Pederin

Chembox new
ImageFile=Pederin.pngImageSize=200px
IUPACName= (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
OtherNames=Pederine
Section1= Chembox Identifiers
CASNo=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
Section2= Chembox Properties
Formula=C₂₅H₄₅NO₉
MolarMass=503.6261
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Section3= Chembox Hazards
MainHazards=
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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". [http://www.mdn.ca/health/information/health_promotion/Engraph/BeetleJuice_e.asp Bugs Don’t Have to Bite to Do Da
] ] It makes up approximately 0.025% of an insects weight (for "P. fuscipes").

It has been demonstrated that the production of pederin relies on the activities of an endosymbiont ("Pseudomonas ssp.") within "Paederus". Piel, J. 2002. A polyketide synthase-peptide synthetase gene cluster from an uncultured bacterial symbiont of Paederus beetles. PNAS. 99: 14002-14007. ]

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.

Mode of Action

Pederin blocks mitosis at levels as low as 1 ng/ml, by inhibiting protein and DNA synthesis without affecting RNA synthesis, [ Frank, J.H. & K. Kanamitsu. 1987. Paederus, Sensu Lato (Coleoptera: Staphylinidae): Natural History and Medical Importance. J. Med. Entomol. 24: 155-191. ] prevents cell division, and has been shown to extend the life of mice bearing a variety of tumors. For these reasons, it has garnered interest as a potential anti-cancer treatment.

References