Pederin

Pederin
Names
IUPAC name
(2S)-N-[(S)-{(2S,4R,6R)-6-[(2S)-2,3-dimethoxypropyl]-4-hydroxy-5,5-dimethyloxan-2-yl}(methoxy)methyl]-2-hydroxy-2-[(2S,5R,6R)-2-methoxy-5,6-dimethyl-4-methylideneoxan-2-yl]acetamide
Other names
Pederine
Identifiers
3D model (JSmol)
ChEBI
ChemSpider
UNII
  • InChI=1S/C25H45NO9/c1-14-12-25(33-9,35-16(3)15(14)2)21(28)22(29)26-23(32-8)18-11-19(27)24(4,5)20(34-18)10-17(31-7)13-30-6/h15-21,23,27-28H,1,10-13H2,2-9H3,(H,26,29)/t15-,16-,17+,18+,19-,20-,21-,23+,25-/m1/s1 ☒N
    Key: ZNEZZONMADKYTB-VRCUBXEUSA-N ☒N
  • InChI=1/C25H45NO9/c1-14-12-25(33-9,35-16(3)15(14)2)21(28)22(29)26-23(32-8)18-11-19(27)24(4,5)20(34-18)10-17(31-7)13-30-6/h15-21,23,27-28H,1,10-13H2,2-9H3,(H,26,29)/t15-,16-,17+,18+,19-,20-,21-,23+,25-/m1/s1
    Key: ZNEZZONMADKYTB-VRCUBXEUBY
  • 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
Properties
C25H45NO9
Molar mass 503.6261
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
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Pederin is a vesicant toxic amide with two tetrahydropyran rings, found in the haemolymph of the beetle genus Paederus, including the Nairobi fly, belonging to the family Staphylinidae. 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]

  1. ^ a b c Bugs Don’t Have to Bite to Do Damage:The Tale of the Paederus Beetle Archived 2011-06-09 at the Wayback Machine
  2. ^ Piel J (2002). "A polyketide synthase-peptide synthetase gene cluster from an uncultured bacterial symbiont of Paederus beetles". PNAS. 99 (22): 14002–14007. Bibcode:2002PNAS...9914002P. doi:10.1073/pnas.222481399. PMC 137826. PMID 12381784.