Academic literature on the topic '3-phenyllactic acid'

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.

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.

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).

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.

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.

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).

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.

Os produtos naturais desempenham fundamental importância na descoberta de novos fármacos. Muitos destes fármacos originaram-se de produtos naturais microbianos o que demonstra uma extrema eficiência na habilidade dos micro-organismos de sintetizar substâncias químicas com elevado potencial biológico. Sabe-se que os insetos sociais estão sujeitos a condições climáticas e populacionais que aumentam sua susceptibilidade a parasitas. Assim, estes insetos desenvolveram um mecanismo de defesa evolutivo que consiste na associação simbiótica a bactérias capazes de biossintetizar produtos antimicrobianos contra os patógenos. Dispondo dessas informações, o presente trabalho contribuiu com o estudo dos produtos naturais biossintetizados pela bactéria Paenibacillus polymyxa ALLI-03-01, provável simbionte da espécie de abelha sem ferrão Melipona scutellaris. Os micro-organismos foram isolados de colônias mantidas no Departamento de Biologia da FFCLRP-USP. Todas as linhagens foram testadas contra dois fungos entomopatogênicos - Beauveria bassiana e Metarhizium anisopliae; os que apresentaram atividade antifúngica tiveram seus extratos em acetato de etila e metanol preparados e foram avaliados em ensaios antiparasitários contra Trypanosoma cruzi e Leishmania donovani. A bactéria ALLI-03-01, isolada do alimento larval, foi escolhida para os estudos químicos, pois apresentou satisfatória atividade antifúngica e proeminente atividade antiparasitária. Este micro-organismo foi identificado pelo sequenciamento do gene 16S rRNA como sendo a bactéria Paenibacillus polymyxa, conhecida pela alta capacidade de produção de metabólitos secundários. Para conhecer seu metabolismo, esta bactéria foi cultivada em meio ISP-2 ágar e líquido e do extrato em acetato de etila do cultivo fermentativo de P. polymyxa ALLI-03-01 foi isolado o ácido L-3-fenil lático. As atividades antifúngicas dos padrões comerciais dos ácidos D-(+)- e L-(-)- 3-fenil lático foram testadas frente ao fungo entomopatogênico B. bassiana e apenas o enantiômero L apresentou atividade antifúngica. Do extrato em metanol do cultivo em meio sólido do mesmo micro-organismo foram identificados em mistura, principalmente por MALDI-TOF MS/MS, nove diferentes ciclolipodepsipeptídeos, da classe das Fusaricidinas. As fusaricidinas são conhecidas por apresentarem alta atividade anti-microbiana, que foi comprovada quando duas frações compostas por diferentes fusaricidinas foram testadas frente ao fungo entomopatogênico Metarhizium anisopliae e contra a bactéria patogênica Paenibacillus larvae. As frações apresentaram resultados satisfatórios de inibição contra ambos os patógenos, dessa maneira as fusaricidinas e a produção seletiva do ácido L-3-fenil lático por esta bactéria podem ser vias de proteção da colônia, evitando que patógenos destruam-na e permitindo o desenvolvimento sadio de larvas. Sendo assim, este trabalho relata pela primeira vez a possível relação simbiótica existente entre o micro-organismo Paenibacillus polymyxa ALLI-03-01 e a colônia de abelhas Melipona scutellaris, bem como a produção por este micro-organismo de compostos com alta atividade antimicrobiana que podem exercer o controle de parasitas dentro da colônia, estabelecendo assim, uma possível relação ecológica entre o micro-organismo destacado e as abelhas Melipona scutellaris.<br>Natural products play an important role in drug discovery. Several drugs have been discovered or developed from microbial natural products hits and leads showing a great efficiency of microorganisms to synthesize compounds with high biological potential. It is known that social insects are subjected to climate and population conditions that increase their susceptibility to parasites. Therefore, these insects have developed an evolutionary defense mechanism consisting in symbiotic association with bacteria capable of biosynthesize antimicrobial products against pathogens. In this context, this study contributed to the knowledge of natural products biosynthesized by the bacterium Paenibacillus polymyxa ALLI-03-01, a probable symbiont of the stingless bee Melipona scutellaris. Microorganisms were isolated from colonies maintained at the Department of Biology of FFCLRP-USP. All strains were tested against two entomopathogenic fungi - Beauveria bassiana and Metarhizium anisopliae; strains that showed antifungal activity had their ethyl acetate and methanol extracts prepared and evaluated against the parasites Trypanosoma cruzi and Leishmania donovani. The bacterium ALLI-03-01, isolated from larval food, was selected for chemical studies, due to its satisfactory antifungal activity and outstanding antiparasitic activity. This microorganism was identified by gene 16S rRNA sequencing as Paenibacillus polymyxa, a bacterium recognized for its ability of biosynthesize secondary metabolities. This bacterium was cultivated in ISP-2 agar and liquid medium and from the ethyl acetate extract of P. polymyxa ALLI-03-01 cultivated in liquid medium L-3-phenyllactic acid was isolated. The antifungal activity of comercial standards of D-(+)- and L-(-)-phenyllactic acid were tested against entomopathogenic fungus B. bassiana and only the L enantiomer presented antifungal activity. Nine cyclo lipodepsipeptides known as fusaricidins were identified in mixture using MALDI-TOF-MS/MS from the methanol extract of ALLI-03-01. The fusaricidins are recognized for their high antimicrobial activity, which was confirmed when two fractions composed by different fusaricidins were tested against the entomopathogenic fungus Metarhizium anisopliae and the pathogenic bacterium Paenibacillus larvae. The fractions showed satisfactory inhibition against both pathogens. Therefore, fusaricidins and selective production of L-3-phenyllactic acid by the bacterium may be colony protection resources, preventing the action of pathogens and allowing healthy larvae development. Therefore, this study reports for the first time a possible symbiotic relationship between Paenibacillus polymyxa ALLI-03-01 and the colony of M. scutellaris bees, as well as production of compounds with high antimicrobial activity by this microorganism that might act as parasite control agents within the colony, establishing a possible ecological relationship between the bacterium and M. scutellaris bees.