Gypsogenin

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

MedKoo CAT#: 592478

CAS#: 639-14-5

Description: Gypsogenin is a naturally occuring biochemical which exhibits anti-ABL1 kinase and anti-chronic Myelogenous Leukemia activities.

Chemical Structure

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Gypsogenin
CAS# 639-14-5
Instruction

Theoretical Analysis

MedKoo Cat#: 592478
Name: Gypsogenin
CAS#: 639-14-5
Chemical Formula: C30H46O4
Exact Mass: 470.34
Molecular Weight: 470.690
Elemental Analysis: C, 76.55; H, 9.85; O, 13.60

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.

Request quote for custom synthesis

Synonym: Albsapogenin; Astrantiagenin D; Githagenin; Gypsogenin; Gypsophilasapogenin;

IUPAC/Chemical Name: (3beta,4alpha)-3-Hydroxy-23-oxoolean-12-en-28-oic acid

InChi Key: QMHCWDVPABYZMC-MYPRUECHSA-N

InChi Code: InChI=1S/C30H46O4/c1-25(2)13-15-30(24(33)34)16-14-28(5)19(20(30)17-25)7-8-22-26(3)11-10-23(32)27(4,18-31)21(26)9-12-29(22,28)6/h7,18,20-23,32H,8-17H2,1-6H3,(H,33,34)/t20-,21+,22+,23-,26-,27-,28+,29+,30-/m0/s1

SMILES Code: C[C@@]1(C=O)[C@@H](O)CC[C@]2(C)[C@@]3([H])CC=C4[C@]5([H])CC(C)(C)CC[C@@](C(O)=O)5CC[C@](C)4[C@@](C)3CC[C@@]12[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

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 470.69 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: Zhang H, Mu Y, Wang F, Song L, Sun J, Liu Y, Sun J. Synthesis of gypsogenin derivatives with capabilities to arrest cell cycle and induce apoptosis in human cancer cells. R Soc Open Sci. 2018 Jan 24;5(1):171510. doi: 10.1098/rsos.171510. eCollection 2018 Jan. PubMed PMID: 29410854; PubMed Central PMCID: PMC5792931.

2: Ciftci HI, Ozturk SE, Ali TFS, Radwan MO, Tateishi H, Koga R, Ocak Z, Can M, Otsuka M, Fujita M. The First Pentacyclic Triterpenoid Gypsogenin Derivative Exhibiting Anti-ABL1 Kinase and Anti-chronic Myelogenous Leukemia Activities. Biol Pharm Bull. 2018 Apr 1;41(4):570-574. doi: 10.1248/bpb.b17-00902. Epub 2018 Jan 30. PubMed PMID: 29386476.

3: Qu YF, Gao JY, Wang J, Geng YM, Zhou Y, Sun CX, Li F, Feng L, Yu MJ, Wang GS. New Triterpenoid Saponins from the Herb Hylomecon japonica. Molecules. 2017 Oct 23;22(10). pii: E1731. doi: 10.3390/molecules22101731. PubMed PMID: 29065554.

4: Smułek W, Zdarta A, Pacholak A, Zgoła-Grześkowiak A, Marczak Ł, Jarzębski M, Kaczorek E. Saponaria officinalis L. extract: Surface active properties and impact on environmental bacterial strains. Colloids Surf B Biointerfaces. 2017 Feb 1;150:209-215. doi: 10.1016/j.colsurfb.2016.11.035. Epub 2016 Nov 27. PubMed PMID: 27918965.

5: Mikołajczyk-Bator K, Błaszczyk A, Czyżniejewski M, Kachlicki P. Identification of saponins from sugar beet (Beta vulgaris) by low and high-resolution HPLC-MS/MS. J Chromatogr B Analyt Technol Biomed Life Sci. 2016 Sep 1;1029-1030:36-47. doi: 10.1016/j.jchromb.2016.06.038. Epub 2016 Jun 27. PubMed PMID: 27423042.

6: Greatrex BW, Daines AM, Hook S, Lenz DH, McBurney W, Rades T, Rendle PM. Synthesis, Formulation, and Adjuvanticity of Monodesmosidic Saponins with Olenanolic Acid, Hederagenin and Gypsogenin Aglycones, and some C-28 Ester Derivatives. ChemistryOpen. 2015 Sep 30;4(6):740-55. doi: 10.1002/open.201500149. eCollection 2015 Dec. PubMed PMID: 27308200; PubMed Central PMCID: PMC4906508.

7: Jung K, Lee D, Yu JS, Namgung H, Kang KS, Kim KH. Protective effect and mechanism of action of saponins isolated from the seeds of gac (Momordica cochinchinensis Spreng.) against cisplatin-induced damage in LLC-PK1 kidney cells. Bioorg Med Chem Lett. 2016 Mar 1;26(5):1466-70. doi: 10.1016/j.bmcl.2016.01.056. Epub 2016 Jan 21. PubMed PMID: 26838808.

8: Xie LX, Zhang HC, Wang HY, Wang Y, Wang FL, Sun JY. Two new triterpenoids from Gypsophila oldhamiana. Nat Prod Res. 2016;30(9):1068-74. doi: 10.1080/14786419.2015.1107060. Epub 2015 Nov 5. PubMed PMID: 26539898.

9: Mikołajczyk-Bator K, Błaszczyk A, Czyżniejewski M, Kachlicki P. Characterisation and identification of triterpene saponins in the roots of red beets (Beta vulgaris L.) using two HPLC-MS systems. Food Chem. 2016 Feb 1;192:979-90. doi: 10.1016/j.foodchem.2015.07.111. Epub 2015 Jul 23. PubMed PMID: 26304438.

10: Li H, Wang XY, Wang XY, Hua D, Liu Y, Tang HF. Two new triterpenoid saponins from the aerial parts of Anemone taipaiensis. J Asian Nat Prod Res. 2015 May;17(5):576-85. doi: 10.1080/10286020.2015.1043903. Epub 2015 May 29. PubMed PMID: 26021881.

11: Lu Y, Van D, Deibert L, Bishop G, Balsevich J. Antiproliferative quillaic acid and gypsogenin saponins from Saponaria officinalis L. roots. Phytochemistry. 2015 May;113:108-20. doi: 10.1016/j.phytochem.2014.11.021. Epub 2014 Dec 19. PubMed PMID: 25534953.

12: Heller L, Schwarz S, Weber BA, Csuk R. Gypsogenin derivatives: an unexpected class of inhibitors of cholinesterases. Arch Pharm (Weinheim). 2014 Oct;347(10):707-16. doi: 10.1002/ardp.201400103. Epub 2014 Jul 8. PubMed PMID: 25042600.

13: Emirdağ-Öztürk S, Karayıldırım T, Çapcı-Karagöz A, Alankuş-Çalışkan Ö, Özmen A, Poyrazoğlu-Çoban E. Synthesis, antimicrobial and cytotoxic activities, and structure-activity relationships of gypsogenin derivatives against human cancer cells. Eur J Med Chem. 2014 Jul 23;82:565-73. doi: 10.1016/j.ejmech.2014.05.084. Epub 2014 Jun 7. PubMed PMID: 24941130.

14: Gevrenova R, Joubert O, Mandova T, Zaiou M, Chapleur Y, Henry M. Cytotoxic effects of four Caryophyllaceae species extracts on macrophage cell lines. Pharm Biol. 2014 Jul;52(7):919-25. doi: 10.3109/13880209.2013.868492. Epub 2014 May 27. PubMed PMID: 24863282.

15: Arslan I. Simenoside A, a new triterpenoid saponin from Gypsophila simonii Hub.-Mor. Chem Biodivers. 2014 Mar;11(3):445-50. doi: 10.1002/cbdv.201300118. PubMed PMID: 24634074.

16: Ma L, Yu AH, Sun LL, Gao W, Zhang MM, Su YL, Liu H, Ji T. Two new bidesmoside triterpenoid saponins from the seeds of Momordica charantia L. Molecules. 2014 Feb 21;19(2):2238-46. doi: 10.3390/molecules19022238. PubMed PMID: 24566301.

17: Emirdağ-Öztürk S, Babahan İ, Özmen A. Synthesis, characterization and in vitro anti-neoplastic activity of gypsogenin derivatives. Bioorg Chem. 2014 Apr;53:15-23. doi: 10.1016/j.bioorg.2013.12.001. Epub 2013 Dec 25. PubMed PMID: 24463219.

18: Zhao Y, Wang X, Wang H, Liu T, Xin Z. Two new noroleanane-type triterpene saponins from the methanol extract of Salicornia herbacea. Food Chem. 2014 May 15;151:101-9. doi: 10.1016/j.foodchem.2013.11.030. Epub 2013 Nov 16. PubMed PMID: 24423508.

19: Böttger S, Westhof E, Siems K, Melzig MF. Structure-activity relationships of saponins enhancing the cytotoxicity of ribosome-inactivating proteins type I (RIP-I). Toxicon. 2013 Oct;73:144-50. doi: 10.1016/j.toxicon.2013.07.011. Epub 2013 Jul 25. PubMed PMID: 23891686.

20: Voutquenne-Nazabadioko L, Gevrenova R, Borie N, Harakat D, Sayagh C, Weng A, Thakur M, Zaharieva M, Henry M. Triterpenoid saponins from the roots of Gypsophila trichotoma Wender. Phytochemistry. 2013 Jun;90:114-27. doi: 10.1016/j.phytochem.2013.03.001. Epub 2013 Apr 3. PubMed PMID: 23561300.