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211.13.43.111 (talk) Identification changed from Ascochyta viciae to Acremonium sclerotigenum |
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'''Ascofuranone''' is an [[antibiotic]] produced by various ascomycete fungi including ''[[Acremonium sclerotigenum]]''<ref>{{cite journal|vauthors=Hijikawa Y, Matsuzaki M, Suzuki S, Inaoka DK, Tatsumi R, Kido Y, Kita K|title=Re-identification of the ascofuranone-producing fungus ''Ascochyta viciae'' as ''Acremonium sclerotigenum''|journal=J. Antibiot.|pmid=27804952|doi=10.1038/ja.2016.132}}</ref> 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 [[African trypanosomiasis|sleeping sickness]].<ref>{{cite journal |vauthors=Minagawa N, Yabu Y, Kita K, Nagai K, Ohta N, Meguro K, Sakajo S, Yoshimoto A |title=An antibiotic, ascofuranone, specifically inhibits respiration and in vitro growth of long slender bloodstream forms of Trypanosoma brucei brucei |journal=Mol. Biochem. Parasitol. |volume=84 |issue=2 |pages=271–80 |year=1997 |pmid=9084049 |doi=10.1016/S0166-6851(96)02797-1}}</ref> The compound is effective both in vitro [[cell culture]] and in infections in mice.<ref name="dead mice">{{cite journal |vauthors=Yabu Y, Yoshida A, Suzuki T, Nihei C, Kawai K, Minagawa N, Hosokawa T, Nagai K, Kita K, Ohta N |title=The efficacy of ascofuranone in a consecutive treatment on Trypanosoma brucei brucei in mice |journal=Parasitol. Int. |volume=52 |issue=2 |pages=155–64 |year=2003 |pmid=12798927 |doi=10.1016/S1383-5769(03)00012-6}}</ref> |
'''Ascofuranone''' is an [[antibiotic]] produced by various ascomycete fungi including ''[[Acremonium sclerotigenum]]''<ref>{{cite journal|vauthors=Hijikawa Y, Matsuzaki M, Suzuki S, Inaoka DK, Tatsumi R, Kido Y, Kita K|title=Re-identification of the ascofuranone-producing fungus ''Ascochyta viciae'' as ''Acremonium sclerotigenum''|journal=J. Antibiot.|pmid=27804952|doi=10.1038/ja.2016.132|year=2016}}</ref> 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 [[African trypanosomiasis|sleeping sickness]].<ref>{{cite journal |vauthors=Minagawa N, Yabu Y, Kita K, Nagai K, Ohta N, Meguro K, Sakajo S, Yoshimoto A |title=An antibiotic, ascofuranone, specifically inhibits respiration and in vitro growth of long slender bloodstream forms of Trypanosoma brucei brucei |journal=Mol. Biochem. Parasitol. |volume=84 |issue=2 |pages=271–80 |year=1997 |pmid=9084049 |doi=10.1016/S0166-6851(96)02797-1}}</ref> The compound is effective both in vitro [[cell culture]] and in infections in mice.<ref name="dead mice">{{cite journal |vauthors=Yabu Y, Yoshida A, Suzuki T, Nihei C, Kawai K, Minagawa N, Hosokawa T, Nagai K, Kita K, Ohta N |title=The efficacy of ascofuranone in a consecutive treatment on Trypanosoma brucei brucei in mice |journal=Parasitol. Int. |volume=52 |issue=2 |pages=155–64 |year=2003 |pmid=12798927 |doi=10.1016/S1383-5769(03)00012-6}}</ref> |
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Ascofuranone has also been reported to have anti-tumor activity,<ref>{{cite journal |vauthors=Magae J, Hayasaki J, Matsuda Y, Hotta M, Hosokawa T, Suzuki S, Nagai K, Ando K, Tamura G |title=Antitumor and antimetastatic activity of an antibiotic, ascofuranone, and activation of phagocytes |journal=J. Antibiot. |volume=41 |issue=7 |pages=959–65 |year=1988 |pmid=3417568 |doi=10.7164/antibiotics.41.959}}</ref> and modulate the [[immune system]].<ref>{{cite journal |vauthors=Magae J, Suzuki S, Nagai K, Yamasaki M, Ando K, Tamura G |title=In vitro effects of an antitumor antibiotic, ascofuranone, on the murine immune system |journal=Cancer Res. |volume=46 |issue=3 |pages=1073–8 |year=1986 |pmid=3080231}}</ref> |
Ascofuranone has also been reported to have anti-tumor activity,<ref>{{cite journal |vauthors=Magae J, Hayasaki J, Matsuda Y, Hotta M, Hosokawa T, Suzuki S, Nagai K, Ando K, Tamura G |title=Antitumor and antimetastatic activity of an antibiotic, ascofuranone, and activation of phagocytes |journal=J. Antibiot. |volume=41 |issue=7 |pages=959–65 |year=1988 |pmid=3417568 |doi=10.7164/antibiotics.41.959}}</ref> and modulate the [[immune system]].<ref>{{cite journal |vauthors=Magae J, Suzuki S, Nagai K, Yamasaki M, Ando K, Tamura G |title=In vitro effects of an antitumor antibiotic, ascofuranone, on the murine immune system |journal=Cancer Res. |volume=46 |issue=3 |pages=1073–8 |year=1986 |pmid=3080231}}</ref> |
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Revision as of 08:45, 7 January 2017
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| Names | |
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| 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
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| Other names
Ascofuranon
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| Identifiers | |
3D model (JSmol)
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| ChEMBL | |
| ChemSpider | |
PubChem CID
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CompTox Dashboard (EPA)
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| 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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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
- ^ 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.
- ^ 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.
- ^ 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.
- ^ 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.
- ^ 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.