Piceatannol, a natural trans-stilbene compound, inhibits human glyoxalase I

Takasawa, Ryoko; Akahane, Haruka; Tanaka, Hikari; Shimada, Nobuyoshi; Yamamoto, Takayuki; Uchida-Maruki, Hiroko; Sai, Masahiko; Yoshimori, Atsushi; Tanuma, Sei Ichi

doi:10.1016/j.bmcl.2017.01.070

Cited by 21 publications

(21 citation statements)

References 29 publications

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“…Previously, we reported the binding mode of piceatannol and human GLO I by computational simulation analyses [30]. To understand the predicted binding mode of human GLO I with piceatannol or scrupsin B, we performed docking simulations between the pharmacophore of human GLO I and these compounds, piceatannol or scrupsin B by using the co-crystal structure (PDB: 4×2A) of mouse GLO I/baicalein complex (Fig.…”

Section: Resultsmentioning

confidence: 99%

“…Moreover, piceatannol increases intracellular Ca 2+ concentrations, activates p38 mitogen-activated protein kinase (MAPK), inactivates extracellular signal–regulated kinase (ERK), and degrades procaspase-8 in leukemic cells [29]. Although Takasawa et al found that piceatannol inhibits GLO I by binding its active site [30], little is known about the inhibitory effect of passion fruit seed extract (PFSE) and piceatannol on human GLO I–mediated proliferation of cancer cells.…”

Section: Introductionmentioning

confidence: 99%

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Effect of piceatannol-rich passion fruit seed extract on human glyoxalase I–mediated cancer cell growth

Yamamoto¹,

Sato

Takai

et al. 2019

Biochemistry and Biophysics Reports

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Passion fruit seed extract (PFSE), a product rich in stilbenes such as piceatannol and scirpusin B, has various physiological effects. It is unclear whether PFSE and its stilbene derivatives inhibit cancer cell proliferation via human glyoxalase I (GLO I), the rate-limiting enzyme for detoxification of methylglyoxal. We examined the anticancer effects of PFSE in two types of human cancer cell lines with different GLO I expression levels, NCI–H522 cells (highly-expressed GLO I) and HCT116 cells (lowly-expressed GLO I). PFSE and its stilbenes inhibited GLO I activity. In addition, PFSE and its stilbenes supressed the cancer cell proliferation of NCI–H522 cells more than HCT116 cells. These observations suggest that PFSE can provide a novel anticancer strategy for prevention and treatment.

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Section: Resultsmentioning

confidence: 99%

Section: Introductionmentioning

confidence: 99%

Effect of piceatannol-rich passion fruit seed extract on human glyoxalase I–mediated cancer cell growth

Yamamoto¹,

Sato

Takai

et al. 2019

Biochemistry and Biophysics Reports

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“…Our group developed non‐GSH‐based GLO I inhibitors: TLSC702 (Fig. 1A) [23−25] and piceatannol [26]. TLSC702 was shown to induce apoptosis in tumor cells via the inhibition of GLO I, thereby increasing the amount of accumulated MG [24].…”

Section: Figmentioning

confidence: 99%

Crystal structures of human glyoxalase I and its complex with TLSC702 reveal inhibitor binding mode and substrate preference

et al. 2022

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Human glyoxalase I (hGLO I) is an enzyme for detoxification of methylglyoxal (MG) and has been considered an attractive target for the development of new anticancer drugs. In our previous report, the GLO I inhibitor TLSC702 induced apoptosis in tumor cells. Here, we determined the crystal structures of hGLO I and its complex with TLSC702. In the complex, the carboxyl O atom of TLSC702 is coordinated to Zn2+, and TLSC702 mainly shows van der Waals interaction with hydrophobic residues. In the inhibitor‐unbound structure, glycerol, which has similar functional groups to MG, was bound to Zn2+, indicating that GLO I can easily bind to MG. This study provides a structural basis to develop better anticancer drugs.

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“…While myricetin, quercetin, delphinidine, g-tocotrienol, and lovastatin have been demonstrated to induce apoptosis in HL60 cells (94)(95)(96)(97)(98). Through their Glo1 inhibitor activity TLSC702 and piceatannol, a naturally occurring stilbene, reduce the proliferation of human nonsmall cell lung cancer cells expressing high Glo1 levels (99)(100)(101).…”

Section: Therapeutic Strategiesmentioning

confidence: 99%

The Dual-Role of Methylglyoxal in Tumor Progression – Novel Therapeutic Approaches

et al. 2021

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One of the hallmarks of cancer cells is their metabolic reprogramming, which includes the preference for the use of anaerobic glycolysis to produce energy, even in presence of normal oxygen levels. This phenomenon, known as “Warburg effect”, leads to the increased production of reactive intermediates. Among these Methylglyoxal (MGO), a reactive dicarbonyl known as the major precursor of the advanced glycated end products (AGEs), is attracting great attention. It has been well established that endogenous MGO levels are increased in several types of cancer, however the MGO contribution in tumor progression is still debated. Although an anti-cancer role was initially attributed to MGO due to its cytotoxicity, emerging evidence has highlighted its pro-tumorigenic role in several types of cancer. These apparently conflicting results are explained by the hormetic potential of MGO, in which lower doses of MGO are able to establish an adaptive response in cancer cells while higher doses cause cellular apoptosis. Therefore, the extent of MGO accumulation and the tumor context are crucial to establish MGO contribution to cancer progression. Several therapeutic approaches have been proposed and are currently under investigation to inhibit the pro-tumorigenic action of MGO. In this review, we provide an overview of the early and latest evidence regarding the role of MGO in cancer, in order to define its contribution in tumor progression, and the therapeutic strategies aimed to counteract the tumor growth.

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Piceatannol, a natural trans-stilbene compound, inhibits human glyoxalase I

Cited by 21 publications

References 29 publications

Effect of piceatannol-rich passion fruit seed extract on human glyoxalase I–mediated cancer cell growth

Effect of piceatannol-rich passion fruit seed extract on human glyoxalase I–mediated cancer cell growth

Crystal structures of human glyoxalase I and its complex with TLSC702 reveal inhibitor binding mode and substrate preference

The Dual-Role of Methylglyoxal in Tumor Progression – Novel Therapeutic Approaches

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