Convallatoxin | CAS#508-75-8 | cardiac glycoside

MedKoo Cat#: 461289 | Name: Convallatoxin

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Description:

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

Convallatoxin is a cardiac glycoside extracted from Convallaria majalis. It is mainly used for acute and chronic heart failure.

Chemical Structure

Convallatoxin

CAS#508-75-8

Theoretical Analysis

MedKoo Cat#: 461289

Name: Convallatoxin

CAS#: 508-75-8

Chemical Formula: C29H42O10

Exact Mass: 550.2778

Molecular Weight: 550.64

Elemental Analysis: C, 63.26; H, 7.69; O, 29.06

Price and Availability

Size	Price	Availability	Quantity
5mg	USD 380.00	2 Weeks
10mg	USD 680.00	2 Weeks

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Synonym

Convallatoxin; Corglykon; Korglykon; Strophanthidin α-L-rhamnopyranoside; Corglycone; Convallaton

IUPAC/Chemical Name

(3S,5S,8R,9S,10S,13R,14S,17R)-5,14-dihydroxy-13-methyl-17-(5-oxo-2,5-dihydrofuran-3-yl)-3-(((2R,3R,4R,5R,6S)-3,4,5-trihydroxy-6-methyltetrahydro-2H-pyran-2-yl)oxy)hexadecahydro-10H-cyclopenta[a]phenanthrene-10-carbaldehyde

InChi Key

HULMNSIAKWANQO-JQKSAQOKSA-N

InChi Code

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

SMILES Code

O=C1OCC([C@H]2CC[C@]3(O)[C@]4([H])CC[C@]5(O)C[C@@H](O[C@H]6[C@@H]([C@@H]([C@H]([C@H](C)O6)O)O)O)CC[C@]5(C=O)[C@@]4([H])CC[C@]23C)=C1

Appearance

Solid powder

Purity

>60% (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 ethanol

Shelf Life

>3 years if stored properly

Drug Formulation

This drug may be formulated in ethanol

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

Product Data

Product Data

Instruction

View handling instruction

Biological target:

Convallatoxin ameliorates colitic inflammation via activation of PPARγ and suppression of NF-κB.

In vitro activity:

Stimulation of mouse macrophages with lipopolysaccharide induced secretion of proinflammatory cytokines via suppression of peroxisome proliferator-activated receptor gamma (PPARγ) and activation of nuclear factor-κB (NF-κB), two transcription factors implicated in many inflammatory diseases. Notably, the effects of lipopolysaccharide were reversed by concomitant treatment of macrophages with CNT (convallatoxin). Reference: Pharmacol Res. 2019 Sep;147:104355. https://pubmed.ncbi.nlm.nih.gov/31386886/

In vivo activity:

Finally, in vivo observations were confirmed by showing antitumor activity of convallatoxin in a murine xenograft model. Reference: Phytomedicine. 2020 Mar;68:153172. https://pubmed.ncbi.nlm.nih.gov/32004989/

	Solvent	mg/mL	mM	comments
Solubility
	Ethanol	20.0	36.32

Note: There can be variations in solubility for the same chemical from different vendors or different batches from the same vendor. The following factors can affect the solubility of the same chemical: solvent used for crystallization, residual solvent content, polymorphism, salt versus free form, degree of hydration, solvent temperature. Please use the solubility data as a reference only. Warming and sonication will facilitate dissolving. Still have questions? Please contact our Technical Support scientists.

Preparing Stock Solutions

The following data is based on the product molecular weight 550.64 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:

1. Zhang Y, Shi X, Han J, Peng W, Fang Z, Zhou Y, Xu X, Lin J, Xiao F, Zhao L, Lin Y. Convallatoxin Promotes M2 Macrophage Polarization to Attenuate Atherosclerosis Through PPARγ-Integrin αvβ5 Signaling Pathway. Drug Des Devel Ther. 2021 Feb 23;15:803-812. doi: 10.2147/DDDT.S288728. PMID: 33654384; PMCID: PMC7914072. 2. Li MY, Zhang ZH, Wang Z, Zuo HX, Wang JY, Xing Y, Jin CH, Xu GH, Piao LX, Ma J, Jin X. Convallatoxin protects against dextran sulfate sodium-induced experimental colitis in mice by inhibiting NF-κB signaling through activation of PPARγ. Pharmacol Res. 2019 Sep;147:104355. doi: 10.1016/j.phrs.2019.104355. Epub 2019 Aug 3. PMID: 31386886. 3. Zhang ZH, Li MY, Wang Z, Zuo HX, Wang JY, Xing Y, Jin C, Xu G, Piao L, Piao H, Ma J, Jin X. Convallatoxin promotes apoptosis and inhibits proliferation and angiogenesis through crosstalk between JAK2/STAT3 (T705) and mTOR/STAT3 (S727) signaling pathways in colorectal cancer. Phytomedicine. 2020 Mar;68:153172. doi: 10.1016/j.phymed.2020.153172. Epub 2020 Jan 17. PMID: 32004989. 4. Jiang BW, Zhang WJ, Wang Y, Tan LP, Bao YL, Song ZB, Yu CL, Wang SY, Liu L, Li YX. Convallatoxin induces HaCaT cell necroptosis and ameliorates skin lesions in psoriasis-like mouse models. Biomed Pharmacother. 2020 Jan;121:109615. doi: 10.1016/j.biopha.2019.109615. Epub 2019 Nov 7. PMID: 31707343.

In vitro protocol:

In vivo protocol:

1. Zhang ZH, Li MY, Wang Z, Zuo HX, Wang JY, Xing Y, Jin C, Xu G, Piao L, Piao H, Ma J, Jin X. Convallatoxin promotes apoptosis and inhibits proliferation and angiogenesis through crosstalk between JAK2/STAT3 (T705) and mTOR/STAT3 (S727) signaling pathways in colorectal cancer. Phytomedicine. 2020 Mar;68:153172. doi: 10.1016/j.phymed.2020.153172. Epub 2020 Jan 17. PMID: 32004989. 2. Jiang BW, Zhang WJ, Wang Y, Tan LP, Bao YL, Song ZB, Yu CL, Wang SY, Liu L, Li YX. Convallatoxin induces HaCaT cell necroptosis and ameliorates skin lesions in psoriasis-like mouse models. Biomed Pharmacother. 2020 Jan;121:109615. doi: 10.1016/j.biopha.2019.109615. Epub 2019 Nov 7. PMID: 31707343.

1: Fink SL, Robey TE, Tarabar AF, Hodsdon ME. Rapid detection of convallatoxin using five digoxin immunoassays. Clin Toxicol (Phila). 2014 Aug;52(7):659-63. doi: 10.3109/15563650.2014.932366. Epub 2014 Jul 1. PubMed PMID: 24980812; PubMed Central PMCID: PMC4180104. 2: Gozalpour E, Greupink R, Bilos A, Verweij V, van den Heuvel JJ, Masereeuw R, Russel FG, Koenderink JB. Convallatoxin: a new P-glycoprotein substrate. Eur J Pharmacol. 2014 Dec 5;744:18-27. doi: 10.1016/j.ejphar.2014.09.031. Epub 2014 Sep 28. PubMed PMID: 25264938. 3: Welsh KJ, Huang RS, Actor JK, Dasgupta A. Rapid detection of the active cardiac glycoside convallatoxin of lily of the valley using LOCI digoxin assay. Am J Clin Pathol. 2014 Sep;142(3):307-12. doi: 10.1309/AJCPCOXF0O5XXTKD. PubMed PMID: 25125619. 4: Yang SY, Kim NH, Cho YS, Lee H, Kwon HJ. Convallatoxin, a dual inducer of autophagy and apoptosis, inhibits angiogenesis in vitro and in vivo. PLoS One. 2014 Mar 24;9(3):e91094. doi: 10.1371/journal.pone.0091094. eCollection 2014. PubMed PMID: 24663328; PubMed Central PMCID: PMC3963847. 5: Everett JM, Kojima YA, Davis B, Wahed A, Dasgupta A. The iDigoxin Assay is More Sensitive than LOCI Digoxin Assay for Rapid Detection of Convallatoxin, the Active Cardiac Glycoside of Lily of The Valley. Ann Clin Lab Sci. 2015 Spring;45(3):323-6. PubMed PMID: 26116597. 6: Cohen T, Williams JD, Opperman TJ, Sanchez R, Lurain NS, Tortorella D. Convallatoxin-Induced Reduction of Methionine Import Effectively Inhibits Human Cytomegalovirus Infection and Replication. J Virol. 2016 Nov 14;90(23):10715-10727. Print 2016 Dec 1. PubMed PMID: 27654292; PubMed Central PMCID: PMC5110156. 7: Schneider NF, Geller FC, Persich L, Marostica LL, Pádua RM, Kreis W, Braga FC, Simões CM. Inhibition of cell proliferation, invasion and migration by the cardenolides digitoxigenin monodigitoxoside and convallatoxin in human lung cancer cell line. Nat Prod Res. 2016 Jun;30(11):1327-31. doi: 10.1080/14786419.2015.1055265. Epub 2015 Aug 7. PubMed PMID: 26252521. 8: WILDE E. [Clinical experiences with convallatoxin]. Munch Med Wochenschr. 1954 Jan 22;96(4):92-4. Undetermined Language. PubMed PMID: 13144728. 9: CHIAVERINI R, DE ALVES I S, DA SILVA WN, CAMPI R. [Convallatoxin in cardiac insufficiency, with special reference to its immediate effects]. Arq Bras Cardiol. 1958 Dec;11(4):269-88. Portuguese. PubMed PMID: 13628449. 10: DITTERTOVA V, BURAN L, BABULOVA A, SELECKY FV. [Effect of oxyphylline on the cardiotoxic activity of convallatoxin and helveticoside and on their action on the heart-lung preparation of the cat]. Cesk Farm. 1963 Feb 5;12:104-7. Czech. PubMed PMID: 14028075. 11: PROVOTOROVA PP. [ON THE COMPARATIVE ACTION OF CORCHOROZIDE AND CONVALLATOXIN IN ACUTE CORONARY INSUFFICIENCY]. Farmakol Toksikol. 1963 May-Jun;26:284-8. Russian. PubMed PMID: 14051662. 12: FOERSTER W, SZIEGOLEIT W. [ON THE ACUTE AND SUBACUTE TOXICITY OF CONVALLATOXOL IN COMPARISON WITH CONVALLATOXIN AND G-STROPHANTHIN]. Acta Biol Med Ger. 1964;12:434-42. German. PubMed PMID: 14134947. 13: UHLENBRUCK P, SCHMITZ W. [The convallatoxin in its relation to the heart glycosides and to the right insufficiency of the heart]. Dtsch Med Wochenschr. 1954 Nov 12;79(46):1718-22. German. PubMed PMID: 13220160. 14: BETTI C, FRULLI M. [The use of convallatoxin in preoperative care]. Minerva Med. 1956 May 9;47(37):1430-2. Italian. PubMed PMID: 13334111. 15: Frantsuzova SB, Antonenko LI. [Experimental study of the effect of convallatoxin on the main blood circulation parameters in chronic cor pulmonale]. Farmakol Toksikol. 1981 Nov-Dec;44(6):688-92. Russian. PubMed PMID: 7308450. 16: BOLTZE KH, LAUFKE R. [Studies on the isolation of convallatoxin]. Arch Pharm Ber Dtsch Pharm Ges. 1957 Aug-Sep;290/62(8-9):412-21. German. PubMed PMID: 13459367. 17: Garbe G. [Comparative standardization of Convallaria drugs and convallatoxin in guinea pigs]. Arzneimittelforschung. 1967 Oct;17(10):1240-1. German. PubMed PMID: 5632866. 18: FOERSTER W. [ON STRUCTURE-EFFECT RELATIONS IN CARDINOLIDES AND BUFADIENOLIDES. IV. COMPARISON OF THE EFFECT OF A METHYL-, ALDEHYDE- AND CARBINOL SUBSTITUTION OF THE C10-ATOM OF CARDENOLIDES. CONTRIBUTION TO THE PHARMACOLOGY OF CONVALLATOXIN]. Acta Biol Med Ger. 1963;11:234-45. German. PubMed PMID: 14064783. 19: MUELLER JH. [CONVALLATOXIN THERAPY OF COR PULMONALE IN CHRONIC EMPHYSEMA BRONCHITIS]. Z Arztl Fortbild (Jena). 1963 Dec 1;57:1290-2. German. PubMed PMID: 14112843. 20: WALZ L, MAIDHOF E. [Convallatoxin treatment of severe heart insufficiency]. Medizinische. 1955 Jun 4;23:845-50. German. PubMed PMID: 13244144.