1332. Bongkrekic Acid

Nomenclature

CAS number: 11076-19-0
(2E,4Z,6R,8Z,10E,14E,17S,18E,20Z)-20-(Carboxymethyl)-6-methoxy-2,5,17-trimethyl-2,4,8,10,14,18,20-docosaheptaenedioic acid; 3-carboxymethyl-17-methoxy-6,18,21-trimethyldocosa-2,4,8,12,14,18,20-heptaenedioic acid; BA.
C28H38O7; mol wt 486.60.
C 69.11%, H 7.87%, O 23.02%.

Description and references

One of the two toxic antibiotic principles produced by Pseudomonas cocovenenans on partially defatted coconut; the other being toxoflavin, q.v. Name derived from “bongkrek”, a molded coconut product from Indonesia which becomes highly poisonous when P. cocovenenans outgrows the mold. Isoln: van Veen, Mertens, Rec. Trav. Chim. 53, 257 (1934); 54, 373 (1935); Nugteren, Berends, ibid. 76, 13 (1957). Purification and properties: Lijmbach et al., Tetrahedron 26, 5993 (1970). Structural studies: eidem, ibid. 27, 1839 (1971). Revised structure: De Bruijn et al., ibid. 29, 1541 (1973). Absolute configuration: Zylber et al., Experientia 29, 387, 648 (1973). Influence on carbohydrate metabolism: van Veen, Mertens, Arch. Neerl. Physiol. 21, 73 (1936), C.A. 30, 38809 (1936); inhibition of adenine nucleotide translocation: Henderson, Lardy, J. Biol. Chem. 245, 1319 (1970); Klingenberg et al., Biochem. Biophys. Res. Commun. 39, 363 (1970).

Chemical structure

Properties

White, amorphous solid, mp 50-60°. uv max (methanol): 237, 267 nm (ε 32000, 36700). [α]D25 +162.5°. LD50 i.v. in mice: 1.41 mg/kg (Lijmbach).