Lanatoside D

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

MedKoo CAT#: 559155

CAS#: 11030-31-2

Description: Lanatoside D is a cardiac glycoside.

Chemical Structure

Lanatoside D
CAS# 11030-31-2

Theoretical Analysis

MedKoo Cat#: 559155
Name: Lanatoside D
CAS#: 11030-31-2
Chemical Formula: C49H76O21
Exact Mass: 1000.4879
Molecular Weight: 1001.12
Elemental Analysis: C, 58.79; H, 7.65; O, 33.56

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 or click below button.
Note: Price will be listed if it is available in the future.

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Synonym: Lanatoside D;

IUPAC/Chemical Name: (2R,3R,4S,6S)-6-(((2R,3S,4S,6S)-4-hydroxy-6-(((2R,3S,4S,6R)-4-hydroxy-2-methyl-6-(((3S,5R,8R,9S,10S,12R,13S,14S,16S,17R)-12,14,16-trihydroxy-10,13-dimethyl-17-(5-oxo-2,5-dihydrofuran-3-yl)hexadecahydro-1H-cyclopenta[a]phenanthren-3-yl)oxy)tetrahydro-2H-pyran-3-yl)oxy)-2-methyltetrahydro-2H-pyran-3-yl)oxy)-2-methyl-3-(((2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)tetrahydro-2H-pyran-2-yl)oxy)tetrahydro-2H-pyran-4-yl acetate


InChi Code: InChI=1S/C49H76O21/c1-20-43(68-37-15-30(53)44(21(2)63-37)69-38-16-32(65-23(4)51)45(22(3)64-38)70-46-42(59)41(58)40(57)33(18-50)67-46)29(52)14-36(62-20)66-26-9-10-47(5)25(12-26)7-8-27-28(47)13-34(55)48(6)39(24-11-35(56)61-19-24)31(54)17-49(27,48)60/h11,20-22,25-34,36-46,50,52-55,57-60H,7-10,12-19H2,1-6H3/t20-,21-,22-,25-,26+,27-,28+,29+,30+,31+,32+,33-,34-,36+,37+,38+,39+,40-,41+,42-,43-,44-,45-,46+,47+,48-,49+/m1/s1

SMILES Code: C[C@H]1O[C@@H](O[C@H]2CC[C@]3([C@@H](C2)CC[C@@H]4[C@@H]3C[C@H]([C@@]5([C@@H](C6=CC(OC6)=O)[C@H](C[C@]45O)O)C)O)C)C[C@@H]([C@@H]1O[C@H]7C[C@@H]([C@@H]([C@H](O7)C)O[C@H]8C[C@@H]([C@@H]([C@H](O8)C)O[C@@H]9O[C@@H]([C@H]([C@@H]([C@H]9O)O)O)CO)OC(C)=O)O)O

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

Preparing Stock Solutions

The following data is based on the product molecular weight 1001.12 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

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1: MASCHERPA A. [Presence of lanatoside D in Digitalis lutea L]. Boll Soc Ital Biol Sper. 1960 Oct 31;36:1076-80. Italian. PubMed PMID: 13767722.

2: Saito H, Kawaguchi W, Iwata M, Maekawa K, Tanimoto T, Okada S. [Lanatoside C Reference Standard (Control 981) of National Institute of Health Sciences]. Kokuritsu Iyakuhin Shokuhin Eisei Kenkyusho Hokoku. 1999;(117):192-4. Japanese. PubMed PMID: 10939857.

3: KOVARIKOVA A, PITRA J, CEKAN A. [Information on lanatoside D]. Experientia. 1959 Mar 15;15(3):112. German. PubMed PMID: 13652950.

4: KOVARIKOVA A. [Determination of cardiotonic and cardiotoxic effects of lanatoside D]. Cesk Fysiol. 1958 Sep;7(5):493-4. Czech. PubMed PMID: 13629617.

5: KOVARIKOVA AL, STORK A. [Pharmacology and clinical use of lanatoside D]. Cas Lek Cesk. 1961 May 26;100:653-7. Czech. PubMed PMID: 13753676.

6: Sahin G, Verma SK, Gurel E. Calcium and magnesium elimination enhances accumulation of cardenolides in callus cultures of endemic Digitalis species of Turkey. Plant Physiol Biochem. 2013 Dec;73:139-43. doi: 10.1016/j.plaphy.2013.09.007. Epub 2013 Sep 24. PubMed PMID: 24095920.

7: KOVARIKOVA A. [Comparison of lanatoside A, B, C, D on the heart-lung preparation in cats]. Cesk Fysiol. 1960 May;9:293-4. Czech. PubMed PMID: 14411448.

8: Kandzia R, Grimm R, Eckerskorn C, Lindemann P, Luckner M. Purification and characterization of lanatoside 15'-O-acetylesterase from Digitalis lanata Ehrh. Planta. 1998 Mar;204(3):383-9. PubMed PMID: 9530881.

9: Chao MW, Chen TH, Huang HL, Chang YW, HuangFu WC, Lee YC, Teng CM, Pan SL. Lanatoside C, a cardiac glycoside, acts through protein kinase Cδ to cause apoptosis of human hepatocellular carcinoma cells. Sci Rep. 2017 Apr 7;7:46134. doi: 10.1038/srep46134. PubMed PMID: 28387249; PubMed Central PMCID: PMC5384006.

10: Gutierrez Mañero FJ, Ramos B, Lucas García JA, Probanza A, Barrientos Casero ML. Systemic induction of the biosynthesis of terpenic compounds in Digitalis lanata. J Plant Physiol. 2003 Feb;160(2):105-13. PubMed PMID: 12685026.

11: Linley PA, Mekkawi AG. Bio-Transformation of (G-3H)-digitoxin and (G-3H)-digoxin by Digitalis purpurea. Planta Med. 1982 Oct;46(2):113-8. PubMed PMID: 17396954.

12: Sechser T, Stika L, Modr Z, Elis J, Malý J. [Utilization of cardiac glycosides in Czechoslovakia--does it correspond to need?]. Cas Lek Cesk. 1989 May 12;128(20):609-16. Czech. PubMed PMID: 2752396.

13: Lichius JJ, Khyari DE, Wichtl M. Subalpinoside (S1), an Unknown Oleandrigenin Glycoside and Other Cardenol from Digitalis subalpina var. subalpina. Planta Med. 1991 Apr;57(2):159-61. PubMed PMID: 17226141.

14: Pellati F, Bruni R, Bellardi MG, Bertaccini A, Benvenuti S. Optimization and validation of a high-performance liquid chromatography method for the analysis of cardiac glycosides in Digitalis lanata. J Chromatogr A. 2009 Apr 10;1216(15):3260-9. doi: 10.1016/j.chroma.2009.02.042. Epub 2009 Feb 21. PubMed PMID: 19268961.

15: Ferrari R, Bongrani S. [Creatine phosphokinase release from perfused cardiac muscle under hypoxic conditions. Effect of propranolol, verapamil, reserpine and deslanoside]. G Ital Cardiol. 1979;9(4):411-6. Italian. PubMed PMID: 456802.

16: Ferguson DW, Abboud FM, Mark AL. Selective impairment of baroreflex-mediated vasoconstrictor responses in patients with ventricular dysfunction. Circulation. 1984 Mar;69(3):451-60. PubMed PMID: 6692507.

17: Gupta RS, Chopra A. Human cell mutants affected in the interaction of the 12 beta-OH group of cardiac glycosides with the digitalis receptor. Biochem Pharmacol. 1987 Nov 15;36(22):3829-33. PubMed PMID: 2825704.

18: Gurel E, Karvar S, Yucesan B, Eker I, Sameeullah M. An Overview of Cardenolides in Digitalis - More Than a Cardiotonic Compound. Curr Pharm Des. 2017;23(34):5104-5114. doi: 10.2174/1381612823666170825125426. PubMed PMID: 28847302.