2. Others NF-κB Immunology/Inflammation Apoptosis Cell Cycle/DNA Damage PI3K/Akt/mTOR MAPK/ERK Pathway Stem Cell/Wnt
  3. Drug Isomer NF-κB NO Synthase TNF Receptor Interleukin Related IFNAR COX CD20 CDK Bcl-2 Family Apoptosis Akt p38 MAPK GSK-3
  4. (-)-Syringaresinol

(-)-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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(-)-Syringaresinol Chemical Structure

(-)-Syringaresinol Chemical Structure

CAS No. : 6216-81-5

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Based on 1 publication(s) in Google Scholar

Other Forms of (-)-Syringaresinol:

(-)-Syringaresinol Related Antibodies

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nNOS iNOS eNOS

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TNFRSF1A/CD120a TNFRSF4 TNFRSF5/CD40 TNFRSF6/Fas/CD95 TNFRSF7/CD27 TNFRSF8/CD30 TNFRSF9/4-1BB/CD137 TNFRSF12A/TWEAK TNFRSF16/NGF Receptor/CD271 TNFRSF18/GITR/CD357

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IL-1 IL-2 IL-3 IL-4 IL-5 IL-6 IL-8 IL-10 IL-12 IL-13 IL-15 IL-17 IL-23 IL-7 IL-33 IL-22

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COX COX-1 COX-2 COX-3

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CDK1 CDK2 CDK3 CDK4 CDK5 CDK6 CDK7 CDK8 CDK9 CDK11 CDK12 CDK13 CDK14 CDK16 CDK19 CDC CLK Pho85 CDK10 CDK15 CDK17 CDK18 CDK20 PITSLRE

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Bcl-2 Bcl-xL Bcl-W Mcl-1 Bfl-1 Bcl-B Bax Bak Bim BNIP3

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  • Biological Activity

  • Purity & Documentation

  • References

  • Customer Review

Description

(-)-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[1][2][3].

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
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]
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.

(-)-Syringaresinol Related Antibodies

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.
Molecular Weight

418.44

Formula

C22H26O8
CAS No.
Appearance

Solid

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
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.
Solvent & Solubility
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)

Preparing
Stock Solutions
Concentration Solvent Mass 1 mg 5 mg 10 mg
1 mM 2.3898 mL 11.9491 mL 23.8983 mL
5 mM 0.4780 mL 2.3898 mL 4.7797 mL
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In Vivo:

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

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.

    Preparation of Saline: Dissolve 0.9 g sodium chloride in ddH₂O and dilute to 100 mL to obtain a clear Saline solution.
  • 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.

    Preparation of 20% SBE-β-CD in Saline (4°C, storage for one week): 2 g SBE-β-CD powder is dissolved in 10 mL Saline, completely dissolve until clear.
In Vivo Dissolution Calculator
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Method for preparing stock solution: mg drug dissolved in μL  DMSO (Stock solution concentration: mg/mL).
The concentration of the stock solution you require exceeds the measured solubility. The following solution is for reference only. If necessary, please contact MedChemExpress (MCE).
Method for preparing in vivo working solution for animal experiments: Take μL DMSO stock solution, add μL . μL , mix evenly, next add μL Tween 80, mix evenly, then add μL Saline.
 If the continuous dosing period exceeds half a month, please choose this protocol carefully.
Please ensure that the stock solution in the first step is dissolved to a clear state, and add co-solvents in sequence. You can use ultrasonic heating (ultrasonic cleaner, recommended frequency 20-40 kHz), vortexing, etc. to assist dissolution.
Purity & Documentation

Purity: 99.95%

SDS (252 KB)

COA (258 KB) HNMR (203 KB) CNMR (160 KB) RP-HPLC (327 KB) MS (601 KB)

Handling Instructions (2659 KB)
References

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 Related Classifications

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    Species cross-reactivity must be investigated individually for each product. Many human cytokines will produce a nice response in mouse cell lines, and many mouse proteins will show activity on human cells. Other proteins may have a lower specific activity when used in the opposite species.

Keywords:

(-)-Syringaresinol6216-81-5Drug IsomerNF-κBNO SynthaseTNF ReceptorInterleukin RelatedIFNARCOXCD20CDKBcl-2 FamilyApoptosisAktp38 MAPKGSK-3Nuclear factor-κBNuclear factor-kappaBNitric oxide synthasesNOSTumor Necrosis Factor ReceptorTNFRILInterferon-α/β receptorInterferon-alpha/beta receptor CyclooxygenaseCyclin dependent kinasePKBProtein kinase BGlycogen synthase kinase-3Glycogen synthase kinase 3Antioxidantanti-inflammatoryanticancerHL-60 cellsapoptosisBV2 cellsDSSUC mouse modelInhibitorinhibitorinhibit

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