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Strictosidinic acid 150148-81-5

Strictosidinic acid 150148-81-5

CAS No.: 150148-81-5

Strictosidinic acid is an orally bioactive glycoside indole monoterpene alkaloid extracted from the leaves of Psychotria
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Strictosidinic acid is an orally bioactive glycoside indole monoterpene alkaloid extracted from the leaves of Psychotria myriantha, which inhibits the precursor enzymes of 5-HT biosynthesis and reduces 5-HT content. Strictosidinic acid has peripheral analgesic and antipyretic activity in mice.

Physicochemical Properties


Molecular Formula C26H32N2O9
Molecular Weight 516.54
Exact Mass 516.21
CAS # 150148-81-5
PubChem CID 21586927
Appearance Light yellow to yellow solid powder
Density 1.5±0.1 g/cm3
Boiling Point 792.8±60.0 °C at 760 mmHg
Flash Point 433.3±32.9 °C
Vapour Pressure 0.0±2.9 mmHg at 25°C
Index of Refraction 1.692
LogP -0.23
Hydrogen Bond Donor Count 7
Hydrogen Bond Acceptor Count 10
Rotatable Bond Count 7
Heavy Atom Count 37
Complexity 871
Defined Atom Stereocenter Count 9
SMILES

C=C[C@@H]1[C@@H](C(=CO[C@H]1O[C@H]2[C@@H]([C@H]([C@@H]([C@H](O2)CO)O)O)O)C(=O)O)C[C@H]3C4=C(CCN3)C5=CC=CC=C5N4

InChi Key CMMIVMFGFIBAGC-IUNANRIWSA-N
InChi Code

InChI=1S/C26H32N2O9/c1-2-12-15(9-18-20-14(7-8-27-18)13-5-3-4-6-17(13)28-20)16(24(33)34)11-35-25(12)37-26-23(32)22(31)21(30)19(10-29)36-26/h2-6,11-12,15,18-19,21-23,25-32H,1,7-10H2,(H,33,34)/t12-,15+,18+,19-,21-,22+,23-,25+,26+/m1/s1
Chemical Name

(2S,3R,4S)-3-ethenyl-4-[[(1S)-2,3,4,9-tetrahydro-1H-pyrido[3,4-b]indol-1-yl]methyl]-2-[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy-3,4-dihydro-2H-pyran-5-carboxylic acid
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

Note: Please store this product in a sealed and protected environment (e.g. under nitrogen), avoid exposure to moisture.
Shipping Condition Room temperature (This product is stable at ambient temperature for a few days during ordinary shipping and time spent in Customs)

Biological Activity


Targets 5-HT Receptor
ln Vivo When administered intrahippocampally, streptosidinic acid (20 μg/μl) significantly lowers 5-HT levels by 83.5%. Male Wistar rats weighing 200–250 g show a 63.4% reduction in 5-HT levels and a 67.4% reduction in DOPAC values when exposed to 10 mg/kg; ip] streptosidinic acid.
References

[1]. Strictosidinic Acid, Isolated From Psychotria Myriantha Mull. Arg. (Rubiaceae), Decreases Serotonin Levels in Rat Hippocampus. Fitoterapia. 2012 Sep;83(6):1138-43.

[2]. Monoamine Levels in Rat Striatum After Acute Intraperitoneal Injection of Strictosidinic Acid Isolated From Psychotria Myriantha Mull. Arg. (Rubiaceae). Phytomedicine. 2010 Mar;17(3-4):289-91.

Additional Infomation Strictosidinic acid has been reported in Hunteria zeylanica, Hunteria umbellata, and other organisms with data available.

Solubility Data


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
(e.g. IP/IV/IM/SC)
Injection Formulation 1: DMSO : Tween 80: Saline = 10 : 5 : 85 (i.e. 100 μL DMSO stock solution 50 μL Tween 80 850 μL Saline)
*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).
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)]
*Preparation of 20% SBE-β-CD in Saline (4°C,1 week): Dissolve 2 g SBE-β-CD in 10 mL saline to obtain a clear solution.
Injection Formulation 5: 2-Hydroxypropyl-β-cyclodextrin : Saline = 50 : 50 (i.e. 500 μL 2-Hydroxypropyl-β-cyclodextrin 500 μL Saline)
Injection Formulation 6: DMSO : PEG300 : castor oil : Saline = 5 : 10 : 20 : 65 (i.e. 50 μL DMSO 100 μLPEG300 200 μL castor oil 650 μL Saline)
Injection Formulation 7: Ethanol : Cremophor : Saline = 10: 10 : 80 (i.e. 100 μL Ethanol 100 μL Cremophor 800 μL Saline)
Injection Formulation 8: Dissolve in Cremophor/Ethanol (50 : 50), then diluted by Saline
Injection Formulation 9: EtOH : Corn oil = 10 : 90 (i.e. 100 μL EtOH 900 μL Corn oil)
Injection Formulation 10: EtOH : PEG300:Tween 80 : Saline = 10 : 40 : 5 : 45 (i.e. 100 μL EtOH 400 μLPEG300 50 μL Tween 80 450 μL 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).
Oral Formulation 3: Dissolved in PEG400
Oral Formulation 4: Suspend in 0.2% Carboxymethyl cellulose
Oral Formulation 5: Dissolve in 0.25% Tween 80 and 0.5% Carboxymethyl cellulose
Oral Formulation 6: Mixing with food powders

Note: Please be aware that the above formulations are for reference only. InvivoChem strongly recommends customers to read literature methods/protocols carefully before determining which formulation you should use for in vivo studies, as different compounds have different solubility properties and have to be formulated differently.

 (Please use freshly prepared in vivo formulations for optimal results.)
Preparing Stock Solutions 1 mg 5 mg 10 mg
1 mM 1.9360 mL 9.6798 mL 19.3596 mL
5 mM 0.3872 mL 1.9360 mL 3.8719 mL
10 mM 0.1936 mL 0.9680 mL 1.9360 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.