It was confirmed that complex fermentation (CF) was more efficient than single-strain fermentations in inducing changes in the contents of phenolic compounds of Maclura tricuspidate and Pyrus Montana Nakai. A mixture of Maclura tricuspidata, Pyrus montana Nakai, Platycodon grandiflorum and Codonopsis lanceolata were fermented in CF using Aspergillus shirousamii (koji), yeast, and lactic acid bacteria (LAB) for 24 days, and the pH, °Brix, total acidity, anti-oxidant activity, polyphenol content, nitric oxide (NO), and Western blotting of inducible nitric oxide synthase (iNOS), cyclo-oxygenase-2 (COX-2), and tumor necrosis factor-α (TNF-α) of the sample were determined. There was no significant change in pH and total acidity. °Brix significantly decreased from day 6 onwards. HPLC confirmed that the concentrations of chlorogenic acid, 4-hydrobenzoic acid, vanillic acid, and caffeic acid significantly increased from day 18 during the fermentation. Additionally, DPPH, ABTS radical scavenging activity, total phenol, and total flavonoid were confirmed to be increased until 18 days. NO was significantly inhibited from day 6, along with significant inhibition of iNOS, COX-2, and TNF-a. In conclusion, this study confirmed that CF of low-use (or underutilized) wild vegetables enhances phenolic compounds. It effectively suppresses NO, iNOS, COX-2, and TNF-α, markers of inflammation-related pathogenesis. Altogether, our results suggest that CF of the above plants has a potential anti-inflammatory effect.

Parishin compounds are rare polyphenolic glucosides mainly found in the rhizome of the traditional Chinese medicinal plant, Gastrodia elata. These constituents are reported to have several biological and pharmacological activities. In the present study, two novel parishin derivatives not previously reported as plant-based phytochemicals were identified from a twig of Maclura tricuspidata (MT) and two new compounds were elucidated as 1-(4-(β-d-glucopyranosyloxy)benzyl)-3-hydroxy-3-methylpentane-1,5-dioate (named macluraparishin E) and 1,3-bis(4-(β-d-glucopyranosyloxy)benzyl)-3-hydroxy-3-methylpentane- 1,5-dioate (macluraparishin C), based on the experimental data obtained by UV–Visible (UV–Vis) spectroscopy, high performance liquid chromatography–quadrupole time-of-flight mass spectrometry (HPLC-QTOF-MS) and nuclear magnetic resonance (NMR) spectroscopy. Additionally, gastrodin, parishin A and parishin B were positively identified by spectroscopic evidence and the comparison of HPLC retention time with the corresponding authentic standards. Gastrodin, parishin A and parishin B, macluraparishin E and macluraparishin C were found to be the most abundant constituents in the MT twig. The compositions and contents of these constituents were found to vary depending on the different parts of the MT plant. In particular, the contents of parishin A, parishin B, macluraparishin C and macluraparishin E were higher in the twig, bark and root than in the leaves, xylem and fruit.

This study investigated the essential oil composition of fresh Panax ginseng root and identified novel compounds from ginseng oil. The oil was divided into five fractions (neutral, basic, phenolic, acidic, and aldehydic). In total, 149 constituents, including 29, 19, and 38 compounds in the basic, phenolic, and aldehydic fractions, respectively, were identified by gas chromatography (GC) and GC-mass spectrometry (MS). The primary constituents of the total ginseng volatile oil were α-humulene (13.91% as a peak area), bicyclogermacrene (13.59%), β-caryophyllene (8.24%), α-neoclovene (7.78%), and α- and β-panasinsenes (5.14% and 7.53%). The primary constituents of the basic fraction were 2-isopropyl-3-methoxypyrazine (35.51%), 3-sec-butyl-2-methoxy-5-methylpyrazine (31.54%), 2-isobutyl-3-methoxypyrazine (8.64%), and 2-methoxy-3-methylpyrazine (8.40%), whereas in the phenolic fraction, these were benzoic (25.40%), octanoic (11.57%), nonanoic (9.16%), propionic (6.35%), and decanoic acids (6.16%). The primary constituents of the aldehydic fraction were 4-(2-furyl)-3-buten-2-one (23.41%), benzaldehyde (10.18%), cis-2-heptanal (9.42%), 3-(α-furyl)-propenal (8.51%), and 2-phenyl-2-butenal (7.28%). Among these, the phenylalkenal compounds, including 2-phenyl-2-butenal, 2-methyl-3-phenyl-2-propenal, 5-methyl-2-phenyl-2-pentenal, 5-methyl-2-phenyl-2-hexenals, 2-phenyl-2-octenal, and 2-phenyl-2-nonenal, were newly identified in this study as ginseng volatile constituents. Furthermore, 2-phenyl-2-nonenal was identified as a plant-based volatile constituent for the first time in this study.

Beta-aminoisobutyric acid (BAIBA) and branched-chain amino acids (BCAA) have recently received considerable attention because of their various health benefits. In this study, the hydrolysis characteristics of chicken breast for 11 commercially proteolytic enzymes were studied to evaluate the effect of protease type, reaction pH (5-8), leaction time (2-24 h) and enzyme concentration (0.25-8%), and the effect of two combined enzymes for the preparation of BAIBA- and BCAA-enriched chicken breast hydrolysates. The content of BAIBA was higher in hydrolysate by prozyme 2000P (38.72±3.01 mg/g, dry weight base), foodpro alkaline protease (30.24±2.54 mg/g) and alcalase (26.24±1.01 mg/g) while the BCAA content was higher in prozyme 2000P (108.96±2.63 mg/g), flavourzyme (81.12±4.78 mg/g) and sumizyme LP (62.88±3.83 mg/g). As the effects of reaction pH, time, and amount of added enzymes, the optimum condition for the preparation of BAIBA- and BCAA-enriched hydrolysates were as follows; reaction pH 6-7, reaction time 8-16 h and the amount of enzyme 4% (w/w) based on the dried chicken breast. However, no significant increase of BAIBA and BCAA content was observed when hydrolyzed with two combined enzymes. These results suggest that commercial proteolytic enzymes can be applied to prepare BAIBA- and BCAA-enriched chicken breast hydrolysates.

Ripe fruit of Maclura tricuspidata has been traditionally used as a raw material for the preparation of fermented foods such as wine and vinegar in Korea. This studies were carried out to investigate changes of nutritional (soluble solids, free sugars and free and total amino acid composition) and bioactive constituents (phenolic compounds and parishin derivatives) during the liquid fermentation of M. tricuspidata fruits with Armillaria mellea (honey mushroom). The soluble solid, free sugars and free amino acids were gradually decreased during fermentation while meaningful changes of pH and total amino acids did not observed even after 10 day fermentation. The content of phenolic acids, particularly chlorogenic acid and parishin derivatives were decreased while that of caffeic acid and 4-hydroxybenzyl alcohol (4-HBA) were increased during the 10 day fermentation period. The crude enzyme preparation from liquid culture of A. mellea biotransformed parishin A into 4-HBA via parishin B, parishin C and gastrodin with high transformation ratio. Based on the results above, we discovered that parishin A and its derivatives are transformed into 4-HBA via parishin B, parishin C and gastrodin by esterase and β-glucosidase secreted by the mushroom mycelia during fermentation.

Ripe fruits of Maclura tricuspidata (MT) are used as food material and a natural colorant in Korea. Although MT fruits have a deep red color due to carotenoid-like pigments, their chemical nature has not been explored in detail so far. The present study aimed at elucidating the chemical structures and composition of carotenoids in MT fruits and changes at different maturity stages. Two carotenoids from saponified MT fruit extract were isolated using repeated silica gel column chromatography. Based on interpretations of spectroscopic data, these compounds were determined as keto-carotenoids, i.e., capsanthin (3,3′-dihydroxy-β,κ-caroten-6′-one) and cryptocapsin (3′-hydroxy-β,κ-caroten-6’-one), and the contents of individual carotenoids were quantified with HPLC based on calibration curves obtained from authentic standards. The contents of capsanthin and cryptocapsin in the sample of saponified MT fruits were 57.65 ± 1.97 µg/g and 171.66 ± 4.85 μg/g as dry weight base (dw). The majority of these keto-carotenoids in the MT fruits were present in esterified forms with lauric, myristic or palmitic acid rather than in their free forms. The results also showed that esterification of these compounds occurred starting from early stage (yellow-brownish stage) of maturation. Considering the high cryptocapsin content, MT fruits can be applied as a potentially valuable source of cryptocapsin for food and medicinal application as well as a source of provitamin A.

Free radical generation and oxidative stress push forward an immense influence on the pathogenesis of neurodegenerative diseases such as Alzheimer’s disease and Parkinson’s disease. Maclura tricuspidata fruit (MT) contains many biologically active substances, including compounds with antioxidant properties. The current study aimed to investigate the neuroprotective effects of MT fruit on hydrogen peroxide (H2O2)-induced neurotoxicity in SH-SY5Y cells. SH-SY5Y cells were pretreated with MT, and cell damage was induced by H2O2. First, the chemical composition and free radical scavenging properties of MT were analyzed. MT attenuated oxidative stress-induced damage in cells based on the assessment of cell viability. The H2O2-induced toxicity caused by ROS production and lactate dehydrogenase (LDH) release was ameliorated by MT pretreatment. MT also promoted an increase in the expression of genes encoding the antioxidant enzymes superoxide dismutase (SOD) and catalase (CAT). MT pretreatment was associated with an increase in the expression of neuronal genes downregulated by H2O2. Mechanistically, MT dramatically suppressed H2O2-induced Bcl-2 downregulation, Bax upregulation, apoptotic factor caspase-3 activation, Mitogen-activated protein kinase (MAPK) (JNK, ERK, and p38), and Nuclear factor-κB (NF-κB) activation, thereby preventing H2O2-induced neurotoxicity. These results indicate that MT has protective effects against H2O2-induced oxidative damage in SH-SY5Y cells and can be used to prevent and protect against neurodegeneration.

Aronia, blueberry, Korean raspberry, blackberry, mulberry, and red raspberry fruits cultivated in Korea were evaluated for total phenol content (TPC), total flavonoid content (TFC), total anthocyanin, and ascorbic acid content. All berries were assayed for antioxidant activities determined as 2,2-diphenyl-1-picrylhydrazyl free radical scavenging activity, 2,2’-azino-bis(3-ethylbenzothiazoline)-6 sulphonic acid free radical scavenging activity, and ferric reducing antioxidant power. Individual phenolic compounds in aronia were also identified using high-performance liquid chromatography/quadrupole-time of flight mass spectrometry. TPC, TFC, total anthocyanin, and ascorbic acid contents of the fruit samples ranged from 17.05 to 135.55 mg of gallic acid equivalent/g dry weight (dw), 1.0 to 8.59 mg of rutin equivalent/g dw, 2.55 to 24.43 mg of cyanidin-3-O-glucoside equivalent/g dw, and 3.14 to 19.45 mg of ascorbic acid equivalent/g dw, respec-tively. Aronia and Korean raspberry showed the highest TPC, TFC, and total anthocyanin while red raspberry had the high-est ascorbic acid content. Antioxidant activities showed positive correlations to phenolic and anthocyanin contents suggesting antioxidant activity of berry samples is due to these compounds. Aronia had the highest antioxidant value among fruits.

There is a growing global demand for teff ( Eragrostis tef (Zucc.) Trotter) grain due to its gluten-free nature, high level of essential amino acids, high mineral content, low glycemic index, high crude fiber content, longer shelf life, and slow staling of its bread products compared to those of wheat, sorghum, rice, barley, and maize. However, only a limited and less reliable data exists on phenolic profiles of teff grain. This article aimed at exploring phenolic contents and chemical compositions of four teff grain samples (two white and two brown) as well as their in vitro antioxidant capacity. Identification of individual bioactive compounds in white teff was also conducted using UPLC-qTOF-MS. In general, teff grain was found to have a much higher phenolic content compared to other commonly consumed grains and pseudo cereals; brown teff contained higher than the white one. Antioxidant activity was also relatively higher than other common whole flour food sources. Furthermore, combination of UPLC separation, qTOF‐MS detection and automated data processing software with scientific library using UNIFI ver. 1.8 allowed us to identify a total of 61 bioactive compounds mainly phenolic compounds and saponins in teff for the first time. The findings of this study significantly contribute to enhancing the limited data on teff phenolics.

Minor ginsenosides, such as compounds (C)-K and C-Y, possess relatively better bioactivity than those of naturally occurring major ginsenosides. Therefore, this study focused on the biotransformation of major ginsenosides into minor ginsenosides using crude β-glucosidase preparation isolated from submerged liquid culture of Fomitella fraxinea (FFEP). FFEP was prepared by ammonium sulfate (30–80%) precipitation from submerged culture of F. fraxinea. FFEP was used to prepare minor ginsenosides from protopanaxadiol (PPD)-type ginsenoside (PPDG-F) or total ginsenoside fraction (TG-F). In addition, biotransformation of major ginsenosides into minor ginsenosides as affected by reaction time and pH were investigated by TLC and HPLC analyses, and the metabolites were also identified by UPLC/negative-ESI-Q-TOF-MS analysis. FFEP biotransformed ginsenosides Rb1 and Rc into C-K via the following pathways: Rd → F2 → C-K for Rb1 and both Rd → F2→ C-K and C-Mc1 → C-Mc → C-K for Rc, respectively, while C-Y is formed from Rb2 via C-O. FFEP can be applied to produce minor ginsenosides C-K and C-Y from PPDG-F or TG-F. To the best of our knowledge, this study is the first to report the production of C-K and C-Y from major ginsenosides by basidiomycete F. fraxinea.

The ripe fruits of Maclura tricuspidata (formerly Cudrania tricuspidata) are bright red in color and are edible with a floral aroma and sweet taste. They have traditionally been used to prepare fresh juice, jam, wine, vinegar and alcoholic beverages in Korea. This study was carried out to characterize the volatile aroma components of wine and vinegar prepared from M. tricuspidata fruit by yeast (Fermivin) and Acetobacter pasterianus YJ17. Its volatile aroma components were also compared with those of six commercial vinegars (three domestic vinegars and three foreign balsamic vinegar products). Volatile compounds were separated by solid-phase extraction (SPE) using Amberlite XAD-2 as a sorbent. Fifty-seven compounds, including 15 alcohols, 15 esters, 12 aldehydes and ketones, 7 acids and 8 miscellaneous compounds were identified by gas chromatography (GC) and gas chromatography-mass spectrometry (GC-MS) analyses in the seven vinegars and the M. tricuspidata wine sample. The newly prepared M. tricuspidata fruit vinegar (MTFV) contained 47 of them. Among all the identified compounds, ethyl hydrogen succinate, phenylacetic acid, p-hydroxybenzyl alcohol, p-hydroxybenzaldehyde, p-hydroxyphenylacetic acid, tyrosol (p-hydroxyphenylethyl alcohol), dihydroactinidiolide, 3-hydroxy-β-ionone and tryptophol were only detected in the MTFV. p-Hydroxybenzyl alcohol, p-hydroxybenzaldehyde, p-hydroxyphenylacetic acid and tyrosol have been reported to have various biological activities. Therefore, their exclusive presence in the MTFV may contribute to its health benefits.

Essential oil obtained from Maclura triscuspidata fruit has been reported to have functional properties. This study aimed at determining chemical compositions and antioxidant activities of steam-distilled essential oil (SDEO) and glycosidically bound aglycone fraction (GBAF) isolated from fully ripe M. triscuspidata fruit. SDEO was isolated by simultaneous steam distillation and extraction (SDE). GBAF was prepared by Amberlite XAD-2 adsorption of methanol extract, followed by methanol elution and enzymatic hydrolysis. Both fractions were analyzed by gas chromatography-mass spectrometry (GC-MS). A total of 76 constituents were identified from both oils. Apart from fatty acids and their esters, the SDEO contained p-cresol in the highest concentration (383.5 ± 17.7), followed by δ-cadinene (147.7 ± 7.7), β-caryophyllene (145.7 ± 10.5), β-ionone (141.0 ± 4.5), n-nonanal (140.3 ± 20.5), theaspirane A (121.3 ± 4.5) and theaspirane B (99.67 ± 9.05 µg/g). Thirteen carotenoid-derived compounds identified in the SDEO are being isolated from M. triscuspidata fruit for the first time. Out of the 22 components identified in GBAF, 14 were present only in the glycosidically bound volatiles. Antioxidant activity of the GBAF was higher than that of SDEO. These results suggest that glycosidically bound volatiles of M. triscuspidata fruit have a good potential as natural antioxidants.

A thermostable extracellular tannase induced during solid state fermentation of the stem bark of Toxicodendron vernicifluum (Stokes) F.A. Barkley (Anacardiaceae) with Fomitella fraxinea was homogeneously isolated through ammonium sulfate precipitation and purified by DEAE-cellulose, and Sephadex G-100 gel chromatography. It was then characterized for optimal reaction temperature and pH, thermal and pH stability, effects of metal ions as well as its hydrolysis patterns using 1,2,3,4,6-penta-O-galloyl-beta-glucose (PGG) as a substrate. The enzyme was purified 103.9-fold with 2.92% recovery and a single protein band corresponding to it was observed at 44.9 kDa during SDS-PAGE analysis. Optimal temperature and pH were found to be 50-70 degrees C and 5.5, respectively. This enzyme was substantially stable at temperatures below 70 degrees C and pH values between 5.0 and 7.0. Its activity was inhibited by Fe2+ ion (66%) and Cu2+ (39%) at a concentration of 5 mM. It also showed a different hydrolysis pattern from that of commercial Aspergillus oryzae tannase when PGG was used as a substrate. The tannase purified from the fermented plant material in this study unusually produced oligomeric galloylglucoses such as digalloylglucose (DGG), trigalloylglucose (TGG) and tetragalloylglucose (TeGG) from PGG while the Asp. oryzae tannase produced gallic acid and methyl gallate as final products. Therefore, this enzyme can be more preferably applied for production of bioactive oligomeric galloylglucoses such as DGG, TGG and TeGG from PGG or tannic acid.

The stem bark of Toxicodendron vernicifluum (TVSB) has been widely used as a traditional herbal medicine and food ingredients in Korea. However, its application has been restricted due to its potential to cause allergies. Moreover, there is limited data available on the qualitative and quantitative changes in the composition of its phytochemicals during fermentation. Although the Formitella fraxinea-mediated fermentation method has been reported as an effective detoxification tool, changes to its bioactive components and the antioxidant activity that takes place during its fermentation process have not yet been fully elucidated. This study aimed to investigate the dynamic changes of urushiols, bioactive compounds, and antioxidant properties during the fermentation of TVSB by mushroom F. fraxinea. The contents of urushiols, total polyphenols, and individual flavonoids (fisetin, fustin, sulfuretin, and butein) and 1,2,3,4,6-penta-O-galloyl-β-D-glucose (PGG) significantly decreased during the first 10 days of fermentation, with only a slight decrease thereafter until 22 days. Free radical scavenging activities using 2,2-diphenyl-1-picrylhydrazyl (DPPH), 2,2′-azino-bis(3-ethylbenzothiazoline-6- sulfonic acid) (ABTS), and ferric reducing/antioxidant power (FRAP) as an antioxidant function also decreased significantly during the first six to nine days of fermentation followed by a gentle decrease up until 22 days. These findings can be helpful in optimizing the F. fraxinea–mediated fermentation process of TVSB and developing functional foods with reduced allergy using fermented TVSB.

Maclura tricuspidata fruit contains various bioactive compounds and has traditionally been used in folk medicine and as valuable food material in Korea. The composition and contents of bioactive compounds in the fruit can be influenced by its maturity stages. In this study, total phenol, total flavonoid, individual polyphenolic compounds, total carotenoids and antioxidant activities at four maturity stages of the fruit were determined. Polyphenolic compounds were analyzed using high-pressure liquid chromatography-quadrupole time-of-flight mass spectrometry (HPLC-QTOF-MS) and HPLC. Among 18 polyphenolic compounds identified in this study, five parishin derivatives (gastrodin, parishin A, B, C, E) were positively identified for the first time in this plant. These compounds were also validated and quantified using authentic standards. Parishin A was the most abundant component, followed by chlorogenic acid, gastrodin, eriodictyol glucoside, parishin C, parishin E and parishin B. The contents of all the polyphenolic compounds were higher at the immature and premature stages than at fully mature and overmature stages, while total carotenoid was found to be higher in the mature and overmature stages. Overall antioxidant activities by three different assays (DPPH, ABTS, FRAP) decreased as maturation progressed. Antioxidant properties of the fruit extract are suggested to be attributed to the polyphenols.