Detection and analysis of triterpenic compounds in apple extracts

References

• Ran, J.; Sun, H.; Xu, Y.; Wang, T.; Zhao, R. Comparison of Antioxidant Activities and High-Performance Liquid Chromatography Analysis of Polyphenol from Different Apple Varieties. International Journal Food Prop 2016, 19(11), 2396–2407. DOI: 10.1080/10942912.2015.1037958.
   Web of Science ®Google Scholar
• Marks, S. C.; Mullen, W.; Crozier, A. Flavonoid and Chlorogenic Acid Profiles of English Cider Apples. Journal of the Science of Food and Agriculture 2007, 87(4), 719–728. DOI: 10.1002/jsfa.3006.
   Web of Science ®Google Scholar
• Liaudanskas, M.; Viškelis, P.; Kviklys, D.; Raudonis, R.; Janulis, V. A Comparative Study of Phenolic Content in Apple Fruits. International Journal Food Prop 2015, 18(5), 945–953. DOI: 10.1080/10942912.2014.911311.
   Web of Science ®Google Scholar
• Nazaruk, J.; Borzym-Kluczyk, M. The Role of Triterpenes in the Management of Diabetes Mellitus and Its Complications. Phytochem Reviews 2015, 14(4), 675–690. DOI: 10.1007/s11101-014-9369-x.
   PubMed Web of Science ®Google Scholar
• Woźniak, Ł.; Skąpska, S.; Marszałek, K. Ursolic Acid - a Pentacyclic Triterpenoid with a Wide Spectrum of Pharmacological Activities. Molecules (Basel, Switzerland) 2015, 20(11), 20614–20641. DOI: 10.3390/molecules201119721.
   PubMed Web of Science ®Google Scholar
• Somova, L. O.; Nadar, A.; Rammanan, P.; Shode, F. O. Cardiovascular, Antihyperlipidemic and Antioxidant Effects of Oleanolic and Ursolic Acids in Experimental Hypertension. Phytomedicine : International Journal of Phytotherapy and Phytopharmacology 2003, 10(2–3), 115–121. DOI: 10.1078/094471103321659807.
   PubMed Web of Science ®Google Scholar
• Wolska, K.; Grudniak, A.; Fiecek, B.; Kraczkiewicz-Dowjat, A.; Kurek, A. Antibacterial Activity of Oleanolic and Ursolic Acids and Their Derivatives. Open Life Sciences 2010, 5, 5, 543–553.
   Web of Science ®Google Scholar
• Lesellier, E.; Destandau, E.; Grigoras, C.; Fougère, L.; Elfakir, C. Fast Separation of Triterpenoids by Supercritical Fluid Chromatography Evaporative Light Scattering Detector. Journal Chromatographic A 2012, 1268, 157–165. DOI: 10.1016/j.chroma.2012.09.102.
   PubMed Web of Science ®Google Scholar
• Naumoska, K.; Vovk, I. Analysis of Triterpenoids and Phytosterols in Vegetables by Thin–Layer Chromatography Coupled to Tandem Mass Spectrometry. Journal Chromatographic A 2015, 1381, 229–238. DOI: 10.1016/j.chroma.2015.01.001.
   PubMed Web of Science ®Google Scholar
• Ganzera, M.;. Quality Control of Herbal Medicines by Capillary Electrophoresis: Potential, Requirements and Applications. Electrophoresis 2008, 29, 3489–3503. DOI: 10.1002/elps.v29:17.
   PubMed Web of Science ®Google Scholar
• Li, G. L.; You, J. M.; Song, C. H.; Xia, L.; Zheng, J.; Suo, T. S. Development of a New HPLC Method with Precolumn Fluorescent Derivatization for Rapid, Selective and Sensitive Detection of Triterpenoid Acids in Fruits. Journal Agricultural Food Chemical 2011, 59, 2972–2979. DOI: 10.1021/jf104224t.
   PubMed Web of Science ®Google Scholar
• Boligon, A. A.; Athayde, M. L. Importance of HPLC in Analysis of Plants Extracts. Austin Chromatographic 2014, 1, 3, 2.
   Google Scholar
• Negi, J. S.; Singh, P.; Pant, G. J. N.; Rawat, M. S. M. High–Performance Liquid Chromatography Analysis of Plant Saponins: An Update 2005–2010. Pharmacogn Reviews 2011, 5(10), 155–158. DOI: 10.4103/0973-7847.91109.
   PubMedGoogle Scholar
• Andre, C. M.; Legay, S.; Deleruelle, A.; Nieuwenhuizen, N.; Punter, M.; Brendolise, C.; Cooney, J. M.; Lateur, M.; Hausman, J. F.; Larondelle, Y.; et al. Multifunctional Oxidosqualene Cyclases and Cytochrome P450 Involved in the Biosynthesis of Apple Fruit Triterpenoid Acids. The New Phytologist 2016, 211, 1279–1294. DOI: 10.1111/nph.13996.
   PubMed Web of Science ®Google Scholar
• He, X.; Liu, R. H. Phytochemicals of Apple Peels: Isolation, Structure Elucidation, and Their Antiproliferative and Antioxidant Activities. Journal of Agricultural and Food Chemistry 2008, 56, 9905–9910. DOI: 10.1021/jf8015255.
   PubMed Web of Science ®Google Scholar
• Fan, J. P.; Liao, D. D.; Zhang, X. H. Ultrasonic Assisted Extraction of Ursolic Acid from Apple Pomace: A Novel and Facile Technique. Sep Sciences Technological 2016, 51, 1344–1350. DOI: 10.1080/01496395.2016.1165253.
   Web of Science ®Google Scholar
• Plante, M.; Bailey, B.; Crafts, C.; Acworth, I. N. Sensitive HPLC Method for Triterpenoid Analysis Using Charged Aerosol Detection with Improved Resolution. Thermo Fisher Scientific 2012, 2–6.
   Google Scholar
• Andre, C. M.; Greenwood, J. M.; Walker, E. G.; Rassam, M.; Sullivan, M.; Evers, D.; Perry, N. B.; Laing, W. A. Anti–Inflammatory Procyanidins and Triterpenes in 109 Apple Varieties. Journal of Agricultural and Food Chemistry 2012, 60, 10546−10554. DOI: 10.1021/jf302809k.
   PubMed Web of Science ®Google Scholar
• Grigoras, C. G.; Destandaua, E.; Fougèrea, L.; Elfakira, C. Evaluation of Apple Pomace Extracts as a Source of Bioactive Compounds. Industrial Crops Products 2013, 49, 794–804. DOI: 10.1016/j.indcrop.2013.06.026.
   Web of Science ®Google Scholar
• Tostes, J. B. D. F.; Nakamura, M. J.; Gomes, C.; Saboya, F.; Mazzei, J. L.; Siani, A. C. Efficient and Selective Method to Separate Triterpene Acids by Direct Treatment of Apple Peels with Alkalin Ethanol. Sep Sciences Technological 2016, 51(12), 2–25. DOI: 10.1080/01496395.2016.1200088.
   Web of Science ®Google Scholar
• Moldoveanu, S. C.; Scott, W. A. Analysis of Four Pentacyclic Triterpenoid Acids in Several Bioactive Botanicals with Gas and Liquid Chromatography and Mass Spectrometry Detection. Journal Sep Sciences 2016, 39, 324–332. DOI: 10.1002/jssc.201501041.
   PubMed Web of Science ®Google Scholar
• Poirier, B. C.; Buchanan, D. A.; Mattheis, J.; Rudell, D. Differential Partitioning of Triterpenes and Triterpene Esters in Apple Peel. Journal of Agricultural and Food Chemistry 2018, 66(8), 1800–1806. DOI: 10.1021/acs.jafc.7b04509.
   PubMed Web of Science ®Google Scholar
• Sasidharan, S.; Chen, Y.; Saravanan, D.; Sundram, K. M.; Latha, L. Y. Extraction, Isolation and Characterization of Bioactive Compounds from Plants’ Extracts. African Journal Tradit Complementary Alternative Medica 2011, 8, 1, 1–10.
   PubMed Web of Science ®Google Scholar
• Pandey, A.; Tripathi, S. Concept of Standardization, Extraction and Pre Phytochemical Screening Strategies for Herbal Drug. Journal Pharmacogn Phytochem 2014, 2, 5, 115–119.
   Google Scholar
• Siani, A. C.; Nakamura, M. J.; Santos, D. S.; Mazzei, J. L.; Nascimento, A. C.; Valente, L. M. M. Efficiency and Selectivity of Triterpene Acid Extraction from Decoctions and Tinctures Prepared from Apple Peels. Pharmacogn. Mag. 2014, 10, 225–231. DOI: 10.4103/0973-1296.133294.
   Web of Science ®Google Scholar
• Tiwari, P.; Kumar, B.; Kaur, M.; Kaur, G.; Kaur, H. Phytochemical Screening and Extraction: A Review. International Pharmaceutical Sciences 2011, 1, 98–106.
   Google Scholar
• Cheok, C. H.; Salman, H. A. K.; Sulaiman, R. Extraction and Quantification of Saponins: A Review. Food Research International (Ottawa, Ont.) 2014, 59, 16–40. DOI: 10.1016/j.foodres.2014.01.057.
   Web of Science ®Google Scholar
• Handa, S. S.; Khanuja, S. P. S.; Longo, G.; Rakesh, D. D. Extraction Technologies for Medicinal and Aromatic Plants; International centre for science and high technology: Trieste, 2008, p. 25–33.
   Google Scholar
• Kataoka, H.;. New Trends in Sample Preparation for Analysis of Plant Derived Medicines. Current Organic Chemical 2010, 14, 1698–1713. DOI: 10.2174/138527210792927627.
   Web of Science ®Google Scholar
• Frighetto, R. T. S.; Welendorf, R. M.; Nigro, E. N.; Frighetto, N.; Siani, A. C. Isolation of Ursolic Acid from Apple Peels by High Speed Counter Current Chromatography. Food Chemistry 2008, 106, 767–771. DOI: 10.1016/j.foodchem.2007.06.003.
   Web of Science ®Google Scholar
• Baber, N.;. International Conference on Harmonisation of Technical Requirements for Registration of Pharmaceuticals for Human Use (ICH). British Journal Clinical Pharmacology 1994, 37(5), 401–404. DOI: 10.1111/j.1365-2125.1994.tb05705.x.
   PubMed Web of Science ®Google Scholar
• Jemmali, Z.; Chartiern, A.; Dufresne, C.; Elfakir, C. Optimization of the Derivatization Protocol of Pentacyclic Triterpenes Prior to Their Gas Chromatography – Mass Spectrometry Analysis in Plant Extracts. Talanta 2016, 147, 35–43. DOI: 10.1016/j.talanta.2015.09.026.
   PubMed Web of Science ®Google Scholar
• Jäger, S.; Trojan, H.; Kopp, T.; Laszczyk, M. N.; Scheffler, A. Pentacyclic Triterpene Distribution in Various Plants Rich Sources for a New Group of Multi Potent Plant Extracts. Molecules (Basel, Switzerland) 2009, 14, 2016–2031. DOI: 10.3390/molecules14031081.
   PubMed Web of Science ®Google Scholar
• Nour, V.; Trandafir, I.; Ionica, M. E. Compositional Characteristics of Fruits of Several Apple (Malus Domestica Borkh.) Cultivars. Not Botanic Hort Agrobot Cluj 2010, 38, 3, 228–233.
   Web of Science ®Google Scholar
• Szakiel, A.; Paczkowski, C.; Pensec, F.; Bertsch, C. Fruit Cuticular Waxes as a Source of Biologically Active Triterpenoids. Phytochemistry Reviews : Proceedings of the Phytochemical Society of Europe 2012, 11(2–3), 263–328. DOI: 10.1007/s11101-012-9241-9.
   PubMed Web of Science ®Google Scholar
• Cargnin, S. T.; Gnoatto, S. B. Ursolic Acid from Apple Pomace and Traditional Plants: A Valuable Triterpenoid with Functional Properties. Food Chemistry 2017, 220, 477–489. DOI: 10.1016/j.foodchem.2016.09.202.
   PubMed Web of Science ®Google Scholar
• He, Q. Q.; Yang, L.; Zhang, J. Y.; Ma, J. N.; Ma, C. M. Chemical Constituents of Gold–Red Apple and Their α–Glucosidase Inhibitory Activities. Journal of Food Science 2014, 79, 970–1983. DOI: 10.1111/1750-3841.12599.
   Web of Science ®Google Scholar
• Cortina, D. B.; Maci, A.; Iglesias, I.; Romero, M. P.; Motilva, M. J. Phytochemical Profiles of New Red–Fleshed Apple Varieties Compared with Traditional and New White Fleshed Varieties. Journal of Agricultural and Food Chemistry 2016, 5, 8, 1684–1696.
   Google Scholar
• Kukina, T. P.; Frolova, T. S.; Salnikova, O. I. Lipophilic Constituents from Malus Baccata. Chemical Natural Compd 2014, 6, 1096–1097. DOI: 10.1007/s10600-014-1168-5.
   Web of Science ®Google Scholar
• Ceymann, M.; Arrigoni, E.; Schärer, H.; Bozzi, N. A.; Hurrell, R. F. Identification of Apples Rich in Health-Promoting Flavan-3-Ols and Phenolic Acids by Measuring the Polyphenol Profile. Journal Food Compos Analysis 2012, 26(1), 128–135. DOI: 10.1016/j.jfca.2011.12.002.
   Web of Science ®Google Scholar
• Jeong, J. W.; Shim, J. J.; Choi, I. D.; Kim, S. H.; Ra, J.; Ku, H. K.; Lee, D. E.; Kim, T. Y.; Jeung, W.; Lee, J. H.;; et al. Apple Pomace Extract Improves Endurance in Exercise Performance by Increasing Strength and Weight of Skeletal Muscle. Journal Medica Food 2015, 18(12), 1380–1386.
   PubMed Web of Science ®Google Scholar
• Liaudanskas, M.; Brunevičiūtė, R.; Gaivelytė, K.; Viškelis, J.; Viškelis, P.; Kviklys, D.; Janulis, V. Seasonal Variation of Qualitative and Quantitative Composition of Phenolic Compounds and Antioxidant Activity in Apple (Malus Domestica Borkh.) Fruits. International Journal Biochemical Researcher Reviews 2016, 14(3), 1–13. DOI: 10.9734/IJBCRR/2016/28856.
   Google Scholar
• Kviklys, D.; Liaudanskas, M.; Janulis, V.; Viškelis, P.; Rubinskienė, M.; Lanauskas, J.; Uselis, N. Rootstock Genotype Determines Phenol Content in Apple Fruits. Plant, Soil Environment 2014, 60(5), 234–240. DOI: 10.17221/71/2014-PSE.
   Web of Science ®Google Scholar
• Viškelis, J.; Uselis, N.; Liaudanskas, M.; Janulis, V.; Bielicki, P.; Univer, T.; Lepsis, J.; Kviklys, D. Triterpenoid Acid Content in the Fruit Peel of Malus × Domestica Borkh. Depends on the Growing Technology. Zemdirbyste-Agriculture 2018, 105(1), 71–78. DOI: 10.13080/z-a.2018.105.010.
   Web of Science ®Google Scholar
• Lanauskas, J.; Kviklys, D.; Liaudanskas, M.; Janulis, V.; Uselis, N.; Viškelis, J.; Viškelis, P. Lower Nitrogen Nutrition Determines Higher Phenolic Content of Organic Apples. Hort Sciences 2017, 44, 3, 113–119.
   Web of Science ®Google Scholar