Next Article in Journal
Continuous Flow Photochemical and Thermal Multi-Step Synthesis of Bioactive 3-Arylmethylene-2,3-Dihydro-1H-Isoindolin-1-Ones
Next Article in Special Issue
Tepary Bean (Phaseolus acutifolius) Lectins Induce Apoptosis and Cell Arrest in G0/G1 by P53(Ser46) Phosphorylation in Colon Cancer Cells
Previous Article in Journal
Metal Organic Frameworks as Desulfurization Adsorbents of DBT and 4,6-DMDBT from Fuels
Previous Article in Special Issue
Synthesis of Daidzein Glycosides, α-Tocopherol Glycosides, Hesperetin Glycosides by Bioconversion and Their Potential for Anti-Allergic Functional-Foods and Cosmetics
Open AccessCommunication

Characterization of Nine Compounds Isolated from the Acid Hydrolysate of Lonicera fulvotomentosa Hsu et S. C. Cheng and Evaluation of Their In Vitro Activity towards HIV Protease

1
College of Pharmacy, Guizhou University of Traditional Chinese Medicine, South of Dongqing Road, Guiyang 550025, Guizhou Province, China
2
Drug Discovery and Development Research Group, College of Pharmacy and Nutrition, University of Saskatchewan, 107 Wiggins Road, Saskatoon, SK S7N 5E5, Canada
3
Laboratory of Mesoscopic Chemistry, Institute of Theoretical and Computational Chemistry, Nanjing University, Nanjing 210093, Jiangsu Province, China
*
Authors to whom correspondence should be addressed.
Academic Editors: Francesco Epifano and Serena Fiorito
Molecules 2019, 24(24), 4526; https://doi.org/10.3390/molecules24244526
Received: 31 October 2019 / Revised: 7 December 2019 / Accepted: 9 December 2019 / Published: 11 December 2019
(This article belongs to the Special Issue Natural Products as Tools in Drug Discovery and Development)
In this study, we isolated nine compounds from the acid hydrolysate of the flower buds of Lonicera fulvotomentosa Hsu et S. C. Cheng and characterized their chemical structures using 1H-NMR, 13C-NMR, and electron ionization mass spectroscopy (EI-MS). These compounds were identified as β-sitosterol (1), 5,5′-dibutoxy-2,2′-bifuran (2), nonacosane-10-ol (3), ethyl (3β)-3,23-dihydroxyolean-12-en-28-oate (4), oleanolic acid (5), ethyl caffeate (6), caffeic acid (7), isovanillin (8), and hederagenin (9), with 4 as a new triterpene compound. Inhibitory activity against human immunodeficiency virus (HIV) protease was also evaluated for the compounds, and only ethyl caffeate, caffeic acid, and isovanillin (6, 7, and 8) exhibited inhibitory effects, with IC50 values of 1.0 μM, 1.5 μM, and 3.5 μM, respectively. Molecular docking with energy minimization and subsequent molecular dynamic (MD) simulation showed that ethyl caffeate and caffeic acid bound to the active site of HIV protease, while isovanillin drifted out from the active site and dissociated into bulk water during MD simulations, and most of the binding residues of HIV protease have been previously identified for HIV protease inhibitors. These results suggest that caffeic acid derivatives may possess inhibitory activities towards HIV protease other than previously reported inhibitory activities against HIV integrase, and thus ethyl caffeate and caffeic acid could be used as lead compounds in developing potential HIV protease inhibitors, and possibly even dual-function inhibitors against HIV. View Full-Text
Keywords: Lonicera fulvotomentosa Hsu et S. C. Cheng; acid hydrolysate; HIV protease; molecular docking; inhibitor Lonicera fulvotomentosa Hsu et S. C. Cheng; acid hydrolysate; HIV protease; molecular docking; inhibitor
Show Figures

Figure 1

MDPI and ACS Style

Wang, X.; Wei, Y.; Tian, W.-Y.; Sakharkar, M.K.; Liu, Q.; Yang, X.; Zhou, Y.-Z.; Mou, C.-L.; Cai, G.-L.; Yang, J. Characterization of Nine Compounds Isolated from the Acid Hydrolysate of Lonicera fulvotomentosa Hsu et S. C. Cheng and Evaluation of Their In Vitro Activity towards HIV Protease. Molecules 2019, 24, 4526.

Show more citation formats Show less citations formats
Note that from the first issue of 2016, MDPI journals use article numbers instead of page numbers. See further details here.

Article Access Map by Country/Region

1
Search more from Scilit
 
Search
Back to TopTop