Marinobufagenin

Last updated
Marinobufagenin
Marinobufagin.svg
Names
IUPAC name
3β,5-Dihydroxy-14,15-epoxy-5β,14β-bufa-20,22-dienolide
Systematic IUPAC name
5-[(1R,2aR,3aS,3bR,5aS,7S,9aR,9bS,11aR)-5b,7-Dihydroxy-9a,11a-dimethylhexadecahydronaphtho[1′,2′:6,7]indeno[1,7a-b]oxiren-1-yl]-2H-pyran-2-one
Other names
Marinobufagin, Marinobufagenin
Identifiers
3D model (JSmol)
ChemSpider
PubChem CID
UNII
  • InChI=1S/C24H32O5/c1-21-8-5-15(25)12-23(21,27)10-7-17-16(21)6-9-22(2)18(11-19-24(17,22)29-19)14-3-4-20(26)28-13-14/h3-4,13,15-19,25,27H,5-12H2,1-2H3/t15-,16-,17+,18+,19+,21+,22+,23-,24+/m0/s1 X mark.svgN
    Key: JMNQTHQLNRILMH-OBBGIPBRSA-N X mark.svgN
  • InChI=1/C24H32O5/c1-21-8-5-15(25)12-23(21,27)10-7-17-16(21)6-9-22(2)18(11-19-24(17,22)29-19)14-3-4-20(26)28-13-14/h3-4,13,15-19,25,27H,5-12H2,1-2H3/t15-,16-,17+,18+,19+,21+,22+,23-,24+/m0/s1
    Key: JMNQTHQLNRILMH-OBBGIPBRBU
  • C[C@]12CC[C@@H](C[C@]1(CCC3C2CC[C@]4([C@]35[C@H](O5)C[C@@H]4C6=COC(=O)C=C6)C)O)O
Properties
C24H32O5
Molar mass 400.515 g·mol−1
Hazards
Occupational safety and health (OHS/OSH):
Main hazards
Toxic
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
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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, kidney failure, and heart failure. [1] It is also secreted by the toad Bufo rubescens [2] and other related species such as Bufo marinus . It is a vasoconstrictor with effects similar to digitalis. [3]

Related Research Articles

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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.

<span class="mw-page-title-main">Blood pressure</span> Pressure exerted by circulating blood upon the walls of arteries

Blood pressure (BP) is the pressure of circulating blood against the walls of blood vessels. Most of this pressure results from the heart pumping blood through the circulatory system. When used without qualification, the term "blood pressure" refers to the pressure in a brachial artery, where it is most commonly measured. Blood pressure is usually expressed in terms of the systolic pressure over diastolic pressure in the cardiac cycle. It is measured in millimeters of mercury (mmHg) above the surrounding atmospheric pressure, or in kilopascals (kPa).

<span class="mw-page-title-main">Hypertension</span> Long-term high blood pressure in the arteries

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<span class="mw-page-title-main">Common toad</span> Species of amphibian

The common toad, European toad, or in Anglophone parts of Europe, simply the toad, is a frog found throughout most of Europe, in the western part of North Asia, and in a small portion of Northwest Africa. It is one of a group of closely related animals that are descended from a common ancestral line of toads and which form a species complex. The toad is an inconspicuous animal as it usually lies hidden during the day. It becomes active at dusk and spends the night hunting for the invertebrates on which it feeds. It moves with a slow, ungainly walk or short jumps, and has greyish-brown skin covered with wart-like lumps.

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Bufotoxins are a family of toxic steroid lactones or substituted tryptamines of which some are toxic. They occur in the parotoid glands, skin, and poison of many toads and other amphibians, and in some plants and mushrooms. The exact composition varies greatly with the specific source of the toxin. It can contain 5-MeO-DMT, bufagins, bufalin, bufotalin, bufotenin, bufothionine, dehydrobufotenine, epinephrine, norepinephrine, and serotonin. Some authors have also used the term bufotoxin to describe the conjugate of a bufagin with suberylarginine.

Bufagin is a toxic steroid C24H34O5 obtained from toad's milk, the poisonous secretion of a skin gland on the back of the neck of a large toad (Rhinella marina, synonym Bufo marinus, the cane toad). The toad produces this secretion when it is injured, scared or provoked. Bufagin resembles chemical substances from digitalis in physiological activity and chemical structure.

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

Bufotalin is a cardiotoxic bufanolide steroid, cardiac glycoside analogue, secreted by a number of toad species. Bufotalin can be extracted from the skin parotoid glands of several types of toad.

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Cicletanine is a furopyridine low-ceiling diuretic drug, usually used in the treatment of hypertension. The drug is manufactured by Ipsen and marketed by Recordati under the trade name Tenstaten.

<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.

Prehypertension, also known as high normal blood pressure and borderline hypertensive (BH), is a medical classification for cases where a person's blood pressure is elevated above optimal or normal, but not to the level considered hypertension. Prehypertension is now referred to as "elevated blood pressure" by the American College of Cardiology (ACC) and the American Heart Association (AHA). The ACC/AHA define elevated blood pressure as readings with a systolic pressure from 120 to 129 mm Hg and a diastolic pressure under 80 mm Hg, and the European Society of Cardiology and European Society of Hypertension (ESC/ESH) define "high normal blood pressure" as readings with a systolic pressure from 130 to 139 mm Hg and a diastolic pressure 85-89 mm Hg. Readings greater than or equal to 130/80 mm Hg are considered hypertension by ACC/AHA and if greater than or equal to 140/90 mm Hg by ESC/ESH.

<span class="mw-page-title-main">Electrogenic sodium bicarbonate cotransporter 4</span> Protein-coding gene in the species Homo sapiens

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

Arenobufagin is a cardiotoxic bufanolide steroid secreted by the Argentine toad Bufo arenarum. It has effects similar to digitalis, blocking the Na+/K+ pump in heart tissue.

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

Cinobufagin is a cardiotoxic bufanolide steroid secreted by the Asiatic toad Bufo gargarizans. It has similar effects to digitalis and is used in traditional Chinese medicine.

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Salt consumption has been extensively studied for its role in human physiology and impact on human health. Chronic, high intake of dietary salt consumption is associated with hypertension and cardiovascular disease, in addition to other adverse health outcomes. Major health and scientific organizations, such as the World Health Organization, US Centers for Disease Control and Prevention, and American Heart Association, have established high salt consumption as a major risk factor for cardiovascular diseases and stroke.

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

Bufalin is a cardiotonic steroid toxin originally isolated from Chinese toad venom, which is a component of some traditional Chinese medicines.

References

  1. Tian, Jiang (7 September 2010). "Renal ischemia regulates marinobufagenin release in humans". Hypertension. 56 (5): 914–919. doi:10.1161/hypertensionaha.110.155564. PMC   2959137 . PMID   20823380.
  2. Cunha Filho, GA; Schwartz, CA; Resck, IS; Murta, MM; Lemos, SS; Castro, MS; Kyaw, C; Pires Jr, OR; et al. (2005). "Antimicrobial activity of the bufadienolides marinobufagin and telocinobufagin isolated as major components from skin secretion of the toad Bufo rubescens". Toxicon. 45 (6): 777–82. doi:10.1016/j.toxicon.2005.01.017. PMID   15804527.
  3. Fedorova, OV; Talan, MI; Agalakova, NI; Lakatta, EG; Bagrov, AY (2002). "Endogenous ligand of alpha(1) sodium pump, marinobufagenin, is a novel mediator of sodium chloride--dependent hypertension". Circulation. 105 (9): 1122–7. doi: 10.1161/hc0902.104710 . PMID   11877366.