Planta Med 2023; 89(05): 551-560
DOI: 10.1055/a-1903-2226
Natural Product Chemistry & Analytical Studies
Original Papers

Extraction, Purification, Quantification, and Stability of Bioactive Spilanthol from Acmella oleracea

Mirosława Grymel 
1   Department of Organic Chemistry, Bioorganic Chemistry and Biotechnology, Silesian University of Technology, Gliwice, Poland
2   Department of Chemical Organic Technology and Petrochemistry, Silesian University of Technology, Gliwice, Poland
3   Biotechnology Center of Silesian University of Technology, Gliwice, Poland
,
Roman Mazurkiewicz
1   Department of Organic Chemistry, Bioorganic Chemistry and Biotechnology, Silesian University of Technology, Gliwice, Poland
,
Sylwia Bajkacz
3   Biotechnology Center of Silesian University of Technology, Gliwice, Poland
4   Department of Inorganic, Analytical Chemistry and Electrochemistry, Silesian University of Technology, Gliwice, Poland
,
Janusz Bilik
5   Melaleuca Poland Ltd., Gliwice, Poland
,
Sławomir Kowalczyk
5   Melaleuca Poland Ltd., Gliwice, Poland
› Author AffiliationsSupported by: Silesian University of Technology (Poland) Grant BK No. 04/050/BK_22/0139
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Abstract

Acmella oleracea is an ethnobotanically significant plant with a relatiwely high content of spilanthol. Due to its broad spectrum of activity, including anti-inflammatory, antioxidant, analgesic, antifungal, and bacteriostatic properties, it is considered a valuable bioactive natural product. In addition, spilanthol as its main bioactive component inhibits facial muscle contractions, making it an attractive ingredient in anti-wrinkle and anti-aging cosmetics. Due to its muscle paralyzing effects, it is called herbal botox. The commercial interest in spilanthol encourages the development of effective methods of isolating it from plant material. The methodology used in this paper allows for the obtaining of extracts from Acmella oleracea with a relatively high content of spilanthol. An effective method of spilanthol extraction from all aerial parts of Acmella oleracea as well as methods of enriching spilanthol concentration in extracts achieved by removing polar and acidic substances from crude extracts was developed. To quantify the concentration of spilanthol, a simple, fast and economically feasible quantification protocol that uses nuclear magnetic resonance (HNMR) was developed. In addition, it has been proven, that oxidation of spilanthol by air gives (2E,7Z)-6,9-endoperoxy-N-(2-methylpropyl)-2,7-decadienamide. The studies on spilanthol solutions stability were carried out and the conditions for the long-time storage of spilanthol solutions have also been developed. Additionally, for confirmation of obtained results a sensitive (LOQ=1 ng/mL), precise (RSD lower than 7%) and accurate (RE lower than 7.5%), new HPLC-MS/MS method was applied.

Key words

spilanthol - Acmella oleracea - Compositae - extraction - quantification - stability

Supporting Information

    The NMR, FTIR and MS spectra and HPLC data of spilanthol are available as Supporting Information.

  • Supporting Information


Publication History

Received: 16 January 2022

Accepted after revision: 27 June 2022

Article published online:
31 August 2022

© 2022. Thieme. All rights reserved.

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