Aurantiamine Explained

(−)-Aurantiamine is a blue fluorescence metabolite produced by the fungus Penicillium aurantiogriseum, the most common fungi found in cereals.^[1] (−)-Aurantiamine belongs to a class of naturally occurring 2,5-diketopiperazines featuring a dehydrohistidine residue that exhibit important biological activities, such as anti-cancer or neurotoxic effects.^[2] It is the isopropyl analog of the microtubule binding agent (−)-phenylahistin but is 40 times less active than the latter on P388 cell proliferation.^[3] The total asymmetric synthesis of (−)-aurantiamine has been described.^[4]

Notes and References

1. Terverticillate penicillia: chemotaxonomy and mycotoxin production.. Frisvad JC, Filtenborg O . Mycologia . 1989 . 81 . 6 . 837–861. 10.2307/3760103. 3760103 .
2. 2,5-Diketopiperazines: Synthesis, Reactions, Medicinal Chemistry, and Bioactive Natural Products . Borthwick AD . Chemical Reviews . 2012 . 112 . 7 . 3641–3716 . 10.1021/cr200398y . 22575049.
3. Aurantiamine, a diketopiperazine from two varieties of Penicillium aurantiogriseum . Larsen TO, Frisvad JC, Jensen SR . Phytochemistry . 1992 . 31 . 5 . 1613–1615 . 10.1016/0031-9422(92)83116-G .
4. Total asymmetric synthesis of (–)-Phenylhistine, (–)-Aurantiamine and related compounds. Part I . Couladouros EA, Magos AD . Molecular Diversity . 2005 . 9 . 1–3 . 99–109 . 10.1007/s11030-005-1294-x . 15789557. 9490576 .