Immunology/Inflammation Neuronal Signaling Membrane Transporter/Ion Channel Stem Cell/Wnt TGF-beta/Smad Cytoskeleton PI3K/Akt/mTOR Apoptosis Anti-infection NF-κB Metabolic Enzyme/Protease Autophagy
NO Synthase PGE synthase TRP Channel CaMK Calmodulin TGF-beta/Smad Collagen Interleukin Related Akt TNF Receptor Caspase Bacterial Fungal Reactive Oxygen Species (ROS) Apoptosis Autophagy
Oxoglaucine

Referencia número: HY-N2595

Oxoglaucine

(Synonyms: O-Methylatheroline)

Oxoglaucine (O-Methylatheroline) is a natural product with multiple activities including autophagy activation, anti-inflammation, antibacterial activity, and immunoregulation. Oxoglaucine inhibits the TRPV5/calmodulin/CAMK-II pathway, suppresses TGFβ-induced Smad2 phosphorylation by upregulating Smad7, blocks Ca²⁺ influx, activates autophagy, alleviates apoptosis and inflammation, inhibits ROS production and the expression of fibrosis markers in hepatocytes, and regulates immune cell populations and responses. Oxoglaucine protects against infections caused by Candida albicans and Klebsiella pneumoniae, and exerts effects on adjuvant-induced arthritis. Oxoglaucine can be used in studies related to arthritis, liver fibrosis, bacterial infections, and fungal infections.

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No. CAS: 5574-24-3
Fòrmula: C₂₀H₁₇NO₅
Peso molecular:351.35

Almacenamiento:

Powder -20°C, 3 years ; In solvent -80°C, 6 months , -20°C, 1 month

Oxoglaucine Chemical Structure

No. CAS: 5574-24-3

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Actividad biológica
- Descripciòn
- IC₅₀ & Target
- Cellular Effect
- In Vitro
- In Vivo
Chemical Information
Pureza y Documentación
Referencias
Calculators
Help & FAQs
Classifications
Bioz

Actividad biológica

Descripciòn

IC₅₀ & Target^[1]^[2]

TRPC5

CaMK II

IL-6

Collagen I

Caspase 3

TNF-α

Ver todos los productos específicos de isoformas NO Synthase :

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Smad1
Smad3

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Cellular Effect

Cell Line	Type	Value	Description	References
HeLa	CC₅₀	51 μM Compound: Oxoglaucine	Antiviral activity against Human rhinovirus type 14 in human HeLa Ohio-1 cells Antiviral activity against Human rhinovirus type 14 in human HeLa Ohio-1 cells	[PMID: 18590964]
HeLa	IC₅₀	0.3 μM Compound: Oxoglaucine	Cytotoxicity against human HeLa Ohio-1 cells Cytotoxicity against human HeLa Ohio-1 cells	[PMID: 18590964]
RAW264.7	IC₅₀	>50 μM Compound: 13	Antiinflammatory activity in mouse RAW264.7 assessed as inhibition of LPS-induced NO production preincubated for 30 mins followed by LPS stimulation measured after 24 hrs by Griess reagent based assay Antiinflammatory activity in mouse RAW264.7 assessed as inhibition of LPS-induced NO production preincubated for 30 mins followed by LPS stimulation measured after 24 hrs by Griess reagent based assay	[PMID: 33939429]

In Vitro

Oxoglaucine (1.25-40 ng/mL; 24 h) enhances the viability and proliferation of human osteoarthritic chondrocytes, while higher concentrations reduce their viability^[1].
Oxoglaucine (10-40 ng/mL; 24 h) exerts a protective effect on human osteoarthritic chondrocytes by enhancing cell viability; it promotes cartilage matrix maintenance in human osteoarthritic chondrocytes by increasing GAG secretion and upregulating the mRNA expression of cartilage-specific markers Sox-9, Aggrecan and Col 2A1^[1].
Oxoglaucine (10-40 ng/mL; 24 h) reduces Ca²⁺ influx in human osteoarthritic chondrocytes and downregulates the TRPV5/calmodulin/CAMK-II pathway in these cells^[1].
Oxoglaucine (10-15 μM; 24 h pretreatment, 6 h TGFβ stimulation) inhibits TGFβ-induced phosphorylation of Smad2 in Hepa1c1c7 cells and primary mouse hepatocytes, and additionally reduces TGFβ-induced phosphorylation of AKT in primary mouse hepatocytes. It suppresses the expression of fibrosis-related genes (collagen type I alpha 1 chain, α-SMA, fibronectin) and the corresponding protein (collagen type I alpha 1 chain), and inhibits the expression of IL6 and Ccl2^[2].
Oxoglaucine (10-15 μM; 24 h pretreatment, 6 h TGFβ stimulation) inhibits TGFβ-induced expression of fibrosis markers in human LX-2 hepatic stellate cells^[2].
Oxoglaucine (10-40 ng/mL; 24 h) alleviates inflammation and apoptosis in human osteoarthritic chondrocytes by downregulating the mRNA and protein expression of inflammatory, apoptotic and catabolic markers, as well as reducing the levels of NO, PGE2 and ADAMTS-5; it activates autophagy in human osteoarthritic chondrocytes by upregulating the mRNA and protein expression of autophagy-related markers LC3, Beclin-1, ATG5 and ATG7^[1].
Oxoglaucine (10 μM; pre-treatment for 24 h followed by TGFβ stimulation) inhibits TGFβ-induced ROS production and upregulates Smad7 expression in Hepa1c1c7 cells^[2].
Oxoglaucine (40 ng/mL; 24 h) activates autophagy in human osteoarthritic chondrocytes by increasing the formation of autolysosomes and promoting acidification^[1].
Oxoglaucine (2×10^-4 M; 72 h) inhibits mitogen-induced proliferation of mouse splenocytes^[4].

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

Cell Viability Assay^[1]

Cell Line:

human osteoarthritis (OA) chondrocytes
Concentration:

1.25, 2.50, 5.00, 10.00, 20.00, 40.00, 80.00, 160.00 ng/mL
Incubation Time:

24 h
Result:

Increased cell viability/proliferation significantly at 1.25-40 ng/mL.
Reduced cell viability significantly at 80 ng/mL and 160 ng/mL.

Cell Viability Assay^[1]

Cell Line:

human osteoarthritis (OA) chondrocytes
Concentration:

10, 20, 40 ng/mL
Incubation Time:

24 h
Result:

Increased the number of viable green-stained cells significantly and decreased the number of dead red-stained cells significantly compared to untreated control.

Real Time qPCR^[1]

Cell Line:

human osteoarthritis (OA) chondrocytes
Concentration:

10, 20, 40 ng/mL
Incubation Time:

24 h
Result:

Up-regulated mRNA expression of Sox-9, Aggrecan, and Col 2A1 significantly compared to untreated control.\nDown-regulated mRNA expression of IL-6, IL-1β, TNF-α, MMP-13, CASP-3, and BAX significantly.
Up-regulated mRNA expression of LC3, Beclin-1, ATG5, and ATG7 significantly.

ELISA Assay^[1]

Cell Line:

human osteoarthritis (OA) chondrocytes
Concentration:

10, 20, 40 ng/mL
Incubation Time:

24 h
Result:

Reduced PGE₂ and ADAMTS-5 levels significantly compared to untreated control.

Western Blot Analysis^[1]

Cell Line:

human osteoarthritis (OA) chondrocytes
Concentration:

10, 20, 40 ng/mL
Incubation Time:

24 h
Result:

Down-regulated protein expression of COX-2, iNOS, IL-6, IL-1β, TNF-α, MMP-13, CASP-3, and BAX significantly in a dose-dependent manner compared to untreated control.\nUp-regulated protein expression of LC3, Beclin-1, ATG5, and ATG7 significantly compared to untreated control.

Western Blot Analysis^[1]

Cell Line:

human osteoarthritis (OA) chondrocytes
Concentration:

40 ng/mL40 ng/mL plus 10^-8 mol/L D3
Incubation Time:

24 h
Result:

Decreased protein expression of TRPV5, calmodulin, and CAMK-II significantly at 40 ng/mL.
Reversed the down-regulatory effect on TRPV5, calmodulin, and CAMK-II when co-treated with D3.

Cell Autophagy Assay^[1]

Cell Line:

human osteoarthritis (OA) chondrocytes
Concentration:

10, 20, 40 ng/mL
Incubation Time:

24 h
Result:

Increased Cyto-ID Green fluorescence intensity dose-dependently, indicating enhanced autophagy activity.

Cell Viability Assay^[2]

Cell Line:

murine Hepa1c1c7 hepatoma cells
Concentration:

1, 5, 10, 15, 30 μM (viability assay)
10, 15 μM (apoptosis and cleaved caspase-3 analysis)
Incubation Time:

24 h
Result:

Did not significantly reduce cell viability at concentrations up to 15 μM.
Significantly reduced cell viability at 30 μM.
Showed no changes in cell number or morphology after 24 h exposure to 10 μM.
Did not increase apoptotic cell percentage at 10 and 15 μM compared to vehicle control.
Did not increase cleaved caspase-3 levels at 10 μM.

Western Blot Analysis^[2]

Cell Line:

murine Hepa1c1c7 hepatoma cells, primary mouse hepatocytes
Concentration:

10, 15 μM
Incubation Time:

24 h pretreatment, followed by 6 h TGFβ stimulation
Result:

Reduced TGFβ-induced Smad2 phosphorylation by approximately 40% in Hepa1c1c7 cells without altering total Smad2 levels.
Did not change TGFβ-induced AKT phosphorylation in Hepa1c1c7 cells.
Did not affect ERK phosphorylation in Hepa1c1c7 cells.
Attenuated TGFβ-induced Smad2 phosphorylation in primary mouse hepatocytes.
Significantly decreased TGFβ-induced AKT phosphorylation in primary mouse hepatocytes.

Real Time qPCR^[2]

Cell Line:

murine Hepa1c1c7 hepatoma cells, primary mouse hepatocytes
Concentration:

10, 15 μM
Incubation Time:

24 h pretreatment, followed by 6 h TGFβ stimulation
Result:

Reduced TGFβ-induced transcript levels of collagen type 1 alpha 1, α-SMA, and fibronectin in Hepa1c1c7 cells.
Did not affect Timp1 mRNA levels in Hepa1c1c7 cells.
Reduced TGFβ-induced transcript levels of collagen type 1 alpha 1, α-SMA, and fibronectin in primary mouse hepatocytes.
Significantly inhibited TGFβ-induced collagen type 1 alpha 1 protein expression in primary mouse hepatocytes.
Altered α-SMA mRNA levels when used alone, but did not affect Smad2 phosphorylation or other fibrogenic marker mRNA levels alone.

Real Time qPCR^[2]

Cell Line:

murine Hepa1c1c7 hepatoma cells, primary mouse hepatocytes
Concentration:

10 μM (Hepa1c1c7 cells)
15 μM (primary mouse hepatocytes)
Incubation Time:

24 h pretreatment, followed by 6 h TGFβ stimulation
Result:

Reduced TGFβ-induced Il6 and Ccl2 mRNA levels in Hepa1c1c7 cells.
Did not change Tnf-alpha mRNA levels in Hepa1c1c7 cells.
Reduced TGFβ-induced IL6 mRNA levels in primary mouse hepatocytes.
Did not affect Ccl2 and Tnf-alpha mRNA levels in primary mouse hepatocytes.

In Vivo

Oxoglaucine (40 ng/mL; intra-articular injection; twice a week for 4 weeks) alleviates surgically induced osteoarthritis in Sprague-Dawley rats, mitigates cartilage degeneration, reduces levels of inflammatory cytokines and TRPV5 pathway activity, and activates autophagy. Experimental results show that the gross score of rats decreases by approximately 50%, and the levels of TNF-α, IL-6, caspase-3 and BAX in the synovium also decrease^[1].
Oxoglaucine (0.02-5.0 mg/kg; i.p.; single administration; daily) regulates antibody-mediated immune responses in a dose-dependent and regimen-dependent manner. Among the tested regimens, the daily administration of 0.5 mg/kg for 3 consecutive days prior to immunization with sheep red blood cells (SRBC) exerts the strongest inhibitory effect on anti-SRBC IgM^[4].
Oxoglaucine (0.5 mg/kg; i.p.; administered on day 0 and day +2) significantly enhances SRBC-induced PLN responses^[4].
Oxoglaucine (0.5 mg/kg; i.p.; once daily for 5 consecutive days) enhances LPS-induced B cell activation and increases anti-LPS IgM levels^[4].
Oxoglaucine (1 mg/kg; i.p.; daily) modulates adjuvant-induced arthritis depending on the timing of treatment: it exacerbates paw swelling in the early stage of the disease and reduces swelling in the established disease stage^[4].
Oxoglaucine (1-20 mg/kg; i.p.; daily administration for 3 consecutive days before inoculation; single administration on day 0; single administration 24 h before inoculation) dose-dependently enhances resistance to Klebsiella pneumoniae infection^[4].
Oxoglaucine (10 mg/kg; i.p.; once daily; for 10 consecutive days) modulates splenic lymphocyte subsets in adult female ICR mice infected with Candida albicans, inhibits the accumulation of serum TNF-α, significantly reduces CD4⁺ cells, and prevents the infection-induced increase in CD8⁺ and Ig⁺ cells^[5].
Oxoglaucine (5 mg/kg; i.p.; once daily for 3 consecutive days) reduces the numbers of splenic CD4⁺, CD8⁺ and Ig⁺ cell populations when detected at 8 weeks post Candida albicans infection^[5].
Oxoglaucine (10 mg/kg, intraperitoneal injection, once daily for 10 consecutive days) suppresses late-stage serum TNF-α accumulation and elevates host resistance to Candida albicans infection in female ICR mice with adjuvant-induced arthritis^[5].

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

Animal Model:

Sprague-Dawley (male, 7 weeks old, 250-280 g, destabilization of the medial meniscus surgical induction)^[1]
Dosage:

40 ng/mL
Administration:

intra-articular; twice weekly; 4 weeks
Result:

Cut macroscopic cartilage wear and macroscopic scores by half.
Presented slight cartilage destruction and proteoglycan loss with lower OARSI scores than OA+PBS and OA+HA groups.
Suppressed synovial TNF-α, IL-6, caspase-3 and BAX levels.
Dropped cartilage TRPV5, TNF-α and MMP-13 protein expression.
Raised cartilage Beclin-1 expression and LC3-II/LC3-I ratio.

Animal Model:

ICR mice (male, 7-10 weeks old, 18-20 g body weight)^[4]
Dosage:

0.02 mg/kg; 0.05 mg/kg; 0.25 mg/kg; 0.5 mg/kg; 5.0 mg/kg
Administration:

i.p.; single dose; daily on Days −3, −2, −1; daily on Days 0, +1, +2; daily on Days +1, +2, +3, +4; daily on Days −3, −2, −1, 0, +1, +2, +3, +4
Result:

Cut in vitro anti-SRBC PFC counts at single 0.25 mg/kg and 0.5 mg/kg doses.
Dropped anti-SRBC IgM hemagglutination titers to 4.7 (0.5 mg/kg) and 5.2 (5.0 mg/kg) with Days -3, -2, -1 pre-immunization dosing, versus control titer 8.4.
Produced maximal anti-SRBC IgM titer suppression (4.7) via repeated 0.5 mg/kg Days -3, -2, -1 dosing; lowered titers to 5.6 with Days 0, +1, +2 dosing, but lifted titers to 10.0 with Days +1 to +4 dosing.
Slumped anti-LPS IgM OD492 to 0.307 (Days -3, -2, -1 repeated 0.5 mg/kg), 0.223 (Days 0, +1, +2) and 0.360 (Days +1 to +4); exerted no impact from single Day 0 dosing.

Animal Model:

ICR mice (male, 7-10 weeks old, 18-20 g body weight)^[4]
Dosage:

0.5 mg/kg
Administration:

i.p.; on Day 0 and Day +2
Result:

Increased the PLN index to 3.4 compared to the control index of 2.9.
Did not alter lymph node weight when administered alone.

Animal Model:

ICR mice (male, 7-10 weeks old, 18-20 g body weight)^[4]
Dosage:

0.5 mg/kg
Administration:

i.p.; daily from Day -3 to Day +1
Result:

Elevated serum anti-LPS IgM OD492 to 0.710 and IgG OD492 to 0.584, versus control 0.576 (IgM) and 0.360 (IgG).
Boosted spleen weight to 340 mg against control 260 mg.

Animal Model:

ICR mice (male, 7-10 weeks old, 18-20 g body weight)^[4]
Dosage:

1 mg/kg
Administration:

i.p.; daily on Days −7, −6, −5; daily from Day 0 to Day 14; daily from Day 7 to Day 14; daily from Day 14 to Day 21
Result:

Raised Day 14 paw swelling after dosing on Days -7, -6, -5 or Day 0-14.
Raised Day 28 paw swelling after dosing on Day 7-14.
Lessened Day 28 paw swelling after dosing on Day 14-21.

Animal Model:

ICR mice (male, 7-10 weeks old, 18-20 g body weight)^[4]
Dosage:

1 mg/kg; 2 mg/kg; 10 mg/kg; 20 mg/kg
Administration:

i.p.; daily on Days -7, -6, -5; single dose on Day 0; single dose 24 h pre-inoculation
Result:

Elevated primary inoculation survival to 80% (MST=12.0, control: 50%, MST=9.6) and secondary inoculation survival to 68.75% (MST=10.2, control: 30%, MST=5.7) via daily 1 mg/kg dosing on Days -7, -6, -5.
Boosted primary inoculation survival to 80% (MST=11.7) with no obvious improvement on secondary inoculation survival via single 2 mg/kg dosing on Day 0.
Cut survival down to 12.5% (MST=4.5, control:75%, MST=11.5) via 10 mg/kg administration 24 h before inoculation.
Dropped all survival to 0% (MST=4.5) via 20 mg/kg administration 24 h before inoculation.

Chemical Information

No. CAS 5574-24-3
Appearance Solid
Peso molecular 351.35
Fòrmula C₂₀H₁₇NO₅
SMILES

O=C1C2=CC(OC)=C(OC)C=C2C3=C(OC)C(OC)=CC4=CC=NC1=C43
Synonyms

O-Methylatheroline
Structure Classification
- Alkaloids
- Quinoline Alkaloids
Initial Source
Envío

Room temperature in continental US; may vary elsewhere.

Almacenamiento

Powder	-20°C	3 years
In solvent	-80°C	6 months
	-20°C	1 month

Pureza y Documentación

Instrucciones de manejo (2659 KB)

Referencias

[1]. Zhong G, et al. Oxoglaucine mediates Ca influx and activates autophagy to alleviate osteoarthritis through the TRPV5/calmodulin/CAMK-II pathway. British journal of pharmacology. 2021 Aug;178(15):2931-2947. [Content Brief]

[2]. Azamov B, et al. Oxoglaucine Suppresses Hepatic Fibrosis by Inhibiting TGFβ-Induced Smad2 Phosphorylation and ROS Generation. Molecules (Basel, Switzerland). 2023 Jun 24;28(13):4971. [Content Brief]

[3]. Harrigan GG, et al. Isolation of bioactive and other oxoaporphine alkaloids from two annonaceous plants, Xylopia aethiopica and Miliusa cf. banacea. Journal of natural products. 1994 Jan;57(1):68-73. [Content Brief]

[4]. Ivanovska N, et al. Immunopharmacological activity of aporphinoid alkaloid oxoglaucine. Pharmacological research. 1997 Apr;35(4):267-72. [Content Brief]

[5]. Ivanovska N, et al. Treatment with oxoglaucine can enhance host resistance to Candida albicans infection of mice with adjuvant arthritis. Diagnostic microbiology and infectious disease. 2000 Sep;38(1):17-20. [Content Brief]

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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.

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Oxoglaucine

Ver todos los productos específicos de isoformas NO Synthase

Ver todos los productos específicos de isoformas TRP Channel

Ver todos los productos específicos de isoformas CaMK

Ver todos los productos específicos de isoformas Calmodulin

Ver todos los productos específicos de isoformas TGF-beta/Smad

Ver todos los productos específicos de isoformas Interleukin Related

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Ver todos los productos específicos de isoformas TNF Receptor

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Actividad biológica

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Referencias

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Help & FAQs

Oxoglaucine Related Classifications

HY-N2595 Related Classifications