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Cat. No.: HY-N3841A

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δ-Viniferin

δ-Viniferin is a COX-1/COX-2 inhibitor (with an IC₅₀ of 5 µM for both enzymes). δ-Viniferin induces the expression of SIRT1, catalase and HO-1, promotes the phosphorylation of eNOS, and stimulates nitric oxide (NO) production. δ-Viniferin is applicable to research related to atherosclerosis, downy mildew, Gram-positive bacterial infections, inflammation, infections, cardiovascular diseases and diabetes.

For research use only. We do not sell to patients.

CAS No.: 681293-15-2
Formula: C₂₈H₂₂O₆
Molecular Weight:454.47

Storage:

Please store the product under the recommended conditions in the Certificate of Analysis.

Data Sheet (285 KB)

δ-Viniferin Chemical Structure

CAS No.: 681293-15-2

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Use of MCE Products

Strong Fluorescence Signal / Multi-Disciplinary Applications / High Fluorescence Specificity

Biological Activity
- Description
- IC₅₀ & Target
- Cellular Effect
- In Vitro
- Parmacokinetics
Chemical Information
Purity & Documentation
References
Calculators
Help & FAQs
Classifications
Bioz

Biological Activity

Description

IC₅₀ & Target

^[2]^[1]^[3]

COX-1

5 μM (IC₅₀)

COX-2

5 μM (IC₅₀)

SIRT1

HO-1

eNOS

All COX Isoforms :

All Sirtuin Isoforms :

All Heme Oxygenase (HO) Isoforms :

HO-1
HO-2

All NO Synthase Isoforms :

Cellular Effect

Cell Line	Type	Value	Description	References
CCRF-CEM	IC₅₀	49 μM Compound: 4	Cytotoxicity against human CEM cells Cytotoxicity against human CEM cells	[PMID: 10650073]
HepG2	IC₅₀	48 μM Compound: 6	Cytotoxicity against human HepG2 cells after 3 days by microplate reader analysis Cytotoxicity against human HepG2 cells after 3 days by microplate reader analysis	[PMID: 32705864]
MCF-10A	IC₅₀	48 μM Compound: 6	Cytotoxicity against human MCF-10A cells after 3 days by microplate reader analysis Cytotoxicity against human MCF-10A cells after 3 days by microplate reader analysis	[PMID: 32705864]
RAW264.7	IC₅₀	80.2 μM Compound: 2a	Antiinflammatory activity in mouse RAW264.7 cells assessed as inhibition of LPS/IFNgamma-induced NO production by measuring NO level preincubated for 2 hrs and followed by LPS/IFNgamma addition and measured after 24 hrs by Griess assay Antiinflammatory activity in mouse RAW264.7 cells assessed as inhibition of LPS/IFNgamma-induced NO production by measuring NO level preincubated for 2 hrs and followed by LPS/IFNgamma addition and measured after 24 hrs by Griess assay	[PMID: 31350127]

In Vitro

δ-Viniferin (5 μM; 24 h) promotes wound repair in porcine aortic vascular endothelial cells and increases nitric oxide production in these cells at a concentration of 5 μM^[1].
δ-Viniferin (5 μM; 24 h) induces phosphorylation of endothelial nitric oxide synthase in a time-dependent manner and upregulates the expression of SIRT1, HO-1, and catalase in porcine aortic endothelial cells at a concentration of 5 μM^[1].
δ-Viniferin (5-10 μM; 24 h) protects porcine aortic vascular endothelial cells against H₂O₂-induced reduction in cell viability at a concentration of 5 μM^[1].
δ-Viniferin (5 μM) inhibits the activities of cyclooxygenase-1 and cyclooxygenase-2, with an IC₅₀ of 5 μM^[3].

MedChemExpress (MCE) has not independently confirmed the accuracy of these methods. They are for reference only.

Cell Migration Assay ^[1]

Cell Line:

porcine aortic vascular endothelial cells (VECs)
Concentration:

5, 10, 20 μM
Incubation Time:

24 h
Result:

Stimulated VEC wound repair significantly at 5 μM.
Did not produce a significant stimulatory effect.

Western Blot Analysis^[1]

Cell Line:

porcine aortic vascular endothelial cells (VECs)
Concentration:

5 μM
Incubation Time:

6, 12, 24 h (phos-eNOS, SIRT1, HO-1 analysis); 1, 3, 6, 12, 24 h (catalase analysis)
Result:

Induced phosphorylation of eNOS and increased expression of SIRT1 and HO-1 over 6, 12, and 24 hours.
Increased catalase protein expression in a time-dependent manner, with a significant 3-fold increase observed after 24 hours.

Cell Viability Assay^[1]

Cell Line:

porcine aortic vascular endothelial cells (VECs)
Concentration:

5, 10 μM
Incubation Time:

24 h
Result:

Reversed the reduction in cell viability caused by H₂O₂ exposure significantly at 5 μM.

Parmacokinetics

Species	Dose	Route	AUC_0-t	AUC_0-∞	MRT_0-t	MRT_0-∞	T_1/2β	T_max	V_z/F	CL_z/F	C_max	Bioavailability
Rat^[5]	70 mg/kg	p.o.	1162.0 μg/L·h	1181.9 μg/L·h	5.6 h	6.0 h	4.2 h	1.7 h	379.7 L/kg	60.6 L/h/kg	399.0 μg/L	2.3 %
Rat^[5]	1.37 mg/kg	i.v.	1004.7 μg/L·h	1017.6 μg/L·h	1.5 h	2.0 h	5.8 h	0.03 h	12.2 L/kg	1.4 L/h/kg	7611.7 μg/L	/

Chemical Information

CAS No. 681293-15-2
Molecular Weight 454.47
Formula C₂₈H₂₂O₆
SMILES

OC1=CC(O)=CC(/C=C/C2=CC=C3O[C@H](C4=CC=C(C=C4)O)[C@@H](C5=CC(O)=CC(O)=C5)C3=C2)=C1
Structure Classification
- Phenols
- Polyphenols
Initial Source
Shipping

Room temperature in continental US; may vary elsewhere.
Storage

Please store the product under the recommended conditions in the Certificate of Analysis.

Purity & Documentation

Select Batch:

Purity: 99.98%

Assay: 99.98%

ee.: 99.98%

Data Sheet (285 KB)
COA (2659 KB)
Elemental Analysis Report (2659 KB)
HNMR (2659 KB)
CNMR (2659 KB)
RP-HPLC (2659 KB)
NP-HPLC (2659 KB)
MS (2659 KB)
LCMS (2659 KB)
IR (2659 KB)
GC (2659 KB)
OR (2659 KB)
SDS-PAGE (2659 KB)
SEC-HPLC (2659 KB)
Other Report (2659 KB)
Handling Instructions (2659 KB)

References

[1]. Wu CW, et al. Resveratrol and its dimers ε-viniferin and δ-viniferin in red wine protect vascular endothelial cells by a similar mechanism with different potency and efficacy. The Kaohsiung journal of medical sciences. 2020 Jul;36(7):535-542.

[2]. Pezet R, et al. Delta-viniferin, a resveratrol dehydrodimer: one of the major stilbenes synthesized by stressed grapevine leaves. Journal of agricultural and food chemistry. 2003 Aug 27;51(18):5488-92. [Content Brief]

[3]. Vitrac X, et al. Determination of stilbenes (delta-viniferin, trans-astringin, trans-piceid, cis- and trans-resveratrol, epsilon-viniferin) in Brazilian wines. Journal of agricultural and food chemistry. 2005 Jul 13;53(14):5664-9.

[4]. Mattio LM, et al. Synthesis and Antimicrobial Activity of δ-Viniferin Analogues and Isosteres. Molecules (Basel, Switzerland). 2021 Dec 15;26(24):7594.

[5]. Mao P, et al. Pharmacokinetics, bioavailability, metabolism and excretion of δ-viniferin in rats. Acta pharmaceutica Sinica. B. 2016 May;6(3):243-52.

Calculators

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Help & FAQs

How should lyophilized recombinant proteins be reconstituted and stored?

1. Before opening the cap, centrifuge the vial at 13000 rpm for 20-30 seconds. This step will ensure that any lyophilized powder that may have adhered to the cap or walls is collected at the bottom of the vial, minimizing the risk of product loss.

Bioz

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Biological Activity
- Description
- IC₅₀ & Target
- In Vitro
Chemical Information
Purity & Documentation
References

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δ-Viniferin

All COX Isoforms

All Sirtuin Isoforms

All Heme Oxygenase (HO) Isoforms

All NO Synthase Isoforms