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Piceatannol, (E)-

$101

  • Brand : BIOFRON

  • Catalogue Number : BD-P0902

  • Specification : 98.0%(HPLC&TLC)

  • CAS number : 10083-24-6

  • Formula : C14H12O4

  • Molecular Weight : 244.24

  • PUBCHEM ID : 667639

  • Volume : 25mg

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Catalogue Number

BD-P0902

Analysis Method

HPLC,NMR,MS

Specification

98.0%(HPLC&TLC)

Storage

2-8°C

Molecular Weight

244.24

Appearance

Off-White crystalline powder

Botanical Source

Rumex madaio MakinoR. daiwoo Makino/Found in Norway spruce, Vouacapoua macropetala, Pericopsis angolensis and other spp. Constit. of peanuts, Vaccinium sp. berries and grapes

Structure Type

Stilbenes

Category

Standards;Natural Pytochemical;API

SMILES

C1=CC(=C(C=C1C=CC2=CC(=CC(=C2)O)O)O)O

Synonyms

3,3',4'5-Tetrahydroxystilbene/E-Piceatannol/1,2-Benzenediol, 4-[(E)-2-(3,5-dihydroxyphenyl)ethenyl]-/3,3′,4,5′-Tetrahydroxy-trans-stilbene/3,3',4,5'-Tetrahydroxy-trans-stilbene/3,4,3',5'-Tetrahydroxy-trans-stilbene/4-[(E)-2-(3,5-Dihydroxyphenyl)vinyl]benzene-1,2-diol/3,5,3',4'-tetrahydroxystilbene/4-[(E)-2-(3,5-Dihydroxyphenyl)vinyl]-1,2-benzenediol/Piceatannol/4-[(E)-2-(3,5-dihydroxyphenyl)ethenyl]benzene-1,2-diol/4-(2-(3,5-Dihydroxyphenyl)vinyl)-1,2-benzenediol/(E)-4-[2-(3,5Dihydroxyphenyl)ethenyl]1,2-benzenediol/(E)-4-(3,5-Dihydroxystyryl)benzene-1,2-diol/5-[(E)-2-(3,4-Dihydroxyphenyl)vinyl]benzene-1,3-diol/trans-3,3',4,5'-tetrahydroxystilbene/3,3',4,5'-tetrahydroxystilbene/Piceatannol, (E)-

IUPAC Name

4-[(E)-2-(3,5-dihydroxyphenyl)ethenyl]benzene-1,2-diol

Applications

Piceatannol is a selective inhibitor of protein tyrosine kinase Syk. It could inhibit ICa,L, Ito, IKr, Ca2+ transients and Na+-Ca2+ exchange except IK1. Shows multiple biological activities such as anti-inflammatory, antiproliferative and immunomodulatory effects.In vitro: The treatment of human myeloid cells with piceatannol suppressed TNF-induced DNA binding activity of NF-κB. The effect of piceatannol was not restricted to myeloid cells, as TNF-induced NF-κB activation was also suppressed in lymphocyte and epithelial cells. Piceatannol also inhibited NF-κB activated by H2O2, PMA, LPS, okadaic acid, and ceramide. [1]

Density

1.5±0.1 g/cm3

Solubility

Methanol/H2O: 0.5 mg/mL

Flash Point

252.2±21.4 °C

Boiling Point

507.3±38.0 °C at 760 mmHg

Melting Point

223-227ºC

InChl

InChI=1S/C14H12O4/c15-11-5-10(6-12(16)8-11)2-1-9-3-4-13(17)14(18)7-9/h1-8,15-18H/b2-1+

InChl Key

CDRPUGZCRXZLFL-OWOJBTEDSA-N

WGK Germany

RID/ADR

HS Code Reference

2907290000

Personal Projective Equipment

Correct Usage

For Reference Standard and R&D, Not for Human Use Directly.

Meta Tag

provides coniferyl ferulate(CAS#:10083-24-6) MSDS, density, melting point, boiling point, structure, formula, molecular weight etc. Articles of coniferyl ferulate are included as well.>> amp version: coniferyl ferulate

No Technical Documents Available For This Product.

PMID

30173053

Abstract

Piceatannol, a natural derivative of resveratrol, has been shown to exert similar anti-oxidant and anti-inflammatory effects as resveratrol. However, it remains unknown whether piceatannol has hepatoprotective effect against acute liver injury. In this study, we investigated the in vivo effect of piceatannol on D-GalN/LPS-induced fulminant hepatic failure (FHF), and its in vitro effect on ER stress-inducing drug thapsigargin (TG)-induced proinflammatory cytokines production and ROS release. Our results indicated that piceatannol markedly decreased the mortality rate, reduced the serum levels of alanine transaminase and aspartic aminotransferase, ameliorated the liver damage induced by D-GalN/LPS in mice. In addition, piceatannol reduced the expression of proinflammatory cytokines, including TNF-α, IL-1β and IL-6, the expression of ER stress markers CHOP and phosphorylated-IRE1α, and the generation of oxidative stress in D-GalN/LPS-treated mouse liver. In vitro results were consistent with in vivo observations, demonstrating that piceatannol suppressed the secretion of proinflammatory cytokines, inflammasome activation and the production of ROS induced by TG with or without LPS priming in J774A.1 macrophages. Our study proposes piceatannol as a promising medication for preventing acute liver failure and the mechanisms may be related to its inhibitory effects on ER stress, inflammation and oxidative stress.

Copyright © 2018 Elsevier B.V. All rights reserved.

KEYWORDS

ER stress; Fulminant hepatic failure; Inflammation; Oxidative stress; Piceatannol

Title

Piceatannol attenuates D-GalN/LPS-induced hepatoxicity in mice: Involvement of ER stress, inflammation and oxidative stress.

Author

Wen J1, Lin H1, Zhao M1, Tao L1, Yang Y1, Xu X1, Jia A1, Zhang J1, Weng D2.

Publish date

2018 Nov

PMID

30175773

Abstract

Piceatannol, a naturally occurring stilbene derivative mainly found in grapes, possesses apoptotic activity in various cancer cell lines, in addition to potent antioxidant activity. In the current study, we showed that piceatannol exhibits potent cytotoxic effects in all tested leukemia cell lines (THP-1, HL-60, U937, and K562). These effects were accompanied by induction of DNA damage, an increase in the proportion of cells in the sub-G1 phase of the cell cycle, and inhibition of reactive oxygen species (ROS) generation. However, N-acetyl-L-cysteine (NAC), a strong ROS scavenger, significantly inhibited piceatannol-induced apoptosis, suggesting that piceatannol-induced apoptosis does not occur via inhibition of ROS generation. Piceatannol also resulted in a significant increase in mitochondrial depolarization, along with a decline in Bcl-2 expression, which was not restored by NAC. Conversely, ectopic Bcl-2 overexpression moderately inhibited piceatannol-induced apoptosis. Furthermore, piceatannol strongly inhibited X-linked inhibitor of apoptosis protein (XIAP) expression, which was restored by NAC. A transient knockdown of XIAP significantly increased piceatannol-induced apoptosis in the presence of NAC, suggesting that XIAP downregulation increases piceatannol-induced apoptosis, and that NAC could reverse this effect by increasing XIAP expression. Taken together, these results suggest that piceatannol induces apoptosis in human leukemia cell lines by downregulating XIAP expression, regardless of antioxidant activity.

KEYWORDS

B-cell lymphoma 2; N-acetyl-L-cysteine; X-linked inhibitor of apoptosis protein; apoptosis; piceatannol

Title

Piceatannol-Induced Apoptosis Is Reversed by N-Acetyl-L-cysteine through Restoration of XIAP Expression.

Author

Jin CY1, Molagoda IMN2, Park C3, Kwon TK4, Yun SJ5, Kim WJ5, Kim GY2, Choi YH6.

Publish date

2018

PMID

29057795

Abstract

Animal studies have shown the beneficial effects of piceatannol on metabolic health; however, there is a lack of human studies designed to examine these effects. The objective of this study was to investigate the effects of piceatannol on metabolic health in humans. This randomized, placebo-controlled study was conducted on 39 subjects, including 10 overweight men and 9 overweight women (BMI ≥ 25), as well as 10 non-overweight men and 10 non-overweight women (BMI < 25). Subjects received piceatannol (20 mg/day) or placebo capsules for eight weeks in a random order. The primary outcome was the effect of piceatannol on glucose-metabolism, including insulin sensitivity. The secondary outcomes were the effects on other parameters, including blood pressure (BP), heart rate (HR), endothelial function, lipids, inflammation, oxidative stress, mood status, and Sirt1 and phospho-AMP-activated kinase (p-AMPK) expression in isolated peripheral blood mononuclear cells (PBMNCs). Supplementation with piceatannol in overweight men reduced serum insulin levels, HOMA-IR, BP and HR. Other groups, including non-overweight men, as well as overweight and non-overweight women, showed no beneficial effects on insulin sensitivity, BP and HR. Furthermore, piceatannol is not associated with other data, including body weight (BW), body composition, endothelial function, lipids, inflammation, oxidative stress, mood status, and Sirt1/p-AMPK expression in PBMNCs. In conclusion, supplementation with piceatannol can improve metabolic health, including insulin sensitivity, BP and HR, in overweight men.

KEYWORDS

an analogue of resveratrol; insulin sensitivity; metabolic health; piceatannol

Title

The Effect of Piceatannol from Passion Fruit (Passiflora edulis) Seeds on Metabolic Health in Humans.

Author

Kitada M1,2, Ogura Y3, Maruki-Uchida H4, Sai M5, Suzuki T6, Kanasaki K7,8, Hara Y9, Seto H10, Kuroshima Y11, Monno I12, Koya D13,14.

Publish date

2017 Oct 18