Indolizidine alkaloids

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Indolizidine, basic body of indolizidine alkaloids Indolizine Structural Formula V2-Seite001.svg
Indolizidine, basic body of indolizidine alkaloids
Australian chestnut (Castanospermum australe) 200410 Castanospermum australe.JPG
Australian chestnut (Castanospermum australe)
Strawberry poison-dart frog (Dendrobates pumilio) Dendrobates pumilio.jpg
Strawberry poison-dart frog (Dendrobates pumilio)

Indolizidine alkaloids are natural products from various alkaloid groups whose structure can be derived from indolizidine. [1]

Contents

Occurrence

Indolizidine alkaloids are present in various plant families, including Elaeocarpaceae, Asclepiadaceae, and are also produced as metabolites by fungi and bacteria. [2] For instance, Slaframine and swainsonine were identified in the fungus Rhizoctonia leguminicola , [3] while Castanospermine was extracted from Castanospermum australe. [2] Notably, this alkaloid group includes pumiliotoxins, which are the toxins of the strawberry poison-dart frog . [2]

Representatives

Polyhydroxy alkaloids

The polyhydroxy alkaloids include compounds like castanospermine and swainsonine. [1]

Pumiliotoxins

The primary alkaloids within the pumiliotoxin category are pumiliotoxin A and pumiliotoxin B. [2] Other representatives include gephyrotoxin 223 AB and gephyrotoxin. [3]

Phenanthroindolizidine alkaloids

Representatives of this alkaloid group include tylophorine, tylocrebrine and tylophorinidine. [4] [5]

Elaeocarpus alkaloids

Representatives of this group include Elaeocanine A, Elaeocarpine and Elaeocarpidine. [6]

Securinega alkaloids

The main alkaloid in this category is securinine. Others are securinol A and norsecurinine. [7]

Tylophora alkaloids

Most of the Tylophora alkaloids belong to the phenanthroindolizidine alkaloid family, including tylophorine, septicin, and hispidine. [8]

Ipomoea alkaloids

Main alkaloids of this group are Ipalbin and Ipomin. Furthermore, Ipalbidine and Ipohardine occur. [9]

Properties

Swainsonine-type compounds are currently under investigation for their potential as active agents against AIDS. Swainsonine and castanospermine function as inhibitors of sugar-splitting enzymes. Castanospermine also exhibits anti-cancer and anti-HIV properties, [2] while Slaframine acts as a parasympathomimetic agent. Pumiliotoxin A enhances the contraction of striated muscle, and gephyrotoxin has similar effects to pumiliotoxin A. Due to their multifaceted impacts on the nervous system, these alkaloids are in high demand. However, their natural availability through frog skin extraction is severely limited due to species protection measures. [3]

Related Research Articles

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

Toxiferine is a curare toxin. It is a bisindole alkaloid derived from Strychnos toxifera and a nicotinic acetylcholine receptor antagonist. This alkaloid is the main toxic component of Calabash curare, and one of the most toxic plant alkaloids known. The lethal dose (LD50) for mice has been determined as 10 - 60 µg/kg by intravenous administration. It is a muscle relaxant that causes paralysis of skeletal muscle, which takes approximately 2 hours to recovery for a moderate dose, and 8 hours of total paralysis with a 20-fold paralytic dose. The paralysis can be antagonized by neostigmine

<span class="mw-page-title-main">Steroidal alkaloid</span> Class of chemical compounds

Steroidal alkaloids have the basic steroidal skeleton with nitrogen-based functional groups attached to the skeleton. More specifically, they are distinguished by their tetracyclic cyclopentanoperhydrophenanthrene skeleton that marks their close relationship with sterols. They fall in two major categories: Solanum alkaloids and Veratrum alkaloids. A Steroidal alkaloid has also been found in Chonemorpha fragrans, 'chonemorphine' was used to treat intestinal infections in Wistar rats..

<span class="mw-page-title-main">Pyridine alkaloids</span> Class of chemical compounds

Pyridine alkaloids are a class of alkaloids, nitrogen-containing chemical compounds widely found in plants, that contain a pyridine ring. Examples include nicotine and anabasine which are found in plants of the genus Nicotiana including tobacco.

<span class="mw-page-title-main">Piperidine alkaloids</span>

Piperidine alkaloids are naturally occurring chemical compounds from the group of alkaloids, which are chemically derived from piperidine.

<span class="mw-page-title-main">Acridone alkaloids</span>

Acridone alkaloids are natural products derived from acridone.

<span class="mw-page-title-main">Isoquinoline alkaloids</span>

Isoquinoline alkaloids are natural products of the group of alkaloids, which are chemically derived from isoquinoline. They form the largest group among the alkaloids.

<span class="mw-page-title-main">Quinoline alkaloids</span>

Quinoline alkaloids are naturally occurring chemical compounds from the group of alkaloids, which are chemically derived from quinoline. Some quinoline alkaloids show antiseptic, convulsive or antineoplastic effects.

Erythrina alkaloids, generally containing benzyl-tetrahydroisoquinoline structure, are widely distributed in Erythrina species, a genus of plants which belong to the Fabaceae family in tropical and subtropical regions. The Erythrina alkaloids can be found in several organs of Erythrina trees but are primarily found in their seeds. They display several unique properties, and are the subject of active scientific research relating to their synthesis and bioactivity.

<span class="mw-page-title-main">Carbazole alkaloids</span>

The carbazole alkaloids are natural products of the indole alkaloid type, derived from carbazole.

<span class="mw-page-title-main">Conium alkaloids</span>

Conium alkaloids are natural products of the piperidine alkaloid type.

<span class="mw-page-title-main">Benzylisoquinoline alkaloids</span>

The benzylisoquinoline alkaloids are natural products that can be classified as isoquinoline alkaloids and are derived from benzylisoquinoline. They also include the benzyl(tetrahydro)isoquinoline alkaloids.

<span class="mw-page-title-main">Bisbenzylisoquinoline alkaloids</span>

Bisbenzylisoquinoline alkaloids are natural products found primarily in the plant families of the barberry family, the Menispermaceae, the Monimiaceae, and the buttercup family.

<span class="mw-page-title-main">Cephalotaxus alkaloids</span>

Cephalotaxus alkaloids are natural products characterized by pentacyclic structure.

<span class="mw-page-title-main">Imidazole alkaloids</span>

Imidazole alkaloids are a group of alkaloidss whose basic structure contains the imidazole ring system.

<span class="mw-page-title-main">Corydalis Alkaloids</span>

Corydalis Alkaloids are categorized as natural products of the isoquinoline alkaloid type.

<span class="mw-page-title-main">Diterpene alkaloids</span>

Diterpene alkaloids are natural products of the terpene alkaloid type.

<span class="mw-page-title-main">Dendrobium alkaloids</span>

Dendrobium alkaloids are natural products and so-called pseudoalkaloids.

<span class="mw-page-title-main">Pyrrolidine alkaloids</span>

The pyrrolidine alkaloids are natural products chemically derived from pyrrolidine.

<span class="mw-page-title-main">Areca alkaloids</span>

Areca alkaloids are a group of piperidine alkaloids found in the areca nut, the seeds of the areca palm.

Apocynaceae alkaloids are natural products found in the plant family of the dogbane family (Apocynaceae).

References

  1. 1 2 Entry on Indolizidin-Alkaloide . at: Römpp Online . Georg Thieme Verlag, retrieved {{{Datum}}}.
  2. 1 2 3 4 5 H. Latscha, U. Kazmaier (2016), Chemie für Biologen (4 ed.), Berlin Heidelberg: Springer Spektrum, pp. 685f, ISBN   9783662477830
  3. 1 2 3 G. Habermehl, P. Hammann, H. Krebs (2002), Naturstoffchemie (2 ed.), Berlin Heidelberg: Springer-Verlag, pp. 201ff, ISBN   9783540439523 {{citation}}: CS1 maint: multiple names: authors list (link)
  4. Eberhard Breitmaier (1997), Alkaloide, Wiesbaden: Springer Fachmedien, pp. 44f, ISBN   9783519035428
  5. Entry on Phenanthroindolizidin-Alkaloide . at: Römpp Online . Georg Thieme Verlag, retrieved {{{Datum}}}.
  6. Entry on Elaeocarpus-Alkaloide . at: Römpp Online . Georg Thieme Verlag, retrieved {{{Datum}}}.
  7. Entry on Indolizidine alkaloids . at: Römpp Online . Georg Thieme Verlag, retrieved {{{Datum}}}.
  8. Entry on Tylophora-Alkaloide . at: Römpp Online . Georg Thieme Verlag, retrieved {{{Datum}}}.
  9. Entry on Ipomoea-Alkaloide . at: Römpp Online . Georg Thieme Verlag, retrieved {{{Datum}}}.