Aurantiamine

(−)-Aurantiamine is a blue fluorescence metabolite produced by the fungus Penicillium aurantiogriseum, the most common fungi found in cereals.[2] (−)-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.[3] It is the isopropyl analog of the microtubule binding agent (−)-phenylahistin but is 40 times less active than the latter on P388 cell proliferation.[4] The total asymmetric synthesis of (−)-aurantiamine has been described.[5]

Aurantiamine
Names
Preferred IUPAC name
(3Z,6S)-3-{[5-(2-Methylbut-3-en-2-yl)-1H-imidazol-4-yl]methylidene}-6-(propan-2-yl)piperazine-2,5-dione
Identifiers
3D model (JSmol)
ChEMBL
ChemSpider
  • InChI=1S/C16H22N4O2/c1-6-16(4,5)13-10(17-8-18-13)7-11-14(21)20-12(9(2)3)15(22)19-11/h6-9,12H,1H2,2-5H3,(H,17,18)(H,19,22)(H,20,21)/b11-7-/t12-/m0/s1
    Key: RSGRSUVVCYUKLM-RDQDRAATSA-N
  • InChI=1/C16H22N4O2/c1-6-16(4,5)13-10(17-8-18-13)7-11-14(21)20-12(9(2)3)15(22)19-11/h6-9,12H,1H2,2-5H3,(H,17,18)(H,19,22)(H,20,21)/b11-7-/t12-/m0/s1
    Key: RSGRSUVVCYUKLM-RDQDRAATBK
  • CC(C)[C@H]1C(=O)N/C(=C\C2=C(NC=N2)C(C)(C)C=C)/C(=O)N1
Properties
C16H22N4O2
Molar mass 302.378 g·mol−1
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
Infobox references

References
  1. "KNApSAcK Metabolite Information - C00011252". www.knapsackfamily.com.
  2. Frisvad JC, Filtenborg O (1989). "Terverticillate penicillia: chemotaxonomy and mycotoxin production". Mycologia. 81 (6): 837–861. doi:10.2307/3760103. JSTOR 3760103.
  3. Borthwick AD (2012). "2,5-Diketopiperazines: Synthesis, Reactions, Medicinal Chemistry, and Bioactive Natural Products". Chemical Reviews. 112 (7): 3641–3716. doi:10.1021/cr200398y. PMID 22575049.
  4. Larsen TO, Frisvad JC, Jensen SR (1992). "Aurantiamine, a diketopiperazine from two varieties of Penicillium aurantiogriseum". Phytochemistry. 31 (5): 1613–1615. doi:10.1016/0031-9422(92)83116-G.
  5. Couladouros EA, Magos AD (2005). "Total asymmetric synthesis of (–)-Phenylhistine, (–)-Aurantiamine and related compounds. Part I". Molecular Diversity. 9 (1–3): 99–109. doi:10.1007/s11030-005-1294-x. PMID 15789557. S2CID 9490576.
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