| Size | Price | Stock | Qty |
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| 5mg |
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| 10mg |
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| 50mg |
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| Other Sizes |
| Targets |
S-(+)-Marmesin is the natural substrate for the enzyme Psoralen Synthase (CYP71AJ1) from Ammi majus. It is not described as a drug with a specific therapeutic target in this study.
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| ln Vitro |
S-(+)-Marmesin ((+)-marmesin) has a Km of 1.5 ± 0.5 μM for recombinant psoralen synthase, which is greater than the substrate affinity of other CYP71 subfamily enzymes engaged in plant secondary metabolism[1]. The dual inhibitory activity of COX-2/5-LOX is demonstrated by S-(+)-Marmesin ((+)-marmesin) [2].
S-(+)-Marmesin is efficiently converted to psoralen by the recombinant cytochrome P450 enzyme psoralen synthase (CYP71AJ1mut) expressed in yeast microsomes. The reaction requires NADPH as a cofactor. Kinetic analysis of the psoralen synthase with S-(+)-Marmesin as substrate yielded an apparent Km of 1.5 ± 0.5 µM and a kcat of 340 ± 24 min⁻¹, indicating high affinity and catalytic efficiency. [1] S-(+)-Marmesin serves as a substrate in a whole-cell bioconversion assay. When added to yeast cultures expressing CYP71AJ1 at a final concentration of 1.0 mM, a significant portion of S-(+)-Marmesin was converted to psoralen within 4 hours. [1] In contrast, the angular analog (S-(+)-Columbianetin) does not serve as a substrate for psoralen synthase but acts as a competitive inhibitor with a Ki of approximately 225 µM. [1] |
| Enzyme Assay |
The enzymatic activity of psoralen synthase (CYP71AJ1mut) was assessed using microsomes isolated from recombinant yeast cells.
Standard assays were conducted in 0.1 M sodium phosphate buffer (pH 7.0) at 27°C for 6 minutes. The reaction mixture (200 µL total) contained 1.0 mM NADPH, varying concentrations of S-(+)-Marmesin (substrate), and 0.3 pmol of enzyme. Reactions were stopped by adding acetonitrile containing concentrated hydrochloric acid (99:1 v/v). The conversion of S-(+)-Marmesin to psoralen was quantified by reverse-phase HPLC using a C18 column. The elution was monitored by diode array detection (220-400 nm) with a gradient of acetonitrile/methanol (1:1) in water/acetic acid. [1] For competitive inhibition assays, the same protocol was used with the addition of S-(+)-Columbianetin at concentrations ranging from 10 to 300 µM to the reaction mixture containing S-(+)-Marmesin. Apparent Km and Ki values were determined by Lineweaver-Burk plot analysis. [1] |
| References |
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| Additional Infomation |
(+)-marmesin is a marmesin. It is an enantiomer of nodakine. Marmesin has been reported in Angelica gigas, Angelica japonica, and other organisms with relevant data. S-(+)-marmesin is a dihydrofuranocoumarin and a key intermediate in the linear furanocoumarin (psoralen) biosynthesis pathway in plants such as celery. It is biosynthesized from desmethylsubebloxin by marmesin synthase, and then converted to psoralen by psoralen synthase (CYP71AJ1) in a cytochrome P450-dependent carbon chain cleavage reaction, which releases acetone. This study confirms that S-(+)-marmesin is a specific precursor for psoralen biosynthesis and is inactive in similar angular furanocoumarin pathways. [1]
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| Molecular Formula |
C14H14O4
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|---|---|
| Molecular Weight |
246.2586
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| Exact Mass |
246.089
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| CAS # |
13849-08-6
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| Related CAS # |
(±)-Marmesin;13710-70-8
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| PubChem CID |
334704
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| Appearance |
White to off-white solid powder
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| Density |
1.3±0.1 g/cm3
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| Boiling Point |
434.0±45.0 °C at 760 mmHg
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| Melting Point |
189-191℃
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| Flash Point |
168.0±22.2 °C
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| Vapour Pressure |
0.0±1.1 mmHg at 25°C
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| Index of Refraction |
1.611
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| LogP |
1.69
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| Hydrogen Bond Donor Count |
1
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| Hydrogen Bond Acceptor Count |
4
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| Rotatable Bond Count |
1
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| Heavy Atom Count |
18
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| Complexity |
387
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| Defined Atom Stereocenter Count |
1
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| SMILES |
CC(C)([C@@H]1CC2=C(O1)C=C3C(=C2)C=CC(=O)O3)O
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| InChi Key |
FWYSBEAFFPBAQU-LBPRGKRZSA-N
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| InChi Code |
InChI=1S/C14H14O4/c1-14(2,16)12-6-9-5-8-3-4-13(15)18-10(8)7-11(9)17-12/h3-5,7,12,16H,6H2,1-2H3/t12-/m0/s1
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| Chemical Name |
(2S)-2-(2-hydroxypropan-2-yl)-2,3-dihydrofuro[3,2-g]chromen-7-one
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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) |
DMSO : ~2 mg/mL (~8.12 mM)
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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 | 4.0607 mL | 20.3037 mL | 40.6075 mL | |
| 5 mM | 0.8121 mL | 4.0607 mL | 8.1215 mL | |
| 10 mM | 0.4061 mL | 2.0304 mL | 4.0607 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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