Aurantiamine

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).

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

References

  1. ↑ "KNApSAcK Metabolite Information - C00011252". www.knapsackfamily.com.
  2. ↑ Bouhoudan A, Bakkach J, Khaddor M, Mourabit N (2024). "Anticancer Effect of Mycotoxins From Penicillium aurantiogriseum: Exploration of Natural Product Potential". International Journal of Microbiology. 2024: 5553860. doi:10.1155/ijm/5553860. PMC 11637627. PMID 39669001.{{cite journal}}: CS1 maint: article number as page number (link)
  3. ↑ Frisvad JC, Filtenborg O (1989). "Terverticillate penicillia: chemotaxonomy and mycotoxin production". Mycologia. 81 (6): 837–861. doi:10.2307/3760103. JSTOR 3760103.
  4. ↑ Börjesson T, Stöllman U, Schnürer J (1990). "Volatile metabolites and other indicators of Penicillium aurantiogriseum growth on different substrates". Applied and Environmental Microbiology. 56 (12): 3705–3710. doi:10.1128/aem.56.12.3705-3710.1990. PMC 185055. PMID 2128008.
  5. ↑ 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.
  6. ↑ Hayashi Y, Orikasa S, Tanaka K, Kanoh K, Kiso Y (2000). "Total synthesis of anti-microtubule diketopiperazine derivatives: phenylahistin and aurantiamine". The Journal of Organic Chemistry. 65 (24): 8402–8405. doi:10.1021/jo0012905. PMID 11101408.
  7. ↑ 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.
  8. ↑ 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.