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L2261

Sigma-Aldrich

Lanatoside C

≥97% (TLC)

Synonym(s):

Digilanide C, Digilanogen C, Isolanide, Lanatigen C

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About This Item

Empirical Formula (Hill Notation):
C49H76O20
CAS Number:
Molecular Weight:
985.12
EC Number:
MDL number:
UNSPSC Code:
12352201
PubChem Substance ID:
NACRES:
NA.25

Assay

≥97% (TLC)

form

powder

color

white

storage temp.

−20°C

SMILES string

C[C@H]1O[C@H](C[C@H](O)[C@@H]1O[C@H]2C[C@H](O)[C@H](O[C@H]3C[C@H](OC(C)=O)[C@H](O[C@@H]4O[C@H](CO)[C@@H](O)[C@H](O)[C@H]4O)[C@@H](C)O3)[C@@H](C)O2)O[C@H]5CC[C@@]6(C)[C@H](CC[C@@H]7[C@@H]6C[C@@H](O)[C@]8(C)[C@H](CC[C@]78O)C9=CC(=O)OC9)C5

InChI

1S/C49H76O20/c1-21-43(67-38-17-32(53)44(22(2)62-38)68-39-18-33(64-24(4)51)45(23(3)63-39)69-46-42(58)41(57)40(56)34(19-50)66-46)31(52)16-37(61-21)65-27-9-11-47(5)26(14-27)7-8-29-30(47)15-35(54)48(6)28(10-12-49(29,48)59)25-13-36(55)60-20-25/h13,21-23,26-35,37-46,50,52-54,56-59H,7-12,14-20H2,1-6H3/t21-,22-,23-,26-,27+,28-,29-,30+,31+,32+,33+,34-,35-,37+,38+,39+,40-,41+,42-,43-,44-,45-,46+,47+,48+,49+/m1/s1

InChI key

JAYAGJDXJIDEKI-PTGWOZRBSA-N

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Application


  • Cardiac glycoside sensitization in hepatocellular carcinoma: Research demonstrated that Lanatoside C enhances the sensitivity of hepatocellular carcinoma cells to TRAIL-induced apoptosis through mechanisms involving reactive oxygen species generation, p38MAPK activation, and modulation of mitochondrial transition and autophagy (Rasheduzzaman et al., 2019).

  • Elimination of undifferentiated human embryonic stem cells: Lanatoside C has been shown to selectively eliminate undifferentiated human embryonic stem cells, indicating its potential use in ensuring the safety of stem cell-derived therapies (Lin et al., 2017).

Other Notes

To gain a comprehensive understanding of our extensive range of Oligosaccharides for your research, we encourage you to visit our Carbohydrates Category page.

Pictograms

Skull and crossbonesHealth hazard

Signal Word

Danger

Hazard Statements

Hazard Classifications

Acute Tox. 2 Inhalation - Acute Tox. 3 Oral - STOT RE 2

Storage Class Code

6.1A - Combustible acute toxic Cat. 1 and 2 / very toxic hazardous materials

WGK

WGK 3

Flash Point(F)

Not applicable

Flash Point(C)

Not applicable


Certificates of Analysis (COA)

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A Tracqui et al.
Journal of chromatography. B, Biomedical sciences and applications, 692(1), 101-109 (1997-04-25)
An original method based upon high-performance liquid chromatography coupled to ionspray mass spectrometry (HPLC-ISP-MS) has been developed for the identification and quantification in plasma of several cardiac glycosides, namely digoxin, digitoxin, lanatoside C and acetyldigitoxin. After single-step liquid-liquid extraction by
Davy Guillarme et al.
Journal of chromatography. A, 1216(15), 3232-3243 (2009-03-03)
The UHPLC strategy which combines sub-2 microm porous particles and ultra-high pressure (>1000 bar) was investigated considering very high resolution criteria in both isocratic and gradient modes, with mobile phase temperatures between 30 and 90 degrees C. In isocratic mode
Min-Wu Chao et al.
Scientific reports, 7, 46134-46134 (2017-04-08)
Recent studies have revealed that cardiac glycosides, such as digitalis and digoxin, have anticancer activity and may serve as lead compounds for the development of cancer treatments. The poor prognosis of hepatocellular carcinoma (HCC) patients reflects the development of resistance
F Orosz et al.
Analytical biochemistry, 156(1), 171-175 (1986-07-01)
A rapid extraction method followed by high-performance liquid chromatographic assay was developed for the quantitative determination of the cardioactive glycosides of Digitalis lanata. The leaf samples were extracted with water or aqueous alcohols. The simple extraction method gives a better
Yoshihiro Ueda et al.
The Journal of organic chemistry, 77(18), 7850-7857 (2012-08-09)
Acylation of lanatoside C in the presence of organocatalyst 5 gave the C(4'''')-O-acylate in up to 90% regioselectivity (catalyst-controlled regioselectivity). Various functionalized acyl groups can be introduced at the C(4'''')-OH by a mixed anhydride method in the presence of 5

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