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Protodioscin (Protodiosgenin)

Cat No.:V72311 Purity: ≥98%
Protodioscin is the main steroidal saponin compound in fenugreek and has multiple effects like anti-lipidemia, anti-tumor, and cardiovascular protection.
Protodioscin (Protodiosgenin)
Protodioscin (Protodiosgenin) Chemical Structure CAS No.: 55056-80-9
Product category: Endogenous Metabolite
This product is for research use only, not for human use. We do not sell to patients.
Size Price Stock Qty
5mg
10mg
25mg
50mg
100mg
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Product Description
Protodioscin is the main steroidal saponin compound in fenugreek and has multiple effects like anti-lipidemia, anti-tumor, and cardiovascular protection.
Biological Activity I Assay Protocols (From Reference)
Targets
Human Endogenous Metabolite
ln Vivo
Significant improvements in glucose intolerance are observed with protodioscin (5 and 10 mg/kg), which also lowers serum levels of UA, BUN, Cr, TC, and TG. By suppressing the activation of nuclear factor-κB, c-Jun N-terminal kinase, p38 mitogen-activated protein kinase, extracellular signal-regulated kinase, and p38, protodioscin dramatically lowers renal concentrations of IL-1β, IL-6, and TNF-α[1]. In rats, protodioscin decreases the number of apoptotic nerve cells brought on by MCAO, lowers the death rate, and prevents the rise in neurological impairment scores and infarct volume. Protodioscin reverses the protein expression of NF-κB (in the nucleus and cytoplasm) and IκBα (in the cytoplasm) induced by MCAO in rats, attenuates the alteration of important apoptins, and reduces the release of pro-inflammatory cytokines in serum[2]. Rats fed a high-fat diet have a coagulation time that is approximately 50% longer than that of rats given a protodioscin injection (0.5 mg/kg, ip). Protodioscin shows promise in reducing blood levels of both lipoproteins, particularly LDL, which raises the HDL/LDL ratio[3].
References

[1]. Protodioscin ameliorates fructose-induced renal injury via inhibition of the mitogen activated protein kinase pathway. Phytomedicine. 2016 Nov 15;23(12):1504-1510.

[2]. Potential neuroprotection of protodioscin against cerebral ischemia-reperfusion injury in rats through intervening inflammation and apoptosis. Steroids. 2016 Sep;113:52-63.

[3]. Antihyperlipidemic effect of protodioscin, an active ingredient isolated from the rhizomes of Dioscorea nipponica. Planta Med. 2010 Oct;76(15):1642-6.

Additional Infomation
Protodioscin is a spirostanyl glycoside that consists of the trisaccharide alpha-L-Rha-(1->4)-[alpha-L-Rha-(1->2)]-beta-D-Glc attached to position 3 of 26-(beta-D-glucopyranosyloxy)-3beta,22-dihydroxyfurost-5-ene via a glycosidic linkage. Found in several plant species including yams, asparagus and funugreek. It has a role as a metabolite. It is a steroid saponin, a trisaccharide derivative, a beta-D-glucoside, a pentacyclic triterpenoid and a cyclic hemiketal. It is functionally related to a diosgenin. It derives from a hydride of a spirostan.
Protodioscin has been reported in Dioscorea collettii, Dioscorea deltoidea, and other organisms with data available.
See also: Fenugreek seed (part of).
These protocols are for reference only. InvivoChem does not independently validate these methods.
Physicochemical Properties
Molecular Formula
C51H84O22
Molecular Weight
1049.20
Exact Mass
1048.545
CAS #
55056-80-9
PubChem CID
441891
Appearance
White to off-white solid powder
Density
1.5±0.1 g/cm3
Index of Refraction
1.632
LogP
3.64
Hydrogen Bond Donor Count
13
Hydrogen Bond Acceptor Count
22
Rotatable Bond Count
14
Heavy Atom Count
73
Complexity
1900
Defined Atom Stereocenter Count
31
SMILES
C[C@H]1[C@H]2[C@H](C[C@@H]3[C@@]2(CC[C@H]4[C@H]3CC=C5[C@@]4(CC[C@@H](C5)O[C@H]6[C@@H]([C@H]([C@@H]([C@H](O6)CO)O[C@H]7[C@@H]([C@@H]([C@H]([C@@H](O7)C)O)O)O)O)O[C@H]8[C@@H]([C@@H]([C@H]([C@@H](O8)C)O)O)O)C)C)O[C@@]1(CC[C@@H](C)CO[C@H]9[C@@H]([C@H]([C@@H]([C@H](O9)CO)O)O)O)O
InChi Key
LVTJOONKWUXEFR-UEZXSUPNSA-N
InChi Code
InChI=1S/C51H84O22/c1-20(19-65-45-39(60)38(59)35(56)30(17-52)69-45)9-14-51(64)21(2)32-29(73-51)16-28-26-8-7-24-15-25(10-12-49(24,5)27(26)11-13-50(28,32)6)68-48-44(72-47-41(62)37(58)34(55)23(4)67-47)42(63)43(31(18-53)70-48)71-46-40(61)36(57)33(54)22(3)66-46/h7,20-23,25-48,52-64H,8-19H2,1-6H3/t20-,21+,22+,23+,25+,26-,27+,28+,29+,30-,31-,32+,33+,34+,35-,36-,37-,38+,39-,40-,41-,42+,43-,44-,45-,46+,47+,48-,49+,50+,51-/m1/s1
Chemical Name
(2S,3R,4R,5R,6S)-2-[(2R,3S,4S,5R,6R)-4-hydroxy-2-(hydroxymethyl)-6-[[(1S,2S,4S,6R,7S,8R,9S,12S,13R,16S)-6-hydroxy-7,9,13-trimethyl-6-[(3R)-3-methyl-4-[(2R,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxybutyl]-5-oxapentacyclo[10.8.0.02,9.04,8.013,18]icos-18-en-16-yl]oxy]-5-[(2S,3R,4R,5R,6S)-3,4,5-trihydroxy-6-methyloxan-2-yl]oxyoxan-3-yl]oxy-6-methyloxane-3,4,5-triol
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

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)
H2O: 50 mg/mL (47.66 mM)
DMSO: 50 mg/mL (47.66 mM)
Solubility (In Vivo)
Solubility in Formulation 1: ≥ 2.5 mg/mL (2.38 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 (2.38 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 (2.38 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 0.9531 mL 4.7655 mL 9.5311 mL
5 mM 0.1906 mL 0.9531 mL 1.9062 mL
10 mM 0.0953 mL 0.4766 mL 0.9531 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 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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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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