Marinobufagenin

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]

Marinobufagenin
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
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 ☒N
    Key: JMNQTHQLNRILMH-OBBGIPBRSA-N ☒N
  • 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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Infobox references

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.


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