SIRT1 Activation Enhancing 8,3′-Neolignans from the Twigs of Corylopsis coreana Uyeki
Abstract
:1. Introduction
2. Results and Discussion
2.1. General
2.2. Structure Elucidation of the Previously Undescribed Compounds
2.3. Evaluation of SIRT1 Stimulatory Effects
3. Materials and Methods
3.1. General Experimental Procedures
3.2. Plant Material
3.3. Extraction and Isolation
3.3.1. Corynol (1)
3.3.2. 3′-Methoxycorynol (2)
3.3.3. 3′-Deoxycorynol (3)
3.4. MTT Cell Viability Assay
3.5. Cell Culture and Transfection
3.6. In Vitro SIRT1 Deacetylation in a Luciferase Reporter Assay
3.7. NAD+/NADH Ratio Measurement
3.8. SIRT1 Deacetylation in a SIRT1 Enzyme-Based Assay
3.9. Molecular Docking Simulation
4. Conclusions
Supplementary Materials
Author Contributions
Funding
Institutional Review Board Statement
Informed Consent Statement
Data Availability Statement
Acknowledgments
Conflicts of Interest
References
- Lee, Y.; Kim, J.E.; Kim, K.J.; Cho, S.S.; Son, Y.J. Optimized Extract from Corylopsis coreana Uyeki (Hamamelidaceae) Flos Inhibits Osteoclast Differentiation. Evid. Based Complement. Altern. Med. 2018, 2018, 6302748. [Google Scholar] [CrossRef] [PubMed] [Green Version]
- Bae, C.S.; Yun, C.H.; Ahn, T. Extracts from Erythronium japonicum and Corylopsis coreana Uyeki reduce 1,3-dichloro-2-propanol-mediated oxidative stress in human hepatic cells. Food Sci. Biotechnol. 2019, 28, 175–180. [Google Scholar] [CrossRef] [PubMed]
- Yoon, I.S.; Park, D.H.; Ki, S.H.; Cho, S.S. Effects of extracts from Corylopsis coreana Uyeki (Hamamelidaceae) flos on xanthine oxidase activity and hyperuricemia. J. Pharm. Pharmacol. 2016, 68, 1597–1603. [Google Scholar] [CrossRef]
- Seo, J.H.; Kim, J.E.; Shim, J.H.; Yoon, G.; Bang, M.A.; Bae, C.S.; Lee, K.J.; Park, D.H.; Cho, S.S. HPLC Analysis, Optimization of Extraction Conditions and Biological Evaluation of Corylopsis coreana Uyeki Flos. Molecules 2016, 21, 94. [Google Scholar] [CrossRef]
- Kim, M.H.; Ha, S.Y.; Oh, M.H.; Kim, H.H.; Kim, S.R.; Lee, M.W. Anti-Oxidative and Anti-Proliferative Activity on Human Prostate Cancer Cells Lines of the Phenolic Compounds from Corylopsis coreana Uyeki. Molecules 2013, 18, 4876–4886. [Google Scholar] [CrossRef]
- Satoh, A.; Stein, L.; Imai, S. The role of mammalian sirtuins in the regulation of metabolism, aging, and longevity. Handb. Exp. Pharmacol. 2011, 206, 125–162. [Google Scholar] [CrossRef] [Green Version]
- Hwang, J.W.; Yao, H.W.; Caito, S.; Sundar, I.K.; Rahman, I. Redox regulation of SIRT1 in inflammation and cellular senescence. Free Radic. Biol. Med. 2013, 61, 95–110. [Google Scholar] [CrossRef] [Green Version]
- Chang, H.C.; Guarente, L. SIRT1 and other sirtuins in metabolism. Trends Endocrinol. Metab. 2014, 25, 138–145. [Google Scholar] [CrossRef]
- Lee, S.H.; Lee, J.H.; Lee, H.Y.; Min, K.J. Sirtuin signaling in cellular senescence and aging. BMB Rep. 2019, 52, 24–34. [Google Scholar] [CrossRef] [Green Version]
- Chao, S.C.; Chen, Y.J.; Huang, K.H.; Kuo, K.L.; Yang, T.H.; Huang, K.Y.; Wang, C.C.; Tang, C.H.; Yang, R.S.; Liu, S.H. Induction of sirtuin-1 signaling by resveratrol induces human chondrosarcoma cell apoptosis and exhibits antitumor activity. Sci. Rep. 2017, 7, 3180. [Google Scholar] [CrossRef]
- Iside, C.; Scafuro, M.; Nebbioso, A.; Altucci, L. SIRT1 Activation by Natural Phytochemicals: An Overview. Front. Pharmacol. 2020, 11, 1225. [Google Scholar] [CrossRef]
- Won, T.H.; Song, I.H.; Kim, K.H.; Yang, W.Y.; Lee, S.K.; Oh, D.C.; Oh, W.K.; Oh, K.B.; Shin, J. Bioactive metabolites from the fruits of Psoralea corylifolia. J. Nat. Prod. 2015, 78, 666–673. [Google Scholar] [CrossRef] [PubMed]
- Kou, D.Q.; Jiang, Y.L.; Qin, J.H.; Huang, Y.H. Magnolol attenuates the inflammation and apoptosis through the activation of SIRT1 in experimental stroke rats. Pharmacol. Rep. 2017, 69, 642–647. [Google Scholar] [CrossRef]
- Teponno, R.B.; Kusari, S.; Spiteller, M. Recent advances in research on lignans and neolignans. Nat. Prod. Rep. 2016, 33, 1044–1092. [Google Scholar] [CrossRef] [Green Version]
- Niculaes, C.; Morreel, K.; Kim, H.; Lu, F.; McKee, L.S.; Ivens, B.; Haustraete, J.; Vanholme, B.; Rycke, R.D.; Hertzberg, M.; et al. Phenylcoumaran Benzylic Ether Reductase Prevents Accumulation of Compounds Formed under Oxidative Conditions in Poplar Xylem. Plant Cell 2014, 26, 3775. [Google Scholar] [CrossRef] [Green Version]
- Lv, Q.Q.; Yang, X.N.; Yan, D.M.; Liang, W.Q.; Liu, H.N.; Yang, X.W.; Li, F. Metabolic profiling of dehydrodiisoeugenol using xenobiotic metabolomics. J. Pharm. Biomed. Anal. 2017, 145, 725–733. [Google Scholar] [CrossRef]
- Iorizzi, M.; Lanzotti, V.; De Marino, S.; Zollo, F.; Blanco-Molia, M.; Macho, A.; Munoz, E. New glycosides from Capsicum annuum L. var. acuminatum. Isolation, structure determination, and biological activity. J. Agric. Food Chem. 2001, 49, 2022–2029. [Google Scholar] [CrossRef] [PubMed]
- Subramanian, R.; Subbramaniyan, P.; Raj, V. Isolation of bergenin from Peltophorum pterocarpum flowers and its bioactivity. Beni-Suef Univ. J. Basic Appl. Sci. 2015, 4, 256–261. [Google Scholar] [CrossRef] [Green Version]
- Li, Y.J.; Xu, C.T.; Lin, D.D.; Qin, J.K.; Ye, G.J.; Deng, Q.H. Anti-inflammatory polyphenol constituents derived from Cissus pteroclada Hayata. Bioorganic Med. Chem. Lett. 2016, 26, 3425–3428. [Google Scholar] [CrossRef]
- Wen, L.; Lin, Y.L.; Lv, R.M.; Yan, H.J.; Yu, J.Q.; Zhao, H.Q.; Wang, X.; Wang, D.J. An Efficient Method for the Preparative Isolation and Purification of Flavonoids from Leaves of Crataegus pinnatifida by HSCCC and Pre-HPLC. Molecules 2017, 22, 767. [Google Scholar] [CrossRef] [PubMed] [Green Version]
- Choi, S.J.; Hong, Y.D.; Lee, B.; Park, J.S.; Jeong, H.W.; Kim, W.G.; Shin, S.S.; Yoon, K.D. Separation of Polyphenols and Caffeine from the Acetone Extract of Fermented Tea Leaves (Camellia sinensis) Using High-Performance Countercurrent Chromatography. Molecules 2015, 20, 13216–13225. [Google Scholar] [CrossRef] [Green Version]
- Lin, L.C.; Wang, M.N.; Tseng, T.Y.; Sung, J.S.; Tsai, T.H. Pharmacokinetics of (-)-epigallocatechin-3-gallate in conscious and freely moving rats and its brain regional distribution. J. Agric. Food Chem. 2007, 55, 1517–1524. [Google Scholar] [CrossRef]
- Si, C.L.; Zhang, Y.; Zhu, Z.Y.; Liu, S.C. Chemical Constituents with Antioxidant Activity from the Pericarps of Juglans sigillata. Chem. Nat. Compd. 2011, 47, 442–445. [Google Scholar] [CrossRef]
- El-Nashar, H.A.S.; Eldahshan, O.A.; Elshawi, O.E.; Singab, A.N.B. Phytochemical Investigation, Antitumor Activity, and Hepatoprotective Effects of Acrocarpus fraxinifolius Leaf Extract. Drug Dev. Res. 2017, 78, 210–226. [Google Scholar] [CrossRef]
- Bai, N.S.; He, K.; Roller, M.; Zheng, B.L.; Chen, X.Z.; Shao, Z.G.; Peng, T.S.; Zheng, Q.Y. Active Compounds from Lagerstroemia speciosa, Insulin-like Glucose Uptake-Stimulatory/Inhibitory and Adipocyte Differentiation-Inhibitory Activities in 3T3-L1 Cells. J. Agric. Food Chem. 2008, 56, 11668–11674. [Google Scholar] [CrossRef]
- Barati, B.; Moghadam, M.; Rahmati, A.; Tangestaninejad, S.; Mirkhani, V.; Mohammadpoor-Baltork, I. Ruthenium Hydride Catalyzed Direct Oxidation of Alcohols to Carboxylic Acids via Transfer Hydrogenation: Styrene Oxide as Oxygen Source. Synlett 2013, 24, 90–96. [Google Scholar] [CrossRef]
- Numonov, S.; Edirs, S.; Bobakulov, K.; Qureshi, M.N.; Bozorov, K.; Sharopov, F.; Setzer, W.N.; Zhao, H.Q.; Habasi, M.; Sharofova, M.; et al. Evaluation of the Antidiabetic Activity and Chemical Composition of Geranium collinum Root Extracts-Computational and Experimental Investigations. Molecules 2017, 22, 983. [Google Scholar] [CrossRef]
- Farag, M.A.; Al-Mahdy, D.A.; El Dine, R.S.; Fahmy, S.; Yassin, A.; Porzel, A.; Brandt, W. Structure-Activity Relationships of Antimicrobial Gallic Acid Derivatives from Pomegranate and Acacia Fruit Extracts against Potato Bacterial Wilt Pathogen. Chem. Biodivers. 2015, 12, 955–962. [Google Scholar] [CrossRef]
- Lancefield, C.S.; Ojo, O.S.; Tran, F.; Westwood, N.J. Isolation of Functionalized Phenolic Monomers through Selective Oxidation and C-O Bond Cleavage of the beta-O-4 Linkages in Lignin. Angew. Chem. 2015, 54, 258–262. [Google Scholar] [CrossRef]
- Verotta, L.; Dell’Agli, M.; Giolito, A.; Guerrini, M.; Cabalion, P.; Bosisio, E. In vitro antiplasmodial activity of extracts of Tristaniopsis species and identification of the active constituents: Ellagic acid and 3,4,5-trimethoxyphenyl-(6′-O-galloyl)-O-beta-D-glucopyranoside. J. Nat. Prod. 2001, 64, 603–607. [Google Scholar] [CrossRef]
- Feng, W.-S.; Li, K.-K.; Zheng, X.-K. A new norlignan lignanoside from Selaginella moellendorffii Hieron. Acta Pharm. Sin. B 2011, 1, 36–39. [Google Scholar] [CrossRef] [Green Version]
- Li, F.; Yang, X.W. Three new Neolignans from the aril of Myristica fragrans. Helv. Chim. Acta 2007, 90, 1491–1496. [Google Scholar] [CrossRef]
- Kwon, H.Y.; Kim, J.H.; Kim, B.; Srivastava, S.K.; Kim, S.H. Regulation of SIRT1/AMPK axis is critically involved in gallotannin-induced senescence and impaired autophagy leading to cell death in hepatocellular carcinoma cells. Arch. Toxicol. 2018, 92, 241–257. [Google Scholar] [CrossRef]
1 | 2 | 3 | ||||
---|---|---|---|---|---|---|
Position | δC, Type | δH (J in Hz) | δC, Type | δH (J in Hz) | δC, Type | δH (J in Hz) |
1 | 133.7, C | - | 134.3, C | - | 133.6, C | - |
2 | 131.1, CH | 6.95, d (8.4) | 113.8, CH | 6.61, brs | 131.1, CH | 6.93, d (7.9) |
3 | 115.7, CH | 6.64, d (8.4) | 148.4, C | - | 115.7, CH | 6.63, d (7.9) |
4 | 156.2, C | - | 145.3, C | - | 156.2, C | - |
5 | 115.7, CH | 6.64, d (8.4) | 115.6, CH | 6.63, dd (8.0, 1.2) | 115.7, CH | 6.63, d (7.9) |
6 | 131.1, CH | 6.95, d (8.4) | 122.7, CH | 6.57, d (8.0) | 131.1, CH | 6.93, d (7.9) |
7 | 43.4, CH2 | 2.88, dd (13.5, 5.8) 2.55, dd (13.5, 8.8) | 43.8, CH2 | 2.89, dd (13.4, 6.4) 2.60, dd (13.4, 8.1) | 43.4, CH2 | 2.88, dd (13.5, 5.8) 2.55, dd (13.5, 8.7) |
8 | 35.9, CH | 3.33, m | 35.9, C | 3.35, m | 35.8, C | 3.33, m |
9 | 19.9, CH3 | 1.11, d (6.9) | 20.2, CH3 | 1.14, d (6.4) | 19.8, CH3 | 1.12, d (7.0) |
1′ | 132, C | - | 132.0, C | - | 131.8, C | - |
2′ | 119, CH | 6.44, d (1.9) | 119.2, CH | 6.43, brs | 127.5, CH | 6.78, dd (8.3, 2.0) |
3′ | 145.8, C | - | 134.6, C | - | 134.4, C | - |
4′ | 141.9, C | - | 142.0, C | - | 153.9, C | - |
5′ | 134.8, C | - | 145.8, C | - | 115.9, CH | 6.65, d (8.3) |
6′ | 113.7, CH | 6.47, d (1.9) | 113.7, CH | 6.46, brs | 128.4, CH | 6.88, d (2.0) |
7′ | 40.9, CH2 | 3.19, d (6.7) | 40.9, CH2 | 3.19, d (6.8) | 40.7, CH2 | 3.24, d (6.5) |
8′ | 139.7, CH | 5.90, ddt (16.8, 10.2, 6.7) | 139.7, CH | 5.90, m | 139.9, CH | 5.91, m |
9′ | 115.1, CH2 | 5.00, dd (16.8, 1.1) | 115.1, CH2 | 5.00, brd (17.0) | 115.1, CH2 | 4.98, brd (18.0) |
4.97, dd (10.2, 1.1) | 4.97, brd (10.2) | 4.97, brd (8.5) | ||||
3-OCH3 | - | - | 56.2, CH3 | 3.73, s | - | - |
Publisher’s Note: MDPI stays neutral with regard to jurisdictional claims in published maps and institutional affiliations. |
© 2021 by the authors. Licensee MDPI, Basel, Switzerland. This article is an open access article distributed under the terms and conditions of the Creative Commons Attribution (CC BY) license (https://creativecommons.org/licenses/by/4.0/).
Share and Cite
Kim, H.-W.; Jeon, J.-B.; Zhang, M.; Cho, H.-M.; Ryu, B.; Lee, B.-W.; Gerwick, W.H.; Oh, W.-K. SIRT1 Activation Enhancing 8,3′-Neolignans from the Twigs of Corylopsis coreana Uyeki. Plants 2021, 10, 1684. https://doi.org/10.3390/plants10081684
Kim H-W, Jeon J-B, Zhang M, Cho H-M, Ryu B, Lee B-W, Gerwick WH, Oh W-K. SIRT1 Activation Enhancing 8,3′-Neolignans from the Twigs of Corylopsis coreana Uyeki. Plants. 2021; 10(8):1684. https://doi.org/10.3390/plants10081684
Chicago/Turabian StyleKim, Hyun-Woo, Jin-Bum Jeon, Mi Zhang, Hyo-Moon Cho, Byeol Ryu, Ba-Wool Lee, William H. Gerwick, and Won-Keun Oh. 2021. "SIRT1 Activation Enhancing 8,3′-Neolignans from the Twigs of Corylopsis coreana Uyeki" Plants 10, no. 8: 1684. https://doi.org/10.3390/plants10081684