se for suppression of yeast growth, our study revealed a complex antiyeast mechanism with putative synergistic effects between several low-molecular-weight compounds.

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24

Sakurai, Takuma, Ayako Horigome, Toshitaka Odamaki, Takashi Shimizu, and Jin-Zhong Xiao. "Production of Hydroxycarboxylic Acid Receptor 3 (HCA3) Ligands by Bifidobacterium." Microorganisms 9, no. 11 (2021): 2397. http://dx.doi.org/10.3390/microorganisms9112397.

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Hydroxycarboxylic acid receptor 3 (HCA3) was recently identified in the genomes of humans and other hominids but not in other mammals. We examined the production of HCA3 ligands by Bifidobacterium spp. In addition to 4-hydroxyphenyllactic acid, phenyllactic acid (PLA), and indole-3-lactic acid (ILA), we found that LeuA was produced by Bifidobacterium as an HCA3 ligand. The four ligands produced were the mixtures of enantiomers, and D-ILA, D-PLA, and D-LeuA showed stronger activity of the HCA3 ligand than their respective L-isomers. However, there was no difference in AhR activity between the two ILA enantiomers. These results provide new insights into the HCA3 ligands produced by Bifidobacterium and suggest the importance of investigating the absolute stereo structures of these metabolites.

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25

Xu, Juan-Juan, Jin-Zhi Sun, Kuo-Lin Si, and Chun-Feng Guo. "3-Phenyllactic acid production by Lactobacillus crustorum strains isolated from naturally fermented vegetables." LWT 149 (September 2021): 111780. http://dx.doi.org/10.1016/j.lwt.2021.111780.

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26

Tao, Hu, Da-Fu Cui, and You-Shang Zhang. "Synthesis and Characteristics of an Aspartame Analogue, L-Asparaginyl L-3-Phenyllactic Acid Methyl Ester." Acta Biochimica et Biophysica Sinica 36, no. 6 (2004): 385–89. http://dx.doi.org/10.1093/abbs/36.6.385.

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Abstract An aspartame analogue, L-asparaginyl L-3-phenyllactic acid methyl ester was synthesized with aspartic acid replaced by asparagine and peptide bond replaced by ester bond. The aspartic acid of aspartame could be replaced by asparagine as reported in the literature. In this analogue, the hydrogen of amide group could still form a hydrogen bond with the oxygen of ester bond and the ester bond was isosteric with peptide bond. However, the product was not sweet, showing that the peptide bond could not be replaced by ester bond. The peptide C-N bond behaves as a double bond that is not free to rotate and the C, O, N and H atoms are in the same plane. The replacement of peptide bond by ester bond destroyed the unique conformation of peptide bond, resulting in the loss of sweet taste.

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27

Banoth, Linga, Manpreet Singh, Alemu Tekewe, and Uttam Banerjee. "Increased enantioselectivity of lipase in the transesterification ofdl-(±)-3-phenyllactic acid in ionic liquids." Biocatalysis and Biotransformation 27, no. 4 (2009): 263–70. http://dx.doi.org/10.1080/10242420903049903.

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28

Ström, Katrin, Jörgen Sjögren, Anders Broberg, and Johan Schnürer. "Lactobacillus plantarum MiLAB 393 Produces the Antifungal Cyclic Dipeptides Cyclo(l-Phe-l-Pro) and Cyclo(l-Phe-trans-4-OH-l-Pro) and 3-Phenyllactic Acid." Applied and Environmental Microbiology 68, no. 9 (2002): 4322–27. http://dx.doi.org/10.1128/aem.68.9.4322-4327.2002.

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ABSTRACT We have isolated a Lactobacillus plantarum strain (MiLAB 393) from grass silage that produces broad-spectrum antifungal compounds, active against food- and feed-borne filamentous fungi and yeasts in a dual-culture agar plate assay. Fusarium sporotrichioides and Aspergillus fumigatus were the most sensitive among the molds, and Kluyveromyces marxianus was the most sensitive yeast species. No inhibitory activity could be detected against the mold Penicillium roqueforti or the yeast Zygosaccharomyces bailii. An isolation procedure, employing a microtiter well spore germination bioassay, was devised to isolate active compounds from culture filtrate. Cell-free supernatant was fractionated on a C18 SPE column, and the 95% aqueous acetonitrile fraction was further separated on a preparative HPLC C18 column. Fractions active in the bioassay were then fractionated on a porous graphitic carbon column. The structures of the antifungal compounds cyclo(l-Phe-l-Pro), cyclo(l-Phe-trans-4-OH-l-Pro) and 3-phenyllactic acid (l/d isomer ratio, 9:1), were determined by nuclear magnetic resonance spectroscopy, mass spectrometry, and gas chromatography. MIC values against A. fumigatus and P. roqueforti were 20 mg ml−1 for cyclo(l-Phe-l-Pro) and 7.5 mg ml−1 for phenyllactic acid. Combinations of the antifungal compounds revealed weak synergistic effects. The production of the antifungal cyclic dipeptides cyclo(l-Phe-l-Pro) and cyclo(l-Phe-trans-4-OH-l-Pro) by lactic acid bacteria is reported here for the first time.

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29

OHHIRA, IICHIRO, SHINSUKE KUWAKI, HIDETOSHI MORITA, et al. "Identification of 3-Phenyllactic Acid As a Possible Antibacterial Substance Produced by Enterococcus faecalis TH10." Biocontrol Science 9, no. 3 (2004): 77–81. http://dx.doi.org/10.4265/bio.9.77.

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30

Li, Minghua, Xiumei Meng, Zhiyang Sun, Chunjie Zhu, and Huiying Ji. "Effects of NADH Availability on 3-Phenyllactic Acid Production by Lactobacillus plantarum Expressing Formate Dehydrogenase." Current Microbiology 76, no. 6 (2019): 706–12. http://dx.doi.org/10.1007/s00284-019-01681-0.

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31

Yadav, Ganapati D., and Sandip V. Pawar. "Insight into microwave irradiation and enzyme catalysis in enantioselective resolution of dl-(±)-3-phenyllactic acid." Applied Microbiology and Biotechnology 96, no. 1 (2012): 69–79. http://dx.doi.org/10.1007/s00253-012-4183-0.

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32

Prema, P., D. Smila, A. Palavesam, and G. Immanuel. "Production and Characterization of an Antifungal Compound (3-Phenyllactic Acid) Produced by Lactobacillus plantarum Strain." Food and Bioprocess Technology 3, no. 3 (2008): 379–86. http://dx.doi.org/10.1007/s11947-008-0127-1.

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33

Rodríguez, Noelia, José Manuel Salgado, Sandra Cortés, and José Manuel Domínguez. "Antimicrobial activity of d-3-phenyllactic acid produced by fed-batch process against Salmonella enterica." Food Control 25, no. 1 (2012): 274–84. http://dx.doi.org/10.1016/j.foodcont.2011.10.042.

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34

WUENSCH, B., and M. ZOTT. "ChemInform Abstract: Chiral 2-Benzopyran-3-carboxylates by Oxa-Pictet-Spengler Reaction of ( S)-3-Phenyllactic Acid Derivatives." ChemInform 23, no. 16 (2010): no. http://dx.doi.org/10.1002/chin.199216215.

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35

Rodríguez-Pazo, Noelia, Sabrina da Silva Sabo, José Manuel Salgado-Seara, Saleh Al Arni, Ricardo Pinheiro de Souza Oliveira, and José Manuel Domínguez. "Optimisation of cheese whey enzymatic hydrolysis and further continuous production of antimicrobial extracts by Lactobacillus plantarum CECT-221." Journal of Dairy Research 83, no. 3 (2016): 402–11. http://dx.doi.org/10.1017/s0022029916000352.

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The enzymatic hydrolysis of cheese whey was optimised using the enzymes iZyme, Alcalase or Flavourzyme under different conditions. Hydrolysates supplemented with commercial nutrients were evaluated as fermentation broths to produce DL-3-Phenyllactic acid (PLA) from phenylalanine (Phe) by Lactobacillus plantarum CECT-221. Optimised hydrolysates were obtained using Flavourzyme at 50 °C and 100 rpm during 12 h, and assayed in 250 ml Erlenemyer flasks using different proportions of vinasses as economic nutrient. The process was then scaled up using a 2 litres Bioreactor working under the continuous modality. Under the intermediate dilution rate of 0·0207 h−1 0·81 ± 0·026 mM of PLA and 38·8 ± 3·253 g/l of lactic acid were produced. A final evaluation revealed that lactic acid, and bacteriocins exerted the highest inhibitory effect among the extracted components of cell-free supernatants.

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Lee, Moeun, Jung Hee Song, Eun Ji Choi, Ye-Rang Yun, Ki Won Lee, and Ji Yoon Chang. "UPLC-QTOF-MS/MS and GC-MS Characterization of Phytochemicals in Vegetable Juice Fermented Using Lactic Acid Bacteria from Kimchi and Their Antioxidant Potential." Antioxidants 10, no. 11 (2021): 1761. http://dx.doi.org/10.3390/antiox10111761.

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This study aims to investigate fermentative metabolites in probiotic vegetable juice from four crop varieties (Brassica oleracea var. capitata, B. oleracea var. italica, Daucus carota L., and Beta vulgaris) and their antioxidant properties. Vegetable juice was inoculated with two lactic acid bacteria (LAB) (Companilactobacillus allii WiKim39 and Lactococcus lactis WiKim0124) isolated from kimchi and their properties were evaluated using untargeted UPLC-QTOF-MS/MS and GC-MS. The samples were also evaluated for radical (DPPH• and OH•) scavenging activities, lipid peroxidation, and ferric-reducing antioxidant power. The fermented vegetable juices exhibited high antioxidant activities and increased amounts of total phenolic compounds. Fifteen compounds and thirty-two volatiles were identified using UPLC-QTOF-MS/MS and GC-MS, respectively. LAB fermentation significantly increased the contents of d-leucic acid, indole-3-lactic acid, 3-phenyllactic acid, pyroglutamic acid, γ-aminobutyric acid, and gluconic acid. These six metabolites showed a positive correlation with antioxidant properties. Thus, vegetable juices fermented with WiKim39 and WiKim0124 can be considered as novel bioactive health-promoting sources.

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Debonne, Els, An Vermeulen, Naomi Bouboutiefski, et al. "Modelling and validation of the antifungal activity of DL-3-phenyllactic acid and acetic acid on bread spoilage moulds." Food Microbiology 88 (June 2020): 103407. http://dx.doi.org/10.1016/j.fm.2019.103407.

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Thierig, Marcus, Jana Raupbach, Diana Wolf, Thorsten Mascher, Kannan Subramanian, and Thomas Henle. "3-Phenyllactic Acid and Polyphenols Are Substances Enhancing the Antibacterial Effect of Methylglyoxal in Manuka Honey." Foods 12, no. 5 (2023): 1098. http://dx.doi.org/10.3390/foods12051098.

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Manuka honey is known for its unique antibacterial activity, which is due to methylglyoxal (MGO). After establishing a suitable assay for measuring the bacteriostatic effect in a liquid culture with a time dependent and continuous measurement of the optical density, we were able to show that honey differs in its growth retardingeffect on Bacillus subtilis despite the same content of MGO, indicating the presence of potentially synergistic compounds. In model studies using artificial honey with varying amounts of MGO and 3-phenyllactic acid (3-PLA), it was shown that 3-PLA in concentrations above 500 mg/kg enhances the bacteriostatic effect of the model honeys containing 250 mg/kg MGO or more. It has been shown that the effect correlates with the contents of 3-PLA and polyphenols in commercial manuka honey samples. Additionally, yet unknown substances further enhance the antibacterial effect of MGO in manuka honey. The results contribute to the understanding of the antibacterial effect of MGO in honey.

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Daher, Sawsan, and Fazil O. Gülaçar. "Identification of New Aromatic Compounds in the New Zealand Manuka Honey by Gas Chromatography-Mass Spectrometry." E-Journal of Chemistry 7, s1 (2010): S7—S14. http://dx.doi.org/10.1155/2010/472769.

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Analysis of aromatic compounds in the New Zealand manuka honey was carried out by solid phase microextraction followed by gas chromatography-mass spectrometry. A total of 38 compounds were detected. Seven of them such as; 1,4-bis(x-methoxyphenyl)-but-2-en-1-one, 1,5-bis(x-methoxyphenyl)-pent-3-en-1-one, 1,4-bis(x-methoxyphenyl)-1-pentanone, 1,6-bis(x-methoxyphenyl)-3-heptene, 1,6-bis(x-methoxyphenyl)-hex-2(3 or 4)-en-1-one and 2(3, 4 or 5)-hydroxy-1,6-bis(x-methoxyphenyl)-1-hexanone, had never before been identified as natural products. Their structures were deduced from the mass spectral data. Seven other compounds; 2,3-dimethoxynaphthalene, 4-(x-methoxyphenyl)-1-phenyl-1-butanone, desoxyanisoin, 2,6-dimethoxybenzoic acid benzyl ester, 4,4'-dimethoxystilbene, 3,3,4,5,5,8-hexamethyl-2,3,5,6-tetrahydro-s-indacene-1,7-dione and 1,5-bis(4-methoxyphenyl)-pentane-1,5-dione, were found in honey for the first time. Methyl syringate,ortho-methoxyacetophenone and 3-phenyllactic acid were the most abundant components.

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Maki, Yuko, Hiroshi Soejima, Toru Kitamura, et al. "3-Phenyllactic acid, a root-promoting substance isolated from Bokashi fertilizer, exhibits synergistic effects with tryptophan." Plant Biotechnology 38, no. 1 (2021): 9–16. http://dx.doi.org/10.5511/plantbiotechnology.20.0727a.

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41

Hashimoto, Yoshihiro, Etsuko Kobayashi, Takakazu Endo, Makoto Nishiyama, and Sueharu Horinouchi. "Conversion of a Cyanhydrin Compound intoS-(−)-3-Phenyllactic Acid by Enantioselective Hydrolytic Activity ofPseudomonassp. BC-18." Bioscience, Biotechnology, and Biochemistry 60, no. 8 (1996): 1279–83. http://dx.doi.org/10.1271/bbb.60.1279.

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Yang, Yanqing, Ao Li, Mingmei Guo, et al. "Improving the storage quality and aroma quality of sweet cherry by postharvest 3-phenyllactic acid treatment." Scientia Horticulturae 338 (December 2024): 113661. http://dx.doi.org/10.1016/j.scienta.2024.113661.

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43

Navare, Pranoti S., and John C. MacDonald. "Investigation of Stability and Structure in Three Homochiral and Heterochiral Crystalline Forms of 3-Phenyllactic Acid." Crystal Growth & Design 11, no. 6 (2011): 2422–28. http://dx.doi.org/10.1021/cg200171r.

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Yang, Xiaoyuan, Jianpeng Li, Guocui Shi, Mingyong Zeng, and Zunying Liu. "Improving 3-phenyllactic acid production of Lactobacillus plantarum AB-1 by enhancing its quorum-sensing capacity." Journal of Food Science and Technology 56, no. 5 (2019): 2605–10. http://dx.doi.org/10.1007/s13197-019-03746-1.

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Jerković, Igor, Marin Roje, Carlo I. G. Tuberoso, Zvonimir Marijanović, Ana Kasum, and Marina Obradović. "Bioorganic Research of Galactites tomentosa Moench. Honey Extracts: Enantiomeric Purity of Chiral Marker 3-Phenyllactic Acid." Chirality 26, no. 8 (2014): 405–10. http://dx.doi.org/10.1002/chir.22340.

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46

Shi, Feng, Yin Qin, Shuyi Qiu, and You Luo. "Nutrients, Phytochemicals, and Antioxidant Capacity of Red Raspberry Nectar Fermented with Lacticaseibacillus paracasei." Foods 13, no. 22 (2024): 3666. http://dx.doi.org/10.3390/foods13223666.

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Fresh raspberries are highly perishable, but lactic acid bacteria fermentation offers a favourable method for developing healthy products. This study investigated the effects of Lacticaseibacillus paracasei fermentation on the nutrients and phytochemicals of red raspberry nectar using widely targeted metabolomics, as well as its antioxidant activity. The fermentation notably disrupted the raspberry tissue structure, reshaped its non-volatile composition, and increased its DPPH and hydroxyl free radical scavenging abilities. A total of 261 compounds showed significant differences, with 198 upregulated and 63 downregulated. Among these, certain flavonoid glucosides (e.g., pelargonid-in-3-O-rutinoside, delphinidin-3-O-rutinoside-7-O-glucoside, and kaempferol-3-O-glucoside) were significantly downregulated, while some bioactive phenolic acids (e.g., 3-(4-Hydroxyphenyl)-propionic acid and DL-3-phenyllactic acid), alkaloids (e.g., deoxymutaaspergillic acid and indole-3-lactic acid), amino acids (e.g., L-phenylalanine and L-glutamine), and B vitamins (e.g., VB6, VB7, and VB3) were substantially upregulated. Furthermore, the Kyoto Encyclopedia of Genes and Genomes (KEGG) annotation and enrichment analysis revealed that metabolic pathways and the biosynthesis of secondary metabolites contributed significantly to the new profile of fermented red raspberry nectar. These findings provide valuable insights for developing fermented raspberry products using Lacticaseibacillus paracasei, which can help minimise fresh raspberry loss and enhance their valorisation.

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Jin, Yuan, Zuoyong Zhang, Hanju Sun, et al. "Effects of Cyanidin-3-Glucoside Derived from Black Rice (Oryza Sativa L.) and Enzymatically Acylated Cyanidin-3-Glucoside Lauryl Ester on Intestinal Microorganisms In Vitro." Current Topics in Nutraceutical Research 20, no. 1 (2021): 159–68. http://dx.doi.org/10.37290/ctnr2641-452x.20:159-168.

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In this paper, cyanidin-3-glucoside was isolated and purified from black rice, then enzymatic acylation with lauric acid to obtain cyanidin-3-glucoside lauryl ester. The structure of cyanidin-3-glucoside lauryl ester was characterized by liquid chromatography electrospray ionization tandem mass spectrometry and Fourier transform infrared spectroscopy. Then the potential proliferative effect on probiotics and inhibitory effect on harmful bacteria of cyanidin-3-glucoside and cyanidin-3-glucoside lauryl ester were studied in vitro. The effects of cyanidin-3-glucoside and cyanidin-3-glucoside lauryl ester on the composition of human fecal intestinal flora and its metabolic pathway were also analyzed through 16S ribosomal ribonucleic acid high-throughput sequencing and gas chromatography-mass spectroscopy, respectively. The results indicated that cyanidin-3-glucoside lauryl ester was better than cyanidin-3-glucoside in promoting the growth of B. adolescentis, B. infantis, L. thermophiles, and L. acidophilus as well as inhibiting the growth of S. dysenteriae, Y. enterocolitica, S. enteritidis, and S. typhi. Additionally, the proliferative effect of cyanidin-3-glucoside lauryl ester was significantly improved in a lower media pH due to the intestinal microbial metabolism to produce more organic acids, such as propionic acid, phenyllactic acid, and lauric acid. The study will provide a theoretical basis for the application of cyanidin-3-glucoside lauryl ester in the intestinal health.

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Zhang, Jianming, Juan Chen, Chengcheng Zhang, Huaxi Yi, Daiyao Liu, and Daqun Liu. "Characterization and antibacterial properties of chitosan–polyvinyl alcohol-3-phenyllactic acid as a biodegradable active food packaging." Food Packaging and Shelf Life 34 (December 2022): 100963. http://dx.doi.org/10.1016/j.fpsl.2022.100963.

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Xu, J. ‐J, L. ‐J Fu, K. ‐L Si, T. ‐L Yue, and C. ‐F Guo. "3‐phenyllactic acid production by free‐whole‐cells of Lactobacillus crustorum in batch and continuous fermentation systems." Journal of Applied Microbiology 129, no. 2 (2020): 335–44. http://dx.doi.org/10.1111/jam.14599.

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Ansarin, Morteza, and Jack G. Woolley. "The biosynthesis of tropic acid. Part 6. Enantioselective, intact incorporation of (R)-(+)-3-phenyllactic acid into the tropic acid ester alkaloids of Datura." Journal of the Chemical Society, Perkin Transactions 1, no. 4 (1995): 487. http://dx.doi.org/10.1039/p19950000487.

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