Picea mariana bark: A new source of trans-resveratrol and other bioactive polyphenols

Food Chemistry

Volumn 135, Issue 3, 2012, Pages 1173-1182

  García Pérez, Martha Estrella ^a,b   Royer, Mariana ^a   Herbette, Gaëtan ^c   Desjardins, Yves ^d   Pouliot, Roxane ^a,b   Stevanovic, Tatjana ^a  

^a UNIVERSITÉ LAVAL   (Canada)

^b UNIVERSITY OF QUEBEC   (Canada)

^c AIX MARSEILLE UNIVERSITY   (France)

^d LAVAL UNIVERSITY   (Canada)

Author keywords

Bark; Black spruce; Lignans; Neolignans; Picea mariana; Polyphenols; Resveratrol

Indexed keywords

BARK; BLACK SPRUCE; LIGNANS; NEOLIGNANS; PICEA MARIANA; POLYPHENOLS; RESVERATROL;

METHANOL; ORGANIC ACIDS;

PHENOLS;

2 [4 (3 HYDROXYPROPYL) 2 METHOXYPHENOXY] 1,3 PROPANEDIOL; 2,3 DIHYDRO 3 (4 HYDROXY 3 METHOXYPHENYL) 2 (HYDROXYMETHYL) 1,4 BENZODIOXIN 6 PROPANOL; ANTIINFLAMMATORY AGENT; ANTIOXIDANT; EPI TAXIFOLIN; ERYHTRO 3 METHOXY 8,4' OXYNEOLIGNAN 3',4,7,9,9' PENTOL; FLAVONOID; HOMOVANILLYL ALCOHOL; LIGNAN; NEOLIGNAN; NUTRACEUTICAL; ORCINOL; PALLASIIN; PHENOLIC ACID; PICEA MARIANA EXTRACT; POLYPHENOL; THREO 3 METHOXY 8,4' OXYNEOLIGNAN 3',4,7,9,9' PENTOL; TRANS RESVERATROL; UNCLASSIFIED DRUG;

ANTIINFLAMMATORY ACTIVITY; ANTIOXIDANT ACTIVITY; ARTICLE; BARK; BLACK SPRUCE; DRUG ISOLATION; HIGH PERFORMANCE LIQUID CHROMATOGRAPHY; MASS SPECTROMETRY; NONHUMAN; NUCLEAR MAGNETIC RESONANCE;

MOLECULAR STRUCTURE; PICEA; PLANT BARK; PLANT EXTRACTS; POLYPHENOLS; STILBENES;

PICEA; PICEA MARIANA;

EID: 84865794102     PISSN: 03088146     EISSN: 18737072     Source Type: Journal    
DOI: 10.1016/j.foodchem.2012.05.050     Document Type: Article

References (86)

1. A.A. Ahmadu, H.S. Hassan, M.U. Abubakar, and I.N. Akpulu Flavonoid glycosides from Byrsocarpus coccineus leaves. Schum and thonn (connaraceae) African Journal of Traditional Complementary and Alternative Medicines 4 3 2007 257 260 (Pubitemid 46947856)
2. M.E. Arias, J. Rodriguez, M.I. Perez, M. Hernandez, O. Polvillo, and J.A. Gonzalez-Perez Analysis of chemical changes in Picea abies wood decayed by different Streptomyces strains showing evidence for biopulping procedures Wood Science and Technology 44 2 2010 179 188
3. I.M.C. Brighente, M. Dias, L.G. Verdi, and M.G. Pizzolatti Antioxidant activity and total phenolic content of some Brazilian species Pharmaceutical Biology 45 2 2007 156 161 (Pubitemid 46426266)
4. A.H. Conner, M.A. Diehl, and J.W. Rowe Tall oil precursors and turpentine in black and white spruce Wood Science 13 2 1980 111 116
5. C. Counet, D. Callemien, and S. Collin Chocolate and cocoa: New sources of trans-resveratrol and trans-piceid Food Chemistry 98 4 2006 649 657
6. E.D. Coy, L.E. Cuca, and M. Sefkow COX, LOX and platelet aggregation inhibitory properties of Lauraceae neolignans Bioorganic & Medicinal Chemistry Letters 19 24 2009 6922 6925
7. A. Chandrasekara, and F. Shahidi Antiproliferative potential and DNA scission inhibitory activity of phenolics from whole millet grains Journal of Functional Foods 3 3 2011 159 170
8. S. Christophoridou, and P. Dais Detection and quantification of phenolic compounds in olive oil by high resolution (1)H nuclear magnetic resonance spectroscopy Analytica Chimica Acta 633 2 2009 283 292
9. H.M.L. Davies, and Q.H. Jin Intermolecular C-H activation at benzylic positions: Synthesis of (+)-imperanene and (-)-alpha-conidendrin Tetrahedron-Asymmetry 14 7 2003 941 949 (Pubitemid 36369175)
10. S. Di Micco, F. Mazue, C. Daquino, C. Spatafora, D. Delmas, and N. Latruffe Structural basis for the potential antitumour activity of DNA-interacting benzo[kl]xanthene lignans Organic & Biomolecular Chemistry 9 3 2011 701 710
11. P.N. Diouf, T. Stevanovic, and Y. Boutin The effect of extraction process on polyphenol content, triterpene composition and bioactivity of yellow birch (Betula alleghaniensis Britton) extracts Industrial Crops and Products 30 2009 297 303
12. P.N. Diouf, T. Stevanovic, and A. Cloutier Study on chemical composition, antioxidant and anti-inflammatory activities of hot water extract from Picea mariana bark and its proanthocyanidin-rich fractions Food Chemistry 113 4 2009 897 902
13. P. Eklund, R. Sillanpaa, and R. Sjoholm Synthetic transformation of hydroxymatairesinol from Norway spruce (Picea abies) to 7- hydroxysecoisolariciresinol, (+)-lariciresinol and (+)-cyclolariciresinol Journal of the Chemical Society-Perkin Transactions 1 16 2002 1906 1910 (Pubitemid 34993207)
14. R. Ekman Analysis of lignans in Norway spruce by combined gas-chromatography-mass-spectrometry Holzforschung 30 3 1976 79 85
15. European Pharmacopoeia. Fraxini folium. (2002). Strasbourg: DEQS.
16. J.M. Fang, C.K. Lee, and Y.S. Cheng Lignans from Leaves of Juniperus-Chinensis Phytochemistry 31 10 1992 3659 3661
17. M.A. Fernandez, M.T. Saenz, and M.D. Garcia Anti-inflammatory activity in rats and mice of phenolic acids isolated from Scrophularia frutescens Journal of Pharmacy and Pharmacology 50 10 1998 1183 1186 (Pubitemid 28488140)
18. K. Ferre-Filmon, L. Delaude, A. Demonceau, and A.F. Noels Stereoselective synthesis of (E)-hydroxystilbenoids by ruthenium-catalyzed cross-metathesis European Journal of Organic Chemistry 15 2005 3319 3325 (Pubitemid 41059719)
19. J. Fischer, A.J. Reynolds, L.A. Sharp, and M.S. Sherburn Radical carboxyarylation approach to lignans. Total synthesis of (-)-arctigenin, (-)-matairesinol, and related natural products Organic Letters 6 9 2004 1345 1348 (Pubitemid 38626300)
20. Y. Fukuyama, M. Nakahara, H. Minami, and M. Kodama Two new benzofuran-type lignans from the wood of Viburnum awabuki Chemical & Pharmaceutical Bulletin 44 7 1996 1418 1420 (Pubitemid 26256521)
21. H. Gao, T.F. Shupe, T.L. Eberhardt, and C.Y. Hse Antioxidant activity of extracts from the wood and bark of Port Orford cedar Journal of Wood Science 53 2 2007 147 152 (Pubitemid 46644060)
22. M.E. Garcia-Perez, M. Royer, A. Duque-Fernandez, P.N. Diouf, T. Stevanovic, and R. Pouliot Antioxidant, toxicological and antiproliferative properties of Canadian polyphenolic extracts on normal and psoriatic keratinocytes Journal of Ethnopharmacology 132 1 2010 251 258
23. M.E. García-Pérez, M. Royer, D. Rusu, P.E. Poubelle, T. Stevanovic, and R. Pouliot Black spruce polyphenols: chemical characterization and study of their effects on the IL-8 production in normal and psoriatic keratinocytes stimulated with TNF-α. Multidisciplinary approaches to modern therapeutics: joining forces for a healthier tomorrow May 24-27, 2011 Hilton Montreal Bonaventure Montreal, QC, Canada Abstracts Journal of Pharmacy and Pharmaceutical Sciences 14 3 2011 17S 190S
24. W.X. Gu, X.B. Jing, X.F. Pan, A.S.C. Chan, and T.K. Yang First asymmetric synthesis of chiral 1,4-benzodioxane lignans Tetrahedron Letters 41 32 2000 6079 6082 (Pubitemid 30620151)
25. N.R. Guz, and F.R. Stermitz Spectral comparisons of coniferyl and cinnamyl alcohol epoxide derivatives with a purported cis-epoxyconiferyl alcohol isolate Phytochemistry 54 8 2000 897 899
26. A. Hammerbacher, S.G. Ralph, J. Bohlmann, T.M. Fenning, J. Gershenzon, and A. Schmidt Biosynthesis of the major tetrahydroxystilbenes in spruce, astringin and isorhapontin, proceeds via resveratrol and is enhanced by fungal infection Plant Physiology 157 2 2011 876 890
27. C.S. Harris, J. Lambert, A. Saleem, J. Coonishish, L.C. Martineau, and A. Cuerrier Antidiabetic activity of extracts from needle, bark, and cone of Picea glauca: Organ-specific protection from glucose toxicity and glucose deprivation Pharmaceutical Biology 46 1-2 2008 126 134 (Pubitemid 351196230)
28. S.Z. Ivanova, S.A. Medvedeva, V.I. Lutskii, N.A. Tyukavkina, and N.D. Zelenikina Flavonoids of the needles of Picea ajanensis Chemistry of Natural Products 11 6 1975 817 818
29. E. Joubert, P. Winterton, T.J. Britz, and W.C.A. Gelderblom Antioxidant and pro-oxidant activities of aqueous extracts and crude polyphenolic fractions of rooibos (Aspalathus linearis) Journal of Agricultural and Food Chemistry 53 26 2005 10260 10267 (Pubitemid 43081245)
30. H. Kalantari, and D.K. Das Physiological effects of resveratrol Biofactors 36 5 2010 401 406
31. N.J. Kang, S.H. Shin, H.J. Lee, and K.W. Lee Polyphenols as small molecular inhibitors of signaling cascades in carcinogenesis Pharmacology and Therapeutics 130 3 2011 310 324
32. E. Kiehlmann, and E.P.M. Li Isomerization of dihydroquercetin Journal of Natural Products-Lloydia 58 3 1995 450 455
33. T.H. Kim, H. Ito, K. Hayashi, T. Hasegawa, T. Machiguchi, and T. Yoshida Aromatic constituents from the heartwood of Santalum album L Chemical & Pharmaceutical Bulletin 53 6 2005 641 644 (Pubitemid 40880256)
34. Y. Kinouchi, H. Ohtsu, H. Tokuda, H. Nishino, S. Matsunaga, and R. Tanaka Potential antitumor-promoting diterpenoids from the stem bark of Picea glehni Journal of Natural Products 63 6 2000 817 820 (Pubitemid 30452179)
35. I. Kouno, Y. Yanagida, S. Shimono, M. Shintomi, and C.S. Yang Phenylpropanoids from the barks of Illicium-difengpi Chemical & Pharmaceutical Bulletin 40 9 1992 2461 2464
36. S. Larsson, E. Palmqvist, B. Hahn-Hagerdal, C. Tengborg, K. Stenberg, and G. Zacchi The generation of fermentation inhibitors during dilute acid hydrolysis of softwood Enzyme and Microbial Technology 24 3-4 1999 151 159 (Pubitemid 29056189)
37. D. Lee, K.P.L. Bhat, H.H.S. Fong, N.R. Farnsworth, J.M. Pezzuto, and A.D. Kinghorn Aromatase inhibitors from Broussonetia papyrifera Journal of Natural Products 64 10 2001 1286 1293 (Pubitemid 33029208)
38. E.H. Lee, H.J. Kim, Y.S. Song, C.B. Jin, K.T. Lee, and J.S. Cho Constituents of the stems and fruits of Opuntia ficus-indica var. saboten Archives of Pharmacal Research 26 12 2003 1018 1023
39. V.G. Leont'eva, L.D. Modonova, and N.A. Tyukavkina Lignans from the wood of Picea koraiensis Chemistry of Natural Products 10 3 1974 399 400
40. B. Lindberg Epi-pinoresinol Acta Chemica Scandinavica 4 1950 391 392
41. L.N. Lundgren, and O. Theander The constituents of conifer needles. 14. cis-dihydroquercetin and trans-dihydroquercetin glucosides from needles of Pinus-sylvestris Phytochemistry 27 3 1988 829 832
42. G.D. Manners, and E.P. Swan Stilbenes in barks of 5 canadian Picea species Phytochemistry 10 3 1971 607 610
43. Marques-de Oliveira, A., dos Santos-Humberto, M. M. S., da Silva, J. M., Almeida-Rocha, R. F., & Goulart-Sant'Ana, A. E. (2006). Phytochemical studies of the extracts of stem bark and leaves of Eugenia malaccensis L. (Myrtaceae) and evaluation of their molluscicidal and larvicidal activities. Brazilian Journal of Pharmacognosy, 16(1), 618-624.
44. N. Matsuda, and M. Kikuchi Studies on the constituents of Lonicera species. 10. Neolignan glycosides from the leaves of Lonicera gracilipes var glandulosa Maxim Chemical & Pharmaceutical Bulletin 44 9 1996 1676 1679 (Pubitemid 26342281)
45. J. Mattinen, R. Sjoholm, and R. Ekman NMR-spectroscopic study of hydroxymatairesinol, the major lignan in Norway spruce (Picea abies) heartwood Ach-Models in Chemistry 135 4 1998 583 590 (Pubitemid 128771672)
46. S.S. Moon, A.A. Rahman, J.Y. Kim, and S.H. Kee Hanultarin, a cytotoxic lignan as an inhibitor of actin cytoskeleton polymerization from the seeds of Trichosanthes kirilowii Bioorganic & Medicinal Chemistry 16 15 2008 7264 7269
47. K. Nabeta, M. Hirata, Y. Ohki, S.W.A. Samaraweera, and H. Okuyama Lignans in cell-cultures of Picea-glehnii Phytochemistry 37 2 1994 409 413
48. S. Nakashima, H. Matsuda, Y. Oda, S. Nakamura, F.M. Xu, and M. Yoshikawa Melanogenesis inhibitors from the desert plant Anastatica hierochuntica in B16 melanoma cells Bioorganic & Medicinal Chemistry 18 6 2010 2337 2345
49. Y.C. Oh, O.H. Kang, J.G. Choi, H.S. Chae, Y.S. Lee, and O.O. Brice Anti-inflammatory effect of resveratrol by inhibition of IL-8 production in LPS-induced THP-1 cells American Journal of Chinese Medicine 37 6 2009 1203 1214
50. F. Ouyang, Y. Liu, R. Li, L. Ling, N.L. Wang, and X.S. Yao Five lignans and an iridoid from Sambucus williamsii Chinese Journal of Natural Medicines 9 1 2011 0026 0029
51. H.F. Pan, and L.N. Lundgren Phenolic extractives from root bark of Picea-abies Phytochemistry 39 6 1995 1423 1428
52. R.B. Pearce Effects of exposure to high ozone concentrations on stilbenes in Sitka spruce (Picea sitchensis (Bong) Carr) bark and on its lignification response to infection with Heterobasidion annosum (Fr) Bref Physiological and Molecular Plant Pathology 48 2 1996 117 129 (Pubitemid 26311632)
53. Pellicia, M. T., Gianella, A., & Gianella, J. (2001). Resveratrol for the treatment of exfoliative eczema, acne or psoriasis. US20010056071.
54. J.M. Pepper, and Y.W. Lee Lignin and related compounds. I. A Comparative study of catalysts for lignin hydrogenolysis Canadian Journal of Chemistry 47 5 1969 723 727
55. S.P. Pietarinen, S.M. Willfor, M.O. Ahotupa, J.E. Hemming, and B.R. Holmbom Knotwood and bark extracts: Strong antioxidants from waste materials Journal of Wood Science 52 5 2006 436 444 (Pubitemid 44510989)
56. W. Pigman, E. Anderson, R. Fischer, M.A. Buchanan, and B.L. Browning Color precursors in spruce woods and western hemlockwoods and inner barks Tappi 36 1 1953 4 12
57. L.J. Porter, L.N. Hrstich, and B.G. Chan The conversion of procyanidins and prodelphinidins to cyanidin and delphinidin Phytochemistry 25 1 1986 223 230
58. Z.A. Rabesa, and B. Voirin New O-methylated flavone aglycones derived from mearnsetine in Alluaudia-ascendens Phytochemistry 18 2 1979 360 362
59. M.M.A. Rahman, P.M. Dewick, D.E. Jackson, and J.A. Lucas Lignans of Forsythia-intermedia Phytochemistry 29 6 1990 1971 1980
60. A. Roldan, V. Palacios, I. Caro, and L. Perez Resveratrol content of Palomino fino grapes: Influence of vintage and fungal infection Journal of Agricultural and Food Chemistry 51 5 2003 1464 1468
61. C.H. Rolfs, and H. Kindl Stilbene synthase and chalcone synthase - 2. Different constitutive enzymes in cultured-cells of Picea-excelsa Plant Physiology 75 2 1984 489 492
62. A. Rummukainen, R. Julkunen-Tiitto, M. Raisanen, and T. Lehto Phenolic compounds in Norway spruce as affected by boron nutrition at the end of the growing season Plant and Soil 292 1-2 2007 13 23 (Pubitemid 46466279)
63. A. Sakushima, M. Coskun, S. Hisada, and S. Nishibe Flavonoids from Rhamnus-pallasii Phytochemistry 22 7 1983 1677 1678
64. T.H. Sanders, R.W. McMichael, and K.W. Hendrix Occurrence of resveratrol in edible peanuts Journal of Agricultural and Food Chemistry 48 4 2000 1243 1246 (Pubitemid 30243692)
65. R.A. Savidge, and H. Forster Coniferyl alcohol metabolism in conifers - II. Coniferyl alcohol and dihydroconiferyl alcohol biosynthesis Phytochemistry 57 7 2001 1095 1103 (Pubitemid 32631451)
66. P. Schofield, D.M. Mbugua, and A.N. Pell Analysis of condensed tannins: A review Animal Feed Science and Technology 91 1-2 2001 21 40 (Pubitemid 32515977)
67. S. Shibutani, M. Samejima, and S. Doi Effects of stilbenes from bark of Picea glehnii (Sieb. et Zucc) and their related compounds against feeding behaviour of Reticulitermes speratus (Kolbe) Journal of Wood Science 50 5 2004 439 444 (Pubitemid 40024891)
68. R. Slimestad Flavonoids in buds and young needles of Picea, Pinus and Abies Biochemical Systematics and Ecology 31 11 2003 1247 1255 (Pubitemid 37316985)
69. R. Slimestad, O.M. Andersen, G.W. Francis, A. Marston, and K. Hostettmann Syringetin 3-O-(6″-acetyl)-beta-glucopyranoside and other flavonols from needles of Norway spruce Picea-abies. Phytochemistry 40 5 1995 1537 1542
70. R. Slimestad, G.W. Francis, and O.M. Andersen Directed search for plant constituents: A case study concerning flavonoids in Norway spruce Euphytica 105 2 1999 119 123 (Pubitemid 29111707)
71. R. Slimestad, and K. Hostettmann Characterisation of phenolic constituents from juvenile and mature needles of Norway spruce by means of high performance liquid chromatography mass spectrometry Phytochemical Analysis 7 1 1996 42 48
72. Z.J. Song, W.Q. Chen, X.Y. Du, H. Zhang, L.J. Lin, and H.H. Xu Chemical constituents of Picea neoveitchii Phytochemistry 72 6 2011 490 494
73. J. Soukupova, M. Cvikrova, J. Albrechtova, B.N. Rock, and J. Eder Histochemical and biochemical approaches to the study of phenolic compounds and peroxidases in needles of Norway spruce (Picea abies) New Phytologist 146 3 2000 403 414 (Pubitemid 30441911)
74. T. Stevanovic, P.N. Diouf, and M.E. García-Pérez Bioactive polyphenols from healthy diets and forest biomass Current Nutrition & Food Science 5 2009 264 295
75. N.A. Swain, R.C.D. Brown, and G. Bruton A versatile stereoselective synthesis of endo, exo-furofuranones: Application to the enantioselective synthesis of furofuran lignans Journal of Organic Chemistry 69 1 2004 122 129 (Pubitemid 38040816)
76. T. Vanek, J. Halik, R. Vankova, and I. Valterova Formation of trans-verbenol and verbenone from alpha-pinene catalysed by immobilised Picea abies cells Bioscience Biotechnology and Biochemistry 69 2 2005 321 325 (Pubitemid 40413253)
77. B.C. Vastano, Y. Chen, N.Q. Zhu, C.T. Ho, Z.Y. Zhou, and R.T. Rosen Isolation and identification of stilbenes in two varieties of Polygonum cuspidatum Journal of Agricultural and Food Chemistry 48 2 2000 253 256 (Pubitemid 30120350)
78. S. Wada, Y. Yasui, H. Tokuda, and R. Tanaka Anti-tumor-initiating effects of phenolic compounds isolated from the bark of Picea jezoensis var. jezoensis Bioorganic & Medicinal Chemistry 17 17 2009 6414 6421
79. S.I. Wada, Y. Yasui, T. Hitomi, and R. Tanaka Structures and radical-scavenging activities of phenolic constituents from the bark of Picea jezoensis var. jezoensis Journal of Natural Products 70 10 2007 1605 1610 (Pubitemid 350155411)
80. K. Weinges Die Lignane des Überwallungsharzes der Fichte Tetrahedron Letters 20 1960 1 2
81. S. Willfor, J. Hemming, M. Reunanen, C. Eckerman, and B. Holmbom Lignans and lipophilic extractives in Norway spruce knots and stemwood Holzforschung 57 1 2003 27 36
82. S. Willfor, L. Nisula, J. Hemming, M. Reunanen, and B. Holmbom Bioactive phenolic substances in industrially important tree species. Part 1: Knots and stemwood of different spruce species Holzforschung 58 4 2004 335 344
83. L.H. Xie, T. Akao, K. Hamasaki, T. Deyama, and M. Hattori Biotransformation of pinoresinol diglucoside to mammalian lignans by human intestinal microflora, and isolation of Enterococcus faecalis strain PDG-1 responsible for the transformation of (+)-pinoresinol to (+)-lariciresinol Chemical & Pharmaceutical Bulletin 51 5 2003 508 515 (Pubitemid 41656801)
84. X.W. Yang, L. Feng, S.M. Li, X.H. Liu, Y.L. Li, and L. Wu Isolation, structure, and bioactivities of abiesadines A-Y, 25 new diterpenes from Abies georgei Orr Bioorganic & Medicinal Chemistry 18 2 2010 744 754
85. K. Yildirim Biotransformation of (-)-verbenone by some fungi Journal of Chemical Research 3 2011 133 134
86. B. Zhao, and C.A. Hall Composition and antioxidant activity of raisin extracts obtained from various solvents Food Chemistry 108 2 2008 511 518