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Strictosidinic acid

Cat No.:V71177 Purity: ≥98%
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
Strictosidinic acid Chemical Structure CAS No.: 150148-81-5
Product category: 5-HT Receptor
This product is for research use only, not for human use. We do not sell to patients.
Size Price Stock Qty
1mg
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Product Description
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.
Strictosidinic acid is a naturally occurring glycosidic monoterpene indole alkaloid (MIA) isolated from the leaves of Psychotria myriantha. It has a molecular formula of C26H32N2O9 and a molecular weight of 516.54. It is an orally active compound that inhibits the precursor enzyme of 5-HT biosynthesis and reduces 5-HT content. It exhibits peripheral analgesic and antipyretic activity in mice and serves as a key biosynthetic intermediate in the camptothecin pathway.
Biological Activity I Assay Protocols (From Reference)
Targets
5-HT Receptor
Strictosidinic acid targets the 5-HT (serotonin) receptor pathway. It functions as a selective 5-HT biosynthesis inhibitor by inhibiting the precursor enzyme of 5-HT synthesis, leading to reduced serotonin levels. It has no acetylcholinesterase (AChE) activity, enabling clean serotonergic targeting without cholinergic confounds. It belongs to the secologanin-derived tryptamine-iridoid class.
ln Vitro
In vitro, Strictosidinic acid demonstrates antiradical activity against DPPH with an EC50 of 27.68 μM, which is superior to barakol (39.62 μM). It shows no AChE activity, making it a selective tool for studying serotonergic pathways. The compound's DPPH radical scavenging activity indicates its potential as an antioxidant. It has a promising effect in the central nervous system.
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.
In vivo, Strictosidinic acid causes a significant 83.5% reduction in 5-HT levels following intra-hippocampal injection (20 µg/µl) in male Wistar rats. Intraperitoneal administration (10 mg/kg) causes a 63.4% reduction in 5-HT levels and a 67.4% reduction in DOPAC values. It exhibits peripheral analgesic and antipyretic activity in mice without causing central nervous system sedation. The compound shows promise for research in the central nervous system.
Enzyme Assay
For non-cell-based assays, Strictosidinic acid can be evaluated for its DPPH radical scavenging activity using a standard antioxidant assay. The compound is incubated with DPPH solution at various concentrations, and the decrease in absorbance at 517 nm is measured to calculate the EC50 value. For receptor binding studies, radioligand binding displacement assays using membrane preparations from cells expressing 5-HT receptors can be performed with a suitable radiolabeled ligand. Membrane homogenates are incubated with increasing concentrations of the test compound and a fixed concentration of the radioligand, followed by filtration and scintillation counting.
Cell Assay
For in vitro cellular assays, cells expressing 5-HT receptors or serotonergic neurons can be cultured in appropriate media. To assess the compound's effect on serotonin levels, cells are treated with various concentrations of Strictosidinic acid, and 5-HT content is measured using HPLC or ELISA-based detection. The compound's antioxidant activity can be assessed in cell-based oxidative stress models by measuring reactive oxygen species (ROS) levels using fluorescent probes. Cytotoxicity is assessed using MTT or LDH assays to ensure that observed effects are not due to cell death.
Animal Protocol
For in vivo animal studies, Strictosidinic acid is typically administered to male Wistar rats (weighing 200-250 g) via intra-hippocampal injection (20 µg/µl) or intraperitoneal injection (10 mg/kg). Following administration, brain tissue (hippocampus or striatum) is collected, and 5-HT and DOPAC levels are measured using HPLC. For analgesic and antipyretic studies, the compound is administered to mice, and pain responses and body temperature are monitored. Dosing regimens vary depending on the specific model and desired exposure levels.
ADME/Pharmacokinetics
Strictosidinic acid is an orally active compound with a molecular weight of 516.54 and a molecular formula of C26H32N2O9. It is slightly soluble in water (4 g/L at 25°C) and has a density of 1.50±0.1 g/cm3. The compound should be stored at 4°C under nitrogen. In solvent, it can be stored at -80°C for 6 months or at -20°C for 1 month under nitrogen. It is supplied as a powder with ≥98% purity.
Toxicity/Toxicokinetics
The toxicity profile of Strictosidinic acid has not been extensively reported. As a naturally occurring alkaloid with serotonin-lowering effects, potential adverse effects may include modulation of serotonergic signaling, which could affect mood, appetite, and sleep regulation. The compound is for research use only and is not intended for human consumption. Standard toxicological evaluation would include acute and repeated-dose toxicity studies, as well as assessment of effects on the central nervous system and serotonergic function.
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
According to reports, strictonucleotides have been found in Ceylon Hunter, Umbrella Hunter, and other organisms with available data.
Strictosidinic acid (CAS 150148-81-5) is a naturally occurring glycosidic monoterpene indole alkaloid isolated from Psychotria myriantha leaves. It serves as a key biosynthetic intermediate in the camptothecin pathway in plants such as Camptotheca acuminata. The compound is characterized by a β-D-glucopyranosyl moiety attached to a strictosidine-derived scaffold. It has been studied for its serotonin-lowering effects and potential applications in central nervous system research. It is available for research purposes only.
These protocols are for reference only. InvivoChem does not independently validate these methods.
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)
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 : PEG300Tween 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).
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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 : PEG300Tween 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).
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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.

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What is the mass of compound required to make a 10 mM stock solution in 5 ml of DMSO given that the molecular weight of the compound is 350.26 g/mol?
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What volume of a given 10 mM stock solution is required to make 25 ml of a 25 μM solution?
Using the equation C1V1 = C2V2, where C1=10 mM, C2=25 μM, V2=25 ml and V1 is the unknown:
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g/mol

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Note: Chemical formula is case sensitive: C12H18N3O4  c12h18n3o4
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In vivo Formulation Calculator (Clear solution)
Step 1: Enter information below (Recommended: An additional animal to make allowance for loss during the experiment)
Step 2: Enter in vivo formulation (This is only a calculator, not the exact formulation for a specific product. Please contact us first if there is no in vivo formulation in the solubility section.)
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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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