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. 2012 Dec 4;2(5):174–193. doi: 10.1007/s13659-012-0086-0

Natural hydroxyanthraquinoid pigments as potent food grade colorants: an overview

Yanis Caro 1,2,✉, Linda Anamale 1,2, Mireille Fouillaud 1,2, Philippe Laurent 2,3, Thomas Petit 2,3, Laurent Dufosse 1,2
PMCID: PMC4131637

Graphical abstract

graphic file with name 13659_2012_86_Article_Fig1_HTML.jpg

Keywords: anthraquinone, hydroxyanthraquinone, natural colorant, food colorant, microbial pigment, biotechnology, mycotoxin contamination

Footnotes

This article is published with open access at Springerlink.com

References

  • [1].Downham A., Collins P. Int. J. Food Sci. Technol. 2000;35:5–22. [Google Scholar]
  • [2].Dufossé L. Food Technol. Biotech. 2006;44:313–321. [Google Scholar]
  • [3].Räisänen R. Handbook of Natural Colorants. Chichester: John Wiley & Sons; 2009. pp. 183–200. [Google Scholar]
  • [4].Duran N., Maria F. S. T., Roseli D. C., Elisa E. Crit. Rev. Food. Sci. Nutr. 2002;42:53–66. doi: 10.1080/10408690290825457. [DOI] [PubMed] [Google Scholar]
  • [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. doi: 10.1016/j.copbio.2005.03.004. [DOI] [PubMed] [Google Scholar]
  • [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. [Google Scholar]
  • [7].Chattopadhyay P., Chatterjee S., Sen S. K. Afr. J. Biotechnol. 2008;7:2972–2985. [Google Scholar]
  • [8].Mapari S. A. S., Meyer A. S., Thrane U., Frisvad J. C. Microbial. Cell. Factories. 2009;8:24–28. doi: 10.1186/1475-2859-8-24. [DOI] [PMC free article] [PubMed] [Google Scholar]
  • [9].Blanc P. J., Loret M. O., Santerre A. L., Pareilleux A., Promé D., Promé J. C. J. Food Sci. 1995;59:862–865. doi: 10.1016/0168-1605(94)00167-5. [DOI] [PubMed] [Google Scholar]
  • [10].Hajjaj H., Blanc P. J., Groussac E., Goma G., Uribelarrea J. L., Loubiere P. Enzyme Microb. Technol. 2000;27:619–625. doi: 10.1016/s0141-0229(00)00260-x. [DOI] [PubMed] [Google Scholar]
  • [11].Carvalho J. C., Pandey A., Batitha S., Soccol C. R. Agro Food Ind Hi-tech. 2003;14:37–42. [Google Scholar]
  • [12].Liu B. H., Wu T. S., Su M. C., Chung C. P., Yu F. Y. J. Agric. Food Chem. 2005;53:170–175. doi: 10.1021/jf048878n. [DOI] [PubMed] [Google Scholar]
  • [13].Mapari S. A. S., Thrane U., Meyer A. S. Trends Biotechnol. 2010;28:300–307. doi: 10.1016/j.tibtech.2010.03.004. [DOI] [PubMed] [Google Scholar]
  • [14].Liu R., Lu Y., Wu T., Pan Y. Chromatographia. 2008;68:95–99. [Google Scholar]
  • [15].Bechtold T. Handbook of Natural Colorants. Chichester: John Wiley & Sons; 2009. pp. 151–182. [Google Scholar]
  • [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. doi: 10.3109/13880200903168031. [DOI] [PubMed] [Google Scholar]
  • [17].Bonose-Crosnier de Bellaistre M., Nowik W., Tchapla A., Heron S. J. Chromatogr. 2011;1218:778–786. doi: 10.1016/j.chroma.2010.12.032. [DOI] [PubMed] [Google Scholar]
  • [18].Bick, I. R. C.; Rhee, C. Biochem. J.1966, 98, 112–116. [DOI] [PMC free article] [PubMed]
  • [19].De Santis D., Moresi M. Ind. Crop. Prod. 2007;26:151–162. [Google Scholar]
  • [20].Baker R. A., Tatum J. H. J. Ferment. Bioeng. 1997;85:359–361. [Google Scholar]
  • [21].Nagia F. A., El-Mohamedy R. S. R. Dyes Pigments. 2007;75:550–555. [Google Scholar]
  • [22].Socaciu C. Food Colorants-Chemical and functional properties. New York: CRC Press Taylor & Francis; 2008. [Google Scholar]
  • [23].Drivas I., Blackburn R. S., Rayner C. M. Dyes Pigments. 2011;88:7–17. [Google Scholar]
  • [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. doi: 10.1046/j.1365-3156.1997.d01-242.x. [DOI] [PubMed] [Google Scholar]
  • [25].Locatelli M., Tammaro F., Menghini L., Carlucci G., Epifano F., Genovese S. Phytochem. Lett. 2009;2:223–226. doi: 10.1002/pca.1195. [DOI] [PubMed] [Google Scholar]
  • [26].Kremer D., Kosalec I., Locatelli M., Epifano F., Genovese S., Carlucci G., Zovko Koncic M. Food Chem. 2012;131:1174–1180. doi: 10.1016/j.foodchem.2012.08.026. [DOI] [PubMed] [Google Scholar]
  • [27].Muangsin N., Wisetsakdakorn W., Chaichit N., Sihanonth P., Petsom A., Sangvanich P. Dyes Pigments. 2008;77:653–656. [Google Scholar]
  • [28].Tanaka C., Miyagawa H., Kuwahara Y., Tsuda M. Mycoscience. 2002;43:317–320. [Google Scholar]
  • [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. doi: 10.1016/j.jbbm.2006.09.003. [DOI] [PubMed] [Google Scholar]
  • [30].Yadav J. P., Arya V., Panghal M., Kumar S., Dhankhar S. Fitoterapia. 2010;81:223–230. doi: 10.1016/j.fitote.2009.09.008. [DOI] [PubMed] [Google Scholar]
  • [31].Zhang L. M., Xie W. G., Wen T. T. J. Therm. Anal. Calorim. 2010;100:215–218. [Google Scholar]
  • [32].Gill M., Steglich W. Progress in the Chemistry of Organic Natural Products. New York: Springer; 1987. pp. 125–174. [Google Scholar]
  • [33].Manojlovic I., Bogdanovic-Dusanovic G., Gritsanapan W., Manojlovic N. Chem. Pap. 2006;60:466–468. [Google Scholar]
  • [34].Orban N., Boldizsar I., Szücs Z., Danos B. Dyes Pigments. 2008;77:249–257. [Google Scholar]
  • [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. [Google Scholar]
  • [36].Anke H., Kolthoum I., Zihner H., Laatsch H. Arch. Microbiol. 1980;126:223–230. doi: 10.1007/BF00409924. [DOI] [PubMed] [Google Scholar]
  • [37].Ackacha M. A., Polec-Pawlak K., Jarosz M. J. Sep. Sci. 2003;26:1028–1034. [Google Scholar]
  • [38].Banyai P., Kuzovkina I. N., Kursinszki L., Szöke E. Chromatographia. 2006;63:111–114. [Google Scholar]
  • [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. [Google Scholar]
  • [40].Bao L., Liu L., Wu Y., Han T., Xue L., Zhang Q. Chem-Biol. Interact. 2011;194:97–105. doi: 10.1016/j.cbi.2011.08.013. [DOI] [PubMed] [Google Scholar]
  • [41].Manojlovic N. T., Vasiljevic P. J., Gritsanapan W., Supabphol R., Manojlovic I. Biol. Res. 2010;43:169–176. [PubMed] [Google Scholar]
  • [42].Tanaka C., Miyagawa H., Kuwahara Y., Tsuda M. Mycoscience. 2002;43:317–320. [Google Scholar]
  • [43].Tang T., Yin L., Yang J., Shan G. Eur. J. Pharmacol. 2007;567:177–185. doi: 10.1016/j.ejphar.2007.02.033. [DOI] [PubMed] [Google Scholar]
  • [44].Schweppe H. Historic Textile and Paper Materials II. Washington: American Chemical Society; 1989. pp. 188–219. [Google Scholar]
  • [45].Rafaëlly L., Héron S., Nowik W., Tchapla A. Dyes Pigments. 2008;77:191–203. [Google Scholar]
  • [46].Mishchenko N. P., Stepanenko L. S., Krivoshchekova O. E., Maksimov O. B. Chem. Nat. Compd. 1980;16:117–121. [Google Scholar]
  • [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. [Google Scholar]
  • [48].Yamamoto Y., Matsubara H., Kinoshita Y., Kinoshita K., Koyama K., Takahashi K., Ahmadjam V., Kurokawa T., Yoshimura I. Phytochemistry. 1996;43:1239–1242. [Google Scholar]
  • [49].Gagunashvili A. N., Davidsson S. P., Jonsson Z. O., Andresson O. S. Mycol. Res. 2009;113:354–363. doi: 10.1016/j.mycres.2008.11.011. [DOI] [PubMed] [Google Scholar]
  • [50].Canamares M. V., Garcia-Ramos J. V., Domingo C., Sanchez-Cortes S. Vib. Spectrosc. 2006;40:161–167. [Google Scholar]
  • [51].Bouras N., Strelkov S. E. Physiol. Mol. Plant P. 2008;72:87–95. [Google Scholar]
  • [52].Birkinshaw J. H., Gourlay R. Biochem. J. 1961;80:387–392. doi: 10.1042/bj0800387. [DOI] [PMC free article] [PubMed] [Google Scholar]
  • [53].Miliani C., Romani A., Favaro G. J. Phys. Org. Chem. 2000;13:141–150. [Google Scholar]
  • [54].Van den Berg A. J. J., Labadie R. P. Methods in Plant Biochemistry. London: Academic press; 1989. pp. 451–491. [Google Scholar]
  • [55].Bringmann G., Gulder T. A. M., Hamm A., Goodfellow M., Fiedler H. P. Chem. Commun. 2009;44:6810–6812. doi: 10.1039/b910501h. [DOI] [PubMed] [Google Scholar]
  • [56].Leistner E. Primary and secondary metabolism of plant cell cultures. Berlin: Springer; 1985. pp. 215–224. [Google Scholar]
  • [57].Han Y. S., Van der Heijden R., Lefeber A. W. M., Erkelens C., Verpoorte R. Phytochemistry. 2002;59:45–55. doi: 10.1016/s0031-9422(01)00296-5. [DOI] [PubMed] [Google Scholar]
  • [58].Izhazi I. New Phytol. 2002;155:205–217. [Google Scholar]
  • [59].Angelini L. G., Pistelli L., Belloni P., Bertoli A., Panconesi S. Ind. Crop. Prod. 1997;6:303–311. [Google Scholar]
  • [60].Kaur P., Chandel M., Kumar S., Kumar N., Singh B., Kaur S. Food Chem. Toxicol. 2010;48:320–325. doi: 10.1016/j.fct.2009.10.019. [DOI] [PubMed] [Google Scholar]
  • [61].Morimoto M., Tanimoto K., Sakatani A., Komai K. Phytochemistry. 2002;60:163–166. doi: 10.1016/s0031-9422(02)00095-x. [DOI] [PubMed] [Google Scholar]
  • [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. doi: 10.1016/0031-9422(96)00080-5. [DOI] [PubMed] [Google Scholar]
  • [63].Banthorpe D. V., White J. J. Phytochemistry. 1995;38:107–111. [Google Scholar]
  • [64].Koyama J., Ogura T., Tagahara K. Phytochemistry. 1993;33:6, 1540–1542. [Google Scholar]
  • [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. doi: 10.1021/jf010492e. [DOI] [PubMed] [Google Scholar]
  • [66].Wijnsma R., Verpoorte R., Mulder-Krieger T., Baerheim Svendsen A. Phytochemistry. 1984;23:2307–2311. [Google Scholar]
  • [67].Robins R. I., Payne J., Rhodes M. J. C. Phytochemistry. 1986;25:2327–2334. [Google Scholar]
  • [68].Wijnsma R., Go J. T. K. A., Harkes P. A. A., Verpoorte R., Baerheim Svendsen A. Phytochemistry. 1986;25:1123–1126. [Google Scholar]
  • [69].Khouri H. E., Ibrahim R. K. Phytochemistry. 1987;26:2531–2535. [Google Scholar]
  • [70].Schripsema J., Ramos-Valdivia A., Verpoorte R. Phytochemistry. 1999;51:55–60. [Google Scholar]
  • [71].Arun P., Purushotham K. G., Jonhsy Jayarani J., Kumari V. J. Pharm. Sci. Technol. 2010;2:198–201. [Google Scholar]
  • [72].Siva R., Mayes S., Behera S. K., Rajasekaran C. Ind. Crop. Prod. 2012;37:415–419. [Google Scholar]
  • [73].Badr J. M. Nat. Prod. Sci. 2008;14:227–232. [Google Scholar]
  • [74].Liu B., Ge X., He Y., Xie J., Xu P., He Y., Zhou Q., Pan L., Chen R. Aquaculture. 2010;310:13–19. [Google Scholar]
  • [75].Li L., Zhang C., Xiao Y. Q., Chen D. D., Tian G. F., Wang Y. Chin. J. Nat. Med. 2011;9:410–413. [Google Scholar]
  • [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. doi: 10.1016/j.jplph.2009.12.007. [DOI] [PubMed] [Google Scholar]
  • [77].Baskan S., Daut-Özdemir A., Günaydin K., Erim F. B. Talanta. 2007;71:747–750. doi: 10.1016/j.talanta.2006.05.018. [DOI] [PubMed] [Google Scholar]
  • [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. [Google Scholar]
  • [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. doi: 10.1248/bpb.28.2158. [DOI] [PubMed] [Google Scholar]
  • [80].Fairbairn J. W., El-Muhtadi F. J. Phytochemistry. 1972;11:263–268. [Google Scholar]
  • [81].Genovese S., Tammaro F., Menghini L., Carlucci G., Epifano F., Locatelli M. Phytochem. Anal. 2010;21:261–267. doi: 10.1002/pca.1195. [DOI] [PubMed] [Google Scholar]
  • [82].Panichayupakaranant P., Sakunpak A., Sakunphueak A. J. Chromatogr. Sci. 2009;47:197–200. doi: 10.1093/chromsci/47.3.197. [DOI] [PubMed] [Google Scholar]
  • [83].Dagne E., Yenesew A., Asmellash S., Demissew S., Mavi S. Phytochemistry. 1994;35:401–406. [Google Scholar]
  • [84].Van Wyk B. E., Yenesew A., Dagne E. Biochem. Syst. Ecol. 1995;23:267–275. [Google Scholar]
  • [85].Mohanlall V., Steenkamp P., Odhav B. J. Med. Plants Res. 2011;5:3132–3141. [Google Scholar]
  • [86].Rosso M. L., Bertoni M. D., Adler M. T., Maier M. S. Biochem. Syst. Ecol. 2003;31:1197–1200. [Google Scholar]
  • [87].Manojlovic N., Markovic Z., Gritsanapan W., Boonpragob K. Russ. J. Phys. Chem. 2009;83:1554–1557. [Google Scholar]
  • [88].Piatelli M., Giudici de Nicola M. Phytochemistry. 1988;7:1183–1187. [Google Scholar]
  • [89].Nakano H., Komiya T., Shibata S. Phytochemistry. 1972;11:3505–3508. [Google Scholar]
  • [90].Sochting U., Fröden P. Mycol. Prog. 2002;1:257–266. [Google Scholar]
  • [91].Cohen P. A., Neil Towers G. H. Phytochemistry. 1996;42:1325–1329. [Google Scholar]
  • [92].Frisvad J. C. Arch. Environ. Contam. Toxicol. 1989;18:452–467. doi: 10.1007/BF01062373. [DOI] [PubMed] [Google Scholar]
  • [93].Mendez A., Perez C., Montanez J., Martinez G., Aguilar C. N. J. Zhejiang Univ-Sc. B. 2011;12:961–968. doi: 10.1631/jzus.B1100039. [DOI] [PMC free article] [PubMed] [Google Scholar]
  • [94].Podojil M., Sedmera P., Vokocun J., Betina V., Barathov H., Durackov K., Horakova K., Nemec P. Folia Microbiol. 1979;23:438–443. doi: 10.1007/BF02885572. [DOI] [PubMed] [Google Scholar]
  • [95].Baker R. A., Tatum J. H. J. Ferment. Bioeng. 1998;85:359–361. [Google Scholar]
  • [96].Medentsev A. G., Akimenko V. K. Phytochemistry. 1998;47:935–959. doi: 10.1016/s0031-9422(98)80053-8. [DOI] [PubMed] [Google Scholar]
  • [97].Nagia F. A., El-Mohamedy R. S. R. Dyes Pigments. 2007;75:550–555. [Google Scholar]
  • [98].Gill, M.; Morgan, P. M. ARKIVOC2001, 145–156.
  • [99].Reino J. L., Guerrero R. F. Phytochem. Rev. 2008;7:89–123. [Google Scholar]
  • [100].Vinale F., Marra R., Scala F., Ghisalberti E. L., Lorito M., Sivasithamparam K. Lett. Appl. Microbiol. 2006;43:143–148. doi: 10.1111/j.1472-765X.2006.01939.x. [DOI] [PubMed] [Google Scholar]
  • [101].Donnelly D. M. X., Helen M. S. Phytochemistry. 1986;25:2303–2304. [Google Scholar]
  • [102].Slater G. P., Haskins R. H., Hogge L. R., Nesbitt L. R. Can. J. Chem. 1967;45:92–96. [Google Scholar]
  • [103].Engström K., Brishammar S., Svensson C., Bengtsson M., Andersson R. Mycol. Res. 1993;97:381–384. [Google Scholar]
  • [104].Van Eljk G. W., Roeijmans H. J. Exp. Mycol. 1984;8:266–268. [Google Scholar]
  • [105].Cho Y. J., Park J. P., Hwang H. J., Kim S. W., Choi J. W. J. Biotechnol. 2002;95:13–23. doi: 10.1016/s0168-1656(01)00445-x. [DOI] [PubMed] [Google Scholar]
  • [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. doi: 10.1002/jobm.201000097. [DOI] [PubMed] [Google Scholar]
  • [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. [Google Scholar]
  • [108].Barbee G. C., Santer M. M., McClain W. R. Crop Prot. 2010;29:506–508. [Google Scholar]
  • [109].Kawasaki Y., Goda Y., Yoshihira K. Chem. Pharm. Bull. (Tokyo) 1992;40:1504–1509. doi: 10.1248/cpb.40.1504. [DOI] [PubMed] [Google Scholar]
  • [110].Marec F., Kollarova I., Jegorov A. Planta Med. 2001;67:127–131. doi: 10.1055/s-2001-11498. [DOI] [PubMed] [Google Scholar]
  • [111].Inoue K., Shibutani M., Masutomi N., Toyoda K., Takagi H., Uneyama C., Nishikawa A., Hirose M. Food Chem. Toxicol. 2008;46:241–252. doi: 10.1016/j.fct.2007.08.002. [DOI] [PubMed] [Google Scholar]
  • [112].Yokohira M., Yamakawa K., Hosokawa K., Matsuda Y., Kuno T., Saoo K., Imaida K. J. Food Sci. 2008;73:T26–T32. doi: 10.1111/j.1750-3841.2008.00685.x. [DOI] [PubMed] [Google Scholar]
  • [113].Kaoru I., Midori Y., Miwa T., Makoto S., Hironori T., Masao H., Akiyoshi N. Food Chem. Toxicol. 2009;47:184–191. [Google Scholar]
  • [114].Westendorf J., Marquardt H., Poginsky B., Dominiak M., Schmidt J., Marquardt H. Mutat Res. 1990;240:1–12. doi: 10.1016/0165-1218(90)90002-j. [DOI] [PubMed] [Google Scholar]
  • [115].Westendorf J., Pfau W., Schulte A. Carcinogenesis. 1998;19:2163–2168. doi: 10.1093/carcin/19.12.2163. [DOI] [PubMed] [Google Scholar]
  • [116].Marczylo T., Sugiyama C., Hayatsu H. J. Agric. Food Chem. 2003;51:3334–3337. doi: 10.1021/jf026072m. [DOI] [PubMed] [Google Scholar]
  • [117].Mueller S. O., Stopper H., Dekant W. Drug Metab. Dispos. 1998;26:540–546. [PubMed] [Google Scholar]
  • [118].Masuda T., Ueno Y. Mutat Res. 1984;125:135–144. doi: 10.1016/0027-5107(84)90065-4. [DOI] [PubMed] [Google Scholar]
  • [119].Mueller S. O., Lutz W. K., Stopper H. Mutat. Res. 1998;414:125–129. doi: 10.1016/s1383-5718(98)00047-3. [DOI] [PubMed] [Google Scholar]
  • [120].Acero S., Tabar A. I., Alvarez M. J., Garcia B. E., Olaguibel J. M., Moneo I. Allergy. 1998;53:897–901. doi: 10.1111/j.1398-9995.1998.tb03998.x. [DOI] [PubMed] [Google Scholar]
  • [121].Beaudouin E., Kanny G., Lambert H., Fremont S., Moneret-Vautrin D. Ann. Allergy Asthma Immunol. 1995;74:427–430. [PubMed] [Google Scholar]
  • [122].Baldwin J. L., Chou A. H., Solomon W. R. Ann. Allergy Asthma Immunol. 1997;79:415–419. doi: 10.1016/S1081-1206(10)63035-9. [DOI] [PubMed] [Google Scholar]
  • [123].Hanumegowda U. M., Judy B. M., Welshons W. V., Reddy C. S. Toxicol. Sci. 2002;66:159–165. doi: 10.1093/toxsci/66.1.159. [DOI] [PubMed] [Google Scholar]
  • [124].Dhulipala V. C., Maddali K. K., Welshons W. V., Reddy C. S. Birth Defects Res. B Dev. Reprod. Toxicol. 2005;74:233–242. doi: 10.1002/bdrb.20043. [DOI] [PubMed] [Google Scholar]

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