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Isothiocyanates and Glucosinolates from Sisymbrium officinale (L.) Scop. (“the Singers’ Plant”): Isolation and in Vitro Assays on the Somatosensory and Pain Receptor TRPA1 Channel

1
Department of Food, Environment and Nutrition-DeFENS, University of Milan, Via Celoria 2, I-20133 Milano, Italy
2
Department of Agricultural and Environmental Sciences-DISAA, University of Milan, Via Celoria 2, I-20133 Milano, Italy
3
Endocannabinoid Research Group-Institute of Biomolecular Chemistry-CNR, Pozzuoli, I-80078 Napoli, Italy
4
Epitech Group SpA, Saccolongo, 35030 Padova, Italy
*
Author to whom correspondence should be addressed.
Molecules 2019, 24(5), 949; https://doi.org/10.3390/molecules24050949
Received: 28 January 2019 / Revised: 26 February 2019 / Accepted: 7 March 2019 / Published: 8 March 2019
Sisymbrium officinale (L.) Scop. is a wild common plant of the Brassicaceae family. It is known as “the singers’ plant” for its traditional use in treating aphonia and vocal disability. Despite its wide use in herbal preparations, the molecular mechanism of action of S. officinale extracts is not known. The plant is rich in glucosinolates and isothiocyanates, which are supposed to be its active compounds. Some members of this family, in particular allylisothiocyanate, are strong agonists of the transient receptor potential ankyrin 1 (TRPA1) channel, which is involved in the somatosensory perception of pungency as well as in the nociception pathway of inflammatory pain. This study aims to isolate the glucosinolates and isothiocianates from fresh S. officinale to identify the major components and test their activity in in vitro assays with a cloned TRPA1 channel. Samples of cultivated S. officinale have been extracted and the active compounds isolated by column chromatography, HPLC and PTLC. The main components glucoputranjivin, isopropylisothiocyanate and 2-buthylisothiocianate have been tested on TRPA1. The glucosinolates glucoputranjivin and sinigrin turned out to be inactive, while isopropylisothiocyanate and 2-buthylisothiocyanate are potent agonists of TRPA1, with an EC50 in the range of the high potency natural agonists identified so far for this somatosensory channel. View Full-Text
Keywords: Sisymbrium officinale; glucosinolates; isothiocyanates; TRPA1 ion channel; somatosensory perception Sisymbrium officinale; glucosinolates; isothiocyanates; TRPA1 ion channel; somatosensory perception
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Borgonovo, G.; Zimbaldi, N.; Guarise, M.; De Nisi, P.; De Petrocellis, L.; Schiano Moriello, A.; Bassoli, A. Isothiocyanates and Glucosinolates from Sisymbrium officinale (L.) Scop. (“the Singers’ Plant”): Isolation and in Vitro Assays on the Somatosensory and Pain Receptor TRPA1 Channel. Molecules 2019, 24, 949.

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