Fusaproliferin

Fusaproliferin
Names
IUPAC name
[(2S)-2-[(1S,3E,7E,11S,12E,15R)-11,17-dihydroxy-1,4,8,12-tetramethyl-18-oxo-16-bicyclo[13.3.0]octadeca-3,7,12,16-tetraenyl]propyl] acetate
Identifiers
3D model (JSmol)
ChEMBL
ChemSpider
KEGG
  • InChI=1S/C27H40O5/c1-17-8-7-9-18(2)14-15-27(6)22(12-11-19(3)23(29)13-10-17)24(25(30)26(27)31)20(4)16-32-21(5)28/h8,11,14,20,22-23,29-30H,7,9-10,12-13,15-16H2,1-6H3/b17-8+,18-14+,19-11+/t20-,22-,23+,27+/m1/s1
    Key: VRGWBRLULZUWAJ-UEWDWXLZSA-N
  • C/C/1=C\CC/C(=C/C[C@]2([C@H](C/C=C(/[C@H](CC1)O)\C)C(=C(C2=O)O)[C@H](C)COC(=O)C)C)/C
Properties
C27H40O5
Molar mass 444.6 g/mol
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
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Infobox references

Fusaproliferin is a mycotoxin that is naturally produced by the fungi genus Fusarium to protect itself against competing microorganisms. It was first isolated from the Fusarium proliferatum species but can be found in at least 15 species within this genus. It was initially named proliferin, but the name was later changed to fusaproliferin because 'proliferin' was already in use. Fusarium fungi are found in soil and can grow on host plants such as grains, fruits, nuts, and spices. Consuming these products poses a significant health risk to living organisms. Health effects caused by mycotoxins include severe illness, cancer and immune deficiency. Most mycotoxins are chemically stable and can withstand food processing.

The compound was first identified in 1976 in maize, its structure was deduced in 1993 and its absolute conformation determined in 1996.