Characterization of phenolic compounds in brazilian pepper (schinus terebinthifolius raddi) exocarp

Journal of Agricultural and Food Chemistry

Volumn 62, Issue 26, 2014, Pages 6219-6226

  Feuereisen, Michelle M ^a   Hoppe, Julia ^a   Zimmermann, Benno F ^a,b   Weber, Fabian ^a   Schulze Kaysers, Nadine ^a   Schieber, Andreas ^a  

^a UNIVERSITY OF BONN   (Germany)

^b Institut Prof Dr Kurz GmbH   (Germany)

Author keywords

Anacardiaceae; biflavones; chemotaxonomy; galloyl glucose; galloyl shikimic acid; methylated anthocyanidins; NMR; Schinus terebinthifolius; tandem mass spectrometry; UHPLC

Indexed keywords

BIOCHEMISTRY; FLAVONOIDS; GLUCOSE; MASS SPECTROMETRY; NUCLEAR MAGNETIC RESONANCE; NUCLEAR MAGNETIC RESONANCE SPECTROSCOPY; TANNINS;

ANACARDIACEAE; ANTHOCYANIDINS; BIFLAVONES; CHEMOTAXONOMY; GALLOYL GLUCOSE; SCHINUS TEREBINTHIFOLIUS; SHIKIMIC ACIDS; TANDEM MASS SPECTROMETRY; UHPLC;

CARBOXYLIC ACIDS;

FLAVONOID; PHENOL DERIVATIVE; PIGMENT;

ANACARDIACEAE; ANALYSIS; CHEMICAL STRUCTURE; CHEMISTRY; FOOD PRESERVATION; FRUIT; ISOLATION AND PURIFICATION; METABOLISM; METHYLATION; SURFACE PROPERTY;

ANACARDIACEAE; FLAVONOIDS; FOOD, PRESERVED; FRUIT; METHYLATION; MOLECULAR STRUCTURE; PHENOLS; PIGMENTS, BIOLOGICAL; SURFACE PROPERTIES;

ANACARDIACEAE; SCHINUS TEREBINTHIFOLIUS;

EID: 84903766138     PISSN: 00218561     EISSN: 15205118     Source Type: Journal    
DOI: 10.1021/jf500977d     Document Type: Article

References (47)

1. Miller, A. J.; Schaal, B. A. Domestication and the distribution of genetic variation in wild and cultivated populations of the Mesoamerican fruit tree Spondias purpurea L. (Anacardiaceae) Mol. Ecol. 2006, 15, 1467-1480
2. Rayne, S.; Mazza, G. Biological activities of extracts from sumac (Rhus spp.): a review Plant Foods Hum. Nutr. 2007, 62, 165-175
3. Mariod, A. A.; Abdelwahab, S. I. Sclerocarya birrea (Marula), an African tree of nutritional and medicinal uses: A review Food Rev. Int. 2012, 28, 375-388
4. Moyo, M.; Staden, J. Micropropagation of Anacardiaceae species of economic importance: advances and future prospects In Vitro Cell. Dev. Biol.-Plant 2012, 49, 85-96
5. www.fleppc.org.
6. Morgan, E. C.; Overholt, W. A. Potential allelopathic effects of Brazilian pepper (Schinus terebinthifolius Raddi, Anacardiaceae) aqueous extract on germination and growth of selected Florida native plants 1 J. Torrey Bot. Soc. 2005, 132, 11-15
7. Johann, S.; Pizzolatti, M. G.; Donnici, C. L.; de Resende, M. A. Antifungal properties of plants used in Brazilian traditional medicine against clinically relevant fungal pathogens Braz. J. Microbiol. 2007, 38, 632-637
8. Rhouma, A.; Ben Daoud, H.; Ghanmi, S.; Ben Salah, H.; Romdhane, M.; Demak, M. Antimicrobial activities of leaf extracts of Pistacia and Schinus species against some plant pathogenic fungi and bacteria J. Plant Pathol. 2009, 91, 339-345
9. Carvalho, M. G.; Melo, A.; Aragão, C.; Raffin, F. N.; Moura, T. Schinus terebinthifolius Raddi: chemical composition, biological properties and toxicity Rev. Bras. Planta Med. 2013, 15, 158-169
10. Berardini, N.; Carle, R.; Schieber, A. Characterization of gallotannins and benzophenone derivatives from mango (Mangifera indica L. cv. Tommy Atkins) peels, pulp and kernels by high-performance liquid chromatography/electrospray ionization mass spectrometry Rapid Commun. Mass Spectrom. 2004, 18, 2208-2216
11. Berardini, N.; Schieber, A.; Klaiber, I.; Beifuss, U.; Carle, R.; Conrad, J. 7- O -Methylcyanidin 3- O -β- d -galactopyranoside, a novel anthocyanin from mango (Mangifera indica L. cv. Tommy Atkins) peels Z. Naturforsch. 2005, 60, 801
12. Engels, C.; Schieber, A.; Gänzle, M. G. Inhibitory spectra and modes of antimicrobial action of gallotannins from mango kernels (Mangifera indica L.) Appl. Environ. Microbiol. 2011, 77, 2215-2223
13. Wrolstad, R. E.; Acree, T. E.; Decker, E. A.; Penner, M. H.; Reid, D. S.; Schwartz, S. J.; Shoemaker, C. F.; Smith, D.; Sporns, P. Anthocyanins. In Handbook of Food Analytical Chemistry; Wrolstad/Handbook; Wiley: Hoboken, NJ, USA, 2005; pp 5-69.
14. Wu, X.; Prior, R. L. Systematic identification and characterization of anthocyanins by HPLC-ESI-MS/MS in common foods in the United States: fruits and berries J. Agric. Food Chem. 2005, 53, 2589-2599
15. Kammerer, D.; Carle, R.; Schieber, A. Detection of peonidin and pelargonidin glycosides in black carrots (Daucus carota ssp. sativus var. atrorubens Alef.) by high-performance liquid chromatography/electrospray ionization mass spectrometry Rapid Commun. Mass Spectrom. 2003, 17, 2407-2412
16. Pawlowska, A. M.; Camangi, F.; Braca, A. Quali-quantitative analysis of flavonoids of Cornus mas L. (Cornaceae) fruits Food Chem. 2010, 119, 1257-1261
17. Seeram, N. P.; Schutzki, R.; Chandra, A.; Nair, M. G. Characterization, quantification, and bioactivities of anthocyanins in Cornus species J. Agric. Food Chem. 2002, 50, 2519-2523
18. Toki, K.; Saito, N.; Irie, Y.; Tatsuzawa, F.; Shigihara, A.; Honda, T. 7-O-Methylated anthocyanidin glycosides from Catharanthus roseus Phytochemistry 2008, 69, 1215-1219
19. Kirby, C. W.; Wu, T.; Tsao, R.; McCallum, J. L. Isolation and structural characterization of unusual pyranoanthocyanins and related anthocyanins from Staghorn sumac (Rhus typhina L.) via UPLC-ESI-MS, (1)H, (13)C, and 2D NMR spectroscopy Phytochemistry 2013, 94, 284-293
20. Pedersen, A. T.; Andersen, Ø. M.; Aksnes, D. W.; Nerdal, W. NMR of anthocyanins: assignments and effects of exchanging aromatic protons Magn. Reson. Chem. 1993, 31, 972-976
21. Bjorøy, Ø.; Fossen, T.; Andersen, Ø. M. Anthocyanin 3-galactosides from Cornus alba Sibirica with glucosidation of the B-ring Phytochemistry 2007, 68, 640-645
22. Schieber, A.; Berardini, N.; Carle, R. Identification of flavonol and xanthone glycosides from mango (Mangifera indica L. Cv. Tommy Atkins) peels by high-performance liquid chromatography-electrospray ionization mass spectrometry J. Agric. Food Chem. 2003, 51, 5006-5011
23. Berardini, N.; Fezer, R.; Conrad, J.; Beifuss, U.; Carle, R.; Schieber, A. Screening of mango (Mangifera indica L.) cultivars for their contents of flavonol O-and xanthone C -glycosides, anthocyanins, and pectin J. Agric. Food Chem. 2005, 53, 1563-1570
24. Engels, C.; Gräter, D.; Esquivel, P.; Jiménez, V. M.; Gänzle, M. G.; Schieber, A. Characterization of phenolic compounds in jocote (Spondias purpurea L.) peels by ultra high-performance liquid chromatography/electrospray ionization mass spectrometry Food Res. Int. 2012, 46, 557-562
25. Gordon, A.; Jungfer, E.; da Silva, B. A.; Maia, J. G. S.; Marx, F. Phenolic constituents and antioxidant capacity of four underutilized fruits from the Amazon region J. Agric. Food Chem. 2011, 59, 7688-7699
26. n J. Agric. Food Chem. 2010, 58, 4681-4692
27. Meyers, K. J.; Swiecki, T. J.; Mitchell, A. E. Understanding the native Californian diet: Identification of condensed and hydrolyzable tannins in Tanoak acorns (Lithocarpus densiflorus) J. Agric. Food Chem. 2006, 54, 7686-7691
28. Engels, C.; Gänzle, M. G.; Schieber, A. Fractionation of gallotannins from mango (Mangifera indica L.) kernels by high-speed counter-current chromatography and determination of their antibacterial activity J. Agric. Food Chem. 2010, 58, 775-780
29. Cavalher-Machado, S. C.; Rosas, E. C.; Brito, F. A. The anti-allergic activity of the acetate fraction of Schinus terebinthifolius leaves in IgE induced mice paw edema and pleurisy Int. Immunopharmacol. 2008, 8, 1552-1560
30. Arapitsas, P. Hydrolyzable tannin analysis in food Food Chem. 2012, 135, 1708-1717
31. Sáyago-Ayerdi, S. G.; Moreno-Hernández, C. L.; Montalvo-González, E.; García-Magaña, M. L.; de Oca, M. M.-M.; Torres, J. L.; Perez-Jimenez, J. Mexican Ataulfo mango (Mangifera indica L.) as a source of hydrolyzable tannins. Analysis by MALDI-TOF/TOF MS Food Res. Int. 2013, 51, 188-194
32. Engels, C.; Knödler, M.; Zhao, Y.-Y.; Carle, R.; Gänzle, M. G.; Schieber, A. Antimicrobial activity of gallotannins isolated from mango (Mangifera indica L.) kernels J. Agric. Food Chem. 2009, 57, 7712-7718
33. Pfundstein, B.; El Desouky, S. K.; Hull, W. E.; Haubner, R.; Erben, G.; Owen, R. W. Polyphenolic compounds in the fruits of Egyptian medicinal plants (Terminalia bellerica, Terminalia chebula and Terminalia horrida): characterization, quantitation and determination of antioxidant capacities Phytochemistry 2010, 71, 1132-1148
34. Singab, A.-N.; Ayoub, N.; Al-Sayed, E.; Martiskainen, O.; Sinkkonen, J.; Pihlaja, K. Phenolic constituents of Eucalyptus camaldulensis Dehnh, with potential antioxidant and cytotoxic activities Rec. Nat. Prod. 2011, 5, 271-280
35. Fecka, I.; Cisowski, W. Tannins and flavonoids from the Erodium cicutarium herb Z. Naturforsch. 2005, 60, 555-560
36. Huang, Y.-L.; Tanaka, T.; Matsuo, Y.; Kouno, I.; Li, D.-P.; Nonaka, G.-I. Two new phenolic glucosides and an ellagitannin from the leaves of Castanopsis sclerophylla Phytochem. Lett. 2012, 5, 158-161
37. Lee, M.-W.; Tanaka, T.; Nonaka, G.-I.; Nishioka, I. Dimeric ellagitannins from Alnus japonica Phytochemistry 1992, 31, 2835-2839
38. Nonaka, G.-I.; Nishioka, I.; Nishizawa, M.; Yamagishi, T.; Kashiwada, Y.; Dutschman, G. E.; Bodner, A. J.; Kilkuskie, R. E.; Cheng, Y.-C.; Lee, K.-H. Anti-AIDS agents, 2: Inhibitory effect of tannins on HIV reverse transcriptase and HIV replication in H9 lymphocyte cells J. Nat. Prod. 1990, 53, 587-595
39. Yokozawa, T.; Chen, C. P.; Dong, E.; Tanaka, T.; Nonaka, G. I.; Nishioka, I. Study on the inhibitory effect of tannins and flavonoids against the 1,1-diphenyl-2-picrylhydrazyl radical Biochem. Pharmacol. 1998, 56, 213-222
40. Kassem, M.; El-Desoky, S. K.; Sharaf, M. Biphenyl esters and biflavonoids from the fruits of Schinus terebenthefolus Chem. Nat. Compd. 2004, 40, 447-450
41. Lin, Y. M.; Chen, F. C. Agathisflavone from the drupes of Rhus succedanea Phytochemistry 1974, 13, 657-658
42. A/benzodiazepine receptor J. Ethnopharmacol. 2006, 103, 276-280
43. Konan, N. A.; Lincopan, N.; Collantes Díaz, I. E.; de Fátima Jacysyn, J.; Tanae Tiba, M. M.; Pessini Amarante Mendes, J. G.; Bacchi, E. M.; Spira, B. Cytotoxicity of cashew flavonoids towards malignant cell lines Exp. Toxicol. Pathol. 2012, 64, 435-440
44. Skopp, G.; Schwenker, G. Biflavonoide aus Schinus terebinthifolius Raddi (Anacardiaceae) Z. Naturforsch. 1986, 41, 1479-1482
45. Zhang, Y.-X.; Li, Q.-Y.; Yan, L.-L.; Shi, Y. Structural characterization and identification of biflavones in Selaginella tamariscina by liquid chromatography-diode-array detection/electrospray ionization tandem mass spectrometry Rapid Commun. Mass Spectrom. 2011, 25, 2173-2186
46. Michler, H.; Laakmann, G.; Wagner, H. Development of an LC-MS method for simultaneous quantitation of amentoflavone and biapigenin, the minor and major biflavones from Hypericum perforatum L., in human plasma and its application to real blood Phytochem. Anal. 2011, 22, 42-50
47. Oliveira, M. C.; Esperança, P.; Almoster Ferreira, M. A. Characterisation of anthocyanidins by electrospray ionisation and collision-induced dissociation tandem mass spectrometry Rapid Commun. Mass Spectrom. 2001, 15, 1525-1532