Ditryptophenoline

ID 2: 78

Toxin: n

Trivial name:

Chaetocin, 2,​5:2′,​5′-​dide(epidithio)​-​19,​19′-​dideoxy-​19,​19′-​diphenyl-​, (2’β,​5’α,​7’S,​15’β)​-; (-​)​-​Ditryptophenaline; Ditryptophenaline; [10b,​10’b-​Bi-​10bH-​pyrazino[1′,​2′:1,​5]​pyrrolo[2,​3-​b]​indole]​-​1,​1′,​4,​4′-​tetrone, 2,​2′,​3,​3′,​5a,​5’a,​6,​6′,​11,​11′,​11a,​11’a-​dodecahydro-​2,​2′-​dimethyl-​3,​3′-​bis(phenylmethyl)​-​, [3S-​[3α,​5aα,​10bα(3’R*,​5’aR*,​10’bR*,​11’aR*)​,​11aβ]​]​-

Systematic name:

[10b,10’b-Bi-10bH-pyrazino[1′,2′:1,5]pyrrolo[2,3-b]indole]-1,1′,4,4′-tetrone, 2,2′,3,3′,5a,5’a,6,6′,11,11′,11a,11’a-dodecahydro-2,2′-dimethyl-3,3′-bis(phenylmethyl)-, (3S,3’S,5aS,5’aS,10bS,10’bS,11aS,11’aS)-

Molecular formulae: 

C42H40N6O4

Molecular weight: 692.80

Chemical abstract number: 64947-43-9

Literature reference:

  • The structure of ditryptophenaline-​a new metabolite of Aspergillus flavus. Springer, James P.; Buechi, George; Kobbe, Brunhilde; Demain, Arnold L.; Clardy, Jon. Tetrahedron Letters (1977), (28), 2403-6.
    A new diketopiperazine alkaloid from Aspergillus oryzae. Shaaban, Mohamed; Magdy El-Metwally, Mohammad; Nasr, Hamdi. Natural Product Research (2014), 28(2), 86-94

References URL: 

Aspergillus Species known to produce this metabolite:

Structure image:  

ditryptophenolineweb

Date uploaded: 2008-07-07 16:08:30

Mycotoxin & Metabolites

Mycotoxin & Metabolite database

Aspergillus species produce a large number of secondary metabolites, sometimes referred to as extrolites. We attempt to list them all here and we also collect published papers.

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