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| 1g | ||
| 2g | ||
| Other Sizes |
Purity: ≥98%
Eritadenine is a potent inhibitor of S-adenosyl-L-homocysteine hydrolase (SAHH), decreasing total cholesterol levels in plasma. Eritadenine [2(R),3(R)-dihydroxy-4-(9-adenyl)butanoic acid, 253 Da; EA] is one of these secondary metabolites (Figure 1A), which is a purine alkaloid.
| Targets |
ACE/angiotensin converting enzyme
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|---|---|
| ln Vitro |
The in vitro inhibitory effect of mushroom-derived eritadenine (EA) on angiotensin-converting enzyme (ACE) activity was evaluated in 11 major Korean edible mushrooms. EA exhibited an IC50 of 0.091 μM against ACE, while captopril (CP), used as a reference compound, showed an IC50 of 0.025 μM. Kinetic analysis of the ACE-catalyzed reaction using the substrate hippuryl-L-histidyl-L-leucine (HHL) in the presence or absence of EA revealed that the maximum velocity (Vmax) remained unchanged at 0.0465 O.D./30 min, whereas the Michaelis constant (Km) increased from 2.063 mM to 3.887 mM. This pattern indicates that EA acts as a competitive inhibitor, competing with HHL for the enzyme's active site. HPLC analysis of EA content in different mushroom species showed that Lentinus edodes with a soft cap contained the highest concentration of EA (642.8 mg%), while Phellinus linteus, characterized by a hard cap, had the lowest EA content (9.4 mg%). These findings suggest that EA is a potent competitive inhibitor of ACE and that soft-capped edible mushrooms are rich sources of EA.
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| Enzyme Assay |
ACE Inhibition Assay: [1]
The inhibition of ACE activity by various concentrations of EA and CP as well as their IC50 values were measured using a spectrophotometric method with HHL as substrate as described by Chang et al. with modification. Briefly, a 20 mM sodium borate buffer containing 0.3 M NaCl (pH 8.3) was used for the preparation of EA, CP, ACE, and substrate HHL solutions. The ACE-catalyzed reaction was performed for 30 min at 37 °C in test tubes of the following compositions: 100 μL of EA or CP, 100 μL of ACE solution (40 mU/mL), and 100 μL of HHL (15 mM) solutions (A1); 100 μL of EA or CP solution and 200 μL of borate buffer (A2); 100 μL of borate buffer, 100 μL of ACE solution, and 100 μL of HHL solution (A3); and 300 μL of borate buffer (A4). The enzymatic reaction was stopped by adding 3 mL of alkaline solution of OPA solution (pH 12.0). The absorbance of each reaction was measured at 390 nm using a Beckman DU-640 (Brea, CA, USA), after incubation for 20 min at 25 °C. Inhibition of ACE by EA or CP was calculated using the following equation: inhibition (%) = [1 – (A1 – A2)/(A3 – A4)] × 100. The IC50 value of ACE activity was calculated by the equation IC50 = (50 – b)/m derived from a linear regression graph of ACE activation, where b is the intercept and m is the slope of the equation. Determination of Kinetic Parameters of ACE Inhibition: [1] Kinetic parameters of Vmax and Km values were determined according to the Michaelis–Menten kinetic model. The reaction rate for the formation of l-histidyl-l-leucine from HHL by ACE (40 mU/mL) was determined by the above-mentioned method with EA (0.091 μM) or CP (0.00625 μM) and without EA or CP to get the saturation curves and then plotted against HHL concentrations (0.94, 1.85, 3.75, 7.50, 15 mM). The Lineweaver–Burk plot was derived using the saturation curves to determine the type of inhibition. Kinetic parameters (Km and Vmax) were calculated using MS Excel. |
| References |
[1]. Eritadenine from Edible Mushrooms Inhibits Activity of Angiotensin Converting Enzyme in Vitro. J Agric Food Chem. 2016 Mar 23;64(11):2263-8.
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| Additional Infomation |
Leutinacin is one of the 6-aminopurine compounds. It has been reported that gibberellins are present in button mushrooms and shiitake mushrooms, and relevant data exists.
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| Molecular Formula |
C9H11N5O4
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|---|---|
| Molecular Weight |
253.21474
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| Exact Mass |
253.081
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| Elemental Analysis |
C, 42.69; H, 4.38; N, 27.66; O, 25.27
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| CAS # |
23918-98-1
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| PubChem CID |
159961
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| Appearance |
White to off-white solid powder
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| Density |
1.92g/cm3
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| Boiling Point |
721.3ºC at 760 mmHg
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| Flash Point |
390ºC
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| Vapour Pressure |
7.75E-22mmHg at 25°C
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| Index of Refraction |
1.823
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| LogP |
-1.8
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| Hydrogen Bond Donor Count |
4
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| Hydrogen Bond Acceptor Count |
8
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| Rotatable Bond Count |
4
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| Heavy Atom Count |
18
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| Complexity |
317
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| Defined Atom Stereocenter Count |
2
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| SMILES |
OC([C@@H]([C@@H](CN1C=NC2=C(N=CN=C12)N)O)O)=O
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| InChi Key |
LIEMBEWXEZJEEZ-INEUFUBQSA-N
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| InChi Code |
InChI=1S/C9H11N5O4/c10-7-5-8(12-2-11-7)14(3-13-5)1-4(15)6(16)9(17)18/h2-4,6,15-16H,1H2,(H,17,18)(H2,10,11,12)/t4-,6-/m1/s1
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| Chemical Name |
(2R,3R)-4-(6-aminopurin-9-yl)-2,3-dihydroxybutanoic acid
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| Synonyms |
Eritadenine; Lentinacin; Eritadenine; d-eritadenine; 23918-98-1; Lentinacin; (2R,3R)-4-(6-aminopurin-9-yl)-2,3-dihydroxybutanoic acid; Lentysine; D-Eritadenine
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| HS Tariff Code |
2934.99.9001
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| 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)
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| 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
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| 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 | 3.9493 mL | 19.7465 mL | 39.4929 mL | |
| 5 mM | 0.7899 mL | 3.9493 mL | 7.8986 mL | |
| 10 mM | 0.3949 mL | 1.9746 mL | 3.9493 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.
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