Convallatoxin

Convallatoxin

Names
IUPAC name (3S,5S,8R,9S,10S,13R,14S,17R)-5,14-dihydroxy-13-methyl-17-(5-oxo-2H-furan-3-yl)-3-[(2R,3R,4R,5R,6S)-3,4,5-trihydroxy-6-methyloxan-2-yl]oxy-2,3,4,6,7,8,9,11,12,15,16,17-dodecahydro-1H-cyclopenta[a]phenanthrene-10-carbaldehyde
Other names Strophanthin 3alpha-1-rhamnoside ; Strophanthidin alpha-l-rhamnopyranoside; Strophanthidin a-l-rhamnopyranoside; Corglykon;20(22),5beta-cardenolid-19-al-3beta,5beta,14beta-triol-3beta-d-[a-1-rhamnopyranoside] ; 5Beta,20[22]-cardenolide-19-one-3beta,5alpha,14-triol-3-[6-deoxy-alpha-l-mannopyranosyl] ; 3Beta,5alpha,14-trihydroxy-19-oxo-5beta,20[22]-cardenolide-3-[6-deoxy-alpha-l-mannopyranosyl]
Identifiers
CAS Number	508-75-8
ChEBI	CHEBI:27663
ChEMBL	ChEMBL399336
ChemSpider	390428
EC Number	208-086-3
Jmol interactive 3D	Image
PubChem	441852
InChI InChI=1S/C29H42O10/c1-15-22(32)23(33)24(34)25(38-15)39-17-3-8-27(14-30)19-4-7-26(2)18(16-11-21(31)37-13-16)6-10-29(26,36)20(19)5-9-28(27,35)12-17/h11,14-15,17-20,22-25,32-36H,3-10,12-13H2,1-2H3/t15-,17-,18+,19-,20+,22-,23+,24+,25-,26+,27-,28-,29-/m0/s1 Key: HULMNSIAKWANQO-JQKSAQOKSA-N InChI=1/C29H42O10/c1-15-22(32)23(33)24(34)25(38-15)39-17-3-8-27(14-30)19-4-7-26(2)18(16-11-21(31)37-13-16)6-10-29(26,36)20(19)5-9-28(27,35)12-17/h11,14-15,17-20,22-25,32-36H,3-10,12-13H2,1-2H3/t15-,17-,18+,19-,20+,22-,23+,24+,25-,26+,27-,28-,29-/m0/s1 Key: HULMNSIAKWANQO-JQKSAQOKBT
SMILES O=C\1OC/C(=C/1)[C@H]2CC[C@@]6(O)[C@]2(C)CC[C@H]4[C@H]6CC[C@]5(O)C[C@@H](O[C@@H]3O[C@H]([C@H](O)[C@@H](O)[C@H]3O)C)CC[C@]45C=O
Properties
Chemical formula	C29H42O10
Molar mass	550.65 g·mol^−1
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
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Infobox references

Convallatoxin is a glycoside extracted from Convallaria majalis.

Action and uses

Similar to digitalis, it is mainly used for acute and chronic heart failure.

Detection

Convallatoxin can be detected alongside digoxin using luminescent oxygen channelling technology–based digoxin assay LOCI which could possibly detect other glycosides present in plasma derived from Lily of the Valley plant.

Based on the observed apparent digoxin concentration, convallatoxin concentration in the serum can be calculated using a formula: y = 89.9x2 – 524x + 617.3 y = convallotoxin (ng/mL) x = LOCI digoxin concentration (ng/mL)^[1]

References

1. Am J. Clin. Pathol. 2014 Sep;142(3):307-12. doi: 10.1309/AJCPCOXF0O5XXTKD. Rapid detection of the active cardiac glycoside convallatoxin of lily of the valley using LOCI digoxin assay. Welsh KJ, Huang RS, Actor JK, Dasgupta A.