Art. -Nr.: HY-N10076

Ganomycin I

Ganomycin I is a non-competitive dual inhibitor of α-glucosidase and HMG-CoA reductase, with IC₅₀ values of 0.3 μM and 12.3 μM, respectively. Ganomycin I inhibits HIV-1 protease, with an IC₅₀ of 7.5 μg/mL. Ganomycin I also suppresses RANKL-induced osteoclast differentiation and bone resorption by inhibiting the activation of ERK, JNK and p38 MAPK, as well as downregulating the c-Fos/NFATc1 signaling pathway. Ganomycin I exhibits antibacterial activity against Gram-positive bacteria, and shows weak activity against Mycobacterium tuberculosis H37Ra. It can be used in research related to metabolic diseases, bone metabolism and anti-infection.

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CAS. Nr.: 1191255-15-8
Formel: C₂₁H₂₆O₄
Molecular Weight:342.43

Speicherung:

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

Data Sheet (289 KB)

Ganomycin I Chemical Structure

CAS. Nr.: 1191255-15-8

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Use of MCE Products

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

Biologische Aktivität
- Beschreibung
- IC₅₀ & Target
- In Vitro
- In Vivo
Chemical Information
Reinheit & Dokumentation
Verweise
Calculators
Help & FAQs
Classifications
Bioz

Biologische Aktivität

Beschreibung

IC₅₀ & Target

^[1]^[3]^[7]

α‑glucosidase

0.38 μM (IC₅₀, rat small intestinal mucosa)

α‑glucosidase

0.3 μM (IC₅₀, Baker's yeast)

α‑glucosidase

0.4 μM (IC₅₀, rat small intestinal mucosa)

HMG-CoA reductase

12.3 μM (IC₅₀)

HIV-1 Protease

7.5 μg/mL (IC₅₀)

In Vitro

Ganomycin I inhibits Baker's yeast α-glucosidase and rat small intestinal mucosa α-glucosidase with IC₅₀ values of 0.3 μM and 0.4 μM, respectively; it also inhibits rat intestinal sucrase and maltase with IC₅₀ values of 67.6 μM and 3.6 μM, respectively^[3].
Ganomycin I (3-30 μM; 6 days) inhibits RANKL-induced osteoclastogenesis in mouse bone marrow macrophages (BMMs) in a dose-dependent manner by reducing the number of mature osteoclasts and downregulating the expression of the osteoclast marker proteins c-Src and CtsK^[2].
Ganomycin I (3-30 μM; 4 days) inhibits RANKL-induced osteoclast formation in mouse RAW264.7 cells in a dose-dependent manner^[2].
Ganomycin I (3-30 μM; 72 h) increases the cell viability of mouse bone marrow macrophages (BMMs) after incubation at concentrations of 3, 10, and 30 μM for 72 h, indicating that its anti-osteoclastogenic activity does not originate from cytotoxicity^[2].
Ganomycin I (3-30 μM; 7 days) dose-dependently inhibits RANKL-induced bone resorptive activity in mouse bone marrow macrophages (BMMs) cultured on OsteoAssay Surface plates^[2].
Ganomycin I (3-30 μM; 7 days) dose-dependently inhibits RANKL-induced actin ring formation in mouse bone marrow macrophages (BMMs), where actin ring serves as a marker of mature osteoclasts^[2].
Ganomycin I (3-30 μM; pretreated prior to RANKL stimulation) dose-dependently inhibits RANKL-induced activation of ERK, JNK and p38 MAPKs, as well as the downstream expression of c-Fos and NFATc1, without affecting the activation of the NF-κB pathway in mouse RAW264.7 cells^[2].
Ganomycin I (3-30 μM; pretreated prior to RANKL stimulation) dose-dependently inhibits RANKL-induced nuclear translocation of NFATc1 in mouse RAW264.7 cells^[2].
Ganomycin I (3-30 μM; 4 days) dose-dependently reduces the expression of RANKL-induced NFATc1 target genes DC-STAMP, OSCAR, MMP-9 and TRAP in mouse bone marrow-derived macrophages (BMMs)^[2].
Ganomycin I (compound 2) shows no activity against porcine pancreatic lipase^[5].
Ganomycin I (50 μg/mL) exhibits no cytotoxicity toward non-malignant Vero cells^[6].
Ganomycin I exhibits cytotoxicity against E-PR293 cells, so its anti-HIV-1 protease activity cannot be determined in this cell system^[4].
Ganomycin I inhibits recombinant HIV-1 protease expressed in E. coli, with an IC₅₀ of 7.5 µg/mL, and forms hydrogen bonds with the Asp30 residue at the active site of this enzyme^[7].
Ganomycin I exhibits weak activity against Mycobacterium tuberculosis H37Ra with an MIC of 50 μg/mL; its MIC values against Gram-positive bacteria Bacillus cereus, Enterococcus faecium and Staphylococcus aureus are 25, 25 and 12.5 μg/mL, respectively^[6].
Ganomycin I inhibits HMG-CoA reductase with an IC₅₀ of 12.3 μM^[3].
Ganomycin I exhibits non-competitive inhibition against both α-glucosidase and HMG-CoA reductase; kinetic assays use Ganomycin I at 0.3-1 μM for α-glucosidase detection and 5-20 μM for HMG-CoA reductase detection^[3].

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

Cell Viability Assay^[2]

Cell Line:

mouse BMMs
Concentration:

3, 10, 30 μM
Incubation Time:

72 h
Result:

Did not decrease cell viability of BMMs.
Increased cell viability at the tested concentrations.

Western Blot Analysis^[2]

Cell Line:

mouse RAW264.7 cells
Concentration:

3, 10, 30 μM
Incubation Time:

10 min, 15 min,24 h, 48 h, 4 d
Result:

Significantly decreased RANKL-induced phosphorylation levels of ERK, JNK, and p38 MAPKs in a concentration-dependent manner.
Attenuated RANKL-induced expression of c-Fos and NFATc1.
Did not block RANKL-induced degradation of IκBα.

Immunofluorescence^[2]

Cell Line:

mouse RAW264.7 cells
Concentration:

30 μM
Incubation Time:

48 h
Result:

Significantly suppressed RANKL-induced nuclear translocation of NFATc1.

Real Time qPCR^[2]

Cell Line:

mouse BMMs
Concentration:

3, 10, 30 μM
Incubation Time:

4 days
Result:

Significantly inhibited the expression of DC-STAMP, OSCAR, MMP-9, and TRAP genes in a concentration-dependent manner during RANKL-induced osteoclastogenesis.

In Vivo

Ganomycin I (3.0 mg/kg; p.o.; once daily; for 5 consecutive weeks) exerts effects on improving hyperglycemia and hyperlipidemia in diet-induced obese male C57BL/6J mice^[1].
Ganomycin I (1-5 mg/kg; p.o.; daily; 21-28 days) exerts potent hypoglycemic, hypolipidemic, insulin-sensitizing, and serum AST-lowering effects in KK-A_y mice; the insulin-sensitizing efficacy of the 5 mg/kg dose is superior to that of thiazolidinedione insulin sensitizers, both doses increase hepatic glycogen levels after 4 weeks of administration, and no reduction in serum ALT levels is observed^[3].
No obvious abnormalities in behavior, feces and urine, convulsions, sleep or coma are observed, and no deaths are recorded within the 24 h and subsequent 14-day observation period after a single oral dose of Ganomycin I up to 3 g/kg^[3].

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

Animal Model:

C57BL/6J mice (male; 8 weeks old; high-fat diet-induced obesity)^[1]
Dosage:

3.0 mg/kg
Administration:

p.o.; daily; 5 weeks
Result:

Exhibited similar efficacy to compound 7d in improving hyperglycemia and hyperlipidemia in diet-induced obese mice.

Animal Model:

8-week-old insulin-resistant male KK-A^y mice; C57BL/6J normal control^[3]
Dosage:

1, 5 mg/kg
Administration:

p.o.; daily; 21 days
Result:

Reduced fasting/free-feeding glucose and HbA1c.
Improved OSTT, OGTT, ITT, serum insulin and ISI.
Reduced NEFA, TG, TC and LDL-C.
Increased hepatic glycogen.
Decreased AST.
Improved hepatic steatosis and reduced WAT adipocyte size.

Chemical Information

CAS. Nr. 1191255-15-8
Molecular Weight 342.43
Formel C₂₁H₂₆O₄
SMILES

OC1=C(C=C(C=C1)O)[C@@]2([H])C=C(C(O2)=O)CC/C=C(C)/CC/C=C(C)/C
Structure Classification
- Phenols
- Polyphenols
Initial Source
- Microorganisms
Ganoderma colossum
Versand

Room temperature in continental US; may vary elsewhere.
Speicherung

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

Reinheit & Dokumentation

Select Batch:

Reinheit: 99.98%

Assay: 99.98%

ee.: 99.98%

Data Sheet (289 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]. Wang K, et al. Structural Modification of Natural Product Ganomycin I Leading to Discovery of a α-Glucosidase and HMG-CoA Reductase Dual Inhibitor Improving Obesity and Metabolic Dysfunction in Vivo. Journal of medicinal chemistry. 2018 Apr 26;61(8):3609-3625. [Content Brief]

[2]. Tran PT, et al. Ganomycin I from Ganoderma lucidum attenuates RANKL-mediated osteoclastogenesis by inhibiting MAPKs and NFATc1. Phytomedicine : international journal of phytotherapy and phytopharmacology. 2019 Mar 01;55:1-8. [Content Brief]

[3]. Wang K, et al. A novel class of α-glucosidase and HMG-CoA reductase inhibitors from Ganoderma leucocontextum and the anti-diabetic properties of ganomycin I in KK-Ay mice. Eur J Med Chem. 2017;127:1035-1046.

[4]. Yajima A, et al. Concise Syntheses and Biological Activities of Ganomycin I and Fornicin A. Eur J Org Chem. 2014:731-738.

[5]. Chen HP, et al. (+)- and (−)-Ganodilactone, a Pair of Meroterpenoid Dimers with Pancreatic Lipase Inhibitory Activities from the Macromycete Ganoderma leucocontextum. RSC Adv. 2016.

[6]. Li W, et al. Isolation of 3,4-seco-27-norlanostane triterpenoids from cultivated fruiting bodies of Ganoderma orbiforme. Phytochemistry Letters. 2018;28:104-109.

[7]. El Dine RS, et al. Inhibition of the dimerization and active site of HIV-1 protease by secondary metabolites from the Vietnamese mushroom Ganoderma colossum. Journal of natural products. 2009 Nov;72(11):2019-23.

Calculators

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)}

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.

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Ganomycin I