1H-nuclear magnetic resonance analysis of the triacylglyceride composition of cold-pressed oil from Camellia japonica

Molecules

Volumn 17, Issue 6, 2012, Pages 6716-6727

  Salinero, Carmen ^a   Feás, Xesús ^b   Pedro Mansilla, J ^a   Seijas, Julio A ^b   Pilar Vazquez Tato M ^b   Vela, Pilar ^a   Sainz, María J ^b  

^a Areeiro Phytopathological Station   (Spain)

^b UNIVERSITY OF SANTIAGO DE COMPOSTELA   (Spain)

Author keywords

13C NMR; 1H NMR; Camellia japonica; Nuclear magnetic resonance; Oil; Triacylglycerides

Indexed keywords

FATTY ACID; TRIACYLGLYCEROL; UNSATURATED FATTY ACID; VEGETABLE OIL;

ARTICLE; CHEMISTRY; NUCLEAR MAGNETIC RESONANCE; TEA;

CAMELLIA; FATTY ACIDS; FATTY ACIDS, UNSATURATED; NUCLEAR MAGNETIC RESONANCE, BIOMOLECULAR; PLANT OILS; TRIGLYCERIDES;

EID: 84862993227     PISSN: None     EISSN: 14203049     Source Type: Journal    
DOI: 10.3390/molecules17066728     Document Type: Article

References (42)

1. Ming, T. L.; Bartholomew, B. Theaceae. In Flora of China; Wu, Z. Y., Raven, P. H., Hong, D. Y., Eds.; Science Press: Beijing, China, and Missouri Botanical Garden: St. Louis, MO, USA, 2007; Volume 12, pp. 366-478.
2. Gao, J. Y.; Parks, C. R.; Du, Y. Q. Collected Species of the Genus Camellia-An Illustrated Outline; Zhejiang Scientific & Technology: Hangzhou, China, 2005.
3. Savige, T. J. The International Camellia Register; The International Camellia Society: Wirlinga, NSW, Australia, 1993.
4. Yoshikawa, M.; Morikawa, T.; Asao, Y.; Fujiwara, E.; Nakamura, S.; Matsuda, H. Medicinal Flowers. XV. The Structures of Noroleanane-and Oleanane-Type Triterpene Oligoglycosides with Gastroprotective and Platelet Aggregation Activities from Flower Buds of Camellia Japonica. Chem. Pharm. Bull. 2007, 55, 606-612. (Pubitemid 46570841)
5. Han, L.; Hatano, T.; Yoshida, T.; Okuda, T. Tannins of Theaceous Plants. V. Camelliatannins F, G and H, Three New Tannins from Camellia Jjaponica L. Chem. Pharm. Bull. 1994, 42, 1399-1409. (Pubitemid 24244083)
6. Saito, N.; Yokoi, M.; Yamaji, M.; Honda, T. Cyanidin 3-p- Coumaroylglucoside in Camellia Species and Cultivars. Phytochemistry 1987, 26, 2761-2762.
7. Thao, N. T. P.; Hung, T. M.; Lee, M. K.; Kim, J. C.; Min, B. S.; Bae, K. Triterpenoids from Camellia Japonica and their Cytotoxic Activity. Chem. Pharm. Bull. 2010, 58, 121-124.
8. Yoshikawa, M.; Morikawa, T.; Fujiwara, E.; Ohgushi, T.; Asao, Y.; Matsuda, H. New Noroleanane-Type Triterpene Saponins with Gastroprotective Effect and Platelet Aggregation Activity from the Flowers of Camellia Japonica: Revised Structures of Camellenodiol and Camelledionol. Heterocycles 2001, 55, 1653-1657. (Pubitemid 33021650)
9. Hatano, T.; Han, L.; Taniguchi, S.; Shingu, T.; Okuda, T.; Yoshida, T. Tannins and Related Polyphenols of Theaceous Plants. VIII. Camelliatannins C and E, New Complex Tannins from Camellia Japonica Leaves. Chem. Pharm. Bull. 1995, 43, 1629-1633.
10. Azuma, C. M.; dos Santos, F. C. S.; Lago, J. H. G. Flavonoids and Fatty Acids of Camellia Japonica Leaves Extract. Braz. J. Pharamacogn. 2011, 21, 1159-1162.
11. Cho, J.; Ji, S.; Moon, J.; Lee, K.; Jung, K.; Park, K. A Novel Benzoyl Glucoside and Phenolic Compounds from the Leaves of Camellia Japonica. Food Sci. Biotechnol. 2008, 17, 1060-1065.
12. Zhang, Y.; Yin, C.; Kong, L.; Jiang, D. Extraction Optimisation, Purification and Major Antioxidant Component of Red Pigments Extracted from Camellia Japonica. Food Chem. 2011, 129, 660-664.
13. Kim, K. Y.; Davidson, P. M.; Chung, H. J. Antibacterial Activity in Extracts of Camellia Japonica L. Petals and its Application to a Model Food System. J. Food Protect. 2001, 64, 1255-1260. (Pubitemid 32763574)
14. Onodera, K.; Hanashiro, K.; Yasumoto, T. Camellianoside, a Novel Antioxidant Glycoside from the Leaves of Camellia Japonica. Biosci. Biotechnol. Biochem. 2006, 70, 1995-1998. (Pubitemid 44285440)
15. Piao, M. J.; Yoo, E. S.; Koh, Y. S.; Kang, H. K.; Kim, J.; Kim, Y. J.; Kang, H. H.; Hyun, J. W. Antioxidant Effects of the Ethanol Extract from Flower of Camellia japonica via Scavenging of Reactive Oxygen Species and Induction of Antioxidant Enzymes. Int. J. Mol. Sci. 2011, 12, 2618-2630.
16. Thao, N. T. P.; Hung, T. M.; Lee, M. K.; Kim, J. C.; Min, B. S.; Bae, K. Triterpenoids from Camellia Japonica and their Cytotoxic Activity. Chem. Pharm. Bull. 2010, 58, 121-124.
17. Jeong, C.; Kim, J. H.; Choi, G. N.; Kwak, J. H.; Kim, D.; Heo, H. J. Protective Effects of Extract with Phenolics from Camellia (Camellia Japonica) Leaf Against Oxidative Stress-Induced Neurotoxicity. Food Sci. Biotechnol. 2010, 19, 1347-1353.
18. Onodera, K. I.; Tsuha, K.; Yasumoto-Hirose, M.; Tsuha, K.; Hanashiro, K.; Naoki, H.; Yasumoto, T. Okicamelliaside, an Extraordinarily Potent Anti-Degranulation Glucoside Isolated from Leaves of Camellia Japonica. Biosci. Biotechnol. Biochem. 2010, 74, 2532-2534.
19. Kuba, M.; Tsuha, K.; Tsuha, K.; Matsuzaki, G.; Yasumoto, T. In Vivo Analysis of the Anti-Allergic Activities of Camellia Japonica Extract and Okicamelliaside, a Degranulation Inhibitor. J. Health Sci. 2008, 54, 584-588.
20. Lee, J.; Kim, J.; Ko, N.; Mun, S.; Kim, D.; Kim, J.; Kim, H.; Lee, K.; Kim, Y.; Radinger, M.; et al. Camellia Japonica Suppresses Immunoglobulin E-Mediated Allergic Response by the Inhibition of Syk Kinase Activation in Mast Cells. Clin. Exp. Allergy 2008, 38, 794-804. (Pubitemid 351550663)
21. Park, J. C.; Hur, J. M.; Park, J. G.; Hatano, T.; Yoshida, T.; Miyashiro, H.; Min, B. S.; Hattori, M. Inhibitory Effects of Korean Medicinal Plants and Camelliatannin H from Camellia Japonica on Human Immunodeficiency Virus Type 1 Protease. Phytother. Res. 2002, 16, 422-426. (Pubitemid 34947950)
22. Akihisa, T.; Tokuda, H.; Ukiya, M.; Suzuki, T.; Enjo, F.; Koike, K.; Nikaido, T.; Nishino, H. 3-Epicabraleahydroxylactone and Other Triterpenoids from Camellia Oil and their Inhibitory Effects on Epstein-Barr Virus Activation. Chem. Pharm. Bull. 2004, 52, 153-156. (Pubitemid 41685570)
23. Somasundaram, A. Antidiabetic Activity of Methanolic Extract of Camellia japonica Leaves against Alloxan Induced Diabetes in Rats. Int. J. Pharm. BioSci. 2011, 1, 43-46.
24. Yoshikawa, M.; Harada, E.; Murakami, T.; Matsuda, H.; Yamahara, J.; Murakami, N. Camelliasaponins B1, B2, C1 and C2, New Type Inhibitors of Ethanol Absorption in Rats from the Seeds of Camellia Japonica L. Chem. Pharm. Bull. 1994, 42, 742-744. (Pubitemid 24156312)
25. Jung, E.; Lee, J.; Baek, J.; Jung, K.; Lee, J.; Huh, S.; Kim, S.; Koh, J.; Park, D. Effect of Camellia Japonica Oil on Human Type I Procollagen Production and Skin Barrier Function. J. Ethnopharmacol. 2007, 112, 127-131. (Pubitemid 46722596)
26. Ming, T. L. Monograph of the Genus Camellia; Yunnan Science and Technology Press: Kunming, China, 2000.
27. Mondal, T. K. Camellia. In Wild Crop Relatives: Genomic and Breeding Resources; Kole, C., Ed.; Springer-Verlag: Berlin/Heidelberg, Germany, 2011; pp. 15-39.
28. Wang, L.; Lee, F. S. C.; Wang, X.; He, Y. Feasibility Study of Quantifying and Discriminating Soybean Oil Adulteration in Camellia Oils by Attenuated Total Reflectance MIR and Fiber Optic Diffuse Reflectance NIR. Food Chem. 2006, 95, 529-536. (Pubitemid 41400232)
29. Buchgraber, M.; Ulberth, F.; Emons, H.; Anklam, E. Triacylglycerol Profiling by Using Chromatographic Techniques. Eur. J. Lipid Sci. Technol. 2004, 106, 621-648. (Pubitemid 39430473)
30. Laakso, P. Analysis of Triacylglycerols-Approaching the Molecular Composition of Natural Mixtures. Food Rev. Int. 1996, 12, 199-250.
31. Ribeiro, A. P. B.; Basso, R. C.; Grimaldi, R.; Gioielli, L. A.; Guaraldo, L. A. Instrumental Methods for the Evaluation of Interesterified Fats. Food Anal. Methods 2009, 2, 282-302.
32. Martinez, I.; Aursand, M.; Erikson, U.; Singstad, T. E.; Veliyulin, E.; Van der Zwaag, C. Destructive and Non-Destructive Analytical Techniques for Authentication and Composition Analyses of Foodstuffs. Trends Food Sci. Technol. 2003, 14, 489-498. (Pubitemid 37399473)
33. Beyer, T.; Diehl, B.; Holzgrabe, U. Quantitative NMR Spectroscopy of Biologically Active Substances and Excipients. Bioanal. Rev. 2010, 2, 1-22.
34. 1H Nuclear Magnetic Resonance in the Study of Edible Oils and Fats. Trends Food Sci. Technol. 2001, 12, 328-338. (Pubitemid 34623293)
35. 1H nuclear magnetic resonance as a fast tool for determining the composition of acyl chains in acylglycerol mixtures. Eur. J. Lipid Sci. Technol. 2003, 105, 502-507. (Pubitemid 37206153)
36. Guillen, M. D.; Ruiz, A. Rapid simultaneous determination by proton NMR of unsaturation and composition of acyl groups in vegetable oils. Eur. J. Lipid Sci. Technol. 2003, 105, 688-696. (Pubitemid 37533026)
37. Lie Ken Jie, M. S. F.; Mustafa, J. High-Resolution Nuclear Magnetic Resonance Spectroscopy-Applications to Fatty Acids and Triacylglycerols. Lipids 1997, 32, 1019-1034. (Pubitemid 27459409)
38. Vlahov, G. Application of NMR to the Study of Olive Oils. Prog. Nucl. Magn. Reson. Spectrosc. 1999, 35, 341-357. (Pubitemid 129593319)
39. 13C-NMR Spectra of Triglycerides: Implications for the NMR Analysis of Olive Oil. Magn. Reson. Chem. 2000, 38, 886-890.
40. Guillén, M. D.; Ruiz, A. Study by Means of Proton Nuclear Magnetic Resonance of the Thermal Oxidation Process Undergone by Oils Rich in Oleic Acyl Groups. J. Am. Oil Chem. Soc. 2005, 82, 349-355. (Pubitemid 43066417)
41. Guillén, M. D.; Ruiz, A. Monitoring of Heat-Induced Degradation of Edible Oils by Proton NMR. Eur. J. Lipid Sci. Technol. 2008, 110, 52-60. (Pubitemid 351184989)
42. Haiyan, Z.; Bedgood, D. R.; Bishop, A. G.; Prenzler, P. D.; Robards, K. Endogenous biophenol, fatty acid and volatile profiles of selected oils. Food Chem. 2006, 100, 1544-1551. (Pubitemid 44142877)