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Herrmann A, Hedman H, Rosen J, Jansson D, Haraldsson B, Hellenäs KE
Analysis of the mushroom nephrotoxin orellanine and its glucosides
Journal of Natural Products 75(10) (2012)
1690-1696
|
b-D-Glcp-(1-4)-Subst
Subst = orellanine = SMILES O=n1ccc(O)c(O)c1c2c(O){4}c(O)ccn2=O |
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Cortinarius rubellus
(NCBI TaxID 86073,
species name lookup)
Taxonomic group: fungi / Basidiomycota
(Phylum: Basidiomycota)
Organ / tissue: fruiting body
NCBI PubMed ID: 23046414Publication DOI: 10.1021/np300135kJournal NLM ID: 7906882Publisher: American Society of Pharmacognosy
Correspondence: andersherrmann
gmail.com
Institutions: National Food Agency, Uppsala, Sweden, Institute of Medicine, University of Gothenburg, Gothenburg, Sweden, Swedish Defence Research Agency, FOI CBRN Defence and Security, Umeå, Sweden
Orellanine is a nephrotoxin found in various Cortinaceae mushroom species. Unintentional consumption after these species were confused with edible mushrooms such as Cantharellus tubaeformis has caused several casualties. In this work, a quantitative HPLC-ESI-MS/MS method for total orellanine in Cortinarius rubellus, spiked blood plasma, and a mushroom stew prepared from C. tubaeformis with the addition of a single specimen of C. rubellus is presented. The existence of mono- and diglucosylated orellanine in C. rubellus was also proven, although quantitative analysis could not be obtained for the glucosides due to rapid hydrolyzation to orellanine in the extract. Extraction with 3 M HCl or water mainly yielded orellanine, while MeOH or acidified MeOH mainly extracted mono- and diglucosylated orellanine. The highest recovery of total orellanine was obtained with 3 M HCl, which was subsequently used for quantitative analysis. A C18 HPLC column and low pH in the eluents retained all these toxins. Orellanine could be detected at a 4.9 ng/mL level in all extracts, which is well below the threshold for acute toxic effects. Additionally, the fragmentation pattern of orellanine upon electrospray MS/MS was probed. The method described is useful for two important applications. First, it allows quantitative analysis of processed food products that may be contaminated by orellanine from Cortinaceae mushrooms. Second, orellanine is currently being evaluated as a potential cure of metastatic renal cancer, and this work provides a method for monitoring orellanine at low concentrations within the therapeutic interval in blood serum
orellanine, orellanine glucosides, nephrotoxin, Cortinaceae
Structure type: monomer ; 415.0986 [M+H]+
C
16H
18N
2O
11Location inside paper: abstract, middle structure
Compound class: glycoside
Contained glycoepitopes: IEDB_142488,IEDB_146664,IEDB_983931,SB_192
Methods: acid hydrolysis, extraction, HPLC-MS, centrifugation, HPLC-TOF-MS, HPLC-QTOF-MS/MS
Related record ID(s): 48117
NCBI Taxonomy refs (TaxIDs): 86073
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Herrmann A, Hedman H, Rosen J, Jansson D, Haraldsson B, Hellenäs KE
Analysis of the mushroom nephrotoxin orellanine and its glucosides
Journal of Natural Products 75(10) (2012)
1690-1696
|
b-D-Glcp-(1-4)-+
|
b-D-Glcp-(1-10)-Subst
Subst = orellanine = SMILES O=n1cc{10}c(O)c(O)c1c2c(O){4}c(O)ccn2=O |
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Cortinarius rubellus
(NCBI TaxID 86073,
species name lookup)
Taxonomic group: fungi / Basidiomycota
(Phylum: Basidiomycota)
Organ / tissue: fruiting body
NCBI PubMed ID: 23046414Publication DOI: 10.1021/np300135kJournal NLM ID: 7906882Publisher: American Society of Pharmacognosy
Correspondence: andersherrmann
gmail.com
Institutions: National Food Agency, Uppsala, Sweden, Institute of Medicine, University of Gothenburg, Gothenburg, Sweden, Swedish Defence Research Agency, FOI CBRN Defence and Security, Umeå, Sweden
Orellanine is a nephrotoxin found in various Cortinaceae mushroom species. Unintentional consumption after these species were confused with edible mushrooms such as Cantharellus tubaeformis has caused several casualties. In this work, a quantitative HPLC-ESI-MS/MS method for total orellanine in Cortinarius rubellus, spiked blood plasma, and a mushroom stew prepared from C. tubaeformis with the addition of a single specimen of C. rubellus is presented. The existence of mono- and diglucosylated orellanine in C. rubellus was also proven, although quantitative analysis could not be obtained for the glucosides due to rapid hydrolyzation to orellanine in the extract. Extraction with 3 M HCl or water mainly yielded orellanine, while MeOH or acidified MeOH mainly extracted mono- and diglucosylated orellanine. The highest recovery of total orellanine was obtained with 3 M HCl, which was subsequently used for quantitative analysis. A C18 HPLC column and low pH in the eluents retained all these toxins. Orellanine could be detected at a 4.9 ng/mL level in all extracts, which is well below the threshold for acute toxic effects. Additionally, the fragmentation pattern of orellanine upon electrospray MS/MS was probed. The method described is useful for two important applications. First, it allows quantitative analysis of processed food products that may be contaminated by orellanine from Cortinaceae mushrooms. Second, orellanine is currently being evaluated as a potential cure of metastatic renal cancer, and this work provides a method for monitoring orellanine at low concentrations within the therapeutic interval in blood serum
orellanine, orellanine glucosides, nephrotoxin, Cortinaceae
Structure type: oligomer ; 577.1516 [M+H]+
C
22H
28N
2O
16Location inside paper: abstract, bottom structure, Fig. 1, structure B
Compound class: glycoside
Contained glycoepitopes: IEDB_142488,IEDB_146664,IEDB_983931,SB_192
Methods: acid hydrolysis, extraction, HPLC-MS, centrifugation, HPLC-TOF-MS, HPLC-QTOF-MS/MS
Related record ID(s): 48116, 48189
NCBI Taxonomy refs (TaxIDs): 86073
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Ahmad R, Lim CK, Marzuki NF, Goh Y-K, Azizan KA, Goh YK, Goh KJ, Ramzi AB, Baharum SN
Metabolic profile of Scytalidium parasiticum-Ganoderma boninense co-cultures revealed the alkaloids, flavonoids and fatty acids that contribute to anti-Ganoderma activity
Molecules 25(24) (2020)
ID 5965
|
b-D-Glcp-(1-7)-Subst
Subst = naringenin = SMILES O=C1CC(C2=CC={54}C(O)C=C2)OC3=C{7}C(O)={6}C{5}C(O)=C13 |
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Ganoderma boninense G10
(Ancestor NCBI TaxID 34458,
species name lookup)
Scytalidium parasiticum AAX0113
(Ancestor NCBI TaxID 5538,
species name lookup)
Taxonomic group: fungi / Basidiomycota, Ascomycota
(Phylum: Basidiomycota, Ascomycota)
NCBI PubMed ID: 33339375Publication DOI: 10.3390/molecules25245965Journal NLM ID: 100964009Publisher: Basel, Switzerland: MDPI
Correspondence: Ahmad R <fida.ahmad
ukm.edu.my>; Azizan KA <kamalrulazlan
ukm.edu.my>; Ramzi AB <bazliramzi
ukm.edu.my>; Lim CK <cklim
twinarrow.com.my>; Marzuki NF <nf91fadh
gmail.com>; Goh Y-K <gohykheng
aarsb.com.my>; Goh YK <gohyk
aarsb.com.my>; Goh KJ <gohkj
aarsb.com.my>; Baharum SN <nataqain
ukm.edu.my>
Institutions: Metabolomics Research Laboratory, Institute of Systems Biology (INBIOSIS), Universiti Kebangsaan Malaysia, UKM, Bangi, Malaysia, Advanced Agriecological Research Sdn Bhd, Petaling Jaya, Malaysia
In solving the issue of basal stem rot diseases caused by Ganoderma, an investigation of Scytalidium parasiticum as a biological control agent that suppresses Ganoderma infection has gained our interest, as it is more environmentally friendly. Recently, the fungal co-cultivation has emerged as a promising method to discover novel antimicrobial metabolites. In this study, an established technique of co-culturing Scytalidium parasiticum and Ganoderma boninense was applied to produce and induce metabolites that have antifungal activity against G. boninense. The crude extract from the co-culture media was applied to a High Performance Liquid Chromatography (HPLC) preparative column to isolate the bioactive compounds, which were tested against G. boninense. The fractions that showed inhibition against G. boninense were sent for a Liquid Chromatography-Time of Flight-Mass Spectrometry (LC-TOF-MS) analysis to further identify the compounds that were responsible for the microbicidal activity. Interestingly, we found that eudistomin I, naringenin 7-O-beta-D-glucoside and penipanoid A, which were present in different abundances in all the active fractions, except in the control, could be the antimicrobial metabolites. In addition, the abundance of fatty acids, such as oleic acid and stearamide in the active fraction, also enhanced the antimicrobial activity. This comprehensive metabolomics study could be used as the basis for isolating biocontrol compounds to be applied in oil palm fields to combat a Ganoderma infection.
metabolomics, Biological control, Ganoderma boninense, LC-TOF-MS analysis, Scytalidium parasiticum, anti-Ganoderma
Structure type: monomer
Location inside paper: Table 3, peak no. 34
Trivial name: prunin
Compound class: glycoside, flavonoid glycoside
Contained glycoepitopes: IEDB_142488,IEDB_146664,IEDB_983931,SB_192
Methods: MS/MS, extraction, RP-HPLC, cell growth, sonication, centrifugation, antifungal activity test, HPLC-TOF-MS
Biological activity: compound has antimicrobial effects against a wide spectrum of bacteria (Gram-positive and -negative) and acts as a single component
Comments, role: molecular mass of [M+CAN+H]+ adduct 476.1605 and molecular formula C22H25N3O7S is wrong; Compound generated by symbiosis of fungal strains Ganoderma boninense G10 and Scytalidium parasiticum AAX0113
Related record ID(s): 48906, 49689
NCBI Taxonomy refs (TaxIDs): 34458,
5538
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