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Cardenolide information


Cardenolide
Names
IUPAC name
3-[(8R,9S,10S,13S,14R,17S)-10,13-dimethyl-2,3,4,5,6,7,8,9,11,12,14,15,16,17-tetradecahydro-1H-cyclopenta[a]phenanthren-17-yl]-2H-furan-5-one
Identifiers
CAS Number
  • 52085-71-9 checkY
3D model (JSmol)
  • Interactive image
  • Interactive image
ChemSpider
  • 19954501 checkY
PubChem CID
  • 3035019
UNII
  • L54QGD9LPW checkY
CompTox Dashboard (EPA)
  • DTXSID40952054 Edit this at Wikidata
InChI
  • InChI=1S/C23H34O 2/c1-22-11-4-3-5-16(22)6-7-17-19-9-8-18(15-13-21(24)25-14-15)23(19,2)12-10-20(17)22/h4,11,15-20H,3,5-10,12-14H2,1-2H3/t15-,16?,17-,18+,19+,20-,22-,23+/m0/s1 checkY
    Key: NMLOFHCUVXKTGV-OCYOQFCJSA-N checkY
  • InChI=1/C23H34O2/c1-22-11-4-3-5-16(22)6-7-17-19-9-8-18(15-13-21(24)25-14-15)23(19,2)12-10-20(17)22/h4,11,15-20H,3,5-10,12-14H2,1-2H3/t15-,16?,17-,18+,19+,20-,22-,23+/m0/s1
    Key: NMLOFHCUVXKTGV-OCYOQFCJBM
SMILES
  • CC12CCCCC1CCC3C2CCC4(C3C=CC4C5CC(=O)OC5)C
  • C[C@]52/C=C\CCC5CC[C@H]1[C@H]3CC[C@@H]([C@@]3(C)CC[C@@H]12)[C@H]4CC(=O)OC4
Properties
Chemical formula
C23H34O2
Molar mass 342.51486
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

A cardenolide is a type of steroid. Many plants contain derivatives, collectively known as cardenolides, including many in the form of cardenolide glycosides (cardenolides that contain structural groups derived from sugars). Cardenolide glycosides are often toxic; specifically, they are heart-arresting. Cardenolides are toxic to animals through inhibition of the enzyme Na+/K+‐ATPase, which is responsible for maintaining the sodium and potassium ion gradients across the cell membranes.[1]

  1. ^ Cite error: The named reference :0 was invoked but never defined (see the help page).

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Cardenolide

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A cardenolide is a type of steroid. Many plants contain derivatives, collectively known as cardenolides, including many in the form of cardenolide glycosides...

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Asclepias

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cardenolides, exuded where cells are damaged. Most species are toxic to humans and many other species, primarily due to the presence of cardenolides....

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Norrish reaction

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can be found early in the total synthesis of the biologically active cardenolide ouabagenin by Phil Baran and coworkers. The optimized conditions minimize...

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Erysimum

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this genus. The evolution of novel chemical defenses in plants, such as cardenolides in the genus Erysimum, is predicted to allow escape from herbivory by...

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Asclepias tuberosa

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successfully. Further, it is one of the very lowest Asclepias species in cardenolide content, making it a poor source of protection from bird predation and...

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Cardiac glycoside

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of the molecule allows it to be classified as either a cardenolide or bufadienolide. Cardenolides differ from bufadienolides due to the presence of an "enolide...

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Erysimum crepidifolium

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both cardiac glycosides (cardenolides), and glucosinolates. All parts of E. crepidifolium are toxic due to their cardenolide content. There are at least...

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Hemiptera

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such as Dolycoris are able to direct these fluids at an attacker. Toxic cardenolide compounds are accumulated by the heteropteran Oncopeltus fasciatus when...

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Monarch butterfly

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the presence of cardenolides in their bodies, which the caterpillars ingest as they feed on milkweed. Monarchs and other cardenolide-resistant insects...

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Bufadienolide

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sugars). These are a type of cardiac glycoside, the other being the cardenolide glycosides. Both bufadienolides and their glycosides are toxic; specifically...

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Cerbera odollam

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[citation needed] The kernels of C. odollam contain cerberin, a digoxin-type cardenolide and cardiac glycoside toxin that blocks the calcium ion channels in heart...

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Digoxin

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Digoxin (better known as Digitalis), sold under the brand name Lanoxin among others, is a medication used to treat various heart conditions. Most frequently...

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Strophanthin

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singular may refer to: g-Strophanthin, also known as ouabain k-Strophanthin Cardenolide This set index article lists chemical compounds articles associated with...

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Chrysochus cobaltinus

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these plants contain toxic molecules known as cardenolides. C.cobaltinus beetles are resistant to cardenolide toxic effects and can further use them for...

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Digitalis atlantica

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also toxic. However, this particular species seems to have the lowest cardenolide content. "Occurrence Detail 474605930". "Taxonomy browser (Digitalis...

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Saponin

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galacturonic acid, which are oxidized forms of glucose and galactose. Cardenolide Cardiac glycoside Phytochemical Hostettmann, K.; A. Marston (1995). Saponins...

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Steroid

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ergosterol, and various phytosterols Toxins such as steroidal saponins and cardenolides/cardiac glycosides As well as the following class of secosteroids (open-ring...

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Cerberin

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moiety. Cerberin, with its five-membered ring, belongs to the cardenolide class; cardenolides are 23-carbon steroids with methyl groups at positions 10 and...

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Calotropin

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Calotropin is a toxic cardenolide found in plants in the family Asclepiadoideae. In extreme cases, calotropin poisoning can cause respiratory and cardiac...

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Chemical defense

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hairs on the leaves, cardenolide toxins, and latex fluids, but Monarchs have evolved to remain unaffected by these defenses. Cardenolide toxins sequestered...

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Calotropis gigantea

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Robin A.; Weber, Marjorie G.; Rasmann, Sergio (April 2012). "Toxic cardenolides: chemical ecology and coevolution of specialized plant–herbivore interactions"...

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Danaus chrysippus

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Asclepias, more commonly called milkweed. Milkweed contains toxic compounds, cardenolides, which are often consumed and stored by many butterflies. Because of...

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Lactone

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is -olide, used in substance class names like butenolide, macrolide, cardenolide or bufadienolide. To obtain the preferred IUPAC names, lactones are named...

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Lily of the valley

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native to North America. Due to the concentration of cardiac glycosides (cardenolides), it is highly poisonous if consumed by humans or other animals. Other...

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Convallatoxin

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Ramos, ACP; Taranto, AG; Pádua, RM (2017). "Cytotoxic effects of the cardenolide convallatoxin and its Na, K-ATPase regulation". Molecular and Cellular...

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Convergent evolution

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(2012). Community-wide convergent evolution in insect adaptation to toxic cardenolides by substitutions in the Na,K-ATPase. Proceedings of the National Academy...

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Erysimum cheiranthoides

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characteristic of the plant family Brassicaceae, and cardiac glycosides (cardenolides), a class of chemicals produced by at least twelve different plant families...

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Adaptation

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"Community-wide convergent evolution in insect adaptation to toxic cardenolides by substitutions in the Na,K-ATPase". Proceedings of the National Academy...

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