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Chemical Compound Review

Lenticin     (2R)-3-(1H-indol-3-yl)-2- trimethylammonio...

Synonyms: Hypaforin, Hypaphorine, CHEMBL503867, AG-J-52845, AC1L4NPJ, ...
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High impact information on [(1R)-1-carboxy-2-(1H-indol-3-yl)ethyl]-trimethyl-ammonium

  • The latter view was supported by restoration of the actin cytoskeleton in hypaphorine-treated root hairs by IAA application [1].
  • The hypaphorine-induced aggregations in the actin and microtubule cytoskeletons could stabilise the structure of cytoskeletal elements, which in turn could hinder the vesicle delivery at the tip necessary for elongation [1].
  • In the hypaphorine-treated hairs the total number of actin filament bundles along most of the root hair length was significantly reduced, presumably due to aggregation of pre-existing actin filaments [1].
  • In addition, we show that hypaphorine counteracts the rapid upregulation by indole-3-acetic acid and 1-naphthalenic-acetic acid of the primary auxin-responsive gene IAA1 and induces a rapid, transient membrane depolarization in root hairs and suspension cells, due to the modulation of anion and K+ currents [2].
  • The indolic compound hypaphorine produced by ectomycorrhizal fungus interferes with auxin action and evokes early responses in nonhost Arabidopsis thaliana [2].

Biological context of [(1R)-1-carboxy-2-(1H-indol-3-yl)ethyl]-trimethyl-ammonium

  • These data suggest that IAA and hypaphorine interact during the very early steps of the IAA perception or signal transduction pathway [3].
  • The mode of inhibition of the IAA-dependent O2*--generating reaction by hypaphorine was analyzed with a double-reciprocal plot and determined to be competitive inhibition, indicating that hypaphorine competes with IAA by binding to the putative IAA binding site on HRP-C [4].
  • Since hypaphorine is structurally similar to IAA, the effects of hypaphorine against IAA may be due to competitive binding to the IAA-binding domain on HRP [5].

Associations of [(1R)-1-carboxy-2-(1H-indol-3-yl)ethyl]-trimethyl-ammonium with other chemical compounds

  • Furthermore, while seedling treatment with 1-amincocyclopropane-1-carboxylic acid (ACC), the precursor of ethylene, results in formation of a hypocotyl apical hook, hypaphorine application as well as root colonization by Pisolithus tinctorius, a hypaphorine-accumulating ectomycorrhizal fungus, stimulated hook opening [3].
  • From the roots of Glycyrrhiza yunnanensis, collected in Yunnan, China, six new oleanane-type triterpene glycosides named yunganosides A1, B1, C1, D1, E2 and F2 were isolated together with hypaphorine [6].

Gene context of [(1R)-1-carboxy-2-(1H-indol-3-yl)ethyl]-trimethyl-ammonium


Analytical, diagnostic and therapeutic context of [(1R)-1-carboxy-2-(1H-indol-3-yl)ethyl]-trimethyl-ammonium


  1. Hypaphorine, an indole-3-acetic acid antagonist delivered by the ectomycorrhizal fungus Pisolithus tinctorius, induces reorganisation of actin and the microtubule cytoskeleton in Eucalyptus globulus ssp bicostata root hairs. Ditengou, F.A., Raudaskoski, M., Lapeyrie, F. Planta (2003) [Pubmed]
  2. The indolic compound hypaphorine produced by ectomycorrhizal fungus interferes with auxin action and evokes early responses in nonhost Arabidopsis thaliana. Reboutier, D., Bianchi, M., Brault, M., Roux, C., Dauphin, A., Rona, J.P., Legué, V., Lapeyrie, F., Bouteau, F. Mol. Plant Microbe Interact. (2002) [Pubmed]
  3. Hypaphorine from the ectomycorrhizal fungus Pisolithus tinctorius counteracts activities of indole-3-acetic acid and ethylene but not synthetic auxins in eucalypt seedlings. Ditengou, F.A., Lapeyrie, F. Mol. Plant Microbe Interact. (2000) [Pubmed]
  4. Fungal auxin antagonist hypaphorine competitively inhibits indole-3-acetic acid-dependent superoxide generation by horseradish peroxidase. Kawano, T., Kawano, N., Hosoya, H., Lapeyrie, F. Biochem. Biophys. Res. Commun. (2001) [Pubmed]
  5. Possible use of indole-3-acetic acid and its antagonist tryptophan betaine in controlled killing of horseradish peroxidase-labeled human cells. Kawano, T. Med. Hypotheses (2003) [Pubmed]
  6. Oleanane glycosides from Glycyrrhiza yunnanensis roots. Ohtani, K., Ogawa, K., Kasai, R., Yang, C.R., Yamasaki, K., Zhou, J., Tanaka, O. Phytochemistry (1992) [Pubmed]
  7. Actin organization during eucalyptus root hair development and its response to fungal hypaphorine. Dauphin, A., De Ruijter, N.C., Emons, A.M., Legué, V. Plant biology (Stuttgart, Germany) (2006) [Pubmed]
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