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Steroid


DATA No : SST0003 INFORMANT : Hideaki Nishino

NAME : 16-(Acetyloxy)-3,14-dihydroxybufa-20,22-dienolide / 3b,14,16b-Trihydroxy-5b-bufa-20,22-dienolide 16-acetate

COMMON NAME: Bufotalin
SYMBOL:
FORMULA: C26H36O6 MOL.WT (average) : 444.560


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BIOLOGICAL ACTIVITY
Cardiotoxic steroid. Applied for Chinese medicine named Senso as cardiotonic agent. (Ref. 0011/0012/0013/0014/0015/0016)
PHYSICAL AND CHEMICAL PROPERTIES
MELTING POINT:269-272 degC (3-acetate), 233 degC (free) (Ref. 0013)

BOILING POINT:

REFRACTIVE INDEX:

OPTICAL ROTATION:[a]20/D=+5.4deg (c=0.5 in CHCl3) (Ref. 0013)

DENSITY:

SOLUBILITY:Sol in alcohol, chloroform (Ref. 0017)
SPECTRAL DATA
UV SPECTRA:max. 300 nm (Ref. 0015)

IR SPECTRA:

NMR SPECTRA:1H n.m.r. (100 MHz), employing spin-decoupling experiments, lead to the following assignments: the pyrone ring protons, d 6.17 (Ha, Doublet, Jab 9Hz, Jac 1Hz), 8.04 (Hb, Quartet, Jab 9Hz, Jbc 2.7Hz), 7.24 (Hc), while in ring D the 17a-proton Hd appeared as a doublet at d 2.72, J 9Hz. Because Jed and Jef were both 9Hz, He corresponded to a sextet at d 5.54 with Jeg 2 Hz. The methylene protons Hf and Hg gave signals at d 2.66 and 1.9, respectively. (Ref. 0016)

MASS SPECTRA:m/e: 444 (M, 5%) (M for C26H36O6=444); 384 (M-60, 100%); 336 (M-60-18, 61%); 351 (M-60-18-15, 9%); 348 (M-60-36, 10%); 341 (M-60-43, 80%); 323 (M-60-43-18, 68%). Metastable ion peaks at m/e 332.0 (440 to 384), 349.0 (384 to 366), and 303.0 (384 to 341) were observed. (Ref. 0016)

OTHER SPECTRA:
CHROMATOGRAM DATA

SOURCE
Predominant constituent of dermal gland secretion, toad poison. Component of bufotoxin. (Ref. 0011/0012/0013/0014/0015/0016/0017)
CHEMICAL SYNTHESIS
A couple of methods for partial synthesis. Prepare the 16-ketone of cinobufagin, reduce 14,15b-epoxide group with chromous acetate to yield b-hydroxy ketone and a,b-unsaturated ketone. Selectively reduce the b-hydroxy ketone with Urushibara nickel A to produce alcohol, which is acetylated to provide diacetate. Treat the diacetate with HCl in methanol to give bufotalin. Alternatively reduce first the a,b-unsaturated ketone with Urushibara nickel A to allylic alcohol. After acetylation subject the olefin to hypoiodous acid or hypobromous acid, then treat the resulting halohydrin with Urushibara nickel A. Hydrogenolyze the product to bufotalin 3b-acetate. (Ref. 0018)
METABOLISM

GENETIC INFORMATION

NOTE

REFERENCES
[0011]
AUTHOR:Faust,E.S.
TITLE:Ueber Bufonin und Bufotalin, die Wirksamen Bestandtheile des Krötenhautdüsecretes
JOURNAL:Arch.Exp.Pathol.Pharmakol.
VOL:47 PAGE : 278 -310 (1902)
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[0012]
AUTHOR:Faust,E.S.
TITLE:Weitere Beiträge zur Kenntniss der Wirksamen Bestandtheile des Krötenhautdrüsensecretes.
JOURNAL:Arch.Exp.Pathol.Pharmakol.
VOL:49 PAGE : 1 -6 (1902)
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[0013]
AUTHOR:Wieland,H., and Weil,F.J.
TITLE:Über das Krötengift.
JOURNAL:Ber.
VOL:46 PAGE : 3315 -3327 (1913)
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[0014]
AUTHOR:Wieland,H., Hesse,G., and Hüttel,R.
TITLE:Zur Kenntnis der Krötengiftstoffe. IX. Weiteres zur Konstitutionsfrage.
JOURNAL:Justus Liebigs Ann Chem.
VOL:524 PAGE : 203 -222 (1936)
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[0015]
AUTHOR:Meyer,K.
TITLE:Über Herzaktive Krötengifte (Bufogenine). 5. Mitteilung. Konstitution des Bufotalins.
JOURNAL:Helv.Chim.Acta
VOL:32 PAGE : 1993 -2003 (1949)
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[0016]
AUTHOR:Pettit,G.R., Brown,P., Bruschweiler,F., and Houghton,L.E.
TITLE:Structure of the Bufadienolide Bufotalin
JOURNAL:J.Chem.Soc.,Chem.Commun.
VOL:1970 PAGE : 1566 -1567 (1970)
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[0017]
AUTHOR:Monographs in the Merck Index an encyclopedia of chemicals, drugs, and biologicals (Budavari,S., O'Neil,M.J., Smith,A., and Heckelman,P.E.,eds. 1989), pp224-224, MERCK & CO., Inc. Rahway, N.J.
TITLE:
JOURNAL:
VOL: PAGE : - ()
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[0018]
AUTHOR:Kamano, Y., Pettit, G. R., and Inoue, M.
TITLE:Bufadienolides. 29. Synthetic routes to bufotalin PubMed ID:4412262
JOURNAL:J Org Chem.
VOL:39 PAGE : 3007-3013 (1974)
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Last updated June 19, 2007. Copyright © 1989-2007 Japanese Conference on the Biochemistry of Lipids (JCBL). All rights reserved.