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Trimethoxystilbene

CAS# 22255-22-7

Trimethoxystilbene

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Quality Control of Trimethoxystilbene

Number of papers citing our products

Chemical structure

Trimethoxystilbene

3D structure

Chemical Properties of Trimethoxystilbene

Cas No. 22255-22-7 SDF Download SDF
PubChem ID 5388063 Appearance Powder
Formula C17H18O3 M.Wt 270.3
Type of Compound Polyphenols Storage Desiccate at -20°C
Synonyms 3,4',5-Trimethoxystilbene
Solubility DMSO : ≥ 50 mg/mL (184.97 mM)
H2O : < 0.1 mg/mL (insoluble)
*"≥" means soluble, but saturation unknown.
Chemical Name 1,3-dimethoxy-5-[(E)-2-(4-methoxyphenyl)ethenyl]benzene
SMILES COC1=CC=C(C=C1)C=CC2=CC(=CC(=C2)OC)OC
Standard InChIKey GDHNBPHYVRHYCC-SNAWJCMRSA-N
Standard InChI InChI=1S/C17H18O3/c1-18-15-8-6-13(7-9-15)4-5-14-10-16(19-2)12-17(11-14)20-3/h4-12H,1-3H3/b5-4+
General tips For obtaining a higher solubility , please warm the tube at 37 ℃ and shake it in the ultrasonic bath for a while.Stock solution can be stored below -20℃ for several months.
We recommend that you prepare and use the solution on the same day. However, if the test schedule requires, the stock solutions can be prepared in advance, and the stock solution must be sealed and stored below -20℃. In general, the stock solution can be kept for several months.
Before use, we recommend that you leave the vial at room temperature for at least an hour before opening it.
About Packaging 1. The packaging of the product may be reversed during transportation, cause the high purity compounds to adhere to the neck or cap of the vial.Take the vail out of its packaging and shake gently until the compounds fall to the bottom of the vial.
2. For liquid products, please centrifuge at 500xg to gather the liquid to the bottom of the vial.
3. Try to avoid loss or contamination during the experiment.
Shipping Condition Packaging according to customer requirements(5mg, 10mg, 20mg and more). Ship via FedEx, DHL, UPS, EMS or other couriers with RT, or blue ice upon request.

Source of Trimethoxystilbene

The herbs of Sophora viciifolia

Biological Activity of Trimethoxystilbene

Description3,4',5-Trimethoxystilbene, an inhibitor of tubulin polymerization, which exerts antitumor, anti-HCV, antiallergic, anti-mitotic properties, it also exerts antiangiogenic and vascular-disrupting effects in zebrafish through the downregulation of VEGFR2 and cell-cycle modulation. 3,4',5-Trimethoxystilbene has anti-inflammatory activity, the ability of it to induce HO-1 expression may provide one of possible mechanisms of its anti-inflammatory action.
TargetsHCV | AMPK | mTOR | Calcium Channel | TNF-α | HO-1 | IL Receptor | VEGFR | HCV
In vitro

Structural modification of resveratrol leads to increased anti-tumor activity, but causes profound changes in the mode of action.[Pubmed: 26044878 ]

Toxicol Appl Pharmacol. 2015 Aug 15;287(1):67-76.

(Z)-3,5,4'-Trimethoxystilbene (3,4',5-Trimethoxystilbene, Z-TMS) is a resveratrol analog with increased antiproliferative activity towards a number of cancer cell lines compared to resveratrol, which has been shown to inhibit tubulin polymerization in vitro. The purpose of this study was to investigate if Z-TMS still shows potential for the prevention of metabolic diseases as known for resveratrol.
METHODS AND RESULTS:
Cell growth inhibition was determined with IC50 values for Z-TMS between 0.115μM and 0.473μM (resveratrol: 110.7μM to 190.2μM). Flow cytometric analysis revealed a G2/M arrest after Z-TMS treatment, whereas resveratrol caused S phase arrest. Furthermore, Z-TMS was shown to impair microtubule polymerization. Beneficial effects on lipid accumulation were observed for resveratrol, but not for Z-TMS in an in vitro steatosis model. (E)-Resveratrol was confirmed to elevate cAMP levels, and knockdown of AMPK attenuated the antiproliferative activity, while Z-TMS did not show significant effects in these experiments. SIRT1 and AMPK activities were further measured indirectly via induction of the target gene small heterodimer partner (SHP). Thereby, (E)-resveratrol, but not Z-TMS, showed potent induction of SHP mRNA levels in an AMPK- and SIRT1-dependent manner, as confirmed by knockdown experiments. We provide evidence that Z-TMS does not show beneficial metabolic effects, probably due to loss of activity towards resveratrol target genes. Moreover, our data support previous findings that Z-TMS acts as an inhibitor of tubulin polymerization.
CONCLUSIONS:
These findings confirm that the methylation of resveratrol leads to profound changes in the mode of action, which should be taken into consideration when conducting lead structure optimization approaches.

Differential effects of resveratrol and its natural analogs, piceatannol and 3,5,4'-trans-trimethoxystilbene, on anti-inflammatory heme oxigenase-1 expression in RAW264.7 macrophages.[Pubmed: 23861314 ]

Biofactors. 2014 Jan-Feb;40(1):138-45.


METHODS AND RESULTS:
Resveratrol (Res) and its two natural analogs that are also related to Res metabolism, piceatannol (Pic) and 3,5,4'-trans-trimethoxystilbene (3,4',5-Trimethoxystilbene ,TMS), were compared in their ability to suppress lipopolysaccharide (LPS)-induced production of proinflammatory tumor necrosis factor-α (TNF-α) and interleukin-1β (IL-1β) and to induce anti-inflammatory heme oxygenase-1 (HO-1) expression in RAW264.7 macrophages. At non-cytotoxic concentrations, they differentially suppressed LPS-induced production of TNF-α and IL-1β; the relative potency for suppression of TNF-α and IL-1β production was Pic > Res > TMS. Res and Pic differentially induced HO-1 expression; Pic, which possesses four hydroxyl groups, was more active in inducing HO-1 expression than Res that contains three hydroxyl groups. TMS, which has none of hydroxyl groups, failed to induce HO-1 expression. These findings suggest that the hydroxyl groups of Res analogs are important for suppression of TNF-α and IL-1β production and HO-1 expression. Interestingly, protoporphyrin-IX, a competitive inhibitor of HO-1 activity, partly attenuated the inhibitory effects of Res and Pic (but not TMS) on TNF-α and IL-1β production, suggesting that suppression of TNF-α and IL-1β production correlates at least in part with HO-1 expression.
CONCLUSIONS:
Overall, the ability of Res analogs to induce HO-1 expression may provide one of possible mechanisms of their anti-inflammatory action.

beta-Cyclodextrins influence on E-3,5,4'-trimethoxystilbene absorption across biological membrane model: a differential scanning calorimetry evidence.[Pubmed: 20045042 ]

Int J Pharm. 2010 Mar 30;388(1-2):144-50.

E-3,5,4'-trimethoxystilbene (TMS) is a naturally occurring analog of resveratrol. The anti-neoplastic, antiallergic and anti-angiogenic activities of TMS have been recently reported.
METHODS AND RESULTS:
From the viewpoint of metabolism, TMS may be more favourable than resveratrol because all of its hydroxyl groups, which are subjected to extensive glucuronide or sulphate conjugation in the metabolic pathways of resveratrol, are protected by methylation. Moreover, methylation increases lipophilicity and may enhance cell membrane permeability, but it decreases its solubility in aqueous media. A way to increase TMS solubility can be represented by complexation with beta-cyclodextrins. In the present paper, the differential scanning calorimetry technique has been used to study the interaction of TMS with a biomembrane model constituted by dimyristoylphosphatidylcholine multilamellar vesicles. Furthermore, kinetic experiments have been carried out to follow the uptake of TMS by biomembranes in the presence of beta-cyclodextrins to gain information on the effect of beta-cyclodextrins on the uptake process.
CONCLUSIONS:
Our results indicate that opportune concentrations of beta-cyclodextrins greatly improve the uptake of TMS by biomembrane models.

In vivo

(Z)-3,5,4'-Trimethoxystilbene Limits Hepatitis C and Cancer Pathophysiology by Blocking Microtubule Dynamics and Cell-Cycle Progression.[Pubmed: 27287718]

Cancer Res. 2016 Aug 15;76(16):4887-96.

Hepatocellular carcinoma (HCC) is the third most common cause of cancer-related deaths worldwide. Chronic hepatitis C virus (HCV) infection causes induction of several tumors/cancer stem cell (CSC) markers and is known to be a major risk factor for development of HCC. Therefore, drugs that simultaneously target viral replication and CSC properties are needed for a risk-free treatment of advanced stage liver diseases, including HCC.
METHODS AND RESULTS:
Here, we demonstrated that (Z)-3,5,4'-trimethoxystilbene (3,4',5-Trimethoxystilbene ,Z-TMS) exhibits potent antitumor and anti-HCV activities without exhibiting cytotoxicity to human hepatocytes in vitro or in mice livers. Diethylnitrosamine (DEN)/carbon tetrachloride (CCl4) extensively induced expression of DCLK1 (a CSC marker) in the livers of C57BL/6 mice following hepatic injury. Z-TMS exhibited hepatoprotective effects against DEN/CCl4-induced injury by reducing DCLK1 expression and improving histologic outcomes. The drug caused bundling of DCLK1 with microtubules and blocked cell-cycle progression at G2-M phase in hepatoma cells via downregulation of CDK1, induction of p21(cip1/waf1) expression, and inhibition of Akt (Ser(473)) phosphorylation. Z-TMS also inhibited proliferation of erlotinib-resistant lung adenocarcinoma cells (H1975) bearing the T790M EGFR mutation, most likely by promoting autophagy and nuclear fragmentation.
CONCLUSIONS:
In conclusion, Z-TMS appears to be a unique therapeutic agent targeting HCV and concurrently eliminating cells with neoplastic potential during chronic liver diseases, including HCC. It may also be a valuable drug for targeting drug-resistant carcinomas and cancers of the lungs, pancreas, colon, and intestine, in which DCLK1 is involved in tumorigenesis.

Protocol of Trimethoxystilbene

Kinase Assay

Novel role for TRPC4 in regulation of macroautophagy by a small molecule in vascular endothelial cells.[Pubmed: 25476892 ]

Biochim Biophys Acta. 2015 Feb;1853(2):377-87.

Macroautophagy (autophagy) is an important factor affecting the function of vascular endothelial cells (VECs) and must be tightly regulated in these cells. However, the precise mechanisms underlying this process, particularly in the presence of serum, remain obscure.
METHODS AND RESULTS:
In this study, we identified trans-3,5,4'-trimethoxystilbene (TMS) as a potent small molecule inducer of autophagy in human umbilical vascular endothelial cells (HUVECs) in the presence of serum. Using high-throughput DNA microarray and siRNA transfection technologies, we demonstrated that TMS induced autophagy by up-regulating the expression of the transient receptor potential canonical channel 4 (TRPC4), an important cation channel in HUVECs. In addition, the overexpression of TRPC4 by plasmid transfection also induced autophagy. Mechanistic studies revealed that the up-regulation of TRPC4 increased the intracellular Ca²⁺ concentration, which, in turn, activated the Ca²⁺/CaMKKβ/AMPK pathway, leading to mTOR inhibition and autophagy.
CONCLUSIONS:
Our study identifies a novel role for TRPC4 in the regulation of autophagy in VECs. TMS is a useful new tool for investigating the molecular mechanism of autophagy in VECs and may serve as a potential lead compound for developing a class of autophagy inducers to treat autophagy-related diseases.

Structure Identification
Biofactors. 2006;27(1-4):37-46.

Anti-mitotic properties of resveratrol analog (Z)-3,5,4'-trimethoxystilbene.[Pubmed: 17012762]


METHODS AND RESULTS:
(Z)-3,5,4'-Trimethoxystilbene(3,4',5-Trimethoxystilbene) is a natural polyphenol present in five different plants, Virola cuspidata, Virola elongata, Centipeda minima, Schoenus nigricans and Rheum undulatum. This molecule was prepared in a three-step sequence in good overall yield. The isomerisation from the (E)- to (Z)-isomer is performed using UV irradiation. Biological investigations were conducted on a human colon cancer cell line (Caco-2) with anti-mitotic activities. Growth was completely arrested at an added 0.4 microM level of (Z)-3,5,4'-trimethoxystilbene(3,4',5-Trimethoxystilbene).
CONCLUSIONS:
This agent is 100-fold more active than resveratrol or (E)-3,5,4'-trihydroxystilbene(3,4',5-Trimethoxystilbene), and the mechanism of this process involves an inhibition of tubulin polymerisation in a dose dependent manner.

Trimethoxystilbene Dilution Calculator

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Trimethoxystilbene Molarity Calculator

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Preparing Stock Solutions of Trimethoxystilbene

1 mg 5 mg 10 mg 20 mg 25 mg
1 mM 3.6996 mL 18.498 mL 36.9959 mL 73.9919 mL 92.4898 mL
5 mM 0.7399 mL 3.6996 mL 7.3992 mL 14.7984 mL 18.498 mL
10 mM 0.37 mL 1.8498 mL 3.6996 mL 7.3992 mL 9.249 mL
50 mM 0.074 mL 0.37 mL 0.7399 mL 1.4798 mL 1.8498 mL
100 mM 0.037 mL 0.185 mL 0.37 mL 0.7399 mL 0.9249 mL
* Note: If you are in the process of experiment, it's necessary to make the dilution ratios of the samples. The dilution data above is only for reference. Normally, it's can get a better solubility within lower of Concentrations.

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Background on Trimethoxystilbene

Trans-Trimethoxyresveratrol is a derivative of Resveratrol (RSV),and it may be a more potent anti-inflammatory, antiangiogenic and vascular-disrupting agent when compared with resveratrol. In vitro: The in vitro study of resveratrol and trans-Trimethoxyresveratrol showed rather weak cytotoxic effects on three cancer cell lines (HepG2, MCF-7, and MDA-MB-231), which contradicted a previous study reporting that resveratrol inhibited MCF-7 cells with an IC50 of about 10?μM. This discrepancy might be explained by the fact that the measurements were made 24?h after drug treatment, whereas the measurements of the previous study were taken 6 days after. The fact that the cytotoxic effect of trans-Trimethoxyresveratrol was lower than that of resveratrol is surprising, because in many studies, trans-Trimethoxyresveratrol is the most active analogue of resveratrol , although resveratrol shows much stronger antioxidant effects than that of trans-Trimethoxyresveratrol.[1] In vivo: Zebrafish embryos offer great advantage over their adults as well as other in vivo models because of the external development and optical transparency during their first few days, making them invaluable in the inspection of developmental processes. These unique advantages can even be made more useful when specific cell types are labeled with fluorescent probes. Zebrafish embryo in vivo, suggests that trans-Trimethoxyresveratrol has both more potent antiangiogenic activity and more importantly, stronger specific cytotoxic effects on endothelial cells than does resveratrol.[1]

References:
[1]. Alex, D. et al. Resveratrol derivative, trans-3,5,4'-trimethoxystilbene, exerts antiangiogenic and vascular-disrupting effects in zebrafish through the downregulation of VEGFR2 and cell-cycle modulation. Journal of cellular biochemistry 109, 339-346, doi:

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References on Trimethoxystilbene

The resveratrol analogue trimethoxystilbene inhibits cancer cell growth by inducing multipolar cell mitosis.[Pubmed:27739192]

Mol Carcinog. 2017 Mar;56(3):1117-1126.

Natural compounds are extensively studied for their potential use in traditional and non-traditional medicine. Several natural and synthetic Resveratrol analogues have shown interesting biological activities in the field of cancer chemoprevention. In the present study, we have focused on the ability of Resveratrol and two methoxylated derivatives (Trimethoxystilbene and Pterostilbene) to inhibit human cancer cell growth particularly analyzing their ability to interfere with tubulin dynamics at mitosis. We show that Trimethoxystilbene, differently from Resveratrol and Pterostilbene, alters microtubule polymerization dynamics in HeLa cells specifically inducing multipolar spindles and mitotic arrest coupled to a reduction of cell growth and an increase in apoptotic death by mitotic catastrophe. This work demonstrates that the structural modification of Rsv causes substantial changes in the mechanism of action of the derivatives. The presence of three extra methyl groups renders Trimethoxy very efficient in impairing cell proliferation by inducing mitotic catastrophe in cancer cells. (c) 2016 Wiley Periodicals, Inc.

Description

Trans-Trimethoxyresveratrol is a derivative of Resveratrol (RSV),and it may be a more potent anti-inflammatory, antiangiogenic and vascular-disrupting agent when compared with resveratrol.

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