Aristolochic acid
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IUPAC name
8-Methoxy-6-nitrophenanthro[3,4-d][1,3]dioxole-5-carboxylic acid
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| Other names
Aristinic acid; Aristolochia yellow; Aristolochic acid A; Aristolochin;Aristolochine; Descresept; Tardolyt;TR 1736
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3D model (Jmol)
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| ECHA InfoCard | 100.005.673 |
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PubChem CID
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| Properties | |
| C17H11NO7 | |
| Molar mass | 341.28 g·mol−1 |
| Appearance | yellow powder |
| Melting point | 260 to 265 °C (500 to 509 °F; 533 to 538 K) |
| Slightly soluble | |
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Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
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| Infobox references | |
Aristolochic acids (English /əˌrɪstəˈloʊkᵻk/) are a family of carcinogenic, mutagenic, and nephrotoxic commonly found in the birthwort (Aristolochiaceae) family of plants. Aristolochic acid (AA) I is the most abundant one. The Aristolochiaceae family includes the Aristolochia genus and the Asarum (wild ginger) genus, which are commonly used in Chinese herbal medicine. Although these compounds are widely associated with kidney problems and urothelial cancers, the use of AA-containing plants for medicinal purposes has a long history. Nevertheless, the FDA has issued warnings regarding consumption of AA-containing supplements.
Aristolochic acid first appeared in Chinese medicine in the fifth century AD, but the birthwort plants in which it is found are mentioned in ancient Greek and Roman medical texts dating back even earlier. In these ancient times, it was used to treat kidney and urinary problems, as well as gout, snakebites, and a variety of other ailments. It was also considered to be an effective contraceptive. In many of these cases, birthwort plants, and the aristolochic acids they contain, were just some of the many ingredients used to create ointments or salves. In the early first century, in Roman texts, aristolochic acids are first mentioned as a component of frequently ingested medicines to treat things such as asthma, hiccups, spasms, pains, and expulsion of afterbirth.
Aristolochic acid poisoning was first diagnosed at a clinic in Brussels, Belgium, when cases of nephritis leading to rapid kidney failure were seen in a group of women who had all taken the same weight-loss supplement, Aristolochia fangchi, which contained aristolochic acid. This nephritis was termed “Chinese herbs nephropathy” (CHN) due to the origin of the weight-loss supplement. A similar condition previously known as Balkan endemic nephropathy (BEN), first characterized in the 1950s in southeastern Europe, was later discovered to be also the result of aristolochic acid (AA) consumption. BEN is more slowly progressive than the nephritis that is seen in CHN, but is likely caused by low-level AA exposure, possibly from contamination of wheat flour seeds by a plant of the birthwort family, Aristolochia clematitis. CHN and BEN fall under the umbrella of what is now known as aristolochic acid nephropathy, the prevalent symptom of AA poisoning.
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Wikipedia