Skimmianine (BioDeep_00000003592)

human metabolite PANOMIX_OTCML-2023 blood metabolite Cytotoxicity

代谢物信息卡片

4,7,8-trimethoxy-furo(2,3-b)quinoline

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

3 个代谢物同义名

4,7,8-trimethoxy-furo(2,3-b)quinoline; 4,7,8-Trimethoxyfuro[2,3-b]quinoline; Skimmianine

数据库引用编号

15 个数据库交叉引用编号

ChEBI: CHEBI:9172
KEGG: C10740
PubChem: 6760
HMDB: HMDB0258333
Metlin: METLIN68540
ChEMBL: CHEMBL21396
KNApSAcK: C00002198
chemspider: 6502
CAS: 5255-76-5
CAS: 83-95-4
PMhub: MS000010156
PubChem: 12923
3DMET: B04106
NIKKAJI: J4.887I
medchemexpress: HY-N2081

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)

117 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:
9606 - Homo sapiens: -
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:

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]