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Djenkolic acid

Djenkolic acid (or sometimes jengkolic acid) is a sulfur-containing non-protein amino acid naturally found in the djenkol beans of the Southeast Asian plant Archidendron jiringa. Its chemical structure is similar to cystine but contains a methylene (single carbon) unit in between the two sulfur atoms. There is about 20 grams of djenkolic acid per kilogram of dry djenkol beans, and it has also been reported in smaller amounts in the seeds of other leguminous plants such as Leucaena esculenta (2.2 g/kg) and Pithecolobium ondulatum (2.8 g/kg).

Toxicity

The toxicity of djenkolic acid in humans arises from its poor solubility under acidic conditions after consumption of the djenkol bean. Urine analysis of patients reveals erythrocytes, epithelial cells, protein, and the needle-like crystals of djenkolic acid. Urolithiasis can also happen, with djenkolic acid as the nucleus. In young children, it has also been reported to produce painful swelling of the genitalia.

Treatment for this toxicity requires hydration to increase urine flow and alkalinization of urine by sodium bicarbonate. Furthermore, this poisoning can be prevented when consuming djenkol beans by boiling them beforehand, since djenkolic acid is removed from the beans.

Discovery and synthesis

Djenkolic acid was first isolated by Van Veen and Hyman in 1933{{cite journal | doi-access = free

Du Vigneaud and Patterson managed to synthesize djenkolic acid by condensation of methylene chloride with 2 moles of L-cysteine in liquid ammonia. Later on, Armstrong and du Vigneaud prepared djenkolic acid by the direct combination of 1 mole of formaldehyde with 2 moles of L-cysteine in a strongly acidic solution.{{cite journal | doi-access = free

References

References

  1. (5 March 2000). "Djenkolic acid". The On-line Medical Dictionary.
  2. 0-85186-863-0. Google Book Search. Retrieved on November 15, 2008.
  3. 0-7817-9307-6. Google Book Search. Retrieved on November 15, 2008.
  4. 0-7817-9307-6. Google Book Search. Retrieved on November 16, 2008.
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alpha-amino-acids sulfur-amino-acids plant-toxins toxic-amino-acids
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