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

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3,5-Dihydroxy-4-isopropyl-trans-stilbene
Chemical structure of 3,5-dihydroxy-4-isopropyl-trans-stilbene
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
PubChem 133191
Jmol-3D images Image 1
Properties
Molecular formula C17H18O2
Molar mass 254.32 g mol−1
Except where noted otherwise, data are 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

  • Pinosylvin, a molecule produced in pines that does not bear the isopropyl acetylation.

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. 
Aglycones
Dihydroxylated
Trihydroxylated
Tetrahydroxylated
O-methylated
  • 4-Methoxyresveratrol
  • Gnetucleistol D (2-methoxyoxyresveratrol)
  • Gnetucleistol E (3-methoxy-isorhapontigenin)
  • Isorhapontigenin (3,4',5-trihydroxy-3'-methoxystilbene)
  • Pterostilbene
  • Rhapontigenin (3,3',5-trihydroxy-4'-methoxystilbene)
Combretastatins:
carboxylated
other acetylations
Glycosides
  • Astringin (Piceatannol 3-O-glucoside)
  • Foeniculoside I, II, III and IV
  • Isorhapontin (Isorhapontigenin glucoside)
  • Mulberroside A (Oxyresveratrol diglucoside)
of resveratrol
of rhapontigenin
  • Rhapontigenin 3-O-rutinoside
    • 4'-Methoxy-(E)-resveratrol 3-O-rutinoside
  • Rhaponticin (Rhapontigenin glucoside)
Oligomeric forms
  • Ampelopsin C, E and H
  • Amurensin A, B, G and H
  • Balanocarpol
  • Carasinol B
  • Dibalanocarpol
  • Diptoindonesin C
  • Diptoindonesin F
  • Flexuosol A
  • Gnetin H
  • Hemsleyanol D
  • Isohopeaphenol
  • Kobophenol A
  • Laetevirenol A, B, C, D and E
  • Malibatol A and B
  • Suffruticosol A and B
  • Vaticanol C
  • Viniferal
  • E-ω-viniferin
  • Z-ω-viniferin
Tetramers:
  • Laetevirenol F and G
of resveratrol
Dimers
Trimers
Tetramers
  • Amurensin E
  • F and K
  • Gnetuhainin R (isorhapontigenin tetramer)
  • Hopeaphenol
  • Vaticanol B
  • Vitisin A
  • B and C
  • β-viniferin (cyclic resveratrol tetramer)
Pentamers
  • Amurensin E and F
Higher polymers
  • γ-viniferin
Oligomeric forms
glycosides or conjugates
  • Diptoindonesin A
  • Laevifonol (an ε-viniferin-ascorbic acid hybrid compound)
  • Laevifoside (O-glucoside of ampelopsin A)
Synthetic
  • Stilbenoid drugs


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