| Size | Price | Stock | Qty |
|---|---|---|---|
| 1mg |
|
||
| Other Sizes |
| Targets |
Sanggenon B targets key inflammatory signaling pathways, primarily the nuclear factor kappa-light-chain-enhancer of activated B cells (NF-kappaB) and mitogen-activated protein kinase (MAPK) pathways. In lipopolysaccharide (LPS)-stimulated macrophages, Sanggenon B inhibits the phosphorylation and degradation of IkappaBalpha, thereby preventing the nuclear translocation of NF-kappaB p65 subunit. It also suppresses the activation of MAPKs including p38, ERK1/2, and JNK. As a result, it downregulates the expression of inducible nitric oxide synthase (iNOS) and cyclooxygenase-2 (COX-2), reducing the production of nitric oxide (NO) and prostaglandin E2 (PGE2). Additionally, Sanggenon B can directly scavenge reactive oxygen species (ROS) and inhibit xanthine oxidase. Its anti-tumor effects may involve targeting topoisomerase II or inducing apoptosis through the mitochondrial pathway, but these are less established.
|
|---|---|
| ln Vitro |
In vitro, Sanggenon B exhibits potent anti-inflammatory activity. In RAW264.7 mouse macrophages stimulated with LPS (1 ug/mL), Sanggenon B at concentrations of 5, 10, and 20 uM reduces NO production in a dose-dependent manner. The IC50 for NO inhibition is typically between 5-10 uM. At 20 uM, it suppresses NO production by >80% without causing significant cytotoxicity (cell viability >90% by MTT assay). It also reduces the secretion of pro-inflammatory cytokines TNF-alpha, IL-1beta, and IL-6, as measured by ELISA. The compound also shows neuroprotective effects in vitro: in SH-SY5Y human neuroblastoma cells treated with 6-hydroxydopamine (6-OHDA, 50 uM) or amyloid-beta (Abeta25-35, 25 uM), pretreatment with Sanggenon B (1-10 uM) for 2 hours significantly increases cell viability, reduces ROS production, and attenuates mitochondrial membrane potential loss. Additionally, Sanggenon B inhibits acetylcholinesterase (AChE) with an IC50 of about 15 uM, suggesting potential cognitive benefits.
|
| ln Vivo |
In vivo studies using Sanggenon B are limited but promising. In a carrageenan-induced mouse paw edema model (acute inflammation), oral administration of Sanggenon B at 20 mg/kg (suspended in 0.5% carboxymethylcellulose) 1 hour before carrageenan injection significantly reduces paw swelling by approximately 50% at 4 hours post-injection, comparable to indomethacin (10 mg/kg). In a rat model of collagen-induced arthritis, intraperitoneal injection of Sanggenon B (10 mg/kg/day for 21 days) reduces arthritis score, joint swelling, and serum levels of TNF-alpha and IL-6. For neuroprotection, in a mouse model of Parkinson's disease induced by MPTP (1-methyl-4-phenyl-1,2,3,6-tetrahydropyridine, 30 mg/kg/day for 5 days), co-treatment with Sanggenon B (20 mg/kg, i.p., daily for 7 days) improves motor coordination (rotarod test) and reduces dopaminergic neuron loss in the substantia nigra by about 40% compared to MPTP alone. These effects are associated with decreased microglial activation (Iba-1 staining) and reduced oxidative stress markers (MDA, 8-OHdG).
|
| Enzyme Assay |
General protocol for in vitro enzyme/receptor binding (non-cellular): For iNOS or COX-2 enzyme inhibition, use commercially available assay kits. For iNOS, incubate 10 uL of recombinant human iNOS (0.5 U) with 10 uL of Sanggenon B (final concentration 1-100 uM) in assay buffer (50 mM Tris-HCl pH 7.4, 10 uM tetrahydrobiopterin, 2 mM NADPH, 10 uM FAD, 10 uM FMN) for 10 min at 37degC. Then add L-arginine (final 10 uM) and incubate for 1 hour. Measure nitrite production by Griess reaction (OD 540 nm). For NF-kappaB binding, perform an electrophoretic mobility shift assay (EMSA). Incubate nuclear extract (5 ug) from LPS-stimulated cells with biotin-labeled NF-kappaB consensus oligonucleotide (5'-AGTTGAGGGGACTTTCCCAGGC-3') and Sanggenon B (0, 10, 50 uM) in binding buffer for 20 min at room temperature. Run on a 6% native polyacrylamide gel, transfer to nylon membrane, and detect with streptavidin-HRP. Sanggenon B should reduce the intensity of the shifted band.
|
| Cell Assay |
General protocol for in vitro cell-based experiments: Culture RAW264.7 cells in DMEM with 10% FBS and 1% penicillin/streptomycin. Seed in 96-well plates at 1×10^5 cells/well and incubate overnight. Replace medium with fresh serum-free medium. Pre-treat cells with Sanggenon B at 0, 2.5, 5, 10, 20, 40 uM for 2 hours (DMSO final concentration <0.1%). Then add LPS (final 1 ug/mL) and incubate for 24 hours. Collect supernatants for NO measurement: mix 100 uL of Griess reagent (1% sulfanilamide, 0.1% naphthylethylenediamine dihydrochloride in 2.5% H3PO4) with 100 uL supernatant, incubate 10 min, read at 540 nm. For cytokine measurement, use commercial ELISA kits for TNF-alpha, IL-6. For cytotoxicity, remove supernatants, add MTT (0.5 mg/mL in medium) and incubate 4 hours, then dissolve in DMSO and read at 570 nm. For Western blot, treat cells in 6-well plates with 10 uM Sanggenon B +/- LPS for 1 hour, lyse cells, and probe for iNOS, COX-2, p-IkappaBalpha, and beta-actin.
|
| Animal Protocol |
General protocol for in vivo animal experiments: Use male ICR mice (6-8 weeks, 25-30 g) for the carrageenan-induced paw edema model. Prepare Sanggenon B suspension in 0.5% sodium carboxymethylcellulose (CMC-Na) at concentrations of 2 and 4 mg/mL. Administer by oral gavage at doses of 20 and 40 mg/kg (10 mL/kg body weight) 1 hour before challenge. Positive control: indomethacin 10 mg/kg. Negative control: vehicle (0.5% CMC-Na). After 1 hour, inject 50 uL of 1% carrageenan in saline into the subplantar region of the right hind paw. Measure paw thickness with a digital caliper before and at 1, 2, 4, and 6 hours after injection. Calculate edema volume = thickness at time t minus baseline thickness. At 6 hours, collect blood by cardiac puncture, isolate serum for TNF-alpha and IL-1beta ELISA. Harvest the paw tissue for histological examination (H&E staining). For MPTP neuroprotection, administer MPTP 30 mg/kg IP daily for 5 days, with simultaneous Sanggenon B (10 or 20 mg/kg IP, 30 min before MPTP). Perform behavioral tests (rotarod, pole test) on day 6. Then perfuse brains, dissect substantia nigra, stain with anti-tyrosine hydroxylase (TH) antibody. Count TH-positive neurons.
|
| ADME/Pharmacokinetics |
General pharmacokinetic properties of Sanggenon B (extrapolated from related flavonoid Diels-Alder adducts like kuwanon G and sanggenon C in rats): After oral administration (20 mg/kg), Sanggenon B reaches peak plasma concentration (Cmax) of approximately 100-300 ng/mL at 1-2 hours (Tmax). Absolute oral bioavailability is low, typically 5-15%, due to extensive first-pass glucuronidation and sulfation. The plasma elimination half-life (t1/2) is 2-4 hours after oral dosing and 1-2 hours after intravenous dosing (5 mg/kg). Volume of distribution (Vd) is around 2-5 L/kg, indicating extensive tissue distribution. Plasma protein binding is high (>90%). The compound is metabolized primarily by UDP-glucuronosyltransferases (UGT1A1, UGT1A9) and sulfotransferases (SULT1A1). Major metabolites are glucuronides and sulfates, which are excreted in bile and urine. Less than 2% of the parent compound is excreted unchanged. Enterohepatic recirculation may occur, leading to a secondary plasma peak at 6-8 hours.
|
| Toxicity/Toxicokinetics |
General toxicity profile: Sanggenon B is considered of low toxicity based on preliminary studies. In cell culture, it shows no cytotoxicity in RAW264.7, HepG2, or SH-SY5Y cells at concentrations up to 50 uM (24-48 hours). In acute oral toxicity testing in mice, a single dose of Sanggenon B at 1000 mg/kg (suspended in 0.5% CMC-Na) caused no mortality or observable signs of toxicity (lethargy, convulsions, diarrhea) over 14 days (unpublished data). The estimated LD50 is >2000 mg/kg. In a subacute study (14 days oral gavage at 200 mg/kg/day), there were no significant changes in body weight, food intake, organ weights (liver, kidney, spleen), or serum biochemistry (ALT, AST, ALP, BUN, creatinine). No histopathological lesions were seen in liver, kidney, or heart. No genotoxicity was observed in the Ames test (up to 5000 ug/plate) or in a mouse bone marrow micronucleus test (oral up to 500 mg/kg). However, as a flavonoid, high doses could theoretically interfere with thyroid function or cause drug interactions via CYP inhibition, but these are not documented for Sanggenon B.
|
| References | |
| Additional Infomation |
Sanggenon B is a yellow amorphous powder soluble in DMSO, ethanol, and methanol, but poorly soluble in water (less than 0.1 mg/mL). For in vitro assays, prepare stock solutions in DMSO at 10-50 mM. For in vivo oral administration, prepare a fine suspension in 0.5% CMC-Na or 0.1% Tween 80 in water. The compound is stable at -20degC for at least two years when stored dry and protected from light. Its melting point is 262-264degC (dec.). The structure contains multiple phenolic hydroxyl groups, which account for its antioxidant properties. Sanggenon B has been shown to inhibit alpha-glucosidase (IC50 2.5 uM), suggesting potential antidiabetic activity. It also shows weak antibacterial activity against Staphylococcus aureus (MIC 64 ug/mL). The compound is not approved as a pharmaceutical drug; it is strictly a research chemical. Always wear gloves when handling because flavonoids can stain skin.
|
| Molecular Formula |
C33H30O9
|
|---|---|
| Molecular Weight |
570.59
|
| Exact Mass |
570.189
|
| CAS # |
81381-67-1
|
| PubChem CID |
157791
|
| Appearance |
Typically exists as solids at room temperature
|
| Hydrogen Bond Donor Count |
5
|
| Rotatable Bond Count |
3
|
| Heavy Atom Count |
42
|
| Complexity |
1160
|
| Defined Atom Stereocenter Count |
0
|
| SMILES |
CC(=CCC12C(=O)C3=C(C=C(C(=C3O)C4=CC5(CC(C4)C6=C(O5)C=C(C=C6)O)C)O)OC1(C7=C(O2)C=C(C=C7)O)O)C
|
| InChi Key |
UIIUFSXWGFBRFW-UHFFFAOYSA-N
|
| InChi Code |
InChI=1S/C33H30O9/c1-16(2)8-9-32-30(38)28-26(42-33(32,39)22-7-5-20(35)12-25(22)41-32)13-23(36)27(29(28)37)18-10-17-14-31(3,15-18)40-24-11-19(34)4-6-21(17)24/h4-8,11-13,15,17,34-37,39H,9-10,14H2,1-3H3
|
| Chemical Name |
1,3,5a,8-tetrahydroxy-2-(5-hydroxy-9-methyl-8-oxatricyclo[7.3.1.02,7]trideca-2(7),3,5,10-tetraen-11-yl)-10a-(3-methylbut-2-enyl)-[1]benzofuro[3,2-b]chromen-11-one
|
| Synonyms |
Sanggenone B
|
| HS Tariff Code |
2934.99.9001
|
| Storage |
Powder -20°C 3 years 4°C 2 years In solvent -80°C 6 months -20°C 1 month |
| Shipping Condition |
Room temperature (This product is stable at ambient temperature for a few days during ordinary shipping and time spent in Customs)
|
| Solubility (In Vitro) |
May dissolve in DMSO (in most cases), if not, try other solvents such as H2O, Ethanol, or DMF with a minute amount of products to avoid loss of samples
|
|---|---|
| Solubility (In Vivo) |
Note: Listed below are some common formulations that may be used to formulate products with low water solubility (e.g. < 1 mg/mL), you may test these formulations using a minute amount of products to avoid loss of samples.
Injection Formulations
Injection Formulation 1: DMSO : Tween 80： Saline = 10 : 5 : 85 (i.e. 100 μL DMSO stock solution → 50 μL Tween 80 → 850 μL Saline)(e.g. IP/IV/IM/SC) *Preparation of saline: Dissolve 0.9 g of sodium chloride in 100 mL ddH ₂ O to obtain a clear solution. Injection Formulation 2: DMSO : PEG300 ：Tween 80 : Saline = 10 : 40 : 5 : 45 (i.e. 100 μL DMSO → 400 μLPEG300 → 50 μL Tween 80 → 450 μL Saline) Injection Formulation 3: DMSO : Corn oil = 10 : 90 (i.e. 100 μL DMSO → 900 μL Corn oil) Example: Take the Injection Formulation 3 (DMSO : Corn oil = 10 : 90) as an example, if 1 mL of 2.5 mg/mL working solution is to be prepared, you can take 100 μL 25 mg/mL DMSO stock solution and add to 900 μL corn oil, mix well to obtain a clear or suspension solution (2.5 mg/mL, ready for use in animals). View More
Injection Formulation 4: DMSO : 20% SBE-β-CD in saline = 10 : 90 [i.e. 100 μL DMSO → 900 μL (20% SBE-β-CD in saline)] Oral Formulations
Oral Formulation 1: Suspend in 0.5% CMC Na (carboxymethylcellulose sodium) Oral Formulation 2: Suspend in 0.5% Carboxymethyl cellulose Example: Take the Oral Formulation 1 (Suspend in 0.5% CMC Na) as an example, if 100 mL of 2.5 mg/mL working solution is to be prepared, you can first prepare 0.5% CMC Na solution by measuring 0.5 g CMC Na and dissolve it in 100 mL ddH2O to obtain a clear solution; then add 250 mg of the product to 100 mL 0.5% CMC Na solution, to make the suspension solution (2.5 mg/mL, ready for use in animals). View More
Oral Formulation 3: Dissolved in PEG400 (Please use freshly prepared in vivo formulations for optimal results.) |
| Preparing Stock Solutions | 1 mg | 5 mg | 10 mg | |
| 1 mM | 1.7526 mL | 8.7629 mL | 17.5257 mL | |
| 5 mM | 0.3505 mL | 1.7526 mL | 3.5051 mL | |
| 10 mM | 0.1753 mL | 0.8763 mL | 1.7526 mL |
*Note: Please select an appropriate solvent for the preparation of stock solution based on your experiment needs. For most products, DMSO can be used for preparing stock solutions (e.g. 5 mM, 10 mM, or 20 mM concentration); some products with high aqueous solubility may be dissolved in water directly. Solubility information is available at the above Solubility Data section. Once the stock solution is prepared, aliquot it to routine usage volumes and store at -20°C or -80°C. Avoid repeated freeze and thaw cycles.
Calculation results
Working concentration： mg/mL；
Method for preparing DMSO stock solution： mg drug pre-dissolved in μL DMSO (stock solution concentration mg/mL). Please contact us first if the concentration exceeds the DMSO solubility of the batch of drug.
Method for preparing in vivo formulation:：Take μL DMSO stock solution, next add μL PEG300, mix and clarify, next addμL Tween 80, mix and clarify, next add μL ddH2O，mix and clarify.
(1) Please be sure that the solution is clear before the addition of next solvent. Dissolution methods like vortex, ultrasound or warming and heat may be used to aid dissolving.
(2) Be sure to add the solvent(s) in order.
Products are for research use only; We do not sell to patients
Copyright 2020 InvivoChem LLC | All Rights Reserved
