38710-26-8 Usage
Description
Seneciphylline N-oxide, a pyrrolizidine alkaloid, is a secondary metabolite derived from plants such as Senecio vulgaris and Adenostyles alliariae. It is a naturally occurring compound that serves as a protective mechanism against insect herbivores in various plant species, particularly within the Boraginaceae, Asteraceae, and Fabaceae families. Seneciphylline N-oxide is known for its high toxicity in mammals and is suspected to be mutagenic.
Uses
1. Used in Pharmaceutical Research:
Seneciphylline N-oxide is utilized as a research compound for its potential pharmaceutical applications. Due to its toxicity, it is studied for its effects on various biological systems and may contribute to the development of new drugs targeting specific conditions.
2. Used in Toxicological Studies:
As a highly toxic compound, Seneciphylline N-oxide is employed in toxicological research to understand its effects on mammalian systems. This knowledge can be applied to develop antidotes or countermeasures against its toxic effects and to study the mechanisms of action of similar compounds.
3. Used in Chemical Ecology:
Seneciphylline N-oxide serves as a subject of interest in chemical ecology, where it is investigated for its role in plant defense mechanisms against herbivores. Understanding these interactions can provide insights into the ecological roles of pyrrolizidine alkaloids and their impact on plant-insect relationships.
4. Used in Analytical Chemistry:
Seneciphylline N-oxide is also used in analytical chemistry for the development and validation of methods to detect and quantify pyrrolizidine alkaloids in plant extracts. This is crucial for assessing the potential risks associated with the consumption of plants containing these toxic compounds.
5. Used in Environmental Monitoring:
Seneciphylline N-oxide can be employed in environmental monitoring programs to detect the presence of toxic plant species in ecosystems. This information is vital for managing the risks associated with the exposure to these plants and their alkaloids.
6. Used in Forensic Science:
In forensic science, Seneciphylline N-oxide may be used as a marker for the presence of specific plant species in cases involving poisoning or other related incidents. Its detection can help in the identification of the source of the toxin and provide valuable evidence in legal investigations.
Occurance
Seneciphylline N-oxide is a pyrrolizidine alkaloid that is naturally found in the extracts of Adenostyles alliariae, a plant that is native to the western Alps. Seneciphylline N-oxide is highly toxic to mammals and is also a suspected mutagen.
Biological Activity
Seneciphylline N-Oxide is a dehydrogenation product of Senecionine N-oxide. Seneciphylline N-Oxide is a natural compound isolated from root cultures of Senecio erucifolius (Asteraceae).
Source
They are common food contaminants in herbs, tea, salad, leafy vegetables and honey. Feed can be contaminated so that the plant products find their way in the food chain indirectly also over meat, milk and eggs. Pyrrolizidine alkaloids have adverse health effects and were classified as genotoxic, carcinogen and hepatotoxic.
Check Digit Verification of cas no
The CAS Registry Mumber 38710-26-8 includes 8 digits separated into 3 groups by hyphens. The first part of the number,starting from the left, has 5 digits, 3,8,7,1 and 0 respectively; the second part has 2 digits, 2 and 6 respectively.
Calculate Digit Verification of CAS Registry Number 38710-26:
(7*3)+(6*8)+(5*7)+(4*1)+(3*0)+(2*2)+(1*6)=118
118 % 10 = 8
So 38710-26-8 is a valid CAS Registry Number.
InChI:InChI=1/C18H23NO6/c1-4-12-9-11(2)18(3,22)17(21)24-10-13-5-7-19(23)8-6-14(15(13)19)25-16(12)20/h4-5,14-15,22H,2,6-10H2,1,3H3/t14-,15-,18-,19?/m1/s1
38710-26-8Relevant articles and documents
Characteristic ion clusters as determinants for the identification of pyrrolizidine alkaloid N-oxides in pyrrolizidine alkaloid-containing natural products using HPLC-MS analysis
Ruan, Jianqing,Li, Na,Xia, Qingsu,Fu, Peter P.,Peng, Shuying,Ye, Yang,Lin, Ge
body text, p. 331 - 337 (2012/06/15)
Pyrrolizidine alkaloid (PA)-containing plants are widely distributed in the world. PAs are hepatotoxic, affecting livestock and humans. PA N-oxides are often present together with PAs in plants and also exhibit hepatotoxicity but with less potency. HPLC-MS is generally used to analyze PA-containing herbs, although PA references are unavailable in most cases. However, to date, without reference standards, HPLC-MS methodology cannot distinguish PA N-oxides from PAs because they both produce the same characteristic ions in mass spectra. In the present study, the mass spectra of 10 PA N-oxides and the corresponding PAs were systemically investigated using HPLC-MS to define the characteristic mass fragment ions specific to PAs and PA N-oxides. Mass spectra of toxic retronecine-type PA N-oxides exhibited two characteristic ion clusters at m/z 118-120 and 136-138. These ion clusters were produced by three unique fragmentation pathways of PA N-oxides and were not found in their corresponding PAs. Similarly, the nontoxic platynecine-type PA N-oxides also fragmented via three similar pathways to form two characteristic ion clusters at m/z 120-122 and 138-140. Further application of using these characteristic ion clusters allowed successful and rapid identification of PAs and PA N-oxides in two PA-containing herbal plants. Our results demonstrated, for the first time, that these characteristic ion clusters are unique determinants to discriminate PA N-oxides from PAs even without the availability of reference samples. Our findings provide a novel and specific method to differentiate PA N-oxides from PAs in PA-containing natural products, which is crucial for the assessment of their intoxication.
