Spartioidine (BioDeep_00000003328)

Secondary id: BioDeep_00000229983, BioDeep_00000375575

PANOMIX_OTCML-2023

代谢物信息卡片

Seneciphylline

化学式: C18H23NO5 (333.1576148)
中文名称: 千屈茶碱-D3, 千里光菲灵碱
谱图信息: 最多检出来源 Viridiplantae(plant) 4.74%

分子结构信息

SMILES: C/C=C\1/CC(=C)[C@@](C(=O)OCC2=CCN3[C@H]2[C@@H](CC3)OC1=O)(C)O
InChI: InChI=1S/C18H23NO5/c1-4-12-9-11(2)18(3,22)17(21)23-10-13-5-7-19-8-6-14(15(13)19)24-16(12)20/h4-5,14-15,22H,2,6-10H2,1,3H3

描述信息

A pyrrolizine alkaloid that is 13,19-didehydrosenecionane carrying a hydroxy substituent at position 12 and two oxo substituents at positions 11 and 16.
CONFIDENCE Reference Standard (Level 1); INTERNAL_ID 2297
[Raw Data] CB082b_Seneciphylline_pos_40eV_CB000034.txt
[Raw Data] CB082b_Seneciphylline_pos_30eV_CB000034.txt
[Raw Data] CB082b_Seneciphylline_pos_20eV_CB000034.txt
[Raw Data] CB082b_Seneciphylline_pos_10eV_CB000034.txt
[Raw Data] CB082b_Seneciphylline_pos_50eV_CB000034.txt
Seneciphylline is a toxic pyrrolizidine alkaloid in Gynura japonica[1]. Seneciphylline significantly increases the activities of epoxide hydrase and glutathione-S-transferase but causes reduction of cytochrome P-450 and related monooxygenase activities[2].

同义名列表

2 个代谢物同义名

Spartioidine; Seneciphylline

数据库引用编号

43 个数据库交叉引用编号

ChEBI: CHEBI:136405
ChEBI: CHEBI:181715
ChEBI: CHEBI:92677
ChEBI: CHEBI:9108
KEGG: C10391
PubChem: 5281750
PubChem: 521227
PubChem: 12577
Metlin: METLIN68299
ChEMBL: CHEMBL523911
KNApSAcK: C00026229
KNApSAcK: C00002117
CAS: 480-81-9
MoNA: NA002834
MoNA: NA002443
MoNA: NA002439
MoNA: NA002441
MoNA: FIO00242
MoNA: NA002440
MoNA: NA002838
MoNA: NA003216
MoNA: NA003218
MoNA: NA002442
MoNA: NA003215
MoNA: NA003580
MoNA: FIO00244
MoNA: NA003217
MoNA: FIO00240
MoNA: FIO00243
MoNA: NA003582
MoNA: NA003579
MoNA: NA002837
MoNA: NA003214
MoNA: NA003583
MoNA: NA003581
MoNA: NA002835
MoNA: FIO00241
MoNA: NA002836
PMhub: MS000009338
MetaboLights: MTBLC136405
3DMET: B03804
NIKKAJI: J15.536E
medchemexpress: HY-N1282

分类词条

代谢反应

0 个相关的代谢反应过程信息。

Reactome(0)

BioCyc(0)

WikiPathways(0)

Plant Reactome(0)

INOH(0)

PlantCyc(0)

COVID-19 Disease Map(0)

PathBank(0)

PharmGKB(0)

101 个相关的物种来源信息

462528 Senecio fistulosus: 10.1021/NP50045A025
76276 Senecio vulgaris:
98720 Senecio flaccidus var. douglasii:
214893 Jacobaea boissieri: 10.1016/J.PHYTOCHEM.2005.04.015
189241 Jacobaea minuta: 10.1016/J.PHYTOCHEM.2005.04.015
214899 Jacobaea uniflora:
214898 Jacobaea gnaphalioides: 10.1016/J.PHYTOCHEM.2005.04.015
189245 Jacobaea arnautorum: 10.1016/J.PHYTOCHEM.2005.04.015
214900 Jacobaea leucophylla:
214901 Jacobaea othonnae: 10.1016/J.PHYTOCHEM.2005.04.015
189239 Jacobaea incana:
189226 Jacobaea adonidifolia: 10.1016/J.PHYTOCHEM.2005.04.015
189230 Jacobaea aquatica:
214897 Jacobaea gigantea: 10.1016/J.PHYTOCHEM.2005.04.015
214902 Jacobaea persoonii:
214896 Jacobaea delphiniifolia: 10.1016/J.PHYTOCHEM.2005.04.015
189228 Jacobaea ambigua: 10.1016/J.PHYTOCHEM.2005.04.015
189232 Jacobaea cannabifolia: 10.1016/J.PHYTOCHEM.2005.04.015
189250 Jacobaea subalpina:
189240 Jacobaea carniolica: 10.1016/J.PHYTOCHEM.2005.04.015
85882 Senecio viscosus: 10.1016/S0176-1617(86)80085-2
58524 Senecio inaequidens:
93496 Senecio vernalis:
121553 Senecio rupestris: 10.1016/S0176-1617(86)80085-2
189227 Jacobaea alpina: 10.1016/S0176-1617(86)80085-2
183623 Senecio brasiliensis: 10.1021/JA01601A044
98721 Senecio eremophilus: 10.1021/JA01601A044
1886452 Senecio rosmarinifolius: 10.1139/CJR39B-002
118778 Tussilago farfara: 10.1007/978-3-642-49340-9_21
278673 Petasites hybridus: 10.1055/S-2006-957875
1896791 Senecio ruwenzoriensis: 10.1016/0031-9422(93)85124-A
3829 Crotalaria juncea: 10.1021/JA01590A040
121552 Senecio rodriguezii: 10.1002/NT.2620010407
121546 Senecio glaucus: 10.1055/S-2007-971305
82364 Senecio pterophorus: 10.1016/S0031-9422(00)90859-8
52725 Melampyrum pratense: 10.1002/NT.2620010108
186967 Jacobaea argunensis: 10.1016/S0031-9422(00)95221-X
13037 Danaus plexippus: 10.1007/BF01951680
76228 Danaus genutia: 10.1007/BF01951680
1346275 Adenostyles alliariae:
1395540 Adenostyles glabra: 10.1002/ARDP.19843170202
462557 Senecio sarracenicus: 10.1135/CCCC19732658
186954 Ligularia fischeri: 10.1038/106503D0
1129149 Senecio bollei: 10.1038/106503D0
1268588 Senecio racemosus: 10.1038/106503D0
465548 Senecio flaccidus var. flaccidus:
76276 Senecio vulgaris:
1395540 Adenostyles glabra: 10.1135/CCCC19691739
1346275 Adenostyles alliariae: 10.1135/CCCC19691739
98720 Senecio flaccidus var. douglasii: 10.1021/JA01174A015
462528 Senecio fistulosus: 10.1021/NP50045A025
76276 Senecio vulgaris:
98720 Senecio flaccidus var. douglasii:
214893 Jacobaea boissieri: 10.1016/J.PHYTOCHEM.2005.04.015
189241 Jacobaea minuta: 10.1016/J.PHYTOCHEM.2005.04.015
214899 Jacobaea uniflora:
214898 Jacobaea gnaphalioides: 10.1016/J.PHYTOCHEM.2005.04.015
189245 Jacobaea arnautorum: 10.1016/J.PHYTOCHEM.2005.04.015
214900 Jacobaea leucophylla:
214901 Jacobaea othonnae: 10.1016/J.PHYTOCHEM.2005.04.015
189239 Jacobaea incana:
189226 Jacobaea adonidifolia: 10.1016/J.PHYTOCHEM.2005.04.015
189230 Jacobaea aquatica:
214897 Jacobaea gigantea: 10.1016/J.PHYTOCHEM.2005.04.015
214902 Jacobaea persoonii:
214896 Jacobaea delphiniifolia: 10.1016/J.PHYTOCHEM.2005.04.015
189228 Jacobaea ambigua: 10.1016/J.PHYTOCHEM.2005.04.015
189232 Jacobaea cannabifolia: 10.1016/J.PHYTOCHEM.2005.04.015
189250 Jacobaea subalpina:
189240 Jacobaea carniolica: 10.1016/J.PHYTOCHEM.2005.04.015
85882 Senecio viscosus: 10.1016/S0176-1617(86)80085-2
58524 Senecio inaequidens:
93496 Senecio vernalis:
121553 Senecio rupestris: 10.1016/S0176-1617(86)80085-2
189227 Jacobaea alpina: 10.1016/S0176-1617(86)80085-2
183623 Senecio brasiliensis: 10.1021/JA01601A044
98721 Senecio eremophilus: 10.1021/JA01601A044
1886452 Senecio rosmarinifolius: 10.1139/CJR39B-002
118778 Tussilago farfara: 10.1007/978-3-642-49340-9_21
278673 Petasites hybridus: 10.1055/S-2006-957875
1896791 Senecio ruwenzoriensis: 10.1016/0031-9422(93)85124-A
3829 Crotalaria juncea: 10.1021/JA01590A040
121552 Senecio rodriguezii: 10.1002/NT.2620010407
121546 Senecio glaucus: 10.1055/S-2007-971305
82364 Senecio pterophorus: 10.1016/S0031-9422(00)90859-8
52725 Melampyrum pratense: 10.1002/NT.2620010108
186967 Jacobaea argunensis: 10.1016/S0031-9422(00)95221-X
13037 Danaus plexippus: 10.1007/BF01951680
76228 Danaus genutia: 10.1007/BF01951680
1346275 Adenostyles alliariae:
1395540 Adenostyles glabra: 10.1002/ARDP.19843170202
462557 Senecio sarracenicus: 10.1135/CCCC19732658
186954 Ligularia fischeri: 10.1038/106503D0
1129149 Senecio bollei: 10.1038/106503D0
1268588 Senecio racemosus: 10.1038/106503D0
465548 Senecio flaccidus var. flaccidus:
76276 Senecio vulgaris:
1395540 Adenostyles glabra: 10.1135/CCCC19691739
1346275 Adenostyles alliariae: 10.1135/CCCC19691739
98720 Senecio flaccidus var. douglasii: 10.1021/JA01174A015
33090 Plants: -

在这里通过桑基图来展示出与当前的这个代谢物在我们的BioDeep知识库中具有相关联信息的其他代谢物。在这里进行关联的信息来源主要有：

PubMed: 来源于PubMed文献库中的文献信息，我们通过自然语言数据挖掘得到的在同一篇文献中被同时提及的相关代谢物列表，这个列表按照代谢物同时出现的文献数量降序排序，取前10个代谢物作为相关研究中关联性很高的代谢物集合展示在桑基图中。
NCBI Taxonomy: 通过文献数据挖掘，得到的代谢物物种来源信息关联。这个关联信息同样按照出现的次数降序排序，取前10个代谢物作为高关联度的代谢物集合展示在桑吉图上。
Chemical Taxonomy: 在物质分类上处于同一个分类集合中的其他代谢物
Chemical Reaction: 在化学反应过程中，存在为当前代谢物相关联的生化反应过程中的反应底物或者反应产物的关联代谢物信息。

点击图上的相关代谢物的名称，可以跳转到相关代谢物的信息页面。

文献列表

Feng Long, Jie Ji, Xin Wang, Lili Wang, Ting Chen. LC-MS/MS method for determination of seneciphylline and its metabolite, seneciphylline N-oxide in rat plasma, and its application to a rat pharmacokinetic study. Biomedical chromatography : BMC. 2021 Sep; 35(9):e5145. doi: 10.1002/bmc.5145. [PMID: 33886121]
Lukas Rutz, Lan Gao, Jan-Heiner Küpper, Dieter Schrenk. Structure-dependent genotoxic potencies of selected pyrrolizidine alkaloids in metabolically competent HepG2 cells. Archives of toxicology. 2020 12; 94(12):4159-4172. doi: 10.1007/s00204-020-02895-z. [PMID: 32910235]
Weiqian Wang, Xiao Yang, Yan Chen, Xuanling Ye, Kaiyuan Jiang, Aizhen Xiong, Li Yang, Zhengtao Wang. Seneciphylline, a main pyrrolizidine alkaloid in Gynura japonica, induces hepatotoxicity in mice and primary hepatocytes via activating mitochondria-mediated apoptosis. Journal of applied toxicology : JAT. 2020 11; 40(11):1534-1544. doi: 10.1002/jat.4004. [PMID: 32618019]
Xiaojie Liu, Peter G L Klinkhamer, Klaas Vrieling. The effect of structurally related metabolites on insect herbivores: A case study on pyrrolizidine alkaloids and western flower thrips. Phytochemistry. 2017 Jun; 138(?):93-103. doi: 10.1016/j.phytochem.2017.02.027. [PMID: 28267991]
Reuel A Field, Bryan L Stegelmeier, Steven M Colegate, Ammon W Brown, Benedict T Green. An in vitro comparison of the cytotoxic potential of selected dehydropyrrolizidine alkaloids and some N-oxides. Toxicon : official journal of the International Society on Toxinology. 2015 Apr; 97(?):36-45. doi: 10.1016/j.toxicon.2015.02.001. [PMID: 25666399]
Jia-Yin Han, Yan Yi, Ai-Hua Liang, Yu-Shi Zhang, Chun-Ying Li, Yong Zhao, Hong-Yu Cui, Yu-Ting Lu. [Embryotoxicity of Senecionis Scandentis Hebra on in vitro cultured mouse embryos]. Yao xue xue bao = Acta pharmaceutica Sinica. 2014 Sep; 49(9):1267-72. doi: . [PMID: 25518325]
Tri R Nuringtyas, Robert Verpoorte, Peter G L Klinkhamer, Monique M van Oers, Kirsten A Leiss. Toxicity of pyrrolizidine alkaloids to Spodoptera exigua using insect cell lines and injection bioassays. Journal of chemical ecology. 2014 Jun; 40(6):609-16. doi: 10.1007/s10886-014-0459-4. [PMID: 24981118]
Dandan Cheng, Heather Kirk, Klaas Vrieling, Patrick P J Mulder, Peter G L Klinkhamer. The relationship between structurally different pyrrolizidine alkaloids and western flower thrips resistance in F(2) hybrids of Jacobaea vulgaris and Jacobaea aquatica. Journal of chemical ecology. 2011 Oct; 37(10):1071-80. doi: 10.1007/s10886-011-0021-6. [PMID: 21969251]
Xuejing Yang, Li Yang, Aizhen Xiong, Dingxiang Li, Zhengtao Wang. Authentication of Senecio scandens and S. vulgaris based on the comprehensive secondary metabolic patterns gained by UPLC-DAD/ESI-MS. Journal of pharmaceutical and biomedical analysis. 2011 Sep; 56(2):165-72. doi: 10.1016/j.jpba.2011.05.004. [PMID: 21664784]
Gregory Röder, Martine Rahier, Russell E Naisbit. Do induced responses mediate the ecological interactions between the specialist herbivores and phytopathogens of an alpine plant?. PloS one. 2011 May; 6(5):e19571. doi: 10.1371/journal.pone.0019571. [PMID: 21573247]
Ge Lin, Ji Yao Wang, Na Li, Mi Li, Hong Gao, Yuan Ji, Fan Zhang, Huali Wang, Yan Zhou, Yang Ye, Hong Xi Xu, Jiang Zheng. Hepatic sinusoidal obstruction syndrome associated with consumption of Gynura segetum. Journal of hepatology. 2011 Apr; 54(4):666-73. doi: 10.1016/j.jhep.2010.07.031. [PMID: 21146894]
Heather Kirk, Klaas Vrieling, Eddy Van Der Meijden, Peter G L Klinkhamer. Species by environment interactions affect pyrrolizidine alkaloid expression in Senecio jacobaea, Senecio aquaticus, and their hybrids. Journal of chemical ecology. 2010 Apr; 36(4):378-87. doi: 10.1007/s10886-010-9772-8. [PMID: 20309618]
Xueyong Qi, Bin Wu, Yiyu Cheng, Haibin Qu. Simultaneous characterization of pyrrolizidine alkaloids and N-oxides in Gynura segetum by liquid chromatography/ion trap mass spectrometry. Rapid communications in mass spectrometry : RCM. 2009 Jan; 23(2):291-302. doi: 10.1002/rcm.3862. [PMID: 19072862]
Song-Lin Li, Ge Lin, Peter P Fu, Chi-Leung Chan, Mi Li, Zhi-Hong Jiang, Zhong-Zhen Zhao. Identification of five hepatotoxic pyrrolizidine alkaloids in a commonly used traditional Chinese medicinal herb, Herba Senecionis scandentis (Qianliguang). Rapid communications in mass spectrometry : RCM. 2008; 22(4):591-602. doi: 10.1002/rcm.3398. [PMID: 18220326]
Rajendra P Tangallapally, Robin E B Lee, Anne J M Lenaerts, Richard E Lee. Synthesis of new and potent analogues of anti-tuberculosis agent 5-nitro-furan-2-carboxylic acid 4-(4-benzyl-piperazin-1-yl)-benzylamide with improved bioavailability. Bioorganic & medicinal chemistry letters. 2006 May; 16(10):2584-9. doi: 10.1016/j.bmcl.2006.02.048. [PMID: 16529927]
Lijun Yu, Yan Xu, Huatao Feng, Sam Fong Yau Li. Separation and determination of toxic pyrrolizidine alkaloids in traditional Chinese herbal medicines by micellar electrokinetic chromatography with organic modifier. Electrophoresis. 2005 Sep; 26(17):3397-404. doi: 10.1002/elps.200500233. [PMID: 16080213]
Brian T Schaneberg, Russell J Molyneux, Ikhlas A Khan. Evaporative light scattering detection of pyrrolizidine alkaloids. Phytochemical analysis : PCA. 2004 Jan; 15(1):36-9. doi: 10.1002/pca.715. [PMID: 14979525]
H Eröksüz, Y Eröksüz, H Ozer, I Yaman, F Tosun, C Akyüz Kizilay, U Tamer. Toxicity of Senecio vernalis to laying hens and evaluation of residues in eggs. Veterinary and human toxicology. 2003 Mar; 45(2):76-80. doi: . [PMID: 12678291]
Jeannette T Hovermale, A Morrie Craig. Metabolism of pyrrolizidine alkaloids by Peptostreptococcus heliotrinreducens and a mixed culture derived from ovine ruminal fluid. Biophysical chemistry. 2002 Dec; 101-102(?):387-99. doi: 10.1016/s0301-4622(02)00152-7. [PMID: 12488016]
Veselin S Christov, Bozhanka P Mikhova, Luba N Evstatieva. Alkaloids from Senecio aquaticus. Fitoterapia. 2002 Apr; 73(2):171-3. doi: 10.1016/s0367-326x(02)00012-6. [PMID: 11978435]
M T Skaanild, C Friis, L Brimer. Interplant alkaloid variation and Senecio vernalis toxicity in cattle. Veterinary and human toxicology. 2001 Jun; 43(3):147-51. doi: . [PMID: 11383654]
M Noorwala, F V Mohammad, V U Ahmad, B Sener, F Ergun, D Deliorman. Pyrrolizidine alkaloids from Senecio lorenthii. Fitoterapia. 2000 Sep; 71(5):618-20. doi: 10.1016/s0367-326x(00)00194-5. [PMID: 11449528]
G T Tan, J M Pezzuto, A D Kinghorn, S H Hughes. Evaluation of natural products as inhibitors of human immunodeficiency virus type 1 (HIV-1) reverse transcriptase. Journal of natural products. 1991 Jan; 54(1):143-54. doi: 10.1021/np50073a012. [PMID: 1710653]
U Candrian, J Lüthy, C Schlatter. In vivo covalent binding of retronecine-labelled [3H]seneciphylline and [3H]senecionine to DNA of rat liver, lung and kidney. Chemico-biological interactions. 1985 Jun; 54(1):57-69. doi: 10.1016/s0009-2797(85)80152-6. [PMID: 4017105]
D F Eastman, G P Dimenna, H J Segall. Covalent binding of two pyrrolizidine alkaloids, senecionine and seneciphylline, to hepatic macromolecules and their distribution, excretion, and transfer into milk of lactating mice. Drug metabolism and disposition: the biological fate of chemicals. 1982 May; 10(3):236-40. doi: . [PMID: 6179729]