Abstract
The efficient production of β-glycosides of capsaicin and 8-nordihydrocapsaicin by cultured cells of Panax ginseng is reported. Capsaicin 4-0-(6-O-β-D-xylopyranosyl)-β-D-glucopyranoside (β-prime-veroside, 12%) together with capsaicin 4-O-β-D-glucoside (6%) was isolated from the cell suspension of P. ginseng after one week of incubation with capsaicin. On the other hand, 8-nordihydrocapsaicin was glycosylated to 8-nordihydrocapsaicin 4-O-β-D-glucoside (5%) and 8-nordihydrocapsaicin 4-O-β-primeveroside (9%) by P. ginseng. Pretreatment of the cultured cells with salicylic acid greatly enhanced the glucosylation activity toward capsaicinoids. When 500 μM of salicylic acid was added to the cultures prior to the addition of substrate, capsaicin was converted into capsaicin 4-O-β-D-glucoside (17%) and capsaicin β-primeveroside (21%) and 8-nordihydrocapsaicin was glycosylated to 8-nordihydrocapsaicin 4-O-β-D-glucoside (16%) and 8-nordihydrocapsaicin β-primeveroside (15%).
Article PDF
Similar content being viewed by others
Avoid common mistakes on your manuscript.
References
Furuya, T., Ushiyama, M., Ashida, Y., Yoshikawa, T. (1989) Biotransformation of 2-phenylpropionic acid in root culture of Panax ginseng. Phytochemistry 28, 483–487.
Furuya, T., Ushiyama, M., Ashida, Y., Yoshikawa, T., Orihara, Y. (1988) Biotransformation of pheny-lacetic acid and 2-phenyl-propionic acid in suspension culture of Coffea arabica. Phytochemistry 27, 803–807.
Hamada, H., Ohiwa, S., Nshida, T., Katsuragi, H., Takeda, T., Hamada, H., Nakajima, N., Ishihara, K. (2003) One-step glucosylation of capsaicinoids by cultured cells of Phytolacca americana. Plant Biotech. 20, 253–255.
Higashiguchi, F., Nakamura, H., Hayashi, H., Kometani, T. (2006) Purification and structure determination of glucosides of capsaicin and dihydrocapsaicin from various capsicum fruits. J. Agric. Food Chem. 54, 5948–5953.
Kamel, S., Brazier, M., Desmet, G., Fliniaux, M.-A. Jacquin-Dubreuil, A. (1992) Glucosylation of butyric acid by cell suspension culture of Nicotiana plumbaginifolia. Phytochemistry 31, 1581–1583.
Kometani, T., Tanimoto, H., Nishimura, T., Kanbara, I., Okada, S. (1993) Glucosylation of capsaicin by cell suspension cultures of Coffea arabica. Biosci. Biotechnol. Biochem. 57, 2192–2193.
Kaminaga, Y., Nagatsu, A., Akiyama, T., Sugimoto, N., Yamazaki, T., Maitani, T., Mizukami, H. (2003) Production of unnatural glycosides of curcumin with drastically enhanced water solubility by cell suspension cultures of Catharanthus roseus. FEBS Lett. 555, 311–316.
Kwon, S., Shimoda, K., Hamada, H., Ishihara, K., Masuoka, N., Hamada, H. (2008) High production of β-thujaplicin glycosides by immobilized plant cells of Nicotiana tabacum. Acta Biologica Hungarica 59, 347–355.
Lewinson, E., Berman, E., Mazur, Y., Gressel, J. (1996) Glucosylation of exogenous flavanones by grapefruit (Citrus paradisi) cell cultures. Phytochemistry 25, 2531–2535.
Moyer, B. G., Gustine, D. L. (1987) Esterification of 3-nitropropanoic acid to glucose by suspension cultures of Coronilla varia. Phytochemistry 26, 139–140.
Park, K. K., Chun, K. S., Yook, J. I., Surh, Y. J. (1998) Lack of tumor promoting activity of capsaicin, a principal pungent ingredient of red peppers, in mouse skin carcinogens. Anticancer Res. 18, 4201–4205.
Surh, Y. J., Lee, S. S. (1995) Capsaicin, a double edged sword: toxicity, metabolism, and chemopre-ventative potential. Life Sci. 56, 1845–1855.
Surh, Y. J., Lee, E., Lee, J. M. (1998) Chemopreventive properties of some pungent ingredients present in red pepper and ginger. Mut. Res. 402, 259–267.
Tabata, M., Umetani, Y., Ooya, M., Tanaka, S. (1988) Glucosylation of phenolic compounds by plant cell cultures. Phytochemistry 27, 809–813.
Tani, Y., Fujioka, T., Hamada, H., Kunimatsu, M., Furuichi, Y. (2003) Favorable effects of vanillylnonanamide-[ß]-D-glucoside on serum lipids in hyperlipidemic rats. J. Jpn. Soc. Nutr. Food Sci. 56, 181–187.
Tylor, V. E., Brady, L. R., Robberts, J. E. (1981) Capsicum in Pharmacognosy. 8th ed. Lea and Febiger, Philadelphia, p. 155.
Ushiyama, M., Furuya, T. (1989) Glycosylation of phenolic compounds by root culture of Panax ginseng. Phytochemistry 28, 3009–3013.
Ushiyama, M., Asada, T., Yoshikawa, T., Furuya, T. (1989) Biotransformation of aromatic carboxylic acids by root culture of Panax ginseng. Phytochemistry 28, 1859–1869.
Upmeier, B., Thomzik, J. E., Barz, W. (1988) Nicotinic acid-N-glucoside in heterotrophic parsley cell suspension cultures. Phytochemistry 27, 3489–3493.
Ward, M. H., Lopez-Carrillo, L. (1999) Dietary factors and the risk of gastric cancer in Mexico City. Am. J. Epid. 149, 925–932.
Author information
Authors and Affiliations
Corresponding author
Rights and permissions
This article is distributed under the terms of the Creative Commons Attribution 4.0 International License (http://creativecommons.org/licenses/by/4.0/), which permits unrestricted use, distribution, and reproduction in any medium, provided you give appropriate credit to the original author(s) and the source, provide a link to the Creative Commons license, and indicate if changes were made.
About this article
Cite this article
Katsuragi, H., Shimoda, K., Ohiro, A. et al. Glycosylation of Capsaicinoids with Panax Ginseng Stimulated by Salicylic Acid. BIOLOGIA FUTURA 61, 449–456 (2010). https://doi.org/10.1556/ABiol.61.2010.4.8
Received:
Accepted:
Published:
Issue Date:
DOI: https://doi.org/10.1556/ABiol.61.2010.4.8