Abstract
The original red isomers and l-phenylalanine derivative isomers of monascus pigment, which have a side chain of either C5H11 or C7H15, were produced via Monascus fermentation, and then purified. The degradation patterns of the pigments relating to incubation conditions were investigated. For all tested compounds, a total of seven major fragments were formed during incubation, five in presence of sunlight irradiation and two with no sunlight. The red isomers R5 and R7 showed the same pattern whereas the L-Phe derivative isomers P5 and P7 exhibited another pattern. All of the pigments appeared to be highly sensitive to sunlight irradiation considering that with sunlight, diverse fragments were produced and the side chains C5H11 and C7H15 were degraded. The fragments are thought to be formed via degradation and combination reactions of pigments based on a comparison of the fragment molecular masses. Theoretically stable isomers of an original red pigment and some amino acid derivatives were selected based on a comparison of their Hartree conformational energies, which were estimated using geometric optimization based on ab initio molecular orbital calculations. The greater stability of amino acid derivatives was confirmed based on maximum UV-absorption wavelengths and isomer population rates.
Similar content being viewed by others
References
Carels M, Shepherd D (1977) The effect of different nitrogen sources on pigment production and sporulation of Monascus species in submerged, shaken culture. Can J Microbiol 23:1360–1372
Birch AJ, Cassera A, Fittton P, Holker JS, Smith H, Tomsor GA, Walley WB (1962) Studies in relation to biosynthesis. Part XXX. Rotation, monascin and rubropuntatin. J Chem Soc 3583–3592
Chen MH, Johns MR (1993) Effect of pH and nitrogen sources on pigment production by Monascus purpureus. Appl Microbiol Biotechnol 40:132–138
Fielding BC, Holker JSE, Jones DE, Powell ADG, Richmond KW, Robertson A, Whalley WB (1961) The chemistry of fungi. Part XXXIX. The structure of monascin. J Chem Soc 4579–4583
Manchand PS, Whalley WB, Chen FC (1973) Isolation and structure of ankaflavin. Phytochem 12:2531–2538
Hajjaj H, Klaébé A, Loret MO, Tzédakis T, Goma G, Blanc PJ (1997) Production and identification of N-glucosylrubropunctamine and N-glucosylmonascorubramine from Monascus ruber and occurrence of electron donor-acceptor complexes in these red pigments. Appl Environ Microbiol 63:2671–2678
Kuromo M, Nakanishi K, Shindo K, Tada M (1963) Biosynthesis of monascorubrin and monascoflavin. Chem Pharm Bull (Tokyo) 11:358–362
Hecht E (2002) Optics. Addison-Wesley, San Francisco, USA, pp 131–135
Hiroi T, Shima T, Isobe A, Kimura S (1975) Studies on the structure of two pigments obtained from Monascus sp. J Jpn Soc Food Nutr 28:497–502
Fowell ADG, Robertson A, Whalley WB (1956) Monascorubramin. J Chem Soc (Special Publ.) 5:27–35
Juzlova P, Martinkova L, Lozinski J, Machek F (1994) Ethanol as substrate for pigment production by the fungus Monascus purpureus. Enzyme Microb Technol 16:996–1001
Moll HR, Farr DR (1976) Red pigment and process. US Pat 3,993,789
Nakawa N, Watanabe S, Kobayashi J (1980) Nucleotide treatment of Monascus pigments to produce meat coloring agents. Japan Pat 70,09,682
Lin TF, Yakushijin K, Büchi GH, Demain AL (1992) Formation of water-soluble Monascus red pigments by biological and semi-synthetic processes. J Ind Microbiol Biotechnol 9:173–179
Jung H, Kim C, Kim K, Shin CS (2003) Color characteristics of monascus pigments derived by fermentation with various amino acids. J Agric Food Chem 51:1302–1306
Kagabu S, Akagi T (1997) Quantum chemical consideration of photostability of imidacloprid and related compounds. J Pesticide Sci 22:84–89
Jung H, Kim C, Shin CS (2005) Enhanced photo-stabilities of the monascus pigments derived with various amino acids via fermentation. J Agric Food Chem 53:7108–7114
Frisch MJ, Trucks GW, Schlegel HB, Scuseria GE, Robb MA, Cheeseman JR, Zakrzewski VG, Montgomery JA, Stratmann RE, Burant JC, Dapprich S, Millam JM, Daniels AD, Kudin KN, Strain MC, Farkas O, Tomasi J, Barone V, Cossi M, Cammi R, Mennucci B, Pomelli C, Adamo C, Clifford S, Ochterski J, Petersson GA, Ayala PA, Cui Q, Morokuma K, Salvador P, Dannenberg JJ, Malick DK, Rabuck AD, Raghavachari K, Foresman JB, Cioslowski J, Ortiz JV, Baboul AG, Stefanov BB, Liu G, Liashenko A, Piskorz P, Komaromi I, Gomperts R, Martin RL, Fox DJ, Keith T, Al-Laham MA, Peng CY, Nanayakkara A, Challacombe M, Gill PMW, Johnson BG, Chen W, Wong MW, Andres JL, Gonzalez C, Head-Gordon M, Replogle ES, Pople JA (1998) GAUSSIAN 98, Revision A.9; Gaussian, Inc., Pittsburgh, PA
Chasse GA, Mak ML, Deretey E, Farkas I, Torday LL, Papp JG, Sarma DSR, Agarwal A, Chakravarthi S, Pappc JG, Sarmad DSR, Agarwal A, Chakravarthi S, Agarwal S, Rao AV (2001) An ab Initio computational study on selected lycopene isomers. J Mol Struct (Theochem) 571:27–37
Acknowledgments
This study was supported by a grant (2009) from the National Research Foundation of Korea. We thank Prof. Gyoonhee Han for helpful discussion.
Author information
Authors and Affiliations
Corresponding author
Additional information
K.-Y. Nam is Co-first author.
Rights and permissions
About this article
Cite this article
Jung, H., Choe, D., Nam, KY. et al. Degradation patterns and stability predictions of the original reds and amino acid derivatives of monascus pigments. Eur Food Res Technol 232, 621–629 (2011). https://doi.org/10.1007/s00217-011-1427-7
Received:
Revised:
Accepted:
Published:
Issue Date:
DOI: https://doi.org/10.1007/s00217-011-1427-7