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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:
17575-22-3
Molecular Weight:
985.12
EC Number:
241-546-1
MDL number:
MFCD00869432
UNSPSC Code:
12352201
PubChem Substance ID:
24896307
NACRES:
NA.25

Quality Level

100

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
GHS06,GHS08

Signal Word

Danger

Hazard Statements

H301,H330,H373

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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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
Dhanasekhar Reddy et al.
Biomolecules, 9(12) (2019-12-01)
Cardiac glycosides (CGs) are a diverse family of naturally derived compounds having a steroid and glycone moiety in their structures. CG molecules inhibit the α-subunit of ubiquitous transmembrane protein Na+/K+-ATPase and are clinically approved for the treatment of cardiovascular diseases.
A Takeshita et al.
Japanese circulation journal, 50(7), 671-674 (1986-07-01)
We examined whether digitalis augments cardiopulmonary baroreflex control of forearm vascular resistance in normal young men. Cardiopulmonary baroreceptor input was reduced with lower body negative pressure (LBNP) at 10 and 20 mmHg which decreased central venous pressure (CVP) but did
T Imamura et al.
Circulation, 71(1), 11-16 (1985-01-01)
We sought to determine whether digitalis augments cardiopulmonary baroreflex control of forearm vascular resistance in normal young men. Cardiopulmonary baroreceptor input was reduced with lower body negative pressure (LBNP) at 10 and 20 mm Hg, which decreased central venous pressure
Christian E Badr et al.
Neuro-oncology, 13(11), 1213-1224 (2011-07-16)
Human glioblastoma (GBM) cells are notorious for their resistance to apoptosis-inducing therapeutics. We have identified lanatoside C as a sensitizer of GBM cells to tumor necrosis factor-related apoptosis-inducing ligand (TRAIL)-induced cell death partly by upregulation of the death receptor 5.
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