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Two pairs of new salicylaldehyde derivative enantiomers, salicylaldehydiums A and B (1 and 2), along with five known analogues were isolated and identified from a marine-derived fungus Eurotium sp. SCSIO F452. Their structures and absolute configuration were determined by extensive spectroscopic analysis and electronic circular dichroism (ECD) calculations. All the new optical pure enantiomers [(+)-1, (-)-1, (+)-2, (-)-2] were evaluated for their cytotoxic and antioxidative activities. Compound (-)-1 exhibited weak cytotoxic activity.

Averrhoa carambola L. (Oxalidaceae) was widely cultivated for fruits (star fruit), whereas the value of leaves remains to be discovered. Our study on the leaves yielded five flavan-3-ols (1-5) and two 2-diglycosyloxybenzoates. Their structures were determined by spectroscopic and chemical methods. Epicatechin-(5,6-bc)-4β-(p-hydroxyphenyl)-dihydro-2(3H)-pyranone (1) and benzyl 2-β-d-apiofuranosyl-(1 → 6)-β-d-glucopyranosyloxybenzoate (6) were new structures. 6-(S -2 -Pyrrolidinone-5-yl)epicatechin (4) and 6-(R-2-pyrrolidinone-5-yl)epicatechin (5) were obtained as monomeric diastereomer for the first time and their absolute configurations were determined by electronic circular dichroism (ECD) computation. Epicatechin-(7,8-bc)-4α-(p-hydroxyphenyl)-dihydro-2(3H)-pyranone (2), epicatechin-(7,8-bc)-4β-(p-hydroxyphenyl)-dihydro-2(3H)-pyranone (3), and methyl 2-β-d-apiofuranosyl-(1 → 6)-β-d-glucopyranosyloxybenzoate (7) were not previously reported from the genus Averrhoa. Compounds 1-5 showed more potent 2,2'-azino-bis(3-ethylbenzthiazoline-6-sulphonic acid) (ABTS) radical cation and 2,2-diphenyl-1-picrylhydrazyl (DPPH) radical scavenging activities and ferric reducing antioxidant power (FRAP) than l-ascorbic acid. Meanwhile 1 and 3 exhibited lipase and α-glucosidase inhibitory activities, respectively. The results clarified the structures of flavan-3-ols and 2-diglycosyloxybenzoates in the leaves and their antioxidant, lipase, and α-glucosidase inhibitory activities., (Copyright © 2019 Elsevier B.V. All rights reserved.)

Three new phenolic glucosides, falandiosides A (1), B (2), and C (6) were isolated from strawberry (Fragaria×ananassa Duch.) cv. Falandi fruit, together with three flavone glucuronides (3-5), eleven lignan glycosides (12-22), and five others. Their structures were determined by spectroscopic methods. All the known phenolics were reported from strawberry for the first time. They were evaluated for antioxidant and α-glucosidase inhibitory activities. Three new and fifteen known phenolics showed potent 2,2'-azinobis(3-ethylbenzthiazoline-6-sulfonic acid) (ABTS) radical cation scavenging activity with IC50 values of 22.50-4.28μM in comparison to l-ascorbic acid (14.21μM). Quercetin 3-(6-methylglucuronide) (4), (+)-isolariciresinol 9'-glucoside (12), and (-)-isolariciresinol 9'-glucoside (13) were active in scavenging 1,1-diphenyl-2-picrylhydrazyl (DPPH) radicals. Moreover, compounds 12 and 13 had moderate ferric reducing antioxidant power (FRAP) values. Further, two new and seven known phenolics exhibited more potent α-glucosidase inhibitory activity with IC50 values of 537.43-25.39μM than acarbose (619.94μM)., (Copyright © 2015 Elsevier Ltd. All rights reserved.)

An activity-directed fractionation and purification process was used to isolate antioxidant components from cassava stems produced in Hainan. The ethyl acetate and n-butanol fractions showed greater DPPH˙and ABTS·+ scavenging activities than other fractions. The ethyl acetate fraction was subjected to column chromatography, to yield ten phenolic compounds: Coniferaldehyde (1), isovanillin (2), 6-deoxyjacareubin (3), scopoletin (4), syringaldehyde (5), pinoresinol (6), p-coumaric acid (7), ficusol (8), balanophonin (9) and ethamivan (10), which possess significant antioxidant activities. The relative order of DPPH· scavenging capacity for these compounds was ascorbic acid (reference) > 6 > 1 > 8 > 10 > 9 > 3 > 4 > 7 > 5 > 2, and that of ABTS·+ scavenging capacity was 5 > 7 > 1 > 10 > 4 > 6 > 8 > 2 > Trolox (reference compound) > 3 > 9. The results showed that these phenolic compounds contributed to the antioxidant activity of cassava.

The first stilbene possessing a γ-aminobutyric acid lactam function, artocarpene (1), and a new flavanone, 2-hydroxynaringenin 4'-O-β-d-glucopyranoside (2), were isolated from the stems of Artocarpus nitidus subsp. lingnanensis along with four known compounds, 2-hydroxynaringenin (3), oxyresveratrol (4), 3,4',5-trihydroxy-3'-prenylstilbene (5) and norartocarpetin (6). Their structures were elucidated on the basis of spectroscopic data. Compounds 1 exhibited weak antioxidant activity and 2 displayed weak cytotoxicity against human lung cancer A549 cell line., (Copyright © 2011 Elsevier B.V. All rights reserved.)

Two new A-type trimeric proanthocyanidins with two doubly bonded interflavanoid linkages, litchitannin A1 [epicatechin-(2β→O→7,4β→6)-epicatechin-(2β→O→7,4β→8)-catechin] (1) and litchitannin A2 [epicatechin-(2β→O→7,4β→6)-epicatechin-(2β→O→7,4β→6)-epicatechin] (2), were isolated from lychee (Litchi chinensis Sonn. cv. Heiye) seeds together with aesculitannin A (3), epicatechin-(2β→O→7,4β→8)-epiafzelechin-(4α→8)-epicatechin (4), proanthocyanidin A1 (5), proanthocyanidin A2 (6), proanthocyanidin A6 (7), epicatechin-(7,8-bc)-4β-(4-hydroxyphenyl)-dihydro-2(3H)-pyranone (8), and epicatechin (9). Their structures were elucidated on the basis of spectroscopic and chemical evidence. It is the first time that compounds 1-4, 7, and 8 have been reported in this species. Compounds 1-9 showed more potent antioxidant activity than L-ascorbic acid with ferric reducing antioxidant power (FRAP) values of 3.71-24.18 mmol/g and IC50 values of 5.25-20.07 μM toward DPPH radicals. Moreover, litchitannin A2 (2) was found to exhibit in vitro antiviral activity against coxsackie virus B3 (CVB3) and compounds 3 and 6 displayed antiherpes simplex virus 1 (HSV-1) activity.

Two 2-phenylbenzofurans, lespedezavirgatol (1) and lespedezavirgatal (2), and a coumestan, lespedezacoumestan (3), were isolated from the aerial parts of Lespedeza virgata, together with nine known flavonoids. Their structures were determined on the basis of spectroscopic data. The three new compounds showed strong oxygen radical absorbance capacity and potent inhibition toward lipid peroxidation in both plasma and kidney homogenate of renal failure rats.

Longan fruits contain a significant amount of polyphenols. In the present study, polyphenols were extracted from longan pericarp tissues, and then two representative polyphenols were separated and purified by polyamide column chromatography, Sephadex LH-20 column chromatography, and silica gel column chromatography. On the basis of 1H NMR, 13C NMR, and electrospray ionization mass spectrometric (ESI-MS) data, the two compounds were identified as 4-O-methylgallic acid and (-)-epicatechin, respectively. In terms of reaction with longan polyphenol oxidase (PPO), (-)-epicatechin was further identified as the PPO substrate that caused longan fruit to brown. The results of antioxidant activity showed that 4-O-methylgallic acid had higher reducing power and 2,2-diphenyl-1-picrylhydrazyl- (DPPH-), hydroxyl radical-, and superoxide radical-scavenging activities than (-)-epicatechin.

Chinese water chestnut (CWC) is one of the most popular foods among Asian people due to its special taste and medical function. Experiments were conducted to test the antioxidant activity and then determine the major phenolic compound components present in CWC. CWC phenolic extract strongly inhibited linoleic acid oxidation and exhibited a dose-dependent free-radical scavenging activity against alpha,alpha-diphenyl-beta-picrylhydrazyl (DPPH) radicals, superoxide anions and hydroxyl radicals, which was superior to ascorbic acid and butylated hydroxytoluene (BHT), two commercial used antioxidants. Furthermore, the CWC extract was found to have a relatively higher reducing power, compared with BHT. The major phenolic compounds present in CWC tissues were extracted, purified and identified by high-performance liquid chromatograph (HPLC) as (-)-gallocatechin gallate, (-)-epicatechin gallate and (+)-catechin gallate. This study suggests that CWC tissues exhibit great potential for antioxidant activity and may be useful for their nutritional and medicinal functions.

Objective. This study aimed to observe the regulatory effects of astragaloside IV (AS-IV) on hyperglycemia-induced mitochondrial damage and mitophagy in Schwann cells and to provide references for clinical trials on AS-IV in the treatment of diabetic peripheral neuropathy. Methods. Schwann cells were grown in a high-glucose medium to construct an autophagy model; the cells were then treated with AS-IV and N-acetylcysteine (control) to observe the regulatory effects of AS-IV on oxidative stress and mitophagy. Results. AS-IV exhibited antioxidant activity and inhibited the overactivation of autophagy in Schwann cells, significantly reducing the level of reactive oxygen species and downregulating the expression of autophagy-related proteins (LC3, PINK, and Parkin) under hyperglycemic conditions, thereby exerting a protective effect on mitochondrial morphology and membrane potential. Conclusion. AS-IV can maintain the mitochondrial function of Schwann cells under hyperglycemic conditions by effectively alleviating oxidative stress and overactivation of mitophagy. The evidence from this study supports an AS-IV-based therapeutic strategy against diabetic peripheral neuropathy. [ABSTRACT FROM AUTHOR]

In order to improve the bioactivities of the polysaccharide from Enteromorpha prolifera (PE), crude PE (Mw 1400 kDa) was degraded to low molecular weight polysaccharide (44 kDa) in the presence of hydrogen peroxide/ascorbic acid, followed by carboxymethylation. The reaction conditions for carboxymethylation of degraded polysaccharide (DPE) were optimized by Response Surface Methodology. The carboxymethyled degraded polysaccharide (CDPE) obtained under optimized conditions, with a degree of carboxymethylation of 0.849, was characterized by FT-IR and 13 C NMR. The molecular weight of CDPE was measured to be 53.7 kDa. CDPE was evaluated for its antioxidant activity by determining the ability to scavenge 1,1-diphenyl-2-picrylhydrazyl (DPPH), hydroxyl and superoxide anion radicals, and by determining the ferric reducing power. The antioxidant activity of CDPE was found to be greatly improved in comparison with degraded polysaccharide (DPE) and crude polysaccharide from Enteromorpha prolifera (PE). [ABSTRACT FROM AUTHOR]

The fruit of Clausena lansium (wampee) is popular in southern China and warm areas of the world. Our chemical study on the fruit yielded three jasmonoid glucosides, 12-β- d -glucopyranosyloxy-6- epi -7-isocucurbic acid-1,6-lactone ( 1 ), 12-β- d -glucopyranosyloxyjasmonic acid ( 2 ) and 12-hydroxyjasmonic acid ( 3 ), two sesquiterpenes, (+)-curcumen-12-oic acid ( 4 ) and (+)-( E )-α-santalen-12-oic acid ( 5 ), two coumarins, xanthotoxol ( 6 ) and indicolactone ( 7 ), in addition to 3,4-dihydroxybenzoic acid ( 8 ), 5-hydroxymethylfuraldehyde ( 9 ), isopropyl β- d -glucopyranoside ( 10 ) and stigmasterol ( 11 ). Their structures were determined by spectroscopic methods. Compound 1 was a new metabolite and the others excluding 6 were reported from the species for the first time. Compounds 1 – 7 were evaluated for antioxidant and antibacterial activities. Among them, compound 6 showed antioxidant activity in ferric reducing antioxidant power (FRAP) and DPPH radical scavenging assays as well as antibacterial activity against Staphyloccocus aureus and Shigella dysenteriae , while compound 5 was active against Bacillus cereus . [ABSTRACT FROM AUTHOR]

Abstract: 3,12-Dihydroxy-cis-3,4-methylenedodecanoic acid 3-O-β-d-glucopyranoside, trivially named litchioside C (1), the first cyclopropyl-containing fatty acid glycoside, was isolated along with three previously uncharacterized galactosylacylglycerols from the seeds of Litchi chinensis. Its structure was established on the basis of spectroscopic analysis including HRESIMS and 2D NMR spectra. Its antioxidant and antibacterial activities were evaluated and its biogenetic pathway was discussed. [Copyright &y& Elsevier]

Abstract: The experiments were performed to extract and purify substrates for polyphenol oxidase (PPO) from pericarp tissue of postharvest litchi fruit. Two purified PPO substrates were identified as (−)-epicatechin and procyanidin A2. The antioxidant properties of two PPO substrates were further evaluated in the present study. Variation in the content of the major substrate (−)-epicatechin of litchi fruit during storage at 25°C was analysed using the HPLC-UV method. The results showed that (−)-epicatechin exhibited stronger antioxidant capability than procyanidin A2, in terms of reducing power and scavenging activities of DPPH radical, hydroxyl radical and superoxide radical. Furthermore, (−)-epicatechin content in pericarp tissue tended to decrease with increasing skin browning index of litchi fruit during storage at 25°C. Thus, these two compounds can be used as potential antioxidants in litchi waste and the fresh pericarp tissue of litchi fruit exhibited a better utilisation value. [Copyright &y& Elsevier]

Abstract: Fruits of wampee [Clausena lansium (Lour.) Skeels] contain a significant amount of coumarins with many health benefits. The activity-guided separation of an ethyl acetate-soluble fraction on a polyamide column followed by silica gel column and high performance liquid chromatography (HPLC) preparation afforded a pure compound, which was identified to be 8-hydroxypsoralen based on the 1H, 13C NMR (nuclear magnetic resonance), and ESI-MS (electrospray ionisation mass spectrometric) analysis. This isolate exhibited good scavenging activities against DPPH radical and superoxide anion as well as significant reducing power. It also showed potent proliferation inhibitory activity against human hepatocellular liver carcinoma cell line (HepG2), human lung adenocarcinoma epithelial cell line (A549) and human cervical carcinoma cell line (HELA). This is the first report on the antioxidant and cytotoxic properties of C. lansium fruit extract. The food and pharmaceutical industry could be benefited by the usage of this extract containing this constituent. [Copyright &y& Elsevier]

Abstract: Longan fruit pericarp was extracted with 50% ethanol employing high pressure (500 MPa) and conventional extraction methods. Total phenolic contents of high pressure-assisted extract of longan (HPEL) and conventional extract of longan (CEL) were 20.8 and 14.6 mg gallic acid equivalents/g dry weight, respectively. Subsequently, the antioxidant activities of these extracts were analyzed employing various antioxidant model systems including 1,1-diphenyl-2-picrylhydrazyl (DPPH) radical scavenging activity, superoxide anion radical scavenging activity, total antioxidant capacity, and lipid peroxidation inhibitory activity. In addition, anticancer activity was also tested using HepG2, A549, and SGC 7901 cancer cell lines. HPEL showed excellent antioxidant and anticancer activities and were higher than CEL. Three phenolic compounds, namely gallic acid, corilagin, and ellagic acid, were identified and quantified by external standard methods. Compared with CEL, HPEL exhibited higher extraction effectiveness in terms of higher extraction yield, higher phenolic content, and higher antioxidant and anticancer activity with shorter extraction time. Industrial relevance: This study was focused to evaluate the antioxidant and anticancer activity of longan fruit pericarp by high-pressure treatment. The high-pressure treatment provided a better way of utilizing longan fruit pericarp as a readily accessible source of the natural anticancer and antioxidant in food and pharmaceutical industry. [Copyright &y& Elsevier]

Abstract: Five previously uncharacterised polyphenols, ethyl gallate (2), 1-β-O-galloyl-d-glucopyranose (3), methyl brevifolin carboxylate (4), brevifolin (5) and 4-O-α-l-rhamnopyranosyl-ellagic acid (8), and three previously identified polyphenols, gallic acid (1), corilagin (6) and ellagic acid (7), were isolated from longan seeds. Their structures were identified by spectroscopic and chemical methods including HRESIMS and NMR. Eight polyphenols exhibited scavenging activity towards DPPH radicals with SC50 values of 0.80–5.91μg/ml and towards superoxide radicals with SC50 values of 1.04–7.03μg/ml. The radical-scavenging activity of the newly characterised polyphenols was comparable to that of gallic acid, corilagin and ellagic acid. [Copyright &y& Elsevier]

Abstract: Iridoid glycosides, 2′,3′,6′-tri-O-acetyl-4′-O-trans-p-(O-β-d-glucopyranosyl)coumaroyl-7-ketologanin (1), 2′-O-caffeoylloganic acid (2), 2′-O-p-hydroxybenzoylloganic acid (3), 2′-O-trans-p-coumaroylloganic acid (4), and 2′-O-cis-p-coumaroylloganic acid (5), were isolated from whole plants of Gentiana loureirii along with six known iridoids, 7-ketologanin (6), loganin (7), loganic acid (8), sweroside, boonein, and isoboonein, and three other known compounds. Their structures were elucidated by spectroscopic means and chemical correlations. The isolated iridoids were evaluated for antibacterial and antioxidant activities, but were either inactive or very weakly active. [Copyright &y& Elsevier]