Planta Med 2015; 81(12/13): 1056-1064
DOI: 10.1055/s-0035-1545928
Biological and Pharmacological Activity
Original Papers
Georg Thieme Verlag KG Stuttgart · New York

Antioxidant and Free Radical Scavenging Activity of Phenolics from Bidens humilis [*]

Mariela Beatriz Vera Saltos
1   Dipartimento di Farmacia, Università di Pisa, Pisa, Italy
,
Blanca Fabiola Naranjo Puente
2   Departamento de Ciencias de la Vida, Universidad de las Fuerzas Armadas, ESPE, Sangolqui, Ecuador
,
Luigi Milella
3   Dipartimento di Scienze, Università degli Studi della Basilicata, Potenza, Italy
,
Nunziatina De Tommasi
4   Dipartimento di Farmacia, Università di Salerno, Salerno, Italy
,
Fabrizio Dal Piaz
4   Dipartimento di Farmacia, Università di Salerno, Salerno, Italy
,
Alessandra Braca
1   Dipartimento di Farmacia, Università di Pisa, Pisa, Italy
5   Centro Interdipartimentale di Ricerca “Nutraceutica e Alimentazione per la Salute”, Università di Pisa, Pisa, Italy
› Author Affiliations
Further Information

Publication History

received 01 February 2015
revised 12 March 2015

accepted 14 March 2015

Publication Date:
23 April 2015 (online)

Abstract

A bioassay-oriented approach led to the isolation of 11 compounds, including three new natural flavonoids, (2S)-isookanin 7-O-α-L-arabinopyranoside (1), (2S)-isookanin 7-O-(2′′-acetyl)-α-L-arabinopyranoside (2), and luteolin 7-O-β-D-glucopyranosyl-(1 → 6)-β-D-galactopyranoside (6), from Bidens humilis aerial parts. Their structures were determined via spectroscopic analyses including two-dimensional nuclear magnetic resonance. The antioxidant activity of all compounds was also tested by three different assays. The Relative Antioxidant Capacity Index (RACI) is applied herein, from the perspective of statistics, by integrating the antioxidant capacity data determined by these chemical methods.

* Dedicated to Professor Dr. Dr. h. c. mult. Adolf Nahrstedt on the occasion of his 75th birthday.


Supporting Information

 
  • References

  • 1 Bairwa K, Kumar R, Sharma RJ, Kumar Roy R. An update review on Bidens pilosa L. Der Pharma Chem 2010; 2: 324-337
  • 2 De Tommasi N, Piacente S, Pizza C. Flavonol and chalcone ester glycosides from Bidens andicola . J Nat Prod 1998; 61: 973-977
  • 3 Wang N, Yao X, Ishii R, Kitanaka S. Bioactive sucrose esters from Bidens parviflora . Phytochemistry 2003; 62: 741-746
  • 4 Gironés-Vilaplana A, Valentão P, Andrade PB, Ferreres F, Moreno DA, García-Viguera C. Phytochemical profile of a blend of black chokeberry and lemon juice with cholinesterase inhibitory effect and antioxidant potential. Food Chem 2012; 134: 2090-2096
  • 5 Milella L, Bader A, De Tommasi N, Russo D, Braca A. Antioxidant and free radical-scavenging activity of constituents from two Scorzonera species. Food Chem 2014; 160: 298-304
  • 6 von Gadow A, Joubert E, Hansmann CH. Comparison of the antioxidant activity of aspalathin with that of other plant phenols of rooibos tea (Aspalathus linearis), α-Tocopherol, BHT, and BHA. J Agric Food Chem 1997; 45: 632-638
  • 7 de Rijke E, Out P, Niessen WMA, Ariese F, Gooijer C, Brinkman UAT. Analytical separation and detection methods for flavonoids. J Chromatogr A 2006; 1112: 31-63
  • 8 Agrawal PK. Carbon-13 NMR of flavonoids. Amsterdam: Elsevier; 1989. 134. 314
  • 9 Sun LR, Qing C, Zhang YL, Jia SY, Li ZR, Pei SJ, Qiu MH, Gross ML, Qiu SX. Cimicifoetisides A and B, two cytotoxic cycloartane triterpenoid glycosides from the rhizomes of Cimicifuga foetida, inhibit proliferation of cancer cells. Beilstein J Org Chem 2007; 3: 1-7
  • 10 Shimokoriyama M. Antochlor pigments of Coreopsis tinctoria . J Am Chem Soc 1957; 79: 214-220
  • 11 Okada Y, Okita M, Murai Y, Okano Y, Nomura M. Isolation and identification of flavonoids from Coreopsis lanceolata L. petals. Nat Prod Res 2014; 28: 201-204
  • 12 Gupta SR, Ravindranath B, Seshadri TR. Glucosides of Butea monosperma . Phytochemistry 1970; 9: 2231-2235
  • 13 Romussi G, Fontana N, De Tommasi N. Flavonoids from Cymbalaria muralis Gaernt. Phytother Res 1996; 10 (Suppl. 01) S84-S85
  • 14 Iwai K, Kishimoto N, Kakino Y, Mochida K, Fujita T. In vitro antioxidative effects and tyrosinase inhibitory activities of seven hydroxycinnamoyl derivatives in green coffee beans. J Agric Food Chem 2004; 52: 4893-4898
  • 15 Choi JS, Islam MN, Ali MY, Kim YM, Park HJ, Sohn HS, Jung HA. The effects of C-glycosylation of luteolin on its antioxidant, anti-Alzheimerʼs disease, anti-diabetic, and anti-inflammatory activities. Arch Pharm Res 2014; 37: 1354-1363
  • 16 Zhang XL, Guo YS, Wang CH, Li GQ, Xu JJ, Chung HY, Ye WC, Li YL, Wang GC. Phenolic compounds from Origanum vulgare and their antioxidant and antiviral activities. Food Chem 2014; 152: 300-306
  • 17 Heim KE, Tagliaferro AR, Bobilya DJ. Flavonoid antioxidants: chemistry, metabolism and structure-activity relationships. J Nutr Biochem 2002; 13: 572-584
  • 18 Rice-Evans CA, Miller NJ, Paganga G. Structure-antioxidant activity relationships of flavonoids and phenolic acids. Free Radic Biol Med 1996; 20: 933-956
  • 19 Wu W, Yan C, Li L, Liu Z, Liu S. Studies on the flavones using liquid chromatography-electrospray ionization tandem mass spectrometry. J Chromatogr A 2004; 1047: 213-220
  • 20 Kuhn F, Oehme M, Romero F, Abou-Mansour E, Tabacchi R. Differentiation of isomeric flavone/isoflavone aglycones by MS2 ion trap mass spectrometry and a double neutral loss of CO. Rapid Commun Mass Spectrom 2003; 17: 1941-1949
  • 21 Jaiswal R, Karakoese H, Ruehmann S, Goldner K, Neumueller M, Treutter D, Kuhnert N. Identification of phenolic compounds in plum fruits (Prunus salicina L. and Prunus domestica L.) by high-performance liquid chromatography/tandem mass spectrometry and characterization of varieties by quantitative phenolic fingerprints. J Agric Food Chem 2013; 61: 12020-12031
  • 22 Padula MC, Lepore L, Milella L, Ovesna J, Malafronte N, Martelli G, De Tommasi N. Cultivar based selection and genetic analysis of strawberry fruits with high levels of health promoting compounds. Food Chem 2013; 140: 639-646
  • 23 Russo D, Bonomo MG, Salzano G, Martelli G, Milella L. Nutraceutical properties of Citrus clementina juices. Pharmacologyonline 2012; 1: 84-93
  • 24 Mikami I, Yamaguchi M, Shinmoto H, Tsushida T. Development and validation of a microplate-based β-carotene bleaching assay and comparison of antioxidant activity (AOA) in several crops measured by β-carotene bleaching, DPPH and ORAC assays. Food Sci Technol Res 2009; 15: 171-178