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1.
Food Chem ; 460(Pt 2): 140609, 2024 Dec 01.
Artículo en Inglés | MEDLINE | ID: mdl-39094345

RESUMEN

To comprehensively explore the contribution and mechanisms of identified low-threshold bitter substances in Idesia polycarpa var. vestita Diels (I. vestita) fruit, we performed quantification and elucidated their interactions with main bitter taste receptors through molecular docking. The established method for quantifying bitter compounds in I. vestita fruit was validated, yielding satisfactory parameters for linearity, stability, and accuracy. Idescarpin (17.71-101.05 mg/g) and idesin (7.88-77.14 mg/g) were the predominant bitter compounds in terms of content. Taste activity values (TAVs) exceeded 10 for the bitter substances, affirming their pivotal role as major contributors to overall bitterness of I. vestita fruit. Notably, idescarpin with the highest TAV, played a crucial role in generating the bitterness of I. vestita fruit. Hydrogen bonds and hydrophobic interactions were the main driving forces. This study holds potential implications for industrial development of I. vestita fruit by providing novel insights into the mechanism underlying its bitterness formation.


Asunto(s)
Frutas , Gusto , Frutas/química , Humanos , Simulación del Acoplamiento Molecular , Receptores Acoplados a Proteínas G/química , Receptores Acoplados a Proteínas G/metabolismo
2.
Tree Physiol ; 44(4)2024 Apr 03.
Artículo en Inglés | MEDLINE | ID: mdl-38498320

RESUMEN

Methyleugenol, a bioactive compound in the phenylpropene family, undergoes its final and crucial biosynthetic transformation when eugenol O-methyltransferase (EOMT) converts eugenol into methyleugenol. While Melaleuca bracteata F. Muell essential oil is particularly rich in methyleugenol, it contains only trace amounts of its precursor, eugenol. This suggests that the EOMT enzyme in M. bracteata is highly efficient, although it has not yet been characterized. In this study, we isolated and identified an EOMT gene from M. bracteata, termed MbEOMT1, which is primarily expressed in the flowers and leaves and is inducible by methyl jasmonate (MeJA). Subcellular localization of MbEOMT1 in the cytoplasm was detected. Through transient overexpression experiments, we found that MbEOMT1 significantly elevates the concentration of methyleugenol in M. bracteata leaves. Conversely, silencing of MbEOMT1 via virus-induced gene silencing led to a marked reduction in methyleugenol levels. Our in vitro enzymatic assays further confirmed that MbEOMT1 specifically catalyzes the methylation of eugenol. Collectively, these findings establish that the MbEOMT1 gene is critical for methyleugenol biosynthesis in M. bracteata. This study enriches the understanding of phenylpropene biosynthesis and suggests that MbEOMT1 could serve as a valuable catalyst for generating bioactive compounds in the future.


Asunto(s)
Acetatos , Eugenol , Eugenol/análogos & derivados , Melaleuca , Proteínas de Plantas , Eugenol/metabolismo , Proteínas de Plantas/metabolismo , Proteínas de Plantas/genética , Melaleuca/metabolismo , Melaleuca/genética , Metiltransferasas/metabolismo , Metiltransferasas/genética , Regulación de la Expresión Génica de las Plantas , Hojas de la Planta/metabolismo , Hojas de la Planta/genética , Ciclopentanos/metabolismo , Oxilipinas/metabolismo
3.
Food Chem ; 439: 138103, 2024 May 01.
Artículo en Inglés | MEDLINE | ID: mdl-38056337

RESUMEN

Idesia polycarpa var. vestita Diels (I. vestita) has become a promising oil crop due to its easily digestible and highly nutritious fruit oil. However, the intense bitter taste of its fruit greatly limits its development and promotion in the food industry. Herein, five key bitter compounds from I. vestita fruit were isolated by sensory-guided fractionation and characterized using ultra-high performance liquid chromatography-quadrupole time of flight-mass spectrometer and nuclear magnetic resonance. The bitter taste of the identified compounds was subsequently validated by threshold tests and computational molecular docking. The bitterness threshold in water of idesin was the lowest (12.051 mg/L), and all bitter substances spontaneously bound to the bitter receptors hTAS2R16 and hTAS2R14, with a stronger affinity for the latter (approximately -6.5 - -9.0 kcal/mol). This is the first systematic study of bitter compounds in I. vestita fruit, providing a scientific basis for revealing the mechanism of bitterness formation and bitterness control.


Asunto(s)
Frutas , Gusto , Simulación del Acoplamiento Molecular , Espectrometría de Masas , Espectroscopía de Resonancia Magnética
4.
Plants (Basel) ; 12(5)2023 Feb 24.
Artículo en Inglés | MEDLINE | ID: mdl-36903887

RESUMEN

Many aromatic plant volatile compounds contain methyleugenol, which is an attractant for insect pollination and has antibacterial, antioxidant, and other properties. The essential oil of Melaleuca bracteata leaves contains 90.46% methyleugenol, which is an ideal material for studying the biosynthetic pathway of methyleugenol. Eugenol synthase (EGS) is one of the key enzymes involved in the synthesis of methyleugenol. We recently reported two eugenol synthase genes (MbEGS1 and MbEGS2) present in M. bracteata, where MbEGS1 and MbEGS2 were mainly expressed in flowers, followed by leaves, and had the lowest expression levels in stems. In this study, the functions of MbEGS1 and MbEGS2 in the biosynthesis of methyleugenol were investigated using transient gene expression technology and virus-induced gene silencing (VIGS) technology in M. bracteata. Here, in the MbEGSs genes overexpression group, the transcription levels of the MbEGS1 gene and MbEGS2 gene were increased 13.46 times and 12.47 times, respectively, while the methyleugenol levels increased 18.68% and 16.48%. We further verified the function of the MbEGSs genes by using VIGS, as the transcript levels of the MbEGS1 and MbEGS2 genes were downregulated by 79.48% and 90.35%, respectively, and the methyleugenol content in M. bracteata decreased by 28.04% and 19.45%, respectively. The results indicated that the MbEGS1 and MbEGS2 genes were involved in the biosynthesis of methyleugenol, and the transcript levels of the MbEGS1 and MbEGS2 genes correlated with the methyleugenol content in M. bracteata.

5.
Ultrason Sonochem ; 94: 106317, 2023 Mar.
Artículo en Inglés | MEDLINE | ID: mdl-36738695

RESUMEN

Qingke protein rich in restricted amino acids such as lysine, while the uncoordination of ratio of glutenin and gliadin in Qingke protein has a negative impact on its processing properties. In this study, the effect of multiple-frequency ultrasound combined with transglutaminase treatment on the functional and structural properties of Qingke protein and its application in noodle manufacture were investigated. The results showed that compared with the control, ultrasound-assisted transglutaminase dual modification significantly increased the water and oil holding capacity, apparent viscosity, foaming ability, and emulsifying activity index of Qingke protein, which exhibited a higher storage modulus G' (P < 0.05). Meanwhile, ultrasound combined with transglutaminase treatment enhanced the cross-linking degree of Qingke protein (P < 0.05), as shown by decreased free amino group and free sulfhydryl group contents, and increased disulfide bond content. Moreover, after the ultrasound-assisted transglutaminase dual modification treatment, the fluorescence intensity, the contents of α-helix and random coil in the secondary structure of Qingke protein significantly decreased, while the ß-sheet content increased (P < 0.05) compared with control. SDS-PAGE results showed that the bands of Qingke protein treated by ultrasound combined with transglutaminase became unclear. Furthermore, the quality of Qingke noodles made with Qingke powder (140 g/kg dual modified Qingke protein mixed with 860 g/kg extracted Qingke starch) and wheat gluten 60-70 g/kg was similar to that of wheat noodles. In summary, multiple-frequency ultrasound combined with transglutaminase dual modification can significantly improve the physicochemical properties of Qingke protein and the modified Qingke proteins can be used as novel ingredients for Qingke noodles.


Asunto(s)
Almidón , Transglutaminasas , Transglutaminasas/química , Estructura Secundaria de Proteína , Viscosidad
6.
Food Chem ; 404(Pt A): 134634, 2023 Mar 15.
Artículo en Inglés | MEDLINE | ID: mdl-36444026

RESUMEN

Idesia polycarpa var. vestita Diels fruits oil (IPO) has the potential to broaden the availability of healthy vegetable oil and relieve pressure on the edible oil supply. In this study, we compared the physicochemical, bioactivity, and digestive properties of IPO, olive oil (OO), and soybean oil (SO) to comprehensively evaluate the edible potential of IPO. The results revealed no significant differences in relative density or refractive index among the three oils. IPO was rich in ß-sitosterol (366.74 mg/100 g), ß-tocopherol (8.42 mg/100 g), and α-tocopherol (37.10 mg/100 g). The digestive properties of IPO emulsion were investigated for the first time using in vitro simulated digestion. The IPO emulsion stood out regarding its free fatty acid release (88.03 %). Finally, the IPO emulsion released mainly unsaturated fatty acids and had a higher monoacylglycerol content. This study provides new insights into IPO as a high-quality edible vegetable oil.


Asunto(s)
Frutas , Salicaceae , Emulsiones , Digestión , Aceites de Plantas
7.
Food Res Int ; 162(Pt A): 111964, 2022 12.
Artículo en Inglés | MEDLINE | ID: mdl-36461214

RESUMEN

The perceptible bitterness of Zanthoxylum schinifolium Sieb. et Zucc is an important factor limiting its consumption. Metabolomics was used to identify potentially bitter metabolites during the development of Z. schinifolium, and dynamic changes in 17 key bitter components were characterized. The key bitter components in Z. schinifolium at different developmental stages were mainly synthesized through the "phenylpropanoid biosynthesis", "flavonoid biosynthesis", and "flavone and flavonol biosynthesis" pathways. In combination with transcriptomic data, the expression of related genes regulates the accumulation process of these bitter components; based on this, a biosynthetic pathway of bitter components in Z. schinifolium was constructed. In addition, quercetin-3-galactoside, isoquercitin, quercitrin, kaempferol, and isorhamnetin were identified as the main sources of bitterness in mature Z. schinifolium based on an evaluation of taste activity value. These findings provide valuable information for understanding mechanisms underlying Z. schinifolium bitterness and promoting the further development of high-quality Z. schinifolium.


Asunto(s)
Gusto , Zanthoxylum , Metabolómica , Metabolismo Secundario , Transcriptoma
8.
J Food Sci ; 87(9): 3841-3855, 2022 Sep.
Artículo en Inglés | MEDLINE | ID: mdl-35988127

RESUMEN

Idesia polycarpa var. vestita Diels is a perennial deciduous tree widely distributed throughout China. Four I. polycarpa fruit of different cultivars with different fruit issues during the growth process were compared, which were on the basis of morphological characteristics and chemical compositions. The influencing factors of oil accumulation in I. polycarpa fruit and the correlation between different components were investigated, and the results revealed a negative correlation between oil content and total sugar (r = -0.930), ash (r = -0.606), and crude fiber (r = -0.952). Except for oil, none of the chemical components changed substantially during the growing phase, and most cultivars showed higher oil content in the pulp portion (14.14-43.99 g/100 g). Linoleic acid was the most abundant fatty acid in I. polycarpa oil (IPO), with values ranging from 52.18% to 66.65% (fruit), 55.44% to 65.15% (pulp), and 68.99% to 78.76% (seed). Principal component analysis revealed that Hubei varieties are more advantageous. Besides, the lipid composition of IPO was identified by ultrahigh-performance liquid chromatography coupled with electrospray ionization Q-Exactive Focus mass spectrometry. The glyceride components of IPO were mostly composed of 22 triacylglycerols, 30 diacylglycerols, and 8 monoacyglycerols. Meanwhile, linoleic acid was mainly distributed in sn-2 and sn-3 positions. PRACTICAL APPLICATION: Morphologic characteristics, chemical compositions, oil fatty acid profiles, and oil correlation factors of I. polycarpa were analyzed. The comprehensive score of oil quality by PCA in Hb fruit was the highest. The glyceride components of I. polycarpa oil were mainly composed of 22 triacylglycerols, 30 diacylglycerols, and eight monoacyglycerols.


Asunto(s)
Ácido Linoleico , Salicaceae , Diglicéridos , Ácidos Grasos/análisis , Glicéridos , Salicaceae/química , Azúcares , Triglicéridos/análisis
9.
Eur J Med Chem ; 207: 112795, 2020 Dec 01.
Artículo en Inglés | MEDLINE | ID: mdl-33002845

RESUMEN

In this present study, a series of 5-phenyl-2-furan and 4-phenyl-2-oxazole derivatives were designed and synthesized as phosphodiesterase type 4 (PDE4) inhibitors. In vitro results showed that the synthesized compounds exhibited considerable inhibitory activity against PDE4B and blockade of LPS-induced TNF-α release. Among the designed compounds, Compound 5j exhibited lower IC50 value (1.4 µM) against PDE4 than parent rolipram (2.0 µM) in in vitro enzyme assay, which also displayed good in vivo activity in animal models of asthma/COPD and sepsis induced by LPS. Docking results suggested that introduction of methoxy group at para-position of phenyl ring, demonstrated good interaction with metal binding pocket domain of PDE4B, which was helpful to enhance inhibitory activity.


Asunto(s)
Ácidos Carboxílicos/síntesis química , Ácidos Carboxílicos/farmacología , Diseño de Fármacos , Fura-2/química , Oxazoles/química , Inhibidores de Fosfodiesterasa 4/síntesis química , Inhibidores de Fosfodiesterasa 4/farmacología , Animales , Ácidos Carboxílicos/química , Ácidos Carboxílicos/metabolismo , Técnicas de Química Sintética , Fosfodiesterasas de Nucleótidos Cíclicos Tipo 4/química , Fosfodiesterasas de Nucleótidos Cíclicos Tipo 4/metabolismo , Femenino , Humanos , Concentración 50 Inhibidora , Masculino , Ratones , Simulación del Acoplamiento Molecular , Inhibidores de Fosfodiesterasa 4/química , Inhibidores de Fosfodiesterasa 4/metabolismo , Conformación Proteica , Ratas , Relación Estructura-Actividad
10.
J Agric Food Chem ; 67(43): 11867-11876, 2019 Oct 30.
Artículo en Inglés | MEDLINE | ID: mdl-31584805

RESUMEN

Bacterial leaf blight (BLB) caused by Xanthomonas oryzae pv oryzae (Xoo) is considered as the most destructive disease of rice. The use of bactericides is among the most widely used traditional methods to control this destructive disease. The excessive and repeated use of the same bactericides is also becoming the reason behind the development of bactericide resistance. The widely used method for finding the new antimicrobial agents often involves the bacterial virulence factors as a target without affecting bacterial growth. Type III secretion system (T3SS) is a protein appendage and is considered as having essential virulence factors in most Gram-negative bacteria. Due to the conserved construct, T3SS has been regarded as an important mark for the blooming of novel antimicrobial drugs. Toward the search of new T3SS inhibitors, an alternative series of 1,3-thiazole derivatives were designed and synthesized. Their structures were characterized and confirmed by 1H NMR, 13C NMR, MS, and elemental analysis. All the title compounds inhibited the promoter activity of hpa1 gene significantly. Eight of them showed better inhibition than our previous T3SS inhibitor TS006 (o-coumaric acid, OCA). The treatment of Xoo with eight compounds significantly attenuated HR without affecting bacterial growth. The mRNA levels of some representative genes (hrp/hrc genes) were reduced up to different extents. In vivo bioassay results showed that eight T3SS inhibitors could reduce bacterial leaf blight and bacterial leaf streak symptoms on rice, significantly.


Asunto(s)
Antibacterianos/farmacología , Proteínas Bacterianas/antagonistas & inhibidores , Furanos/farmacología , Oryza/microbiología , Enfermedades de las Plantas/microbiología , Sistemas de Secreción Tipo III/antagonistas & inhibidores , Xanthomonas/efectos de los fármacos , Antibacterianos/síntesis química , Antibacterianos/química , Proteínas Bacterianas/genética , Proteínas Bacterianas/metabolismo , Furanos/química , Regulación Bacteriana de la Expresión Génica/efectos de los fármacos , Sistemas de Secreción Tipo III/genética , Sistemas de Secreción Tipo III/metabolismo , Xanthomonas/genética , Xanthomonas/metabolismo
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