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Ptaquiloside

HCID 13962857
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Grundinformationen

CAS
87625-62-5
Standard-SMILES
CC1=C[C@]2(O[C@@H]3O[C@H](CO)[C@@H](O)[C@H](O)[C@H]3O)C[C@@H](C)C(=O)[C@@H]2[C@](C)(O)C12CC2
InChIKey
GPHSJPVUEZFIDE-YVPLJZHISA-N
Summenformel
C20H30O8
Durchschnittliche Molmasse
398,4 g/mol
Monoisotopische Masse
398,19406791

Überblick

ptaquiloside has been reported in Pteridium caudatum, Pteris cretica, and other organisms with data available.

Namen und Bezeichner

Bevorzugter Name
Ptaquiloside
IUPAC
(2R,3aR,7S,7aR)-7-hydroxy-2,5,7-trimethyl-3a-[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxyspiro[3,7a-dihydro-2H-indene-6,1'-cyclopropane]-1-one
Englischer Name
ptaquiloside
Summenformel
C20H30O8
Molmasse
398.45

Namen und Synonyme

PTAQUILOSIDE87625-62-5Braxin CDTXSID20892005F0MN9S5699(2R,3aR,7S,7aR)-7-hydroxy-2,5,7-trimethyl-3a-[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxyspiro[3,7a-dihydro-2H-indene-6,1'-cyclopropane]-1-one(2R,3aR,7S,7aR)-7-hydroxy-2,5,7-trimethyl-3a-((2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl)oxyspiro(3,7a-dihydro-2H-indene-6,1'-cyclopropane)-1-oneSpiro(cyclopropane-1,5'-(5H)inden)-3'(2'H)-one, 7'a-(beta-D-glucopyranosyloxy)-1',3'a,4',7'a-tetrahydro-4'-hydroxy-2',4',6'-trimethyl-RefChem:870295DTXCID801035935C20H30O8UNII-F0MN9S5699
Weitere Namen anzeigen
Ptaquiloside,HPLC≥98%ptaquiloside USP/EP/BPPtaquiloside DISCONTINUED(2'R)-7'aβ-(β-D-Glucopyranosyloxy)-1',3'aβ,4',7'a-tetrahydro-4'α-hydroxy-2'β,4',6'-trimethylspiro[cyclopropane-1,5'-[5H]inden]-3'(2'H)-oneSpiro[cyclopropane-1,5'-[5H]inden]-3'(2'H)-one, 7'a-(β-D-glucopyranosyloxy)-1',3'a,4',7'a-tetrahydro-4'-hydroxy-2',4',6'-trimethyl-, (2'R,3'aR,4'S,7'aR)-

Eigenschaften

Berechnete Struktureigenschaften

XLogP
-1,3
Polarare Oberfläche (TPSA)
137 Ų
H-Brücken-Donoren
5
H-Brücken-Akzeptoren
8
Frei drehbare Bindungen
3
Schwere Atome
28
Formalladung
0
Komplexität
702

Experimentelle und physikochemische Eigenschaften

SpringerMaterials PropertiesChemical shift

Physikochemische Eigenschaften

Schmelzpunkt
85 · 85-89 °C(Solv: hexane (110-54-3); acetone (67-64-1))
Siedepunkt
620.7 · 620.7±55.0 °C(Predicted)
Dichte
1.43 · 1.43±0.1 g/cm3(Predicted)
pka
12.85 · 12.85±0.70(Predicted)
Aggregatzustand
Solid
Farbe
White to off-white

Sicherheit und Regulatorisches

Sicherheitsangaben dienen nur zur Orientierung und ersetzen weder das Sicherheitsdatenblatt (SDB) des Lieferanten noch geltende Vorschriften oder eine fachliche Bewertung.

Toxikologische Informationen

Milk Concentrations · 1 Eintrag

Ptaquiloside, 1, a norsesquiterpenoid glucoside, is the major carcinogen of bracken detected in the food chain, particularly in the milk from farm animals. Ptaquiloside has been shown in the milk of cows feeding on a diet containing bracken fern.

Toxicity Summary · 3 Einträge

Bracken fern (Pteridium sp.) is a plant with invasive potential, and ingestion can cause chronic illness and cancers in farm animals. Bracken is a suspected human carcinogen, and exposures can result from ingestion of bracken-contaminated water, dairy products, or meat derived from livestock grazing on bracken fern. Bracken is also consumed in the diets of some communities. Ptaquiloside (PTQ) is a known bracken carcinogen. It is an illudane-type glycoside that forms a highly reactive electrophile, PTQ dienone, known to produce N7-guanine and N3-adenine adducts in DNA.

Bracken fern is a highly problematic plant worldwide due to its toxicity in combination with invasive properties on former farmland, in deforested areas and on disturbed natural habitats. The carcinogenic potential of bracken ferns has been of concern for several decades. Its genotoxic effects are linked to illudane-type glycosides (ITGs), their aglycons and derivatives. Ptaquiloside is considered the dominating ITG, but with significant contributions from other ITGs. The ITG content in bracken fern exhibits substantial spatial, temporal, and chemotaxonomic variation. Consumption of bracken fern as food is linked to human gastric cancer but it also causes urinary bladder cancers in bovines browsing on bracken. Genotoxic metabolites are found in milk and meat from bracken fed animals. ITG exposure may also take place via contaminated water with recent data pointing to concentrations at microgram/L-level following rain events. Airborne ITG-exposure from spores and dust has also been documented.

This study was conducted to determine the optimal boiling time to reduce ptaquiloside (PTA) and to carry out a risk assessment for PTA, a representative toxic substance found in bracken fern (BF; Pteridium aquilinum), which is frequently consumed as food in East Asian countries. High-performance liquid chromatography showed that the concentration of PTA in BF was reduced by up to 99% after boiling for 20 minutes. Risk assessment results showed that the cancer margin of exposure (MOE; greater than or equal to 25,000 = safe) to PTA for an average daily exposure scenario after boiling BF for 20 min was considered safe. In addition, the non-cancer MOE (≥ 300 = safe) to PTA under an average daily exposure scenario after BF boiling for 20 min was considered safe.

Chemie und Industrie

Pharmakologische Informationen

MeSH Pharmacological Classification · 2 Einträge

Substances that increase the risk of NEOPLASMS in humans or animals. Both genotoxic chemicals, which affect DNA directly, and nongenotoxic chemicals, which induce neoplasms by other mechanism, are included.

Chemical agents that increase the rate of genetic mutation by interfering with the function of nucleic acids. A clastogen is a specific mutagen that causes breaks in chromosomes.

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Weitere Aktionen
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CCRIS 1591Ptaquiloside (Braxin C)PTAQUILOSIDE [MI]PTAQUILOSIDE [IARC]orb1681843SCHEMBL3993356GLXC-19158HY-N7882

Datenbank-Bezeichner

CAS
87625-62-5
PubChem CID
13962857
DTXSID
DTXSID20892005
UNII
F0MN9S5699
Nikkaji
J128.594G
Carcinogen Classification · 5 Einträge

Ptaquiloside

Group 3: Not classifiable as to its carcinogenicity to humans

Volume 40: (1986) Some Naturally Occurring and Synthetic Food Components, Furocoumarins and Ultraviolet Radiation

1987

1987

Environmental Fate/Exposure Summary · 3 Einträge

The authors of this study presented the first mechanistic model for describing the generation and environmental fate of ptaquiloside (PTA), a carcinogenic phytotoxin produced by bracken fern. Their results show that only 4.4 % of the PTA produced in bracken is washed off by precipitation, from both canopy and litter. The model simulations showed that PTA degrades rapidly once in the soil, especially during summer due to the high soil temperatures. Leaching takes place in form of pulses directly connected to precipitation events, and macropore transport [the movement of water, air, and solutes through large pores (macropores) in soil],is mainly responsible for the events with the highest PTA concentrations. Based on the results, they identified areas with high density of bracken, high precipitation during the summer and soils characterized by fast transport, as the most vulnerable to surface and groundwater pollution by phytotoxins.

Bracken fern (Pteridium aquilinum (L.) Kuhn) is ubiquitous and acts as a cosmopolitan weed in pastures and similar environments. The substantial impact on biodiversity, animal health, and human well-being arises from the presence of ptaquiloside and related compounds in milk, meat, and water, along with the increasing global prevalence of P. aquilinum and its swift colonization in acidic soil and fire-damaged areas.

Bracken fern (Pteridium aquilinum) is the fifth most distributed common weed species of the world. Bracken fern contains different poisonous agents: some cyanogen glycosides, factors (agents) of antithiamine character (thermolabile thiaminase and thermostable other compounds) and factors of carcinogenic activity (the key example is ptaquiloside). This publication summarises and reviews different toxicological problems and poisonings caused by bracken fern in ruminants (cattle, sheep) and in non-ruminant animals (horses, pigs, rats, mice, etc.). The carcinogenic properties of ptaquiloside make bracken fern a potent hazard. Ptaquiloside may leach from the soil into the drinking water base. The carcinogenic effect of ptaquiloside is based on its hydrolysis, which leads to the formation of a dienon intermediate.