Glutinoin, a novel antioxidative ellagitannin from Alnus glutinosa cones with glutinoic acid dilactone moiety

Natural Product Research

Volumn 26, Issue 19, 2012, Pages 1806-1816

  Ivanov, Sergey A ^a   Nomura, Kenzo ^b   Malfanov, Ilya L ^a   Ptitsyn, Leonid R ^a  

^a Ajinomoto Genetika Research Institute   (Russian Federation)

^b Research Institute for Health Fundamentals   (Japan)

Author keywords

Alnus glutinosa; antioxidants; ellagitannins; European alder; glutinoin

Indexed keywords

ANTIOXIDANT; ASCORBIC ACID; ELLAGIC ACID; ELLAGITANNIN; GALLIC ACID; GLUTINOIN; HYDROXYL GROUP; PEDUNCULAGIN; PRAECOXIN D; UNCLASSIFIED DRUG;

ALDER; ALNUS GLUTINOSA; ANTIOXIDANT ACTIVITY; ARTICLE; DRUG CONFORMATION; DRUG ISOLATION; DRUG PURIFICATION; DRUG STRUCTURE; FRACTIONATION; HYDROLYSIS; IN VITRO STUDY; NONHUMAN; STEREOISOMERISM;

ALNUS; ANTIOXIDANTS; CHROMATOGRAPHY, HIGH PRESSURE LIQUID; DRUG EVALUATION, PRECLINICAL; HYDROLYZABLE TANNINS; MAGNETIC RESONANCE SPECTROSCOPY; MASS SPECTROMETRY; MOLECULAR STRUCTURE; PLANT EXTRACTS; PLANTS, MEDICINAL; SPECTROPHOTOMETRY, ULTRAVIOLET;

ALNUS; ALNUS GLUTINOSA; BETULACEAE;

EID: 84866525937     PISSN: 14786419     EISSN: 14786427     Source Type: Journal    
DOI: 10.1080/14786419.2011.613387     Document Type: Article

References (81)

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30. Salminen, J-P., Karonen, M., Lempa, K., Liimatainen, J., Sinkkonen, J., Lukkarinen, M., & Pihlaja, K. (2005). Characterisation of proanthocyanidin aglycones and glycosides from rose hips by high-performance liquid chromatography-mass spectrometry, and their rapid quantification together with Vitamin C. Journal of Chromatography A, 1077, 170-180. (Pubitemid 40732504)
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42. Aoki, T, Ohtaa, S, and, Suga, T. 1990. Triterpenoids, diarylheptanoids and their glycosides in theflowers of Alnus species. Phytochemistry, 29: 3611-3614.
43. Arouma, OI. 1998. Free radicals, oxidative stress and antioxidants in human health and disease. Journal of the American Oil Chemists Society, 75: 199-212.
44. Baynes, JW. 1991. The role of oxidative stress in development of complications in diabetes. Diabetes, 40: 405-412.
45. Bodeker, G, and, Hughes, MA. 1998. Wound healing, traditional treatments and research policy. In Plants for food and medicine, Edited by: Prendergast, HDV, Etkin, NL, Harris, DR and Houghton, PJ. 245-359. London: Royal Botanic Gardens Kew.
46. Buniatian, ND, Chikitkina, VV, and, Iakovleva, LV. 1998. The hepatoprotective action of ellagotannins. Eksperimental'naia i Klinicheskaia Farmakologiia (Russian), 61: 53-55.
47. Dreher, D, and, Junod, AF. 1996. Role of oxygen free radicals in cancer development. European Journal of Cancer, 32: 30-38.
48. Frédérich, M, Marcowycz, A, Cieckiewicz, E, Mégalizzi, V, Angenot, L, and, Kiss., R. 2009. Invitro anticancer potential of tree extracts from the Walloon Region forest. Planta Medica, 75: 1634-1637.
49. Fukuda, T, Ito, H, and, Yoshida, T. 2003. Antioxidative polyphenols from walnuts (Juglans regia L.). Phytochemistry, 63: 795-801. (Pubitemid 36903593)
50. Govindarajan, R, Vijayakumar, M, and, Pushpangadan, P. 2005. Antioxidant approach to disease management and the role of Rasayana herbs of ayurveda. Journal of Ethnopharmacology, 99: 165-178. (Pubitemid 40724391)
51. Gupta, RK, Al-Shafi, SMK, Layden, K, and, Haslam, E. 1982. The metabolism of gallic acid and hexahydroxydiphenic acid in plants. Part 2. Esters of (S)-hexahydroxydiphenic acid with D-glucopyranose (4C1). Journal of the Chemical Society, Perkin Translations, 1: 2525-2534.
52. Hatano, T, Edamatsu, R, Hiramatsu, M, Mori, A, Fujita, Y, Yasuhara, T, Okuda, T. 1989. Effects of the interaction of tannins with co-existing substances. VI. Effects of tannins and related polyphenols on superoxide anion radical, and on 1,1-diphenyl-2-picrylhydrazyl radical. Chemical and Pharmaceutical Bulletin, 37: 2016-2021.
53. Hatano, T, Yazaki, K, Okonogi, A, and, Okuda, T. 1991. Tannins of Stachyurus species. II. Praecoxins A, B, C and D, four new hydrolyzable tannins from Stachyurus praecox leaves. Chemical and Pharmaceutical Bulletin, 39: 1689-1693.
54. Hsu, C-Y. 2006. Antioxidant activity of extract from Polygonum aviculare. Biological Research, 39: 281-288.
55. Iakovleva, LV, and, Evdokimova, OS. 1993. Altan-new preparation for medical treatment of ulcerous disease of gastrointestinal tract. Visnik Farmacii (Ukrainian), 1-2: 96-103.
56. Inoue, KH, and, Hagerman, AE. 1988. Determination of gallotannin with rhodanine. Analytical Biochemistry, 169: 363-369.
57. Ivanov, SA, Nomura, K, Malfanov, IL, Sklyar, IV, and, Ptitsyn, LR. 2011. Isolation of a novel catechin from Bergenia rhizomes that has pronounced lipase-inhibiting and antioxidative properties. Fitoterapia, 82: 212-218.
58. Khanbabaee, K, and, Groer, M. 2003. An efficient total synthesis of pedunculagin by using a twofold intramolecular double esterification strategy. European Journal of Organic Chemistry, 2003: 2128-2131.
59. Kinsella, JE, Frankel, E, German, B, and, Kanner, J. 1993. Possible mechanisms for the protective role of antioxidants in wine and plant foods. Food Technology, 47: 85-89.
60. Kuroyanagi, M, Shimomae, M, Nagashima, Y, Muto, N, Okuda, T, Kawahara, N, Sano, T. 2005. New diarylheptanoids from Alnus japonica and their antioxidative activity. Chemical and Pharmaceutical Bulletin, 53: 1519-1523. (Pubitemid 41744475)
61. Mitchell, A, and, Wilkinson, J. 1997. Pareys Buch der Bume (The Trees of Britain and Northern Europe, 1982, 150-288. Berlin: Blackwell Wissenschafts-Verlag.
62. Nicolaou, KC, Dai, W-M, and, Guy, RK. 1994. Chemistry and biology of taxol. Angewandte Chemie International Edition (English), 33: 15-44. (Pubitemid 24986738)
63. Nomura, M, Tokoroyama, T, and, Kubota, T. 1981. Biarylheptanoids and other constituents from wood of Alnus japonica. Phytochemistry, 20: 1097-1104.
64. Nonaka, G, Tanaka, T, and, Nishioka, l. 1982. Tannins and related compounds. Part 3. A new phenolic acid, sanguisorbic acid dilactone, and three new ellagitannins, sanguiins H-1, H-2, and H-3, from Sanguisorba officinalis. Journal of the Chemical Society, Perkin Translations, 1: 1067-1073.
65. Okuda, T, Yoshida, T, Ashida, M, and, Yazaki, K. 1983. Tannins of Casuarina and Stachyurus species. Part 1. Structures of pendunculagin, casuarictin, strictinin, casuarinin, casuariin, and stachyurin. Journal of the Chemical Society, Perkin Translations, 1: 1765-1772.
66. Okuda, T, Yoshida, T, Hatano, T, and, Ito, H. 2009. Ellagitannins renewed the concept of tannins. In Chemistry and Biology of Ellagitannins, Edited by: Quideau, S. 1-54. France: World Scientific Publishing Co. Pte. Ltd.
67. Okuda, T, Yoshida, T, Kuwahara, M, Usman Memon, M, and, Shingu, T. 1984. Tannins of rosaceous medicinal plants. I: Structures of potentillin, agrimonic acids A and B, and agrimoniin, a dimeric ellagitannin. Chemical and Pharmaceutical Bulletin, 32: 2165-2173. (Pubitemid 14084191)
68. Rice-Evans, CA, Miller, NJ, Bolwell, PG, Bramley, PM, and, Pridham, JB. 1995. The relative antioxidant activities of plantderived polyphenolic flavonoids. Free Radical Research, 22: 375-383.
69. Robards, K, Prenzler, PD, Tucker, G, Swaitsitang, P, and, Glover, W. 1999. Phenolic compounds and their role in oxidative processes. Food Chemistry, 66: 401-436. (Pubitemid 29255855)
70. Salminen, J-P, Karonen, M, Lempa, K, Liimatainen, J, Sinkkonen, J, Lukkarinen, M, and, Pihlaja, K. 2005. Characterisation of proanthocyanidin aglycones and glycosides from rose hips by high-performance liquid chromatography-mass spectrometry, and their rapid quantification together with Vitamin C. Journal of Chromatography A, 1077: 170-180. (Pubitemid 40732504)
71. Schlesier, K, Harwat, M, Bhm, V, and, Bitsch, R. 2002. Assessment of antioxidant activity by using different invitro methods. Free Radical Research, 36: 177-187.
72. Schmidt, OT, and, Komarek, E. 1955. Valoneasure. XXIII. Mitteilung ber natrliche Gerbstoffe. Justus Liebigs Annalen der Chemie (German), 591: 156-176.
73. Sharma, S, Bhat, TK, and, Dawra, RK. 2000. A spectrophotometric method for assay of tannase using rhodanine. Analytical Biochemistry, 279: 85-89. (Pubitemid 30148470)
74. Sokolov, SJ, and, Zamotaev, IP. 1984. Handbook of Medicinal Plants (Russian), Moscow: Publishing House Medicina.
75. Suga, T, and, Hirata, T. 1979. New C31 secodammarane-type triterpenoids, alnuseric acid and alnuselide, in the male flowers of Alnus serrulatoides. Bulletin of the Chemical Society of Japan, 52: 1153-1155.
76. Thies, M, and, Fischer, R. 1973. Photometrische Bestimmung von Gallussaure durch Farbreaktion mit Rhodanin. Mikrochimica Acta (German), 61: 809-814.
77. Tung, NH, Kim, SK, Ra, JC, Zhao, YZ, Sohn, DH, and, Kim, YH. 2010. Antioxidative and hepatoprotective diarylheptanoids from the bark of Alnus japonica. Planta Medica, 76: 626-629.
78. Wada, H, Tachibana, H, Fuchino, H, and, Tanaka, N. 1998. Three new diarylheptanoid glycosides from Alnus japonica. Chemical and Pharmaceutical Bulletin, 46: 1054-1055. (Pubitemid 28363339)
79. Yoshida, T, Ahmed, AHF, Memon, MU, and, Okuda, T. 1993. Dimeric hydrolysable tannins from Tamarix pakistanica. Phytochemistry, 33: 197-202.
80. Yoshida, T, Amakura, Y, and, Yoshimura, M. 2010. Structural features and biological properties of ellagitannins in some plant families of the order myrtales. International Journal of Molecular Sciences, 11: 79-106.
81. 1, a hydrolysable tannin from Rosa davurica. Phytochemistry, 28: 2177-2181.