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: C16H27NO4A2: C16H27NO4B1: C16H25NO3B2:C16H25NO3C1:C16H25NO4C2: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: 

Penicillenols from a deep-sea fungus Aspergillus restrictus inhibit Candida albicans biofilm formation and hyphal growth. Wang J, Yao QF, Amin M, Nong XH, Zhang XY, Qi SH. J Antibiot (Tokyo). 2017 Jun;70(6):763-770. doi: 10.1038/ja.2017.45. Epub 2017 Apr 5.

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: 

Aspergillus Species known to produce this metabolite: