38710-26-8 Usage
Description
Spartioidine N-oxide is a pyrrolizine alkaloid that is 13,19-didehydrosenecionane carrying a hydroxy substituent at position 12, two oxo substituents at positions 11 and 16 and an N-oxido substituent. It has a role as a Jacobaea metabolite. It is a macrocyclic lactone, an olefinic compound, an organic heterotricyclic compound, a pyrrolizine alkaloid, a tertiary alcohol and a tertiary amine oxide. It derives from a spartioidine.
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.
Uses
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.
General Description
Seneciphylline-N-oxide is a pyrrolizidine alkaloid isolated from Senecio vulgaris. Pyrrolizidine alkaloids are secondary metabolites, produced by several plant species as protection against insect herbivores. Approximately 6000 plant species worldwide may contain pyrrolizidine alkaloids. They are mainly found in the families of the Boraginaceae, Asteraceae and Fabaceae. The PA-content depends on several factors (species, plant organ, harvest, storage, extraction procedures). Contents vary from trace amounts up to 19 % based on dry weight. These alkaloids occur in two forms, as tertiary base PAs and their N-oxide (PANO).
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.
