Effect of chloride ions on anthrasesamone C production in a Sesamum indicum hairy root culture and identification of the precursor for its abiotic formation.
The content of anthrasesamone C (5), a rare chlorine-containing anthraquinone, in a hairy root culture of Sesamum indicum increased with increasing chloride ion concentration in the culture medium and reached a maximum at 100 mM. However, the amount of anthrasesamone C (5) in the extract obtained from the hairy roots was increased by incubating the extract. This result suggests that anthrasesamone C (5) was produced from an unidentified metabolite by an abiotic process. 2,3-Epoxyanthrasesamone B (1), a precursor for the non-enzymatic formation of anthrasesamone C (5), was isolated from S. indicum hairy roots cultured in a chloride-deficient medium. Its structure was elucidated to be 2,3-epoxy-9,10-dihydroxy-2-(4-methylpent-3-en-1-yl)-2,3-dihydroanthracene-1,4-dione by spectroscopic methods.
Department of Applied Biological Science, Faculty of Agriculture, Kagawa University, Kagawa, Japan. furumoto@ag.kagawa-u.ac.jp
Toshio
T
Furumoto
Arata
A
Hoshikuma
D000880:Anthraquinones / Q000737:chemistry* / Q000378:metabolism; D002712:Chlorides / Q000494:pharmacology*; D003470:Culture Media; D004305:Dose-Response Relationship, Drug; D007477:Ions; D015394:Molecular Structure; D010936:Plant Extracts; D018517:Plant Roots / Q000166:cytology*; D031685:Sesamum / Q000166:cytology / Q000378:metabolism*
D000880:Anthraquinones; D002712:Chlorides; D003470:Culture Media; D007477:Ions; D010936:Plant Extracts; C573949:anthrasesamone C