Open main menu
Home
Random
Recent changes
Special pages
Community portal
Preferences
About Wikipedia
Disclaimers
Incubator escapee wiki
Search
User menu
Talk
Dark mode
Contributions
Create account
Log in
Editing
Batrachotoxin
(section)
Warning:
You are not logged in. Your IP address will be publicly visible if you make any edits. If you
log in
or
create an account
, your edits will be attributed to your username, along with other benefits.
Anti-spam check. Do
not
fill this in!
==History== Batrachotoxin was discovered by Fritz Märki and [[Bernhard Witkop]], at the National Institute of Arthritis and Metabolic Diseases, National Institutes of Health, [[Bethesda, Maryland]], U.S.A. Märki and Witkop separated the potent toxic alkaloids fraction from ''[[Phyllobates bicolor]]'' and determined its chemical properties in 1963.<ref>{{cite journal |last1=Märki |first1=F. |last2=Witkop |first2=B. |title=The venom of the Colombian arrow poison frog ''Phyllobates bicolor'' |journal=Experientia |date=July 1963 |volume=19 |issue=7 |pages=329–338 |doi=10.1007/BF02152303 |pmid=14067757 |s2cid=19663576 }}</ref> They isolated four major toxic steroidal alkaloids including batrachotoxin, homobatrachotoxin (isobatrachotoxin), pseudobatrachotoxin, and batrachotoxinin A.<ref name=":0" /> Due to the difficulty of handling such a potent toxin and the minuscule amount that could be collected, a comprehensive [[structure determination]] involved several difficulties. However, Takashi Tokuyama, who joined the investigation later, converted one of the [[congener (chemistry)|congener]] compounds, batrachotoxinin A, to a crystalline derivative and its unique steroidal structure was solved with [[x-ray diffraction]] techniques (1968).<ref>{{cite journal |last1=Tokuyama |first1=Takashi |last2=Daly |first2=John |last3=Witkop |first3=B. |last4=Karle |first4=Isabella L. |last5=Karle |first5=J. |title=The structure of batrachotoxinin A, a novel steroidal alkaloid from the Columbian arrow poison frog, Phyllobates aurotaenia |journal=Journal of the American Chemical Society |date=March 1968 |volume=90 |issue=7 |pages=1917–1918 |doi=10.1021/ja01009a052 |pmid=5689118 |bibcode=1968JAChS..90.1917T }}</ref> When the [[mass spectrum]] and [[NMR spectrum]] of batrachotoxin and the batrachotoxinin A derivatives were compared, it was realized that the two shared the same steroidal structure and that batrachotoxin was batrachotoxinin A with a single extra [[pyrrole]] [[Moiety (chemistry)|moiety]] attached. In fact, batrachotoxin was able to be partially [[hydrolyze]]d using [[sodium hydroxide]] into a material with identical TLC and color reactions as batrachotoxinin A.<ref name=":0" /> The structure of batrachotoxin was established in 1969 through chemical recombination of both fragments.<ref name=":0">{{cite journal |last1=Tokuyama |first1=Takashi |last2=Daly |first2=J. |last3=Witkop |first3=B. |title=Structure of batrachotoxin, a steroidal alkaloid from the Colombian arrow poison frog, phyllobates aurotaenia, and partial synthesis of batrachotoxin and its analogs and homologs |journal=Journal of the American Chemical Society |date=1 July 1969 |volume=91 |issue=14 |pages=3931–3938 |doi=10.1021/ja01042a042 |pmid=5814950 |bibcode=1969JAChS..91.3931T }}</ref> Batrachotoxinin A was synthesized by Michio Kurosu, Lawrence R. Marcin, Timothy J. Grinsteiner, and [[Yoshito Kishi]] in 1998.<ref>{{cite journal |last1=Kurosu |first1=Michio |last2=Marcin |first2=Lawrence R. |last3=Grinsteiner |first3=Timothy J. |last4=Kishi |first4=Yoshito |title=Total Synthesis of (±)-Batrachotoxinin A |journal=Journal of the American Chemical Society |date=July 1998 |volume=120 |issue=26 |pages=6627–6628 |doi=10.1021/ja981258g |bibcode=1998JAChS.120.6627K }}</ref>
Edit summary
(Briefly describe your changes)
By publishing changes, you agree to the
Terms of Use
, and you irrevocably agree to release your contribution under the
CC BY-SA 4.0 License
and the
GFDL
. You agree that a hyperlink or URL is sufficient attribution under the Creative Commons license.
Cancel
Editing help
(opens in new window)