Shatianyu dietary fiber (Citrus grandis L. Osbeck) promotes the production of active metabolites from its flavonoids during in vitro colonic fermentation.

BACKGROUND: Recent studies reveal that dietary fiber (DF) might play a critical role in the metabolism and bioactivity of flavonoids by regulating gut microbiota. We previously found that Shatianyu (Citrus grandis L. Osbeck) pulp was rich in flavonoids and DF, and Shatianyu pulp flavonoid extracts (SPFEs) were dominated by melitidin, obviously different from other citrus flavonoids dominated by naringin. The effects of Shatianyu pulp DF (SPDF) on the microbial metabolism and bioactivity of SPFEs is unknown. RESULTS: An in vitro colonic fermentation model was used to explore the effects of SPDF on the microbial metabolism and antioxidant activity of SPFEs in the present study. At the beginning of fermentation, SPDF promoted the microbial degradation of SPFEs. After 24 h-fermentation, the supplemented SPFEs were almost all degraded in SPFEs group, and the main metabolites detected were the dehydrogenation, hydroxylation and acetylation products of naringenin, the aglycone of the major SPFEs components. However, when SPFEs fermented with SPDF for 24 h, 60.7% of flavonoid compounds were retained, and SPFEs were mainly transformed to the ring fission metabolites, such as 3-(4-hydroxyphenyl) propionic acid, 3-phenylpropionic acid and 3-(3-hydroxy-phenyl) propionic acid. The fermentation metabolites of SPFEs showed stronger antioxidant activity than the original ones, with a further increase in SPDF supplemented group. Furthermore, SPFEs enriched microbiota participating in the deglycosylation and dehydrogenation of flavonoids, while co-supplementation of SPDF and SPFEs witnessed the bloom of Lactobacillaceae and Lactobacillus, contributing to the deglycosylation and ring fission of flavonoids. CONCLUSION: SDPF promote SPFEs to transform to active metabolites probably by regulating gut microbiota. © 2023 Society of Chemical Industry.

Carotenoid-Derived Flavor Precursors from Averrhoa carambola Fresh Fruit.

The fruit of Averrhoa carambola L. (Oxalidaceae), commonly known as star fruit or carambola, is popular in tropical and subtropical regions. Carotenoid-derived components, mainly C13- and C15-norisoprenoids, contribute greatly to the flavor of star fruit. Previously reported norisoprenoids were tentatively identified by GC-MS analysis after enzymatic hydrolysis. To gain accurate information about glycosidically bound flavor precursors in star fruit, a phytochemical study was conducted, which led to the isolation of 16 carotenoid derivatives-One new C13-norisoprenoid glucoside, (5R,6S,7E,9R)-5,6,9-trihydroxy-7-megastigmene 9-O-ß-d-glucoside (1); one new C15-norisoprenoid, (6S,7E,10S)-Δ9,15-10-hydroxyabscisic alcohol (11); and 14 known ones, of which 12 were in glucoside form. The structures of the two new compounds were elucidated on the basis of extensive spectroscopic data analysis and chemical reaction. Compound 11 was a rare C15-norisoprenoid with a double bond between C-9 and C-15, and its possible biogenetic pathway was proposed. The known compounds were identified by comparison of their mass and nuclear magnetic resonance (NMR) data with those reported in the literature. The structure identification of one new (1) and seven known (3⁻7, 9, and 10) C13-norisoprenoid glucosides from the genus Averrhoa for the first time enriches the knowledge of carotenoid-derived flavor precursors in star fruit.

Anti-MRSA Sesquiterpenes from the Semi-Mangrove Plant Myoporum bontioides A. Gray.

The striking rise of methicillin-resistant Staphylococcus aureus (MRSA) infections has become a serious threat to public health worldwide. In an effort to search for new anti-MRSA agents from natural products, a bioassay-guided phytochemical study was conducted on the semi-mangrove plant Myoporum bontioides A. Gray, which led to the isolation of two new sesquiterpene alkaloids (1 and 2) and six known furanosesquiterpenes (3⁻8). Their structures were elucidated on the basis of extensive analysis of their 1D, 2D NMR and mass spectroscopic data. These two new alkaloids (1 and 2) displayed potent anti-MRSA activity with MIC value of 6.25 µg/mL. This is the first report of sesquiterpene alkaloids from the plants of Myoporum genus and their anti-MRSA activity.

Phenolics from Mikania micrantha and Their Antioxidant Activity.

A phytochemical study on the aerial parts of Mikania micrantha led to the isolation of two new phenolic compounds, benzyl 5-O-ß-d-glucopyranosyl-2,5-dihydroxybenzoate (1) and (7S,8R)-threo-dihydroxydehydrodiconiferyl alcohol 9-acetate (2), together with twelve known compounds, benzyl 2-O-ß-d-glucopyranosyl-2,6-dihydroxybenzoate (3), 4-allyl-2,6-dimethoxyphenol glucoside (4), (+)-isolariciresinol (5), icariol A2 (6), 9,10-dihydroxythymol (7), 8,9,10-trihydroxythymol (8), caffeic acid (9), p-coumaric acid (10), ethyl protocatechuate (11), procatechuic aldehyde (12), 4-hydroxybenzoic acid (13), and hydroquinone (14). Their structures were elucidated on the basis of extensive spectroscopic analysis. Except 8 and 9, all the other compounds were isolated from this plant species for the first time. The antioxidant activity of those isolated compounds were evaluated using three different assays. Compounds 1, 2, 3, 9, 10, 13, and 14 demonstrated significant 2,2'-azinobis-(3-ethylbenzthiazoline-6-sulphonic acid) (ABTS) free radical cation scavenging activity ranging from SC50 0.31 to 4.86 µM, which were more potent than l-ascorbic acid (SC50 = 10.48 µM). Compounds 5, 9, 11, and 12 exhibited more potent 1,1-diphenyl-2-picrylhydrazyl (DPPH) radical scavenging activity (SC50 = 16.24-21.67 µM) than l-ascorbic acid (39.48 µM). Moreover, the ferric reducing antioxidant power (FRAP) of compounds 2, 5, 9, and 11 were discovered to be also comparable to or even more potent than l-ascorbic acid.

Structural elucidation, binding sites exploration and biological activities of bound phenolics from Radix Puerariae Thomsonii.

Radix puerariae thomsonii (RPT) contains many phenolics and exhibits various health benefits. Although the free phenolics in RPT have been identified, the composition and content of bound phenolics, which account for approximately 20% of the total phenolic content, remain unknown. In this study, 12 compounds were isolated and identified from RPT-bound phenolic extracts, of which 2 were novel and 6 were reported first in RPT. ORAC and PSC antioxidant activities of 12 compounds, as well as their effects on alcohol dehydrogenase (ADH), aldehyde dehydrogenase (ALDH), α-glucosidase, and α-amylase were evaluated. Genistein exhibited the highest ORAC activity, while daidzin demonstrated superior PSC activity. Five compounds, including two new compounds, exhibited the ability to activate both ADH and ALDH. All the compounds except 4-hydroxyphenylacetic acid methyl ester and 2,4,4'-trihydroxydeoxybenzoin demonstrated inhibitory effects on α-glucosidase and α-amylase. Alkaline hydrolysis and stepwise enzymatic hydrolysis revealed that bound phenolics in RPT mainly exist within starch.

In vitro human gut microbiota fermentation of litchi pulp polysaccharides as affected by Lactobacillus pre-treatment.

In this study, litchi polysaccharides were obtained from unfermented or fermented pulp by Lactobacillus fermentum (denoted as LP and LPF, respectively). The differences between LP and LPF in the colonic fermentation characteristics and modulatory of gut microbiota growth and metabolism were investigated with an in vitro fecal fermentation model. Results revealed that the strategies of gut bacteria metabolizing LP and LPF were different and LPF with lower molecular weight (Mw) was readily utilized by bacteria. The monosaccharide utilization sequence of each polysaccharide was Ara > Gla > GalA > GlcA ≈ Glu ≈ Man. Moreover, LPF promoted stronger proliferation of Bifidobacterium, Megamonas, Prevotella, and Bacteroides and higher SCFAs production (especially acetic and butyric acids) than LP. Correlation analysis further revealed that Mw could represent an essential structural feature of polysaccharides associated with its microbiota-regulating effect. Overall, Lactobacillus fermentation pre-treatment of litchi pulp promoted the fermentation characteristics and prebiotic activities of its polysaccharide.

Free and bound phenolic profiles of Radix Puerariae Thomsonii from different growing regions and their bioactivities.

The free and bound phenolic profiles and their bioactivities of radix puerariae thomsonii (RPT) cultivars from 7 growing regions in China were investigated. Total phenolic and flavonoid contents were from 148.71 to 435.32 mg gallic acid equivalents /100 g dry weight and 561.93 to 826.11 mg catechin equivalents /100 g dry weight, respectively, with 20.64-38.28% and 32.77-47.29% contribution from bound fractions. Sixteen phenolic compounds were detected in RPTs. Bound fractions contributed 28.15-70.84% to the total antioxidant activities. The cultivars from Qiannan and Guangzhou showed much higher regulatory effects on carbohydrate hydrolyzing enzymes and alcohol metabolizing enzymes than the other cultivars. The bound fractions exhibited equivalent EC50 values for alcohol metabolizing enzymes and IC50 values for carbohydrate hydrolyzing enzymes to the free fractions in RPT cultivars. Therefore, bound phenolics significantly contributed to the potential health benefits of RPT. The results provided information for the utilization of RPT for health promoting purpose.

Modulation effect of black rice dietary fiber on the metabolism and fermentation of cyanidin-3-glucoside in an in vitro human colonic model.

Black rice (Oryza sativa L.) is a great source of anthocyanins and dietary fiber and possesses various health-promoting properties. The modulating effect of insoluble dietary fiber (IDF) from black rice on the fermentation of cyanidin-3-O-glucoside (Cy3G) in an in vitro human colonic model, together with the possible microbiota-mediated mechanisms, was investigated. The combined Cy3G and IDF fermentation can promote the biotransformation of Cy3G into phenolic compounds such as cyanidin and protocatechuic acid with stronger antioxidant activities and increase the total production of SCFAs during the fermentation of Cy3G. 16S rRNA sequencing analysis revealed that the addition of IDF modulated the microbiota structure and bloomed Bacteroidota and Prevotellaceae-related genera, which were positively correlated with metabolites of Cy3G, thus potentially regulating the microbial metabolism of Cy3G. The work is of great significance for elucidating the material basis of the health benefits of black rice.

Purification, Characterization and Bioactivity of Different Molecular-Weight Fractions of Polysaccharide Extracted from Litchi Pulp.

Litchi polysaccharides are a kind of macromolecular polymers with various biological activities and a wide range of molecular weights. In this study, two separate fractions, with average molecular weights of 378.67 kDa (67.33%) and 16.96 kDa (6.95%), which were referred to as LP1 and LP2, respectively, were separated using an ultrafiltration membrane. Their physicochemical properties, and immunomodulatory and prebiotic activity were compared. The results revealed that LP2 contained more neutral sugar, arabinose, galactose and rhamnose, but less uronic acid, protein, mannose and glucose than LP1. Compared with LP1, LP2 possessed higher solubility and lower apparent viscosity. LP2 exhibited stronger stimulation on macrophage secretion of NO, TNF-α and IL-6, as well as better proliferation of Lactobacillus plantarum, Leuconostoc mesenteroides, Lactobacillus casei and Bifidobacterium adolescentis. These results suggest that an ultrafiltration membrane might be used to prepare a highly-active polysaccharide fraction from litchi pulp that may be used for food or drug development.

Carambolaside W Inhibited H1N1 Influenza Virus-Induced Oxidative Stress through STAT-3/BCL-XL Signaling Pathway.

The H1N1 influenza virus is highly infectious and pathogenic, and in recent years, it has often presented seasonal mass outbreaks of infection. People infected with H1N1 will develop a high fever and other respiratory infection symptoms. If not treated in time, complications such as pneumonia may occur. In this study, we focused on developing drugs that can effectively fight against with H1N1 virus. A flavonoid glycoside was extracted from the carambola, then characterized by HR-ESI-MS with the molecular formula C47H58O2, and named carambolaside W. The flavonoid glycosides were found to have good anti-H1N1 influenza virus effects. In this study, we verified that carambolaside W has low toxicity and can effectively inhibit influenza virus replication in vitro. H1N1 virus infection induces intracellular oxidative stress damage to accelerate disease progression. The results showed that carambolaside W effectively inhibited the oxidative stress caused by H1N1 infection. The Western blot assay also revealed that carambolaside W alters the expression of apoptosis-related proteins in vitro and exerts a good anti-H1N1 influenza virus effect. In summary, carambolaside W is a low-toxicity natural flavonoid that can effectively treat the H1N1 influenza virus as a potential anti-H1N1 virus agent.

Neutron Irradiation Effects on Boron Nitride-Based Ceramics for Use in X-ray Detection.

X-ray detectors based on conventional semiconductors with large atomic numbers are suffering from the poor stability under a high dose rate of ionizing irradiation. In this work, we demonstrate that a wide band gap ceramic-boron nitride with small atomic numbers could be used for sensitive X-ray detection. Boron nitride samples showed excellent resistance to ionizing radiation, which have been systematically studied with the neutron- and electron-aging experiments. Then, we fully analyzed the influence of these aging effects on the fundamental properties of boron nitride. Interestingly, we found that the boron nitride samples could maintain relatively good charge transport properties even after large dose of neutron irradiation. The fabricated X-ray detectors showed decent performance metrics, and the neutron-aged boron nitride even showed improved operational stability under continuous X-ray irradiation, suggesting the great potential for real applications.

A new benzofuran glycoside from the fruit of Clausena lansium.

In this work, we isolated a new benzofuran glycoside, 6-ß-d-glucosyl-6,7-dihydroxy-5-benzofuranpropanoic acid methyl ester (1), together with six known compounds (2-7) from the fruits of Clausena lansium (Lour.) Skeels. Extensive spectroscopic methods were employed to elucidate their structures. Herein, compounds 2, 3, 5 and 6 were reported from Clausena lansium (Lour.) Skeels for the first time. Moreover, compounds 1, 2, 4 and 6 showed comparable 2,2'-azino-bis(3-ethylbenzthiazoline-6-sulphonic acid) (ABTS) radical scavenging activity to l-ascorbic acid, and compound 4 also exhibited potent 1,1-diphenyl-2-picrylhydrazyl (DPPH) radical scavenging activity and ferric reducing antioxidant power (FRAP). All of the compounds showed oxygen radical absorbance capacity (ORAC) values ranging from 0.3 to 3.6 µmol trolex equivalent/µmol. In addition, compounds 3 and 5 also demonstrated good α-amylase inhibitory activity.

Structure determination, bitterness evaluation and hepatic gluconeogenesis inhibitory activity of triterpenoids from the Momordica charantia fruit.

Triterpenoids are hypoglycemic substances and flavor components of Momordica charantia L., whether their bitterness correlated with hypoglycemic potential remain unknown. Thus, triterpenoids in M. charantia were isolated by phytochemical methods and identified by spectroscopic analysis. The bitterness levels and hypoglycaemic activity of isolated triterpenoids were evaluated by electronic tongue and hepatic gluconeogenesis assay. Eighteen triterpenoids including two new ones, Momordicoside Y and Z, were identified. Among the six identified bitter triterpenoids, karaviloside III, goyaglycoside C, and momordicoside F2 were bitterer than caffeine (P < 0.05), with caffeine equivalent (CE) values of 289.19, 4.32, and 41.24 mg CE/mg, respectively. Momordicoside Y, charantoside C, momordicoside F1, and momordicoside G could inhibit hepatic gluconeogenesis by 23.9%, 36.2%, 33.4%, 34.4% at 40 µM, respectively. These four compounds could interact with active site of phosphoenolpyruvate carboxykinase in molecular docking simulation. No correlation was observed between hepatic gluconeogenesis inhibitory activity and bitterness of triterpenoids.

α-Glucosidase inhibitors from brown rice bound phenolics extracts (BRBPE): Identification and mechanism.

Brown rice bound phenolics extracts (BRBPE) have been reported to possess α-glucosidase inhibitory effects, the specific enzyme inhibitors involved in this process were unknown. Here, α-glucosidase inhibitors in BRBPE were screened using bioaffinity ultrafiltration methods, and seven phenolic compounds - three monomers (p-coumaric acid, ferulic acid and methyl ferulate), three dimers (8-5', 5-5' and 8-O-4' diferulic acid) and a trimer (5-5'/8-O-4″ dehydrotriferulic acid) were identified as exact inhibitors, among which 5-5'/8-O-4″ dehydrotriferulic acid and 5-5'diferulic acid exhibited the best inhibitory activity. Enzyme kinetic analysis suggested that the inhibitory mechanism of these seven inhibitors including competitive, noncompetitive, uncompetitive and mixed manner. Molecular docking analysis revealed that the seven inhibitors bind with α-glucosidase mainly by hydrogen bonding interaction, hydrophobic force and ionic bond. Molecular dynamics simulation further explored the structure and molecular property of phenolic-glucosidase complex. This work provided a deep insight into brown rice bound phenolics acting as potent α-glucosidase inhibitors.

Enhanced Tribocatalytic Degradation of Organic Pollutants by ZnO Nanoparticles of High Crystallinity.

More and more metal oxide nanomaterials are being synthesized and investigated for degradation of organic pollutants through harvesting friction energy, yet the strategy to optimize their performance for this application has not been carefully explored up to date. In this work, three commercially available ZnO powders are selected and compared for tribocatalytic degradation of organic dyes, among which ZnO-1 and ZnO-2 are agglomerates of spherical nanoparticles around 20 nm, and ZnO-3 are particles of high crystallinity with a regular prismatic shape and smooth surfaces, ranging from 50 to 150 nm. Compared with ZnO-1 and ZnO-2, ZnO-3 exhibits a much higher tribocatalytic degradation performance, and a high degradation rate constant of 6.566 × 10-2 min-1 is achieved for RhB, which is superior compared with previous tribocatalytic reports. The stability and universality of ZnO-3 were demonstrated through cycling tests and degradation of different types of dyes. Furthermore, the mechanism of tribocatalysis revealed that h+ was the main active species in the degradation process by ZnO. This work highlights the great significance of high crystallinity rather than a large specific surface area for the development of high-performance tribocatalysts and demonstrates the great potential of tribocatalysis for water remediation.

Phenolic profiles and bioactivities of different milling fractions of rice bran from black rice.

Phytochemicals are unevenly distributed in grain kernels and concentrated in bran fractions. However, their specific distribution in the grain bran, especially colored grains, is not clarified. This study divided rice bran from black rice into five fractions by stepwise milling to obtain BF1(outermost layer) to BF5 (the innermost layer). Each fraction accounted for approximately 2% of the whole kernel. The total content of phenolics (TPC), flavonoids (TFC), and anthocyanins (TAC) of five fractions significantly decreased from BF1 to BF5. The TPC, TFC and TAC of BF1 contribute 25.7%, 28.2%, 28.4% to the total of five fractions, respectively. HPLC analysis showed that the contents of most anthocyanin and phenolic acids compounds decreased from BF1 to BF5. Together with α-glucosidase and α-amylase inhibitory activities of BF1, the antioxidant activity was higher than those of other fractions. These results can guide the moderate processing of black rice and the utilization of its bran.

The flavonoid profiles in the pulp of different pomelo (Citrus grandis L. Osbeck) and grapefruit (Citrus paradisi Mcfad) cultivars and their in vitro bioactivity.

Previous results indicated that the flavonoid profiles might have varietal differences in pomelo, but detailed information is unknown. We previously isolated 4 new flavonoids, cigranoside C, D, E, F, in Citrus grandis Shatianyu pulp. However, their distribution in different pomelo cultivars remains to be explored. Therefore, the flavonoid profiles and in vitro bioactivity of the pulp from 5 pomelo and 1 grapefruit cultivars commonly consumed in China were investigated. Fourteen flavonoids were identified, cigranoside C, D, E were detected in these pomelo and grapefruit. Naringin and cigranoside C were the major flavonoids in grapefruit, Guanximiyu-W, Guanximiyu-R and Liangpingyu, while melitidin and rhoifolin was the predominant flavonoid in Shatianyu and Yuhuanyu, respectively. Pomelo and grapefruit showed strong antioxidant activity, and were potent inhibitors of pancreatic lipase with IC50 values of 11.4-72.6 mg fruit/mL except Shatianyu. Thus, pomelo and grapefruit are natural antioxidants and possess anti-obesity potential.

Physicochemical properties and prebiotic activities of polysaccharides from Zizyphus jujube based on different extraction techniques.

Zizyphus jujube polysaccharide was extracted with hot water, ultrahigh pressure, deep eutectic solvent (DES) and ultrahigh pressure-assisted DES. Comparative analyses were conducted on the yield, physicochemical properties and prebiotic activity of four polysaccharides (JP-H, JP-U, JP-D and JP-UD). The yield of JP-UD (10.42 %) was 3.3 times that of JP-H (3.12 %), and its sugar content was the highest. JP-UD possessed the lowest Mw, while JP-H possessed the highest. Four JPs were acidic pyranose and mainly composed of galacturonic acid, arabinose and galactose. NMR results demonstrated that they contained not only similar glycosidic linkage but also the specific glycosidic linkage of →4)-α-D-Glcp-(l→ appeared in JP-U and JP-UD, the esterified units of GalA and CONH2 group appeared in JP-D and JP-UD, and the Terminal ß-D-Galp and →4)-α-GalpA-(1→ appeared in JP-UD. JPs showed different proliferation effects on four lactobacillus strains, among which JP-UD exhibited the strongest prebiotic activity. Zizyphus jujube polysaccharides have great potential for application in the functional food and medical industry.

Structural elucidation of flavonoids from Shatianyu (Citrus grandis L. Osbeck) pulp and screening of key antioxidant components.

The Citrus genus is a good source of dietary flavonoids, which have many health benefits. As a representative citrus fruit, the flavonoids composition in Shatianyu (Citrus grandis L. Osbeck) pulp remains to be investigated. In the present study, 11 flavonoids were isolated and identified from Shatianyu pulp flavonoid extracts (SPFEs). Among them, 4 flavonoids were previously undescribed and 2 flavonoids were firstly isolated from pummelo. The cellular antioxidant activity (CAA) and oxygen radical absorbance capacity (ORAC) of isolated compounds were evaluated. Naringin and rhoifolin showed the highest ORAC activity, and the presence of a 3-hydroxy-3-methylglutaryl or a 4'-glucose decreased the ORAC activity of flavonoids. The contribution of isolated flavonoids to the holistic antioxidant activity of SPFEs was determined by an online knockout method. Melitidin, bergamjuicin and naringin contributed most to ORAC activity, while bergamjuicin, melitidin and apigenin-4'-O-ß-d-glucopyranosyl-7-O-α-l-rhamnopyranosyl-(1 â†’ 2)-[6″-O-(3- hydroxy-3-methylgltaryl)]-ß-d-glucopyranoside contributed most to CAA activity.

Variation in characterization and probiotic activities of polysaccharides from litchi pulp fermented for different times.

This study investigated the chemical structures and probiotic potential of different polysaccharides (LPs) extracted from the litchi pulp that fermented with Lactobacillus fermentum for different times (i.e., 0-72 h corresponding to LP-0 through LP-72, respectively). Fermentation times affected the yields, total sugar contents, uronic acid contents, molecular weights, and monosaccharide compositions of LPs. The LPs yields and uronic acid contents exhibited irregular trends in association with fermentation time, while total sugar contents decreased, and the molecular weights increased. Particularly, LP-6 contained the highest extraction yields (2.67%), lowest uronic acid contents, and smallest average Mw (104 kDa) (p < 0.05). Moreover, analysis of the monosaccharide composition in the fermented LPs indicated that the proportions of glucose decreased, while arabinose and galacturonic acid proportions increased relative to unfermented LP-0. Further, LP-6 demonstrated the highest growth for Bifidobacterium compared to LP-0, while the other fermentation time led to comparable or worse probiotic promoting activities. These results suggest that lactic acid bacteria fermentation alters the physicochemical properties of litchi polysaccharides, such that suitable fermentation time can enhance their probiotic activities.