A new synthesis of 4′-resveratrol esters and evaluation of the potential for anti-depressant activity

Acerson, Mark J.; Fabick, Kimberly Michelle; Wong, Yong; Blake, Crystal; Lephart, Edwin D.; Andrus, Merritt B.

doi:10.1016/j.bmcl.2013.03.046

Cited by 12 publications

(8 citation statements)

References 34 publications

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“…3-(4,5-Dimethylthiazol-2-yl)-2,5-diphenyltetrazolium bromide (AC158990050) (MTT) was purchased from Acros Organics (Morris Plains, NJ, USA). 4′-Butyrate resveratrol (BuRV), 4′-Isobutyrate resveratrol (IsoRV) and 4′-Pivalate resveratrol (PIV) were synthesized by the Andrus lab in the Department of Chemistry and Biochemistry at Brigham Young University [ 18 ].…”

Section: Methodsmentioning

confidence: 99%

“…Previous studies have demonstrated that RES esterified at the 4′-hydroxyl increases chemotherapeutic activity [ 17 ]. Therefore, in this study we esterified the 4′-hydroxy group with pivalate, butyrate, and isobutyrate groups ( Figure 1 ) [ 18 ]. We tested the effects of the RES derivatives on tumor cell viability and on calcium signaling activity.…”

Section: Introductionmentioning

confidence: 99%

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The Effects of 4′-Esterified Resveratrol Derivatives on Calcium Dynamics in Breast Cancer Cells

et al. 2017

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Triple-negative breast cancer is a highly aggressive subtype of breast cancer. Frequently, breast cancer cells modulate their calcium signaling pathways to optimize growth. Unique calcium pathways in breast cancer cells could serve as a way to target tumorigenic cells without affecting normal tissue. Resveratrol has previously been shown to activate calcium signaling pathways. We use cell viability, single-cell calcium microscopy, and RT-PCR assays to determine the activity and mechanism of three different 4′-esterified resveratrol derivatives. We demonstrate that two of the derivatives reduce cell viability more effectively than resveratrol in MDA-MB-231 human breast cancer cells. The derivatives also activate similar pro-apoptotic calcium signaling pathways. In particular, the pivalated and butyrated resveratrol derivatives are intriguing putative chemotherapeutics because they are more effective at decreasing cell viability in vitro and inhibiting the plasma membrane Ca2+-ATPase, a protein that is often modulated in breast cancer.

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Section: Methodsmentioning

confidence: 99%

Section: Introductionmentioning

confidence: 99%

The Effects of 4′-Esterified Resveratrol Derivatives on Calcium Dynamics in Breast Cancer Cells

et al. 2017

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“…Their report suggested that this resveratrol analog, with increased stability, may be incorporated into cosmetic formulations that can whiten human skin without skin irritation [17]. In this effort, our laboratory developed the novel synthesis of a resveratrol analog (i.e., 4′ acetoxy-resveratrol) to obtain enhanced stability and bioavailability for cosmetic utility in order to advance dermal health, along with other applications [18]. In this manner, natural resveratrol could then be compared to our new 4′ acetoxy resveratrol analog in gene array studies, since natural resveratrol appears to be an effective dermal treatment in antioxidant skin care formulations [19,20,21].…”

Section: Introductionmentioning

confidence: 99%

Resveratrol, 4′ Acetoxy Resveratrol, R-equol, Racemic Equol or S-equol as Cosmeceuticals to Improve Dermal Health

Lephart

2017

IJMS

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Phytochemicals are botanical compounds used in dermatology applications as cosmeceuticals to improve skin health. Resveratrol and equol are two of the best-known polyphenolic or phytoestrogens having similar chemical structures and some overlapping biological functions to 17β-estradiol. Human skin gene expression was reviewed for 28 different biomarkers when resveratrol, 4′ acetoxy resveratrol (4AR), R-equol, racemic equol or S-equol were tested. Sirtuin 1 activator (SIRT 1) was stimulated by resveratrol and 4AR only. Resveratrol, R-equol and racemic equol were effective on the aging biomarkers proliferating cell nuclear factor (PCNA), nerve growth factor (NGF), 5α-reductase and the calcium binding proteins S100 A8 and A9. Racemic equol and 4AR displayed among the highest levels for the collagens, elastin and tissue inhibitor of the matrix metalloproteinase 1 (TIMP 1). S-equol displayed the lowest level of effectiveness compared to the other compounds. The 4AR analog was more effective compared to resveratrol by 1.6-fold. R-equol and racemic equol were almost equal in potency displaying greater inhibition vs. resveratrol or its 4′ analog for the matrix metalloproteinases (MMPs), but among the inflammatory biomarkers, resveratrol, 4AR, R-equol and racemic equol displayed high inhibition. Thus, these cosmeceuticals display promise to improve dermal health; however, further study is warranted to understand how phytochemicals protect/enhance the skin.

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“…Resveratrol was initially studied for its potential for treating cancer [26], but also gained recognition for its ability to reduce cardiovascular disease [27]. More recently resveratrol was shown to alleviate depressive-like symptoms induced by stress in rats [25, 28-34], and that at higher doses causes an increase in biogenic amines in the hippocampus and the cortex in mice [24]. In this study we examined the antidepressant-like effect of resveratrol in a non-induced model of depression, the Wistar-Kyoto (WKY) rats.…”

Section: Introductionmentioning

confidence: 99%

Antidepressant effects of resveratrol in an animal model of depression

Hurley

Akinfiresoye

Kalejaiye

et al. 2014

Behavioural Brain Research

148

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Resveratrol (3,4’,5-trihydroxy-trans-stilbene) is a natural non-flavonoid polyphenol antioxidant extracted from red grapes in the processing of wine. Initially it was studied for its potential as anticancer drug, and later was found to reduce cardiovascular disease. More recently resveratrol was shown to alleviate depressive-like symptoms induced by stress or other means in mice and rats. The major purpose of this study was to investigate whether resveratrol would manifest an antidepressant effect in Wistar-Kyoto (WKY) rats, a putative and non-induced animal model of depression, and whether this effect might be associated with an increase in hippocampal and frontal cortical brain-derived neurotrophic factor (BDNF), a protein implicated in chronic effects of many antidepressants. Adult male WKY rats were injected with two doses of resveratrol (10 and 40 mg/kg, i.p.) and their behavior in the open field locomotor activity (LMA), forced swim test (FST: a measure of helplessness), and sucrose preference test (SPT: a measure of anhedonia) was evaluated after a single acute injection or following 7 days of daily treatment. Both acute and chronic administration of resveratrol resulted in a dose-dependent decrease in FST. However, only chronic resveratrol resulted in dose-dependent increase in sucrose consumption. LMA was not affected by any treatment. Parallel to the observed behavioral effects the level of hippocampal, but not frontal cortical, BDNF was also dose-dependently elevated after chronic resveratrol administration. These findings indicate an antidepressant-like effect of resveratrol in an animal model of depression possibly via activation of hippocampal BDNF, and suggest therapeutic potential of resveratrol in at least a subpopulation of depressed patients.

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A new synthesis of 4′-resveratrol esters and evaluation of the potential for anti-depressant activity

Cited by 12 publications

References 34 publications

The Effects of 4′-Esterified Resveratrol Derivatives on Calcium Dynamics in Breast Cancer Cells

The Effects of 4′-Esterified Resveratrol Derivatives on Calcium Dynamics in Breast Cancer Cells

Resveratrol, 4′ Acetoxy Resveratrol, R-equol, Racemic Equol or S-equol as Cosmeceuticals to Improve Dermal Health

Antidepressant effects of resveratrol in an animal model of depression

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