Dicaffeoylquinic Acid-Enriched Fraction of <i>Cichorium glandulosum</i> Seeds Attenuates Experimental Type 1 Diabetes via Multipathway Protection

Tong, Jing; B, Ma; Ge, Lanlan; Mo, Qigui; Zhou, Gao; He, Jingsheng; Wang, Youwei

doi:10.1021/acs.jafc.5b04552

Cited by 22 publications

(16 citation statements)

References 44 publications

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“…Compound G was identified as 3,5-dicaffeoylquinic acid (3,5-diCQA) based on the results of 1 H and 13 C NMR analyses. The spectroscopic data are consistent with the results of previous investigations of Cichorium glandulosum seeds [12].…”

Section: Isolation and Identification Of Phenolic Compoundssupporting

confidence: 92%

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Polyphenolic profiles in lettuce (Lactuca sativa L.) after CaCl2 treatment and cold storage

Materska

Olszówka

Chilczuk

et al. 2018

Eur Food Res Technol

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Lettuce (Lactuca sativa L.) is a popular vegetable with the health-enhancing properties determined by high levels of antioxidant polyphenols as chlorogenic acids and other derivatives of caffeic acid or flavonoids. In this study, changes in the phenolic compound profiles in the lettuce leaves induced by application of CaCl 2 before harvest and cold storage were studied. For the first time quantitative analysis of individual phenolic compounds on the basis of standards isolated from lettuce leaves was performed. Compounds were identified using HPLC, LC-MS, 1 H and 13 CNMR techniques. The dominant compounds were 2,3-dicaffeoyltartaric (2,3-diCTA), 5-O-caffeoylquinic (5-OCQA) and caffeoyltartaric (CTA) acids, with content of 5.7, 2.5 and 0.981 mg/g DM, respectively. The levels of individual phenolic compounds, total phenolics and antioxidant activity (DPPH assay) in plants treated by CaCl 2 were determined throughout the storage period (7 and 14 days) at 4 °C. To ascertain the relationship between the content of individual compounds, total phenols, antioxidant activities and storage time, Pearson's correlation analysis was used. The best correlation between the storage length and compound concentration was observed for 2,3-diCTA (R 2 = 0.866) and caffeoylmalic acid (CMA) (R 2 = 0.750). Application of CaCl 2 (0.05M) on lettuce resulted in an increase in the levels of CTA, 2.3-diCTA and 5-OCQA about 120, 65 and 57%, respectively, compared to the control stored for 7 days in the same conditions and had a favourable effect on the antioxidant activity (R 2 = 0.985). The present paper shows that CaCl 2 may be used as an agent that influences the stability of health-promoting compounds of cold-stored lettuce.

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Section: Isolation and Identification Of Phenolic Compoundssupporting

confidence: 92%

“…Recent research results have demonstrated that another caffeic acid derivative, 3,5-dicaffeoylquinic acid (3,, exhibits α-glucosidase inhibitory activity. Its presence in extracts of Cichorium glandulosum seeds contributed to the attenuation of type I diabetes [12].…”

Section: Introductionmentioning

confidence: 99%

Polyphenolic profiles in lettuce (Lactuca sativa L.) after CaCl2 treatment and cold storage

Materska

Olszówka

Chilczuk

et al. 2018

Eur Food Res Technol

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“…Sinapine thiocyanate (99.0 % HPLC) was isolated from rapeseed meal according to the method outlined by Mailer (2008). 3,4-di-O-caffeoylquinic, 3,5-di-Ocaffeoylquinic and 4,5-di-O-caffeoylquinic acids (>99.0 % HPLC) were isolated from yerba mate leaves, following the procedure previously described in Tong et al (2015).…”

Section: Chemicalsmentioning

confidence: 99%

Release of phenolic acids from sunflower and rapeseed meals using different carboxylic esters hydrolases from Aspergillus niger

Laguna

Odinot

Bisotto

et al. 2019

Industrial Crops and Products

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Sunflower and rapeseed meals are agro-industrial coproducts that contain high amount of phenolics (1-4 % dry matter), mostly as esters of caffeic acid (CA) and sinapic acid (SA), respectively. The enzymatic hydrolysis of the ester bonds enables to recover the corresponding free phenolic acids that are bioactive compounds and platform molecules for various applications in green chemistry. Here we aimed to find the best route for producing free CA and SA by applying various fungal carboxylic ester hydrolases from recombinant Aspergillus niger strains either directly on crude meal or on their phenolic extracts obtained by methanolic extraction. Two types of meals were studied: (i) industrial (commercial) meals (I-meals), produced by a process that includes cooking at 95-100°C and steam desolventizing at 105-107°C, and (ii) non-industrial meals (NI-meals) obtained at pilot-scale with much milder heat treatment, that offer a higher total phenolic content. CA release through hydrolysis of sunflower meal (SFM) was successfully achieved with A. niger type-B feruloyl esterase (AnFaeB) and chlorogenic acid esterase (ChlE). Maximal amount of free CA released was of 54.0 ± 1.1 to 59.8 ± 2.1 µmol/g defatted dry matter (DDM) from I-SFM (94-100% hydrolysis yield) against 42.0 ± 1.1 to 52.3 ± 0.2 µmol/g DDM (59-73% hydrolysis yield) from NI-SFM in which CA release was hampered by a phenolic oxidation side-reaction, seemingly due to meal endogenous polyphenol oxidase activities. AnFaeB and ChlE hydrolysis of phenolic extracts from NI-SFM increased the CA amount obtained to 55.0-68.1 µmol/g DDM (77-95% hydrolysis yield). In all cases, AnFaeB showed broader specificity towards SFM caffeoyl quinic acid isomers than ChlE. In particular, ChlE did not hydrolyze 3-O-caffeoylquinic acid. The maximal amount of free SA released by AnFaeA hydrolysis was 41.3 ± 0.3 µmol/g DDM from NI-SFM (50% hydrolysis yield) and 32.3 ± 0.4 µmol/g DDM from the phenolic extract (64% hydrolysis yield), with AnFaeA also having sinapine transesterification activity that led to the synthesis of 1,2-di-Osinapoyl-β-D-glucose. Finally, of all the substrates tested for enzymatic hydrolysis in our conditions, I-RSM and NI-SFM extract showed the best compromise between initial total phenolic content, hydrolysis yields and amounts of CA/SA released.

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“…The improvement of glucose tolerance in the EFAA group is presumed to be the effect of 3,5‐diCQA, which is another main compound that is not 4,5‐diCQA (Kang et al, ). According to research by Tong et al (), a Cichorium glandulosum seed n‐BuOH fraction with 3,5‐diCQA as the main compound has a hypoglycemic effect and improves glucose tolerance in streptozotocin‐induced diabetic mice. To sum up, although further studies are required, 4,5‐diCQA is not effective in improving glucose tolerance, and it is presumed that 3,5‐diCQA is involved in improving the glucose tolerance of Artemisia argyi .…”

Section: Resultsmentioning

confidence: 99%

4,5‐dicaffeyolquinic acid improves high‐fat diet‐induced cognitive dysfunction through the regulation of insulin degrading enzyme

et al. 2019

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This study was performed to investigate the effects of Artemisia argyi and 4,5‐dicaffeyolquinic acid (4,5‐diCQA) as a main compound of ethyl acetate fraction from Artemisia argyi (EFAA) on high‐fat diet (HFD)‐induced cognitive dysfunction. Both EFAA and 4,5‐diCQA were effective in improving cognitive function on HFD‐induced cognitive dysfunction. In brain tissue analysis, it was confirmed that EFAA and 4,5‐diCQA inhibited the reduction of neurotransmitters as well as oxidative stress and mitochondrial dysfunction. In addition, they inhibited amyloid β (Aβ) accumulation by increasing the expression of insulin‐degrading enzyme and consequently prevented apoptosis. In conclusion, it is presumed that Artemisia argyi may help to improve the cognitive impairment due to the HFD, and it is considered that this effect is closely related to the physiological activity of 4,5‐diCQA. Practical applications Artemisia argyi is used in traditional herbal medicine in Asia. Type 2 diabetes mellitus has been proven by a variety of epidemiological studies to be a risk factor for cognitive impairment, such as Alzheimer’s disease. This study confirmed that 4,5‐diCQA is a bioactive compound of Artemisia argyi on improving HFD‐induced cognitive dysfunction. Therefore, this study can provide useful information to the effect of Artemisia argyi and related substance.

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Dicaffeoylquinic Acid-Enriched Fraction of Cichorium glandulosum Seeds Attenuates Experimental Type 1 Diabetes via Multipathway Protection

Cited by 22 publications

References 44 publications

Polyphenolic profiles in lettuce (Lactuca sativa L.) after CaCl2 treatment and cold storage

Polyphenolic profiles in lettuce (Lactuca sativa L.) after CaCl2 treatment and cold storage

Release of phenolic acids from sunflower and rapeseed meals using different carboxylic esters hydrolases from Aspergillus niger

4,5‐dicaffeyolquinic acid improves high‐fat diet‐induced cognitive dysfunction through the regulation of insulin degrading enzyme

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