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Hastatoside

Alias: Hastatoside
Cat No.:V60031 Purity: ≥98%
Hastatoside is an iridoid glycoside extracted from Verbena officinalis and has sleep-promoting effects.
Hastatoside
Hastatoside Chemical Structure CAS No.: 50816-24-5
Product category: New4
This product is for research use only, not for human use. We do not sell to patients.
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Product Description
Hastatoside is an iridoid glycoside extracted from Verbena officinalis and has sleep-promoting effects.
Hastatoside (CAS 50816-24-5), also known as 5-Hydroxyverbenalin, is an iridoid glycoside and a characteristic constituent of Verbena officinalis L. (vervain). It is a major sleep-promoting component of V. officinalis and exhibits anti-inflammatory, antioxidant, and hepatoprotective activities. Hastatoside increases the total time of non-rapid eye movement (NREM) sleep and increases delta activity during NREM sleep.
Biological Activity I Assay Protocols (From Reference)
Targets
Hastatoside targets the central nervous system to promote sleep, specifically increasing non-rapid eye movement (NREM) sleep and delta activity. Its anti-inflammatory activity suggests effects on inflammatory pathways. The compound's antioxidant and hepatoprotective activities indicate modulation of oxidative stress pathways. As an iridoid glycoside, it may interact with various cellular targets involved in sleep regulation, inflammation, and oxidative stress.
ln Vitro
In vitro, Hastatoside has anti-inflammatory activity. It exhibits antioxidant and hepatoprotective properties. Specific IC50 values or detailed mechanistic data are not extensively reported in the available literature. As a sleep-promoting compound, its in vitro activities may include modulation of GABAergic or other neurotransmitter systems. The compound's iridoid glycoside structure suggests potential interactions with various cellular receptors or enzymes.
ln Vivo
Hastatoside (0.32-0.64 mmol/kg; oral; 9-hour duration; male rats of the Sprague-Dawley strain) treatment increased the total duration of non-rapid eye movement sleep over 9 hours, with a lag time of approximately 3-5 hours post-dose , 20:00 (lights out time). Hastatoside also increases delta activity during non-rapid eye movement sleep [1].
In vivo, Hastatoside (0.32-0.64 mmol/kg) increases the total time of non-rapid eye movement sleep during a 9-hour period, with a lag time of about 3-5 hours after administration. It also increases delta activity during NREM sleep. These effects confirm its role as a major sleep-promoting component of Verbena officinalis. The compound's anti-inflammatory, antioxidant, and hepatoprotective activities suggest potential for in vivo studies in inflammation and liver disease models.
Enzyme Assay
The sleep-promoting activity is assessed using electroencephalography (EEG) and electromyography (EMG) recordings in animal models. Hastatoside is administered via oral gavage or intraperitoneal injection, and sleep-wake cycles are monitored. The total time of NREM sleep and delta activity during NREM sleep are quantified. Anti-inflammatory activity is assessed using standard in vitro assays such as measuring cytokine production in LPS-stimulated immune cells. Antioxidant activity is assessed using DPPH or ABTS assays.
Cell Assay
For cellular studies, immune cells (e.g., macrophages, microglia) and hepatocyte cell lines are cultured in appropriate media. Cells are treated with Hastatoside at various concentrations (e.g., 0.1-100 μM) for 24-72 hours. Cell viability is assessed using MTT or similar assays. Inflammatory cytokine levels (TNF-α, IL-6, IL-1β) are measured by ELISA. ROS levels are measured using DCFH-DA. The compound is typically dissolved in DMSO and diluted in culture media, with a final DMSO concentration ≤0.1%.
Animal Protocol
Animal/Disease Models: Male SD (SD (Sprague-Dawley)) strain rat (8 weeks old; 260-280 g) [1]
Doses: 0.32 mmol/kg, 0.48 mmol/kg, 0.64 mmol/kg
Route of Administration: oral; . 9-hour
Experimental Results: Total time in non-rapid eye movement sleep increased over 9 hrs (hrs (hours)), with a lag time of approximately 3-5 hrs (hrs (hours)) after dosing at 20:00 (lights-out time). Delta activity during non-rapid eye movement sleep was also increased.
In vivo studies for Hastatoside are conducted in rodent models. For sleep studies, rats or mice are implanted with EEG and EMG electrodes. Hastatoside is administered at 0.32-0.64 mmol/kg via oral gavage or intraperitoneal injection. Sleep-wake states are scored based on EEG and EMG signals. For anti-inflammatory studies, models of inflammation (e.g., LPS-induced systemic inflammation) are used. For hepatoprotection studies, liver injury models (e.g., CCl₄-induced) are employed. Endpoints include inflammatory markers, liver enzymes, and histopathology.
ADME/Pharmacokinetics
Specific pharmacokinetic data for Hastatoside are not extensively reported. The compound has a molecular weight of 404.37 g/mol. As a glycoside, the compound is expected to have limited oral bioavailability due to poor membrane permeability and extensive intestinal metabolism. The lag time of 3-5 hours for sleep-promoting effects suggests the compound or its metabolites may require time to reach effective concentrations in the brain. Pharmacokinetic studies would be required to determine absorption and metabolism.
Toxicity/Toxicokinetics
As a natural product from Verbena officinalis, which has traditional medicinal uses as a sleep aid and anti-inflammatory agent, Hastatoside is generally considered to have a moderate safety profile. The compound's sleep-promoting effects suggest central nervous system activity that should be carefully evaluated. Comprehensive toxicology studies including acute, subchronic, and genotoxicity assessments have not been reported. The compound should be handled with appropriate safety precautions in laboratory settings.
References

[1]. Hastatoside and verbenalin are sleep-promoting.

Additional Infomation
Hastatoside is an iridoid monoterpene compound with the molecular formula C17H24O11, isolated from various plants including Verbena officinalis, and has sleep-promoting effects. It is a plant metabolite and hepatoprotective agent. It is a β-D-glucoside, iridoid monoterpene compound, cyclopentapran compound, monosaccharide derivative, monoterpene glycoside, α,β-unsaturated carboxylic acid ester, and methyl ester. Hastatoside has been reported to exist in Penstemon secundiflorus, Penstemon nitidus, and several other organisms with relevant data.
Hastatoside is an iridoid glycoside from Verbena officinalis that is a major sleep-promoting component. It increases NREM sleep time and delta activity and exhibits anti-inflammatory, antioxidant, and hepatoprotective activities. No clinical trials exist. For research use only.
These protocols are for reference only. InvivoChem does not independently validate these methods.
Physicochemical Properties
Molecular Formula
C17H24O11
Molecular Weight
404.3659
Exact Mass
404.131
CAS #
50816-24-5
PubChem CID
92043450
Appearance
White to off-white solid powder
Density
1.6±0.1 g/cm3
Boiling Point
653.5±55.0 °C at 760 mmHg
Flash Point
234.8±25.0 °C
Vapour Pressure
0.0±4.5 mmHg at 25°C
Index of Refraction
1.613
LogP
-2.38
Hydrogen Bond Donor Count
5
Hydrogen Bond Acceptor Count
11
Rotatable Bond Count
5
Heavy Atom Count
28
Complexity
664
Defined Atom Stereocenter Count
9
SMILES
C[C@H]1CC(=O)[C@]2([C@@H]1[C@@H](OC=C2C(=O)OC)O[C@H]3[C@@H]([C@H]([C@@H]([C@H](O3)CO)O)O)O)O
InChi Key
PRZVXHGUJJPSME-CZMSZWGTSA-N
InChi Code
InChI=1S/C17H24O11/c1-6-3-9(19)17(24)7(14(23)25-2)5-26-15(10(6)17)28-16-13(22)12(21)11(20)8(4-18)27-16/h5-6,8,10-13,15-16,18,20-22,24H,3-4H2,1-2H3/t6-,8+,10-,11+,12-,13+,15-,16-,17+/m0/s1
Chemical Name
methyl (1S,4aR,7S,7aR)-4a-hydroxy-7-methyl-5-oxo-1-[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy-1,6,7,7a-tetrahydrocyclopenta[c]pyran-4-carboxylate
Synonyms
Hastatoside
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: This product requires protection from light (avoid light exposure) during transportation and storage.
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)
DMSO : ~100 mg/mL (~247.30 mM)
Solubility (In Vivo)
Solubility in Formulation 1: ≥ 2.5 mg/mL (6.18 mM) (saturation unknown) in 10% DMSO + 40% PEG300 + 5% Tween80 + 45% Saline (add these co-solvents sequentially from left to right, and one by one), clear solution.
For example, if 1 mL of working solution is to be prepared, you can add 100 μL of 25.0 mg/mL clear DMSO stock solution to 400 μL PEG300 and mix evenly; then add 50 μL Tween-80 to the above solution and mix evenly; then add 450 μL normal saline to adjust the volume to 1 mL.
Preparation of saline: Dissolve 0.9 g of sodium chloride in 100 mL ddH₂ O to obtain a clear solution.

Solubility in Formulation 2: ≥ 2.5 mg/mL (6.18 mM) (saturation unknown) in 10% DMSO + 90% (20% SBE-β-CD in Saline) (add these co-solvents sequentially from left to right, and one by one), clear solution.
For example, if 1 mL of working solution is to be prepared, you can add 100 μL of 25.0 mg/mL clear DMSO stock solution to 900 μL of 20% SBE-β-CD physiological saline solution and mix evenly.
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.

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Solubility in Formulation 3: ≥ 2.5 mg/mL (6.18 mM) (saturation unknown) in 10% DMSO + 90% Corn Oil (add these co-solvents sequentially from left to right, and one by one), clear solution.
For example, if 1 mL of working solution is to be prepared, you can add 100 μL of 25.0 mg/mL clear DMSO stock solution to 900 μL of corn oil and mix evenly.


 (Please use freshly prepared in vivo formulations for optimal results.)
Preparing Stock Solutions 1 mg 5 mg 10 mg
1 mM 2.4730 mL 12.3649 mL 24.7298 mL
5 mM 0.4946 mL 2.4730 mL 4.9460 mL
10 mM 0.2473 mL 1.2365 mL 2.4730 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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In vivo Formulation Calculator (Clear solution)
Step 1: Enter information below (Recommended: An additional animal to make allowance for loss during the experiment)
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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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