My watch list  


IUPAC name (2S)-N-[(S)-[(2S,4R,6R)-6-[(2S)-2,3-dimethoxypropyl]-4-hydroxy-5,5-dimethyl-2-tetrahydropyranyl]-methoxymethyl]-2-hydroxy-2-[(2R,5R,6R)-2-methoxy-5,6-dimethyl-4-methylene-2-tetrahydropyranyl]acetamide
Other names Pederine
CAS number 27973-72-4
PubChem 5381287
SMILES C[C@H]1[C@H](O[C@](CC1=C)([C@@H](C(=O)N[C@H]([C@@H]2C[C@H](C([C@H](O2)C[C@@H](COC)OC)(C)C)O)OC)O)OC)C
Molecular formula C25H45NO9
Molar mass 503.6261
Except where noted otherwise, data are given for
materials in their standard state
(at 25 °C, 100 kPa)

Infobox disclaimer and references

Pederin is a vesicant toxic amide with two tetrahydropyran rings, found in the haemolymph of the Paederus genus of beetles, including the Nairobi fly, belonging to the Staphylinidae family. It was first characterized by processing 25 million field-collected P. fuscipes.[1] It makes up approximately 0.025% of an insects weight (for P. fuscipes).[1]

It has been demonstrated that the production of pederin relies on the activities of an endosymbiont (Pseudomonas ssp.) within Paederus.[2]

The manufacture of pederin is largely confined to adult female beetles - larvae and males only store pederin acquired maternally (i.e., through eggs) or by ingestion.[1]

Mode of Action

Pederin blocks mitosis at levels as low as 1 ng/ml, by inhibiting protein and DNA synthesis without affecting RNA synthesis,[3] prevents cell division, and has been shown to extend the life of mice bearing a variety of tumors.[2] For these reasons, it has garnered interest as a potential anti-cancer treatment.


  1. ^ a b c Bugs Don’t Have to Bite to Do Damage:The Tale of the Paederus Beetle
  2. ^ a b Piel, J. 2002. A polyketide synthase-peptide synthetase gene cluster from an uncultured bacterial symbiont of Paederus beetles. PNAS. 99: 14002-14007.
  3. ^ Frank, J.H. & K. Kanamitsu. 1987. Paederus, Sensu Lato (Coleoptera: Staphylinidae): Natural History and Medical Importance. J. Med. Entomol. 24: 155-191.
This article is licensed under the GNU Free Documentation License. It uses material from the Wikipedia article "Pederin". A list of authors is available in Wikipedia.
Your browser is not current. Microsoft Internet Explorer 6.0 does not support some functions on Chemie.DE