Cymarin

Last updated
Cymarin
Cymarine.png
Clinical data
Other namesCymarine; K-Strophanthin-α; NSC 7522; Strophantin K; WV 90043a; k-Strophanthin-α
ATC code
Identifiers
  • (3S,5S,8R,10S,13R,14S,17R)-5,14-dihydroxy-3-((2R,4S,5S,6R)-5-hydroxy-4-methoxy-6-methyltetrahydro-2H-pyran-2-yloxy)-13-methyl-17-(5-oxo-2,5-dihydrofuran-3-yl)hexadecahydro-1H-cyclopenta[a]phenanthrene-10-carbaldehyde
CAS Number
PubChem CID
ChemSpider
UNII
ChEMBL
ECHA InfoCard 100.007.353 OOjs UI icon edit-ltr-progressive.svg
Chemical and physical data
Formula C30H44O9
Molar mass 548.673 g·mol−1
3D model (JSmol)
Melting point 148 °C (298 °F)
  • 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](OC)C3)C)CC[C@]45C=O
  • InChI=1S/C30H44O9/c1-17-26(33)23(36-3)13-25(38-17)39-19-4-9-28(16-31)21-5-8-27(2)20(18-12-24(32)37-15-18)7-11-30(27,35)22(21)6-10-29(28,34)14-19/h12,16-17,19-23,25-26,33-35H,4-11,13-15H2,1-3H3/t17-,19+,20-,21+,22-,23+,25+,26-,27-,28+,29+,30+/m1/s1 Yes check.svgY
  • Key:XQCGNURMLWFQJR-ZNDDOCHDSA-N Yes check.svgY
 X mark.svgNYes check.svgY  (what is this?)    (verify)

Cymarin (or cymarine) is a cardiac glycoside. Plants of the genus Apocynum , including Apocynum cannabinum and Apocynum venetum , contain cymarin. [1] Cymarin is a cardiac glycoside and an anti-arrhythmia and cardiotonic agent. [2]

Related Research Articles

<span class="mw-page-title-main">Cardiac glycoside</span> Class of organic compounds

Cardiac glycosides are a class of organic compounds that increase the output force of the heart and decrease its rate of contractions by inhibiting the cellular sodium-potassium ATPase pump. Their beneficial medical uses are as treatments for congestive heart failure and cardiac arrhythmias; however, their relative toxicity prevents them from being widely used. Most commonly found as secondary metabolites in several plants such as foxglove plants, these compounds nevertheless have a diverse range of biochemical effects regarding cardiac cell function and have also been suggested for use in cancer treatment.

<i>Digitalis</i> Genus of flowering plants in the family Plantaginaceae

Digitalis is a genus of about 20 species of herbaceous perennial plants, shrubs, and biennials, commonly called foxgloves.

<i>Asclepias tuberosa</i> Species of flowering plant

Asclepias tuberosa, commonly known as butterfly weed, is a species of milkweed native to eastern and southwestern North America. It is commonly known as butterfly weed because of the butterflies that are attracted to the plant by its color and its copious production of nectar.

<span class="mw-page-title-main">Apocynaceae</span> Dogbane and oleander family of flowering plants

Apocynaceae is a family of flowering plants that includes trees, shrubs, herbs, stem succulents, and vines, commonly known as the dogbane family, because some taxa were used as dog poison Members of the family are native to the European, Asian, African, Australian, and American tropics or subtropics, with some temperate members. The former family Asclepiadaceae is considered a subfamily of Apocynaceae and contains 348 genera. A list of Apocynaceae genera may be found here.

<i>Apocynum</i> Genus of flowering plants

Apocynum, commonly known as dogbane or Indian hemp, is a small genus of the flowering plant family Apocynaceae. Its name comes from Ancient Greek ἀπόκυνονapókunon, from ἀπο-apo- "away" and κύωνkúōn "dog", referring to dogbane, which was used to poison dogs. The genus is native to North America, temperate Asia, and southeastern Europe.

<i>Apocynum cannabinum</i> Species of plant

Apocynum cannabinum is a perennial herbaceous plant that grows throughout much of North America—in the southern half of Canada and throughout the United States. It is poisonous to humans, dogs, cats, and horses. All parts of the plant are toxic and can cause cardiac arrest if ingested. Some Lepidoptera feed on this plant, such as a hummingbird moth.

<span class="mw-page-title-main">Phytochemistry</span> Study of phytochemicals, which are chemicals derived from plants

Phytochemistry is the study of phytochemicals, which are chemicals derived from plants. Phytochemists strive to describe the structures of the large number of secondary metabolites found in plants, the functions of these compounds in human and plant biology, and the biosynthesis of these compounds. Plants synthesize phytochemicals for many reasons, including to protect themselves against insect attacks and plant diseases. The compounds found in plants are of many kinds, but most can be grouped into four major biosynthetic classes: alkaloids, phenylpropanoids, polyketides, and terpenoids.

<span class="mw-page-title-main">Cerberin</span> Chemical compound

Cerberin is a type of cardiac glycoside, a steroidal class found in the seeds of the dicotyledonous angiosperm genus Cerbera; including the suicide tree and the sea mango. This class includes digitalis-like agents, channel-blockers that as a group have found historic uses as cardiac treatments, but which at higher doses are extremely toxic; in the case of cerberin, consumption of the C. odollam results in poisoning with presenting nausea, vomiting, and abdominal pain, often leading to death. The natural product has been structurally characterized, its toxicity is clear—it is often used as an intentional human poison in third-world countries, and accidental poisonings with fatalities have resulted from individuals even indirectly consuming the agent—but its potentially therapeutic pharmacologic properties are very poorly described.

<i>Eranthis hyemalis</i> Species of flowering plant in the family Ranunculaceae

Eranthis hyemalis, the winter aconite, is a species of flowering plant in the buttercup family Ranunculaceae, native to calcareous woodland habitats in France, Italy and the Balkans, and widely naturalized elsewhere in Europe.

<i>Adonis vernalis</i> Species of flowering plant in the buttercup family Ranunculaceae

Adonis vernalis, known variously as pheasant's eye, spring pheasant's eye, yellow pheasant's eye and false hellebore, is a perennial flowering plant in the buttercup family Ranunculaceae. It is found in dry meadows and steppes in Eurasia. More specifically, this plant grows in a wide range of locations which include open forests, forest clearings, dry meadows, mesic steppe, and mostly calcareous soil. Isolated populations are found from Spain in the west across Central Europe with fine examples in Valais, Switzerland, and southern Europe, reaching southern Sweden in the north and Abruzzo in the south, with its main area of distribution being the Pannonian Basin and the West Siberian Plain. In contrast to most other European Adonis species, the flowers appear in springtime, and are up to 80 mm (3.1 in) in diameter, with up to 20 bright yellow petals. Not only do the flowers begin to grow, but so do the plants aerial organs, from around April to May.

<i>Calotropis</i> Genus of flowering plants

Calotropis is a genus of flowering plants in the family Apocynaceae, first described as a genus in 1810. It is native to southern Asia and North Africa.

<i>Apocynum androsaemifolium</i> Species of plant

Apocynum androsaemifolium, the fly-trap dogbane or spreading dogbane, is a flowering plant in the Gentianales order. It is common in North America.

<span class="mw-page-title-main">Proscillaridin</span> Chemical compound

Proscillaridin is a cardiac glycoside, a kind of drug that can be used in the treatment of congestive heart failure and cardiac arrhythmia. It is of the bufanolide type and can be obtained from plants of the genus Scilla and in Drimia maritima.

<i>Euchaetes egle</i> Species of moth

Euchaetes egle, the milkweed tiger moth or milkweed tussock moth, is a moth in the family Erebidae and the tribe Arctiini, the tiger moths. The species was first described by Dru Drury in 1773. It is a common mid- through late summer feeder on milkweeds and dogbane. Like most species in this family, it has chemical defenses it acquires from its host plants, in this case, cardiac glycosides. These are retained in adults and deter bats, and presumably other predators, from feeding on them. Only very high cardiac glycoside concentrations deterred bats, however. Adults indicate their unpalatability to bats with ultrasonic clicks from their tymbal organs.

<span class="mw-page-title-main">Daigremontianin</span> Chemical compound

Daigremontianin is a bufadienolide. Bufadienolides are steroids and cardiac glycoside aglycones that are similar to cardenolides, differing only in the structure of the C-17 substituent on the D ring. This chemical has been found to be toxic in experiments on mice. It is one of five bufadienolides that have been isolated from Kalanchoe daigremontiana.

<span class="mw-page-title-main">Cardenolide</span> Chemical compound

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.

<span class="mw-page-title-main">Bufadienolide</span> Chemical compound

Bufadienolide is a chemical compound with steroid structure. Its derivatives are collectively known as bufadienolides, including many in the form of bufadienolide glycosides. These are a type of cardiac glycoside, the other being the cardenolide glycosides. Both bufadienolides and their glycosides are toxic; specifically, they can cause an atrioventricular block, bradycardia, ventricular tachycardia, and possibly lethal cardiac arrest.

k-Strophanthidin Chemical compound

k-Strophanthidin is a cardenolide found in species of the genus Strophanthus. It is the aglycone of k-strophanthin, an analogue of ouabain. k-strophanthin is found in the ripe seeds of Strophanthus kombé and in the lily Convallaria.

<i>Erysimum cheiranthoides</i> Species of flowering plant

Erysimum cheiranthoides, the treacle-mustard,wormseed wallflower, or wormseed mustard is a species of Erysimum native to most of central and northern Europe and northern and central Asia. Like other Erysimum species, E. cheiranthoides accumulates two major classes of defensive chemicals, glucosinolates and cardiac glycosides.

<span class="mw-page-title-main">Oleandrin</span> Chemical compound

Oleandrin is a cardiac glycoside found in the poisonous plant oleander. As a main phytochemical of oleander, oleandrin is associated with the toxicity of oleander sap, and has similar properties to digoxin.

References

  1. Tilford GL. Edible and Medicinal plants of the West. ISBN   0-87842-359-1.
  2. CID 441853 from PubChem