Gephyrotoxins, Histrionicotoxins and Pumiliotoxins from the Neotropical Frog <i>Dendrobates histrionicus</i>
書誌事項
- 公開日
- 1977-04-20
- 権利情報
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- http://onlinelibrary.wiley.com/termsAndConditions#vor
- DOI
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- 10.1002/hlca.19770600336
- 10.1002/chin.197731320
- 公開者
- Wiley
この論文をさがす
説明
<jats:title>Abstract</jats:title><jats:p>The structure and absolute configuration of a new acetylenic alkaloid gephyrotoxin isolated from skin extracts of the Colombian frog <jats:italic>Dendrobates histrionicus</jats:italic>, has been determined by Röntgen‐ray crystallography. Gephyrotoxin, previously referred to as HTX‐D, is a novel tricyclic alkaloid, [1 <jats:italic>S</jats:italic>, 3a<jats:italic>S</jats:italic>, 5a<jats:italic>S</jats:italic>, 6<jats:italic>S</jats:italic>(<jats:italic>Z</jats:italic>), 9a <jats:italic>R</jats:italic>, 10 <jats:italic>R</jats:italic>]dodeca‐hydro‐6‐(2‐penten‐4‐yl)pyrrolo[1,2‐a]quinoline‐1‐ethanol. Dihydrogephyrotoxin, a minor skin constituent, contains a 6‐(2,4‐pentadienyl)substituent. Two further spiropiperidine alkaloids related in structure to histrionicotoxin, (6 <jats:italic>R</jats:italic>[6α[2<jats:italic>S</jats:italic>*(<jats:italic>Z</jats:italic>)],[7β(<jats:italic>Z</jats:italic>), 8α]]7‐(1‐buten‐3‐ynyl)‐2‐(2‐penten‐4‐ynyl)‐1‐aza<jats:italic>spiro</jats:italic> [5.5]undecan‐8‐ol), have been isolated from <jats:italic>Dendrobates histrionicus</jats:italic>: allodihydrohistrionicotoxin which differs from histrionicotoxin in having a 2‐(4‐pentynyl)‐substituent, while allotetrahydrohistrio‐nicotoxin, a minor constituent, has 2‐(4‐pentynyl)‐ and 7‐(1,3‐butadienyl)‐substituents. Three alkaloids related in structure to pumiliotoxin C, ([2 <jats:italic>S</jats:italic>, 4a <jats:italic>S</jats:italic>, 5<jats:italic>R</jats:italic>, 8a <jats:italic>R</jats:italic>]5‐methyl‐2‐<jats:italic>n</jats:italic>‐propyl‐<jats:italic>cis</jats:italic>‐decahydroquinoline), have been isolated from <jats:italic>Dendrobates histrionicus</jats:italic>. These alkaloids, with molecular weights of 195, 223, and 269, have, respectively, a 2‐butylsubstituent, 2‐propyl and 5‐propyl‐substituents, and 2‐(3,4‐pentadienyl) and 5‐(2‐penten‐4‐ynyl)‐substituents. The last compound was hydrogenated to a dodecahydro‐derivative identical in molecular weight, but not in other properties, with authentic dodecahydro‐8‐deoxy‐histrionicotoxin, which was prepared from histrionicotoxin. Gephyrotoxin, in contrast to histrionicotoxin and pumiliotoxin C, is a muscarinic antagonist.</jats:p>
収録刊行物
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- Helvetica Chimica Acta
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Helvetica Chimica Acta 60 (3), 1128-1140, 1977-04-20
Wiley