Caffeoylquinic acids from aronia juice inhibit both dipeptidyl peptidase IV and α-glucosidase activities

Imai, Momoko; Yamane, Toshimi; Kozuka, Miyuki; Takenaka, Shigeo; Sakamoto, Tatsuji; Ishida, Tetsuo; Nakagaki, Takenori; Nakano, Yoshihisa; Inui, Hiroshi

doi:10.1016/j.lwt.2020.109544

Cited by 20 publications

(9 citation statements)

References 33 publications

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“…Another way to improve glucose tolerance in diabetic patients is by enhancing the glucose-regulating hormones, namely glucagon-like peptide-1 (GLP-1) and glucose-dependent insulinotropic polypeptide (GIP) [ 83 ]. Dipeptidyl peptidase-IV (DPP-IV) is the enzyme responsible for the degradation of GLP-1, GIP [ 84 ], and gliptins, such as sitagliptin, vildagliptin, saxagliptin, alogliptin, linagliptin, gemigliptin, and teneligliptin, which are commercialized in the USA, Europe, Japan, and Korea as DPP-IV inhibitors [ 85 ].…”

Section: Resultsmentioning

confidence: 99%

Sugarcane Straw Polyphenols as Potential Food and Nutraceutical Ingredient

Oliveira¹,

Carvalho²,

Oliveira³

et al. 2022

Foods

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The sugarcane processing industry generates a large amount of straw, which has a negative environmental impact, and high costs are associated with their elimination, wasting their potential bioactive value attributed to their richness in polyphenols. In this study, an ethanolic extract produced from sugarcane straw was screened for its phenolic compounds content, and the potential use of this extract in the development of a food ingredient was further evaluated. Fifty different secondary metabolites belonging to the hydroxybenzoic acids, hydroxycinnamic acids, and flavonoids were identified by liquid chromatography–electrospray ionization–ultrahigh-resolution—quadrupole time of flight–mass spectrometry (LC-ESI-UHR-QqTOF-MS). The predominant phenolic compounds found were 4-hydroxybenzaldehyde, chlorogenic acid, and 5-O-feruloylquinic acid. The obtained extracts showed strong potential as food preservatives by exhibiting (a) antioxidant activity using both 2.2′-azino-bis (3-ethylbenzothiazoline-6-sulphonic acid) diammonium salt radical cation (ABTS) and 2,2-diphenyl-1-picrylhydrazyl (DPPH) methods; and (b) antimicrobial capacity, with a minimum inhibitory concentration of 50 mg/mL for Staphylococcus aureus, 74% inhibition for Bacillus cereus, and 44% for Salmonella enterica; and (c) the capacity to inhibit a food browning enzyme, tyrosinase (28–73% for 1–8 mg/ mL). Moreover, the extracts showed antidiabetic potential by inhibiting the enzymes α-glucosidase (15–38% for 1.25–5.00 mg/mL) and dipeptidyl peptidase-IV (DPP-IV) (62–114% for 0.31–5.00 mg/mL). The extract (0.625 mg/mL) also exhibited the capacity to reduce proinflammatory mediators (i.e., interleukins 6 and 8, and tumor necrosis factor alpha) when Caco-2 cells were stimulated with interleukin 1 beta. Thus, sugarcane straw extract, which is rich in phenolic compounds, showed high potential to be used in the development of food-preservative ingredients owing to its antioxidant and antimicrobial potential, and to be explored as a food supplement in diabetes prevention and as coadjuvant to reduce intestinal inflammation by reducing proinflammatory mediators.

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Section: Resultsmentioning

confidence: 99%

Sugarcane Straw Polyphenols as Potential Food and Nutraceutical Ingredient

Oliveira¹,

Carvalho²,

Oliveira³

et al. 2022

Foods

View full text Add to dashboard Cite

show abstract

“…Apart from α-glucosidase, dipeptidyl peptidase IV (DPP IV), which could inactivate intestinal peptide glucagon-like peptide 1 (GLP-1) and gastric inhibitory peptide (GIP), plays a crucial role in type 2 diabetes mellitus. 153 A study by Imai et al 154 demonstrated that 3-CQA (2) and 4-CQA (6) possessed inhibitory activity against DPP IV, with IC 50 values of 0.19 and 0.05 μM, respectively.…”

Section: Biological Activities Of Natural Cqasmentioning

confidence: 99%

Current Advances in Naturally Occurring Caffeoylquinic Acids: Structure, Bioactivity, and Synthesis

Liu

Zhang

et al. 2020

J. Agric. Food Chem.

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Caffeoylquinic acids (CQAs) are a broad class of secondary metabolites that have been found in edible and medicinal plants from various families. It has been 100 years since the discovery of chlorogenic acid in 1920. In recent years, a number of naturally derived CQAs have been isolated and structurally elucidated. Accumulated evidence demonstrate that CQAs have a wide range of biological activities, such as antioxidation, antibacterial, antiparasitic, neuroprotective, anti-inflammatory, anticancer, antiviral, and antidiabetic effects. Up to date, some meaningful progresses on the biosynthesis and total synthesis of CQAs have also been made. Therefore, it is necessary to comprehensively summarize the structure, biological activity, biosynthesis, and chemical synthesis of CQAs. This review provides extensive coverage of naturally occurring CQAs discovered from 1990 until 2020. Modern isolation techniques, chemical data (including structure, biosynthesis, and total synthesis), and bioactivity are summarized. This would be helpful for further research of CQAs as potential pharmaceutical agents.

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“…Furthermore, in preclinical studies, CQAs are able to inhibit α‐glucosidase and were proposed to mitigate the incidence of so‐called lifestyle‐related diseases, such as diabetes (Imai et al. , 2020). Every day, we ingest CQAs from plant‐derived food, including fruits and vegetables.…”

Section: Introductionmentioning

confidence: 99%

Caffeoylquinic acids: chemistry, biosynthesis, occurrence, analytical challenges, and bioactivity

et al. 2021

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SUMMARY Caffeoylquinic acids (CQAs) are specialized plant metabolites we encounter in our daily life. Humans consume CQAs in mg‐to‐gram quantities through dietary consumption of plant products. CQAs are considered beneficial for human health, mainly due to their anti‐inflammatory and antioxidant properties. Recently, new biosynthetic pathways via a peroxidase‐type p‐coumaric acid 3‐hydroxylase enzyme were discovered. More recently, a new GDSL lipase‐like enzyme able to transform monoCQAs into diCQA was identified in Ipomoea batatas. CQAs were recently linked to memory improvement; they seem to be strong indirect antioxidants via Nrf2 activation. However, there is a prevalent confusion in the designation and nomenclature of different CQA isomers. Such inconsistencies are critical and complicate bioactivity assessment since different isomers differ in bioactivity and potency. A detailed explanation regarding the origin of such confusion is provided, and a recommendation to unify nomenclature is suggested. Furthermore, for studies on CQA bioactivity, plant‐based laboratory animal diets contain CQAs, which makes it difficult to include proper control groups for comparison. Therefore, a synthetic diet free of CQAs is advised to avoid interferences since some CQAs may produce bioactivity even at nanomolar levels. Biotransformation of CQAs by gut microbiota, the discovery of new enzymatic biosynthetic and metabolic pathways, dietary assessment, and assessment of biological properties with potential for drug development are areas of active, ongoing research. This review is focused on the chemistry, biosynthesis, occurrence, analytical challenges, and bioactivity recently reported for mono‐, di‐, tri‐, and tetraCQAs.

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Caffeoylquinic acids from aronia juice inhibit both dipeptidyl peptidase IV and α-glucosidase activities

Cited by 20 publications

References 33 publications

Sugarcane Straw Polyphenols as Potential Food and Nutraceutical Ingredient

Sugarcane Straw Polyphenols as Potential Food and Nutraceutical Ingredient

Current Advances in Naturally Occurring Caffeoylquinic Acids: Structure, Bioactivity, and Synthesis

Caffeoylquinic acids: chemistry, biosynthesis, occurrence, analytical challenges, and bioactivity

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