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Twelve chemical constituents were identified from the Agriophyllum squarrosum seed (ASS). ASS contained large amounts of flavonoids, which were more concentrated in the seed coat. ASS-coat (1 g) contained 335.7 μg flavonoids of rutin equivalent, which was similar to the flavonoid content in soybean (351.2 μg/g), and greater than that in millet, wheat, rice, peanut, and corn. By LC-MS analysis, the major constituents in ASS were 3-O-[α-L-rhamnopyranosyl-(1→6)-β-D- glucopyranosyl]-7- O-(β-D-glucopyranosyl)-quercetin (1), rutin (4), quercetin-3-O-β-D- apiosyl(1→2)-[α-L-rhamnosyl(l→6)]-β-D-glucoside (2), isorhamnetin-3-O-rutinoside (5), and allantoin (3), compared with isoflavonoids-genistin (16), daidzin (14), and glycitin (18) in soybean. Among constituents in ASS, compounds 1, 2, 4, protocatechuic acid (8), isoquercitrin (11), and luteolin-6-C-glucoside (12) potently scavenged DPPH radicals and intracellular ROS; strongly protected against peroxyl radical-induced DNA scission; and upregulated Nrf2, phosphorylated p38, phosphorylated JNK, and Bcl-2 in HepG2 cells. These results indicate that ASS is rich in antioxidant constituents that can enrich the varieties of food flavonoids, with significant beneficial implications for those who suffer from oxidative stress-related conditions., Practical Application: This study found that A. squarrosum seed contains large amounts of antioxidative flavonoids and compared its chemical constituents with those of conventional foods. These results should increase the interest in planting the sand-fixing A. squarrosum on a large scale, thus preventing desertification and providing valuable foods., (© 2018 Institute of Food Technologists®.)

Chlorogenic acid is a well known natural product with important bioactivities. It contains an ester bond formed between the COOH of caffeic acid and the 3-OH of quinic acid. We synthesized a chlorogenic acid analogue, 3α-caffeoylquinic acid amide, using caffeic and quinic acids as starting materials. The caffeoylquinc acid amide was found to be much more stable than chlorogenic acid and showed anti-Hepatitis C virus (anti-HCV) activity with a potency similar to chlorogenic acid. The caffeoylquinc acid amide potently protected HepG2 cells against oxidative stress induced by tert-butyl hydroperoxide.

The present study was designed to investigate the bioactive constituents of Xanthoceras sorbifolia in terms of amounts and their antioxidant, DNA scission protection, and α-glucosidase inhibitory activities. Simultaneous quantification of 10 X. sorbifolia constituents was carried out by a newly established ultra-high performance liquid chromatography-quadrupole mass spectrometry method (UHPLC-MS). The antioxidant activities were evaluated by measuring DPPH radical scavenging and DNA scission protective activities. The α-glucosidase inhibitory activities were investigated by using an assay with α-glucosidase from Bacillus Stearothermophilus and disaccharidases from mouse intestine. We found that the wood of X. sorbifolia was rich in phenolic compounds with the contents of catechin, epicatechin, myricetin, and dihydromyricetin being 0.12-0.19, 1.94-2.16, 0.77-0.91, and 6.76-7.89 mg·g(-1), respectively. The four constituents strongly scavenged DPPH radicals (with EC50 being 4.2, 3.8 and 5.7 μg·mL(-1), respectively) and remarkably protected peroxyl radical-induced DNA strand scission (92.10%, 94.66%, 75.44% and 89.95% of protection, respectively, at a concentration of 10 μmol·L(-1)). A dimeric flavan 3-ol, epigallocatechin-(4β→8, 2β→O-7)-epicatechin potently inhibited α-glucosidase with an IC50 value being as low as 1.2 μg·mL(-1). The established UHPLC-MS method could serve as a quality control tool for X. sorbifolia. In conclusion, the high contents of antioxidant and α-glucosidase inhibitory constituents in X. sorbifolia support its use as complementation of other therapeutic agents for metabolic disorders, such as diabetes and hypertension., (Copyright © 2015 China Pharmaceutical University. Published by Elsevier B.V. All rights reserved.)

Flavan-3-ol derivatives, including 3 cysteine conjugates and 3 acetylcysteine conjugates, were prepared using Cynomorium songaricum and edible reagents. The structures were determined, based on NMR and MS spectra. All compounds had stronger radical-scavenging activity than catechin and epicatechin. Moreover, the cysteine conjugates were active against α-glucosidase, whereas catechin and epicatechin were not. Two acetylcysteine flavan-3-ol conjugates, 4β-(L-acetylcysteinyl)-epicatechin 3-O-gallate and 4β-(L-acetylcysteinyl)-epiafzelechin, are novel compounds with better logP values than their cysteine counterparts. These conjugates can be prepared from purified flavan-3-ol polymers or directly from herbal material., (Copyright © 2013 Elsevier Ltd. All rights reserved.)

Unlabelled: The apple-shaped pear, the fruit of the Pyrus pyrifolia cv. pingguoli (Rosaceae) tree, is one of the most popular fruits in the northern part of China. The current study is the 1st report of its bioactive components. We identified 10 metabolites from the peels (exocarp) of apple-shaped pear and assessed their toxicity. We then compared the anti-oxidant activity, amount of total phenolic compounds, and total condensed tannin content of the peels and flesh (mesocarp) of apple-shaped pear. The 6 major components in the peels and flesh of this fruit were quantified with Ultra Performance Liquid Chromatography-Electrospray Ionization Mass Spectrometry. Results revealed that the peels possessed stronger anti-oxidant activity and contained larger amounts of phenolic compounds than the flesh. These results provide insights into the potential health benefits of this fruit and support the use of the fruit peels and products containing peels or peel components., Practical Application: The present research provided evidences that the pulp and peel waste from the juice industry of apple-shaped pear may be a source of useful compounds., (© 2012 Institute of Food Technologists®)

Background: This study aimed to investigate the antioxidant and hypolipidaemic activities of an ethanol extract of Lethariella cladonioides (Nyl.) Krog (EE) and to characterise its chemical constituents., Results: Nine phenols were identified as canarione, thamnolic acid, squamatic acid, vermicularin, norstictic acid, baeomycesis acid, lecanoric acid, barbatinic acid and usnic acid from analysis of EE by using high-performance liquid chromatography with a diode array detector-mass spectrometry. In antioxidant analysis in vitro, the highest scavenging rate of EEs on the 2,2'-azinobis-(3-ethylbenzothiazoline-6-sulfonic acid) (ABTS) radicals, superoxide anion, hydroxyl radicals and hydrogen peroxide was 81.55 ± 1.95%, 81.84 ± 4.00%, 74.28 ± 3.71% and 74.28 ± 3.71%, respectively. Meanwhile, after administration of EE for 6 weeks in high fat/cholesterol diet mice, the most significant reduction in levels of serum triglyceride, serum total cholesterol, serum low density lipoprotein cholesterol and liver malondialdehyde were 24%, 20%, 15% and 35%, respectively. The most significant increase in levels of serum high density lipoprotein cholesterol and liver superoxide dismutase was 35% and 88%, respectively., Conclusion: L. cladonioides possesses strong antioxidant and hypolipidaemic activities., (Copyright © 2011 Society of Chemical Industry.)

Two neuropective compounds were isolated from the rhizomes of Abacopteris penangiana, one was a new flavone and the other was a flavanone. Both compounds were firstly separated from natural plant. The isolation work was guided by the antioxidant activity. Both the compounds showed a significant antioxidant activity in vitro and a protective effect on dopamine-induced neurotoxicity in PC12 cells.

In our continued research on chlorogenic acid analogues and derivatives with improved bioactivity, we have synthesized some caffeoyl 5,6-anhydroquinic acid derivatives. The 1,7 acetonides of chlorogenic acid (15), and of the mono-caffeoyl 5,6-anhydroquinic acids (7-8) showed appreciable anti-HIV activity. The 3,4-dicaffeoyl 5,6-anhydroquinic acid (12) exhibited an anti-HIV activity twice as that of 3,5-dicaffeoylquinic acid (22). The caffeoyl 5,6-anhydroquinic acid derivatives displayed potent anti-oxidant activities. The mono-caffeoyl 5,6-anhydroquinic acids (10-11) were more than twice stronger than chlorogenic acid (21) on SOD-like activity., (Copyright 2009 Elsevier Ltd. All rights reserved.)

Abstract: The water soluble green tea polyphenol epigallocatechin gallate (EGCG) was lipophilised by esterification with different fatty acids for expanded applications. Four lipophilic ester derivatives of EGCG, namely EGCG-O-tetrastearate, EGCG-O-tetraeicosapentaenoate, EGCG-O-tetradocosahexaenoate, and EGCG-O-octabutyrate, were prepared and evaluated for their antioxidant and antiviral activities in vitro. Incorporation of fatty acids, especially the long chain polyunsaturated fatty acids (PUFA), into EGCG resulted in increased peroxyl radical scavenging activity, as measured by ORAC (oxygen radical absorbance capacity) assay, and metal chelation capacity. However, the esters exhibited decreased reducing power. Antiviral activities of EGCG derivatives were remarkably higher than the parent EGCG molecule, which showed relatively weak effects. The EGCG–PUFA esters were 1700-fold more effective in inhibiting hepatitis C virus (HCV) protease than the positive control embelin. The derivatives also acted as α-glucosidase inhibitors, suggesting their potential in anti-HIV (human immunodeficiency virus) treatment. The results suggest that ester derivatives of EGCG with improved bioactivities may serve as excellent functional food ingredients and natural health products. Moreover, the omega-3 PUFA in the derivatives may also render additional or synergistic health benefits. [Copyright &y& Elsevier]

Abstract: Flavan-3-ol oligomers from the stems of Cynomorium songaricum were found to show potent SOD-like activity with one of the dimers being most potent. The flavan-3-ols also showed inhibitory activity on α-glucosidase, implying the beneficial effects of this herb on diabetes patients. The total (extractable and non-extractable) tannin content of this herb was found to be as high as 18.3%. The contents of catechin, flavan-3-ol oligomers and extractable tannins using 70% acetone, methanol or water were analysed. It was found that 70% acetone was the most efficient extract solvent amongst these three solvents, especially for higher flavan-3-ol oligomers. [Copyright &y& Elsevier]

Abstract: Parathelypteriside (PG), a stilbenoid compound, was extracted from Parathelypteris glanduligera (kze.) ching that exhibits antioxidative and anti-inflammatory effects. The aim of this study was to investigate the protective effect of PG against the d-galactose (d-gal)-induced neurotoxicity in mice. It was found that long-term intraperitoneal (i.p.) injection of PG (5 or 10mg/(kgday)) for two weeks significantly improved the behavioral performance of d-gal-treated mice in both Morris water maze test and step-down avoidance test. Biochemical examination revealed that PG reduced the increased levels of malondialdehyde (MDA), and attenuated the decreased activities of superoxide dismutase (SOD), glutathione peroxidase (GPx) and catalase in the hippocampus of d-gal-treated mice. Furthermore, the electrophysiological assay showed that PG significantly rescued the long-term potentiation (LTP) impairment in mice hippocampus, and western blotting analysis indicated that the effects of PG on LTP might be attributed to the activation of cAMP-response element-binding protein (CREB). Together, these results suggested that the natural product PG represented a potential source of medicine for the treatment of the neurodegenerative diseases. [ABSTRACT FROM AUTHOR]