Spilanthol (BioDeep_00000257766)
代谢物信息卡片
N-ISOBUTYL-2,6,8-DECATRIENAMIDE
化学式: C14H23NO (221.178)
中文名称: 千日菊酰胺
谱图信息:
最多检出来源 () 0%
分子结构信息
SMILES: C(=C\CC/C=C/C(=O)NCC(C)C)\C=C\C
InChI: InChI=1S/C14H23NO/c1-4-5-6-7-8-9-10-11-14(16)15-12-13(2)3/h4-7,10-11,13H,8-9,12H2,1-3H3,(H,15,16)/b5-4+,7-6-,11-10+
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)
0 个相关的物种来源信息
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。
| 亚细胞结构定位 | 关联基因列表 |
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文献列表
- Mayra Suelen da S Pinheiro, Daniele A Moysés, Natasha C R Galucio, Willian Oliveira Santos, Jeferson R Souza Pina, Luana C Oliveira, Simone Yasue S Silva, Sebastião da Cruz Silva, Nilton Ferreira Frazão, Patrícia Santana B Marinho, Andrea L F Novais, André S Khayat, Andrey Moacir do Rosário Marinho. Cytotoxic and molecular evaluation of spilanthol obtained from Acmella oleracea (L.) R. K. Jansen (jambu) in human gastric cancer cells.
Natural product research.
2024 May; 38(10):1806-1811. doi:
10.1080/14786419.2023.2222220. [PMID: 37300460] - Fabian Alperth, Theresa Feistritzer, Melanie Huber, Olaf Kunert, Franz Bucar. Natural Deep Eutectic Solvents for the Extraction of Spilanthol from Acmella oleracea (L.) R.K.Jansen.
Molecules (Basel, Switzerland).
2024 Jan; 29(3):. doi:
10.3390/molecules29030612. [PMID: 38338357] - Beatriz A Luz-Martínez, Dailenys Marrero-Morfa, Francisco J Luna-Vázquez, Alejandra Rojas-Molina, Cesar Ibarra-Alvarado. Affinin, isolated from Heliopsis longipes, induces an antihypertensive effect that involves CB1 cannabinoid receptors and TRPA1 and TRPV1 channels activation.
Planta medica.
2024 Jan; ?(?):. doi:
10.1055/a-2244-8855. [PMID: 38219731] - Mirosława Grymel, Roman Mazurkiewicz, Sylwia Bajkacz, Janusz Bilik, Sławomir Kowalczyk. Extraction, Purification, Quantification, and Stability of Bioactive Spilanthol from Acmella oleracea.
Planta medica.
2023 Apr; 89(5):551-560. doi:
10.1055/a-1903-2226. [PMID: 36044910] - Maria Bellumori, Beatrice Zonfrillo, Valentina Maggini, Patrizia Bogani, Eugenia Gallo, Fabio Firenzuoli, Nadia Mulinacci, Marzia Innocenti. Acmella oleracea (L.) R.K. Jansen: Alkylamides and phenolic compounds in aerial parts and roots of in vitro seedlings.
Journal of pharmaceutical and biomedical analysis.
2022 Oct; 220(?):114991. doi:
10.1016/j.jpba.2022.114991. [PMID: 35994943] - Paola Estefanía García-Badillo, Anaguiven Avalos-Soriano, Josué López-Martínez, Teresa García-Gasca, Jesús Eduardo Castro-Ruiz. Proangiogenic Effect of Affinin and an Ethanolic Extract from Heliopsis longipes Roots: Ex Vivo and In Vivo Evidence.
Molecules (Basel, Switzerland).
2021 Dec; 26(24):. doi:
10.3390/molecules26247670. [PMID: 34946751] - Rodrigo L Fabri, Jhamine C O Freitas, Ari S O Lemos, Lara M Campos, Irley O M Diniz, Nícolas C C Pinto, Thiago P Silva, Cinthia Palazzi, Paula Marchesini, Caio Monteiro, Alan F Barbosa, Mário G Carvalho, Luciana M Chedier, Marcelo G F Araújo, Ana Carolina M Apolônio, Vinícius N Rocha, Rossana C N Melo, Priscila F Pinto. Spilanthol as a promising antifungal alkylamide for the treatment of vulvovaginal candidiasis.
Medical mycology.
2021 Dec; 59(12):1210-1224. doi:
10.1093/mmy/myab054. [PMID: 34468763] - Renan Stein, Markus Berger, Bianca Santana de Cecco, Luana Peixoto Mallmann, Paula Barros Terraciano, David Driemeier, Eliseu Rodrigues, Walter Orlando Beys-da-Silva, Eduardo Luis Konrath. Chymase inhibition: A key factor in the anti-inflammatory activity of ethanolic extracts and spilanthol isolated from Acmella oleracea.
Journal of ethnopharmacology.
2021 Apr; 270(?):113610. doi:
10.1016/j.jep.2020.113610. [PMID: 33246121] - Génesis V Buitimea-Cantúa, Elisa Magaña-Barajas, Nydia E Buitimea-Cantúa, Héctor Manuel Leija Gutiérrez, María Del Refugio Rocha-Pizaña, Ema Carina Rosas-Burgos, Alejandro Hernández-Morales, Jorge Molina-Torres. Down-regulation of aflatoxin biosynthetic genes in Aspergillus parasiticus by Heliopsis longipes roots and affinin for reduction of aflatoxin production.
Journal of environmental science and health. Part. B, Pesticides, food contaminants, and agricultural wastes.
2021; 56(10):899-908. doi:
10.1080/03601234.2021.1974273. [PMID: 34487477] - Paula Marchesini, Alan Franco Barbosa, Mirza Nalesso Gomes Sanches, Rafael Moreira do Nascimento, Francisca Leticia Vale, Rodrigo Luiz Fabri, Ralph Maturano, Mário Geraldo de Carvalho, Caio Monteiro. Acaricidal activity of Acmella oleracea (Asteraceae) extract against Rhipicephalus microplus: What is the influence of spilanthol?.
Veterinary parasitology.
2020 Jul; 283(?):109170. doi:
10.1016/j.vetpar.2020.109170. [PMID: 32580072] - G C de Souza, M D Viana, Ldm Goés, B L Sanchez-Ortiz, Ga da Silva, Wb de Souza Pinheiro, Cb Rodrigues Dos Santos, Jc Tavares Carvalho. Reproductive toxicity of the hydroethanolic extract of the flowers of Acmella oleracea and spilanthol in zebrafish: In vivo and in silico evaluation.
Human & experimental toxicology.
2020 Feb; 39(2):127-146. doi:
10.1177/0960327119878257. [PMID: 31597489] - Génesis V Buitimea-Cantúa, Nydia E Buitimea-Cantúa, María Del Refugio Rocha-Pizaña, Ema Carina Rosas-Burgos, Alejandro Hernández-Morales, Jorge Molina-Torres. Antifungal and anti-aflatoxigenic activity of Heliopsis longipes roots and affinin/spilanthol against Aspergillus parasiticus by downregulating the expression of alfD and aflR genes of the aflatoxins biosynthetic pathway.
Journal of environmental science and health. Part. B, Pesticides, food contaminants, and agricultural wastes.
2020; 55(3):210-219. doi:
10.1080/03601234.2019.1681818. [PMID: 31653182] - Edina Bakondi, Salam Bhopen Singh, Zoltán Hajnády, Máté Nagy-Pénzes, Zsolt Regdon, Katalin Kovács, Csaba Hegedűs, Tamara Madácsy, József Maléth, Péter Hegyi, Máté Á Demény, Tibor Nagy, Sándor Kéki, Éva Szabó, László Virág. Spilanthol Inhibits Inflammatory Transcription Factors and iNOS Expression in Macrophages and Exerts Anti-inflammatory Effects in Dermatitis and Pancreatitis.
International journal of molecular sciences.
2019 Sep; 20(17):. doi:
10.3390/ijms20174308. [PMID: 31484391] - Wen-Chung Huang, Hui-Ling Peng, Sindy Hu, Shu-Ju Wu. Spilanthol from Traditionally Used Spilanthes acmella Enhances AMPK and Ameliorates Obesity in Mice Fed High-Fat Diet.
Nutrients.
2019 Apr; 11(5):. doi:
10.3390/nu11050991. [PMID: 31052312] - Jiang Xu, Brian C Lewandowski, Toshio Miyazawa, Yasutaka Shoji, Karen Yee, Bruce P Bryant. Spilanthol Enhances Sensitivity to Sodium in Mouse Taste Bud Cells.
Chemical senses.
2019 01; 44(2):91-103. doi:
10.1093/chemse/bjy069. [PMID: 30364996] - Wen-Chung Huang, Ling-Yu Wu, Sindy Hu, Shu-Ju Wu. Spilanthol Inhibits COX-2 and ICAM-1 Expression via Suppression of NF-κB and MAPK Signaling in Interleukin-1β-Stimulated Human Lung Epithelial Cells.
Inflammation.
2018 Oct; 41(5):1934-1944. doi:
10.1007/s10753-018-0837-0. [PMID: 29959625] - Paula Marchesini, Alan Franco Barbosa, Cristiane Franco, Tatiane Novato, Mirza Nalesso Gomes Sanches, Mário Geraldo de Carvalho, Rodrigo Luiz Fabri, Erik Daemon, Caio Márcio Oliveira Monteiro. Activity of the extract of Acmella oleracea on immature stages of Amblyomma sculptum (Acari: Ixodidae).
Veterinary parasitology.
2018 Apr; 254(?):147-150. doi:
10.1016/j.vetpar.2018.03.009. [PMID: 29657000] - Peter Masoko. Phytochemical Analysis, Antioxidant and Antibacterial Properties of Spilanthes mauritiana Used Traditionally in Limpopo Province, South Africa.
Journal of evidence-based complementary & alternative medicine.
2017 10; 22(4):936-943. doi:
10.1177/2515690x17746774. [PMID: 29250964] - Jesús Eduardo Castro-Ruiz, Alejandra Rojas-Molina, Francisco J Luna-Vázquez, Fausto Rivero-Cruz, Teresa García-Gasca, César Ibarra-Alvarado. Affinin (Spilanthol), Isolated from Heliopsis longipes, Induces Vasodilation via Activation of Gasotransmitters and Prostacyclin Signaling Pathways.
International journal of molecular sciences.
2017 Jan; 18(1):. doi:
10.3390/ijms18010218. [PMID: 28117739] - Paula Barroso Cruz, Alan Franco Barbosa, Viviane Zeringóta, Diego Melo, Tatiane Novato, Queli Cristina Fidelis, Rodrigo Luiz Fabri, Mário Geraldo de Carvalho, Armando Ubirajara Oliveira Sabaa-Srur, Erik Daemon, Caio Márcio Oliveira Monteiro. Acaricidal activity of methanol extract of Acmella oleracea L. (Asteraceae) and spilanthol on Rhipicephalus microplus (Acari: Ixodidae) and Dermacentor nitens (Acari: Ixodidae).
Veterinary parasitology.
2016 Sep; 228(?):137-143. doi:
10.1016/j.vetpar.2016.08.026. [PMID: 27692316] - Lieselotte Veryser, Lien Taevernier, Tanmayee Joshi, Pratima Tatke, Evelien Wynendaele, Nathalie Bracke, Sofie Stalmans, Kathelijne Peremans, Christian Burvenich, Martijn Risseeuw, Bart De Spiegeleer. Mucosal and blood-brain barrier transport kinetics of the plant N-alkylamide spilanthol using in vitro and in vivo models.
BMC complementary and alternative medicine.
2016 Jun; 16(?):177. doi:
10.1186/s12906-016-1159-0. [PMID: 27296455] - Andrea Gerbino, Giorgia Schena, Serena Milano, Luigi Milella, Alan Franco Barbosa, Francesca Armentano, Giuseppe Procino, Maria Svelto, Monica Carmosino. Spilanthol from Acmella Oleracea Lowers the Intracellular Levels of cAMP Impairing NKCC2 Phosphorylation and Water Channel AQP2 Membrane Expression in Mouse Kidney.
PloS one.
2016; 11(5):e0156021. doi:
10.1371/journal.pone.0156021. [PMID: 27213818] - Verônica Santana de Freitas-Blanco, Michelle Franz-Montan, Francisco Carlos Groppo, João Ernesto de Carvalho, Glyn Mara Figueira, Luciano Serpe, Ilza Maria Oliveira Sousa, Viviane Aparecida Guilherme Damasio, Lais Thiemi Yamane, Eneida de Paula, Rodney Alexandre Ferreira Rodrigues. Development and Evaluation of a Novel Mucoadhesive Film Containing Acmella oleracea Extract for Oral Mucosa Topical Anesthesia.
PloS one.
2016; 11(9):e0162850. doi:
10.1371/journal.pone.0162850. [PMID: 27626796] - Lieselotte Veryser, Lien Taevernier, Nathalie Roche, Phillip Blondeel, Bart De Spiegeleer. Implementation of a single quad MS detector in high-throughput transdermal research of plant extracts.
Journal of pharmaceutical and biomedical analysis.
2015 Nov; 115(?):594-602. doi:
10.1016/j.jpba.2015.08.016. [PMID: 26320078] - Lionel Faure, Ronaldo Cavazos, Bibi Rafeiza Khan, Robby A Petros, Peter Koulen, Elison B Blancaflor, Kent D Chapman. Effects of synthetic alkamides on Arabidopsis fatty acid amide hydrolase activity and plant development.
Phytochemistry.
2015 Feb; 110(?):58-71. doi:
10.1016/j.phytochem.2014.11.011. [PMID: 25491532] - Myriam Arriaga-Alba, María Yolanda Rios, Myrna Déciga-Campos. Antimutagenic properties of affinin isolated from Heliopsis longipes extract.
Pharmaceutical biology.
2013 Aug; 51(8):1035-9. doi:
10.3109/13880209.2013.775161. [PMID: 23738801] - Bart De Spiegeleer, Jente Boonen, Svetlana V Malysheva, José Diana Di Mavungu, Sarah De Saeger, Nathalie Roche, Phillip Blondeel, Lien Taevernier, Lieselotte Veryser. Skin penetration enhancing properties of the plant N-alkylamide spilanthol.
Journal of ethnopharmacology.
2013 Jun; 148(1):117-25. doi:
10.1016/j.jep.2013.03.076. [PMID: 23583736] - Mithilesh Singh, Rakhi Chaturvedi. Evaluation of nutrient uptake and physical parameters on cell biomass growth and production of spilanthol in suspension cultures of Spilanthes acmella Murr.
Bioprocess and biosystems engineering.
2012 Aug; 35(6):943-51. doi:
10.1007/s00449-012-0679-3. [PMID: 22237684] - Kevin Spelman, Delphine Depoix, Megan McCray, Elisabeth Mouray, Philippe Grellier. The traditional medicine Spilanthes acmella, and the alkylamides spilanthol and undeca-2E-ene-8,10-diynoic acid isobutylamide, demonstrate in vitro and in vivo antimalarial activity.
Phytotherapy research : PTR.
2011 Jul; 25(7):1098-101. doi:
10.1002/ptr.3395. [PMID: 22692989] - Vibha Pandey, Madhu Chopra, Veena Agrawal. In vitro isolation and characterization of biolarvicidal compounds from micropropagated plants of Spilanthes acmella.
Parasitology research.
2011 Feb; 108(2):297-304. doi:
10.1007/s00436-010-2056-y. [PMID: 20859747] - J Boonen, B Baert, C Burvenich, P Blondeel, S De Saeger, B De Spiegeleer. LC-MS profiling of N-alkylamides in Spilanthes acmella extract and the transmucosal behaviour of its main bio-active spilanthol.
Journal of pharmaceutical and biomedical analysis.
2010 Nov; 53(3):243-9. doi:
10.1016/j.jpba.2010.02.010. [PMID: 20227845] - Stacy S Bae, Brandie M Ehrmann, Keivan A Ettefagh, Nadja B Cech. A validated liquid chromatography-electrospray ionization-mass spectrometry method for quantification of spilanthol in Spilanthes acmella (L.) Murr.
Phytochemical analysis : PCA.
2010 Sep; 21(5):438-43. doi:
10.1002/pca.1215. [PMID: 20310072] - Myrna Déciga-Campos, María Yolanda Rios, A Berenice Aguilar-Guadarrama. Antinociceptive effect of Heliopsis longipes extract and affinin in mice.
Planta medica.
2010 May; 76(7):665-70. doi:
10.1055/s-0029-1240658. [PMID: 19950048] - V G Cilia-López, B I Juárez-Flores, J R Aguirre-Rivera, J A Reyes-Agüero. Analgesic activity of Heliopsis longipes and its effect on the nervous system.
Pharmaceutical biology.
2010 Feb; 48(2):195-200. doi:
10.3109/13880200903078495. [PMID: 20645840] - J Boonen, B Baert, N Roche, C Burvenich, B De Spiegeleer. Transdermal behaviour of the N-alkylamide spilanthol (affinin) from Spilanthes acmella (Compositae) extracts.
Journal of ethnopharmacology.
2010 Jan; 127(1):77-84. doi:
10.1016/j.jep.2009.09.046. [PMID: 19808085] - Ivones Hernández, Lucía Márquez, Ioanna Martínez, Rodrigo Dieguez, Carla Delporte, Sylvia Prieto, Jorge Molina-Torres, Gabino Garrido. Anti-inflammatory effects of ethanolic extract and alkamides-derived from Heliopsis longipes roots.
Journal of ethnopharmacology.
2009 Jul; 124(3):649-52. doi:
10.1016/j.jep.2009.04.060. [PMID: 19439170] - Idania Rodeiro, María T Donato, Nuria Jimenez, Gabino Garrido, Jorge Molina-Torres, Roberto Menendez, José V Castell, María J Gómez-Lechón. Inhibition of human P450 enzymes by natural extracts used in traditional medicine.
Phytotherapy research : PTR.
2009 Feb; 23(2):279-82. doi:
10.1002/ptr.2613. [PMID: 18844254] - Li-Chen Wu, Nien-Chu Fan, Ming-Hui Lin, Inn-Ray Chu, Shu-Jung Huang, Ching-Yuan Hu, Shang-Yu Han. Anti-inflammatory effect of spilanthol from Spilanthes acmella on murine macrophage by down-regulating LPS-induced inflammatory mediators.
Journal of agricultural and food chemistry.
2008 Apr; 56(7):2341-9. doi:
10.1021/jf073057e. [PMID: 18321049] - María Yolanda Rios, A Berenice Aguilar-Guadarrama, María Del Carmen Gutiérrez. Analgesic activity of affinin, an alkamide from Heliopsis longipes (Compositae).
Journal of ethnopharmacology.
2007 Mar; 110(2):364-7. doi:
10.1016/j.jep.2006.09.041. [PMID: 17113736] - J P Ley, M Blings, G Krammer, G Reinders, C-O Schmidt, H-J Bertram. Isolation and synthesis of acmellonate, a new unsaturated long chain 2-ketol ester from Spilanthes acmella.
Natural product research.
2006 Jul; 20(9):798-804. doi:
10.1080/14786410500246733. [PMID: 16753916] - Jorge Molina-Torres, Carlos Junior Salazar-Cabrera, Concepción Armenta-Salinas, Enrique Ramírez-Chávez. Fungistatic and bacteriostatic activities of alkamides from Heliopsis longipes roots: affinin and reduced amides.
Journal of agricultural and food chemistry.
2004 Jul; 52(15):4700-4. doi:
10.1021/jf034374y. [PMID: 15264902]
