Spilanthol: occurrence, extraction, chemistry and biological activities

Barbosa, Alan F.; Carvalho, Mário G. de; Smith, Robert E.; Sabaa-Srur, Armando U.O.

doi:10.1016/j.bjp.2015.07.024

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Review Article • Rev. bras. farmacogn. 26 (1) • Jan-Feb 2016 • https://doi.org/10.1016/j.bjp.2015.07.024 copy

Spilanthol: occurrence, extraction, chemistry and biological activities

Authorship SCIMAGO INSTITUTIONS RANKINGS

Abstract

Spilanthol (C₁₄H₂₃NO, 221.339 g/mol) is a bioactive compound that is found in many different plants that are used as traditional remedies throughout the world. It is present in Heliopsis longipes and several species in the genus Acmella, including A. oleracea L., also known as paracress and jambu. Its leaves and flowers have sensory properties (pungency, tingling, numbing, mouth-watering) that make it a popular spice and ingredient in several Brazilian dishes. Spilanthol can exert a variety of biological and pharmacological effects including analgesic, neuroprotective, antioxidant, antimutagenic, anti-cancer, anti-inflammatory, antimicrobial, antilarvicidal and insecticidal activities. So, the aim of this review is to present a literature review on the spilanthol that describes its occurrence, chemistry, extraction and biological activities.

Keywords
Acmella oleracea; Alkamides; Bioactivity; Spilanthes oleracea L.; Heliopsis longipes

H no.	δ ¹H (ppm)	C no.	δ ¹³C (ppm)
H-2	5.79 br; d	C-1	166.0
3	6.83 dt	2	124.2
4	2.23–2.35 m	3	143.5
5	2.23–2.35 m	4	32.1
6	5.26 dt	5	26.4
7	5.97 dd	6	127.7
8	6.29 br; dd	7	129.5
9	5.70 dq	8	126.7
10	1.78 d	9	130.0
H-N	5.47 br, s	10	18.3
1′	3.15 dd	1′	46.9
2′		2′	28.6
3′	1.78 m	3′	20.1

Biological activity	Reference
Analgesic	Prachayasittukal et al. (2013)Prachayasittukal, V., Prachayasittukal, S., Ruchiwarat, S., Prachayasittukal, V., 2013. High therapeutic potential of Spilanthes acmella: a review. EXCLI J. 12, 291-312
Antinociceptive	Déciga-Campos et al. (2012)Déciga-Campos, M., Arriaga-Alba, M., Ventura-Martínez, R., Aguilar-Guadarrama, B., Rios, M.Y., 2012. Pharmacological and toxicological profile of extract from Heliopsis longipes and affinin. Drug Dev. Res. 73, 130-137
Antioxidant	Abeysiri et al. (2013)Abeysiri, G.R.P.I., Dharmadasa, R.M., Abeysinghe, D.C., Samarasinghe, K., 2013. Screening of phytochemical, physico-chemical and bioactivity of different parts of Spilantes acmella Murr. (Asteraceae), a natural remedy for toothache. Ind. Crop. Prod. 50, 852-856
Anti-inflammatory	Dias et al. (2012)Dias, A.M.A., Santos, P., Seabraa, I.J., Junior, R.N.C., Braga, M.E.M., de Sousa, H.C., 2012. Spilanthol from Spilanthes acmella flowers, leaves and stems obtained by selective supercritical carbon dioxide extraction. J. Supercrit. Fluids. 61, 62-70
Anti-wrinkle	Demarne and Passaro (2009)Demarne, F., Passaro, G., 2009. Use of an Acmella oleracea extract for the botulinum toxin-like effect thereof in an anti-wrinkle cosmetic composition. US Patent No. 7,531,193 B2.
Antifungal	Dubey et al. (2013)Dubey, S., Maity, S., Singh, M., Saraf, S.A., Saha, S., 2013. Phytochemistry, pharmacology and toxicology of Spilanthes acmella: a review. Adv. Pharmacol. Sci., Article ID 423750.
Bacteriostatic	Molina-Torres et al. (2004)Molina-Torres, J., Salazar-Cabrera, C.J., Armenta-Salinas, C., Ramírez-Sánchez, E., 2004. Fungistatic and bacteriostatic activities of alkamides from Heliopsis longipes roots: affinin and reduces amides. J. Agric. Food Chem. 52, 4700-4704
Insecticidal	Sharma et al. (2012)Sharma, A., Kumar, V., Rattan, R.S., Kumar, N., Singh, B., 2012. Insecticidal toxicity of spilanthol from Spilanthes acmella Murr. Against Plutella xylostella L. Am. J. Plant Sci. 3, 1568-1572
Antimalarial	Sharma et al. (2012)Sharma, A., Kumar, V., Rattan, R.S., Kumar, N., Singh, B., 2012. Insecticidal toxicity of spilanthol from Spilanthes acmella Murr. Against Plutella xylostella L. Am. J. Plant Sci. 3, 1568-1572
Anti-larvicidal against Aedes aegypti and Helicoverpa zea neonates	Ramsewak et al. (1999)Ramsewak, R.S., Erickson, A.J., Nair, M.G., 1999. Bioactive N-isobutylamides from the flower buds of Spilanthes Acmella . Phytochemistry. 51, 729-732
Anti-molluscicidal	Johns et al. (1982)Johns, T., Graham, K., Towers, G.H.N., 1982. Molluscicidal activity of affinin and other isobutylamides from the Asteraceae. Phytochemistry. 21, 2737-2738
Anticonvulsant	Dubey et al. (2013)Dubey, S., Maity, S., Singh, M., Saraf, S.A., Saha, S., 2013. Phytochemistry, pharmacology and toxicology of Spilanthes acmella: a review. Adv. Pharmacol. Sci., Article ID 423750.
Aphrodisiac	Dubey et al. (2013)Dubey, S., Maity, S., Singh, M., Saraf, S.A., Saha, S., 2013. Phytochemistry, pharmacology and toxicology of Spilanthes acmella: a review. Adv. Pharmacol. Sci., Article ID 423750.
Pancreatic lipase inhibitor	Dubey et al. (2013)Dubey, S., Maity, S., Singh, M., Saraf, S.A., Saha, S., 2013. Phytochemistry, pharmacology and toxicology of Spilanthes acmella: a review. Adv. Pharmacol. Sci., Article ID 423750.
Antimicrobial agent	Dubey et al. (2013)Dubey, S., Maity, S., Singh, M., Saraf, S.A., Saha, S., 2013. Phytochemistry, pharmacology and toxicology of Spilanthes acmella: a review. Adv. Pharmacol. Sci., Article ID 423750.
Diuretic	Dubey et al. (2013)Dubey, S., Maity, S., Singh, M., Saraf, S.A., Saha, S., 2013. Phytochemistry, pharmacology and toxicology of Spilanthes acmella: a review. Adv. Pharmacol. Sci., Article ID 423750.
Vasorelaxant	Dubey et al. (2013)Dubey, S., Maity, S., Singh, M., Saraf, S.A., Saha, S., 2013. Phytochemistry, pharmacology and toxicology of Spilanthes acmella: a review. Adv. Pharmacol. Sci., Article ID 423750.
Anti-human immunodeficiency virus	Dubey et al. (2013)Dubey, S., Maity, S., Singh, M., Saraf, S.A., Saha, S., 2013. Phytochemistry, pharmacology and toxicology of Spilanthes acmella: a review. Adv. Pharmacol. Sci., Article ID 423750.
Toothache relief	Dubey et al. (2013)Dubey, S., Maity, S., Singh, M., Saraf, S.A., Saha, S., 2013. Phytochemistry, pharmacology and toxicology of Spilanthes acmella: a review. Adv. Pharmacol. Sci., Article ID 423750.
Enhance skin penetration of caffeine, fortestosterone and five mycotoxins	Dubey et al. (2013)Dubey, S., Maity, S., Singh, M., Saraf, S.A., Saha, S., 2013. Phytochemistry, pharmacology and toxicology of Spilanthes acmella: a review. Adv. Pharmacol. Sci., Article ID 423750.

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[1] * Corresponding author. robert.smith05@park.edu