Art. -Nr.: HY-126066

(-)-Syringaresinol

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(-)-Syringaresinol is an orally active isomer of syringaresinol (HY-N8307) found in Annona Montana. (-)-Syringaresinol exhibits antioxidant, anti-inflammatory, and anticancer activities. (-)-Syringaresinol can alleviate ulcerative colitis via the PI3K-Akt/MAPK/Wnt signaling pathway. (-)-Syringaresinol inhibits HL-60 cell proliferation by arresting the G1 phase and inducing apoptosis. (-)-Syringaresinol inhibits LPS (HY-D1056)-induced microglial activation by downregulating the NF-κB p65 signaling pathway and its interaction with ERβ, exerting anti-neuroinflammatory effects.

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Reinheit: 99.93%
CAS. Nr.: 6216-81-5
Formel: C₂₂H₂₆O₈
Molecular Weight:418.44

Speicherung:

4°C, protect from light

* In solvent : -80°C, 6 months; -20°C, 1 month (protect from light)

(-)-Syringaresinol Chemical Structure

CAS. Nr.: 6216-81-5

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Biologische Aktivität
- Beschreibung
- Cellular Effect
- In Vitro
- In Vivo
Chemical Information
Lösungsmittel & Löslichkeit
- In Vitro
- In Vivo
Reinheit & Dokumentation
Verweise
Help & FAQs
Classifications
Bioz

Biologische Aktivität

Beschreibung

Alle NF-κB Isoform-spezifische Produkte anzeigen :

Alle NO Synthase Isoform-spezifische Produkte anzeigen :

Alle TNF Receptor Isoform-spezifische Produkte anzeigen :

Alle Interleukin Related Isoform-spezifische Produkte anzeigen :

Alle COX Isoform-spezifische Produkte anzeigen :

Alle CDK Isoform-spezifische Produkte anzeigen :

Alle Bcl-2 Family Isoform-spezifische Produkte anzeigen :

Alle Akt Isoform-spezifische Produkte anzeigen :

Alle p38 MAPK Isoform-spezifische Produkte anzeigen :

Alle GSK-3 Isoform-spezifische Produkte anzeigen :

Cellular Effect

Cell Line	Type	Value	Description	References
A549	IC₅₀	>30 μM Compound: 7	Anticancer activity against human A549 cells by SRB assay Anticancer activity against human A549 cells by SRB assay	[PMID: 21420296]
BV-2	IC₅₀	>100 μM Compound: 17	Antineuroinflammatory activity in mouse BV2 cells assessed as inhibition of LPS-induced NO production after 24 hrs in presence of LPS by Griess reaction based assay Antineuroinflammatory activity in mouse BV2 cells assessed as inhibition of LPS-induced NO production after 24 hrs in presence of LPS by Griess reaction based assay	[PMID: 28911817]
BV-2	IC₅₀	13.48 μM Compound: 7	Antiinflammatory activity in mouse BV2 cells assessed as inhibition of lipopolysaccharide induced NO production Antiinflammatory activity in mouse BV2 cells assessed as inhibition of lipopolysaccharide induced NO production	[PMID: 21420296]
BV-2	IC₅₀	27.53 μM Compound: 5; Syringaresinol	Antineuroinflammatory activity in mouse BV2 cells assessed as inhibition of LPS-induced nitric oxide production after 24 hrs by Griess assay Antineuroinflammatory activity in mouse BV2 cells assessed as inhibition of LPS-induced nitric oxide production after 24 hrs by Griess assay	[PMID: 26774654]
Neutrophil	IC₅₀	>50 μM Compound: (-)-syringaresinol	Antiinflammatory activity in human neutrophils assessed as inhibition of fMLP/Cytochalasin B-induced elastase release Antiinflammatory activity in human neutrophils assessed as inhibition of fMLP/Cytochalasin B-induced elastase release	[PMID: 18817445]
Neutrophil	IC₅₀	>50 μM Compound: 25	Antiinflammatory activity in human neutrophils assessed as inhibition of formyl-L-methionyl-L-leucyl-L-phenylalanine/cytochalasin B-induced elastase release Antiinflammatory activity in human neutrophils assessed as inhibition of formyl-L-methionyl-L-leucyl-L-phenylalanine/cytochalasin B-induced elastase release	[PMID: 18211005]
Neutrophil	IC₅₀	39.87 μM Compound: 25	Antiinflammatory activity in human neutrophils assessed as inhibition of formyl-L-methionyl-L-leucyl-L-phenylalanine/cytochalasin B-induced superoxide anion generation Antiinflammatory activity in human neutrophils assessed as inhibition of formyl-L-methionyl-L-leucyl-L-phenylalanine/cytochalasin B-induced superoxide anion generation	[PMID: 18211005]
Neutrophil	IC₅₀	40.2 μM Compound: (-)-syringaresinol	Antiinflammatory activity in human neutrophils assessed as inhibition of fMLP/cytochalasin B-induced superoxide radical anion generation Antiinflammatory activity in human neutrophils assessed as inhibition of fMLP/cytochalasin B-induced superoxide radical anion generation	[PMID: 18817445]
RAW264.7	IC₅₀	>50 μM Compound: 9	Inhibition of LPS-induced IL-1beta production in mouse RAW264.7 cells after 24 hrs by ELISA Inhibition of LPS-induced IL-1beta production in mouse RAW264.7 cells after 24 hrs by ELISA	[PMID: 24963714]
RAW264.7	IC₅₀	45.6 μM Compound: 9	Inhibition of LPS-induced NO production in mouse RAW264.7 cells after 24 hrs by Griess reagent based assay Inhibition of LPS-induced NO production in mouse RAW264.7 cells after 24 hrs by Griess reagent based assay	[PMID: 24963714]
SK-MEL-2	IC₅₀	14.47 μM Compound: 7	Anticancer activity against human SK-MEL-2 cells by SRB assay Anticancer activity against human SK-MEL-2 cells by SRB assay	[PMID: 21420296]
SK-OV-3	IC₅₀	>30 μM Compound: 7	Anticancer activity against human SKOV3 cells by SRB assay Anticancer activity against human SKOV3 cells by SRB assay	[PMID: 21420296]
XF498	IC₅₀	8.82 μM Compound: 7	Anticancer activity against human XF498 cells by SRB assay Anticancer activity against human XF498 cells by SRB assay	[PMID: 21420296]

In Vitro

(-)-Syringaresinol (25-100 μM, 24 h) enhances intestinal epithelial barrier function, reduces levels of TNF-α, IL-6, IFN-γ, and COX-2, increases tight junction protein expression levels in LPS (HY-D1056)-induced Caco-2 cell^[1].
(-)-Syringaresinol (0.5-40 μM,24-72 h) reduces cell viability against HL-60 cells (IC₅₀ = 5.8 μM), and has weak cytotoxicity against SNU-1, SK-OV-3, LLC cells (IC₅₀ > 30 μM)^[2].
(-)-Syringaresinol (0-20 μM,0-24 h) induces apoptosis, G1 arrest and release of cytochrome c in HL-60 cells^[2].
(-)-Syringaresinol (0-200 μM, 24 h) does not exhibit toxic effects on BV2 cells^[3].
(-)-Syringaresinol (25-100 μM, 1 h) suppresses LPS-induced proinflammatory mediator production and upregulation of NO production on BV2 cells^[3].
(-)-Syringaresinol (25-100 μM, 24 h) increases the expression of M2 marker CD206, but suppressed the expression of M1 marker CD40 in LPS-stimulated BV2 cells^[3].
(-)-Syringaresinol (50 μM, 1 h) has anti-inflammatory effects by ERβ in LPS-stimulated BV2 cells^[3].

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

Immunofluorescence^[1]

Cell Line:

LPS-induced Caco-2 cell
Concentration:

25 μM, 50 μM, 100 μM
Incubation Time:

24 h
Result:

Increased expression levels of ZO-1, occludin, claudin-1, and E-cadherin.

Cell Cycle Analysis^[2]

Cell Line:

HL-60 cells
Concentration:

1 μM
Incubation Time:

0 h, 4 h, 8 h, 16 h, 24 h
Result:

Arrested in G1, did not change S phase, increased the expressions of p21waf1/cip1 and p27kip1, decreased the expressions of cyclin D1, cyclin D2, and cyclin E as well as cdk2, cdk4 and cdk6.

Apoptosis Analysis^[2]

Cell Line:

HL-60 cells
Concentration:

0 μM, 0.5 μM, 5 μM, 20 μM
Incubation Time:

24 h
Result:

Showed nuclear fragmentation and cell shrinkage, increased the expression of Bax and the ratio of Bax/Bcl-2, decreased the expressions of Bcl-2 and Bcl-XL.

Western Blot Analysis^[2]

Cell Line:

HL-60 cells
Concentration:

0 μM, 0.5 μM, 5 μM, 20 μM
Incubation Time:

24 h
Result:

Increased cleavage of caspase-9, caspase-3, and PARP.

RT-PCR^[3]

Cell Line:

BV2 cells
Concentration:

25 μM, 50 μM, 100 μM
Incubation Time:

1 h
Result:

Attenuated the LPS-induced transcription levels of proinflammatory mediator IL-6, IL-1β, TNF-α, iNOS, and COX-2.

ELISA Assay^[3]

Cell Line:

BV2 cells
Concentration:

25 μM, 50 μM, 100 μM
Incubation Time:

1 h
Result:

Downregulated LPS-induced TNF-α and IL-6 levels.

Western Blot Analysis^[3]

Cell Line:

BV2 cells
Concentration:

25 μM, 50 μM, 100 μM
Incubation Time:

1 h
Result:

Attenuated the LPS-induced COX-2 and iNOS protein expression.
Reduced the LPS-induced activation of NF-κB p65.

In Vivo

(-)-Syringaresinol (10-40 mg/kg, i.g., once a day, 10 days) attenuates inflammatory responses, reduces intestinal epithelial permeability by participating in the regulation of the PI3K-Akt/MAPK/Wnt signaling pathway in Dextran sodium sulfate (DSS) (HY-116282C)-induced UC mouse model^[1].
(-)-Syringaresinol (60 mg/kg, i.g., once a day, 2 days) reduces inflammatory responses and suppresses astrocytes activation in the hippocampal area and corpus callosum in LPS-stimulated mice model^[3].

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

Animal Model:

DSS-induced UC mouse model ^[1]
Dosage:

10 mg/kg, 20 mg/kg, 40 mg/kg,
Administration:

i.g., once a day, 10 days
Result:

Reduced weight loss and DAI scores, increased colon length and reduced colon damage, reduced spleen coefficient.
Reduced bacterial levels in the spleen and mesenteric lymph nodes, reduced serum TNF-α, IL-6, IFN-γ and COX-2 levels.
Showed lower epithelial damage, more intact colon tissue and lower inflammatory cell infiltration than the contorl group.
Improved colonic epithelial cell ultrastructure and gradually restored tight and gap junction integrity.
Reduced mRNA expression of Pdgfra, Tgfbr2, Il1r1, Cacna1d, Fn1, Lamc1, Col4a1, Col1a1, Srfp1, Wnt4, Fzd1, and Wnt5b, reduced phosphorylation levels of PI3K, Akt, NF-κB, MAPK, and GSK-3β, as well as β-catenin, increased expression of E-cadherin.

Animal Model:

LPS (100 mg/kg)-stimulated C57BL/6 mice (Male 8-12-week-old) model^[3]
Dosage:

60 mg/kg
Administration:

i.g., once a day, 2 days
Result:

Reduced the mRNA levels of IL-6, IL-1β, TNF-α, COX-2, and iNOS in the mouse hippocampal region.
Suppressed LPS-induced astrocytes activation in the hippocampal area and corpus callosum.

Chemical Information

CAS. Nr. 6216-81-5
Appearance Solid
Molecular Weight 418.44
Formel C₂₂H₂₆O₈
Color White to off-white
SMILES

OC1=C(OC)C=C([C@@H]2OC[C@]3([H])[C@@]2([H])CO[C@H]3C4=CC(OC)=C(O)C(OC)=C4)C=C1OC
Structure Classification
- Phenylpropanoids
- Lignans
- Phenols
- Polyphenols
Initial Source
Versand

Room temperature in continental US; may vary elsewhere.
Speicherung

4°C, protect from light

* In solvent : -80°C, 6 months; -20°C, 1 month (protect from light)

Lösungsmittel & Löslichkeit

In Vitro:

DMSO : 100 mg/mL (238.98 mM; Need ultrasonic; Hygroscopic DMSO has a significant impact on the solubility of product, please use newly opened DMSO)

View the Complete Stock Solution Preparation Table

Preparing Stock Solutions

View the Complete Stock Solution Preparation Table

Concentration Solvent Mass

1 mg

5 mg

10 mg

Concentration

Solvent

Mass

1 mM

2.3898 mL

11.9491 mL

23.8983 mL

5 mM

0.4780 mL

2.3898 mL

4.7797 mL

10 mM

0.2390 mL

1.1949 mL

2.3898 mL

Please refer to the solubility information to select the appropriate solvent. Once prepared, please aliquot and store the solution to prevent product inactivation from repeated freeze-thaw cycles.

Storage method and period of stock solution: -80°C, 6 months; -20°C, 1 month (protect from light). When stored at -80°C, please use it within 6 months. When stored at -20°C, please use it within 1 month.

Molaritätsrechner

Mass (g) = Concentration (mol/L) × Volume (L) × Molecular Weight (g/mol)

Mass Mass

Konzentration Konzentration

Volumen Volumen

Molecular Weight Molecular Weight

Verdünnungsrechner

Konzentration _{(Stammlösung)} × Volumen _{(Stammlösung)} = Konzentration _{(Ziellösung)} × Volumen _{(Ziellösung)}

Konzentration _{(Stammlösung)} Konzentration _{(Stammlösung)}

Volumen _{(Stammlösung)} Volumen _{(Stammlösung)}

Konzentration _{(Ziellösung)} Konzentration _{(Ziellösung)}

Volumen _{(Ziellösung)} Volumen _{(Ziellösung)}

In Vivo:

Select the appropriate dissolution method based on your experimental animal and administration route.

Stock Solution Working Solution

For the following dissolution methods, please ensure to first prepare a clear stock solution using an In Vitro approach and then sequentially add co-solvents:
To ensure reliable experimental results, the clarified stock solution can be appropriately stored based on storage conditions. As for the working solution for In Vivo experiments, it is recommended to prepare freshly and use it on the same day.
The percentages shown for the solvents indicate their volumetric ratio in the final prepared solution. If precipitation or phase separation occurs during preparation, heat and/or sonication can be used to aid dissolution.

Protocol 1

Add each solvent one by one: 10% DMSO 40% PEG300 5% Tween-80 45% Saline

Solubility: ≥ 2.5 mg/mL (5.97 mM); Clear solution

This protocol yields a clear solution of ≥ 2.5 mg/mL (saturation unknown).

Taking 1 mL working solution as an example, add 100 μL DMSO stock solution (25.0 mg/mL) to 400 μL PEG300, and mix evenly; then add 50 μL Tween-80 and mix evenly; then add 450 μL Saline to adjust the volume to 1 mL.

Protocol 2

Add each solvent one by one: 10% DMSO 90% (20% SBE-β-CD in Saline)

Solubility: ≥ 2.5 mg/mL (5.97 mM); Clear solution

This protocol yields a clear solution of ≥ 2.5 mg/mL (saturation unknown).

Taking 1 mL working solution as an example, add 100 μL DMSO stock solution (25.0 mg/mL) to 900 μL 20% SBE-β-CD in Saline, and mix evenly.

Protocol 3

Add each solvent one by one: 10% DMSO 90% Corn Oil

Solubility: ≥ 2.5 mg/mL (5.97 mM); Clear solution

This protocol yields a clear solution of ≥ 2.5 mg/mL (saturation unknown). If the continuous dosing period exceeds half a month, please choose this protocol carefully.

Taking 1 mL working solution as an example, add 100 μL DMSO stock solution (25.0 mg/mL) to 900 μL Corn oil, and mix evenly.

In Vivo Dissolution Calculator

Please enter the basic information of animal experiments:

Dosage Dosage
mg/kg
Animal Weight (Per Animal) Animal Weight (Per Animal)
g
Dosing Volume (Per Animal) Dosing Volume (Per Animal)
μL
Number of Animals Number of Animals

Recommended: Prepare an additional quantity of animals to account for potential losses during experiments.

Recommended: Prepare an additional quantity of animals to account for potential losses during experiments.

Please enter your animal formula composition:

%
DMSO +

Recommended: Keep the proportion of DMSO in working solution below 2% if your animal is weak.
%
+
+
%
Tween-80 + +
%
Saline +

The co-solvents required include: DMSO, . All of co-solvents are available by MedChemExpress (MCE). , Tween 80. All of co-solvents are available by MedChemExpress (MCE).

Working solution concentration: 0.22 mg/mL

Reinheit & Dokumentation

Select Batch:

Reinheit: 99.98%

Assay: 99.98%

ee.: 99.98%

Data Sheet (290 KB)
SDS (252 KB)
- English - EN (252 KB)
- Français - FR (252 KB)
- Deutsch - DE (252 KB)
- Norwegian - NO (252 KB)
- Español - ES (252 KB)
- Swedish - SV (252 KB)
- Italian - IT (252 KB)
- Korean - KR (252 KB)
- Portuguese - PT (252 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)

Verweise

[1]. Liu Y, et al. (-)-Syringaresinol attenuates ulcerative colitis by improving intestinal epithelial barrier function and inhibiting inflammatory responses. Phytomedicine. 2024 Feb;124:155292. [Content Brief]

[2]. Park BY, et al. (-)-Syringaresinol inhibits proliferation of human promyelocytic HL-60 leukemia cells via G1 arrest and apoptosis. Int Immunopharmacol. 2008 Jul;8(7):967-73. [Content Brief]

[3]. Zhang L, et al. (-)-Syringaresinol suppressed LPS-induced microglia activation via downregulation of NF-κB p65 signaling and interaction with ERβ. Int Immunopharmacol. 2021 Oct;99:107986. [Content Brief]

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.

Complete Stock Solution Preparation Table

Optional Solvent	Concentration Solvent Mass	1 mg	5 mg	10 mg	25 mg
DMSO	1 mM	2.3898 mL	11.9491 mL	23.8983 mL	59.7457 mL
	5 mM	0.4780 mL	2.3898 mL	4.7797 mL	11.9491 mL
	10 mM	0.2390 mL	1.1949 mL	2.3898 mL	5.9746 mL
	15 mM	0.1593 mL	0.7966 mL	1.5932 mL	3.9830 mL
	20 mM	0.1195 mL	0.5975 mL	1.1949 mL	2.9873 mL
	25 mM	0.0956 mL	0.4780 mL	0.9559 mL	2.3898 mL
	30 mM	0.0797 mL	0.3983 mL	0.7966 mL	1.9915 mL
	40 mM	0.0597 mL	0.2987 mL	0.5975 mL	1.4936 mL
	50 mM	0.0478 mL	0.2390 mL	0.4780 mL	1.1949 mL
	60 mM	0.0398 mL	0.1992 mL	0.3983 mL	0.9958 mL
	80 mM	0.0299 mL	0.1494 mL	0.2987 mL	0.7468 mL
	100 mM	0.0239 mL	0.1195 mL	0.2390 mL	0.5975 mL

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(-)-Syringaresinol

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