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Plantainoside D

Cat No.:V60019 Purity: ≥98%
Plantainoside D has ACE inhibitory activity (IC50 2.17 mM).
Plantainoside D
Plantainoside D Chemical Structure CAS No.: 147331-98-4
Product category: New4
This product is for research use only, not for human use. We do not sell to patients.
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5mg
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Product Description
Plantainoside D has ACE inhibitory activity (IC50 2.17 mM). At the same time, Plantainoside D is also an IKK-β inhibitor.
Plantainoside D (CAS 147331-98-4), also known as Isoplantamajoside, is a phenylethanoid glycoside isolated from Plantago asiatica L. (Asiatic plantain). It exhibits potent antioxidative effects comparable to those of ascorbic acid and functions as an inhibitor of angiotensin-converting enzyme (ACE, IC50 = 2.17 mM), IKK-β, and PKCα (IC50 = 14.8 μM). Plantainoside D also reduces glutamate release in the rat cerebral cortex and alleviates cell apoptosis through inhibition of ROS and NF-κB activation.
Biological Activity I Assay Protocols (From Reference)
Targets
Plantainoside D targets multiple enzymes and signaling pathways. It inhibits angiotensin-converting enzyme (ACE) with an IC50 of 2.17 mM, suggesting potential for blood pressure regulation. It also functions as an IKK-β inhibitor, which is a key regulator of NF-κB signaling and inflammation. Additionally, it inhibits PKCα with an IC50 of 14.8 μM. The compound reduces glutamate release and alleviates cell apoptosis through inhibition of ROS and NF-κB activation.
ln Vitro
In vitro, Plantainoside D shows ACE inhibitory activity with an IC50 of 2.17 mM. It also exhibits inhibitory activity against PKCα with an IC50 of 14.8 μM. The compound shows potent antioxidative effects comparable to those of ascorbic acid. It significantly reduces glutamate release in the rat cerebral cortex and alleviates cell apoptosis through inhibition of ROS and NF-κB activation. Plantainoside D is also a promising IKK-β inhibitor.
ln Vivo
In vivo, Plantainoside D significantly improves acute lung injury (ALI) induced by sepsis by regulating the Sirt3/NLRP3 signaling pathway. This suggests potential therapeutic applications in inflammatory lung conditions. Its anti-inflammatory and antioxidant properties suggest potential for in vivo studies in models of inflammation, oxidative stress, and cardiovascular disease. However, specific detailed in vivo protocols for this compound are limited in the available literature.
Enzyme Assay
The ACE inhibitory activity is assessed using a fluorometric or colorimetric enzyme assay. ACE enzyme is incubated with a synthetic substrate (e.g., hippuryl-histidyl-leucine) and various concentrations of Plantainoside D. The reaction product is measured, and IC50 values are calculated from dose-response curves. IKK-β inhibitory activity is assessed using kinase assays with appropriate substrates. PKCα inhibitory activity is measured using kinase activity assays. Antioxidant activity is assessed using DPPH or ABTS radical scavenging assays.
Cell Assay
For cellular studies, various cell lines (e.g., neuronal cells, lung epithelial cells, immune cells) are cultured in appropriate media. Cells are treated with Plantainoside D at various concentrations for 24-72 hours. Cell viability is assessed using MTT or similar assays. ROS levels are measured using DCFH-DA. NF-κB activation is assessed by Western blot for p65 phosphorylation or by luciferase reporter assays. Glutamate release is measured in cerebral cortex slices using HPLC or fluorometric assays. Apoptosis is evaluated by flow cytometry.
Animal Protocol
In vivo studies for Plantainoside D are conducted in sepsis-induced acute lung injury (ALI) models. Mice are subjected to sepsis induction (e.g., cecal ligation and puncture or LPS administration), followed by treatment with Plantainoside D. Lung injury is assessed by measuring wet/dry weight ratio, inflammatory cell infiltration in bronchoalveolar lavage fluid, and histopathological examination. The Sirt3/NLRP3 signaling pathway is analyzed by Western blot. The compound is typically administered via intraperitoneal injection or oral gavage.
ADME/Pharmacokinetics
Specific pharmacokinetic data for Plantainoside D are not reported. As a glycoside, the compound is expected to have limited oral bioavailability due to poor membrane permeability and extensive intestinal metabolism. Pharmacokinetic studies would be required to determine parameters such as half-life, Cmax, and bioavailability. The compound is typically stored as a powder at -20°C and protected from light.
Toxicity/Toxicokinetics
As a natural product from Plantago asiatica, which has traditional medicinal uses, Plantainoside D is generally considered to have a moderate safety profile. The compound shows potent antioxidative effects comparable to ascorbic acid, suggesting potential benefits. However, 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]. Geng F, Yang L, Chou G, Wang Z. Bioguided isolation of angiotensin-converting enzyme inhibitors from the seeds of Plantago asiatica L. Phytother Res. 2010;24(7):1088-1094.

[2]. Zhou P, Hua F, Wang X, Huang JL. Therapeutic potential of IKK-β inhibitors from natural phenolics for inflammation in cardiovascular diseases. Inflammopharmacology. 2020;28(1):19-37.

Additional Infomation
According to reports, plantain, Asian plantain, and other organisms with available data contain plantain glycoside D.
Plantainoside D is a phenylethanoid glycoside from Plantago asiatica that inhibits ACE (IC50 = 2.17 mM), IKK-β, and PKCα (IC50 = 14.8 μM). It shows potent antioxidant effects comparable to ascorbic acid and improves sepsis-induced ALI by regulating Sirt3/NLRP3. 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
C29H36O16
Molecular Weight
640.586550712585
Exact Mass
640.2
CAS #
147331-98-4
PubChem CID
9986606
Appearance
White to light yellow solid powder
LogP
-1
Hydrogen Bond Donor Count
10
Hydrogen Bond Acceptor Count
16
Rotatable Bond Count
12
Heavy Atom Count
45
Complexity
953
Defined Atom Stereocenter Count
10
SMILES
O([C@H]1[C@@H]([C@H]([C@@H]([C@@H](CO)O1)O)O)O)[C@@H]1[C@H]([C@H](OCCC2C=CC(=C(C=2)O)O)O[C@H](COC(/C=C/C2C=CC(=C(C=2)O)O)=O)[C@H]1O)O
InChi Key
CBZYUWGJNYOKHT-ZKDZFUIGSA-N
InChi Code
InChI=1S/C29H36O16/c30-11-19-22(36)24(38)25(39)29(43-19)45-27-23(37)20(12-42-21(35)6-3-13-1-4-15(31)17(33)9-13)44-28(26(27)40)41-8-7-14-2-5-16(32)18(34)10-14/h1-6,9-10,19-20,22-34,36-40H,7-8,11-12H2/b6-3+/t19-,20-,22-,23-,24+,25-,26-,27+,28-,29+/m1/s1
Chemical Name
[(2R,3R,4S,5R,6R)-6-[2-(3,4-dihydroxyphenyl)ethoxy]-3,5-dihydroxy-4-[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxyoxan-2-yl]methyl (E)-3-(3,4-dihydroxyphenyl)prop-2-enoate
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 : ~250 mg/mL (~390.27 mM)
Solubility (In Vivo)
Solubility in Formulation 1: ≥ 2.08 mg/mL (3.25 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 20.8 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.

Solubility in Formulation 2: ≥ 2.08 mg/mL (3.25 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 20.8 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 1.5611 mL 7.8053 mL 15.6106 mL
5 mM 0.3122 mL 1.5611 mL 3.1221 mL
10 mM 0.1561 mL 0.7805 mL 1.5611 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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Note: Chemical formula is case sensitive: C12H18N3O4  c12h18n3o4
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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.
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