Abstract
From an EtOAc-soluble fraction of the stem barks of Swintonia floribunda (Anacardiaceae), decumbic anhydride (1) and four known compounds 2–5 were isolated. Their chemical structures were elucidated based on the spectroscopic data interpretation. The GIAO-DFT calculation of 13C NMR chemical shifts was carried out to clarify the structure of 1. The absolute configuration of 1 was assigned based on the Cotton effects in its ECD spectrum. Compound 1 showed potent tyrosinase inhibitory activity with an IC50 value of 52.2 μM.
Funding source: Viet Nam National University Ho Chi Minh City
Award Identifier / Grant number: C2019-18-12
Acknowledgments
This research is funded by Vietnam National University Ho Chi Minh City (VNUHCM) under grant number C2019-18-12, to Phu Hoang Dang.
Author contribution: All the authors have accepted responsibility for the entire content of this submitted manuscript and approved submission.
Research funding: This research is funded by Vietnam National University Ho Chi Minh City (VNUHCM) under grant number C2019-18-12, to Phu Hoang Dang.
Conflict of interest statement: The authors declare no conflicts of interest regarding this article.
References
1. Rodríguez-López, JN, Tudela, J, Varón, R, García-Carmona, F, García-Cánovas, F. Analysis of a kinetic model for melanin biosynthesis pathway. J Biol Chem 1992;267:3801–10.10.1016/S0021-9258(19)50597-XSearch in Google Scholar
2. Decker, H, Tuczek, F. Tyrosinase/catecholoxidase activity of hemocyanins: structural basis and molecular mechanism. Trends Biochem Sci 2000;25:392–7. https://doi.org/10.1016/s0968-0004(00)01602-9.Search in Google Scholar
3. Pillaiyar, T, Manickam, M, Namasivayam, V. Skin whitening agents: medicinal chemistry perspective of tyrosinase inhibitors. J Enzyme Inhib Med Chem 2017;32:403–25. https://doi.org/10.1080/14756366.2016.1256882.Search in Google Scholar
4. Nguyen, NT, Nguyen, MHK, Nguyen, HX, Bui, NKN, Nguyen, MTT. Tyrosinase inhibitors from the wood of Artocarpus heterophyllus. J Nat Prod 2012;75:1951–5. https://doi.org/10.1021/np300576w.Search in Google Scholar
5. Nguyen, HX, Nguyen, NT, Nguyen, MHK, Le, TH, Van Do, TN, Hung, TM, et al. Tyrosinase inhibitory activity of flavonoids from Artocarpus heterophyllous. Chem Cent J 2016;10:2. https://doi.org/10.1186/s13065-016-0150-7.Search in Google Scholar
6. Le, TH, Nguyen, HX, Do, TVN, Dang, PH, Nguyen, NT, Nguyen, MTT. Moracin VN, a new tyrosinase and xanthine oxidase inhibitor from the woods of Artocarpus heterophyllus. Nat Prod Commun 2017;12:925–7. https://doi.org/10.1177/1934578x1701200623.Search in Google Scholar
7. Dang, PH, Nguyen, TT, Le, TH, Nguyen, HX, Nguyen, MTT, Nguyen, NT. A new bischromanone from the stems of Semecarpus caudata. Nat Prod Res 2018;32:1745–50. https://doi.org/10.1080/14786419.2017.1399391.Search in Google Scholar
8. Do, LT. Vietnamese traditional medicinal plants and drugs. Hanoi: Publishing House of Medicine; 2001.Search in Google Scholar
9. Dang, PH, Nguyen, LTT, Nguyen, HTT, Le, TH, Do, TNV, Nguyen, HX, et al. A new dimeric alkylresorcinol from the stem barks of Swintonia floribunda (Anacardiaceae). Nat Prod Res 2019;33:2883–9. https://doi.org/10.1080/14786419.2018.1509329.Search in Google Scholar
10. Dang, PH, Nguyen, HX, Le, TH, Do Van, TN, Nguyen, NT, Nguyen, MTT Chemical constituents of the stem barks of Swintonia floribunda Griff. (Anacardiaceae). Sci Tech Dev J Nat Sci 2018;2:71–75. https://doi.org/10.32508/stdjns.v2i1.677.Search in Google Scholar
11. Dang, PH, Le, TH, Do Van, TN, Nguyen, HX, Nguyen, MTT, Nguyen, NT. Flavonoids from the stem barks of Swintonia griffithii Kurz (Anacadiaceae) and their tyrosinase inhibitory activities. Vietnam J Chem 2019;57:581–4. https://doi.org/10.1002/vjch.201900080.Search in Google Scholar
12. Yi, JH, Zhang, GL, Li, BG, Chen, YZ. Two glycosides from the stem bark of Tetracentron sinense. Phytochemistry 2000;53:1001–3. https://doi.org/10.1016/s0031-9422(99)00457-4.Search in Google Scholar
13. Ma, Q, Liu, Y, Zhan, R, Chen, Y. A new isoflavanone from the trunk of Horsfieldia pandurifolia. Nat Prod Res 2016;30:131–7. https://doi.org/10.1080/14786419.2015.1043554.Search in Google Scholar
14. Xia, Q, Zhang, H, Sun, X, Zhao, H, Wu, L, Zhu, D, et al. A comprehensive review of the structure elucidation and biological activity of triterpenoids from Ganoderma spp. Molecules 2014;19:17478–535. https://doi.org/10.3390/molecules191117478.Search in Google Scholar
15. Zhou, XM, Zheng, CJ, Wu, JT, Chen, GY, Chen, J, Sun, CG. Five new lactone derivatives from the stems of Dendrobium nobile. Fitoterapia 2016;115:96–100. https://doi.org/10.1016/j.fitote.2016.10.002.Search in Google Scholar
16. Williamson, KL, Hasan, MU, Clutter, DR. Conformational analysis by NMR. 13C nuclear magnetic resonance spectra of saturated and unsaturated carboxylic acids and their corresponding esters and anhydrides. J Magn Reson (1969) 1978;30:367–83. https://doi.org/10.1016/0022-2364(78)90107-5.Search in Google Scholar
17. Luiz Paranhos Costa, F, de Albuquerque, ACF, Borges, RM, dos Santos Junior, FM, de Amorim, MB. High cost-effectiveness ratio: GIAO-mPW1PW91/6-31G(d)//mPW1PW91/6-31G(d) scaling factor for 13C nuclear magnetic resonance chemical shifts calculation. J Comput Theor Nanos 2014;11:219–25. https://doi.org/10.1166/jctn.2014.3341.Search in Google Scholar
18. Uchida, I, Kuriyama, K. The π-π* circular dichroism of α,β-unsaturated γ-lactones. Tetrahedron Lett 1974;15:3761−4. https://doi.org/10.1016/s0040-4039(01)92002-7.Search in Google Scholar
19. Beecham, AF. The CD of α,β-unsaturated lactones. Tetrahedron 1972;28:5543−54. https://doi.org/10.1016/s0040-4020(01)93618-x.Search in Google Scholar
20. Gawronski, JK, van Oeveren, A, van der Deen, H, Leung, CW, Feringa, BL. Simple circular dichroic method for the determination of absolute configuration of 5-substituted 2(5H)-furanones. J Org Chem 1996;61:1513−5. https://doi.org/10.1021/jo951400l.Search in Google Scholar
21. Barone, G, Gomez-Paloma, L, Duca, D, Silvestri, A, Riccio, R, Bifulco, G. Structure validation of natural products by quantum-mechanical GIAO calculations of 13C NMR chemical shifts. Chem Eur J 2002;8:3233–9. https://doi.org/10.1002/1521-3765(20020715)8:14<3233::aid-chem3233>3.0.co;2-0.10.1002/1521-3765(20020715)8:14<3233::AID-CHEM3233>3.0.CO;2-0Search in Google Scholar
22. Pierens, GK, Venkatachalam, TK, Reutens, DC. Comparison of experimental and DFT-calculated NMR chemical shifts of 2-amino and 2-hydroxyl substituted phenyl benzimidazoles, benzoxazoles and benzothiazoles in four solvents using the IEF-PCM solvation model. Magn Reson Chem 2016;54:298–307. https://doi.org/10.1002/mrc.4374.Search in Google Scholar
Supplementary material
Conformational data of decumbic acid (Table S1) and copies of spectroscopic data for 1 (Figures S1–S5).
The online version of this article offers supplementary material (https://doi.org/10.1515/znc-2020-0136).
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