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Bufadienolide information


Bufadienolide
Names
IUPAC name
5-[(5R, 8R,9S,10S,13S,14S,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]pyran-2-one
Identifiers
CAS Number
  • 29565-35-3 ☒N[EPA]
3D model (JSmol)
  • Interactive image
ChEBI
  • CHEBI:83977 checkY
ChemSpider
  • 26286947 checkY
PubChem CID
  • 3035030
CompTox Dashboard (EPA)
  • DTXSID70276154 Edit this at Wikidata
InChI
  • InChI=1S/C24H34O2/c1-23-13-4-3-5-17(23)7-8-18-20-10-9-19(16-6-11-22(25)26-15-16)24(20,2)14-12-21(18)23/h6,11,15,17-21H,3-5,7-10,12-14H2,1-2H3/t17-,18-,19+,20+,21-,23-,24+/m0/s1 checkY
    Key: YBPMPRDOWHIVNA-JTSGVHQASA-N checkY
  • InChI=1S/C24H34O2/c1-23-13-4-3-5-17(23)7-8-18-20-10-9-19(16-6-11-22(25)26-15-16)24(20,2)14-12-21(18)23/h6,11,15,17-21H,3-5,7-10,12-14H2,1-2H3/t17-,18-,19+,20+,21-,23-,24+/m0/s1
    Key: YBPMPRDOWHIVNA-JTSGVHQASA-N
SMILES
  • CC14CCC3C2(C)CCCCC2CCC3C1CCC4c5ccc(=O)oc5
Properties
Chemical formula
C24H34O2
Molar mass 354.534 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

Bufadienolide is a chemical compound with steroid structure. Its derivatives are collectively known as bufadienolides, including many in the form of bufadienolide glycosides (bufadienolides that contain structural groups derived from sugars). 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 (slow heartbeat), ventricular tachycardia (a type of rapid heartbeat), and possibly lethal cardiac arrest.[1]

  1. ^ Mutschler, Ernst; Schäfer-Korting, Monika (2001). Arzneimittelwirkungen (in German) (8 ed.). Stuttgart: Wissenschaftliche Verlagsgesellschaft. pp. 534, 538. ISBN 3-8047-1763-2.

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Bufadienolide

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Bufadienolide is a chemical compound with steroid structure. Its derivatives are collectively known as bufadienolides, including many in the form of bufadienolide...

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Kalanchoe

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hypertension. A variety of bufadienolide compounds have been isolated from various Kalanchoe species. Five different bufadienolides have been isolated from...

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Daigremontianin

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Daigremontianin is a bufadienolide. Bufadienolides are steroids and cardiac glycoside aglycones (meaning that they bind with carbohydrates to form cardiac...

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Kalanchoe pinnata

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Cotyledon and Adromischus), Kalanchoe pinnata has been found to contain bufadienolide cardiac glycosides These can cause cardiac poisoning, particularly in...

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Cardiac glycoside

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it to be classified as either a cardenolide or bufadienolide. Cardenolides differ from bufadienolides due to the presence of an "enolide," a five-membered...

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Kalanchoe delagoensis

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delagoensis is unwelcome because it displaces native plants and contains bufadienolide cardiac glycosides which can cause fatal poisoning, particularly in...

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Bryophyllum

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cotyledonosis. Kalanchoe pinnata may have similar chemical components, bufadienolide alkaloids. Descoings, B. (2006). "Le genre Kalanchoe (Crassulaceae):...

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Bufotoxin

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found in toads can be divided by chemical structure in two groups: bufadienolides, which are cardiac glycosides (e.g., bufotalin, bufogenin), are undesirable...

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Bufanolide

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Bufanolide is a C24 steroid and, indirectly, a parent structure of bufadienolide. Its derivatives was found in Bufo and Scilla, as an aglycone of cardiac...

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Arenobufagin

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a derivative of the so-called bufadienolides, where it also has a steroid structure. A characteristic of bufadienolides is that they all contain two double...

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Lactone

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in substance class names like butenolide, macrolide, cardenolide or bufadienolide. To obtain the preferred IUPAC names, lactones are named as heterocyclic...

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List of poisonous plants

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dermatitis. Kalanchoe delagoensis mother of millions Crassulaceae Contains bufadienolide cardiac glycosides which can cause cardiac poisoning, particularly in...

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Eranthis hyemalis

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glycosides present in E.hyemalis include Eranthin A and B, belonging to the bufadienolide group, also found in (and named for) the toad venom bufotoxin. Bulbs...

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Eranthis

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the toxic compounds present being mainly cardiac glycosides of the bufadienolide group similar to those found in Adonis vernalis, rather than the virulent...

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Marinobufagenin

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Marinobufagenin (marinobufagin) is a cardiotonic bufadienolide steroid. It can be found in the plasma and urine of human subjects with myocardial infarction...

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Cardenolide

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digoxigenin digoxin medigoxin neoconvalloside ouabain strophanthidin Bufadienolide and marinobufagenin are similar in structure and function. Cardanolide...

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Firefly

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contain the steroid pyrones lucibufagins, similar to the cardiotonic bufadienolides found in some poisonous toads. All fireflies glow as larvae, where bioluminescence...

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Drimia maritima

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The main active compounds are cardiac glycosides, including unique bufadienolides such as glucoscillaren A, proscillaridine A, scillaren A, scilliglaucoside...

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Bufagin

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respect to 0.1 gram of epinephrin presented. Bufagin and bufagins are bufadienolide derivatives. This means they are steroids with a six-membered lactone...

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Kalanchoe daigremontiana

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Wagner, Hildebert; Fischer, Manfred; Lotter, Hermann (1985). "New Bufadienolides from Kalanchoe daigremontiana Hamet et Perr. (Crassulaceae)" (PDF)....

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Cotyledon tomentosa

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glycosides, including bufadienolides, which are highly toxic to cattle, sheep, goats, and other livestock. The bufadienolides found in Cotyledon cause...

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Common toad

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Knight, J. C. (1987). "Steroids and related natural products. 104. Bufadienolides. 36. Synthesis of bufalitoxin and bufotoxin". Journal of Organic Chemistry...

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Poisonous amphibian

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venom Brazil Panamanian golden frog (Atelopus zeteki) Zetekitoxin AB, Bufadienolide Central Panama. American toad (Anaxyrus americanus) Bufotoxin eastern...

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Crassulaceae

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highest concentration of cardiotoxins, the active ingredient being bufadienolides (named for their digoxin-like effect on Bufo toads). Illness in domestic...

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Scilloideae

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divide the tribe into 19 genera. Species within this tribe contain bufadienolides and are distributed mainly in Africa, Madagascar, and the Mediterranean...

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Anaxyrus fowleri

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compound from the warts on its back. The secretion, containing toxic bufadienolides, is distasteful to predators and can be lethal to small mammals. The...

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Lucibufagin

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(Lucibufagin A, B, and C), and are in the same structural class as the bufadienolides. v t e v t e P.J. Leisch (Summer 2018). "Five things everyone should...

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Panamanian golden frog

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Panamanian golden frog has a variety of toxins, including steroidal bufadienolides and guanidinium alkaloids of the tetrodotoxin class. One of the latter...

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Tylecodon wallichii

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from Namaqualand into the Great and Little Karoo. The plant contains bufadienolide-type cardiac glycoside cotyledoside which causes nenta poisoning ("krimpsiekte")...

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