ascofuranone

{{cs1 config|name-list-style=vanc}}

{{chembox

| Verifiedfields = changed

| Watchedfields = changed

| verifiedrevid = 457819837

| Name = Ascofuranone

| ImageFile = Ascofuranone structure.png

| ImageSize = 240

| ImageAlt = Structural formula of ascofuranone

| ImageFile1 = Ascofuranone 3D ball.png

| ImageSize1 = 250

| ImageAlt1 = Space-filling model of the ascofuranone molecule

| PIN = 3-Chloro-5-{(2E,6E)-7-[(2S)-5,5-dimethyl-4-oxooxolan-2-yl]-3-methylocta-2,6-dien-1-yl}-4,6-dihydroxy-2-methylbenzaldehyde

| OtherNames = Ascofuranon

|Section1={{Chembox Identifiers

| SMILES = O=Cc1c(O)c(c(O)c(Cl)c1C)C/C=C(/CC/C=C(\C)[C@H]2OC(C(=O)C2)(C)C)C

| ChemSpiderID_Ref = {{chemspidercite|correct|chemspider}}

| ChemSpiderID = 4939184

| ChEBI = 156148

| ChEMBL_Ref = {{ebicite|correct|EBI}}

| ChEMBL = 133046

| PubChem = 6434242

| InChI = 1/C23H29ClO5/c1-13(7-6-8-14(2)18-11-19(26)23(4,5)29-18)9-10-16-21(27)17(12-25)15(3)20(24)22(16)28/h8-9,12,18,27-28H,6-7,10-11H2,1-5H3/b13-9+,14-8+/t18-/m0/s1

| InChIKey = VGYPZLGWVQQOST-JUERRSSIBJ

| StdInChI_Ref = {{stdinchicite|correct|chemspider}}

| StdInChI = 1S/C23H29ClO5/c1-13(7-6-8-14(2)18-11-19(26)23(4,5)29-18)9-10-16-21(27)17(12-25)15(3)20(24)22(16)28/h8-9,12,18,27-28H,6-7,10-11H2,1-5H3/b13-9+,14-8+/t18-/m0/s1

| StdInChIKey_Ref = {{stdinchicite|correct|chemspider}}

| StdInChIKey = VGYPZLGWVQQOST-JUERRSSISA-N

| CASNo_Ref = {{cascite|correct|CAS}}

| CASNo =38462-04-3

| UNII_Ref = {{fdacite|correct|FDA}}

| UNII = I31EFB9515

}}

|Section2={{Chembox Properties

| C=23 | H=29 | Cl=1 | O=5

| MeltingPt =

| Density = 1.207 g/mL

| BoilingPtC = 581.2

}}

}}

Ascofuranone is an antibiotic produced by various ascomycete fungi including Acremonium sclerotigenum{{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 = The Journal of Antibiotics | volume = 70 | issue = 3 | pages = 304–307 | date = March 2017 | pmid = 27804952 | doi = 10.1038/ja.2016.132 | s2cid = 11725030 | doi-access = free }} 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.{{cite journal | vauthors = Minagawa N, Yabu Y, Kita K, Nagai K, Ohta N, Meguro K, Sakajo S, Yoshimoto A | display-authors = 6 | title = An antibiotic, ascofuranone, specifically inhibits respiration and in vitro growth of long slender bloodstream forms of Trypanosoma brucei brucei | journal = Molecular and Biochemical Parasitology | volume = 84 | issue = 2 | pages = 271–280 | date = February 1997 | pmid = 9084049 | doi = 10.1016/S0166-6851(96)02797-1 }} The compound is effective both in vitro cell culture and in infections in mice.{{cite journal | vauthors = Yabu Y, Yoshida A, Suzuki T, Nihei C, Kawai K, Minagawa N, Hosokawa T, Nagai K, Kita K, Ohta N | display-authors = 6 | title = The efficacy of ascofuranone in a consecutive treatment on Trypanosoma brucei brucei in mice | journal = Parasitology International | volume = 52 | issue = 2 | pages = 155–164 | date = June 2003 | pmid = 12798927 | doi = 10.1016/S1383-5769(03)00012-6 }}

Ascofuranone has also been reported to have anti-tumor activity,{{cite journal | vauthors = Magae J, Hayasaki J, Matsuda Y, Hotta M, Hosokawa T, Suzuki S, Nagai K, Ando K, Tamura G | display-authors = 6 | title = Antitumor and antimetastatic activity of an antibiotic, ascofuranone, and activation of phagocytes | journal = The Journal of Antibiotics | volume = 41 | issue = 7 | pages = 959–965 | date = July 1988 | pmid = 3417568 | doi = 10.7164/antibiotics.41.959 | doi-access = free }} and modulate the immune system.{{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 Research | volume = 46 | issue = 3 | pages = 1073–1078 | date = March 1986 | pmid = 3080231 }}

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