scholarly journals Antioxidant Phenylpropanoid Glycosides from Ginkgo biloba Fruit and Identification of a New Phenylpropanoid Glycoside, Ginkgopanoside

Plants ◽  
2021 ◽  
Vol 10 (12) ◽  
pp. 2702
Author(s):  
Akida Alishir ◽  
Ki Hyun Kim

Ginkgo biloba (Ginkgoaceae), well-known as the oldest living plant species and often referred to as a “living fossil,” is a famous medicinal plant that has been used in multiple countries to improve numerous illnesses, including anxiety, dementia, peripheral artery disease, and eye problems. We conducted a phytochemical exploration of G. biloba fruit, commonly consumed as a functional food as part of an ongoing natural product chemical research for the discovery of bioactive phytochemicals with novel structures. The natural product chemical analysis of the methanol extract of G. biloba fruit using column chromatography and high-performance liquid chromatography separation under the guidance of a liquid chromatography–mass spectrometry (LC/MS)-based analysis identified six phenylpropanoid glycosides (1–6), including one new compound, ginkgopanoside (1). The structures of the isolated compounds were elucidated by nuclear magnetic resonance spectroscopic data and LC/MS analysis, and the absolute configuration of compound 1 was established by chemical reactions followed by the application of Snatzke’s method. The 2,2-diphenyl-1-picrylhydrazyl (DPPH) scavenging activities of the isolated compounds 1–6 and the aglycone 1a of 1 were evaluated, and we found that compounds 1–5 exhibited antioxidant activities with IC50 values in the range 32.75–48.20 μM, while the aglycone 1a exhibited greater radical scavenging activity (IC50 = 5.23 μM) comparable to that of ascorbic acid (IC50 = 2.54 μM), a positive control, implying that the present of glucose may decrease the DPPH scavenging activity. These findings provide experimental information that the active phenylpropanoid glycosides could represent natural antioxidants for use in pharmaceuticals and functional foods.

PeerJ ◽  
2018 ◽  
Vol 6 ◽  
pp. e5331 ◽  
Author(s):  
Sok Sian Liew ◽  
Wan Yong Ho ◽  
Swee Keong Yeap ◽  
Shaiful Adzni Bin Sharifudin

Background Citrus sinensis peels are usually discarded as wastes; however, they are rich sources of Vitamin C, fibre, and many nutrients, including phenolics and flavonoids which are also good antioxidant agents. This study aimed to examine phytochemical composition and antioxidant capabilities of C. sinensis peel extracted conventionally with different methanol/water, ethanol/water, and acetone/water solvents. Methods C. sinensis peels were subjected to extraction with 100%, 70% and 50% of methanol, ethanol, and acetone, respectively, as well as hot water extraction. Antioxidant activities of the peel extracts were examined via the 2,2-diphenylpicrylhydrazyl (DPPH) free radical scavenging activity, ferric reducing antioxidant power (FRAP) assay, and oxygen radical absorbance capacity (ORAC) assay. Total phenolic content and total flavonoid content of the extracts were measured via the Folin-Ciocalteau method and the aluminium chloride colorimetric method, respectively. Phenolic acid and organic acid composition of the peel extracts were further determined via high performance liquid chromatography (HPLC) while flavonoid content was identified via ultra performance liquid chromatography (UPLC). Results DPPH radical scavenging activity of C. sinensis peel extracts varied from 8.35 to 18.20 mg TE/g, FRAP ranged from 95.00 to 296.61 mmol Fe(II)/g, while ORAC value ranged from 0.31 to 0.92 mol TE/g. Significant level of association between the assays was observed especially between TPC and FRAP (R-square = 0.95, P < 0.0001). TPC of various C. sinensis peel extracts ranged from 12.08 to 38.24 mg GAE/g, with 70% acetone/water extract (AEC) showing the highest TPC. TFC ranged from 1.90 to 5.51 mg CE/g. Extraction yield ranged from 0.33 to 0.54 g/g DW and tended to increase with increasing water concentration in the solvent. In the phytochemical investigation, five phenolic acids were identified using HPLC, including gallic acid, protocatechuic acid, 4-hydroxybenzoic acid, caffeic acid and ferulic acid. A total of five organic acids including lactic acid, citric acid, L-mallic acid, kojic acid and ascorbic acid were quantified via HPLC. In addition, concentrations of six flavonoids including catechin, epigallocatechin, vitexin, rutin, luteolin and apigenin were determined via UPLC. Discussion and Conclusion Phytochemicals including phenolics and flavonoids in C. sinensis peel extracts exhibited good antioxidant properties. Among the extracts, 70% AEC with highest TPC and high TFC content showed greatest antioxidant activity in all three assays. Different phenolic acids, organic acids and flavonoids were also identified from the extracts. This study indicated that C. sinensis peels contained potential antioxidant compounds which could be exploited as value added products in the food industry.


Author(s):  
Bing Zhou ◽  
Zhao Jin ◽  
Paul B. Schwarz ◽  
Yin Li

AbstractIn the present study, the objective was to evaluate the effects of barley kernel size, grind level, and extract solvent on the antioxidant activities associated with total phenolic content and phenolic acid compositions. Three barley varieties (Kindred, Azure, and Tradition), were used and the results showed that with the exception of superoxide anion radical scavenging activity, thin kernel size fraction (2.0 mm) showed much higher antioxidant activities and total phenolic content than those in the 2.4 mm and 2.8 mm fractions when averaged across barley cultivar, grind level, and extract solvent. A similar trend was found for individual phenolic acid compositions among kernel sizes. Simple correlation analysis revealed that total phenolic content showed strong correlation with DPPH· scavenging activity, ABTS + scavenging activity, and reducing power. Generally, fine grind and 80% acetone extract showed averaged highest values in antioxidant activities, total phenolic content, and individual phenolic acid compositions. Stepwise linear regression showed that extract solvent was the most important factor for DPPH· scavenging activity, ABTS + scavenging activity, reducing power, and iron chelating activity. The sum of syringic acid and caffeic acid exhibited a dominant role in explaining the major variation in antioxidant activities except for superoxide anion radical scavenging activity.


2017 ◽  
Vol 2017 ◽  
pp. 1-8 ◽  
Author(s):  
Varinder Sidhu ◽  
Dilip Nandwani ◽  
Li Wang ◽  
Ying Wu

The objective of the present study is to investigate nutritional and antioxidant activity of four types of organic tomato cultivars. The differences in tomato quality are also tested between groups with or without treatment using an organic biostimulator, Stimplex. Total phenolic compounds (TPC), lycopene,β-carotene, DPPH free radical scavenging activity, reducing power, and color parameters were investigated in the current study. The results showed that there was no significant difference in TPC among cultivars regardless of Stimplex treatment. Higher lycopene andβ-carotene were obtained in Stimplex treated tomatoes. Lycopene andβ-carotene contents were significantly different among cultivars (P<0.05). DPPH scavenging activity in controlled group was significantly higher than that in the Stimplex treated tomatoes (P<0.05). No significant difference in reducing power was detected among cultivars treatment groups. The study showed that the darker the tomato color, the higher the lycopene andβ-carotene contents and the stronger the reducing power.


Author(s):  
İlknur Ak ◽  
Gülen Türker

In this study, antioxidant activities of two macroalgae, Eucheuma sp. J.Agardh and Laminaria sp., J.V.Lamouroux used as food supplements were investigated. The antioxidant activity, free radical scavenging activity, the total content of phenolics, flavonoids and condensed tannins in extracts were determined. The IC50 values of the extracts of Eucheuma sp. and Laminaria sp. on DPPH scavenging activity was 2.26±0.03 mg/g and 2.63±0.03 mg/g of extract, respectively. The maximum total phenolic (5.31±0.04 mg GAE/g Ext.) were determined. According to our results, all extracts exhibited low radical scavenging activity when compared to the standards used, i.e. -tocopherol and butylated hydroxytoluene (BHT) with the inhibition percentage in the range of 48.45±0.06% (Eucheuma sp.) – 58.49±0.03% (Laminaria sp.). The highest flavonoid content was measured as 18.78±0.10 mg rutin/g of extract in Laminaria sp. The condensed tannins were not detected in Eucheuma sp. However, this value was measured as 6.24±0.60 mg CE/g of extract for Laminaria sp. According to our results, Eucheuma sp. and Laminaria sp., which are commercially sold in medicinal herb stores, are good sources of antioxidant components because of their phenolic and flavonoid contents.


Author(s):  
Nur Syafiqah Salma Mohd Shukri ◽  
Vikneswari Perumal ◽  
Tavamani Balan ◽  
Suganya Murugesu ◽  
Alfi Khatib ◽  
...  

Reactive oxygen species (ROS) or free radicals may be harmful to our body as it can cause many health problems. Antioxidants can act as radical scavengers to prevent these mechanisms. Christia vespertilionis or butterfly wings is widely found in South East Asia, traditionally used for many medical benefits. There are limited data that can be found about this plant from all possible scientific sources. Therefore, this study aimed to analyze multiple C. vespertilionis leaves extracts for its antioxidants’ capacity and infrared analysis. Five different extracts of different solvents viz, hexane, hexane: ethyl acetate, ethyl acetate, ethyl acetate: methanol, and methanol were obtained from C. vespertilionis leaves. All the extracts were assessed for 2, 2-diphenyl-1-pierylhydrazyl (DPPH) scavenging ability and ferric reducing antioxidant power (FRAP) followed by Fourier transform infrared analysis. The DPPH radical scavenging activity of ethyl acetate: methanol showed high radical scavenging activity with the lowest IC50 value of 0.549 ± 0.02 mg/mL compared to other extracts while ethyl acetate: hexane has the highest FRAP value of 271.67 ± 0.93 AAE µg ascorbic acid/g. The rapid FTIR analysis revealed the present of O-H, C-H, C=O, C=C, C-O, and N-H predominantly in the extracts. This study provides the information for further application of C. vespertilionis on various pharmacological and phytochemical aspects as not many scientific studies can be found.


2019 ◽  
Vol 16 (3) ◽  
pp. 249-255
Author(s):  
Momin Khan ◽  
Umar Ali ◽  
Anis Ur Rahman ◽  
Muhammad Ibrahim ◽  
Abdul Hameed ◽  
...  

Background: The role of small molecules as antioxidants to prevent the oxidation of other molecules and inhibit them from radical formation is the area of much interest to cure disease especially cancer. Moreover, the antioxidants play important role as stabilizers to prevent oxidation of fuels and lubricants. </P><P> Methods: In the present study, fifteen tetrakis-Schiff’s bases derivatives (1-15) were synthesized and screened for their antioxidant activities. Compounds 1-15 were synthesized by continuous stirring of reaction mixture of 1,4-bis (hydrazonomethyl)benzene (1 mmol) with various substituted aromatic aldehydes (2 mmol) in distilled water using acetic acid as catalyst at room temperature for 2-10 min. </P><P> Results: Our present study showed that all compounds are better ferrous ion-chelating agents except compound 1,4-bis((E)-((E)-(3,4-dimethoxybenzylidene)hydrazono)methyl)benzene (6) (IC50 = 329.26 &#177; 4.75 &#181;M) which has slightly low activity than the standard EDTA (IC50 = 318.40 &#177; 5.53 μM). In addition, DPPH radical scavenging activity of eleven compounds showed higher activity than the standard. However, remaining four compounds showed comparable radical scavenging activity to the standard DPPH (IC50 = 257.77 &#177; 4.60 &#181;M). </P><P> Conclusion: The series of fifteen Schiff’s bases (1-15) were synthesized and evaluated as antioxidants. From both assays, it has been demonstrated that most of the tetrakis-Schiff’s bases have potential to serve as leads for the development of antioxidant agents for future research.


2019 ◽  
Vol 9 (3) ◽  
pp. 238-243 ◽  
Author(s):  
Emine Dede ◽  
Nusret Genc ◽  
Mahfuz Elmastas ◽  
Huseyin Aksit ◽  
Ramazan Erenler

Background: Plant in Rhododendron genus that contains phenolic compounds has been used in traditional medicine and revealed considerable biological activities. Objective: Isolation and identification of antioxidant natural products from Rhododendron ungernii. Methods: Rhododendron ungernii Trautv. flowers were collected and dried in shade. The dried flowers were extracted with methanol for 3 days. The solvent was removed by reduced pressure to yield the extract which was subjected to column chromatography (Sephadex LH-20, C18 reversed phase column) to isolate catechin-7-O-glucoside (1), quercetin-3-O-β-galactoside (2), quercetin-3-O- β-xyloside (3), farrerol (4), myricetin (5), and quercetin (6). The structures of isolated compounds were elucidated by spectroscopic methods such as 1D-NMR, 2D-NMR, and LC-TOF/MS. DPPH scavenging effect, ABTS+ scavenging activity, and reducing power (FRAP) were performed for antioxidant assays of isolated natural compounds. Results: Isolated flavonoids displayed the outstanding antioxidant activities. Catechin-7-O-glucoside (1) and quercetin-3-O-β-galactoside (2) (IC50, 3.66 µg/mL) had the most DPPH• scavenging effect among the compounds. The highest ABTS•+ scavenging activity (IC50, 1.41 µg/mL) and reducing power effect (6.05 mmol TE/g comp) were observed for myricetin (5). Conclusion: R. ungernii extract and isolated compounds could be a promising antioxidant for food and pharmaceutical industries.


Author(s):  
Ch. Ravi Teja ◽  
Abraham P. Karlapudi ◽  
Neeraja Vallur ◽  
K. Mamatha ◽  
D. John Babu ◽  
...  

Abstract Background Extracellular polysaccharides (ECPs) produced by biofilm-producing marine bacterium have great applications in biotechnology, pharmaceutical, food engineering, bioremediation, and bio-hydrometallurgy industries. The ECP-producing strain was identified as Acinetobacter indicus M6 species by 16S rDNA analysis. The polymer produced by the isolate was quantified and purified and chemically analyzed, and antioxidant activities have been studied. The face-centered central composite design (FCCCD) was used to design the model. Results The results have clearly shown that the ECP was found to be endowed with significant antioxidative activities. The ECP showed 59% of hydroxyl radical scavenging activity at a concentration of 500 μg/mL, superoxide radical scavenging activity (72.4%) at a concentration of 300 μg/mL, and DPPH˙ radical scavenging activity (72.2%) at a concentration of 500 μg/mL, respectively. Further, HPLC and GC-MS results showed that the isolated ECP was a heteropolymer composed of glucose as a major monomer, and mannose and glucosamine were minor monomers. Furthermore, the production of ECP by Acinetobacter indicus M6 was increased through optimization of nutritional variables, namely, glucose, yeast extract, and MgSO4 by “Response Surface Methodology”. Moreover the production of ECP reached to 2.21 g/L after the optimization of nutritional variables. The designed model is statistically significant and is indicated by the R2 value of 0.99. The optimized medium improved the production of ECP and is two folds higher in comparison with the basal medium. Conclusions Acinetobacter indicus M6 bacterium produces a novel and unique extracellular heteropolysaccharide with highly efficient antioxidant activity. GC-MS analyses elucidated the presence of quite uncommon (1→4)-linked glucose, (1→4)-linked mannose, and (→4)-GlcN-(1→) glycosidic linkages in the backbone. The optimized medium improved the production of ECP and is two folds higher in comparison with the basal medium. The newly optimized medium could be used as a promising alternative for the overproduction of ECP.


2009 ◽  
Vol 2009 ◽  
pp. 1-6 ◽  
Author(s):  
K. Nagendra Prasad ◽  
Jing Hao ◽  
Chun Yi ◽  
Dandan Zhang ◽  
Shengxiang Qiu ◽  
...  

Antioxidant activities of wampee peel extracts using five different solvents (ethanol, hexane, ethyl acetate, butanol and water) were determined by using in-vitro antioxidant models including total antioxidant capability, 1,1-diphenyl-2-picryl hydrazyl (DPPH) radical scavenging activity, reducing power, and superoxide scavenging activity. Ethyl acetate fraction (EAF) exhibited the highest antioxidant activity compared to other fractions, even higher than synthetic antioxidant butylated hydroxyl toluene (BHT). In addition, the EAF exhibited strong anticancer activities against human gastric carcinoma (SGC-7901), human hepatocellular liver carcinoma (HepG-2) and human lung adenocarcinoma (A-549) cancer cell lines, higher than cisplatin, a conventional anticancer drug. The total phenolic content of wampee fraction was positively correlated with the antioxidant activity. This is the first report on the antioxidant and anticancer activities of the wampee peel extract. Thus, wampee peel can be used potentially as a readily accessible source of natural antioxidants and a possible pharmaceutical supplement.


2018 ◽  
Vol 2018 ◽  
pp. 1-9 ◽  
Author(s):  
Jinli Zhang ◽  
Yan Ding ◽  
Haizhou Dong ◽  
Hanxue Hou ◽  
Xiansheng Zhang

Phenolic acid profiles and antioxidant activities of outer bran, coarse bran, and shorts from blue, black, and purple wheat were analyzed. Phenolic acids were mainly in the bound form in pigmented wheat bran fractions. Phenolic acid content decreased in the order of outer bran, coarse bran, and shorts for the three pigmented wheat varieties. HPLC analysis of phenolic extracts demonstrated that the bound form of phenolic acids contained more ferulic, isoferulic, and p-coumaric acids compared to their free counterparts. Among the three pigmented wheat varieties, the bran fractions from blue wheat contained higher bound phenolic acids than the other two pigmented wheat bran fractions, except for purple coarse bran. The blue wheat outer bran had the highest total bound phenolic acid of 3458.71 μg/g while the purple wheat shorts had the lowest of 1730.71 μg/g. The contribution of bound phenolic acids to the total phenolic content and antioxidant activity was significantly higher than that of free phenolic acids. Blue wheat bran fractions had the highest radical scavenging activity against DPPH∙ while those of purple wheat gained the highest ABTS∙+ scavenging activity. High correlations were observed between TPC and radical scavenging capacities for DPPH and ABTS (R2>0.85, P<0.05).


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