145
Views
7
CrossRef citations to date
0
Altmetric
Original Articles

Photoisomerization of 2-[3-(2-Thioxopyrrolidin-3-ylidene)methyl]-tryptophan, a Yellow Pigment in Salted Radish Roots

, , , , , , , , & show all
Pages 2262-2268 | Received 12 Feb 2008, Accepted 31 May 2008, Published online: 22 May 2014

  • 1) Ozawa, Y., Uda, Y., and Kawakishi, S., Generation of a β-carboline derivative, the yellowish precursor of processed radish roots, from 4-methylthio-3-butenyl isothiocyanate and L-tryptophan. Agric. Biol. Chem., 54, 1849–1851 (1990).
  • 2) Ozawa, Y., Uda, Y., Ohshima, T., Saito, K., and Maeda, Y., Formation of yellow pigment by the reaction of 4-methylthio-3-butenyl isothiocyanate with L-ascorbic acid and some dihydroxyphenolic compounds. Agric. Biol. Chem., 54, 605–611 (1990).
  • 3) Uda, Y., Ozawa, Y., Ohshima, T., and Kawakishi, S., Identification of enolated 2-thioxo-3-pyrrolidinecarbardehyde, a new degradation product of 4-methylthio-3-butenyl isothiocyanate. Agric. Biol. Chem., 54, 613–617 (1990).
  • 4) Uda, Y., Matsuoka, H., Shima, H., Kumagami, H., and Maeda, Y., Antimicrobial activity of water-soluble products derived from radish mustard oil and identification of an active component therein. Nippon Shokuhin Kogyo Gakkaishi (in Japanese), 40, 801–806 (1993).
  • 5) Uda, Y., Matsuoka, H., Kumagami, H., Shima, H., and Maeda, Y., Stability and antimicrobial property of 4-methylthio-3-butenyl isothiocyanate, the pungent principle in radish. Nippon Shokuhin Kogyo Gakkaishi (in Japanese), 40, 743–746 (1993).
  • 6) Uda, Y., Hayashi, H., Takahashi, A., and Shimizu, A., Mutagenic and antimutagenic property of 3-hydroxymethylene-2-thioxopyrrolidine, a major product generating from pungent principle of radish. Food Sci. Technol. Lebensm. Wiss., 33, 37–43 (2000).
  • 7) Ozawa, Y., Kawakishi, S., Uda, Y., and Maeda, Y., Isolation and identification of a novel β-carboline derivative in salted radish roots, Raphanus sativus L. Agric. Biol. Chem., 54, 1241–1245 (1990).
  • 8) Ozawa, Y., Uda, Y., and Kawakishi, S., Formation of yellow pigment containing a β-carboline skeleton in salted radish roots and its properties. Nippon Shokuhin Kogyo Gakkaishi (in Japanese), 39, 490–495 (1992).
  • 9) Oshita, I., Kanamori, H., Mizuta, M., and Sakamoto, I., A mutagenic β-carboline derivative in soy sauce. Nippon Shokuhin Kogyo Gakkaishi (in Japanese), 32, 272–277 (1991).
  • 10) Higashimoto, M., Yamamoto, T., Kinouchi, T., Matsuomoto, H., and Ohnishi, Y., Mutagenicity of 1-methyl-1,2,3,4-tetrahydro-β-carboline-3-carboxylic acid treated with nitrite in the presence of alcohols. Mutat. Res., 367, 43–49 (1996).
  • 11) Papavergou, E., and Clifford, M. N., Tetrahydro-β-carboline carboxylic acids in smoked foods. Food Addit. Contam., 9, 83–95 (1992).
  • 12) Herraiz, T., Ethyl 1-methyl-1,2,3,4-tetrahydro-β-carboline-3-carboxylate: a novel β-carboline found in alcoholic beverages. Food Chem., 66, 313–321 (1999).
  • 13) Herraiz, T., and Ough, C. S., Chemical and technological factors determining tetrahydro-β-carboline-3-carboxylic acid content in fermented alcoholic beverages. J. Agric. Food Chem., 41, 959–964 (1993).
  • 14) Matsuoka, H., Takahashi, A., Ozawa, Y., Yamada, Y., Uda, Y., and Kawakishi, S., 2-[3-(2-thioxopyrrolidin-3-ylidene)methyl]-tryptophan, a novel yellow pigment in salted radish roots. Biosci. Biotechnol. Biochem., 66, 1450–1454 (2002).
  • 15) Matsuoka, H., Takahashi, A., Yanagi, K., and Uda, Y., Antimicrobial action of 2-thioxo-3-pyrrolidinecarbardehyde, a major thiolactam compound generated from the pungent principle of radish in an aqueous medium. Food Sci. Technol. Int. Tokyo, 3, 353–356 (1997).
  • 16) Kosemura, S., Yamamura, S., and Hasegawa, K., Chemical studies on 4-methylthio-3-butenyl isothiocyanate from roots of Japanese radish (Raphanus sativus L.) in connection with raphanusanins, phototropism-regulating substance of radish hypocotyls. Tetrahedron Lett., 34, 481–484 (1993).
  • 17) Matsuoka, H., Toda, Y., Yanagi, K., Takahashi, A., Yoneyama, K., and Uda, Y., Formation of thioxopyrrolidines and dithiocarbamates from 4-methylthio-3-butenyl isothiocyanate, the pungent principle of radish, in aqueous media. Biosci. Biotechnol. Biochem., 61, 2109–2112 (1997).
  • 18) Mortensen, A., and Skibsted, L. H., “Methods in Enzymology; Oxidants and Antioxidants Part A,” ed. Packer, L., Academic Press, New York, pp. 408–421 (1999).
  • 19) Mortensen, A., and Skibsted, L. H., Free radical transients in photobleaching of xanthophylls and carotenes. Free Radic. Res., 26, 549–563 (1997).
  • 20) Mortensen, A., and Skibsted, L. H., Real time detection of reactions between radicals of lycopene and tocopherol homologues. Free Radic. Res., 27, 229–234 (1997).
  • 21) Unten, L., Koketsu, M., and Kim, M., Antidiscoloring activity of green tea polyphenols on β-carotene. J. Agric. Food Chem., 45, 2009–2012 (1997).
  • 22) Yoshida, K., Okuno, R., Kameda, K., and Kondo, T., Prevention of UV-light induced E,Z-isomerization of caffeoyl residues in the diacylated anthocyanin, gentiodelphin, by intramolecular stacking. Tetrahedron Lett., 43, 6181–6184 (2002).
  • 23) Yoshida, K., Okuno, R., Kameda, K., Mori, M., and Kondo, T., Influence of E,Z-isomerization and stability of acylated anthocyanins under the UV irradiation. Biochem. Eng. J., 14, 163–169 (2003).
  • 24) Rahn, R. O., Stefan, M. I., Bolton, J. R., Goren, E., Shaw, P. S., and Lykke, K. R., Quantum yield of the iodide-iodate chemical actinometer: dependence on wavelength and concentrations. Photochem. Photobiol., 78, 146–152 (2003).
  • 25) Kuhn, H. J., Braslavsky, S. E., and Schmidt, R., Chemical actinometry (IUPAC Technical Report). Pure Appl. Chem., 76, 2105–2146 (2004).
  • 26) Montalti, M., Credi, A., Prodi, L., and Gandolfi, M. T., “Handbook of Photochemistry” 3rd ed., CRC, New York (2006).

Reprints and Corporate Permissions

Please note: Selecting permissions does not provide access to the full text of the article, please see our help page How do I view content?

To request a reprint or corporate permissions for this article, please click on the relevant link below:

Academic Permissions

Please note: Selecting permissions does not provide access to the full text of the article, please see our help page How do I view content?

Obtain permissions instantly via Rightslink by clicking on the button below:

If you are unable to obtain permissions via Rightslink, please complete and submit this Permissions form. For more information, please visit our Permissions help page.