Abstract
Five linear fatty acid amides (1–5) of the sandshool class, including two new compounds, were isolated from Zanthoxylum piperitum seeds. Based on combined spectral analyses, the structures of new compounds 4 and 5 were determined to be 2′,3′-dihydroxy-α-sanshool and 2′,3′-dihydroxy-β-sanshool, respectively. These compounds exhibited weak cytotoxicity in the A-549 (human lung cancer) cell line.
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Hashimoto, K., Satoh, K., Kase, Y., Ishige, A., Kubo, M., Sasaki, H., Nishikawa, S., Kurosawa, S., Yakabi, K., and Nakamura, T., Modulatory effect of aliphatic acid amides from Zanthoxylum piperitum on isolated gastrointestinal tract. Planta Med., 67, 179–181 (2001).
Jacobson, M., Constituents of Heliopsis Species. III. Cis-trans isomerism in affinin. J. Am. Chem. Soc., 76, 4606–4608 (1954).
Kashiwada, Y., Ito, C., Katagiri, H., Mase, I., Komatsu, K., Namba, T., and Ikeshiro, Y., Amides of the fruit Zanthoxylum spp. Phytochemistry, 44, 1125–1127 (1997).
Koo, J. Y., Jang, Y., Cho, H., Lee, C-H., Jang, K. H., Chang, Y. H., Shin, J., and Oh, U., Hydroxy-α-sanshool activates TRPV1 and TRPA1 in sensory neurons. European Journal of Neuroscience, 26, 1139–1147 (2007).
Mizutani, K., Fukunaga, Y., Tanaka, O., Takasugi, N., Saruwatari, Y.-I., Fuwa, T., Yamauchi, T., Wang, J., Jia, M.-R., Li, F.-Y., and Ling, Y.-K., Amides from huajiao, pericarps of Zanthoxylum bungeanum Maxim. Chem. Pharm. Bull., 36, 2362–2365 (1988).
Navarrete, A. and Hong, E., Anthelmintic properties of á-sanshool from Zanthoxylum liebmannianum. Planta Med., 62, 250–251 (1996).
Sugai, E., Morimitsu, Y., and Kubota, K., Quantitative analysis of sanshool compounds in Japanese pepper (Xanthoxylum piperitum DC.) and their pungent characteristics. Biosci. Biotechnol. Biochem., 69, 1958–1962 (2005).
Xiong, Q., Shi, D., Yamamoto, H., and Mizuno, M., Alkylamides from pericarps of Zanthoxylum bungeanum. Phytochemistry, 46, 1123–1126 (1997).
Yasuda, I., Takeya, K., and Itokawa, H., The geometric structure of spilanthol. Chem. Pharm. Bull., 28, 2251–2253 (1980).
Yasuda, I., Takeya, K., and Itokawa, H., Structures of amides from Asiasarum heterotropoides Maek. var. mandshuricum Maek. Chem. Pharm. Bull., 29, 564–566 (1981).
Yasuda, I., Takeya, K., and Itokawa, H., Two new pungent principles isolated from the pericarps of Zanthoxylum ailanthoides. Chem. Pharm. Bull., 29, 1791–1793 (1981).
Yasuda, I., Takeya, K., and Itokawa, H., Distribution of unsaturated aliphatic acid amides in Japanese Zanthoxylum species. Phytochemistry, 21, 1295–1298 (1982).
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Jang, K.H., Chang, Y.H., Kim, DD. et al. New polyunsaturated fatty acid amides isolated from the seeds of Zanthoxylum piperitum . Arch. Pharm. Res. 31, 569–572 (2008). https://doi.org/10.1007/s12272-001-1194-5
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DOI: https://doi.org/10.1007/s12272-001-1194-5