Protective effects of caffeoylquinic acids on the aggregation and neurotoxicity of the 42-residue amyloid β-protein

Miyamae, Yusaku; Kurisu, Manami; Murakami, Kazuma; Han, Jianzhong; Isoda, Hiroko; Irie, Kazuhiro; Shigemori, Hideyuki

doi:10.1016/j.bmc.2012.08.001

Cited by 81 publications

(68 citation statements)

References 37 publications

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“…4) The similarities in Aβ and IAPP oligomers can be used to investigate the prevention of oxidative stress and amyloid aggregation inhibition related to AD and T2D, since potent therapeutic agents such as antioxidants with a catechol moiety, proved to inhibit Aβ aggregation, [12][13][14][15][16] may play a key role inhibiting the aggregation of human IAPP (hIAPP) in case of patients with diabetes.…”

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confidence: 99%

Inhibitory Activities of Antioxidant Flavonoids from <i>Tamarix gallica</i> on Amyloid Aggregation Related to Alzheimer’s and Type 2 Diabetes Diseases

Hmidene

Hanaki

Murakami

et al. 2017

Biological & Pharmaceutical Bulletin

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The prevention of amyloid aggregation is promising for the treatment of age-related diseases such as Alzheimer's (AD) and type 2 diabetes (T2D). Ten antioxidant flavonoids isolated from the medicinal halophyte Tamarix gallica were tested for their amyloid aggregation inhibition potential. Glucuronosylated flavonoids show relatively strong inhibitory activity of Amyloid β (Aβ) and human islet amyloid polypeptide (hIAPP) aggregation compared to their aglycone analogs. Structure-activity relationship of the flavonoids suggests that the catechol moiety is important for amyloid aggregation inhibition, while the methylation of the carboxyl group in the glucuronide moiety and of the hydroxyl group in the aglycone flavonoids decreased it.Key words amyloid aggregation; glucuronosylated flavonoid; Tamarix gallica; Alzheimer's disease; type 2 diabetes The incidence of both disturbances Alzheimer's disease (AD) and type 2 diabetes (T2D) is increasing and has become a major public health concern in many industrialized countries. Despite intense research, best strategies to treat/prevent these costly diseases are still under investigation. However, it is now widely recognized that AD and T2D share many pathophysiological features including increased oxidative stress and amyloid aggregation. 1-4)Amyloid β (Aβ) is the component of the amyloid deposits in the AD brain, 5) while the component of the amyloidogenic peptide deposit in the diabetic pancreatic islets of Langerhans is identified as islet amyloid polypeptide (IAPP), a 37-amino acid peptide. 6,7) Although the amino acid sequences of amyloidogenic proteins are diverse, they all adopt a similar structure in aggregates called cross-β-spine.8) Extensive studies in the past years have found that, similar to Aβ 1-42 , IAPP forms early intermediate assemblies as spherical oligomers 9,10) that are recognized by soluble Aβ oligomers antibody, 11) implicating that these oligomers possess a common folding pattern or conformation.4) The similarities in Aβ 1-42 and IAPP oligomers can be used to investigate the prevention of oxidative stress and amyloid aggregation inhibition related to AD and T2D, since potent therapeutic agents such as antioxidants with a catechol moiety, proved to inhibit Aβ aggregation, 12-16) may play a key role inhibiting the aggregation of human IAPP (hIAPP) in case of patients with diabetes.The powerful antioxidant activity of the medicinal halophyte Tamarix gallica L. has been reported as exhibiting a remarkable spectrum of biochemical and pharmacological activities. Although traditionally used for the treatment of various liver disorders and marketed as a herbal medicine in many countries, [17][18][19] there have been no reports on the use of this plant for the treatment or prevention of AD or T2D. Therefore, the aim of this research is to investigate the protective effect of T. gallica towards both disturbances by isolation and identification of the Aβ and hIAPP aggregation inhibitors with antioxidant potential. MATERIALS AND METHODS MaterialsThe aerial par...

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confidence: 99%

Inhibitory Activities of Antioxidant Flavonoids from <i>Tamarix gallica</i> on Amyloid Aggregation Related to Alzheimer’s and Type 2 Diabetes Diseases

Hmidene

Hanaki

Murakami

et al. 2017

Biological & Pharmaceutical Bulletin

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“…24,25) Combined with these previous studies and this study about HGF promoting activity of CQAs such as 4,5-di-O-caffeoylquinic acid (1) and acteoside (2), they have a potential to cure neurodegenerative diseases like AD, the evidence that having not only the direct protect activity against amyloid β toxicity but also the promoting activity of HGF. There are some reports on the mechanism of founded inducers to promote HGF production.…”

Section: Resultsmentioning

confidence: 60%

“…23) We also reported that CQAs and acteoside (2) possessed antiamyloidogenic effect. 24,25) With the raising interest studies these caffeic acid derivatives have a potential to promote production of HGF that is also suggested to regulate neuronal survival, 9,10) we performed HGF enzyme-linked immunosorbent assay (ELISA). Here, we describe caffeic acid derivatives like 4,5-di-O-caffeoylquinic acid (1) or acteoside (2) potently promoted HGF production in Neonatal Normal Human Dermal Fibroblasts (NHDF).…”

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confidence: 99%

Induction of Hepatocyte Growth Factor Production in Human Dermal Fibroblasts by Caffeic Acid Derivatives

Kurisu

Nakasone

Miyamae

et al. 2013

Biological & Pharmaceutical Bulletin

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Hepatocyte growth factor (HGF) has mitogenic, motogenic, and morphogenic activities in epithelial cells. Induction of HGF production may be involved in organ regeneration, wound healing and embryogenesis. In this study, we examined the effects of caffeic acid derivatives including 4,5-di-O-caffeoylquinic acid (1) and acteoside (2) on HGF production in Neonatal Normal Human Dermal Fibroblasts (NHDF). Both 4,5-di-O-caffeoylquinic acid (1) and acteoside (2) significantly induced HGF production dose-dependent manner. To know the important substructure for HGF production activity, we next investigated the effect of the partial structure of these caffeic acid derivatives. From the results, caffeic acid (3) showed strong activity on the promotion of HGF production, while hydroxytyrosol (4) and quinic acid (5) didn't show any activity. Our findings suggest that the caffeoyl moiety of caffeic acid derivatives is essential for accelerated production of HGF. The compound which has the caffeoyl moiety may be useful for the treatment of some intractable organ disease.

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“…9) Miyamae and his colleagues reported that CQAs inhibited the aggregation of neurotoxic Aβ 42 , and they also reported that 4,5-diCQA and 3,4,5-triCQA more strongly inhibited the aggregation of Aβ 42 than other CQAs. 10) Moreover, the four diCQAs (3,4-, 3,5-, 4,5-, and 1,5-diCQAs) inhibited the replication to a greater extent than CA and 5-CQA. 11) Our previous experiments revealed that sweet potato leaves have a higher CQA content compared to other major commercial vegetables.…”

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confidence: 94%

Single-laboratory validation for the determination of caffeic acid and seven caffeoylquinic acids in sweet potato leaves

Sasaki

Oki

Kobayashi

et al. 2014

Bioscience, Biotechnology, and Biochemistry

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A single-laboratory validation study was conducted on an HPLC method for the detection and quantification of caffeic acid (CA) and seven species of caffeoylquinic acids (CQAs) in lyophilized sweet potato leaves. The procedure for extraction of the analytes from the matrix and the HPLC conditions for the efficient separation of CA and CQAs were optimized. In the proposed method, a relative response factor to one of the CQAs (5-CQA) was used to quantify the others. The method performed well in terms of precision when carried out on five different days and demonstrated Horwitz ratio (HorRat) scores ranging from 0.5 to 1.0 for all analytes, which were well within the limits of performance acceptability. Accuracy testing at three levels showed an overall recovery of 94% when duplicated on five different days. Moreover, a stability study revealed that all analytes in both standard solution and sample extract were stable for 28 days.

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Protective effects of caffeoylquinic acids on the aggregation and neurotoxicity of the 42-residue amyloid β-protein

Cited by 81 publications

References 37 publications

Inhibitory Activities of Antioxidant Flavonoids from <i>Tamarix gallica</i> on Amyloid Aggregation Related to Alzheimer’s and Type 2 Diabetes Diseases

Inhibitory Activities of Antioxidant Flavonoids from <i>Tamarix gallica</i> on Amyloid Aggregation Related to Alzheimer’s and Type 2 Diabetes Diseases

Induction of Hepatocyte Growth Factor Production in Human Dermal Fibroblasts by Caffeic Acid Derivatives

Single-laboratory validation for the determination of caffeic acid and seven caffeoylquinic acids in sweet potato leaves

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