Ursolic acid: an overview including research performed in Peru
DOI:
https://doi.org/10.33936/rev_bas_de_la_ciencia.v6i1.3097Resumen
Ursolic acid (3β-3-hydroxy-urs-12-en-28-oic-acid) is a pentacyclic triterpenoid compound present in many medicinal herbs and edible fruits of different species of plants. Ursolic acid is now considered an important biomolecule due to its pharmacological activity and much of the research has focused on anticancer activity. To achieve the clinical application of ursolic acid, delivery nanosystems have been developed and the synthesis of its derivatives has also been carried out. In this review, we address different aspects of the chemistry of ursolic acid. Furthermore, we highlight the investigations that were carried out in Peru concerning ursolic acid. Palavras-chave: Ursolic acid, Triterpenoid, Lamiaceae, Medicinal plants. Abstract El ácido ursólico (ácido 3β-hidroxi-urs-12-en-28-óico) es un triterpenoide pentacíclico presente en varias hierbas medicinales y frutos comestibles de diferentes especies de plantas, es considerado una importante biomolécula debido a su actividad farmacológica y gran parte de las investigaciones se han enfocado en su actividad anticancerígena. Para lograr la aplicación clínica del ácido ursólico, se han desarrollado nanosistemas para su administración y también se han sintetizado gran cantidad de derivados. En esta revisión abordamos diferentes aspectos de la química del ácido ursólico, y además, destacamos las investigaciones que se llevaron a cabo en el Perú. Keywords: Ácido ursólico, Triterpenoide, Lamiaceae, Plantas medicinales.
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Abe, I. (2007). Enzymatic synthesis of cyclic triterpenes. Natural Product Reports, 24(6), 1311. https://doi.org/10.1039/b616857b
Adam, K.. P., Thiel, R., & Zapp, J. (1999). Incorporation of 1-[1-13C]Deoxy-d-xylulose in Chamomile Sesquiterpenes. Archives of Biochemistry and Biophysics, 369(1), 127-132. https://doi.org/10.1006/abbi.1999.1346
Babalola, I. T., & Shode, F. O. (2013). “Ubiquitous Ursolic Acid: A Potential Pentacyclic Triterpene Natural Product”. Journal of Pharmacognosy and Phytochemistry, 2(2), 2014-222.
Cárdenas, P. D., Almeida, A., & Bak, S. (2019). Evolution of Structural Diversity of Triterpenoids. Frontiers in Plant Science, 10, 1523. https://doi.org/10.3389/fpls.2019.01523
Chan, E. W. C., Soon, C. Y., Tan, J. B. L., Wong, S. K., & Hui, Y. W. (2019). Ursolic acid: An overview on its cytotoxic activities against breast and colorectal cancer cells. Journal of Integrative Medicine, 17(3), 155-160. https://doi.org/10.1016/j.joim.2019.03.003
Chappell, J. (2002). The genetics and molecular genetics of terpene and sterol origami. Current Opinion in Plant Biology, 5(2), 151-157. https://doi.org/10.1016/S1369-5266(02)00241-8
Fajardo-Sánchez, E., Galiano, V., & Villalaín, J. (2017). Location of the bioactive pentacyclic triterpene ursolic acid in the membrane. A molecular dynamics study. Journal of Biomolecular Structure and Dynamics, 35(12), 2688-2700. https://doi.org/10.1080/07391102.2016.1229219
Fan, J. P., Kong, T., Zhang, L., Tong, S., Tian, Z. Y., Duan, Y. H., & Zhang, X. H. (2011). Solubilities of Ursolic Acid and Oleanolic Acid in Four Solvents from (283.2 to 329.7) K. Journal of Chemical & Engineering Data, 56(5), 2723-2725. https://doi.org/10.1021/je101309a
Fan, J. P., Liao, D. D., & Zhang, X. H. (2016). Ultrasonic assisted extraction of ursolic acid from apple pomace: A novel and facile technique. Separation Science and Technology, 51(8), 1344-1350. https://doi.org/10.1080/01496395.2016.1165253
Feng, Y., Wei, Z., & Zhang, J. (2020). Determination of Ursolic Acid in Extracts From Ligustri lucidum Fruit Using an Electrochemical Method. Frontiers in Chemistry, 8, 444. https://doi.org/10.3389/fchem.2020.00444
Gao, R., Wang, L., Yang, Y., Ni, J., Zhao, L., Dong, S., & Guo, M. (2015). Simultaneous determination of oleanolic acid, ursolic acid, quercetin and apigenin in Swertia mussotii Franch by capillary zone electrophoresis with running buffer modifier: Determination of four componets in S. mussotii Franch by CZE. Biomedical Chromatography, 29(3), 402-409. https://doi.org/10.1002/bmc.3290
Ghosh, S. (2017). Triterpene Structural Diversification by Plant Cytochrome P450 Enzymes. Frontiers in Plant Science, 8, 1886. https://doi.org/10.3389/fpls.2017.01886
Habtemariam, S. (2019). Antioxidant and Anti-inflammatory Mechanisms of Neuroprotection by Ursolic Acid: Addressing Brain Injury, Cerebral Ischemia, Cognition Deficit, Anxiety, and Depression. Oxidative Medicine and Cellular Longevity, 2019, 1-18. https://doi.org/10.1155/2019/8512048
Herrera-Añazco, P., Taype-Rondan, A., Ortiz, P. J., Málaga, G., del Carpio-Toia, A. M., Alvarez-Valdivia, M. G., Juárez- Huanca, C., Ciudad- Fernandez, L., Bruner- Meléndez, R., Samaniego- Mojica, W., & Perez- Rafael, E. (2019). Use of medicinal plants in patients with chronic kidney disease from Peru. Complementary Therapies in Medicine, 47, 102215. https://doi.org/10.1016/j.ctim.2019.102215
Hodon, J., Borkova, L., Pokorny, J., Kazakova, A., & Urban, M. (2019). Design and synthesis of pentacyclic triterpene conjugates and their use in medicinal research. European Journal of Medicinal Chemistry, 182, 111653. https://doi.org/10.1016/j.ejmech.2019.111653
Jäger, S., Trojan, H., Kopp, T., Laszczyk, M., & Scheffler, A. (2009). Pentacyclic Triterpene Distribution in Various Plants - Rich Sources for a New Group of Multi-Potent Plant Extracts. Molecules, 14(6), 2016-2031. https://doi.org/10.3390/molecules14062016
Jamal, M., Amir, M., Ali, Z., & Mujeeb, M. (2018). A comparative study for the extraction methods and solvent selection for isolation, quantitative estimation and validation of ursolic acid in the leaves of Lantana camara by HPTLC method. Future Journal of Pharmaceutical Sciences, 4(2), 229-233. https://doi.org/10.1016/j.fjps.2018.07.002
Janicsák, G., Veres, K., Zoltán Kakasy, A., & Máthé, I. (2006). Study of the oleanolic and ursolic acid contents of some species of the Lamiaceae. Biochemical Systematics and Ecology, 34(5), 392-396. https://doi.org/10.1016/j.bse.2005.12.004
Jemmali, Z., Chartier, A., Dufresne, C., & Elfakir, C. (2016). Optimization of the derivatization protocol of pentacyclic triterpenes prior to their gas chromatography-mass spectrometry analysis in plant extracts. Talanta, 147, 35-43. https://doi.org/10.1016/j.talanta.2015.09.026
Jyoti, M. A., Nam, K.. W., Jang, W. S., Kim, Y. H., Kim, S. K., Lee, B. E., & Song, H. Y. (2016). Antimycobacterial activity of methanolic plant extract of Artemisia capillaris containing ursolic acid and hydroquinone against Mycobacterium tuberculosis. Journal of Infection and Chemotherapy, 22(4), 200-208. https://doi.org/10.1016/j.jiac.2015.11.014
Kartini, Piyaviriyakul, S., Siripong, P., & Vallisuta, O. (2014). HPTLC simultaneous quantification of triterpene acids for quality control of Plantago major L. and evaluation of their cytotoxic and antioxidant activities. Industrial Crops and Products, 60, 239-246. https://doi.org/10.1016/j.indcrop.2014.06.020
Kashyap, D., Tuli, H. S., & Sharma, A. K. (2016). Ursolic acid (UA): A metabolite with promising therapeutic potential. Life Sciences, 146, 201-213. https://doi.org/10.1016/j.lfs.2016.01.017
Kawano, M., Otsuka, M., Umeyama, K., Yamazaki, M., Shiota, T., Satake, M., & Okuyama, E. (2009). Anti-inflammatory and analgesic components from “hierba santa,” a traditional medicine in Peru. Journal of Natural Medicines, 63(2), 147-158. https://doi.org/10.1007/s11418-008-0302-8
Khwaza, V., Oyedeji, O. O., & Aderibigbe, B. A. (2020). Ursolic Acid-Based Derivatives as Potential Anti-Cancer Agents: An Update. International Journal of Molecular Sciences, 21(16), 5920. https://doi.org/10.3390/ijms21165920
Kontogianni, V. G., Exarchou, V., Troganis, A., & Gerothanassis, I. P. (2009). Rapid and novel discrimination and quantification of oleanolic and ursolic acids in complex plant extracts using two-dimensional nuclear magnetic resonance spectroscopy-Comparison with HPLC methods. Analytica Chimica Acta, 635(2), 188-195. https://doi.org/10.1016/j.aca.2009.01.021
Lacikova, L., Abdel-Hamid, M. E., Novotny, L., Masterova, I., & Grancai, D. (2006). A Rapid Tandem Mass Spectrometric Assay for Determination of Ursolic Acid – Application to Analysis of Ursolic Acid in Four Species of Staphylea L. and Leaves of Staphylea Pinnata L. Gathered During Ontogenesis. Chromatographia, 63(3-4), 117-122. https://doi.org/10.1365/s10337-006-0724-y
Li, P., Liu, A., Li, Y., Yuan, B., Xiao, W., Liu, Z., Zhang, S., & Lin, H. (2019). Development and Validation of an Analytical Method Based on HPLC-ELSD for the Simultaneous Determination of Rosmarinic Acid, Carnosol, Carnosic Acid, Oleanolic Acid and Ursolic Acid in Rosemary. Molecules, 24(2), 323. https://doi.org/10.3390/molecules24020323
López-Hortas, L., Pérez-Larrán, P., González-Muñoz, M. J., Falqué, E., & Domínguez, H. (2018). Recent developments on the extraction and application of ursolic acid. A review. Food Research International, 103, 130-149. https://doi.org/10.1016/j.foodres.2017.10.028
Lu, C., Zhang, C., Zhao, F., Li, D., & Lu, W. (2018). Biosynthesis of ursolic acid and oleanolic acid in Saccharomyces cerevisiae. AIChE Journal, 64(11), 3794-3802. https://doi.org/10.1002/aic.16370
Ludeña-Huaman, M. A and Tupa-Quispe, A. L. (2017) “Aislamiento y cuantificación del ácido ursólico de Clinopodium revolutum (Flor de Arena)”, [Tesis de grado, Universidad Nacional de San Antonio Abad del Cusco]. http://repositorio.unsaac.edu.pe/handle/UNSAAC/2703
Ludeña-Huaman, M. A. (2018). Método preparativo para la obtención de ácido ursólico a partir de Clinopodium revolutum. Revista Colombiana de Química, 47(1), 10-15. https://doi.org/10.15446/rev.colomb.quim.v47n1.65375
Ludeña-Huaman, M. A., & Ramos-Inquiltupa, D. A. (2019). Determination of the content of ursolic and oleanolic acid in the cuticular wax of fruits of different species of Rosaceae. Revista Colombiana de Química, 48(2), 15-20. https://doi.org/10.15446/rev.colomb.quim.v48n2.77046
Martelanc, M., Naumoska, K., & Vovk, I. (2016). Determination of common triterpenoids and phytosterols in vegetable waxes by HPTLC-densitometry and HPTLC-image analysis. Journal of Liquid Chromatography & Related Technologies, 39(5-6), 312-321. https://doi.org/10.1080/10826076.2016.1165576
Miziorko, H. M. (2011). Enzymes of the mevalonate pathway of isoprenoid biosynthesis. Archives of Biochemistry and Biophysics, 505(2), 131-143. https://doi.org/10.1016/j.abb.2010.09.028
Mostacero, J., Mejía, F., Gastañadui, D., & De La Cruz, J. (2017). Taxonomic, phytogeographic, and ethnobotanical inventory of native fruit trees of northern Peru. Scientia Agropecuaria, 8(3), 215-224. https://doi.org/10.17268/sci.agropecu.2017.03.04
Mučaji, P., & Nagy, M. (2011). Contribution to the TLC separation of ursolic and oleanolic acid mixture. Acta Facultatis Pharmaceuticae Universitatis Comenianae, 58(1), 56-61. https://doi.org/10.2478/v10219-011-0006-0
Neto, C. C., Vaisberg, A. J., Zhou, B.-N., Kingston, D. G. I., & Hammond, G. B. (2000). Cytotoxic Triterpene Acids from the Peruvian Medicinal Plant Polylepis racemosa. Planta Medica, 66(5), 483-484. https://doi.org/10.1055/s-2000-8583
Numonov, S., Sharopov, F., Qureshi, M. N., Gaforzoda, L., Gulmurodov, I., Khalilov, Q., Setzer, W. N., Habasi, M., & Aisa, H. A. (2020). The Ursolic Acid-Rich Extract of Dracocephalum heterophyllum Benth. With Potent Antidiabetic and Cytotoxic Activities. Applied Sciences, 10(18), 6505. https://doi.org/10.3390/app10186505
Oancea, I. A., van Staden, J. (Koos) F., Oancea, E., & Ungureanu, E. M. (2019). Electrochemical detection of ursolic acid from spruce (Picea abies) essential oils using modified amperometric microsensors. Analytical Letters, 52(14), 2214-2226. https://doi.org/10.1080/00032719.2019.1605373
Odonne, G., Herbette, G., Eparvier, V., Bourdy, G., Rojas, R., Sauvain, M., & Stien, D. (2011). Antileishmanial sesquiterpene lactones from Pseudelephantopus spicatus, a traditional remedy from the Chayahuita Amerindians (Peru). Part III. Journal of Ethnopharmacology, 137(1), 875-879. https://doi.org/10.1016/j.jep.2011.07.008
Palu, D., Bighelli, A., Casanova, J., & Paoli, M. (2019). Identification and Quantitation of Ursolic and Oleanolic Acids in Ilex aquifolium L. Leaf Extracts Using 13C and 1H-NMR Spectroscopy. Molecules, 24(23), 4413. https://doi.org/10.3390/molecules24234413
Phillips, D. R., Rasbery, J. M., Bartel, B., & Matsuda, S. P. (2006). Biosynthetic diversity in plant triterpene cyclization. Current Opinion in Plant Biology, 9(3), 305-314. https://doi.org/10.1016/j.pbi.2006.03.004
Pironi, A. M., de Araújo, P. R., Fernandes, M. A., Salgado, H. R. N., & Chorilli, M. (2018). Characteristics, Biological Properties and Analytical Methods of Ursolic Acid: A Review. Critical Reviews in Analytical Chemistry, 48(1), 86-93. https://doi.org/10.1080/10408347.2017.1390425
Qian, Z., Wang, X., Song, Z., Zhang, H., Zhou, S., Zhao, J., & Wang, H. (2015). A Phase I Trial to Evaluate the Multiple-Dose Safety and Antitumor Activity of Ursolic Acid Liposomes in Subjects with Advanced Solid Tumors. BioMed Research International, 2015, 1-7. https://doi.org/10.1155/2015/809714
Razboršek, M. I., Vončina, D. B., Doleček, V., & Vončina, E. (2008). Determination of Oleanolic, Betulinic and Ursolic Acid in Lamiaceae and Mass Spectral Fragmentation of Their Trimethylsilylated Derivatives. Chromatographia, 67(5-6), 433-440. https://doi.org/10.1365/s10337-008-0533-6
Rodriguez, M. (2013). Lamiaceae endémicas del Perú. Revista Peruana de Biología, 13(2), 371-379. https://doi.org/10.15381/rpb.v13i2.1868
Seki, H., Tamura, K., & Muranaka, T. (2015). P450s and UGTs: Key Players in the Structural Diversity of Triterpenoid Saponins. Plant and Cell Physiology, 56(8), 1463-1471. https://doi.org/10.1093/pcp/pcv062
Serrano Flores, C. A., Curie, B. C., Quispe Tupa, A. L., Huamán Quispe, R. I., & Ludeña Huaman, M. A. (2016). Cuantificación de ácido oleanólico, ácido ursólico y ácido rosmarínico en tres especies peruanas de Clinopodium (Lamiaceae, Nepetoideae, Mentheae). Arnaldoa, 23(1), 333-350.
Serrano Flores, Carlos Alberto, Villena Chávez, Gretty Katherina, & Rodríguez Rodríguez, Eric F. (2020). Some phytochemical components and antioxidant activity in representatives of the Mentheae tribe (Lamiaceae) of Peru. Arnaldoa, 27(1), 169-180. https://dx.doi.org/10.22497/arnaldoa.271.27109
Shao, J., Fang, Y., Zhao, R., Chen, F., Yang, M., Jiang, J., Chen, Z., Yuan, X., & Jia, L. (2020). Evolution from small molecule to nano-drug delivery systems: An emerging approach for cancer therapy of ursolic acid. Asian Journal of Pharmaceutical Sciences, 15(6), 685-700. https://doi.org/10.1016/j.ajps.2020.03.001
Silva, M. G., Vieira, I., Mendes, F., Albuquerque, I., Dos Santos, R., Silva, F., & Morais, S. (2008). Variation of Ursolic Acid Content in Eight Ocimum Species from Northeastern Brazil. Molecules, 13(10), 2482-2487. https://doi.org/10.3390/molecules13102482
Soares, D. B. S., Duarte, L. P., Cavalcanti, A. D., Silva, F. C., Braga, A. D., Lopes, M. T. P., Takahashi, J. A., & Vieira-Filho, S. A. (2017). Psychotria viridis: Chemical constituents from leaves and biological properties. Anais Da Academia Brasileira de Ciências, 89(2), 927-938. https://doi.org/10.1590/0001-3765201720160411
Srisawat, P., Fukushima, E. O., Yasumoto, S., Robertlee, J., Suzuki, H., Seki, H., & Muranaka, T. (2019). Identification of oxidosqualene cyclases from the medicinal legume tree Bauhinia forficata: A step toward discovering preponderant α‐amyrin‐producing activity. New Phytologist, 224(1), 352-366. https://doi.org/10.1111/nph.16013
Suzuki, H., Fukushima, E. O., Shimizu, Y., Seki, H., Fujisawa, Y., Ishimoto, M., Osakabe, K., Osakabe, Y., & Muranaka, T. (2019). Lotus japonicus Triterpenoid Profile and Characterization of the CYP716A51 and LjCYP93E1 Genes Involved in Their Biosynthesis In Planta. Plant and Cell Physiology, 60(11), 2496-2509. https://doi.org/10.1093/pcp/pcz145
Szakiel, A., Pączkowski, C., Pensec, F., & Bertsch, C. (2012). Fruit cuticular waxes as a source of biologically active triterpenoids. Phytochemistry Reviews, 11(2-3), 263-284. https://doi.org/10.1007/s11101-012-9241-9
Thimmappa, R., Geisler, K., Louveau, T., O’Maille, P., & Osbourn, A. (2014). Triterpene Biosynthesis in Plants. Annual Review of Plant Biology, 65(1), 225-257. https://doi.org/10.1146/annurev-arplant-050312-120229
Tyszczuk-Rotko, K., Domańska, K., Sadok, I., Wójciak-Kosior, M., & Sowa, I. (2015). Voltammetric procedure for the determination of oleanolic and ursolic acids in plant extracts. Analytical Methods, 7(22), 9435-9441. https://doi.org/10.1039/C5AY01976A
Uddin, G., Siddiqui, B. S., Alam, M., Sadat, A., Ahmad, A., & Uddin, A. (2011). Chemical Constituents and Phytotoxicity of Solvent Extracted Fractions of Stem Bark of Grewia optiva Drummond ex Burret, 8(1), 85-91.
Vetal, M. D., Shirpurkar, N. D., & Rathod, V. K. (2014). Three phase partitioning coupled with ultrasound for the extraction of ursolic acid and oleanolic acid from Ocimum sanctum. Food and Bioproducts Processing, 92(4), 402-408. https://doi.org/10.1016/j.fbp.2013.09.002
Vo, N. N. Q., Nomura, Y., Muranaka, T., & Fukushima, E. O. (2019). Structure–Activity Relationships of Pentacyclic Triterpenoids as Inhibitors of Cyclooxygenase and Lipoxygenase Enzymes. Journal of Natural Products, 82(12), 3311-3320. https://doi.org/10.1021/acs.jnatprod.9b00538
Wei, Z. Y., Chi, K. Q., Wang, K.. S., Wu, J., Liu, L. P., & Piao, H. R. (2018). Design, synthesis, evaluation, and molecular docking of ursolic acid derivatives containing a nitrogen heterocycle as anti-inflammatory agents. Bioorganic & Medicinal Chemistry Letters, 28(10), 1797-1803. https://doi.org/10.1016/j.bmcl.2018.04.021
Winiewski, V., Serain, A., Sá, E., Salvador, M., & Stefanello, M. É. (2020). Chemical constituents of Sinningia mauroana and screening of its extracts for antimicrobial, antioxidant and cytotoxic activities. Química Nova. https://doi.org/10.21577/0100-4042.20170478
Xu, R., Fazio, G. C., & Matsuda, S. P. T. (2004). On the origins of triterpenoid skeletal diversity. Phytochemistry, 65(3), 261-291. https://doi.org/10.1016/j.phytochem.2003.11.014
Yang, P., Li, Y., Liu, X., & Jiang, S. (2007). Determination of free isomeric oleanolic acid and ursolic acid in Pterocephalus hookeri by capillary zone electrophoresis. Journal of Pharmaceutical and Biomedical Analysis, 43(4), 1331-1334. https://doi.org/10.1016/j.jpba.2006.10.042
Yao, L., Lu, J., Wang, J., & Gao, W. Y. (2020). Advances in biosynthesis of triterpenoid saponins in medicinal plants. Chinese Journal of Natural Medicines, 18(6), 417-424. https://doi.org/10.1016/S1875-5364(20)30049-2
Zhou, M., Zhang, R. H., Wang, M., Xu, G. B., & Liao, S. G. (2017). Prodrugs of triterpenoids and their derivatives. European Journal of Medicinal Chemistry, 131, 222-236. https://doi.org/10.1016/j.ejmech.2017.03.005
Zhou, Z., Tong, H. H. Y., Li, L., Shek, F. L. Y., Lv, Y., & Zheng, Y. (2015). Synthesis, characterization and thermal analysis of ursolic acid solid forms: Synthesis, characterization and thermal analysis of ursolic acid solid forms. Crystal Research and Technology, 50(7), 538-548. https://doi.org/10.1002/crat.201500034
Adam, K.. P., Thiel, R., & Zapp, J. (1999). Incorporation of 1-[1-13C]Deoxy-d-xylulose in Chamomile Sesquiterpenes. Archives of Biochemistry and Biophysics, 369(1), 127-132. https://doi.org/10.1006/abbi.1999.1346
Babalola, I. T., & Shode, F. O. (2013). “Ubiquitous Ursolic Acid: A Potential Pentacyclic Triterpene Natural Product”. Journal of Pharmacognosy and Phytochemistry, 2(2), 2014-222.
Cárdenas, P. D., Almeida, A., & Bak, S. (2019). Evolution of Structural Diversity of Triterpenoids. Frontiers in Plant Science, 10, 1523. https://doi.org/10.3389/fpls.2019.01523
Chan, E. W. C., Soon, C. Y., Tan, J. B. L., Wong, S. K., & Hui, Y. W. (2019). Ursolic acid: An overview on its cytotoxic activities against breast and colorectal cancer cells. Journal of Integrative Medicine, 17(3), 155-160. https://doi.org/10.1016/j.joim.2019.03.003
Chappell, J. (2002). The genetics and molecular genetics of terpene and sterol origami. Current Opinion in Plant Biology, 5(2), 151-157. https://doi.org/10.1016/S1369-5266(02)00241-8
Fajardo-Sánchez, E., Galiano, V., & Villalaín, J. (2017). Location of the bioactive pentacyclic triterpene ursolic acid in the membrane. A molecular dynamics study. Journal of Biomolecular Structure and Dynamics, 35(12), 2688-2700. https://doi.org/10.1080/07391102.2016.1229219
Fan, J. P., Kong, T., Zhang, L., Tong, S., Tian, Z. Y., Duan, Y. H., & Zhang, X. H. (2011). Solubilities of Ursolic Acid and Oleanolic Acid in Four Solvents from (283.2 to 329.7) K. Journal of Chemical & Engineering Data, 56(5), 2723-2725. https://doi.org/10.1021/je101309a
Fan, J. P., Liao, D. D., & Zhang, X. H. (2016). Ultrasonic assisted extraction of ursolic acid from apple pomace: A novel and facile technique. Separation Science and Technology, 51(8), 1344-1350. https://doi.org/10.1080/01496395.2016.1165253
Feng, Y., Wei, Z., & Zhang, J. (2020). Determination of Ursolic Acid in Extracts From Ligustri lucidum Fruit Using an Electrochemical Method. Frontiers in Chemistry, 8, 444. https://doi.org/10.3389/fchem.2020.00444
Gao, R., Wang, L., Yang, Y., Ni, J., Zhao, L., Dong, S., & Guo, M. (2015). Simultaneous determination of oleanolic acid, ursolic acid, quercetin and apigenin in Swertia mussotii Franch by capillary zone electrophoresis with running buffer modifier: Determination of four componets in S. mussotii Franch by CZE. Biomedical Chromatography, 29(3), 402-409. https://doi.org/10.1002/bmc.3290
Ghosh, S. (2017). Triterpene Structural Diversification by Plant Cytochrome P450 Enzymes. Frontiers in Plant Science, 8, 1886. https://doi.org/10.3389/fpls.2017.01886
Habtemariam, S. (2019). Antioxidant and Anti-inflammatory Mechanisms of Neuroprotection by Ursolic Acid: Addressing Brain Injury, Cerebral Ischemia, Cognition Deficit, Anxiety, and Depression. Oxidative Medicine and Cellular Longevity, 2019, 1-18. https://doi.org/10.1155/2019/8512048
Herrera-Añazco, P., Taype-Rondan, A., Ortiz, P. J., Málaga, G., del Carpio-Toia, A. M., Alvarez-Valdivia, M. G., Juárez- Huanca, C., Ciudad- Fernandez, L., Bruner- Meléndez, R., Samaniego- Mojica, W., & Perez- Rafael, E. (2019). Use of medicinal plants in patients with chronic kidney disease from Peru. Complementary Therapies in Medicine, 47, 102215. https://doi.org/10.1016/j.ctim.2019.102215
Hodon, J., Borkova, L., Pokorny, J., Kazakova, A., & Urban, M. (2019). Design and synthesis of pentacyclic triterpene conjugates and their use in medicinal research. European Journal of Medicinal Chemistry, 182, 111653. https://doi.org/10.1016/j.ejmech.2019.111653
Jäger, S., Trojan, H., Kopp, T., Laszczyk, M., & Scheffler, A. (2009). Pentacyclic Triterpene Distribution in Various Plants - Rich Sources for a New Group of Multi-Potent Plant Extracts. Molecules, 14(6), 2016-2031. https://doi.org/10.3390/molecules14062016
Jamal, M., Amir, M., Ali, Z., & Mujeeb, M. (2018). A comparative study for the extraction methods and solvent selection for isolation, quantitative estimation and validation of ursolic acid in the leaves of Lantana camara by HPTLC method. Future Journal of Pharmaceutical Sciences, 4(2), 229-233. https://doi.org/10.1016/j.fjps.2018.07.002
Janicsák, G., Veres, K., Zoltán Kakasy, A., & Máthé, I. (2006). Study of the oleanolic and ursolic acid contents of some species of the Lamiaceae. Biochemical Systematics and Ecology, 34(5), 392-396. https://doi.org/10.1016/j.bse.2005.12.004
Jemmali, Z., Chartier, A., Dufresne, C., & Elfakir, C. (2016). Optimization of the derivatization protocol of pentacyclic triterpenes prior to their gas chromatography-mass spectrometry analysis in plant extracts. Talanta, 147, 35-43. https://doi.org/10.1016/j.talanta.2015.09.026
Jyoti, M. A., Nam, K.. W., Jang, W. S., Kim, Y. H., Kim, S. K., Lee, B. E., & Song, H. Y. (2016). Antimycobacterial activity of methanolic plant extract of Artemisia capillaris containing ursolic acid and hydroquinone against Mycobacterium tuberculosis. Journal of Infection and Chemotherapy, 22(4), 200-208. https://doi.org/10.1016/j.jiac.2015.11.014
Kartini, Piyaviriyakul, S., Siripong, P., & Vallisuta, O. (2014). HPTLC simultaneous quantification of triterpene acids for quality control of Plantago major L. and evaluation of their cytotoxic and antioxidant activities. Industrial Crops and Products, 60, 239-246. https://doi.org/10.1016/j.indcrop.2014.06.020
Kashyap, D., Tuli, H. S., & Sharma, A. K. (2016). Ursolic acid (UA): A metabolite with promising therapeutic potential. Life Sciences, 146, 201-213. https://doi.org/10.1016/j.lfs.2016.01.017
Kawano, M., Otsuka, M., Umeyama, K., Yamazaki, M., Shiota, T., Satake, M., & Okuyama, E. (2009). Anti-inflammatory and analgesic components from “hierba santa,” a traditional medicine in Peru. Journal of Natural Medicines, 63(2), 147-158. https://doi.org/10.1007/s11418-008-0302-8
Khwaza, V., Oyedeji, O. O., & Aderibigbe, B. A. (2020). Ursolic Acid-Based Derivatives as Potential Anti-Cancer Agents: An Update. International Journal of Molecular Sciences, 21(16), 5920. https://doi.org/10.3390/ijms21165920
Kontogianni, V. G., Exarchou, V., Troganis, A., & Gerothanassis, I. P. (2009). Rapid and novel discrimination and quantification of oleanolic and ursolic acids in complex plant extracts using two-dimensional nuclear magnetic resonance spectroscopy-Comparison with HPLC methods. Analytica Chimica Acta, 635(2), 188-195. https://doi.org/10.1016/j.aca.2009.01.021
Lacikova, L., Abdel-Hamid, M. E., Novotny, L., Masterova, I., & Grancai, D. (2006). A Rapid Tandem Mass Spectrometric Assay for Determination of Ursolic Acid – Application to Analysis of Ursolic Acid in Four Species of Staphylea L. and Leaves of Staphylea Pinnata L. Gathered During Ontogenesis. Chromatographia, 63(3-4), 117-122. https://doi.org/10.1365/s10337-006-0724-y
Li, P., Liu, A., Li, Y., Yuan, B., Xiao, W., Liu, Z., Zhang, S., & Lin, H. (2019). Development and Validation of an Analytical Method Based on HPLC-ELSD for the Simultaneous Determination of Rosmarinic Acid, Carnosol, Carnosic Acid, Oleanolic Acid and Ursolic Acid in Rosemary. Molecules, 24(2), 323. https://doi.org/10.3390/molecules24020323
López-Hortas, L., Pérez-Larrán, P., González-Muñoz, M. J., Falqué, E., & Domínguez, H. (2018). Recent developments on the extraction and application of ursolic acid. A review. Food Research International, 103, 130-149. https://doi.org/10.1016/j.foodres.2017.10.028
Lu, C., Zhang, C., Zhao, F., Li, D., & Lu, W. (2018). Biosynthesis of ursolic acid and oleanolic acid in Saccharomyces cerevisiae. AIChE Journal, 64(11), 3794-3802. https://doi.org/10.1002/aic.16370
Ludeña-Huaman, M. A and Tupa-Quispe, A. L. (2017) “Aislamiento y cuantificación del ácido ursólico de Clinopodium revolutum (Flor de Arena)”, [Tesis de grado, Universidad Nacional de San Antonio Abad del Cusco]. http://repositorio.unsaac.edu.pe/handle/UNSAAC/2703
Ludeña-Huaman, M. A. (2018). Método preparativo para la obtención de ácido ursólico a partir de Clinopodium revolutum. Revista Colombiana de Química, 47(1), 10-15. https://doi.org/10.15446/rev.colomb.quim.v47n1.65375
Ludeña-Huaman, M. A., & Ramos-Inquiltupa, D. A. (2019). Determination of the content of ursolic and oleanolic acid in the cuticular wax of fruits of different species of Rosaceae. Revista Colombiana de Química, 48(2), 15-20. https://doi.org/10.15446/rev.colomb.quim.v48n2.77046
Martelanc, M., Naumoska, K., & Vovk, I. (2016). Determination of common triterpenoids and phytosterols in vegetable waxes by HPTLC-densitometry and HPTLC-image analysis. Journal of Liquid Chromatography & Related Technologies, 39(5-6), 312-321. https://doi.org/10.1080/10826076.2016.1165576
Miziorko, H. M. (2011). Enzymes of the mevalonate pathway of isoprenoid biosynthesis. Archives of Biochemistry and Biophysics, 505(2), 131-143. https://doi.org/10.1016/j.abb.2010.09.028
Mostacero, J., Mejía, F., Gastañadui, D., & De La Cruz, J. (2017). Taxonomic, phytogeographic, and ethnobotanical inventory of native fruit trees of northern Peru. Scientia Agropecuaria, 8(3), 215-224. https://doi.org/10.17268/sci.agropecu.2017.03.04
Mučaji, P., & Nagy, M. (2011). Contribution to the TLC separation of ursolic and oleanolic acid mixture. Acta Facultatis Pharmaceuticae Universitatis Comenianae, 58(1), 56-61. https://doi.org/10.2478/v10219-011-0006-0
Neto, C. C., Vaisberg, A. J., Zhou, B.-N., Kingston, D. G. I., & Hammond, G. B. (2000). Cytotoxic Triterpene Acids from the Peruvian Medicinal Plant Polylepis racemosa. Planta Medica, 66(5), 483-484. https://doi.org/10.1055/s-2000-8583
Numonov, S., Sharopov, F., Qureshi, M. N., Gaforzoda, L., Gulmurodov, I., Khalilov, Q., Setzer, W. N., Habasi, M., & Aisa, H. A. (2020). The Ursolic Acid-Rich Extract of Dracocephalum heterophyllum Benth. With Potent Antidiabetic and Cytotoxic Activities. Applied Sciences, 10(18), 6505. https://doi.org/10.3390/app10186505
Oancea, I. A., van Staden, J. (Koos) F., Oancea, E., & Ungureanu, E. M. (2019). Electrochemical detection of ursolic acid from spruce (Picea abies) essential oils using modified amperometric microsensors. Analytical Letters, 52(14), 2214-2226. https://doi.org/10.1080/00032719.2019.1605373
Odonne, G., Herbette, G., Eparvier, V., Bourdy, G., Rojas, R., Sauvain, M., & Stien, D. (2011). Antileishmanial sesquiterpene lactones from Pseudelephantopus spicatus, a traditional remedy from the Chayahuita Amerindians (Peru). Part III. Journal of Ethnopharmacology, 137(1), 875-879. https://doi.org/10.1016/j.jep.2011.07.008
Palu, D., Bighelli, A., Casanova, J., & Paoli, M. (2019). Identification and Quantitation of Ursolic and Oleanolic Acids in Ilex aquifolium L. Leaf Extracts Using 13C and 1H-NMR Spectroscopy. Molecules, 24(23), 4413. https://doi.org/10.3390/molecules24234413
Phillips, D. R., Rasbery, J. M., Bartel, B., & Matsuda, S. P. (2006). Biosynthetic diversity in plant triterpene cyclization. Current Opinion in Plant Biology, 9(3), 305-314. https://doi.org/10.1016/j.pbi.2006.03.004
Pironi, A. M., de Araújo, P. R., Fernandes, M. A., Salgado, H. R. N., & Chorilli, M. (2018). Characteristics, Biological Properties and Analytical Methods of Ursolic Acid: A Review. Critical Reviews in Analytical Chemistry, 48(1), 86-93. https://doi.org/10.1080/10408347.2017.1390425
Qian, Z., Wang, X., Song, Z., Zhang, H., Zhou, S., Zhao, J., & Wang, H. (2015). A Phase I Trial to Evaluate the Multiple-Dose Safety and Antitumor Activity of Ursolic Acid Liposomes in Subjects with Advanced Solid Tumors. BioMed Research International, 2015, 1-7. https://doi.org/10.1155/2015/809714
Razboršek, M. I., Vončina, D. B., Doleček, V., & Vončina, E. (2008). Determination of Oleanolic, Betulinic and Ursolic Acid in Lamiaceae and Mass Spectral Fragmentation of Their Trimethylsilylated Derivatives. Chromatographia, 67(5-6), 433-440. https://doi.org/10.1365/s10337-008-0533-6
Rodriguez, M. (2013). Lamiaceae endémicas del Perú. Revista Peruana de Biología, 13(2), 371-379. https://doi.org/10.15381/rpb.v13i2.1868
Seki, H., Tamura, K., & Muranaka, T. (2015). P450s and UGTs: Key Players in the Structural Diversity of Triterpenoid Saponins. Plant and Cell Physiology, 56(8), 1463-1471. https://doi.org/10.1093/pcp/pcv062
Serrano Flores, C. A., Curie, B. C., Quispe Tupa, A. L., Huamán Quispe, R. I., & Ludeña Huaman, M. A. (2016). Cuantificación de ácido oleanólico, ácido ursólico y ácido rosmarínico en tres especies peruanas de Clinopodium (Lamiaceae, Nepetoideae, Mentheae). Arnaldoa, 23(1), 333-350.
Serrano Flores, Carlos Alberto, Villena Chávez, Gretty Katherina, & Rodríguez Rodríguez, Eric F. (2020). Some phytochemical components and antioxidant activity in representatives of the Mentheae tribe (Lamiaceae) of Peru. Arnaldoa, 27(1), 169-180. https://dx.doi.org/10.22497/arnaldoa.271.27109
Shao, J., Fang, Y., Zhao, R., Chen, F., Yang, M., Jiang, J., Chen, Z., Yuan, X., & Jia, L. (2020). Evolution from small molecule to nano-drug delivery systems: An emerging approach for cancer therapy of ursolic acid. Asian Journal of Pharmaceutical Sciences, 15(6), 685-700. https://doi.org/10.1016/j.ajps.2020.03.001
Silva, M. G., Vieira, I., Mendes, F., Albuquerque, I., Dos Santos, R., Silva, F., & Morais, S. (2008). Variation of Ursolic Acid Content in Eight Ocimum Species from Northeastern Brazil. Molecules, 13(10), 2482-2487. https://doi.org/10.3390/molecules13102482
Soares, D. B. S., Duarte, L. P., Cavalcanti, A. D., Silva, F. C., Braga, A. D., Lopes, M. T. P., Takahashi, J. A., & Vieira-Filho, S. A. (2017). Psychotria viridis: Chemical constituents from leaves and biological properties. Anais Da Academia Brasileira de Ciências, 89(2), 927-938. https://doi.org/10.1590/0001-3765201720160411
Srisawat, P., Fukushima, E. O., Yasumoto, S., Robertlee, J., Suzuki, H., Seki, H., & Muranaka, T. (2019). Identification of oxidosqualene cyclases from the medicinal legume tree Bauhinia forficata: A step toward discovering preponderant α‐amyrin‐producing activity. New Phytologist, 224(1), 352-366. https://doi.org/10.1111/nph.16013
Suzuki, H., Fukushima, E. O., Shimizu, Y., Seki, H., Fujisawa, Y., Ishimoto, M., Osakabe, K., Osakabe, Y., & Muranaka, T. (2019). Lotus japonicus Triterpenoid Profile and Characterization of the CYP716A51 and LjCYP93E1 Genes Involved in Their Biosynthesis In Planta. Plant and Cell Physiology, 60(11), 2496-2509. https://doi.org/10.1093/pcp/pcz145
Szakiel, A., Pączkowski, C., Pensec, F., & Bertsch, C. (2012). Fruit cuticular waxes as a source of biologically active triterpenoids. Phytochemistry Reviews, 11(2-3), 263-284. https://doi.org/10.1007/s11101-012-9241-9
Thimmappa, R., Geisler, K., Louveau, T., O’Maille, P., & Osbourn, A. (2014). Triterpene Biosynthesis in Plants. Annual Review of Plant Biology, 65(1), 225-257. https://doi.org/10.1146/annurev-arplant-050312-120229
Tyszczuk-Rotko, K., Domańska, K., Sadok, I., Wójciak-Kosior, M., & Sowa, I. (2015). Voltammetric procedure for the determination of oleanolic and ursolic acids in plant extracts. Analytical Methods, 7(22), 9435-9441. https://doi.org/10.1039/C5AY01976A
Uddin, G., Siddiqui, B. S., Alam, M., Sadat, A., Ahmad, A., & Uddin, A. (2011). Chemical Constituents and Phytotoxicity of Solvent Extracted Fractions of Stem Bark of Grewia optiva Drummond ex Burret, 8(1), 85-91.
Vetal, M. D., Shirpurkar, N. D., & Rathod, V. K. (2014). Three phase partitioning coupled with ultrasound for the extraction of ursolic acid and oleanolic acid from Ocimum sanctum. Food and Bioproducts Processing, 92(4), 402-408. https://doi.org/10.1016/j.fbp.2013.09.002
Vo, N. N. Q., Nomura, Y., Muranaka, T., & Fukushima, E. O. (2019). Structure–Activity Relationships of Pentacyclic Triterpenoids as Inhibitors of Cyclooxygenase and Lipoxygenase Enzymes. Journal of Natural Products, 82(12), 3311-3320. https://doi.org/10.1021/acs.jnatprod.9b00538
Wei, Z. Y., Chi, K. Q., Wang, K.. S., Wu, J., Liu, L. P., & Piao, H. R. (2018). Design, synthesis, evaluation, and molecular docking of ursolic acid derivatives containing a nitrogen heterocycle as anti-inflammatory agents. Bioorganic & Medicinal Chemistry Letters, 28(10), 1797-1803. https://doi.org/10.1016/j.bmcl.2018.04.021
Winiewski, V., Serain, A., Sá, E., Salvador, M., & Stefanello, M. É. (2020). Chemical constituents of Sinningia mauroana and screening of its extracts for antimicrobial, antioxidant and cytotoxic activities. Química Nova. https://doi.org/10.21577/0100-4042.20170478
Xu, R., Fazio, G. C., & Matsuda, S. P. T. (2004). On the origins of triterpenoid skeletal diversity. Phytochemistry, 65(3), 261-291. https://doi.org/10.1016/j.phytochem.2003.11.014
Yang, P., Li, Y., Liu, X., & Jiang, S. (2007). Determination of free isomeric oleanolic acid and ursolic acid in Pterocephalus hookeri by capillary zone electrophoresis. Journal of Pharmaceutical and Biomedical Analysis, 43(4), 1331-1334. https://doi.org/10.1016/j.jpba.2006.10.042
Yao, L., Lu, J., Wang, J., & Gao, W. Y. (2020). Advances in biosynthesis of triterpenoid saponins in medicinal plants. Chinese Journal of Natural Medicines, 18(6), 417-424. https://doi.org/10.1016/S1875-5364(20)30049-2
Zhou, M., Zhang, R. H., Wang, M., Xu, G. B., & Liao, S. G. (2017). Prodrugs of triterpenoids and their derivatives. European Journal of Medicinal Chemistry, 131, 222-236. https://doi.org/10.1016/j.ejmech.2017.03.005
Zhou, Z., Tong, H. H. Y., Li, L., Shek, F. L. Y., Lv, Y., & Zheng, Y. (2015). Synthesis, characterization and thermal analysis of ursolic acid solid forms: Synthesis, characterization and thermal analysis of ursolic acid solid forms. Crystal Research and Technology, 50(7), 538-548. https://doi.org/10.1002/crat.201500034
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2021-04-30
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