Relationships between degree of polymerization and antioxidant activities: A study on proanthocyanidins from the leaves of a medicinal mangrove plant Ceriops tagal

PLoS ONE

Volumn 9, Issue 10, 2014, Pages

  Zhou, Hai Chao ^a,b,c   Tam, Nora Fung Yee ^b,c   Lin, Yi Ming ^a   Ding, Zhen Hua ^a   Chai, Wei Ming ^a   Wei, Shu Dong ^a  

^a XIAMEN UNIVERSITY   (China)

^b CITY UNIVERSITY OF HONG KONG   (Hong Kong)

^c City University of Hong Kong Shenzhen Research Institute ^*  (Hong Kong)

Author keywords

[No Author keywords available]

Indexed keywords

PROANTHOCYANIDIN; TANNIN; ANTIOXIDANT; PHENOL DERIVATIVE; PLANT EXTRACT;

ANTIOXIDANT ACTIVITY; ARTICLE; CARBON NUCLEAR MAGNETIC RESONANCE; CERIOPS TAGAL; CONTROLLED STUDY; CORRELATIONAL STUDY; DPPH RADICAL SCAVENGING ASSAY; ELECTROSPRAY MASS SPECTROMETRY; EXTRACTION; FRACTIONATION; HIGH PERFORMANCE LIQUID CHROMATOGRAPHY; MATRIX ASSISTED LASER DESORPTION IONIZATION TIME OF FLIGHT MASS SPECTROMETRY; NONHUMAN; PLANT LEAF; POLYMERIZATION; PURIFICATION; REVERSED PHASE HIGH PERFORMANCE LIQUID CHROMATOGRAPHY; RHIZOPHORACEAE; STRUCTURE ACTIVITY RELATION; CHEMISTRY; GEL CHROMATOGRAPHY; ISOLATION AND PURIFICATION; MASS SPECTROMETRY; MEDICINAL PLANT; METABOLISM; NUCLEAR MAGNETIC RESONANCE SPECTROSCOPY; REGRESSION ANALYSIS;

CERIOPS TAGAL;

ANTIOXIDANTS; CHROMATOGRAPHY, GEL; CHROMATOGRAPHY, HIGH PRESSURE LIQUID; MAGNETIC RESONANCE SPECTROSCOPY; PHENOLS; PLANT EXTRACTS; PLANT LEAVES; PLANTS, MEDICINAL; POLYMERIZATION; PROANTHOCYANIDINS; REGRESSION ANALYSIS; RHIZOPHORACEAE; SPECTROMETRY, MASS, ELECTROSPRAY IONIZATION; SPECTROMETRY, MASS, MATRIX-ASSISTED LASER DESORPTION-IONIZATION;

EID: 84908101958     PISSN: None     EISSN: 19326203     Source Type: Journal    
DOI: 10.1371/journal.pone.0107606     Document Type: Article

References (48)

1. Lin P (2006) Marine higher plant ecology. Science Press, Beijing: 76-80.
2. Rastogi RP, Mehrotra BN (1991) Compendium of Indian medicinal plants. Publications & Information Directorate, New Delhi 1.
3. Chen JD, Qiu Y, Yang ZW, Lin P, Lin YM (2008) Dimeric diterpenes from the roots of the mangrove plant Ceriops tagal. Helvetica Chimica Acta 91: 2292-2298.
4. Chacha M, Mapitse R, Afolayan AJ, Majinda RRT (2008) Antibacterial diterpenes from the roots of Ceriops tagal. Natural Product Communications 3: 17-20.
5. Feller IC, Whigham DF, O'Neill JP, McKee KL (1999) Effects of nutrient enrichment on within-stand cycling in a mangrove forest. Ecology 80: 2193-2205.
6. Mainoya J, Mesaki S, Banyikwa F (1986) The distribution and socio-economic aspects of mangrove forests in Tanzania. Man in the Mangroves: the Socio- Economic Situation of Human Settlements in Mangrove Forests: 87-95.
7. Kraus TEC, Dahlgren RA, Zasoski RJ (2003) Tannins in nutrient dynamics of forest ecosystems - a review. Plant and Soil 256: 41-66.
8. Lin YM, Liu JW, Xiang P, Lin P, Ye GF, et al. (2006) Tannin dynamics of propagules and leaves of Kandelia candel and Bruguiera gymnorrhiza in the Jiulong River Estuary, Fujian, China. Biogeochemistry 78: 343-359.
9. Zhou HC, Tam NYF, Lin YM, Wei SD, Li YY (2012) Changes of condensed tannins during decomposition of leaves of Kandelia obovata in a subtropical mangrove swamp in China. Soil Biology and Biochemistry 44: 113-121.
10. Zhang LL, Lin YM, Zhou HC, Wei SD, Chen JH (2010) Condensed tannins from mangrove species Kandelia candel and Rhizophora mangle and their antioxidant activity. Molecules 15: 420-431.
11. Maie N, Pisani O, Jaffe R (2008) Mangrove tannins in aquatic ecosystems: Their fate and possible influence on dissolved organic carbon and nitrogen cycling. Limnology and Oceanography 53: 160-171.
12. Oo CW, Pizzi A, Pasch H, Kassim MJ (2008) Study on the structure of mangrove polyflavonoid tannins with MALDI-TOF mass spectrometry. Journal of Applied Polymer Science 109: 963-967.
13. Hernes PJ, Benner R, Cowie GL, Goni MA, Bergamaschi BA, et al. (2001) Tannin diagenesis in mangrove leaves from a tropical estuary: A novel molecular approach. Geochimica Et Cosmochimica Acta 65: 3109-3122.
14. Wang Y, Zhu H, Tam NFY (2014) Polyphenols, tannins and antioxidant activities of eight true mangrove plant species in South China. Plant and Soil 374: 549-563.
15. Khanbabaee K, van Ree T (2001) Tannins: Classification and definition. Natural Product Reports 18: 641-649.
16. Alasalvar C, Karamac M, Kosinska A, Rybarczyk A, Shahidi F, et al. (2009) Antioxidant Activity of Hazelnut Skin Phenolics. Journal of Agricultural and Food Chemistry 57: 4645-4650.
17. Monagas M, Quintanilla-Lopez JE, Gomez-Cordoves C, Bartolome B, Lebron- Aguilar R (2010) MALDI-TOF MS analysis of plant proanthocyanidins. Journal of Pharmaceutical and Biomedical Analysis 51: 358-372.
18. Chai WM, Shi Y, Feng HL, Qiu L, Zhou HC, et al. (2012) NMR, HPLC-ESIMS, and MALDI-TOF MS analysis of condensed tannins from Delonix regia (Bojer ex Hook.) Raf. and their bioactivities. Journal of Agricultural and Food Chemistry 60: 5013-5022.
19. Chen XX, Shi Y, Chai WM, Feng HL, Zhuang JX, et al. (2014) Condensed tannins from Ficus virens as tyrosinase inhibitors: structure, inhibitory activity and molecular mechanism. Plos One 9: e91809.
20. Gu LW, Kelm M, Hammerstone JF, Beecher G, Cunningham D, et al. (2002) Fractionation of polymeric procyanidins from lowbush blueberry and quantification of procyanidins in selected foods with an optimized normal-phase HPLC-MS fluorescent detection method. Journal of Agricultural and Food Chemistry 50: 4852-4860.
21. Li CM, Leverence R, Trombley JD, Xu SF, Yang J, et al. (2010) High molecular weight persimmon (Diospyros kaki L.) proanthocyanidin: a highly galloylated, Alinked tannin with an unusual flavonol terminal unit, myricetin. Journal of Agricultural and Food Chemistry 58: 9033-9042.
22. Ariga T, HAMANO M (1990) Radical scavenging action and its mode in procyanidins B-1 and B-3 from azuki beans to peroxyl radicals. Agricultural and Biological Chemistry 54: 2499-2504.
23. Hagerman AE, Riedl KM, Jones GA, Sovik KN, Ritchard NT, et al. (1998) High molecular weight plant polyphenolics (tannins) as biological antioxidants. Journal of Agricultural and Food Chemistry 46: 1887-1892.
24. Es-Safi NE, Guyot S, Ducrot PH (2006) NMR, ESI/MS, and MALDI-TOF/ MS analysis of pear juice polymeric proanthocyanidins with potent free radical scavenging activity. Journal of Agricultural and Food Chemistry 54: 6969-6977.
25. Zhou HC, Lin YM, Li YY, Li M, Wei SD, et al. (2011) Antioxidant properties of polymeric proanthocyanidins from fruit stones and pericarps of Litchi chinensis Sonn. Food Research International 44: 613-620.
26. Makkar HPS, Blümmel M, Borowy NK, Becker K (1993) Gravimetric determination of tannins and their correlations with chemical and protein precipitation methods. Journal of Agricultural and Food Chemistry 61: 161-165.
27. Terrill TH, Rowan AM, Douglas GD, Barry TN (1992) Determination of extractable and bound condensed tannin concentrations in forage plants, protein concentrate meals and cereal grains. Journal of the Science of Food and Agriculture 58: 321-329.
28. Hellstrom J, Sinkkonen J, Karonen M, Mattila P (2007) Isolation and structure elucidation of procyanidin oligomers from saskatoon berries (Amelanchier alnifolia). Journal of Agricultural and Food Chemistry 55: 157-164.
29. Zhou HC, Lin YM, Chai WM, Wei SD, Liao MM (2011) Characterization of condensed tannins from litchi seed by reflectron modes and linear modes of MALDI-TOF MS. Acta Chimica Sinica 69: 2981-2986.
30. Brand-Williams W, Cuvelier ME, Berset C (1995) Use of a free radical method to evaluate antioxidant activity. Lebensmittel Wissenschaft and Technologie 28: 25-30.
31. Benzie IFF, Strain JJ (1996) The ferric reducing ability of plasma as a measure of ''antioxidant power'': the FRAP assay. Analytical Biochemistry 239: 70-76.
32. Zhou HC, Lin YM, Wei SD, Tam NFY (2011) Structural diversity and antioxidant activity of condensed tannins fractionated from mangosteen pericarp. Food Chemistry 129: 1710-1720.
33. Cai YZ, Sun M, Xing J, Luo Q, Corke H (2006) Structure-radical scavenging activity relationships of phenolic compounds from traditional Chinese medicinal plants. Life Sciences 78: 2872-2888.
34. Chirinos R, Rogez H, Campos D, Pedreschi R, Larondelle Y (2007) Optimization of extraction conditions of antioxidant phenolic compounds from mashua (Tropaeolum tuberosum Ruiz & Pavo) tubers. Separation and Purification Technology 55: 217-225.
35. Czochanska BZ, Foo YL, Newman RH, Porter LJ (1980) Polymeric proanthocyanidin. stereochemistry, structural units, and molecular weight. Journal of the Chemical Society, Perkin Transactions 1: 2278-2286.
36. Fu C, Loo AEK, Chia FPP, Huang D (2007) Oligomeric proanthocyanidins from mangosteen pericarps. Journal of Agricultural and Food Chemistry 55: 7689-7694.
37. Kraus TEC, Yu Z, Preston CM, Dahlgren RA, Zasoski RJ (2003) Linking chemical reactivity and protein precipitation to structural characteristics of foliar tannins. Journal of Chemical Ecology 29: 703-730.
38. Castillo-Munoz N, Gomez-Alonso S, Garcia-Romero E, Gomez MV, Velders AH, et al. (2009) Flavonol 3-O-glycosides series of Vitis vinifera cv. Petit Verdot red wine grapes. Journal of Agricultural and Food Chemistry 57: 209-219.
39. Reed JD, Krueger CG, Vestling MM (2005) MALDI-TOF mass spectrometry of oligomeric food polyphenols. Philadelphia, PA. Pergamon-Elsevier Science Ltd: 2248-2263.
40. Xiang P, Lin YM, Lin P, Xiang C, Yang ZW, et al. (2007) Effect of cationization reagents on the matrix-assisted laser desorption/ionization time-of-flight mass spectrum of Chinese gallotannins. Journal of Applied Polymer Science 105: 859-864.
41. Taylor AW, Barofsky E, Kennedy JA, Deinzer ML (2003) Hop (Humulus lupulus L.) proanthocyanidins characterized by mass spectrometry, acid catalysis, and gel permeation chromatography. Journal of Agricultural and Food Chemistry 51: 4101-4110.
42. Jerez M, Tourino S, Sineiro J, Torres JL, Nunez MJ (2007) Procyanidins from pine bark: Relationships between structure, composition and antiradical activity. Food Chemistry 104: 518-527.
43. Meri S, Kanner J, Akiri B, Hadas SP (1995) Determination and involvement of aqueous reducing compounds in oxidative defense systems of various senescing leaves. Journal of Agricultural and Food Chemistry 43: 1813-1815.
44. de Gaulejac N, Vivas N, de Freitas V, Bourgeois G (1999) The influence of various phenolic compounds on scavenging activity assessed by an enzymatic method. Journal of the Science of Food and Agriculture 79: 1081-1090.
45. Cai YZ, Luo Q, Sun M, Corke H (2004) Antioxidant activity and phenolic compounds of 112 traditional Chinese medicinal plants associated with anticancer. Life Sciences 74: 2157-2184.
46. Silva E, Souza J, Rogez H, Rees J, Larondelle Y (2007) Antioxidant activities and polyphenolic contents of fifteen selected plant species from the Amazonian region. Food Chemistry 101: 1012-1018.
47. Lizcano LJ, Bakkali F, Ruiz-Larrea MB, Ruiz-Sanz JI (2010) Antioxidant activity and polyphenol content of aqueous extracts from Colombian Amazonian plants with medicinal use. Food Chemistry 119: 1566-1570.
48. Guyot S, Marnet N, Drilleau JF (2001) Thiolysis-HPLC characterization of apple procyanidins covering a large range of polymerization states. Journal of Agricultural and Food Chemistry 49: 14-20.