Generic placeholder image

Mini-Reviews in Medicinal Chemistry

Editor-in-Chief

ISSN (Print): 1389-5575
ISSN (Online): 1875-5607

Review Article

Advances in Research on the Preparation and Biological Activity of Maslinic Acid

Author(s): Jianqiang Deng, Huiyun Wang, Xiaodong Mu, Xiuting He, Fenglan Zhao and Qingguo Meng*

Volume 21, Issue 1, 2021

Published on: 22 July, 2020

Page: [79 - 89] Pages: 11

DOI: 10.2174/1389557520666200722134208

Price: $65

Abstract

Maslinic acid, a pentacyclic triterpene acid, is mainly isolated from olives. Maslinic acid and its derivatives exhibit a broad range of biological properties, such as anti-inflammatory, anticancer, anti-diabetic, antimicrobial, neuroprotective and hepatoprotective activities. In this minireview, the progress of research on maslinic acid with regard to its bioactivities, extraction, semisynthetic preparation and patents is reported. The relationships between the structure and the activity of maslinic acid and its derivatives are also discussed.

Keywords: Maslinic acid, pentacyclic triterpene, extraction, semisynthetic, biological activity, structure-activity relationships.

Graphical Abstract

[1]
Romero, C.; García, A.; Medina, E.; Ruíz-Méndez, M.V.; de Castro, A.; Brenes, M. Triterpenic acids in table olives. Food Chem., 2010, 118(3), 670-674.
[http://dx.doi.org/10.1016/j.foodchem.2009.05.037]
[2]
Liu, J.; Xu, Y.; Yang, J.; Wang, W.; Zhang, J.; Zhang, R.; Meng, Q. Discovery, semisynthesis, biological activities, and metabolism of ocotillol-type saponins. J. Ginseng Res., 2017, 41(3), 373-378.
[http://dx.doi.org/10.1016/j.jgr.2017.01.001] [PMID: 28701880]
[3]
Bi, Yi. Ma, Cong.; Zhou, Zhiwen.; Zhang, Tingting.; Zhang, Hengyuan.; Zhang, Xiaochen; Lu, Jing; Meng, Qingguo; Lewis, Peter J.; Xu, Jinyi. Synthesis and antibacterial evaluation of novel hydrophilic ocotillol-type triterpenoid derivatives from 20(S)-protopanaxadiol. Rec. Nat. Prod., 2015, 9(3), 356-368.
[4]
Wen, X.; Sun, H.; Liu, J.; Wu, G.; Zhang, L.; Wu, X.; Ni, P. Pentacyclic triterpenes. Part 1: The first examples of naturally occurring pentacyclic triterpenes as a new class of inhibitors of glycogen phosphorylases. Bioorg. Med. Chem. Lett., 2005, 15(22), 4944-4948.
[http://dx.doi.org/10.1016/j.bmcl.2005.08.026] [PMID: 16169219]
[5]
Lin, C.; Yan, S.; Yin, M. Inhibitory effects of maslinic acid upon human esophagus, stomach and pancreatic cancer cells. J. Fun. F., 2014, 11, 581-588.
[http://dx.doi.org/10.1016/j.jff.2014.08.020]
[6]
López-Hortas, L.; Pérez-Larrán, P.; González-Muñoz, M.J.; Falqué, E.; Domínguez, H. Recent developments on the extraction and application of ursolic acid. A review. Food Res. Int., 2018, 103, 130-149.
[http://dx.doi.org/10.1016/j.foodres.2017.10.028 ] [PMID: 29389599]
[7]
Lozano-Mena, G.; Sánchez-González, M.; Juan, M.E.; Planas, J.M. Maslinic acid, a natural phytoalexin-type triterpene from olives--a promising nutraceutical? Molecules, 2014, 19(8), 11538-11559.
[http://dx.doi.org/10.3390/molecules190811538] [PMID: 25093990]
[8]
Nieto, F.R.; Cobos, E.J.; Entrena, J.M.; Parra, A.; García-Granados, A.; Baeyens, J.M. Antiallodynic and analgesic effects of maslinic acid, a pentacyclic triterpenoid from Olea europaea. J. Nat. Prod., 2013, 76(4), 737-740.
[http://dx.doi.org/10.1021/np300783a] [PMID: 23540838]
[9]
Kombargi, W.S.; Michelakis, S.E.; Petrakis, C.A. Effect of olive surface waxes on oviposition by Bactrocera oleae (diptera: Tephritidae). J. Eco. Ent., 1998, 91(4), 993-998.
[http://dx.doi.org/10.1093/jee/91.4.993]
[10]
Ou, B.; Tao, W.; Yang, S.; Feng, J.; Wang, J.; Yang, T. The antiapoptosis effect of Geum japonicum Thunb. var. chinense extracts on cerebral ischemia reperfusion injury via PI3K/Akt pathway. EBC. Alt. Med., 2018, 1-13.
[11]
Seo, Y. H.; Kang, S.-Y.; Shin, J.-S.; Ryu, S. M.; Lee, A. Y.; Choi, G. G. Chemical constituents from the aerial parts of Agastache rugosa and their inhibitory activities on prostaglandin E2 production in lipopolysaccharide-treated RAW 264.7 Macrophages J. Nat. Pro., 2019.
[12]
Kuraoka-Oliveira, Â.M.; Radai, J.A.S.; Leitão, M.M.; Lima Cardoso, C.A.; Silva-Filho, S.E.; Leite Kassuya, C.A. Anti-inflammatory and anti-arthritic activity in extract from the leaves of Eriobotrya japónica. J. Ethnopharmacol., 2019.112418
[13]
Mooi, L.Y.; Wahab, N.A.; Lajis, N.H.; Ali, A.M. Chemopreventive properties of phytosterols and maslinic acid extracted from Coleus tuberosus in inhibiting the expression of EBV early-antigen in Raji cells. Chem. Biodivers., 2010, 7(5), 1267-1275.
[http://dx.doi.org/10.1002/cbdv.200900193] [PMID: 20491082]
[14]
Hossain, M.A.; Ismail, Z. Isolation and characterization of triterpenes from the leaves of Orthosiphon stamineus. Arab. J. Chem., 2013, 6(3), 295-298.
[http://dx.doi.org/10.1016/j.arabjc.2010.10.009]
[15]
Yang, Z-G.; Li, H-R.; Wang, L-Y.; Li, Y-H.; Lu, S-G.; Wen, X-F.; Wang, J.; Daikonya, A.; Kitanaka, S. Triterpenoids from Hippophae rhamnoides L. and their nitric oxide production-inhibitory and DPPH radical-scavenging activities. Chem. Pharm. Bull. (Tokyo), 2007, 55(1), 15-18.
[http://dx.doi.org/10.1248/cpb.55.15] [PMID: 17202693]
[16]
Lee, S.H.; Liu, Q.; Kim, S.B.; Ahn, J.H.; Ahn, M-J.; Hwang, B.Y.; Lee, M. Kyeong. Maslinic acid, a triterpenoid from the root barks of Ulmus davidiana var. japonica, affects the viability of HSC-T6 hepatic stellate cells. Nat. Prod. Sci., 2011, 17(3), 216-220.
[17]
Mahesar, S.A.; Lucarini, M.; Durazzo, A.; Santini, A.; Lampe, A.I.; Kiefer, J. Application of infrared spectroscopy for functional compounds evaluation in olive oil: A current snapshot. J. Spectrosc., 2019, 1-11.
[18]
Kalogeropoulos, N.; Chiou, A.; Ioannou, M.; Karathanos, V.T.; Hassapidou, M.; Andrikopoulos, N.K. Nutritional evaluation and bioactive microconstituents (phytosterols, tocopherols, polyphenols, triterpenic acids) in cooked dry legumes usually consumed in the Mediterranean countries. Food Chem., 2010, 121(3), 682-690.
[http://dx.doi.org/10.1016/j.foodchem.2010.01.005]
[19]
Pérez-Camino, M.C.; Cert, A. Quantitative determination of hydroxy pentacyclic triterpene acids in vegetable oils. J. Agric. Food Chem., 1999, 47(4), 1558-1562.
[http://dx.doi.org/10.1021/jf980881h] [PMID: 10564016]
[20]
Wen, X.; Zhang, P.; Liu, J.; Zhang, L.; Wu, X.; Ni, P.; Sun, H. Pentacyclic triterpenes. Part 2: Synthesis and biological evaluation of maslinic acid derivatives as glycogen phosphorylase inhibitors. Bioorg. Med. Chem. Lett., 2006, 16(3), 722-726.
[http://dx.doi.org/10.1016/j.bmcl.2005.10.014] [PMID: 16246555]
[21]
Sommerwerk, S.; Csuk, R. Convenient and chromatography-free partial syntheses of maslinic acid and augustic acid. Tetrahedron Lett., 2014, 55(37), 5156-5158.
[22]
Yap, W. H.; Lim, Y. Mechanistic perspectives of maslinic acid in targeting inflammation. Bio. Res. Int., 2015, 1-9.
[http://dx.doi.org/10.1155/2015/279356]
[23]
Masullo, M.; Montoro, P.; Autore, G.; Marzocco, S.; Pizza, C.; Piacente, S. Quali-quantitative determination of triterpenic acids of Ziziphus jujuba fruits and evaluation of their capability to interfere in macrophages activation inhibiting NO release and iNOS expression. Food Res. Int., 2015, 77, 109-117.
[http://dx.doi.org/10.1016/j.foodres.2015.09.009]
[24]
Qian, Y.; Guan, T.; Tang, X.; Huang, L.; Huang, M.; Li, Y.; Sun, H. Maslinic acid, a natural triterpenoid compound from Olea europaea, protects cortical neurons against oxygen-glucose deprivation-induced injury. Eur. J. Pharmacol., 2011, 670(1), 148-153.
[http://dx.doi.org/10.1016/j.ejphar.2011.07.037 ] [PMID: 21839077]
[25]
Osuna, P. Use of maslinic acid for the treatment of diseases and the symptoms thereof by means of cox-2 inhibition US Patent US 20110105611A1., 2011.
[26]
Fukumitsu, S.; Villareal, M.O.; Aida, K.; Hino, A.; Hori, N.; Isoda, H.; Naito, Y. Maslinic acid in olive fruit alleviates mild knee joint pain and improves quality of life by promoting weight loss in the elderly. J. Clin. Biochem. Nutr., 2016, 59(3), 220-225.
[http://dx.doi.org/10.3164/jcbn.16-40] [PMID: 27895390]
[27]
Siewert, B.; Pianowski, E.; Csuk, R. Esters and amides of maslinic acid trigger apoptosis in human tumor cells and alter their mode of action with respect to the substitution pattern at C-28. Eur. J. Med. Chem., 2013, 70, 259-272.
[http://dx.doi.org/10.1016/j.ejmech.2013.10.016] [PMID: 24161703]
[28]
Zheng, K.; Sun, Cheng-bin; Mao, Hai-li; Yang, Zai-bo Progress in the research of chemical structural modification of ursolic acid and structure-activity relationship. J. China Pharm. Univ; , 2009, p. 06.
[29]
Siewert, B.; Pianowski, E.; Obernauer, A.; Csuk, R. Towards cytotoxic and selective derivatives of maslinic acid. Bioorg. Med. Chem., 2014, 22(1), 594-615.
[http://dx.doi.org/10.1016/j.bmc.2013.10.047] [PMID: 24268794]
[30]
Bai, X.; Zhang, Y.; Jiang, H.; Yang, P.; Li, H.; Zhang, Y.; He, P. Effects of maslinic acid on the proliferation and apoptosis of A549 lung cancer cells. Mol. Med. Rep., 2016, 13(1), 117-122.
[http://dx.doi.org/10.3892/mmr.2015.4552] [PMID: 26572558]
[31]
Peragón, J.; Rufino-Palomares, E.E.; Muñoz-Espada, I.; Reyes-Zurita, F.J.; Lupiáñez, J.A. A new HPLC-MS method for measuring maslinic acid and oleanolic acid in HT29 and HepG2 human cancer cells. Int. J. Mol. Sci., 2015, 16(9), 21681-21694.
[http://dx.doi.org/10.3390/ijms160921681] [PMID: 26370984]
[32]
Thakor, P.; Song, W.; Subramanian, R.B.; Thakkar, V.R.; Vesey, D.A.; Gobe, G.C. Maslinic acid inhibits proliferation of renal cell carcinoma cell lines and suppresses angiogenesis of endothelial cells. J. Kidney Cancer VHL, 2017, 4(1), 16-24.
[http://dx.doi.org/10.15586/jkcvhl.2017.64] [PMID: 28405545]
[33]
Alam, S.; Khan, F. 3D-QSAR studies on Maslinic acid analogs for anticancer activity against breast cancer cell line MCF-7. Sci. Rep., 2017, 7(1), 6019.
[http://dx.doi.org/10.1038/s41598-017-06131-0] [PMID: 28729623]
[34]
Yu, Y.; Wang, J.; Xia, N.; Li, B.; Jiang, X. Maslinic acid potentiates the antitumor activities of gemcitabine in vitro and in vivo by inhibiting NF-κB-mediated survival signaling pathways in human gallbladder cancer cells. Oncol. Rep., 2015, 33(4), 1683-1690.
[http://dx.doi.org/10.3892/or.2015.3755] [PMID: 25633045]
[35]
Mokhtari, K.; Rufino-Palomares, E.E.; Pérez-Jiménez, A.; Reyes-Zurita, F.J.; Figuera, C.; García-Salguero, L.; Lupiáñez, J.A. Maslinic acid, a triterpene from olive, affects the antioxidant and mitochondrial status of B16F10 melanoma cells grown under stressful conditions. Evid. Based Complement. Alternat. Med., 2015, 1-11.
[36]
Tian, Y.; Xu, H.; Farooq, A.A.; Nie, B.; Chen, X.; Su, S.; Yuan, R.; Qiao, G.; Li, C.; Li, X.; Liu, X.; Lin, X. Maslinic acid induces autophagy by down-regulating HSPA8 in pancreatic cancer cells. Phytother. Res., 2018, 32(7), 1320-1331.
[http://dx.doi.org/10.1002/ptr.6064] [PMID: 29516568]
[37]
Qian, Y.; Tang, X.; Guan, T.; Li, Y.; Sun, H. Neuroprotection by combined administration with maslinic acid, a natural product from olea europaea, and MK-801 in the cerebral ischemia model. Molecules, 2016, 21(8), 1093.
[http://dx.doi.org/10.3390/molecules21081093] [PMID: 27548129]
[38]
Gan, L.; Wang, Z.H.; Zhang, H.; Zhou, X.; Zhou, H.; Sun, C.; Si, J.; Zhou, R.; Ma, C.J.; Li, J. Endothelium-independent vasorelaxant effect of 20(S)-protopanaxadiol on isolated rat thoracic aorta. Acta Pharmacol. Sin., 2016, 37(12), 1555-1562.
[http://dx.doi.org/10.1038/aps.2016.74] [PMID: 27616575]
[39]
Qian, Y.; Huang, M.; Guan, T.; Chen, L.; Cao, L.; Han, X-J.; Huang, L.; Tang, X.; Li, Y.; Sun, H. Maslinic acid promotes synaptogenesis and axon growth via Akt/GSK-3β activation in cerebral ischemia model. Eur. J. Pharmacol., 2015, 764, 298-305.
[http://dx.doi.org/10.1016/j.ejphar.2015.07.028] [PMID: 26172083]
[40]
Yang, Y.W.; Tsai, C.W.; Mong, M.C.; Yin, M.C. Maslinic acid protected PC12 cells differentiated by nerve growth factor against β-amyloid-induced apoptosis. J. Agric. Food Chem., 2015, 63(47), 10243-10249.
[http://dx.doi.org/10.1021/acs.jafc.5b04156] [PMID: 26477978]
[41]
Schwarz, S.; Loesche, A.; Lucas, S.D.; Sommerwerk, S.; Serbian, I.; Siewert, B.; Pianowski, E.; Csuk, R. Converting maslinic acid into an effective inhibitor of acylcholinesterases. Eur. J. Med. Chem., 2015, 103, 438-445.
[http://dx.doi.org/10.1016/j.ejmech.2015.09.007] [PMID: 26383128]
[42]
Yan, S.L.; Yang, H.T.; Lee, H.L.; Yin, M.C. Protective effects of maslinic acid against alcohol-induced acute liver injury in mice. Food Chem. Toxicol., 2014, 74, 149-155.
[http://dx.doi.org/10.1016/j.fct.2014.09.018] [PMID: 25301236]
[43]
Wang, Y.Y.; Diao, B.Z.; Zhong, L.H.; Lu, B.L.; Cheng, Y.; Yu, L.; Zhu, L.Y. Maslinic acid protects against lipopolysaccharide/d-galactosamine-induced acute liver injury in mice. Microb. Pathog., 2018, 119, 49-53.
[http://dx.doi.org/10.1016/j.micpath.2018.04.002] [PMID: 29627448]
[44]
Rajopadhye, A.; Upadhye, A.S. Estimation of bioactive compound, maslinic acid by HPTLC, and evaluation of hepatoprotective activity on fruit pulp of Ziziphus jujube mill. cultivars in india. Evid. Based Complement. Alternat. Med., 2016, 1-8.
[45]
Dayrit, F.M. From Artemisia annua L. to artemisinins: The discovery and development of artemisinins and antimalarial Agents Chem. Med. Chem., 2017, 13(1), 124-125.
[46]
Moneriz, C.; Mestres, J.; Bautista, J.M.; Diez, A.; Puyet, A. Multi-targeted activity of maslinic acid as an antimalarial natural compound. FEBS J., 2011, 278(16), 2951-2961.
[http://dx.doi.org/10.1111/j.1742-4658.2011.08220.x ] [PMID: 21689375]
[47]
Martín-Navarro, C. M.; López-Arencibia, A.; Sifaoui, I.; ReyesBatlle, M.; Fouque, E.; Osuna, A.; Lorenzo-Morales, J. Amoebicidal activity of caffeine and maslinic acid by the induction of programmed cell death in acanthamoeba. Anti. Agen. Chem., 2017, 61(6)
[48]
Pavel, I.Z.; Danciu, C.; Oprean, C.; Dehelean, C.A.; Muntean, D.; Csuk, R.; Muntean, D.M. In Vitro evaluation of the antimicrobial ability and cytotoxicity on two melanoma cell lines of a benzylamide derivative of maslinic acid. Anal. Cell. Pathol. (Amst.), 2016, 20162787623
[http://dx.doi.org/10.1155/2016/2787623] [PMID: 28050335]
[49]
Han, B.; Meng, Q.; Li, Q.; Zhang, J.; Bi, Y.; Jiang, N. Effect of 20(S)-protopanaxatriol and its epimeric derivatives on myocardial injury induced by isoproterenol. Arzneimittelforschung, 2011, 61(3), 148-152.
[http://dx.doi.org/10.1055/s-0031-1296181] [PMID: 21528638]
[50]
Shi, Y.; Han, B.; Yu, X.; Qu, S.; Sui, D. Ginsenoside Rb3 ameliorates myocardial ischemia-reperfusion injury in rats. Pharm. Biol., 2011, 49(9), 900-906.
[http://dx.doi.org/10.3109/13880209.2011.554845] [PMID: 21591990]
[51]
Bi, Y.; Wang, T.; Meng, Q.; Zhang, J.; Wang, L.; Li, Q.; Zhao, F.; Sun, H. Synthesis and myocardial ischemia protective effect of ocotillol-type derivatives. Red. Nat. Pro., 2012, 6(3), 242-254.
[52]
Liu, Y.-L.; Kong, C.-Y.; Song, P.; Zhou, H.; Zhao, X.-S.; Tang, Q.-Z. Maslinic acid protects against pressure overload-induced cardiac hypertrophy in mice. J. Phar. Sci., 2018.
[http://dx.doi.org/10.1016/j. jphs.2018.08.014]
[53]
Parra, A.; Rivas, F.; Lopez, P.E.; Garcia-Granados, A.; Martinez, A.; Albericio, F.; Marquez, N.; Muñoz, E. Solution- and solid-phase synthesis and anti-HIV activity of maslinic acid derivatives containing amino acids and peptides. Bioorg. Med. Chem., 2009, 17(3), 1139-1145.
[http://dx.doi.org/10.1016/j.bmc.2008.12.041] [PMID: 19135380]
[54]
Wang, Z.H.; Mong, M.C.; Yang, Y.C.; Yin, M.C. Asiatic acid and maslinic acid attenuated kainic acid-induced seizure through decreasing hippocampal inflammatory and oxidative stress. Epilepsy Res., 2018, 139, 28-34.
[http://dx.doi.org/10.1016/j.eplepsyres.2017.11.003 PMID: 29156327]
[55]
Sánchez-González, M.; Lozano-Mena, G.; Parra, A.; Juan, M.E.; Planas, J.M. Identification in rat plasma and urine by linear trap quadrupole-orbitrap mass spectrometry of the metabolites of maslinic acid, a triterpene from olives. J. Agric. Food Chem., 2015, 63(4), 1126-1132.
[http://dx.doi.org/10.1021/jf505379g] [PMID: 25575098]
[56]
Sánchez-Quesada, C.; López-Biedma, A.; Gaforio, J.J. Maslinic Acid enhances signals for the recruitment of macrophages and their differentiation to M1 state. Evid. Based Complement. Alternat. Med., 2015, 1-9.
[http://dx.doi.org/10.1155/2015/654721]
[57]
Yap, W.H.; Ooi, B.K.; Ahmed, N.; Lim, Y.M. Maslinic acid modulates secreted phospholipase A2-IIA (sPLA2-IIA)-mediated inflammatory effects in macrophage foam cells formation. J. Biosci., 2018, 43(2), 277-285.
[http://dx.doi.org/10.1007/s12038-018-9745-6] [PMID: 29872016]
[58]
Fukumitsu, S.; Villareal, M.O.; Fujitsuka, T.; Aida, K.; Isoda, H. Anti-inflammatory and anti-arthritic effects of pentacyclic triterpenoids maslinic acid through NF-κB inactivation. Mol. Nutr. Food Res., 2016, 60(2), 399-409.
[http://dx.doi.org/10.1002/mnfr.201500465] [PMID: 26499467]
[59]
Baba, K.; Hiramatsu, R.; Suradej, B.; Tanigaki, R.; Koeda, S.; Waku, T.; Kataoka, T. Asiatic acid, corosolic acid, and maslinic acid interfere with intracellular trafficking and N-Linked glycosylation of intercellular adhesion molecule-1. Biol. Pharm. Bull., 2018, 41(12), 1757-1768.
[http://dx.doi.org/10.1248/bpb.b18-00276] [PMID: 30504678]
[60]
Reyes-Zurita, F.J.; Rufino-Palomares, E.E.; García-Salguero, L.; Peragón, J.; Medina, P.P.; Parra, A.; Cascante, M.; Lupiáñez, J.A. Maslinic Acid, a natural triterpene, induces a death receptor-mediated apoptotic mechanism in Caco-2 P53-deficient colon adenocarcinoma cells. PLoS One, 2016, 11(1)e0146178
[http://dx.doi.org/10.1371/journal.pone.0146178] [PMID: 26751572]
[61]
Jeon, S.J.; Kim, E.; Lee, J.S.; Oh, H.K.; Zhang, J.; Kwon, Y.; Jang, D.S.; Ryu, J.H. Maslinic acid ameliorates NMDA receptor blockade-induced schizophrenia-like behaviors in mice. Neuropharmacology, 2017, 126, 168-178.
[http://dx.doi.org/10.1016/j.neuropharm.2017.09.014 ] [PMID: 28899728]
[62]
Abu-Reidah, I.M.; Ali-Shtayeh, M.S.; Jamous, R.M.; Arráez-Román, D.; Segura-Carretero, A. Comprehensive metabolite profiling of Arum palaestinum (Araceae) leaves by using liquid chromatography–tandem mass spectrometry. Food Res. Int., 2015, 70, 74-86.
[http://dx.doi.org/10.1016/j.foodres.2015.01.023]
[63]
Wang, X.; Zhang, C.; Peng, Y.; Zhang, H.; Wang, Z.; Gao, Y.; Liu, Y.; Zhang, H. Chemical constituents, antioxidant and gastrointestinal transit accelerating activities of dried fruit of Crataegus dahurica. Food Chem., 2018, 246, 41-47.
[http://dx.doi.org/10.1016/j.foodchem.2017.11.011 ] [PMID: 29291866]
[64]
Osunsanmi, F.O.; Oyinloye, B.E.; Mosa, R.A.; Ikhile, M.I.; Ngila, J.C.; Shode, F.O.; Opoku, A.R. Anti-platelet aggregation of mixtures of betulinic oleanolic and maslinic acids and derivatives from medicinal plants. Trop. J. Pharm. Res., 2016, 15(8), 1613.
[http://dx.doi.org/10.4314/tjpr.v15i8.3]
[65]
Yap, W.H.; Ahmed, N.; Lim, Y.M. Inhibition of human group IIA-secreted phospholipase A2 and THP-1 monocyte recruitment by maslinic acid. Lipids, 2016, 51(10), 1153-1159.
[http://dx.doi.org/10.1007/s11745-016-4186-1 ] [PMID: 27540737]
[66]
Xu, J.; Liu, T.; Li, Y.; Yuan, C.; Ma, H.; Seeram, N.P.; Liu, F.; Mu, Y.; Huang, X.; Li, L. Hypoglycemic and hypolipidemic effects of triterpenoid-enriched Jamun (Eugenia jambolana Lam.) fruit extract in streptozotocin-induced type 1 diabetic mice. Food Funct., 2018, 9(6), 3330-3337.
[http://dx.doi.org/10.1039/C8FO00095F] [PMID: 29808185]
[67]
Chouaïb, K.; Hichri, F.; Nguir, A.; Daami-Remadi, M.; Elie, N.; Touboul, D.; Ben Jannet, H.; Hamza, M.A. Semi-synthesis of new antimicrobial esters from the natural oleanolic and maslinic acids. Food Chem., 2015, 183, 8-17.
[http://dx.doi.org/10.1016/j.foodchem.2015.03.018 ] [PMID: 25863603]
[68]
Lin, X.; Liu, H.; Liao, D. Anti-liver cancer effect of maslinic acid and its formulation China Patent CN 102091078 A., 2011.
[69]
Lin, X.; Liu, H.; Liao, D. Anti-ovarian cancer effect of maslinic acid and the preparation thereof China Patent CN 102225068 A., 2011.
[70]
Lin, X.; Liu, H.; Wei, J.; Liu, M.; Song, Y.; Wu, N. Antitumor effect of maslinic acid against pancreas carcinoma, and its medicinal preparation China Patent CN 102151276 A., 2011.
[71]
Liu, M.; Luo, J.; Li, C.; Yang, Z.; Qiu, W.; Tang, J. Anti-tumor MA-TNFα medical composition containing maslinic acid, its formulation and application China Patent CN 102008715 A., 2011.
[72]
Luo, J.; Liu, M.; Li, C.; Yang, Z.; Qiu, W.; Tang, J. Application of maslinic acid and its derivative in preparing the medicine for inhibiting osteoclast differentiation and function for treating and/or preventing osteoclast activity-related diseases China Patent CN 102210691 A., 2011.
[73]
Xiang, Cheng; Zhuang, Wenting; Li, Peng; Li, Baocai; Zhang, Lindong; Zhu, Luping; He, Jing; Dai, Weifeng Application of maslinic acid in treating tumor neovascularization China Patent CN 102670621A, 2012.
[74]
Lin, X.; Liu, H.; Liao, D. Effect of maslinic acid on treating breast cancer and its medicinal composition China Patent CN 102106859 A, 2011.
[75]
Lin, X.; Liao, D.; Liu, H. Effect of maslinic acid on treating colon cancer and its medicinal composition China Patent CN 102106861 A, 2011.
[76]
Ling, C.; Xin, H.; Xu, Y.; Wu, Y.; Sheng, J.; Zhu, L.; Zheng, G. Extraction and purification of Actinidia valvata leaf extract containing corosolic acid, maslinic acid and ursolic acid with antitumor effect China Patent CN 101584718 A., 2009.
[77]
Tang, J.; Li, J.; Wang, B.; Qiu, W.; Shen, Q.; Yang, F.; Zhang, W.; Zou, H. Maslinic acid derivatives, preparation method and medical application China Patent CN 101619088 A, 2010.
[78]
Lin, Xiukun; Liu, Haizhou Liao, Dezhong Medical preparation and application of maslinic acid with cervical cancer-resisting effect China Patent CN 102106858A, 2011.
[79]
Xie, D.; Huang, J.; Lu, M.; Ye, C. Method for extracting and separating maslinic acid from Olea europaea leaf China Patent CN 106349324 A, 2017.
[80]
Huang, J.; Xie, D.; Lu, M.; Ye, C. Method for extracting maslinic acid from Olive pomace China Patent CN 106397529 A, 2017.
[81]
Di, D.; Huang, X.; Wang, Z. Method for extracting mixture containing maslinic acid and oleanolic acid from fruit residue of Olea europaea China Patent CN 103169771 A, 2013.
[82]
Sun, H.; Wen, X.; Ni, P. Method for preparation of Corosolic acid and Maslinic acid China Patent CN 1634971 A., 2005.
[83]
Tan, Jian wen; Wang, Jing; Xu, Qiaolin Method for preparation of maslinic acid and its application for preparing antibacterial agent China Patent CN 103435678A, 2013.
[84]
Chen, L.; Lu, Y.; Xu, S.; Xin, Y. Method for preparing high-purity maslinic acid with olive as material China Patent CN 101418031 A, 2009.
[85]
Hong, Y.; Zeng, Z.; Yin, X.; Jiang, Y.; Yang, W.; Wu, G.; Liao, X.; Wang, C.; Liu, X. Preparation of water soluble maslinic acid derivative for treating diabetes China Patent CN 109232708 A, 2019.
[86]
Wang, X.; Shi, C.; Huang, Y.; Chen, J.; Jiang, X.; Ding, P.; Ding, H.; Gong, Z. Method for synthesis of maslinic acid China Patent CN 101974064 A, 2011.
[87]
Huang, Z. Novel Maslinic acid derivative or its stereoisomer for treating hepatic diseases China Patent CN 101190938 A 20080604, 2008.

Rights & Permissions Print Cite
© 2024 Bentham Science Publishers | Privacy Policy