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http://dx.doi.org/10.22889/KJP.2020.51.4.238

Anti-Amyloidogenic Effects of Triterpenoids Isolated from Perilla Leaves  

Yeo, Ji-Yun (College of Pharmacy, Dankook University)
Lee, Chung-Hyun (College of Pharmacy, Dankook University)
Park, So-Young (College of Pharmacy, Dankook University)
Publication Information
Korean Journal of Pharmacognosy / v.51, no.4, 2020 , pp. 238-243 More about this Journal
Abstract
Perilla frutescens Britton var. acuta Kudo, an annual plant primarily cultivated in China, Japan, and Korea, has been used as a traditional medicine to treat inflammatory diseases, depression, and many anxiety-related disorders. Previously, we reported the inhibitory effects of n-hexane layer of P. frutescens var. acuta extract against beta-amyloid (Aβ) aggregation, and the isolation of asarone derivatives as active constituents from n-hexane layer. In this study, dichloromethane layer of P. frutescens var. acuta was applied to bioassay-guided isolation methods accompanied with Thioflavin T (Th T) fluorescence assay to investigate the inhibitory effect on Aβ aggregation and disaggregation. As the results, three triterpenoids including ursolic acid (1), tormentic acid (2) and corosolic acid (3) were isolated. All compounds reduced Aβ aggregation and increased disaggregation of preformed Aβ aggregates in a dose-dependent manner. However, the inhibitory effect of three compounds on Aβ aggregation was not correlated with antioxidant activity, which was measured by DPPH assay. Taken together, these results suggest that the triterpenoid derivatives from P. frutescens have the potential to be developed as good therapeutics or preventatives for AD.
Keywords
Perilla frutescens var. acuta; Beta-amyloid; Aggregation; Disaggregation; Triterpenoids;
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1 Hardy, J. A. and Higgins, G. A. (1992) Alzheimer's disease: the amyloid cascade hypothesis. Science 256: 184-185.   DOI
2 Lambert, M. P., Barlow, A. K., Chromy, B. A., Edwards, C., Freed, R., Iosatos, M., Morgan, T. E., Rozovsky, I., Trommer, B., Viola, K. L., Wals, P., Zhang, C., Finch, C. E., Krafft, G. A. and Klein, W. L. (1998) Diffusible, nonfribrillar ligands derived from Aβ1-42 are potent central nervous system neurotoxins. Proc. Natl. Acad. Sci. USA 95: 6448-6453.   DOI
3 Ward, R. V., Jennings, K. H., Jepras, R., Neville, W., Owen, D. E., Hawkins, J. and Howlett, D. R. (2000) Fractionation and characterization of oligomeric, protofibrillar and fibrillar forms of beta-amyloid peptide. Biochemical. J. 348: 137-144.   DOI
4 배기환 (2019) 천연약물도감 I·II, pp 141-142 (II). 교학사, 서울.
5 Zheng, J., Dong, Z. and Se, J. (1997) Modern study of Traditional Chinese Medicines, pp. 4354-4363. Xue Yuan Press, China.
6 Peng, Y., Ye, J. and Kong, J. (2005) Determination of phenolic compounds in Perilla frutescens L. by capillary electrophoresis with electrochemical detection. J. Agric. Food Chem. 53: 8141-8147.   DOI
7 Seo, W. H. and Baek, H. H. (2009) Characteristic aromaactive compounds of Korean perilla (Perilla frutescens Britton) leaf. J. Agric. Food Chem. 57: 11537-11542.   DOI
8 Kil, H. W., Rho, T. and Yoo, K. D. (2020) Phytochemical study of hot-water extract of Perillae Folium. Kor. J. Pharmacogn. 51: 55-64.   DOI
9 Kim, D.-J., Kim, M.-S., Kim, S., Hwang, K.-W. and Park, S.-Y. (2017) Anti‐amyloidogenic effects of Perilla frutescens var. acuta on beta‐amyloid aggregation and disaggregation. J. Food Biochem. 41: e12393.   DOI
10 Lee, J.E., Kim, N., Yeo, J.Y., Seo, D.-G., Kim, S., Lee, J.-S., Hwang, K. W. and Park, S.-Y. (2019) Anti-Amyloidogenic effects of asarone derivatives from Perilla frutescens leaves against beta-amyloid agregation and nitric oxide production. Molecules 24: 4297.   DOI
11 Woo, K. W., Han, J. Y., Choi, S. U., Kim, K. H. and Lee, K. R. (2014) Triterpenes from Perilla frutescens var. acuta and their cytotoxic activity. Nat. Prod. Sci. 20: 71-75.
12 Seebacher, W., Simic, N., Weis, R., Saf, R. and Kunert, O. (2003) Spectral assignments and reference data. Magn. Reson. Chem. 41: 636-638.   DOI
13 Taniguchi, S., Imayoshi, Y., Kobayashi, E., Takamatsu, Y., Ito, H., Hatano, T., Sakagami, H., Tokuda, H., Nishino, H., Sugita, D., Shimura, S. and Yoshida, T. (2002) Production of bioactive triterpenes by Eriobotrya japonica Calli. Phytochemistry 59: 315-323.   DOI
14 Wen, X., Sun, H., Liu, J., Wu, G., Zhang, L., Wu, X. and Ni, P. (2005) 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. 15: 4944-4948.   DOI
15 Lee, J.-E., Kim, M.-S. and Park, S.-Y. (2017) Effect of natural antioxidants on the aggregation and disaggregation of betaamyloid. Trop. J. Pharmaceut. Res. 11: 2629-2635.
16 Ono, K., Hasegawa, K., Naiki, H. and Yamada, M. (2004) Curcumin has potent anti-amyloidogenic effects for Alzheimer's beta-amyloid fibrils in vitro. J. Neurosci. Res. 75: 742-750.   DOI
17 Mattson, M. P. (2004) Pathways towards and away from Alzheimer's disease. Nature 430: 631-639.   DOI
18 Butterfield, D. A., Drake, J., Pocernich, C. and Castegna, A. (2001) Evidence of oxidative damage in Alzheimer's disease brain: central role for amyloid beta-peptide. Trends Mol. Med. 7: 548-554.   DOI
19 Jimenez-Aliaga, K., Bermejo-Bescos, P., Benedi, J. and Martin-Aragon, S. (2011) Quercetin and rutin exhibit antiamyloidogenic and fibril-disaggregating effects in vitro and potent antioxidant activity in APPswe cells. Life Sci. 89: 939-945.   DOI
20 Sharoar, MG., Thapa, A., Shahnawaz, M., Ramasamy, VS., Woo, ER., Shin, SY. and Park, I-S. (2012) Kaempferol-3-O-rhamnoside abrogates amyloid beta toxicity by modulating monomers and remodeling oligomers and fibrils to non-toxic aggregates. J. Biomed. Sci. 19: 104.   DOI
21 Yamada, M., Ono, K., Hamaguchi, T. and Noguchi-Shinohara, M. (2015) Natural phenolic compounds as therapeutic and preventive agents for cerebral amyloidosis. Adv. Exp. Med. Biol. 863: 79-94.   DOI
22 Murakami, K., Yoshioka, T., Horii, S., Hanaki, M., Midorikawa, S., Taniwaki, S., Gunji, H., Akagi, K.-I., Kawase, T., Hirosed, K. and Irie, K. (2018) Role of the carboxy groups of triterpenoids in their inhibition of the nucleation of amyloid β42 required for forming toxic oligomers. Chem. Commmun. 54: 6272-6275.   DOI
23 Cui, W., Sun, C., Ma, Y., Wang, S., Wang, X. and Zhang, Y. (2020) Neuroprotective effect of tormentic acid against memory impairment and neuro-inflammation in an Alzheimer's disease mouse model. Mol. Med. Rep. 22: 739-750.   DOI
24 Murakami, K. and Irie, K. (2019) Three structural features of functional food components and herbal medicine with amyloid β42 anti-aggregation properties. Molecules 24: 2125.   DOI
25 Liang, W., Zhao, X., Feng, J., Song, F. and Pan, Y. (2016) Ursolic acid attenuates beta-amyloid-induced memory impairment in mice. Arq. Neuropsiquiatr. 74: 482-488.   DOI