To install click the Add extension button. That's it.

The source code for the WIKI 2 extension is being checked by specialists of the Mozilla Foundation, Google, and Apple. You could also do it yourself at any point in time.

4,5
Kelly Slayton
Congratulations on this excellent venture… what a great idea!
Alexander Grigorievskiy
I use WIKI 2 every day and almost forgot how the original Wikipedia looks like.
Live Statistics
English Articles
Improved in 24 Hours
Added in 24 Hours
What we do. Every page goes through several hundred of perfecting techniques; in live mode. Quite the same Wikipedia. Just better.
.
Leo
Newton
Brights
Milds

From Wikipedia, the free encyclopedia

Spilanthol
Names
Preferred IUPAC name
(2E,6Z,8E)-N-(2-Methylpropyl)deca-2,6,8-trienamide
Other names
Affinin
Identifiers
3D model (JSmol)
ChemSpider
UNII
  • 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+
    Key: BXOCHUWSGYYSFW-HVWOQQCMSA-N
  • InChI=1/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+
    Key: BXOCHUWSGYYSFW-HVWOQQCMBC
  • O=C(/C=C/CC/C=C\C=C\C)NCC(C)C
Properties
C14H23NO
Molar mass 221.344 g·mol−1
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).

Spilanthol (Affinin) is a fatty acid amide isolated from Acmella oleracea.[1] It is believed to be responsible for the local anesthetic properties of the plant.[2]

Spilanthol permeates the human skin[3] and the inside lining of the cheeks in the mouth (buccal mucosa),[4] resulting in local as well as systemic pharmacological concentrations. In the skin and in the pancreas, spilanthol has also been shown to exert anti-inflammatory effects.[5] The underlying mechanism involves inhibition of nitric oxide production due to reduced expression of inducible nitric oxide synthase enzyme (iNOS) in macrophages. Transcription factor array experiments revealed that spilanthol inhibits the activation of several transcription factors (NFκB, ATF4, FOXO1, IRF1, ETS1, and AP-1) which may explain the effect of spilanthol on gene expression.[5]

The antihypertensive effect of Spilanthol was blocked by CB1 antagonist Rimonabant and TRPV1 antagonist Capsazepine suggesting Spilanthol mediates some activity by interaction with the cannabinoid receptors and TRPV1 channels.[6]

YouTube Encyclopedic

  • 1/3
    Views:
    19 237
    943
    1 324
  • Soxhlet extraction
  • Acmella oleracea
  • Acmella oleracea - Toothache Plant

Transcription

See also

References

  1. ^ Ramsewak, RS; Erickson, AJ; Nair, MG (1999). "Bioactive N-isobutylamides from the flower buds of Spilanthes acmella". Phytochemistry. 51 (6): 729–32. Bibcode:1999PChem..51..729R. doi:10.1016/S0031-9422(99)00101-6. PMID 10389272.
  2. ^ Spelman, Kevin; Depoix, Delphine; McCray, Megan; Mouray, Elisabeth; Grellier, Philippe (2011). "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. 25 (7): 1098–101. doi:10.1002/ptr.3395. PMC 3374932. PMID 22692989.
  3. ^ Boonen, Jente; Baert, Bram; Roche, Nathalie; Burvenich, Christian; De Spiegeleer, Bart (2010). "Transdermal behaviour of the N-alkylamide spilanthol (affinin) from Spilanthes acmella (Compositae) extracts". Journal of Ethnopharmacology. 127 (1): 77–84. doi:10.1016/j.jep.2009.09.046. PMID 19808085.
  4. ^ Boonen, Jente; Baert, Bram; Burvenich, Christian; Bondeel, Phillip; De Saeger, Sarah; De Spiegeleer, Bart (2010). "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. 53 (3): 243–249. doi:10.1016/j.jpba.2010.02.010. PMID 20227845.
  5. ^ a b Bakondi, Edina; Singh, Salam Bhopen; Hajnády, Zoltán; Nagy-Pénzes, Máté; Regdon, Zsolt; Kovács, Katalin; Hegedűs, Csaba; Madácsy, Tamara; Maléth, József; Hegyi, Péter; Demény, Máté Á (2019-09-03). "Spilanthol Inhibits Inflammatory Transcription Factors and iNOS Expression in Macrophages and Exerts Anti-inflammatory Effects in Dermatitis and Pancreatitis". International Journal of Molecular Sciences. 20 (17): E4308. doi:10.3390/ijms20174308. ISSN 1422-0067. PMC 6747447. PMID 31484391.
  6. ^ Luz-Martínez, Beatriz A.; Marrero-Morfa, Dailenys; Luna-Vázquez, Francisco J.; Rojas-Molina, Alejandra; Ibarra-Alvarado, Cesar (2024). "Affinin, isolated from Heliopsis longipes, induces an antihypertensive effect that involves CB1 cannabinoid receptors and TRPA1 and TRPV1 channels activation". Planta Medica. doi:10.1055/a-2244-8855. PMID 38219731. S2CID 266983561.


This page was last edited on 25 January 2024, at 13:47
Basis of this page is in Wikipedia. Text is available under the CC BY-SA 3.0 Unported License. Non-text media are available under their specified licenses. Wikipedia® is a registered trademark of the Wikimedia Foundation, Inc. WIKI 2 is an independent company and has no affiliation with Wikimedia Foundation.