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DOI: 10.1055/s-0039-3399933
The alkamide constituents of Zanthoxylum rhetsa (Roxb.) DC. fruits
Publication History
Publication Date:
20 December 2019 (online)
Alkamides, a class of lipophilic protoalkaloids or pseudoalkaloids, have been drawing attention of scientists due to their diverse pharmacological activities [1], [2]. Zanthoxylum species, frequently used in Asian cuisine e.g. Sichuan pepper for their tingling sensation [3], have been well documented to be a rich source of alkamides. Zanthoxylum rhetsa (Roxb.) DC., Rutaceae, originating in subtropical regions, a typical spice and “the soul” of Northern Vietnamese culinary art, is traditionally employed for treatment of inflammatory-related ailments especially toothache [4]. The target of this study was to investigate the alkamide compositions of this spice. From the dichloromethane fraction of the Z. rhetsa fruit extract, fourteen alkamides could be isolated. Two compounds, rhetsamide A and rhetsamide B, were identified as C12 fatty acid isobutylhydroxyamides. The remaining twelve compounds which comprise rhetsamide C-J, zanthoamides G-I and the known sanshool derivatives hydroxy-ζ-sanshool, hydroxy-γ-sanshool, hydroxy-γ-isosanshool, the major compounds of the investigated extract, were determined as C14 fatty acid isobutylhydroxyamides. To our knowledge, none of these compounds except for hydroxy-γ-isosanshool was previously described for this species and this is the first report of the ten new compounds, rhetsamide A-J. These results revealed that the fruits of this plant are a valuable source of new natural products as well as promising biological principles, which are worthy to be further investigated and exploited.
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References
- 1 Rios MY. Natural alkamides: pharmacology, chemistry and distribution. In Drug Discovery Research in Pharmacognosy. InTech; 2012
- 2 Boonen J, Bronselaer A, Nielandt J, Veryser L, De Tre G, De Spiegeleer B. Alkamid database: Chemistry, occurrence and functionality of plant N-alkylamides. J Ethnopharmacol 2012; 142: 563-590
- 3 Chruma JJ, Cullen DJ, Bowman L, Toy PH. Polyunsaturated fatty acid amides from the Zanthoxylum genus - from culinary curiosities to probes for chemical biology. Nat Prod Rep 2018; 35: 54-74
- 4 Quattrocchi U. CRC World Dictionary of Medicinal and Poisonous Plants: Common Names, Scientific Names, Eponyms, Synonyms, and Etymology (5 Volume Set). CRC Press; 2016
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References
- 1 Rios MY. Natural alkamides: pharmacology, chemistry and distribution. In Drug Discovery Research in Pharmacognosy. InTech; 2012
- 2 Boonen J, Bronselaer A, Nielandt J, Veryser L, De Tre G, De Spiegeleer B. Alkamid database: Chemistry, occurrence and functionality of plant N-alkylamides. J Ethnopharmacol 2012; 142: 563-590
- 3 Chruma JJ, Cullen DJ, Bowman L, Toy PH. Polyunsaturated fatty acid amides from the Zanthoxylum genus - from culinary curiosities to probes for chemical biology. Nat Prod Rep 2018; 35: 54-74
- 4 Quattrocchi U. CRC World Dictionary of Medicinal and Poisonous Plants: Common Names, Scientific Names, Eponyms, Synonyms, and Etymology (5 Volume Set). CRC Press; 2016