Purpurea glycoside A

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

MedKoo CAT#: 598269

CAS#: 19855-40-4

Description: Purpurea glycoside A is a cardiac glycoside analog.

Chemical Structure

Purpurea glycoside A

CAS# 19855-40-4

Instruction

Theoretical Analysis

MedKoo Cat#: 598269
Name: Purpurea glycoside A
CAS#: 19855-40-4
Chemical Formula: C47H74O18
Exact Mass: 926.49
Molecular Weight: 927.090
Elemental Analysis: C, 60.89; H, 8.05; O, 31.06

Price and Availability

Size	Price	Availability	Quantity
25mg	USD -1	2 Weeks
Bulk inquiry Welcome, Customer: Please do not inquire quote if your intended use is for a patient since our products are for research use and for chemical synthesis use, not for human use . For in-stock products, we listed price in the web page. You may inquire prices for which sizes were not listed. If no price is listed, this means the product is not in stock at the moment, which may be available via custom synthesis. For cost-effective reason, minimum order of 1g is requested (typically very expensive). The lead time is usually 2-4 months. Quote of less than 1g will not be provided. MedKoo may not offer quote for below reasons: (1) current available synthetic method appears to be extremely expensive which is obviously not affordable to most customers; (2) Key raw material to make the product is temporally not available; (3) DEA controlled substances; (4) the product is under patent protection in customer’s country.

Synonym: Purpurea glycoside A; Glucodigitoxin; Purpureaglykosid A; Desacetyl-lanatosid A;

IUPAC/Chemical Name: 4-((3S,5R,8R,9R,10R,13R,14R,17S)-3-(((2S,4S,5R,6R)-5-(((2R,4S,5S,6R)-4,5-dihydroxy-6-methyltetrahydro-2H-pyran-2-yl)oxy)-4-(((2R,4S,5R,6R)-5-hydroxy-6-methyl-4-(((2R,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)tetrahydro-2H-pyran-2-yl)oxy)tetrahydro-2H-pyran-2-yl)oxy)-6-methyltetrahydro-2H-pyran-2-yl)oxy)-14-hydroxy-10,13-dimethylhexadecahydro-1H-cyclopenta[a]phenanthren-17-yl)furan-2(5H)-one

InChi Key: WJOCFXCSQDOQQR-ULZITLKASA-N

InChi Code: InChI=1S/C47H74O18/c1-21-38(51)30(49)16-35(58-21)65-43-23(3)60-36(18-32(43)62-37-17-31(39(52)22(2)59-37)63-44-42(55)41(54)40(53)33(19-48)64-44)61-26-8-11-45(4)25(15-26)6-7-29-28(45)9-12-46(5)27(10-13-47(29,46)56)24-14-34(50)57-20-24/h14,21-23,25-33,35-44,48-49,51-56H,6-13,15-20H2,1-5H3/t21-,22-,23-,25-,26+,27+,28-,29-,30+,31+,32+,33-,35-,36-,37-,38-,39-,40-,41+,42-,43-,44-,45-,46-,47-/m1/s1

SMILES Code: O=C1OCC([C@@H]2CC[C@@]3(O)[C@@H]4CC[C@@H]5C[C@@H](O[C@@H]6C[C@@H]([C@@H]([C@@H](C)O6)O[C@@H]7C[C@@H]([C@@H]([C@@H](C)O7)O)O)O[C@@H]8C[C@@H]([C@@H]([C@@H](C)O8)O)O[C@H]9[C@@H]([C@H]([C@@H]([C@@H](CO)O9)O)O)O)CC[C@@]5(C)[C@@H]4CC[C@]23C)=C1

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:

Instruction:

View handling instruction

Biological target:
In vitro activity:
In vivo activity:

Preparing Stock Solutions

The following data is based on the product molecular weight 927.09 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.

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: Beale TM, Taylor MS. Synthesis of cardiac glycoside analogs by catalyst-controlled, regioselective glycosylation of digitoxin. Org Lett. 2013 Mar 15;15(6):1358-61. doi: 10.1021/ol4003042. Epub 2013 Mar 6. PubMed PMID: 23465047.

2: Wu B, Li Y, Yan H, Ma Y, Luo H, Yuan L, Chen S, Lu S. Comprehensive transcriptome analysis reveals novel genes involved in cardiac glycoside biosynthesis and mlncRNAs associated with secondary metabolism and stress response in Digitalis purpurea. BMC Genomics. 2012 Jan 10;13:15. doi: 10.1186/1471-2164-13-15. PubMed PMID: 22233149; PubMed Central PMCID: PMC3269984.

3: Cieniak C, McDonald C, Nash J, Muhammad A, Badawi A, Haddad PS, Cuerrier A, Bennett SA, Foster BC, Arnason JT. Evaluation by microarray of the potential safety of Sarracenia purpurea L. (Sarraceniaceae) a traditional medicine used by the Cree of Eeyou Istchee. J Pharm Pharm Sci. 2015;18(4):562-77. PubMed PMID: 26626249.

4: Kwon HJ, Sim HJ, Lee SI, Lee YM, Park YD, Hong SP. HPLC method validation for Digitalis and its analogue by pulsed amperometric detection. J Pharm Biomed Anal. 2011 Jan 5;54(1):217-21. doi: 10.1016/j.jpba.2010.07.037. Epub 2010 Aug 6. PubMed PMID: 20800985.

5: Kuroda M, Kubo S, Matsuo Y, Atou T, Satoh J, Fujino T, Hayakawa M, Mimaki Y. New cardenolide glycosides from the seeds of Digitalis purpurea and their cytotoxic activity. Biosci Biotechnol Biochem. 2013;77(6):1186-92. Epub 2013 Jun 7. PubMed PMID: 23748755.

6: Li D, Li H, Ni X, Zhang H, Xia H. Construction of a gentamicin C1a-overproducing strain of Micromonospora purpurea by inactivation of the gacD gene. Microbiol Res. 2013 Jun 12;168(5):263-7. doi: 10.1016/j.micres.2012.12.006. Epub 2013 Jan 8. PubMed PMID: 23305768.

7: BROSSA-TORRES. [Therapeutic results with a new Digitalis purpurea glycoside]. Brux Med. 1962 Dec 16;42:1503-13. French. PubMed PMID: 14015846.

8: Fujino T, Kuroda M, Matsuo Y, Kubo S, Tamura C, Sakamoto N, Mimaki Y, Hayakawa M. Cardenolide glycosides from the seeds of Digitalis purpurea exhibit carcinoma-specific cytotoxicity toward renal adenocarcinoma and hepatocellular carcinoma cells. Biosci Biotechnol Biochem. 2015;79(2):177-84. doi: 10.1080/09168451.2014.975183. Epub 2014 Oct 27. PubMed PMID: 25345317.

9: König L. [Clinical therapeutic experiences with a standardized combination of A and B glycoside fractions of Digitalis purpurea]. Wien Med Wochenschr. 1971 Mar 6;121(10):180-3. German. PubMed PMID: 4104643.

10: Patil JG, Ahire ML, Nitnaware KM, Panda S, Bhatt VP, Kishor PB, Nikam TD. In vitro propagation and production of cardiotonic glycosides in shoot cultures of Digitalis purpurea L. by elicitation and precursor feeding. Appl Microbiol Biotechnol. 2013 Mar;97(6):2379-93. doi: 10.1007/s00253-012-4489-y. Epub 2012 Oct 19. PubMed PMID: 23081776.

11: OKANO A. Studies on the constituents of Digitalis purpurea L. VI. Glucodigifucoside, a new cardiotonic glycoside. Pharm Bull. 1957 Jun;5(3):272-6. PubMed PMID: 13465290.

12: Heuchel G, Coch H. [16-acetylgitoxin--a semisynthetic glycoside of digitalis purpurea]. Z Gesamte Inn Med. 1971 Feb 1;26(3):89-93. German. PubMed PMID: 5560772.

13: Wu B, Suo F, Lei W, Gu L. Comprehensive analysis of alternative splicing in Digitalis purpurea by strand-specific RNA-Seq. PLoS One. 2014 Aug 28;9(8):e106001. doi: 10.1371/journal.pone.0106001. eCollection 2014. PubMed PMID: 25167195; PubMed Central PMCID: PMC4148352.

14: MIYATAKE K, OKANO A, HOJI K, MIKI T. Studies on the constituents of Digitalis purpurea L. III. Gitostin, a new cardiotonic glycoside from digitalis seeds. Pharm Bull. 1957 Apr;5(2):163-7. PubMed PMID: 13452789.

15: Hubert J, Chollet S, Purson S, Reynaud R, Harakat D, Martinez A, Nuzillard JM, Renault JH. Exploiting the Complementarity between Dereplication and Computer-Assisted Structure Elucidation for the Chemical Profiling of Natural Cosmetic Ingredients: Tephrosia purpurea as a Case Study. J Nat Prod. 2015 Jul 24;78(7):1609-17. doi: 10.1021/acs.jnatprod.5b00174. Epub 2015 Jun 23. PubMed PMID: 26103208.

16: Pandey MM, Khatoon S, Rastogi S, Rawat AK. Determination of flavonoids, polyphenols and antioxidant activity of Tephrosia purpurea: a seasonal study. J Integr Med. 2016 Nov;14(6):447-455. doi: 10.1016/S2095-4964(16)60276-5. PubMed PMID: 27854196.

17: Hartl O. [Clinical experiences with a pure glycoside combination of Digitalis purpurea]. Wien Med Wochenschr. 1971 Apr 24;121(17):353-5. German. PubMed PMID: 5575101.

18: TATTJE DH. [Effects of fermentation on the glycoside content of leaves of Digitalis purpurea. II]. Pharm Weekbl. 1958 Sep 6;93(18):819-28. Dutch. PubMed PMID: 13590902.

19: Ikeda Y, Fujii Y, Nakaya I, Yamazaki M. Quantitative HPLC analysis of cardiac glycosides in Digitalis purpurea leaves. J Nat Prod. 1995 Jun;58(6):897-901. PubMed PMID: 7673934.

20: JENSEN KB. Paper chromatographic detection of new components in the glycoside complex of Digitalis purpurea. Acta Pharmacol Toxicol (Copenh). 1956;12(1):11-9. PubMed PMID: 13326460.

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