Structural identification and bioactivities of red-violet pigments present in Basella alba fruits

Journal of Agricultural and Food Chemistry

Volumn 58, Issue 19, 2010, Pages 10364-10372

  Lin, Shu Mei ^a   Lin, Bo Hong ^a   Hsieh, Wan Mei ^a   Ko, Huey Jiun ^a   Liu, Chi Dong ^a   Chen, Lih Geeng ^a   Chiou, Robin Y Y ^a  

^a NATIONAL CHIAYI UNIVERSITY   (Taiwan)

Author keywords

Anti inflammation; Antioxidant; Basella alba L.; Betanin; Gomphrenin I

Indexed keywords

ANTI-INFLAMMATION; ANTIOXIDANT; BASELLA ALBA L.; BETANIN; GOMPHRENIN I;

EXTRACTION; FORMIC ACID; GENE EXPRESSION; IMMUNOLOGY; KETONES; METHANOL; NITRIC OXIDE; ORGANIC ACIDS; PATHOLOGY;

FRUITS;

ANTIINFLAMMATORY AGENT; ANTIOXIDANT; BETALAIN; GOMPHRENIN I; PIGMENT;

ANIMAL; ARTICLE; CHEMISTRY; DRUG EFFECT; DRUG STABILITY; FERN; FRUIT; GROWTH, DEVELOPMENT AND AGING; HEAT; MACROPHAGE; MOUSE;

ANIMALS; ANTI-INFLAMMATORY AGENTS; ANTIOXIDANTS; BETALAINS; DRUG STABILITY; FERNS; FRUIT; HOT TEMPERATURE; MACROPHAGES; MICE; PIGMENTS, BIOLOGICAL;

BASELLA ALBA; MURINAE;

EID: 78049270040     PISSN: 00218561     EISSN: 15205118     Source Type: Journal    
DOI: 10.1021/jf1017719     Document Type: Article

References (58)

1. Stintzing, F. C.; Carle, R. Functional properties of anthocyanins and betalains in plants, food, and in human nutrition. Trends Food Sci. Technol. 2004, 15, 19-38.
2. Strack, D.; Vogt, T.; Schliemann, W. Recent advances in betalain research. Phytochemistry 2003, 62, 247-269.
3. Cai, Y. Z.; Sun, M.; Corke, H. Characterization and application of betalain pigments from plants of Amaranthaceae. Trends Food Sci. Technol. 2005, 16, 370-376. (Pubitemid 41207987)
4. Tanaka, Y.; Sasaki, N.; Ohmiya, A. Biosynthesis of plant pigments: Anthocyanins, betalains and carotenoids. Plant J. 2008, 54, 733-749.
5. Moreno, D. A.; Garacía-Viguera, C.; Gil, J. I.; Gil-Izquierdo, A. Betalains in the era of global agri-food science, technology and nutritional health. Phytochem. Rev. 2008, 7, 261-280.
6. Azredo, H. M. C. Betalains: Properties, sources, applications, and stability - a review. Int. J. Food Sci. Technol. 2009, 44, 2365-2376.
7. Stafford, H. A. Review article: Anthocyanins and betalains: Evolution of the mutually exclusive pathways. Plant Sci. 1994, 101, 91-98.
8. Heuer, S.; Wray, V.; Metzger, J. W.; Strack, D. Betacyanins from flowers of Gomphrena globosa. Phytochemistry 1992, 31, 1801-1807.
9. Glassgen, W. E.; Metzger, J. W.; Heuer, S.; Strack, D. Betacyanins from fruits of Basella rubra. Phytochemistry 1993, 33, 1525-1527.
10. Cai, Y. Z.; Sun, M.; Corke, H. Identification and distribution of simple and acylated betacyanin pigments in the Amaranthaceae. J. Agric. Food Chem. 2001, 49, 1971-1978.
11. Schliemann, W.; Cai, Y. Z.; Degenkolb, T.; Schmitdt, J.; Corke, H. Betalains of Celosia argentea. Phytochemistry 2001, 58, 159-165.
12. Stintzing, F. C.; Schieber, A.; Carle, R. Betacyanins in fruits from red-purple pitaya Hylocereus polyrhizus (Weber) Britton & Rose. Food Chem. 2002, 77, 101-106.
13. Kugler, F.; Stintzinf, F. C.; Carle, R. Identification of betalains from petioles of differently colored Swiss chard (Beta vulgaris L. ssp. cicla [L.] Alef. cv. Bright Lights) by high-performance liquid chromatography- electrospray ionization mass spectrometry. J. Agric. Food Chem. 2004, 52, 2975-2981.
14. Sreekanth, D.; Arunasree, M. K.; Roy, K. R.; Chandramohan, R. T.; Reddy, G. V.; Reddanna, P. Betanin, a betacyanin pigment purified from fruits of Opuntia ficus-indica induces apoptosis in human chronic myeloid leukemia cell line-K562. Phytomedicine 2007, 14, 739-746.
15. Wybraniec, S.; Platzner, I.; Geresh, S.; Gottlieb, H. E.; Haimberg, M.; Mogilnitzki, M.; Mizrahi, Y. Betacyanins from vine cactus Hylocereus polyrhizus. Phytochemistry 2001, 58, 1209-1212.
16. Wybraniec, S.; Wydra, B. N. Mammillarinin: A new malonylated betacyanin from fruits of Mammillaria. J. Agric. Food Chem. 2007, 55, 8138-8143.
17. Santiago, E. C.; Yahia, E. M. Identification and quantification of betalains from the fruits of 10 Mexican prickly pear cultivars by highperformance liquid chromatography and electrospray ionization mass spectrometry. J. Agric. Food Chem. 2008, 56, 5758-5764.
18. Cai, Y. Z.; Corke, H. Amaranthus betacyanin pigments applied in model food systems. J. Food Sci. 1999, 64, 869-873.
19. Zhu, F.; Cai, Y.-Z.; Corke, H. Evaluation of Asian salted noodles in the presence of Amaranthus betacyanin pigments. Food Chem. 2010, 118, 663-669.
20. Kanner, K.; Harel, S.; Granit, R. Betalains - a new class of dietary cationized antioxidants. J. Agric. Food Chem. 2001, 49, 5178-5185.
21. Cai, Y. Z.; Sun, M.; Corke, H. Antioxidant activity of betalains from plants of the Amaranthaceae. J. Agric. Food Chem. 2003, 51, 2288-2294.
22. Kapadia, G. J.; Azuine, M. M.; Sridhar, R.; Okuda, Y.; Tsuruta, A.; Ichiishi, E.; Mukainake, T.; Takaski, M.; Konoshima, T.; Nishino, H.; Tokuda, H. Chemoprevention of DMBA-induced UV-promoted, NOR-1-induced TPA promoted skin carcinogenesis, and DENinduced phenobarbital promoted liver tumors in mice by extract of beetroot. Pharmacol. Res. 2003, 47, 141-148.
23. Winkler, C.; Wirleitner, B.; Schroecksnadel, K.; Schennach, H.; Fuchs, D. In vitro effects of beet root juice on stimulated and unstimulated peripheral blood mononuclears cells. Am. Biochem. Biotechnol. 2005, 1, 180-185.
24. Lu, X.; Wang, Y.; Zhang, Z. Radioprotective activity of betalains from red beets in mice exposed to gamma irradiation. Eur. J. Pharmacol. 2009, 615, 223-227.
25. Tesoriere, L.; Allegra, M.; Butera, D.; Livrea, M. A. Absorption, excretion, and distribution of dietary antioxidant betalains in LDLs: Potential health effects of betalians in humans. Am. J. Clin. Nutr. 2004, 80, 941-945.
26. Zou, D.; Brewer, M.; Garcia, F.; Feugang, J. M.; Wang, J.; Zang, R.; Liu, H.; Zou, C. Cactus pear: A natural product in cancer chemoprevention. Nutr. J. 2005, 4, 25-37.
27. Reddy, M. K.; Alexander-Lindo, R. L.; Nair, M. G. Relative inhibition of lipid peroxidation, cyclooxygenase enzymes and human tumor cell proliferation by natyral food colors. J. Agric. Food Chem. 2005, 53, 9268-9273.
28. Sreekanth, D.; Arunasree, M. K.; Rou, K. R.; Reddy, T. C.; Reddy, G. V.; Reddanna, P. Betanin a betacyanin pigment purified from fruits of Opuntia ficus-indica induces apoptosis in human chronic myeloid leukemia cell line-K562. Phytomedicine 2007, 14, 739-746.
29. Paluszczak, J.; Krajk-Kužniak, V.; Baser-Dubowska, W. The effect of dietary polyphenols on the epigenetic regulation of gene expression in MCF7 breast cancer cells. Toxicol. Lett. 2010, 195, 119-125.
30. Gentile, C.; Tesoriere, L.; Allegra, M.; Livrea, M. A.; D'Alessio, P. Antioxidant betalains from cactus pear (Opuntia ficus-indica) inhibit endothelial ICAM-1 expression. Ann. N.Y. Acad. Sci. 2004, 1028, 481-486.
31. Allegra, M.; Furtmüller, P. G.; Jantschko, W.; Zederbauer, M.; Tesoriere, L.; Livrea, M. A.; Obinger, C. Mechanism of interaction of betanin and indicaxanthin with human myeloperoxidase and hypochlorous acid. Biochem. Biophys. Res. Commun. 2005, 332, 837-844.
32. Li, H. B.; Cheng, K. W.; Wong, C. C.; Fan, K. W.; Chen, F.; Jiang, Y. Evaluation of antioxidant capacity and total phenolic content of different fractions of selected microalgae. Food Chem. 2007, 102, 771-776.
33. Shimada, K.; Fujikawa,K.; Yahara, K.; Nakamura, T. Antioxidative properties of xanthan on antioxidation of soybean oil in cyclodextran emulsion. J. Agric. Food Chem. 1992, 40, 945-948.
34. Hsu, W. C.; Cho, P. J.; Wu, M. J.; Chiou, R. Y. Y.Arapid and smallscale method for estimating antioxidative potency of peanut sprouts. J. Food Sci. 2002, 67, 2604-2608.
35. Yen, G. C.; Chen, H. Y. Antioxidant activity of various tea extracts in relation to their antimutagenicity. J. Agric. Food Chem. 1995, 43, 27-32.
36. Alley, M. C.; Scudiero, D. A.;Monks, A.; Hursey,M. L.; Czerwinski, M. J.; Fine, D. L.; Abbott, B. J.; Mayo, J. G.; Shoemaker, R. H.; Body,M.R. Feasibility of drug screeningwith panels of human tumor cell lines using a microculture tetrazolium assay. Cancer Res. 1988, 48, 589-601.
37. Scudiero, D. A.; Shoemaker, R. H.; Paull, K. D.; Monks, A.; Tierney, S.; Nofziger, T. H.; Currens, M. J.; Seniff, D.; Boyd, M. R. Evaluation of a soluble tetrazolium/formazan assay for cell growth and drug sensitivity in culture using human and other tumor cell lines. Cancer Res. 1988, 48, 4827-4833.
38. Fidder, R. M. Collaborative study of modified AOAC method of analysis for nitrite in meat and meat products. J. Assoc. Off. Anal. Chem. 1977, 60, 594-599.
39. Chen, Y.; Whetstone, H. C.; Youn, A.; Nadesan, P.; Chow, E. C.; Lin, A. C.; Alman, B. A. Beta-Catenin signaling pathway is crucial for bone morphogenetic protein 2 to induce new bone formation. J. Biol. Chem. 2007, 282, 526-533.
40. Won, J.-H.; Kim, J.-Y.; Lee, J.-H.; Back, N.-I.; Chung, H.-G.; Chung, S. A.; Jeong, T.-S.; Choi, M.-S.; Lee, K.-T. Gigantol isolated from whole plants of Cymbidium goeringii inhibits the LPS-induced iNOS and COX-2 expression via NFkB inactivation in RAW 264.7 macrophage cells. Planta Med. 2006, 72, 1181-1187.
41. Lange,R.W.;Germolec,D. C.; Foley, J. F.; Luster,M. I.Antioxidants attenuate anthralin-induced skin inflammation in BALB/c mice: Role of specific proinflammatory cytokines. J Leukoc. Biol. 1998, 64, 170-177.
42. Yang, Z. F.; Ho, D. W.; Lau, C. K.; Lam, C. T.; Lum, C. T.; Poon, R. T. P.; Fan, S. T. Allograft inflammatory factor-1(AIF-1) is crucial for the survival and pro-inflammatory activity of macrophage. Int. Immunol. 2005, 17, 1391-1397.
43. Simpson, A. E.; Tomkins, P. T.; Cooper, K. L. An investigation of the temporal induction of cytokine mRNAs in LPS-challenged thioglycollate- elicited murine peritoneal macrophages using the reverse transcription polymerase chain reaction. Inflamm. Res. 1997, 46, 65-71.
44. Wee, S. S.; Shin, Y. W.; Bae, E. A.; Kim, D. H. Effect of chunghyuldan in chronic oxazolone-induced mouse dermatitis. Biol. Pharmaceut. Bull. 2005, 28, 1070-1082.
45. Esquivel, P.; Stintzing, F. C.; Carle, R. Pigment pattern and expression of colour in fruits from different Hylocereus sp. genotypes. Innovative Food Sci. Emerging Technol. 2007, 8, 451-457.
46. Jackman, R. L.; Smith, J. L. Anthocyanins and betalains. In Natural Food Colorants; Hendry, G. A. F., Houghton, J. D., Eds.; Blackie Academic and Professional: London, U.K., 1992; Chapter 6.
47. Kundu, K. J.; Surh, Y.-J. Inflammation: Gearing the journey to cancer. Mutat. Res. 2008, 659, 15-30.
48. Libby, P. Inflammation in atherosclerosis. Nature 2002, 142, 868-874.
49. Bogdan, C. Nitric oxide and the immune response. Nat. Immunol. 2001, 2, 907-916.
50. Gentile, C.; Tesoriere, L.; Allegra, M.; Livrea, M. A.; D'Alessio, P. Antioxidant betalains from cactus pear (Opuntia ficus-indica) inhibit endothelial ICAM-1 expression. Ann. N.Y. Acad. Sci. 2004, 1028, 481-486.
51. Latz, E. The inflammasomes: Mechanisms of activation and function. Curr. Opin. Immunol. 2010, 22, 28-33.
52. Duewell, P.; Kono, H.; Rayner, K. J.; Sirois, C. M.; Vladimer, G.; Bauernfeind, F. G.; Abela, G. S.; Franchi, L.; Nuñez, G.; Schnurr, M.; Espevik, T.; Lien, E.; Fitzgerald, K. K.; Rock, K. L.; Moore, K. J.; Wright, S. D.; Hornung, V.; Latz, E. NLRP3 inflammasomes are required for atherogenesis and activated by cholesterol crystals. Nature 2010, 464, 1357-1362.
53. Zhou,R.; Tardivel,A.; Thorens, B.; Choi, I.; Tschopp, J.Thioredoxininteracting protein links oxidative stress to inflammasome activation. Nat. Immunol. 2010, 11, 136-140.
54. Martinon, F.; Burns, K.; Tschopp, J. The inflammasome: A molecular platform triggering activation of inflammatory caspases and processing of proIL-1β. Mol. Cell 2002, 10, 417-426.
55. Pítrilli, V.; Martinon, F. The inflammasome, autoinflammatory diseases, and gout. Joint Bone Spine 2007, 74, 571-576.
56. Cook, G. P.; Savic, S.; Wittmann, M.; McDermott, M. F. The NLRP3 inflammasome, a target for therapy in diverse disease states. Eur. J. Immunol. 2010, 40, 595-653.
57. Guha, M.; Mackman,K. LPS induction of gene expression in human monocytes. Cell. Signal. 2001, 13, 85-94.
58. Karin, M.; Greten, F. R. NFκB: Linking inflammation and immunity to cancer development and progression. Nat. Rev. 2005, 5, 749-759.