Review |
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Natural hydroxyanthraquinoid pigments as potent food grade colorants: an overview |
Yanis CAROa,b, Linda ANAMALEa,b, Mireille FOUILLAUDa,b, Philippe LAURENTb,c, Thomas PETITb,c, Laurent DUFOSSEab |
a Département Agroalimentaire, ESIROI, Université de La Réunion, Sainte-Clotilde, Ile de la Réunion, France; b LCSNSA, Faculté des Sciences et des Technologies, Université de La Réunion, Sainte-Clotilde, Ile de la Réunion, France; c Département Génie Biologique, IUT, Université de La Réunion, Saint-Pierre, Ile de la Réunion, France |
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Abstract Natural pigments and colorants are widely used in the world in many industries such as textile dying, food processing or cosmetic manufacturing. Among the natural products of interest are various compounds belonging to carotenoids, anthocyanins, chlorophylls, melanins, betalains… The review emphasizes pigments with anthraquinoid skeleton and gives an overview on hydroxyanthraquinoids described in Nature, the first one ever published. Trends in consumption, production and regulation of natural food grade colorants are given, in the current global market. The second part focuses on the description of the chemical structures of the main anthraquinoid colouring compounds, their properties and their biosynthetic pathways. Main natural sources of such pigments are summarized, followed by discussion about toxicity and carcinogenicity observed in some cases. As a conclusion, current industrial applications of natural hydroxyanthraquinoids are described with two examples, carminic acid from an insect and Arpink redTM from a filamentous fungus.
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Keywords
anthraquinone
hydroxyanthraquinone
natural colorant
food colorant
microbial pigment
biotechnology
mycotoxin contamination
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Issue Date: 11 February 2018
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[1] |
Downham, A.; Collins, P. Int. J. Food Sci. Technol. 2000, 35, 5-22.
|
[2] |
Dufossé, L. Food Technol. Biotech. 2006, 44, 313-321.
|
[3] |
Raisanen, R. Handbook of Natural Colorants; John Wiley & Sons:Chichester, 2009; Chapter 11, pp 183-200.
|
[4] |
Duran, N.; Maria, F. S. T.; Roseli, D. C.; Elisa, E. Crit. Rev. Food. Sci. Nutr. 2002, 42, 53-66.
|
[5] |
Mapari, S. A. S.; Nielsen, K. F.; Larsen, T. O.; Frisvad, J. C.; Meyer, A. S.; Thrane, U. Curr. Opin. Biotechnol. 2005, 16, 231-238.
|
[6] |
Dufossé, L.; Galaup, P.; Yaron, A.; Arad, S. M.; Blanc, P.; Chidambara-Murthy, K. N.; Ravishankar, G. A. Trends Food Sci. Tech. 2005, 16, 389-406.
|
[7] |
Chattopadhyay, P.; Chatterjee, S.; Sen, S. K. Afr. J. Biotechnol. 2008, 7, 2972-2985.
|
[8] |
Mapari, S. A. S.; Meyer, A. S.; Thrane, U.; Frisvad, J. C. Microbial. Cell. Factories. 2009, 8, 24-28.
|
[9] |
Blanc, P. J.; Loret, M. O.; Santerre, A. L.; Pareilleux, A.; Promé, D.; Promé, J. C. J. Food Sci. 1995, 59, 862-865.
|
[10] |
Hajjaj, H.; Blanc, P. J.; Groussac, E.; Goma, G.; Uribelarrea, J. L.; Loubiere, P. Enzyme Microb. Technol. 2000, 27, 619-625.
|
[11] |
Carvalho, J. C.; Pandey, A.; Batitha, S.; Soccol, C. R. Agro Food Ind Hi-tech. 2003, 14, 37-42.
|
[12] |
Liu, B. H.; Wu, T. S.; Su, M. C.; Chung, C. P.; Yu, F. Y. J. Agric. Food Chem. 2005, 53, 170-175.
|
[13] |
Mapari, S. A. S.; Thrane, U.; Meyer, A. S. Trends Biotechnol. 2010, 28, 300-307.
|
[14] |
Liu, R.; Lu, Y.; Wu, T.; Pan, Y. Chromatographia 2008, 68, 95-99.
|
[15] |
Bechtold, T. Handbook of Natural Colorants; John Wiley & Sons:Chichester, 2009; Chapter 10, pp 151-182.
|
[16] |
Alitheen, N. B.; Mashitoh, A. R.; Yeap, S. K.; Shuhaimi, M.; Abdul-Manaf, A.; Nordin, L. Int. Food Res. J. 2010, 17, 711-719.
|
[17] |
Bonose-Crosnier de Bellaistre, M.; Nowik, W.; Tchapla, A.; Heron, S. J. Chromatogr. 2011, 1218, 778-786.
|
[18] |
Bick, I. R. C.; Rhee, C. Biochem. J. 1966, 98, 112-116.
|
[19] |
De Santis, D.; Moresi, M. Ind. Crop. Prod. 2007, 26, 151-162.
|
[20] |
Baker, R. A.; Tatum, J. H. J. Ferment. Bioeng. 1997, 85, 359-361.
|
[21] |
Nagia, F. A.; El-Mohamedy, R. S. R. Dyes Pigments 2007, 75, 550-555.
|
[22] |
Socaciu C. Food Colorants-Chemical and functional properties; CRC Press Taylor & Francis:New York, 2008.
|
[23] |
Drivas, I.; Blackburn, R. S.; Rayner, C. M. Dyes Pigments 2011, 88, 7-17.
|
[24] |
Liu, S. Y.; Sporer, F.; Wink, M.; Jourdane, J.; Henning, R.; Li, Y. L.; Ruppel, A. Trop. Med. Int. Health 1997, 2, 179-188.
|
[25] |
Locatelli, M.; Tammaro, F.; Menghini, L.; Carlucci, G.; Epifano, F.; Genovese, S. Phytochem. Lett. 2009, 2, 223-226.
|
[26] |
Kremer, D.; Kosalec, I.; Locatelli, M.; Epifano, F.; Genovese, S.; Carlucci, G.; Zovko Koncic, M. Food Chem. 2012, 131, 1174-1180.
|
[27] |
Muangsin, N.; Wisetsakdakorn, W.; Chaichit, N.; Sihanonth, P.; Petsom, A.; Sangvanich, P. Dyes Pigments 2008, 77, 653-656.
|
[28] |
Tanaka, C.; Miyagawa, H.; Kuwahara, Y.; Tsuda, M. Mycoscience 2002, 43, 317-320.
|
[29] |
Liu, S. Y.; Lo, C. T.; Chen, C.; Liu, M. Y.; Chen, J. H.; Peng, K. C. J. Biochem. Biophys. Methods 2007, 70, 391-395.
|
[30] |
Yadav, J. P.; Arya, V.; Panghal, M.; Kumar, S.; Dhankhar, S. Fitoterapia 2010, 81, 223-230.
|
[31] |
Zhang, L. M.; Xie, W. G.; Wen, T. T. J. Therm. Anal. Calorim. 2010, 100, 215-218.
|
[32] |
Gill, M.; Steglich, W. Progress in the Chemistry of Organic Natural Products; Springer:New York, 1987; Chapter 51, pp 125-174.
|
[33] |
Manojlovic, I.; Bogdanovic-Dusanovic, G.; Gritsanapan, W.; Manojlovic, N. Chem. Pap. 2006, 60, 466-468.
|
[34] |
Orban, N.; Boldizsar, I.; Szücs, Z.; Danos, B. Dyes Pigments 2008, 77, 249-257.
|
[35] |
Smetanina, O. F.; Kalinovskii, A. I.; Khudyakova, Y. V.; Slinkina, N. N.; Pivkin, M. V.; Kuznetsova, T. A. Chem. Nat. Compd. 2007, 43, 327-329.
|
[36] |
Anke, H.; Kolthoum, I.; Zihner, H.; Laatsch, H. Arch. Microbiol. 1980, 126, 223-230.
|
[37] |
Ackacha, M. A.; Polec-Pawlak, K.; Jarosz, M. J. Sep. Sci. 2003, 26, 1028-1034.
|
[38] |
Banyai, P.; Kuzovkina, I. N.; Kursinszki, L.; Szoke, E. Chromatographia 2006, 63, 111-114.
|
[39] |
Jasril; Lajis, N. H.; Mooi, L. Y.; Abdullah, M. A.; Sukari, M. A.; Ali, A. M. Asia Pacific J. Mol. Biol. Biotechnol. 2003, 11, 3-7.
|
[40] |
Bao, L.; Liu, L.; Wu, Y.; Han, T.; Xue, L.; Zhang, Q. Chem-Biol. Interact. 2011, 194, 97-105.
|
[41] |
Manojlovic, N. T.; Vasiljevic, P. J.; Gritsanapan, W.; Supabphol, R.; Manojlovic, I. Biol. Res. 2010, 43, 169-176.
|
[42] |
Tanaka, C.; Miyagawa, H.; Kuwahara, Y.; Tsuda, M. Mycoscience 2002, 43, 317-320.
|
[43] |
Tang, T.; Yin, L.; Yang, J.; Shan, G. Eur. J. Pharmacol. 2007, 567, 177-185.
|
[44] |
Schweppe, H. Historic Textile and Paper Materials Ⅱ; American Chemical Society:Washington, 1989; Chapter 13, pp 188-219.
|
[45] |
Rafaëlly, L.; Héron, S.; Nowik, W.; Tchapla, A. Dyes Pigments 2008, 77, 191-203.
|
[46] |
Mishchenko, N. P.; Stepanenko, L. S.; Krivoshchekova, O. E.; Maksimov, O. B. Chem. Nat. Compd. 1980, 16, 117-121.
|
[47] |
Borroto, J.; Coll, J.; Rivas, M.; Blanco, M.; Concepcion, O.; Tandron, Y. A.; Hernandez, M.; Trujillo, R. Plant Cell Tiss. Org. 2008, 94, 181-187.
|
[48] |
Yamamoto, Y.; Matsubara, H.; Kinoshita, Y.; Kinoshita, K.; Koyama, K.; Takahashi, K.; Ahmadjam, V.; Kurokawa, T.; Yoshimura, I. Phytochemistry 1996, 43, 1239-1242.
|
[49] |
Gagunashvili, A. N.; Davidsson, S. P.; Jonsson, Z. O.; Andresson, O. S. Mycol. Res. 2009, 113, 354-363.
|
[50] |
Canamares, M. V.; Garcia-Ramos, J. V.; Domingo, C.; SanchezCortes, S. Vib. Spectrosc. 2006, 40, 161-167.
|
[51] |
Bouras, N.; Strelkov, S. E. Physiol. Mol. Plant P. 2008, 72, 87-95.
|
[52] |
Birkinshaw, J. H.; Gourlay, R. Biochem. J. 1961, 80, 387-392.
|
[53] |
Miliani, C.; Romani, A.; Favaro, G. J. Phys. Org. Chem. 2000, 13, 141-150.
|
[54] |
Van den Berg, A. J. J.; Labadie, R. P. Methods in Plant Biochemistry; Academic press:London, 1989; Vol. 1, pp 451-491
|
[55] |
Bringmann, G.; Gulder, T. A. M.; Hamm, A.; Goodfellow, M.; Fiedler, H. P. Chem. Commun. 2009, 44, 6810-6812.
|
[56] |
Leistner, E. Primary and secondary metabolism of plant cell cultures; Springer:Berlin, 1985; pp 215-224
|
[57] |
Han, Y. S.; Van der Heijden, R.; Lefeber, A. W. M.; Erkelens, C.; Verpoorte, R. Phytochemistry 2002, 59, 45-55.
|
[58] |
Izhazi, I. New Phytol. 2002, 155, 205-217.
|
[59] |
Angelini, L. G.; Pistelli, L.; Belloni, P.; Bertoli, A.; Panconesi, S. Ind. Crop. Prod. 1997, 6, 303-311.
|
[60] |
Kaur, P.; Chandel, M.; Kumar, S.; Kumar, N.; Singh, B.; Kaur, S. Food Chem. Toxicol. 2010, 48, 320-325.
|
[61] |
Morimoto, M.; Tanimoto, K.; Sakatani, A.; Komai, K. Phytochemistry 2002, 60, 163-166.
|
[62] |
El-Gamal, A. A.; Takeya, K.; Itokawa, H.; Halim, A. F.; Amer, M. M.; Saad, H. E. A.; Awad, S. A. Phytochemistry 1995, 40, 245-251.
|
[63] |
Banthorpe, D. V.; White, J. J. Phytochemistry 1995, 38, 107-111.
|
[64] |
Koyama, J.; Ogura, T.; Tagahara, K. Phytochemistry 1993, 33, 6, 1540-1542.
|
[65] |
Sang, S.; Cheng, X.; Zhu, N.; Stark, R. E.; Badmaev, V.; Ghai, G.; Rosen, R. T.; Ho, C. T. J. Agric. Food Chem. 2001, 49, 4478-4481.
|
[66] |
Wijnsma, R.; Verpoorte, R.; Mulder-Krieger, T.; Baerheim Svendsen, A. Phytochemistry 1984, 23, 2307-2311.
|
[67] |
Robins, R. I.; Payne, J.; Rhodes, M. J. C. Phytochemistry 1986, 25, 2327-2334.
|
[68] |
Wijnsma, R.; Go, J. T. K. A.; Harkes, P. A. A.; Verpoorte, R.; Baerheim Svendsen, A. Phytochemistry 1986, 25, 1123-1126.
|
[69] |
Khouri, H. E.; Ibrahim, R. K. Phytochemistry 1987, 26, 2531-2535.
|
[70] |
Schripsema, J.; Ramos-Valdivia, A.; Verpoorte, R. Phytochemistry 1999, 51, 55-60.
|
[71] |
Arun, P.; Purushotham, K. G.; Jonhsy Jayarani, J.; Vasantha Kumari. J. Pharm. Sci. Technol. 2010, 2, 198-201.
|
[72] |
Siva, R.; Mayes, S.; Behera, S. K.; Rajasekaran, C. Ind. Crop. Prod. 2012, 37, 415-419.
|
[73] |
Badr, J. M. Nat. Prod. Sci. 2008, 14, 227-232.
|
[74] |
Liu, B.; Ge, X.; He, Y.; Xie, J.; Xu, P; He, Y.; Zhou, Q.; Pan, L.; Chen, R. Aquaculture 2010, 310, 13-19.
|
[75] |
Li, L.; Zhang, C.; Xiao Y. Q.; Chen, D. D.; Tian, G. F.; Wang, Y. Chin. J. Nat. Med. 2011, 9, 410-413.
|
[76] |
Malik, S.; Sharma, N.; Sharma, U. K.; Singh, N. P.; Blushan, S.; Sharma, M.; Sinha, A. K.; Ahuja, P. S. J. Plant Physiol. 2010, 167, 749-756.
|
[77] |
Baskan, S.; Daut-Ozdemir, A.; Günaydin, K.; Erim, F. B. Talanta 2007, 71, 747-750.
|
[78] |
Choi, G. J.; Lee, S. W.; Jang, K. S.; Kim, J. S.; Cho, K. Y.; Kim, J. C. Crop Prot. 2004, 23, 1215-1221.
|
[79] |
Lee, N. J.; Choi, J. H.; Koo, B. S.; Ryu, S. Y.; Han, Y. H.; Lee, S. I.; Lee, D. U. Biol. Pharm. Bull. 2005, 28, 2158-2161.
|
[80] |
Fairbairn, J. W.; El-Muhtadi, F. J. Phytochemistry 1972, 11, 263-268.
|
[81] |
Genovese, S.; Tammaro, F.; Menghini, L.; Carlucci, G.; Epifano, F.; Locatelli, M. Phytochem. Anal. 2010, 21, 261-267.
|
[82] |
Panichayupakaranant, P.; Sakunpak, A.; Sakunphueak, A. J. Chromatogr. Sci. 2009, 47, 197-200.
|
[83] |
Dagne, E.; Yenesew, A.; Asmellash, S.; Demissew, S.; Mavi, S. Phytochemistry 1994, 35, 401-406.
|
[84] |
Van Wyk, B. E.; Yenesew, A.; Dagne, E. Biochem. Syst. Ecol. 1995, 23, 267-275.
|
[85] |
Mohanlall, V.; Steenkamp, P.; Odhav, B. J. Med. Plants Res. 2011, 5, 3132-3141.
|
[86] |
Rosso, M. L.; Bertoni, M. D.; Adler, M. T.; Maier, M. S. Biochem. Syst. Ecol. 2003, 31, 1197-1200.
|
[87] |
Manojlovic, N.; Markovic, Z.; Gritsanapan, W.; Boonpragob, K. Russ. J. Phys. Chem. 2009, 83, 1554-1557.
|
[88] |
Piatelli, M.; Giudici de Nicola, M. Phytochemistry 1988, 7, 1183-1187.
|
[89] |
Nakano, H.; Komiya, T.; Shibata, S. Phytochemistry 1972, 11, 3505-3508.
|
[90] |
Sochting, U.; Froden, P. Mycol. Prog. 2002, 1, 257-266.
|
[91] |
Cohen, P. A.; Neil Towers, G. H. Phytochemistry 1996, 42, 1325-1329.
|
[92] |
Frisvad, J. C. Arch. Environ. Contam. Toxicol. 1989, 18, 452-467.
|
[93] |
Mendez, A.; Perez, C.; Montanez, J.; Martinez, G.; Aguilar, C. N. J. Zhejiang Univ-Sc. B 2011, 12, 961-968.
|
[94] |
Podojil, M.; Sedmera, P.; Vokocun, J.; Betina, V.; Barathov, H.; Durackov, K.; Horakova, K.; Nemec, P. Folia Microbiol. 1979, 23, 438-443.
|
[95] |
Baker, R. A.; Tatum, J. H. J. Ferment. Bioeng. 1998, 85, 359-361.
|
[96] |
Medentsev, A. G.; Akimenko, V. K. Phytochemistry 1998, 47, 935-959.
|
[97] |
Nagia, F. A.; El-Mohamedy, R. S. R. Dyes Pigments 2007, 75, 550-555.
|
[98] |
Gill, M.; Morgan, P. M. ARKIVOC 2001, 145-156.
|
[99] |
Reino, J. L.; Guerrero, R. F. Phytochem. Rev. 2008, 7, 89-123.
|
[100] |
Vinale, F.; Marra, R.; Scala, F.; Ghisalberti, E. L.; Lorito, M.; Sivasithamparam, K. Lett. Appl. Microbiol. 2006, 43, 143-148.
|
[101] |
Donnelly, D. M. X.; Helen, M. S. Phytochemistry 1986, 25, 2303-2304.
|
[102] |
Slater, G. P.; Haskins, R. H.; Hogge, L. R.; Nesbitt, L. R. Can. J. Chem. 1967, 45, 92-96.
|
[103] |
Engstrom, K.; Brishammar, S.; Svensson, C.; Bengtsson, M.; Andersson, R. Mycol. Res. 1993, 97, 381-384.
|
[104] |
Van Eljk, G. W.; Roeijmans, H. J. Exp. Mycol. 1984, 8, 266-268.
|
[105] |
Cho, Y. J.; Park, J. P.; Hwang, H. J.; Kim, S. W.; Choi, J. W. J. Biotechnol. 2002, 95, 13-23.
|
[106] |
Velmurugan, P.; Lee, Y. H.; Nanthakumar, K.; Kamala-Kannan, S.; Dufossé, L.; Mapari, S. A. S.; Oh, B. T. J. Basic Microbiol. 2010, 50, 1-10.
|
[107] |
Wang, Y.; Chen, J. W.; Ge, L. K.; Wang, D. G.; Cai, X. Y.; Huang, L. P.; Hao, C. Dyes Pigments 2009, 83, 276-280.
|
[108] |
Barbee, G. C.; Santer, M. M.; McClain, W. R. Crop Prot. 2010, 29, 506-508.
|
[109] |
Kawasaki, Y.; Goda, Y.; Yoshihira, K. Chem. Pharm. Bull. (Tokyo) 1992, 40, 1504-1509.
|
[110] |
Marec, F.; Kollarova, I.; Jegorov, A. Planta Med. 2001, 67, 127-131.
|
[111] |
Inoue, K.; Shibutani, M.; Masutomi, N.; Toyoda, K.; Takagi, H.; Uneyama, C.; Nishikawa, A.; Hirose, M. Food Chem. Toxicol. 2008, 46, 241-252.
|
[112] |
Yokohira, M.; Yamakawa, K.; Hosokawa, K.; Matsuda, Y.; Kuno, T.; Saoo, K.; Imaida, K. J. Food Sci. 2008, 73, T26-T32.
|
[113] |
Kaoru, I.; Midori, Y.; Miwa, T.; Makoto, S.; Hironori, T.; Masao, H.; Akiyoshi, N. Food Chem. Toxicol. 2009, 47, 184-191.
|
[114] |
Westendorf, J.; Marquardt, H.; Poginsky, B.; Dominiak, M.; Schmidt, J.; Marquardt, H. Mutat Res. 1990, 240, 1-12.
|
[115] |
Westendorf, J.; Pfau, W.; Schulte, A. Carcinogenesis 1998, 19, 2163-2168.
|
[116] |
Marczylo, T.; Sugiyama, C.; Hayatsu, H. J. Agric. Food Chem. 2003, 51, 3334-3337.
|
[117] |
Mueller, S. O.; Stopper, H.; Dekant, W. Drug Metab. Dispos. 1998, 26, 540-546.
|
[118] |
Masuda, T.; Ueno, Y. Mutat Res. 1984, 125, 135-144.
|
[119] |
Mueller, S. O.; Lutz, W. K.; Stopper, H. Mutat. Res. 1998, 414, 125-129.
|
[120] |
Acero, S.; Tabar, A. I.; Alvarez, M. J.; Garcia, B. E.; Olaguibel, J. M.; Moneo, I. Allergy 1998, 53, 897-901.
|
[121] |
Beaudouin, E.; Kanny, G.; Lambert, H.; Fremont, S.; MoneretVautrin, D. Ann. Allergy Asthma Immunol. 1995, 74, 427-430.
|
[122] |
Baldwin, J. L.; Chou, A. H.; Solomon, W. R. Ann. Allergy Asthma Immunol. 1997, 79, 415-419.
|
[123] |
Hanumegowda, U. M.; Judy, B. M.; Welshons, W. V.; Reddy, C. S. Toxicol. Sci. 2002, 66, 159-165.
|
[124] |
Dhulipala, V. C.; Maddali, K. K.; Welshons, W. V.; Reddy, C. S. Birth Defects Res. B Dev. Reprod. Toxicol. 2005, 74, 233-242.
|
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