The real nature of the indole alkaloids in Cortinarius infractus: evaluation of artifact formation through solvent extraction method development.
This study was triggered by the absence of infractine in EtOH extracts of Cortinarius infractus and the presence of the beta-carboline-1-propionic acid [I. Brondz, K. Høiland, D.S. Bell, A.R. Annino, TheReporter, Supelco 24 (3) (2006) 6]. In previous studies it was determined that C. infractus contained indole alkaloid substances of the infractine group [W. Steglich, L. Kopanski, M. Wolf, M. Moser, G. Tegtmeyer, Indolalkaloide aus dem Blaetterpilz Cortinarius infractus (Agaricales). Tetrahedron Lett. 25 (1984) 2341]. It is quite possible that some of these compounds do not exist in any other mushroom species and therefore they could prove to be valuable chemotaxonomic markers. Proper classification of this species requires that the chemical markers are identified correctly. In this study, the presence of several compounds previously found in C. infractus (Pers.: Fr.) Fr. is questioned. In this investigation, it was shown by HPLC-MS that infractine and 6-hydroxyinfractine, previously described as constituents of C. infractus, were artifacts produced during the extraction process. Also, the molecular species that participate in the artefact formation were identified. Infractine and 6-hydroxyinfractine, reported earlier in C. infractus, originate from the precursor (pre-infractine) beta-carboline-1-propionic acid during extraction with methanol.
Brondz
Ilia
I
Norwegian University of Life Sciences, Department of Chemistry, Biotechnology and Food Science, P.O. Box 5003, N-1432 As, Norway. ilia.brondz@umb.no
Ekeberg
Dag
D
Høiland
Klaus
K
Bell
David S
DS
Annino
Amy R
AR
D000363:Agaricales / Q000737:chemistry*; D016477:Artifacts; D002243:Carbolines / Q000737:chemistry; D002851:Chromatography, High Pressure Liquid; D026121:Indole Alkaloids / Q000032:analysis / Q000737:chemistry* / Q000302:isolation & purification; D000432:Methanol / Q000737:chemistry; D008962:Models, Theoretical; D015394:Molecular Structure; D011422:Propionates / Q000737:chemistry; D012997:Solvents / Q000737:chemistry*; D053719:Tandem Mass Spectrometry
D002243:Carbolines; D026121:Indole Alkaloids; D011422:Propionates; D012997:Solvents; C029658:propionic acid; D000432:Methanol