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MedKoo Cat#: 464009 | Name: Pseudoprotodioscin
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Description:

WARNING: This product is for research use only, not for human or veterinary use.

Pseudoprotodioscin is a furostanoside that inhibits SREBP1/2 and microRNA 33a/b levels and reduces the gene expression regarding the synthesis of cholesterol and triglycerides. Pseudoprotodioscin is a steroidal saponin that has been found in D. panthaica.

Chemical Structure

Pseudoprotodioscin
Pseudoprotodioscin
CAS#102115-79-7

Theoretical Analysis

MedKoo Cat#: 464009

Name: Pseudoprotodioscin

CAS#: 102115-79-7

Chemical Formula: C51H82O21

Exact Mass: 1030.5349

Molecular Weight: 1031.20

Elemental Analysis: C, 59.40; H, 8.02; O, 32.58

Price and Availability

Size Price Availability Quantity
10mg USD 250.00 2 Weeks
50mg USD 650.00 2 Weeks
100mg USD 950.00 2 Weeks
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Related CAS #
No Data
Synonym
Pseudoprotodioscin;
IUPAC/Chemical Name
(2S,2'S,3R,3'R,4R,4'R,5R,5'R,6S,6'S)-6,6'-(((2R,3S,4S,5R,6R)-4-hydroxy-2-(hydroxymethyl)-6-(((4S,6aR,6bS,8aS,8bS,11aS,12aS,12bS)-6a,8a,9-trimethyl-10-((R)-3-methyl-4-(((2R,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)tetrahydro-2H-pyran-2-yl)oxy)butyl)-3,4,5,6,6a,6b,7,8,8a,8b,11a,12,12a,12b-tetradecahydro-1H-naphtho[2',1':4,5]indeno[2,1-b]furan-4-yl)oxy)tetrahydro-2H-pyran-3,5-diyl)bis(oxy))bis(2-methyltetrahydro-2H-pyran-3,4,5-triol)
InChi Key
MDCUMTGKKLOMCW-XNVNDPJESA-N
InChi Code
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
SMILES Code
C[C@]12[C@]([H])([C@]3([C@]([H])(CC2)[C@]4(C)C(C[C@@H](O[C@H]5[C@H](O[C@H]6[C@H](O)[C@H](O)[C@@H](O)[C@H](C)O6)[C@@H](O)[C@H](O[C@H]7[C@H](O)[C@H](O)[C@@H](O)[C@H](C)O7)[C@@H](CO)O5)CC4)=CC3)[H])C[C@]8([C@@]1(C(C)=C(O8)CC[C@H](CO[C@H]9[C@@H]([C@H]([C@@H]([C@H](O9)CO)O)O)O)C)[H])[H]
Appearance
Solid powder
Purity
>98% (or refer to the Certificate of Analysis)
Shipping Condition
Shipped under ambient temperature as non-hazardous chemical. This product is stable enough for a few weeks during ordinary shipping and time spent in Customs.
Storage Condition
Dry, dark and at 0 - 4 C for short term (days to weeks) or -20 C for long term (months to years).
Solubility
Soluble in DMSO and DMF
Shelf Life
>2 years if stored properly
Drug Formulation
This drug may be formulated in DMSO
Stock Solution Storage
0 - 4 C for short term (days to weeks), or -20 C for long term (months).
HS Tariff Code
2934.99.9001
More Info
Product Data
Product Data
Instruction
View handling instruction
Biological target:
Pseudoprotodioscin exhibits cytotoxicity against A375, L929, and HeLa cancer cells. In 3T3-L1 preadipocytes, it enhances nuclear accumulation of ERα during differentiation. Pseudoprotodioscin suppresses NF-κB activity induced by LPS in mouse peritoneal macrophages and human umbilical vein endothelial cells (HUVECs).
In vitro activity:
In Hep G2 cells, pseudoprotodioscin increased ABCA1 protein and mRNA levels, promoting the efflux of cholesterol mediated by Apolipoprotein A-1 (ApoA-1). In THP-1 macrophages, pseudoprotodioscin reduced the mRNA levels of genes involved in cholesterol synthesis (HMGCR, FAS, and ACC) and promoted the expression of the low-density lipoprotein receptor by decreasing PCSK9 levels. These findings suggest that pseudoprotodioscin has the potential to modulate cholesterol metabolism. Reference: Fitoterapia. 2019 Nov;139:104393. https://pubmed.ncbi.nlm.nih.gov/31669721/
In vivo activity:
In ovariectomized apoE-/- mice fed a high-cholesterol diet, pseudoprotodioscin administration alleviated atherosclerotic lesions and reduced cholesterol levels. Pseudoprotodioscin increased ERα and eNOS levels while suppressing cell adhesion molecules and MCP-1 in HUVECs. Pseudoprotodioscin displayed ERα-dependent antiadipogenic effects in perivascular adipose tissue and induced the release of adiponectin. Reference: Eur J Pharmacol. 2020 Feb 15;869:172887. https://pubmed.ncbi.nlm.nih.gov/31877277/
Solvent mg/mL mM
Solubility
DMF 10.0 9.71
DMSO 10.0 9.71
Note: There can be variations in solubility for the same chemical from different vendors or different batches from the same vendor. The following factors can affect the solubility of the same chemical: solvent used for crystallization, residual solvent content, polymorphism, salt versus free form, degree of hydration, solvent temperature. Please use the solubility data as a reference only. Warming and sonication will facilitate dissolving. Still have questions? Please contact our Technical Support scientists.

Preparing Stock Solutions

The following data is based on the product molecular weight 1,031.20 Batch specific molecular weights may vary from batch to batch due to the degree of hydration, which will affect the solvent volumes required to prepare stock solutions.

Recalculate based on batch purity %
Concentration / Solvent Volume / Mass 1 mg 5 mg 10 mg
1 mM 1.15 mL 5.76 mL 11.51 mL
5 mM 0.23 mL 1.15 mL 2.3 mL
10 mM 0.12 mL 0.58 mL 1.15 mL
50 mM 0.02 mL 0.12 mL 0.23 mL
Formulation protocol:
1. Hwang JT, Park KS, Ryuk JA, Kim HJ, Ko BS. Development of an Oriental Medicine Discrimination Method through Analysis of Steroidal Saponins in Dioscorea nipponica Makino and Their Anti-Osteosarcoma Effects. Molecules. 2019 Nov 6;24(22):4022. doi: 10.3390/molecules24224022. PMID: 31698850; PMCID: PMC6891741. 2. Gai Y, Li Y, Xu Z, Chen J. Pseudoprotodioscin inhibits SREBPs and microRNA 33a/b levels and reduces the gene expression regarding the synthesis of cholesterol and triglycerides. Fitoterapia. 2019 Nov;139:104393. doi: 10.1016/j.fitote.2019.104393. Epub 2019 Oct 25. PMID: 31669721. 3. Li X, Liang J, Qin A, Wang T, Liu S, Li W, Yuan C, Qu L, Zou W. Protective effect of Di'ao Xinxuekang capsule against doxorubicin-induced chronic cardiotoxicity. J Ethnopharmacol. 2022 Apr 6;287:114943. doi: 10.1016/j.jep.2021.114943. Epub 2021 Dec 24. PMID: 34954266. 4. Sun B, Yang D, Yin YZ, Xiao J. Estrogenic and anti-inflammatory effects of pseudoprotodioscin in atherosclerosis-prone mice: Insights into endothelial cells and perivascular adipose tissues. Eur J Pharmacol. 2020 Feb 15;869:172887. doi: 10.1016/j.ejphar.2019.172887. Epub 2019 Dec 23. PMID: 31877277.
In vitro protocol:
1. Hwang JT, Park KS, Ryuk JA, Kim HJ, Ko BS. Development of an Oriental Medicine Discrimination Method through Analysis of Steroidal Saponins in Dioscorea nipponica Makino and Their Anti-Osteosarcoma Effects. Molecules. 2019 Nov 6;24(22):4022. doi: 10.3390/molecules24224022. PMID: 31698850; PMCID: PMC6891741. 2. Gai Y, Li Y, Xu Z, Chen J. Pseudoprotodioscin inhibits SREBPs and microRNA 33a/b levels and reduces the gene expression regarding the synthesis of cholesterol and triglycerides. Fitoterapia. 2019 Nov;139:104393. doi: 10.1016/j.fitote.2019.104393. Epub 2019 Oct 25. PMID: 31669721.
In vivo protocol:
1. Li X, Liang J, Qin A, Wang T, Liu S, Li W, Yuan C, Qu L, Zou W. Protective effect of Di'ao Xinxuekang capsule against doxorubicin-induced chronic cardiotoxicity. J Ethnopharmacol. 2022 Apr 6;287:114943. doi: 10.1016/j.jep.2021.114943. Epub 2021 Dec 24. PMID: 34954266. 2. Sun B, Yang D, Yin YZ, Xiao J. Estrogenic and anti-inflammatory effects of pseudoprotodioscin in atherosclerosis-prone mice: Insights into endothelial cells and perivascular adipose tissues. Eur J Pharmacol. 2020 Feb 15;869:172887. doi: 10.1016/j.ejphar.2019.172887. Epub 2019 Dec 23. PMID: 31877277.
1: Gui-Ya Y, Ya-Qing C, Zi-Jing X, Jun-Na S, Dan Z, Yu-Guang Z, Long G. [Quality control of Dioscoreae Nipponicae Rhizoma based on fingerprint and quantitative analysis]. Zhongguo Zhong Yao Za Zhi. 2020 Oct;45(20):4949-4956. Chinese. doi: 10.19540/j.cnki.cjcmm.20200615.201. PMID: 33350268. 2: Sun B, Yang D, Yin YZ, Xiao J. Estrogenic and anti-inflammatory effects of pseudoprotodioscin in atherosclerosis-prone mice: Insights into endothelial cells and perivascular adipose tissues. Eur J Pharmacol. 2020 Feb 15;869:172887. doi: 10.1016/j.ejphar.2019.172887. Epub 2019 Dec 23. PMID: 31877277. 3: Hwang JT, Park KS, Ryuk JA, Kim HJ, Ko BS. Development of an Oriental Medicine Discrimination Method through Analysis of Steroidal Saponins in Dioscorea nipponica Makino and Their Anti-Osteosarcoma Effects. Molecules. 2019 Nov 6;24(22):4022. doi: 10.3390/molecules24224022. PMID: 31698850; PMCID: PMC6891741. 4: Gai Y, Li Y, Xu Z, Chen J. Pseudoprotodioscin inhibits SREBPs and microRNA 33a/b levels and reduces the gene expression regarding the synthesis of cholesterol and triglycerides. Fitoterapia. 2019 Nov;139:104393. doi: 10.1016/j.fitote.2019.104393. Epub 2019 Oct 25. PMID: 31669721. 5: Sun B, Yin YZ, Xiao J. An In Vivo Estrogen Deficiency Mouse Model for Screening Exogenous Estrogen Treatments of Cardiovascular Dysfunction After Menopause. J Vis Exp. 2019 Aug 13;(150). doi: 10.3791/59536. PMID: 31475965. 6: Siddiqui MA, Ali Z, Chittiboyina AG, Khan IA. Hepatoprotective Effect of Steroidal Glycosides From Dioscorea villosa on Hydrogen Peroxide-Induced Hepatotoxicity in HepG2 Cells. Front Pharmacol. 2018 Jul 23;9:797. doi: 10.3389/fphar.2018.00797. PMID: 30083104; PMCID: PMC6065280. 7: Hu HX, Gao RR, Gao ZH, Qiao Y, Dong XR, Ding G, Sun DA. Microbial transformation of pseudoprotodioscin by Gibberella fujikuroi. J Asian Nat Prod Res. 2018 Jul;20(7):624-632. doi: 10.1080/10286020.2018.1468438. Epub 2018 May 7. PMID: 29732923. 8: Qing LS, Xue Y, Ding LS, Liu YM, Liang J, Liao X. A Rapid Study of Botanical Drug-Drug Interaction with Protein by Re-ligand Fishing using Human Serum Albumin-Functionalized Magnetic Nanoparticles. Nat Prod Commun. 2015 Dec;10(12):2161-3. PMID: 26882690. 9: Liao M, Dai C, Liu M, Chen J, Chen Z, Xie Z, Yao M. Simultaneous determination of four furostanol glycosides in rat plasma by UPLC-MS/MS and its application to PK study after oral administration of Dioscorea nipponica extracts. J Pharm Biomed Anal. 2016 Jan 5;117:372-9. doi: 10.1016/j.jpba.2015.09.021. Epub 2015 Sep 21. PMID: 26433169. 10: Liao M, Chen X, Chen J, Liu M, Wang J, Chen Z, Xie Z, Yao M. Determination of pseudoprotodioscin in rat plasma by UPLC-MS/MS: Assay development and application to pharmacokinetic study. J Chromatogr B Analyt Technol Biomed Life Sci. 2016 Jul 15;1026:97-104. doi: 10.1016/j.jchromb.2015.05.004. Epub 2015 May 15. PMID: 26012509. 11: Tang YN, Pang YX, He XC, Zhang YZ, Zhang JY, Zhao ZZ, Yi T, Chen HB. UPLC- QTOF-MS identification of metabolites in rat biosamples after oral administration of Dioscorea saponins: a comparative study. J Ethnopharmacol. 2015 May 13;165:127-40. doi: 10.1016/j.jep.2015.02.017. Epub 2015 Feb 16. PMID: 25698242. 12: Cheng XL, Qi LW, Wang Q, Liu XG, Boubertakh B, Wan JY, Liu EH, Li P. Highly efficient sample preparation and quantification of constituents from traditional Chinese herbal medicines using matrix solid-phase dispersion extraction and UPLC-MS/MS. Analyst. 2013 Apr 21;138(8):2279-88. doi: 10.1039/c3an36732k. PMID: 23443607. 13: Kawabata T, Cui MY, Hasegawa T, Takano F, Ohta T. Anti-inflammatory and anti-melanogenic steroidal saponin glycosides from Fenugreek (Trigonella foenum- graecum L.) seeds. Planta Med. 2011 May;77(7):705-10. doi: 10.1055/s-0030-1250477. Epub 2010 Oct 26. PMID: 20979021. 14: Qinga LS, Xue Y, Zheng Y, Xiong J, Liao X, Ding LS, Li BG, Liu YM. Ligand fishing from Dioscorea nipponica extract using human serum albumin functionalized magnetic nanoparticles. J Chromatogr A. 2010 Jul 9;1217(28):4663-8. doi: 10.1016/j.chroma.2010.05.009. PMID: 20627255; PMCID: PMC2955990. 15: Ivanova A, Serly J, Dinchev D, Ocsovszki I, Kostova I, Molnar J. Screening of some saponins and phenolic components of Tribulus terrestris and Smilax excelsa as MDR modulators. In Vivo. 2009 Jul-Aug;23(4):545-50. PMID: 19567388. 16: Ivanova A, Mikhova B, Klaiber I, Dinchev D, Kostova I. Steroidal saponins from Smilax excelsa rhizomes. Nat Prod Res. 2009;23(10):916-24. doi: 10.1080/14786410802624827. PMID: 19521905. 17: Lin S, Wang D, Yang D, Yao J, Tong Y, Chen J. Characterization of steroidal saponins in crude extract from Dioscorea nipponica Makino by liquid chromatography tandem multi-stage mass spectrometry. Anal Chim Acta. 2007 Sep 5;599(1):98-106. doi: 10.1016/j.aca.2007.07.070. Epub 2007 Aug 3. PMID: 17765069. 18: Dinchev D, Janda B, Evstatieva L, Oleszek W, Aslani MR, Kostova I. Distribution of steroidal saponins in Tribulus terrestris from different geographical regions. Phytochemistry. 2008 Jan;69(1):176-86. doi: 10.1016/j.phytochem.2007.07.003. Epub 2007 Aug 23. PMID: 17719068. 19: Dong M, Feng X, Wang BX, Ikejima T, Wu LJ. Microbial metabolism of pseudoprotodioscin. Planta Med. 2004 Jul;70(7):637-41. doi: 10.1055/s-2004-827187. PMID: 15254856. 20: Dong M, Wu LJ, Chen Q, Wang BX. [Isolation and identification of steroidal saponins from Dioscorea panthaica Prain et Burkill]. Yao Xue Xue Bao. 2001 Jan;36(1):42-5. Chinese. PMID: 12579859.

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