3,5-Dihydroxy-4-isopropyl-trans-stilbene

3,5-Dihydroxy-4-isopropyl-trans-stilbene
Chemical structure of 3,5-dihydroxy-4-isopropyl-trans-stilbene
Names
IUPAC name
5-(2-Phenylethenyl)-2-propan-2-ylbenzene-1,3-diol
Other names
(E)-3,5-Dihydroxy-4-isopropyl-trans-stilbene
3,5-Dihydroxy-4-isopropylstilbene
Identifiers
Jmol-3D images Image
PubChem 133191
Properties
Molecular formula
C17H18O2
Molar mass 254.32 g·mol−1
Except where noted otherwise, data is given for materials in their standard state (at 25 °C (77 °F), 100 kPa)
Infobox references

3,5-Dihydroxy-4-isopropyl-trans-stilbene is a bacterial stilbenoid produced in Photorhabdus bacterial symbionts of Heterorhabditis nematodes. It is a product of an alternative ketosynthase-directed stibenoids biosynthesis pathway. It is derived from the condensation of two β-ketoacyl thioesters .[1] It is produced by the Photorhabdus luminescens bacterial symbiont species of the entomopathogenic nematode, Heterorhabditis megidis. Experiments with infected larvae of Galleria mellonella, the wax moth, support the hypothesis that the compound has antibiotic properties that help minimize competition from other microorganisms and prevents the putrefaction of the nematode-infected insect cadaver.[2]

Entomopathogenic nematodes emerging from a wax moth cadaver

See also

References

  1. Joyce SA, Brachmann AO, Glazer I, Lango L, Schwär G, Clarke DJ, Bode HB (2008). "Bacterial biosynthesis of a multipotent stilbene". Angew Chem Int Ed Engl 47 (10): 1942–5. doi:10.1002/anie.200705148. PMID 18236486.
  2. Hu, K; Webster, JM (2000). "Antibiotic production in relation to bacterial growth and nematode development in Photorhabdus--Heterorhabditis infected Galleria mellonella larvae". FEMS microbiology letters 189 (2): 219–23. doi:10.1111/j.1574-6968.2000.tb09234.x. PMID 10930742.