Penicillenols (A1, A2, B1, B2, C1 and C2)

Trivial name:

Penicillenols

Systematic name:

A1:(2S)-3-hydroxy-2-[(1S)-1-hydroxyethyl]-1-methyl-4-(2-methyloctanoyl)-2H-pyrrol-5-one

A2:(2R)-3-hydroxy-2-[(1R)-1-hydroxyethyl]-1-methyl-4-(2-methyloctanoyl)-2H-pyrrol-5-one

B1:(5Z)-5-ethylidene-4-hydroxy-1-methyl-3-(2-methyloctanoyl)pyrrol-2-one

B2:(5E)-5-ethylidene-4-hydroxy-1-methyl-3-(2-methyloctanoyl)pyrrol-2-one

C1:(2S)-3-hydroxy-2-[(1S)-1-hydroxyethyl]-1-methyl-4-[(E)-2-methyloct-6-enoyl]-2H-pyrrol-5-one

C2:(2R)-3-hydroxy-2-[(1R)-1-hydroxyethyl]-1-methyl-4-[(E)-2-methyloct-6-enoyl]-2H-pyrrol-5-one

Molecular formulae: 

A1: C16H27NO4

A2: C16H27NO4

B1: C16H25NO3

B2:C16H25NO3

C1:C16H25NO4

C2:C16H25NO4

Molecular weight: A1: 297.395 g/mol; A2: 297.395 g/mol; B1:279.38 g/mol; B2:279.38 g/mol; C1:295.379g/mol ;C2:295.379g/mol

Literature reference:

References URL: 

Aspergillus Species known to produce this metabolite:

Toxicity:

Penicillenols (A1, A2, B1, B2, C1 and C2) were isolated from Aspergillus restrictus DFFSCS006, and could differentially inhibit biofilm formation and eradicate pre-developed biofilms of Candida albicans. Their structure – bioactivity relationships suggested that the saturation of hydrocarbon chain at C-8, R-configuration of C-5 and trans-configuration of the double bond between C-5 and C-6 of pyrrolidine-2,4-dione unit were important for their anti-biofilm activities. Penicillenols A2 and B1 slowed the hyphal growth and suppressed the transcripts of hypha specific genes HWP1, ALS1, ALS3, ECE1 and SAP4.
Moreover, penicillenols A2 and B1 were found to act synergistically with amphotericin B against C. albicans biofilm formation.

Structure image:  

Penicillenol

Mycotoxin & Metabolites

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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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