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Pseudoprotodioscin

CAS# 102115-79-7

Pseudoprotodioscin

2D Structure

Catalog No. BCN2827----Order now to get a substantial discount!

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3D structure

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Pseudoprotodioscin

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Chemical Properties of Pseudoprotodioscin

Cas No. 102115-79-7 SDF Download SDF
PubChem ID 51346147 Appearance Powder
Formula C51H82O2 M.Wt 727.2
Type of Compound Steroids Storage Desiccate at -20°C
Solubility Soluble in Chloroform,Dichloromethane,Ethyl Acetate,DMSO,Acetone,etc.
Chemical Name (2S,3R,4R,5R,6S)-2-[(2R,3S,4S,5R,6R)-4-hydroxy-2-(hydroxymethyl)-5-[(2S,3R,4R,5R,6S)-3,4,5-trihydroxy-6-methyloxan-2-yl]oxy-6-[[(1S,2S,4S,8S,9S,12S,13R)-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]icosa-6,18-dien-16-yl]oxy]oxan-3-yl]oxy-6-methyloxane-3,4,5-triol
SMILES CC1C(C(C(C(O1)OC2C(OC(C(C2O)OC3C(C(C(C(O3)C)O)O)O)OC4CCC5(C6CCC7(C(C6CC=C5C4)CC8C7C(=C(O8)CCC(C)COC9C(C(C(C(O9)CO)O)O)O)C)C)C)CO)O)O)O
Standard InChIKey MDCUMTGKKLOMCW-MQDUZHDNSA-N
Standard InChI InChI=1S/C51H82O21/c1-20(19-64-46-40(60)39(59)36(56)31(17-52)69-46)7-10-29-21(2)33-30(68-29)16-28-26-9-8-24-15-25(11-13-50(24,5)27(26)12-14-51(28,33)6)67-49-45(72-48-42(62)38(58)35(55)23(4)66-48)43(63)44(32(18-53)70-49)71-47-41(61)37(57)34(54)22(3)65-47/h8,20,22-23,25-28,30-49,52-63H,7,9-19H2,1-6H3/t20-,22+,23+,25?,26-,27+,28+,30+,31-,32-,33+,34+,35+,36-,37-,38-,39+,40-,41-,42-,43+,44-,45-,46-,47+,48+,49-,50+,51+/m1/s1
General tips For obtaining a higher solubility , please warm the tube at 37 ℃ and shake it in the ultrasonic bath for a while.Stock solution can be stored below -20℃ for several months.
We recommend that you prepare and use the solution on the same day. However, if the test schedule requires, the stock solutions can be prepared in advance, and the stock solution must be sealed and stored below -20℃. In general, the stock solution can be kept for several months.
Before use, we recommend that you leave the vial at room temperature for at least an hour before opening it.
About Packaging 1. The packaging of the product may be reversed during transportation, cause the high purity compounds to adhere to the neck or cap of the vial.Take the vail out of its packaging and shake gently until the compounds fall to the bottom of the vial.
2. For liquid products, please centrifuge at 500xg to gather the liquid to the bottom of the vial.
3. Try to avoid loss or contamination during the experiment.
Shipping Condition Packaging according to customer requirements(5mg, 10mg, 20mg and more). Ship via FedEx, DHL, UPS, EMS or other couriers with RT, or blue ice upon request.

Source of Pseudoprotodioscin

The rhizomes of Dioscorea nipponica Makino.

Biological Activity of Pseudoprotodioscin

DescriptionPseudoprotodioscin exhibits anti-inflammatory and anticancer activities, it shows a weaker suppressing effect on the production of inflammatory cytokines, and can suppress melanogenesis in B16F1 cells.
TargetsImmunology & Inflammation related
In vitro

Anti-inflammatory and anti-melanogenic steroidal saponin glycosides from Fenugreek (Trigonella foenum-graecum L.) seeds.[Pubmed: 20979021 ]

Planta Med. 2011 May;77(7):705-10.

Fenugreek seed ( Trigonella foenum-graecum L.) is used as an herbal medicine for treating metabolic and nutritive dysfunctions.
METHODS AND RESULTS:
To determine if this plant has other beneficial effects, we tested the inhibitory activities of a methanol (MeOH) extract of fenugreek seed on the production of inflammatory cytokines and melanin synthesis in cultured cell lines in vitro. The MeOH extract inhibited the production of phorbol-12-myristate-13-acetate-induced inflammatory cytokines such as tumor necrosis factor (TNF)-α in cultured THP-1 cells, and also restrained the intracellular synthesis of melanin in murine melanoma B16F1 cells. We isolated three active constituents from fenugreek seed extracts. These were identified as the steroidal saponins 26- O-β-D-glucopyranosyl-(25 R)-furost-5(6)-en-3 β,22 β,26-triol-3- O-α-L-rhamno-pyranosyl-(1'' → 2')-O-[β-D-glucopyranosyl-(1''' → 6')- O]-β-D-glucopyranoside 1, minutoside B 2, and Pseudoprotodioscin 3. Compounds 1 and 2 strongly suppressed the production of inflammatory cytokines, whereas 3 showed a weaker suppressing effect. Melanogenesis in B16F1 cells was significantly suppressed by 1 and 3, and weakly suppressed by 2. All three compounds showed moderate cytotoxicities.
CONCLUSIONS:
These results indicate that fenugreek extract and its active constituents could protect against skin damage.

Two new steroidal saponins from the rhizomes of Dioscorea panthaica and their cytotoxic activity.[Pubmed: 11745024]

Planta Med. 2001 Dec;67(9):853-7.

Two new steroidal saponins, dioscoresides C (1) and D (2), along with a new natural product, pregnadienolone 3-O-beta-gracillimatriose (3), and two known compounds, pregnadienolone 3-O-beta-chacotrioside (4) and Pseudoprotodioscin (5), were isolated from the rhizomes of Dioscorea panthaica Prain et Burkill.
METHODS AND RESULTS:
On the basis of extensive NMR studies and chemical evidence, dioscoresides C and D were determined to be 26-O-beta-D-glucopyranosyl-3 beta,26-dihydroxy-23(S)-methoxy-25(R)-furosta-5,20(22)-dien-3-O-alpha-L-rhamnopyranosyl-(1-->2)-[alpha-L-rhamnopyranosyl-(1-->4)]-beta-D-glucopyranoside and 26-O-beta-D-glucopyranosyl-3 beta,26-dihydroxy-20,22-seco-25(R)-furosta-5-en-20,22-dine-3-O-alpha-L-rhamnopyranosyl-(1-->2)-[alpha-L-rhamnopyranosyl-(1--> 4)]-beta-D-glucopyranoside.
CONCLUSIONS:
These compounds showed mild cytotoxicity against the cancer cell lines, A375, L929, and HeLa, in a dose-dependent manner.

Pseudoprotodioscin Dilution Calculator

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Preparing Stock Solutions of Pseudoprotodioscin

1 mg 5 mg 10 mg 20 mg 25 mg
1 mM 1.3751 mL 6.8757 mL 13.7514 mL 27.5028 mL 34.3784 mL
5 mM 0.275 mL 1.3751 mL 2.7503 mL 5.5006 mL 6.8757 mL
10 mM 0.1375 mL 0.6876 mL 1.3751 mL 2.7503 mL 3.4378 mL
50 mM 0.0275 mL 0.1375 mL 0.275 mL 0.5501 mL 0.6876 mL
100 mM 0.0138 mL 0.0688 mL 0.1375 mL 0.275 mL 0.3438 mL
* Note: If you are in the process of experiment, it's necessary to make the dilution ratios of the samples. The dilution data above is only for reference. Normally, it's can get a better solubility within lower of Concentrations.

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References on Pseudoprotodioscin

Two new steroidal saponins from the rhizomes of Dioscorea panthaica and their cytotoxic activity.[Pubmed:11745024]

Planta Med. 2001 Dec;67(9):853-7.

Two new steroidal saponins, dioscoresides C (1) and D (2), along with a new natural product, pregnadienolone 3-O-beta-gracillimatriose (3), and two known compounds, pregnadienolone 3-O-beta-chacotrioside (4) and Pseudoprotodioscin (5), were isolated from the rhizomes of Dioscorea panthaica Prain et Burkill. On the basis of extensive NMR studies and chemical evidence, dioscoresides C and D were determined to be 26-O-beta-D-glucopyranosyl-3 beta,26-dihydroxy-23(S)-methoxy-25(R)-furosta-5,20(22)-dien-3-O-alpha-L-rhamnopyr anosyl-(1-->2)-[alpha-L-rhamnopyranosyl-(1-->4)]-beta-D-glucopyranoside and 26-O-beta-D-glucopyranosyl-3 beta,26-dihydroxy-20,22-seco-25(R)-furosta-5-en-20,22-dine-3-O-alpha-L-rhamnopyra nosyl-(1-->2)-[alpha-L-rhamnopyranosyl-(1--> 4)]-beta-D-glucopyranoside. These compounds showed mild cytotoxicity against the cancer cell lines, A375, L929, and HeLa, in a dose-dependent manner.

Anti-inflammatory and anti-melanogenic steroidal saponin glycosides from Fenugreek (Trigonella foenum-graecum L.) seeds.[Pubmed:20979021]

Planta Med. 2011 May;77(7):705-10.

Fenugreek seed ( Trigonella foenum-graecum L.) is used as an herbal medicine for treating metabolic and nutritive dysfunctions. To determine if this plant has other beneficial effects, we tested the inhibitory activities of a methanol (MeOH) extract of fenugreek seed on the production of inflammatory cytokines and melanin synthesis in cultured cell lines in vitro. The MeOH extract inhibited the production of phorbol-12-myristate-13-acetate-induced inflammatory cytokines such as tumor necrosis factor (TNF)-alpha in cultured THP-1 cells, and also restrained the intracellular synthesis of melanin in murine melanoma B16F1 cells. We isolated three active constituents from fenugreek seed extracts. These were identified as the steroidal saponins 26- O-beta-D-glucopyranosyl-(25 R)-furost-5(6)-en-3 beta,22 beta,26-triol-3- O-alpha-L-rhamno-pyranosyl-(1'' --> 2')-O-[beta-D-glucopyranosyl-(1''' --> 6')- O]-beta-D-glucopyranoside 1, minutoside B 2, and Pseudoprotodioscin 3. Compounds 1 and 2 strongly suppressed the production of inflammatory cytokines, whereas 3 showed a weaker suppressing effect. Melanogenesis in B16F1 cells was significantly suppressed by 1 and 3, and weakly suppressed by 2. All three compounds showed moderate cytotoxicities. These results indicate that fenugreek extract and its active constituents could protect against skin damage.

Description

Pseudoprotodioscin, a furostanoside, inhibits SREBP1/2 and microRNA 33a/b levels and reduces the gene expression regarding the synthesis of cholesterol and triglycerides.

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