Skimmianin (BioDeep_00000861621)
PANOMIX_OTCML-2023 Cytotoxicity
代谢物信息卡片
InChI=1\C14H13NO4\c1-16-10-5-4-8-11(13(10)18-3)15-14-9(6-7-19-14)12(8)17-2\h4-7H,1-3H
化学式: C14H13NO4 (259.0844538)
中文名称: 茵芋碱
谱图信息:
最多检出来源 () 0%
分子结构信息
SMILES: COC1=C(C2=C(C=C1)C(=C3C=COC3=N2)OC)OC
InChI: InChI=1S/C14H13NO4/c1-16-10-5-4-8-11(13(10)18-3)15-14-9(6-7-19-14)12(8)17-2/h4-7H,1-3H3
描述信息
Skimmianine is a furoquinoline alkaloid present mainly in the Rutaceae family, with antispastic, anti-inflammatory activities and antiplatelet aggregation effect. Skimmianine exhibits cytotoxicity against a variety of cancer cell lines and genotoxicity[1].
Skimmianine is a furoquinoline alkaloid present mainly in the Rutaceae family, with antispastic, anti-inflammatory activities and antiplatelet aggregation effect. Skimmianine exhibits cytotoxicity against a variety of cancer cell lines and genotoxicity[1].
同义名列表
43 个代谢物同义名
InChI=1\C14H13NO4\c1-16-10-5-4-8-11(13(10)18-3)15-14-9(6-7-19-14)12(8)17-2\h4-7H,1-3H; 4-27-00-02296 (Beilstein Handbook Reference); FURO(2,3-b)QUINOLINE, 4,7,8-TRIMETHOXY-; Furo[2,3-b]quinoline, 4,7,8-trimethoxy-; 4,7,8-Trimethoxyfuro[2,3-b]quinoline; Prestwick2_000668; Prestwick0_000668; Prestwick1_000668; Prestwick3_000668; BIM-0015492.P001; NCGC00016333-01; .beta.-Fagarine; NCGC00142348-01; NCGC00016333-02; CBMicro_015540; Chloroxylonine; beta-Fagarine; BSPBio_000735; Oprea1_449938; MEGxp0_000036; BPBio1_000809; Prestwick_184; Oprea1_598261; SMR000386971; MLS001049147; SPBio_002656; ZINC00035525; Skimmiamine; BRN 0028904; AIDS-196564; CAS-83-95-4; Skimmianine; AIDS196564; Skimmianin; NSC 217986; CCRIS 1585; 5255-76-5; NSC217986; ST005173; NSC94654; TNP00202; 83-95-4; C10740
数据库引用编号
6 个数据库交叉引用编号
- ChEBI: CHEBI:9172
- PubChem: 6760
- ChEMBL: CHEMBL21396
- CAS: 5255-76-5
- CAS: 83-95-4
- medchemexpress: HY-N2081
分类词条
相关代谢途径
Reactome(0)
BioCyc(0)
PlantCyc(0)
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)
121 个相关的物种来源信息
- 354485 - Acronychia pedunculata:
- 549407 - Adiscanthus fusciflorus: 10.3390/MOLECULES190812031
- 68527 - Aegle marmelos:
- 378919 - Agathosma: 10.1016/0031-9422(90)85447-N
- 1641041 - Agathosma bisulca: 10.1016/S0031-9422(00)81426-0
- 430971 - Agathosma capensis: 10.1016/S0031-9422(00)81426-0
- 1654682 - Almeidea rubra: 10.1590/S0103-50531998000100007
- 549412 - Balfourodendron riedelianum: 10.2307/4117899
- 1226053 - Boronia ternata: 10.1071/CH9630292
- 68535 - Casimiroa edulis:
- 416188 - Choisya ternata: 10.1039/B707576F
- 76957 - Chorilaena quercifolia: 10.1016/0031-9422(96)00355-X
- 159034 - Clausena anisata: 10.1002/HLCA.200390259
- 1224754 - Clausena dunniana: 10.1002/HLCA.200390259
- 2899779 - Decatropis bicolor:
- 298346 - Dictamnus albus:
- 714465 - Dictamnus dasycarpus: 10.1016/S0031-9422(98)00519-6
- 714465 - Dictamnus dasycarpus Turcz.: -
- 1226072 - Drummondita calida: 10.1055/S-0030-1270963
- 282608 - Drummondita hassellii: 10.1016/0031-9422(92)80274-I
- 2820928 - Ertela trifolia:
- 1654694 - Esenbeckia febrifuga: 10.1016/J.PHYMED.2008.02.001
- 549402 - Esenbeckia grandiflora: 10.1016/J.FITOTE.2003.08.004
- 1344466 - Esenbeckia leiocarpa: 10.3390/MOLECULES15129205
- 67923 - Flindersia bennettiana: 10.1071/CH9600427
- 67931 - Flindersia laevicarpa:
- 67932 - Flindersia maculosa: 10.1071/CH9570480
- 1081050 - Geijera salicifolia:
- 650008 - Glycosmis citrifolia: 10.1016/0031-9422(95)00171-3
- 1489662 - Glycosmis macrophylla: 10.1016/J.PHYTOL.2011.03.002
- 159045 - Glycosmis mauritiana:
- 159048 - Glycosmis parviflora: 10.1016/0031-9422(95)00171-3
- 76967 - Glycosmis pentaphylla:
- 159052 - Glycosmis trichanthera: 10.1016/S0031-9422(97)00986-2
- 452768 - Haplophyllum acutifolium:
- 1006069 - Haplophyllum bucharicum:
- 452770 - Haplophyllum bungei:
- 452771 - Haplophyllum buxbaumii: 10.1016/S0031-9422(00)83563-3
- 1006070 - Haplophyllum cappadocicum: 10.1016/0031-9422(92)83302-F
- 452773 - Haplophyllum dauricum: 10.1007/BF00574794
- 1006075 - Haplophyllum griffithianum:
- 452777 - Haplophyllum latifolium:
- 1006077 - Haplophyllum myrtifolium: 10.1016/S0367-326X(03)00147-3
- 452779 - Haplophyllum obtusifolium:
- 452780 - Haplophyllum patavinum: 10.1080/10575630290019985
- 1006078 - Haplophyllum popovii: 10.2307/4117899
- 1006079 - Haplophyllum ramosissimum:
- 452782 - Haplophyllum robustum: 10.2307/4117899
- 1006083 - Haplophyllum thesioides:
- 452784 - Haplophyllum tuberculatum:
- 549422 - Hortia longifolia: 10.1021/JO00829A053
- 1793828 - Leionema nudum:
- 408134 - Melicope quadrilocularis: 10.1248/CPB.56.727
- 697038 - Melicope semecarpifolia:
- 354503 - Melicope triphylla:
- 1312821 - Melicope xanthoxyloides: 10.2307/4117899
- 549427 - Metrodorea nigra: 10.1016/0031-9422(95)00504-Z
- 2901850 - Murraya exotica L.: -
- 43711 - Murraya paniculata (L.)Jack: -
- 2057143 - Myrtopsis macrocarpa: 10.1016/S0031-9422(00)86717-5
- 68552 - Nematolepis phebalioides: 10.1021/NP50100A030
- 354507 - Orixa japonica:
- 1136780 - Peltostigma guatemalense: 10.1080/14786410802228439
- 77003 - Phebalium: 10.2307/4117899
- 68554 - Phellodendron amurense: 10.1016/S0031-9422(97)01130-8
- 2492889 - Philotheca thryptomenoides: 10.1016/0305-1978(94)90095-7
- 1226106 - Picrella glandulosa:
- 1279153 - Pitavia punctata: 10.1016/S0031-9422(00)97383-7
- 33090 - Plants: -
- 2042453 - Ptelea crenulata: 10.1016/S0031-9422(00)86348-7
- 2321333 - Raputia praetermissa: 10.1590/S0103-50532011000700021
- 2894648 - Raputiarana heptaphylla: 10.1248/CPB.59.855
- 452790 - Ruta chalepensis:
- 452791 - Ruta corsica: 10.1016/J.FITOTE.2003.12.014
- 37565 - Ruta graveolens:
- 675743 - Ruta macrophylla: 10.1007/BF00055511
- 76972 - Sarcomelicope simplicifolia: 10.1016/0031-9422(88)84136-0
- 210365 - Skimmia japonica:
- 354517 - Skimmia reevesiana: 10.1016/S0031-9422(00)84814-1
- 2896588 - Spiranthera odoratissima:
- 2896591 - Stauranthus perforatus: 10.1055/S-2000-8595
- 482953 - Teclea simplicifolia: 10.1016/0031-9422(88)84136-0
- 354522 - Tetradium glabrifolium: 10.1016/0031-9422(95)00248-6
- 354523 - Tetradium ruticarpum: 10.1002/CBDV.200900289
- 452797 - Thamnosma montana: 10.1016/S0040-4020(01)99086-6
- 1220089 - Vepris nobilis:
- 549433 - Vepris simplicifolia: 10.1016/0031-9422(88)84136-0
- 1317904 - Vepris soyauxii:
- 2709026 - Vepris suaveolens: 10.1021/NP800276F
- 2695420 - Vepris trichocarpa: 10.1021/NP0106182
- 159071 - Zanthoxylum ailanthoides:
- 2839963 - Zanthoxylum asiaticum:
- 354527 - Zanthoxylum avicennae:
- 1056465 - Zanthoxylum beecheyanum: 10.1002/JCCS.200400159
- 328401 - Zanthoxylum bungeanum Maxim.: -
- 430988 - Zanthoxylum capense: 10.1016/S0031-9422(00)85715-5
- 1671342 - Zanthoxylum chalybeum:
- 2099532 - Zanthoxylum coco:
- 1475459 - Zanthoxylum culantrillo:
- 1899209 - Zanthoxylum delagoense: 10.1016/S0031-9422(00)85715-5
- 2839964 - Zanthoxylum dimorphophyllum: 10.1002/JCCS.200400099
- 681508 - Zanthoxylum ekmanii: 10.1016/S0031-9422(00)91132-4
- 1291627 - Zanthoxylum gilletii:
- 992815 - Zanthoxylum leprieurii:
- 1056472 - Zanthoxylum mayu:
- 354528 - Zanthoxylum nitidum:
- 354528 - Zanthoxylum Nitidum: -
- 549434 - Zanthoxylum rhoifolium:
- 1336656 - Zanthoxylum scandens: 10.1055/S-2006-961713
- 354530 - Zanthoxylum schinifolium:
- 354530 - Zanthoxylum schinifolium Sieb. et Zucc.: -
- 328402 - Zanthoxylum simulans:
- 2714546 - Zanthoxylum tragodes: 10.2307/4117899
- 2099547 - Zanthoxylum viride: 10.2307/4117899
- 697043 - Zanthoxylum wutaiense: 10.1021/NP700719E
- 2099548 - Zanthoxylum zanthoxyloides:
- 354528 - 两面针: -
- 33090 - 常山: -
- 33090 - 白鲜皮: -
- 33090 - 花椒: -
- 33090 - 黄柏: -
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
- Folashade A Ogunrinade, Stephanie T Guetchueng, Folashade O Katola, Mutalib A Aderogba, Idowu S Akande, Satyajit D Sarker, Olumayokun A Olajide. Zanthoxylum zanthoxyloides inhibits lipopolysaccharide- and synthetic hemozoin-induced neuroinflammation in BV-2 microglia: roles of NF-κB transcription factor and NLRP3 inflammasome activation.
The Journal of pharmacy and pharmacology.
2021 Mar; 73(1):118-134. doi:
10.1093/jpp/rgaa019. [PMID: 33791805] - Yixuan Li, Weihua Zhang, Tingting Yin, Ce Wang, Feige Wang, Jing Sun, Lina Liu, Qinghuai Zhang, Chunze Zhang. Inhibition of UDP-glucuronosyltransferases by different furoquinoline alkaloids.
Xenobiotica; the fate of foreign compounds in biological systems.
2020 Oct; 50(10):1170-1179. doi:
10.1080/00498254.2020.1760400. [PMID: 32367776] - Natarajan Murugan, Ramalingam Srinivasan, Athiappan Murugan, Myunghee Kim, Devarajan Natarajan. Glycosmis pentaphylla (Rutaceae): A Natural Candidate for the Isolation of Potential Bioactive Arborine and Skimmianine Compounds for Controlling Multidrug-Resistant Staphylococcus aureus.
Frontiers in public health.
2020; 8(?):176. doi:
10.3389/fpubh.2020.00176. [PMID: 32587843] - Tobie D Lee, Olivia W Lee, Kyle R Brimacombe, Lu Chen, Rajarshi Guha, Sabrina Lusvarghi, Bethilehem G Tebase, Carleen Klumpp-Thomas, Robert W Robey, Suresh V Ambudkar, Min Shen, Michael M Gottesman, Matthew D Hall. A High-Throughput Screen of a Library of Therapeutics Identifies Cytotoxic Substrates of P-glycoprotein.
Molecular pharmacology.
2019 11; 96(5):629-640. doi:
10.1124/mol.119.115964. [PMID: 31515284] - Blaise Kemajou Nganou, Armelle T Mbaveng, Serge A T Fobofou, Aimé G Fankam, Gabin Thierry M Bitchagno, James D Simo Mpetga, Ludger A Wessjohann, Victor Kuete, Thomas Efferth, Pierre Tane. Furoquinolines and dihydrooxazole alkaloids with cytotoxic activity from the stem bark of Araliopsis soyauxii.
Fitoterapia.
2019 Mar; 133(?):193-199. doi:
10.1016/j.fitote.2019.01.003. [PMID: 30654126] - Aihua Huang, Hui Xu, Ruoting Zhan, Weiwen Chen, Jiawei Liu, Yuguang Chi, Daidi Chen, Xiaoyu Ji, Chaoquan Luo. Metabolic Profile of Skimmianine in Rats Determined by Ultra-Performance Liquid Chromatography Coupled with Quadrupole Time-of-Flight Tandem Mass Spectrometry.
Molecules (Basel, Switzerland).
2017 Mar; 22(4):. doi:
10.3390/molecules22040489. [PMID: 28333075] - Jian-Bo Sun, Wei Qu, Fu-Qin Guan, Lin-Zhen Li, Jing-Yu Liang. A new quinoline alkaloid from the roots of Dictamnus angustifolius.
Chinese journal of natural medicines.
2014 Mar; 12(3):222-4. doi:
10.1016/s1875-5364(14)60037-6. [PMID: 24702810] - Tayyab A Mansoor, Pedro M Borralho, Xuan Luo, Silva Mulhovo, Cecília M P Rodrigues, Maria-José U Ferreira. Apoptosis inducing activity of benzophenanthridine-type alkaloids and 2-arylbenzofuran neolignans in HCT116 colon carcinoma cells.
Phytomedicine : international journal of phytotherapy and phytopharmacology.
2013 Jul; 20(10):923-9. doi:
10.1016/j.phymed.2013.03.026. [PMID: 23643093] - M Ratheesh, G Sindhu, Antony Helen. Anti-inflammatory effect of quinoline alkaloid skimmianine isolated from Ruta graveolens L.
Inflammation research : official journal of the European Histamine Research Society ... [et al.].
2013 Apr; 62(4):367-76. doi:
10.1007/s00011-013-0588-1. [PMID: 23344232] - Xuan Luo, David Pires, José A Aínsa, Begoña Gracia, Noélia Duarte, Silva Mulhovo, Elsa Anes, Maria-José U Ferreira. Zanthoxylum capense constituents with antimycobacterial activity against Mycobacterium tuberculosis in vitro and ex vivo within human macrophages.
Journal of ethnopharmacology.
2013 Mar; 146(1):417-22. doi:
10.1016/j.jep.2013.01.013. [PMID: 23337743] - Ikarastika Rahayu Abdul Wahab, Nikki Siu Hai Wong, Fabio Boylan. Choisyaternatine, a new alkaloid isolated from Choisya ternata.
Planta medica.
2012 Sep; 78(14):1597-600. doi:
10.1055/s-0032-1315044. [PMID: 22815205] - Yigen Li, Wenjin Huang, Shenyuan Huang, Jiulin Du, Cheng Huang. Screening of anti-cancer agent using zebrafish: comparison with the MTT assay.
Biochemical and biophysical research communications.
2012 May; 422(1):85-90. doi:
10.1016/j.bbrc.2012.04.110. [PMID: 22560901] - Rogerio Alexandre Nunes Dos Santos, João Batista, Suellen Iara Guirra Rosa, Heron Fernandes Torquato, Carmen Lúcia Bassi, Tereza Auxiliadora Nascimento Ribeiro, Paulo Teixeira De Sousa, Angela Márcia Selhorst E Silva Bessera, Cor Jesus Fernandes Fontes, Luiz Everson Da Silva, Márcia Regina Piuvezam. Leishmanicidal effect of Spiranthera odoratíssima (Rutaceae) and its isolated alkaloid skimmianine occurs by a nitric oxide dependent mechanism.
Parasitology.
2011 Sep; 138(10):1224-33. doi:
10.1017/s0031182011001168. [PMID: 21810308] - Min Zhang, Yin Long, Yang Sun, Yukun Wang, Qian Li, Huanjie Wu, Zhenjun Guo, Yuhua Li, Yinbo Niu, Chen Li, Li Liu, Qibing Mei. Evidence for the complementary and synergistic effects of the three-alkaloid combination regimen containing berberine, hypaconitine and skimmianine on the ulcerative colitis rats induced by trinitrobenzene-sulfonic acid.
European journal of pharmacology.
2011 Jan; 651(1-3):187-96. doi:
10.1016/j.ejphar.2010.10.030. [PMID: 20969848] - Tzu-Ying Wang, Jin-Bin Wu, Tsong-Long Hwang, Yueh-Hsiung Kuo, Jih-Jung Chen. A new quinolone and other constituents from the fruits of Tetradium ruticarpum: effects on neutrophil pro-inflammatory responses.
Chemistry & biodiversity.
2010 Jul; 7(7):1828-34. doi:
10.1002/cbdv.200900289. [PMID: 20658672] - Zhi Long Liu, Sha Sha Chu, Guo Hua Jiang. Feeding deterrents from Zanthoxylum schinifolium against two stored-product insects.
Journal of agricultural and food chemistry.
2009 Nov; 57(21):10130-3. doi:
10.1021/jf9012983. [PMID: 19886679] - Luis Enrique Cuca Suarez, Manuel Elkin Pattarroyo, Jose Manuel Lozano, Franco Delle Monache. Biological activity of secondary metabolites from Peltostigma guatemalense.
Natural product research.
2009; 23(4):370-4. doi:
10.1080/14786410802228439. [PMID: 19296377] - Jih-Jung Chen, Tzu-Ying Wang, Tsong-Long Hwang. Neolignans, a coumarinolignan, lignan derivatives, and a chromene: anti-inflammatory constituents from Zanthoxylum avicennae.
Journal of natural products.
2008 Feb; 71(2):212-7. doi:
10.1021/np070594k. [PMID: 18211005] - Ipek Ostan, Hüsniye Saglam, M Emin Limoncu, Hatice Ertabaklar, Seray Ozensoy Toz, Yusuf Ozbel, Ahmet Ozbilgin. In vitro and in vivo activities of Haplophyllum myrtifolium against Leishmania tropica.
The new microbiologica.
2007 Oct; 30(4):439-45. doi:
. [PMID: 18080680] - Ming-Jen Cheng, Kuo-Hsiung Lee, Ian-Lih Tsai, Ih-Sheng Chen. Two new sesquiterpenoids and anti-HIV principles from the root bark of Zanthoxylum ailanthoides.
Bioorganic & medicinal chemistry.
2005 Nov; 13(21):5915-20. doi:
10.1016/j.bmc.2005.07.050. [PMID: 16140017] - Mary W Muriithi, W-R Abraham, Jonathan Addae-Kyereme, Ian Scowen, Simon L Croft, Peter M Gitu, Howard Kendrick, E N M Njagi, Colin W Wright. Isolation and in vitro antiplasmodial activities of alkaloids from Teclea trichocarpa: in vivo antimalarial activity and X-ray crystal structure of normelicopicine.
Journal of natural products.
2002 Jul; 65(7):956-9. doi:
10.1021/np0106182. [PMID: 12141852] - Neusa F de Moura, Ademir F Morel, Emilia C Dessoy, Nilo Zanatta, Marilise M Bürger, Neusa Ahlert, Gerusa P Porto, Bernardo Baldisserotto. Alkaloids, amides and antispasmodic activity of Zanthoxylum hyemale.
Planta medica.
2002 Jun; 68(6):534-8. doi:
10.1055/s-2002-32550. [PMID: 12094298] - L Puricelli, G Innocenti, G Delle Monache, R Caniato, R Filippini, E M Cappelletti. In vivo and in vitro production of alkaloids by Haplophyllum patavinum.
Natural product letters.
2002 Apr; 16(2):95-100. doi:
10.1080/10575630290019985. [PMID: 11990434] - W N Setzer, M C Setzer, J M Schmidt, D M Moriarity, B Vogler, S Reeb, A M Holmes, W A Haber. Cytotoxic components from the bark of Stauranthus perforatus from Monteverde, Costa Rica.
Planta medica.
2000 Jun; 66(5):493-4. doi:
10.1055/s-2000-8595. [PMID: 10909280] - O Schimmer, I Kühne. Mutagenic compounds in an extract from Rutae Herba (Ruta graveolens L.). II. UV-A mediated mutagenicity in the green alga Chlamydomonas reinhardtii by furoquinoline alkaloids and furocoumarins present in a commercial tincture from Rutae Herba.
Mutation research.
1990 Jan; 243(1):57-62. doi:
10.1016/0165-7992(90)90123-2. [PMID: 2300085] - J T Cheng. Effect of skimmianine on animal behavior.
Archives internationales de pharmacodynamie et de therapie.
1986 May; 281(1):35-43. doi:
". [PMID: 3753096] - H Kanamori, I Sakamoto, M Mizuta. Further study on mutagenic furoquinoline alkaloids of dictamni radicis cortex: isolation of skimmianine and high-performance liquid chromatographic analysis.
Chemical & pharmaceutical bulletin.
1986 Apr; 34(4):1826-9. doi:
10.1248/cpb.34.1826. [PMID: 3719881] - Z Q Chang, S L Wang, C Y Hao, F Liu, C F Bian, J M Chen. [Analgesic, antispastic and sedative effects of skimmianine].
Zhongguo yao li xue bao = Acta pharmacologica Sinica.
1982 Sep; 3(3):163-5. doi:
". [PMID: 6216723]