Prosapogenin A

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

MedKoo CAT#: 598866

CAS#: 19057-67-1

Description: Prosapogenin A inhibits cell growth of MCF7 via downregulating STAT3 and glycometabolism-related gene.

Chemical Structure

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Prosapogenin A
CAS# 19057-67-1
Instruction

Theoretical Analysis

MedKoo Cat#: 598866
Name: Prosapogenin A
CAS#: 19057-67-1
Chemical Formula: C39H62O12
Exact Mass: 722.42
Molecular Weight: 722.910
Elemental Analysis: C, 64.80; H, 8.65; O, 26.56

Price and Availability

This product is not in stock, which may be available by custom synthesis. For cost-effective reason, minimum order is 1g (price is usually high, lead time is 2~3 months, depending on the technical challenge). Quote less than 1g will not be provided. To request quote, please email to sales @medkoo.com or click below button.
Note: Price will be listed if it is available in the future.

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Synonym: Prosapogenin A; Saponin Ta; Lilioglycoside D; Paris saponin V;

IUPAC/Chemical Name: (2S,3R,4R,5R,6S)-2-(((2R,3R,4S,5S,6R)-4,5-dihydroxy-6-(hydroxymethyl)-2-(((4S,5'R,6aR,6bS,8aS,8bR,9S,10R,11aS,12aS,12bS)-5',6a,8a,9-tetramethyl-1,3,3',4,4',5,5',6,6a,6b,6',7,8,8a,8b,9,11a,12,12a,12b-icosahydrospiro[naphtho[2',1':4,5]indeno[2,1-b]furan-10,2'-pyran]-4-yl)oxy)tetrahydro-2H-pyran-3-yl)oxy)-6-methyltetrahydro-2H-pyran-3,4,5-triol

InChi Key: HDXIQHTUNGFJIC-FOAHKCLGSA-N

InChi Code: InChI=1S/C39H62O12/c1-18-8-13-39(46-17-18)19(2)28-26(51-39)15-25-23-7-6-21-14-22(9-11-37(21,4)24(23)10-12-38(25,28)5)48-36-34(32(44)30(42)27(16-40)49-36)50-35-33(45)31(43)29(41)20(3)47-35/h6,18-20,22-36,40-45H,7-17H2,1-5H3/t18-,19+,20+,22+,23-,24+,25+,26+,27-,28+,29+,30-,31-,32+,33-,34-,35+,36-,37+,38+,39-/m1/s1

SMILES Code: O[C@@H]([C@@H]([C@@H](CO)O1)O)[C@@H](O[C@H]2[C@@H]([C@@H]([C@H]([C@H](C)O2)O)O)O)[C@@H]1O[C@H]3CC[C@]4(C)[C@@]5([H])CC[C@]6(C)[C@]7([H])[C@@]([H])(O[C@@]8(OC[C@H](C)CC8)[C@H]7C)C[C@@]6([H])[C@]5([H])CC=C4C3

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

Shelf Life: >3 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: 2934.99.03.00

More Info:

Biological target:
In vitro activity:
In vivo activity:

Preparing Stock Solutions

The following data is based on the product molecular weight 722.91 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:
In vitro protocol:
In vivo protocol:

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1: Wang TX, Zhang ZQ, Cong Y, Shi XY, Liu YH, Zhao FL. Prosapogenin A induces apoptosis in human cancer cells in vitro via inhibition of the STAT3 signaling pathway and glycolysis. Oncol Lett. 2013 Nov;6(5):1323-1328. Epub 2013 Sep 4. PubMed PMID: 24179517; PubMed Central PMCID: PMC3813670.

2: Wang TX, Shi XY, Cong Y, Zhang ZQ, Liu YH. [Prosapogenin A inhibits cell growth of MCF7 via downregulating STAT3 and glycometabolism-related gene]. Yao Xue Xue Bao. 2013 Sep;48(9):1510-4. Chinese. PubMed PMID: 24358789.

3: Han Y, Jung HW, Lee DH, Kwon SY, Son KH, Park YK. Anti-inflammatory effects of prosapogenin III from the dried roots of Liriope platyphylla in LPS-stimulated RAW264.7 cells. J Asian Nat Prod Res. 2013 Sep;15(9):1038-49. doi: 10.1080/10286020.2013.825253. Epub 2013 Aug 14. PubMed PMID: 23944983.

4: Chen YJ, Takeda T, Ogihara Y, Iitaka Y. Studies on the constituents of Xanthoceras sorbifolia Bunge. II. Major sapogenol and a prosapogenin from the fruits of Xanthoceras sorbifolia Bunge. Chem Pharm Bull (Tokyo). 1984 Sep;32(9):3378-83. PubMed PMID: 6549271.

5: Kaku T, Kawashima Y. Isolation and characterization of ginsenoside-Rg2, 20R-prosapogenin, 20S-prosapogenin and delta 20-prosapogenin. Chemical studies on saponins of Panax ginseng C. A. Meyer, Third report. Arzneimittelforschung. 1980;30(6):936-43. PubMed PMID: 7191267.

6: Hata T, Kita T, Kawabata A, Itoh E, Kawashima Y. Effect of ginseng-20S-prosapogenin on tissue blood flow measured by the hydrogen clearance method in sympathicotonic- or parasympathicotonic-type stressed mice. J Pharmacobiodyn. 1985 Dec;8(12):1068-72. PubMed PMID: 3834061.

7: WELLER P. [Clinical effect and mechanism of action of a new prosapogenin-compound from Aesculus hippocastanum]. Dtsch Gesundheitsw. 1959 Oct 29;14:2017-20. German. PubMed PMID: 13843854.

8: Lee SA, Jo HK, Im BO, Kim S, Whang WK, Ko SK. Changes in the Contents of Prosapogenin in the Red Ginseng (Panax ginseng) Depending on Steaming Batches. J Ginseng Res. 2012 Jan;36(1):102-6. doi: 10.5142/jgr.2012.36.1.102. PubMed PMID: 23717110; PubMed Central PMCID: PMC3659570.

9: VOIGTLANDER HW, ROSENBERG W. [Prosapogenin GB (beta-aescin). A contribution to the chemistry of horse chestnut saponins]. Arzneimittelforschung. 1963 May;13:385-6. German. PubMed PMID: 13997702.

10: Pelletier SW, Nakamura S. A prosapogenin from Polygala senega and Polygala tenuifolia. Tetrahedron Lett. 1967 Dec;52:5303-6. PubMed PMID: 6080933.

11: Kawasaki T, Yamauchi T. Structures of prosapogenin-B and -A of dioscin and cooccurrence of B with dioscin in the rhizoma of Dioscorea tokoro Makino. Chem Pharm Bull (Tokyo). 1968 Jun;16(6):1070-5. PubMed PMID: 5706814.

12: Chung JW, Noh EJ, Zhao HL, Sim JS, Ha YW, Shin EM, Lee EB, Cheong CS, Kim YS. Anti-inflammatory activity of prosapogenin methyl ester of platycodin D via nuclear factor-kappaB pathway inhibition. Biol Pharm Bull. 2008 Nov;31(11):2114-20. PubMed PMID: 18981583.

13: Wang SL, Cai B, Cui CB, Liu HW, Wu CF, Yao XS. [Apoptosis of human chronic myeloid leukemia k562 cell induced by prosapogenin B of dioscin (P.B) in vitro]. Ai Zheng. 2003 Aug;22(8):795-800. Chinese. PubMed PMID: 12917022.

14: Yokoyama H, Hiai S, Oura H. [Rat plasma corticosterone secretion-inducing activities of total saponin and prosapogenin methyl esters from the roots of Platycodon grandiflorum A.DC]. Yakugaku Zasshi. 1982 Dec;102(12):1191-4. Japanese. PubMed PMID: 7182453.

15: Han BH, Park MH, Han YN, Woo LK, Sankawa U, Yahara S, Tanaka O. Degradation of ginseng saponins under mild acidic conditions. Planta Med. 1982 Mar;44(3):146-9. PubMed PMID: 17402098.

16: Wang JJ, Liu YX, Wen D, Yu HS, Kang LP, Pang X, Zhao Yang, Ma BP, Chen YD. [Study on steroidal saponins from Dioscorea zingiberensis and their platelet aggregation activities]. Zhongguo Zhong Yao Za Zhi. 2014 Oct;39(19):3782-7. Chinese. PubMed PMID: 25612440.

17: Pang X, Wen D, Zhao Y, Xiong CQ, Wang XQ, Yu LY, Ma BP. Steroidal saponins obtained by biotransformation of total furostanol glycosides from Dioscorea zingiberensis with Absidia coerulea. Carbohydr Res. 2015 Jan 30;402:236-40. doi: 10.1016/j.carres.2014.11.011. Epub 2014 Nov 29. PubMed PMID: 25498025.

18: Yoon KD, Chin YW, Yang MH, Choi J, Kim J. Application of high-speed countercurrent chromatography-evaporative light scattering detection for the separation of seven steroidal saponins from Dioscorea villosa. Phytochem Anal. 2012 Sep-Oct;23(5):462-8. doi: 10.1002/pca.2342. Epub 2012 Mar 9. PubMed PMID: 22407490.

19: Ko SR, Suzuki Y, Choi KJ, Kim YH. Enzymatic preparation of genuine prosapogenin, 20(S)-ginsenoside Rh1, from ginsenosides Re and Rg1. Biosci Biotechnol Biochem. 2000 Dec;64(12):2739-43. PubMed PMID: 11210151.

20: Jaiaree N, Itharat A, Ruangnoo S. Cytotoxic and Anti-inflammatory Activities of Medicinal Plants and Women’s Health Remedy Found in “Mahachotarat Scripture” of Thai Traditional Medicine. J Med Assoc Thai. 2016 Jul;99 Suppl 4:S211-21. PubMed PMID: 29926715.