Neuroprotective effect of 3,5-di-O-caffeoylquinic acid on SH-SY5Y cells and senescence-accelerated-prone mice 8 through the up-regulation of phosphoglycerate kinase-1

Han, Jianzhong; Miyamae, Yusaku; Shigemori, Hideyuki; Isoda, Hiroko

doi:10.1016/j.neuroscience.2010.05.049

Cited by 123 publications

(86 citation statements)

References 37 publications

(24 reference statements)

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“…9) Levels of ATP in SH-SY5Y treated with each CQA derivative were evaluated for structure-activity relationship on energy production accelerating activity in neuronal cells. The structures of tested compounds are shown in Table 1.…”

Section: )mentioning

confidence: 99%

Structure-Activity Relationship of Caffeoylquinic Acids on the Accelerating Activity on ATP Production

Miyamae

Kurisu

Han

et al. 2011

CHEMICAL & PHARMACEUTICAL BULLETIN

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Caffeoylquinic acid (CQA) is one of the phenylpropanoids found in coffee beans, sweetpotato, propolis, and other plants. [1][2][3] CQA derivatives have a variety of bioactivities such as antioxidant, antibacterial, anticancer, antihistamic, and other biological effects. [4][5][6][7][8] In our previous study, we demonstrated that 3,5-di-O-caffeoylquinic acid (3,5-di-CQA) inhibits amyloid b 1-42 -induced cellular toxicity on human neuroblastoma SH-SY5Y cells, and increases the mRNA expression level of glycolytic enzyme, phosphoglycerate kinase 1 (PGK1) and the intracellular ATP level. 9) We also indicated that 3,5-di-CQA administration induced the improvement of spatial learning and memory on senescence accelerated-prone mice 8 (SAMP8), and the overexpression of PGK1 mRNA level.9) Moreover, we found that 3,4,5-tri-Ocaffeoylquinic acid (3,4,5-tri-CQA) showed higher accelerating activity on ATP production than 3,5-di-CQA, suggesting that the number of caffeoyl groups is important for the activity (unpublished observation). However, structure-activity relationship of CQAs on the accelerating activity on ATP production are not clarified in detail.CQAs are classified into various derivatives, according to the number or the position of caffeoyl groups. The syntheses of mono-CQA derivatives including one caffeoyl group were reported by Sefkow et al. 10,11) There were, however, few reports about synthesis of CQA derivatives with more than two caffeoyl groups. Accordingly, we planed the syntheses of the CQA derivatives with more than two caffeoyl groups. We also evaluated the intracellular ATP level in SH-SY5Y cells treated with these derivatives for structure-activity relationship on the accelerating activity on ATP production. Results and DiscussionSynthesis of 1,4,5-tri-O-Caffeoylquinic Acid CQA derivatives that caffeoyl groups bind to 3-, 4-, and 5-hydroxyl groups in quinic acid are found abundantly in natural resources. On the other hand, the derivatives that caffeoyl group binds to 1-hydroxyl group were rare in them. It was also interested whether they have the accelerating activity on ATP production. So, we initially synthesized 1,4,5-tri-O-caffeoylquinic acid (1,4,5-tri-CQA) as shown in Chart 1. Isopropyridene quinide (2) was synthesized from commercially available quinic acid (1), according to previously reported method.12) Di-O-acetylcaffeoyl chloride (b) was used for followed esterification reaction. Acid chloride b was obtained from commercially available caffeic acid (a) in two steps, acetylation with Ac 2 O in pyridine and chlorination with SOCl 2 . 10) Isopropyridene quinide (2) reacted with acid chloride b in pyridine and CH 2 Cl 2 to afford ester 3 in 50% yield.11) The acetonide group of 3 was selectively cleaved with 90% trifluoroacetic acid (TFA) to give diol 4 in 61% yield. Diol 4 was heated with five equivalents of c under reflux in benzene for 24 h to afford tri-ester 5 in 86% yield. Hydrolysis of all protecting groups was accomplished with 1 M HCl at room temperature to obtain 1,4,5-tri-CQA (6) in 46...

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Section: )mentioning

confidence: 99%

Structure-Activity Relationship of Caffeoylquinic Acids on the Accelerating Activity on ATP Production

Miyamae

Kurisu

Han

et al. 2011

CHEMICAL & PHARMACEUTICAL BULLETIN

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“…In our previous study, we reported that neuroprotective effect from Aβ42-induced cytotoxicity of CQAs, [19][20][21] and the inhibition of the amyloid β aggregation by CQAs and acteoside (2). 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.…”

Section: Resultsmentioning

confidence: 96%

“…19) We also reported that CQAs treatment improved spatial learning memory on senescence accelerated-prone mice 8 through increasing the mRNA expression of phosphoglycerate kinase 1. 20,21) Furthermore, acteoside (2) found in natural resources of Orobanche minor, olive, and other plants, 22) is reported that it protects human neuroblastoma SH-SY5Y cells against amyloid β cell injury by protecting reactive oxygen species (ROS) production and modulating apoptotic signal pathway. 23) We also reported that CQAs and acteoside (2) possessed antiamyloidogenic effect.…”

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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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“…The hydroxycinnamic acid, 3,5-di-caffeoylquinic acid (6.7 mg/kg b.w. ), also showed a pronounced effect, being able to decrease in a significant manner escape latency time, by increasing PGK1 and mRNA expression, and also ATP production (Han et al 2010).…”

Section: Bioactive Compounds With In Vivo Neuroprotectivementioning

confidence: 90%

Neurocognitive Improvement Through Plant Food Bioactives: A Particular Approach to Alzheimer’s Disease

Martins

Ferreira

2017

Food Bioactives

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Neuroprotective effect of 3,5-di-O-caffeoylquinic acid on SH-SY5Y cells and senescence-accelerated-prone mice 8 through the up-regulation of phosphoglycerate kinase-1

Cited by 123 publications

References 37 publications

Structure-Activity Relationship of Caffeoylquinic Acids on the Accelerating Activity on ATP Production

Structure-Activity Relationship of Caffeoylquinic Acids on the Accelerating Activity on ATP Production

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

Neurocognitive Improvement Through Plant Food Bioactives: A Particular Approach to Alzheimer’s Disease

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