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Cardenolide
From Wikipedia, the free encyclopedia
Cardenolides are a type of steroids. Many plants contain cardenolides in the form of cardenolide glycosides (i.e. cardenolides that contain structural groups derived from sugars; see Glycoside). Cardenolides are toxic (specifically, heart-arresting).
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Supposedly, the term derives from Greek kardiā, heart. It shouldn't be confused with cardanolides. Cardanolides are a class of steroids (or aglycones if viewed as cardiac glycoside constituents), and cardenolides are a subtype of this class (see MeSH D codes list).
Cardenolides are C(23)-steroids with methyl groups at C-10 and C-13 and a five-membered lactone at C-17. They are aglycone constituents of cardiac glycosides and must have at least one double bond in the molecule. The class includes cardadienolides and cardatrienolides. Members include:
- digitoxin
- acetyldigitoxins
- digitoxigenin
- digoxin
- acetyldigoxins
- digoxigenin
- medigoxin
- strophanthins
- cymarine
- ouabain
- strophanthidin
Some plant and animal species use cardenolides as a defense mechanism, most notably the monarch butterflies. Adult monarch butterflies store the cardenolides they have built-up as larvae feeding mostly on milkweeds (Asclepias). The cardenolide content in butterflies deters vertebrate predators, with some exceptions of cardenolide-tolerant predators like black-backed orioles (Icterus abeillei Lesson) and black headed grosbeaks (Pheucticus melanocephalus Swainson) that account for 60% of monarch butterfly mortalities in the overwintering sites in central Mexico.
| Major families of biochemicals | ||
| Peptides | Amino acids | Nucleic acids | Carbohydrates | Nucleotide sugars | Lipids | Terpenes | Carotenoids | Tetrapyrroles | Enzyme cofactors | Steroids | Flavonoids | Alkaloids | Polyketides | Glycosides | ||
| Analogues of nucleic acids: | Types of Glycosides | Analogues of nucleic acids: |
| Bond: | O-glycosidic bond | S-glycosidic bond | N-glycosidic bond | |
|---|---|---|
| Geometry: | α-Glycoside | β-Glycoside | 1,4-Glycoside | 1,6-Glycoside | |
| Glycone: | Glucoside | Fructoside | Glucuronide | |
| Aglycone: | Alcoholic glycoside | Anthraquinone glycoside | Coumarin glycoside | Cyanogenic glycoside | Flavonoid glycoside | Phenolic glycoside | Saponin | Cardiac glycoside | Steviol glycoside | Thioglycoside | Glycosylamine | Bufanolide | Cardenolide | |