Asparagusic acid

• Published in: Phytochemistry (Oxford) Vol. 97; pp. 5 - 10
• Main Authors: Mitchell, Stephen C., Waring, Rosemary H.
• Format: Journal Article
• Language: English
• Published: England Elsevier Ltd 01.01.2014
• Subjects: 1,2-Dithiolane-4-carboxylic acid; Asparagaceae family; Asparagus; Asparagus officinalis L; Asparagus Plant - chemistry; Asparagusic acid; Humans; Male; Molecular Structure; Short review; Sulphur heterocycle; Thiophenes - chemistry; Thiophenes - isolation & purification; Thiophenes - pharmacology; Urine - chemistry; Urine odour; Sulphur heterocycle; Asparagaceae family; Asparagusic acid; Asparagus; Asparagus officinalis L; Urine odour; 1,2-Dithiolane-4-carboxylic acid; Short review
• ISSN: 0031-9422; 1873-3700
• DOI: 10.1016/j.phytochem.2013.09.014

•Asparagusic acid (1,2-dithiolane-4-carboxylic acid) is unique to asparagus.•The physicochemical properties of the 1,2-dithiolane ring structure are detailed.•Two adjacent sulphur atoms within the ring lead to an enhanced chemical reactivity.•The compound is responsible for the odorous urine excreted after eating asparagus. Asparagusic acid (1,2-dithiolane-4-carboxylic acid) is a simple sulphur-containing 5-membered heterocyclic compound that appears unique to asparagus, though other dithiolane derivatives have been identified in non-food species. This molecule, apparently innocuous toxicologically to man, is the most probable culprit responsible for the curious excretion of odorous urine following asparagus ingestion. The presence of the two adjacent sulphur atoms leads to an enhanced chemical reactivity, endowing it with biological properties including the ability to substitute potentially for α-lipoic acid in α-keto-acid oxidation systems. This brief review collects the scattered data available in the literature concerning asparagusic acid and highlights its properties, intermediary metabolism and exploratory applications.