Paederus fuscipes

Pederin (147) has been considered to be derived via polyketide biosynthesis, based on the result of feeding experiments with [ l- " C]acetate and [2- C]acetate in Paederus fuscipes (483). 

Pederin (735) is one of the most potent poisons known to man, with an LDso for rats of ca. 2 p.g per 100 g body weight. The pyran, which causes severe blistering of the skin, is part of the defence system of the beetle Paederus fuscipes. It inhibits chromosome division by first blocking protein synthesis and subsequently halting DNA synthesis. 

Piel, J., Hofer, I., Hui, D. Evidence for a symbiosis island involved in horizontal acquisition of pederin biosynthetic capabilities by the bacterial symbiont of Paederus fuscipes beetles. J. Bacterial. 2004, 186, 1280-1286. 

Benzoylpedamide (140), representing the right half of (+ )-pederin (654), a potent insect poison isolated from Paederus fuscipes, is synthesized from 590 as shown in Scheme 95 [149]. Once again, the initial reaction in the sequence is the addition of an ester enolate to 590, which produces 646 as a mixture of isomers. Conversion of 646 to -lactone 647, protection of the hydroxyl with an EE group, and treatment with er -butyl acetate enolate gives hemiacetal 648. 

Pederamide (12) is an important intermediate in the projected total synthesis of pederin (13), a component of the vesicant of the beetle Paederus fuscipes. /rart5-2-Butene epoxide has been converted (in 16 steps) into pederamide. One of these involved the conversion of the tetrahydrofuran (14) into the pyran-2-one (15) in 96% yield.Synthetic studies on lasalocid A (16) have continued with the use of carbohydrates as substrates for the construction of both furanoid and pyranoid rings of the antibiotic. ... 

C25H45NO9, Mr 503.63, mp. 113 C, LD50 (mouse i. v.) 2 ig/kg. Highly toxic amide from the hemolymph of the blister beetle Paederus fuscipes and related species. Contact with P. leads to severe skin diseases. P. and related compounds such as pederone (4 -Oxo-P.) inhibit the biosynthesis of proteins and mitosis and also have cytostatic activity. Similar compounds have been isolated from marine sponges ( mycalamides, onna-mides). ... 

Pederin (167) is a potent insect poison that is isolated from the East African beetle Paederus fuscipes. It is also a powerful inhibitor of the biosynthesis of proteins and of the mitosis of cells. The toxin has now been synthesized by... 

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