Ascofuranone

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Ascofuranone
Structural formula of ascofuranone
Space-filling model of the ascofuranone molecule
Names
IUPAC name
5-chloro-3-[(2E,6E)-7-[(2S)-5,5-dimethyl-4-oxo-tetrahydrofuran-2-yl]-3-methyl-octa-2,6-dienyl]-2,4-dihydroxy-6-methyl-benzaldehyde
Other names
Ascofuranon
Identifiers
3D model (Jmol)
ChemSpider
Properties
C23H29ClO5
Molar mass 420.93 g·mol−1
Density 1.207 g/mL
Boiling point 581.2 °C (1,078.2 °F; 854.4 K)
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

Ascofuranone is an antibiotic produced by various ascomycete fungi including Acremonium sclerotigenum[1] that inhibits the Trypanosoma brucei alternative oxidase and is a lead compound in efforts to produce other drugs targeting this enzyme for the treatment of sleeping sickness.[2] The compound is effective both in vitro cell culture and in infections in mice.[3]

Ascofuranone has also been reported to have anti-tumor activity,[4] and modulate the immune system.[5]

References[edit]

  1. ^ Hijikawa Y, Matsuzaki M, Suzuki S, Inaoka DK, Tatsumi R, Kido Y, Kita K (2016). "Re-identification of the ascofuranone-producing fungus Ascochyta viciae as Acremonium sclerotigenum". J. Antibiot. doi:10.1038/ja.2016.132. PMID 27804952. 
  2. ^ Minagawa N, Yabu Y, Kita K, Nagai K, Ohta N, Meguro K, Sakajo S, Yoshimoto A (1997). "An antibiotic, ascofuranone, specifically inhibits respiration and in vitro growth of long slender bloodstream forms of Trypanosoma brucei brucei". Mol. Biochem. Parasitol. 84 (2): 271–80. doi:10.1016/S0166-6851(96)02797-1. PMID 9084049. 
  3. ^ Yabu Y, Yoshida A, Suzuki T, Nihei C, Kawai K, Minagawa N, Hosokawa T, Nagai K, Kita K, Ohta N (2003). "The efficacy of ascofuranone in a consecutive treatment on Trypanosoma brucei brucei in mice". Parasitol. Int. 52 (2): 155–64. doi:10.1016/S1383-5769(03)00012-6. PMID 12798927. 
  4. ^ Magae J, Hayasaki J, Matsuda Y, Hotta M, Hosokawa T, Suzuki S, Nagai K, Ando K, Tamura G (1988). "Antitumor and antimetastatic activity of an antibiotic, ascofuranone, and activation of phagocytes". J. Antibiot. 41 (7): 959–65. doi:10.7164/antibiotics.41.959. PMID 3417568. 
  5. ^ Magae J, Suzuki S, Nagai K, Yamasaki M, Ando K, Tamura G (1986). "In vitro effects of an antitumor antibiotic, ascofuranone, on the murine immune system". Cancer Res. 46 (3): 1073–8. PMID 3080231.