To develop the potential applications of Plantago plants, seed oils were extracted from 14 cultivars of Plantago around China. Their fatty acid profiles, tocopherols, carotenoid compositions, anti-inflammatory and antioxidant properties were also investigated. The Plantago seed oils (PSO) were abundant in linolenic acid from 11.12 to 29.36 g/100 g oil and had low fatty acid ratio of n-6/n-3 ratio matched with the dietary recommendations. The tocopherol contents of PSO ranged from 693.25 to 3708.80 μg/g and the lutein contents ranged from 2.29 to 26.68 μg/g. The PSO showed significant inhibitory effects on TNF-α, IL-1β, and COX-2 mRNA expression in RAW 264.7 mouse macrophage cells induced by LPS. In addition, the properties on scavenging DPPH, oxygen and hydroxyl radicals indicated that PSO had potential antioxidant properties. The results could develop PSO as novel functional foods to improve human health.

A new heteropolysaccharide (PMH) with a molecular weight of 1.4 × 103 kDa was isolated from the seed husks of Plantago asiatica L. The monosaccharide composition of PMH was determined as glucose, xylose, arabinose, rhamnose, galactose and galacturonic acid with a molar ratio of 1.0 : 1.8 : 2.4 : 3.8 : 4.9 : 8.5. The backbone of PMH consisted of 1,4-β-D-GalpA with the side chains mainly composed of 1,3-α-D-Galp and 1,2-α-D-Galp which were attached to the O-3 of GlapA. The thermal analysis using the Flynn–Wall–Ozawa (FWO) method revealed that PMH had an apparent activation energy (Ea) of 173.1 kJ mol−1. PMH experienced a major decomposition during the heating process at a temperature of 91.1 °C with a dry weight loss of 31.1%. Moreover, PMH exhibited stronger antioxidant ability than commercial psyllium, partially due to its higher content of uronic acid. The results suggested that PMH could be used in functional foods due to its structural, thermal and antioxidant characteristics.

•The content of SDF from black bean coats increased by AHP modification.•M-SDF had different monosaccharide ratio and lower ζ-potential than O-SDF.•M-SDF had stronger gelation ability at the presence of Ca2+ than O-SDF.•Good bile acid binding capacity was observed in M-SDF.Alkaline hydrogen peroxide (AHP) was investigated to enhance the content and functionality of soluble dietary fiber (SDF) extracted from black bean coats. Compared with the content of SDF of original black bean coats 7.8%, the content of SDF of modified black bean coats was 16.9% after treated by 15% H2O2 (v/v) at pH 11 and 1:18 (w/v) as liquid-to-solid ratio for 0.5 h. Monosaccharide composition confirmed that the ratio of galacturonic acid in modified SDF (M-SDF) was higher than that of original SDF (O-SDF), and M-SDF was also with smaller molecular weight (Mw) of 1.24 × 106 Da and lower ζ-potential of −42.3 mV. Other structural characters were determined by FT-IR and TEM. In the range of 2–6% (w/v), both O-SDF and M-SDF showed a shear thinning behavior. The latter showed stronger gelation ability at the presence of Ca2+ evaluated by dynamic oscillatory rheometry. Moreover, M-SDF exhibited good abilities of binding bile acids in vitro. It could be concluded that M-SDF had a great potential to be applied as a novel kind of functional ingredient or additive in food industry.Download high-res image (212KB)Download full-size image

•Four pairs of dihydroflavonol glycoside diastereomers were firstly purified by HPCCC.•Their chemical structures were identified by HR-ESIMS, 1H-, 13C-NMR and CD spectra.•HPCCC with HP-β-CD showed a promising application in the isolation of diastereomers.Four pairs of diastereomers were successfully isolated and separated from the water extract of Engelhardia roxburghiana by high performance counter-current chromatography (HPCCC) using a two-step procedure. The diastereomers were initially separated by a two-phase solvent system composed of n-hexane–n-butanol–0.1% trifluoroacetic acid (1:2:3, v/v/v) and followed by the same solvent system using hydroxypropyl-β-cyclodextrin (HP-β-CD) as an additive. The chromatographic conditions, elution mode, and concentrations of the additive were refined. The two-step HPCCC isolation yielded 43.7 mg (2S, 3S)-astilbin, 27.6 mg (2R, 3R)-astilbin, 5.9 mg (2S, 3R)-astilbin, 4.8 mg (2R, 3S)-astilbin, 6.9 mg (2S, 3S)-engelitin, 3.1 mg (2R, 3R)-engelitin, 8.2 mg (2S, 3R)-engelitin, and 6.0 mg (2R, 3S)-engelitin from 384 mg crude extract in four runs with purities of 99.3%, 96.2%, 99.8%, 99.9%, 97.0%, 96.5%, 96.1%, and 96.8%, respectively. The present study revealed that HP-β-CD can be used as an additive in HPCCC to effectively improve the resolution of the diastereomers. The established HPCCC method may serve as an approach to obtain high purity diastereomers on a large scale.

A new acidic polysaccharide (PLP) was isolated and characterized from Plantago asiatic L. seeds by hot alkali extraction and chromatographic purification using DEAE cellulose and Sephacryl S-400 columns. PLP has a molecular weight of 1.15 × 106 Da, and a monosaccharide composition of xylose (Xyl), arabinose (Ara), glucuronic acid (GlcA), and galactose (Gal) in a molar ratio of 18.8:7.2:6.1:1. The results of methylation analysis, FT-IR, and 1D and 2D NMR indicated that PLP was a highly branched heteroxylan of β-1,4-linked Xylp backbone with three α-GlcAp-(1→3)-Araf attached to the O-3 position and one α-T-linked-GlcAp and one α-Araf-(1→5)-Araf attached to the O-2 position every eight monosaccharide residues. PLP exhibited scavenging abilities against hydroxyl, peroxyl anion, and DPPH radicals in vitro and showed significant binding capacities against cholic and chenodeoxycholic acids, suggesting its possible cholesterol-lowering activity. The results demonstrated the potential use of PLP in functional foods and nutraceuticals.

A novel polysaccharide (GPP-S), with a molecular mass of 1.2 × 106 Da, was isolated from the tetraploid Gynostemma pentaphyllum Makino by alkali extraction followed by purifications using DEAE and Sephacryl S-400 column chromatographies. The monosaccharide composition of GPP-S was determined as rhamnose, arabinose, glucose, and galactose with a molar ratio of 1.00:3.72:19.49:7.82. The structural analysis suggested that the backbone of GPP-S is (1→4)-linked-glucose and (1→6)-linked-galactose with a (1→4,6)-linked-glucose branch every six monosaccharide residues. The terminals were 1-)-α-arabinose, glucuronic acid, and other monosaccharides. GPP-S exhibited scavenging capacities against hydroxyl, peroxyl, and DPPH• radicals in vitro. GPP-S also had inhibitory activities on IL-1β, IL-6, and COX-2 gene expressions in RAW 264.7 mouse macrophage cells. These results suggested that GPP-S could be developed as a bioactive ingredient for functional foods and dietary supplements.

A novel microbial transglutaminase-catalyzed aqueous–organic biphasic reaction system was successfully developed to prepare caseinate derivatives by cross-linking and incorporating nonpolar octyl tails for the first time. SDS-PAGE and 1H NMR analysis confirmed that cross-linking and octyl conjugation occurred simultaneously. The octyl substitution degree (SD) was measured by 1H NMR and used as an index to determine a suitable reaction condition. It was found that at the condition of 0.125% (w/v) protein concentration and 6 h of reaction time, the modified caseinate had the highest SD of 28.96%. The modified caseinate also had an increased surface hydrophobicity, better emulsifying activity, and improved thermal and salt stabilities. However, its emulsion stability or in vitro enzymatic digestibility was slightly lower than that of the native caseinate.

The effects of sulfation, hydroxypropylation, and succinylation on gelling, water uptake, swelling, and bile acid-binding capacities of psyllium were examined and compared at the same molar substitution degree. Sulfated, hydroxypropylated, and succinylated psyllium were prepared with substitution levels of 1.02, 0.88, and 0.79, respectively, and their structures were characterized using FT-IR, SEM, and ζ-potential determination. All three derivatization methods reduced the gelling and swelling capacities of psyllium and increased the water uptake and bile acid-binding capacities compared to the original psyllium. Interestingly, it was observed for the first time that introduction of a stronger negatively charged group into the molecule might more effectively enhance the bile acid-binding capacity of psyllium. On the other hand, the steric effect of the substitution groups seemed to be more critical in altering the gelling and swelling properties of psyllium.