Ustalic acid
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| Preferred IUPAC name
(2E,2′E)-2,2′-(1,3-Dioxolane-4,5-diylidene)bis(phenylacetic acid) | |
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3D model (JSmol)
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| Properties | |
| C19H14O6 | |
| Molar mass | 338.315 g·mol−1 |
| Appearance | White solid |
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
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Ustalic acid is a naturally occurring chemical compound found in the poisonous mushroom Tricholoma ustale.
Occurrence
[edit]The compound was first reported by Japanese researcher Hirokazu Kawagishi and colleagues in 2002, who isolated about 190 milligrams of the chemical from 30.3 kg (67 lb) of fresh mushrooms.[1]
Toxicity
[edit]Ustalic acid is an inhibitor of the sodium-potassium pump (Na+/K+-ATPase), found in the plasma membrane of all animal cells. Physiologically, inhibition of the sodium-potassium pump generally causes diarrhea, as it prevents water reabsorption from the intestines. When force-fed to laboratory mice, ustalic acid causes them to sit still in a crouched position, hesitant to move, and induces tremors and abdominal contractions. Doses of 10 milligrams cause death.[1] Biosynthetically, ustalic acid is thought to originate from oxidative cleavage of the red pigment phlebiarubron.[2]
Synthesis
[edit]A low-yield total synthesis of the dimethyl ester of ustalic acid was reported in 2006, starting from phlebiarubrone. The oxidant used was lead tetraacetate.[2]
Hayakawa and colleagues reported a more efficient synthesis in 2008, using sesamol as a starting point. This procedure requires eight steps, and uses Suzuki–Miyaura coupling and oxidation of a methylene acetal.[3]
See also
[edit]References
[edit]- ^ a b Sano, Y; Sayama, K; Arimoto, Y; Inakuma, T; Kobayashi, K; Koshino, H; Kawagishi, H (2002). "Ustalic acid as a toxin and related compounds from the mushroom Tricholoma ustale". Chemical Communications (13): 1384–5. doi:10.1039/B202607D. PMID 12125567.
- ^ a b Sawayama, Y; Tsujimoto, T; Sugino, K; Nishikawa, T; Isobe, M; Kawagishi, H (2006). "Syntheses of naturally occurring terphenyls and related compounds". Bioscience, Biotechnology, and Biochemistry. 70 (12): 2998–3003. doi:10.1271/bbb.60389. PMID 17151478. S2CID 28576109.
- ^ Hayakawa, Ichiro; Watanabe, Hidekazu; Kigoshi, Hideo (2008). "Synthesis of ustalic acid, an inhibitor of Na+,K+-ATPase" (PDF). Tetrahedron. 64 (25): 5873–7. doi:10.1016/j.tet.2008.04.051. hdl:2241/100720.
