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Bionmr-Based Identification of Natural Anti-Aβ Compounds In Bioorganic Chemistry 83 (2019) 76–86 Contents lists available at ScienceDirect Bioorganic Chemistry journal homepage: www.elsevier.com/locate/bioorg bioNMR-based identification of natural anti-Aβ compounds in Peucedanum T ostruthium ⁎ Alessandro Palmiolia,b, , Sara Bertuzzia, Ada De Luigic, Laura Colomboc, Barbara La Ferlaa, ⁎ Mario Salmonac, Ivano De Nonid, Cristina Airoldia,b, a Department of Biotechnology and Biosciences, University of Milano – Bicocca, P.zza della Scienza 2, 20126 Milan, Italy b NeuroMI, Milan Center for Neuroscience, University of Milano – Bicocca, 20126 Milano, Italy c Department of Molecular Biochemistry and Pharmacology – Istituto di Ricerche Farmacologiche “Mario Negri” IRCCS, Via G. La Masa 19, 20156 Milano, Italy d Department of Food, Environmental and Nutritional Sciences, University of Milano, Via Celoria 2, 20133 Milano, Italy ARTICLE INFO ABSTRACT Keywords: The growing interest in medicinal plants for the identification of new bioactive compounds and the formulation Alzheimer’s disease of new nutraceuticals and drugs prompted us to develop a powerful experimental approach allowing the detailed Anti-amyloidogenic compounds metabolic profiling of complex plant extracts, the identification of ligands of macromolecular targets ofbio- Chlorogenic acids medical relevance and a preliminary characterization of their biological activity. To this end, we selected Furanocoumarins Peucedanum ostruthium, a plant traditionally employed in Austria and Italy for its several potential therapeutic NMR spectroscopy applications, as case study. We combined the use of NMR and UPLC-HR-MS for the identification of the meta- Peucedanum ostruthium UPLC-HR-MS bolites present in its leaves and rhizome extracts. Due to the significant content of polyphenols, particularly chlorogenic acids, recently identified as anti-amyloidogenic compounds, polyphenols-enriched fractions were prepared and tested for their ability to prevent Aβ1-42 peptide aggregation and neurotoxicity in a neuronal human cell line. STD-NMR experiments allowed the detailed identification of Aβ oligomers’ ligands responsible for the anti-amyloidogenic activity. These data provide experimental protocols and structural information sui- table for the development of innovative molecular tools for prevention, therapy and diagnosis of Alzheimer’s disease. 1. Introduction and respiratory diseases [1]. The alcohol extract of the rhizome (Radix imperatoriae) has been used as a stimulant, a stomachic, a diuretic for The biological activity of medicinal plants is mainly due to the chronic indigestion, as well as a therapeutic for typhoid, intermittent presence of secondary metabolites, compounds with no apparent fever, paralytic conditions, and in delirium treatment [2]. Furthermore, function in the primary metabolism of the organism, but with a re- its use as anti-inflammatory agent is also documented [3]. markable importance in defense, competition and adaptation to the Coumarins are the most peculiar secondary metabolites found in environment. These molecules often have specific functions and many this species. In particular, the presence of imperatorin, ostruthol, oxy- of them present biological activities that can be useful for the treatment peucedanin hydrate, oxypeucedanin, isoimperatorin (all fur- of human diseases, therefore providing new active ingredients for anocoumarins) and ostruthin and osthole is reported [1]. Coumarins are pharmacological research. related to a wide range of biological activities such as antiinflammatory Due to the growing interest in medicinal plants for the discovery and antioxidant [4], anticancer [5], antifungal and antimicrobial [6] and rational design of new drugs, we decided to investigate the meta- activity. In addition, ostruthol acts as inhibitor of acetylcholinesterase, bolic content and the potential biological activities of the species which could imply a strong potential for the treatment of Alzheimer's Peucedanum ostruthium (vernacular name “Imperatoria”). This plant is disease (AD) [7]. traditionally employed in Austria and Italy. The parts of Peucedanum The many therapeutic applications of Imperatoria prompted us to ostruthium with documented uses are the leaves and the rhizome, further deepen its secondary metabolite content by combining NMR commonly used for the preparation of tisanes, liqueurs and bitters, or as spectroscopy and UPLC coupled with high resolution mass spectrometry powders applied on the skin to treat gastro-intestinal, cardiovascular (HR-MS). ⁎ Corresponding authors at: Department of Biotechnology and Biosciences, University of Milano – Bicocca, P.zza della Scienza 2, 20126 Milan, Italy. E-mail addresses: [email protected] (A. Palmioli), [email protected] (C. Airoldi). https://doi.org/10.1016/j.bioorg.2018.10.016 Received 5 September 2018; Received in revised form 7 October 2018; Accepted 9 October 2018 Available online 12 October 2018 0045-2068/ © 2018 Elsevier Inc. All rights reserved. A. Palmioli et al. Bioorganic Chemistry 83 (2019) 76–86 Interestingly, a first metabolic profiling of different kinds of aqueous 2.3. Chemical characterization and hydro-alcoholic extracts revealed the significant presence of chlorogenic acids (CGAs). By dissecting the potential neuroprotective 2.3.1 NMR spectroscopy activity of both roasted and green coffee extracts, we recently demon- Freeze-dried samples were suspended in D2O at a final concentra- strated that CGAs show interesting anti-amyloidogenic properties [8]. tion of 25 mg/mL, sonicated (37 kHz, 20 min, Elmasonic P 30H, Elma Briefly, CGAs are Aβ oligomer ligands able to inhibit Aβ1-42 peptide Schmidbauer GmbH, Singen, Germany) and centrifuged (14,000 rpm, on-pathway aggregation and Aβ-induced toxicity in SH-SY5Y human 5 min, 20 °C, ScanSpeed 1730R Labogene, Lynge, Sweden). 4,4- neuroblastoma cell line, suggesting the potential application of coffee Dimethyl-4-silapentane-1-sulfonic acid (DSS, final concentration extracts for AD prevention [8]. AD is the most common form of de- 0.5 mM) was added to the supernatant as an internal reference for mentia in older population and the number of people affected is ex- concentrations and chemical shift. The pH of each sample was verified pected to increase dramatically in coming years [9]. Since symptom with a microelectrode (Mettler Toledo, Columbus, OH, USA) for 5 mm treatments occur in a stage of the disease in which neuronal damage is NMR tubes and adjusted to 7.4 with NaOD or DCl. All pH values were irreversible, there is a strong need to identify a primary prevention corrected for the isotope effect. The acquisition temperature was 25°C. treatment for AD, and Aβ oligomers are a promising target for this All spectra were acquired on an Avance III 600 MHz NMR spectrometer purpose [9]. Thus, the interest in natural compounds capable of inter- (Bruker, Billerica, MA, USA) equipped with a QCI (1H, 13C, 15N/31P and fering with toxic oligomers of Aβ peptides is growing. 2H lock) cryogenic probe. 1H NMR spectra were recorded with Based on these evidences, we decided to perform a preliminary in- cpmgpr1d, noesygppr1d, ledbpgppr2s1d pulse sequences (Bruker library) vestigation of the nutraceutical potential of Peucedanum ostruthium ex- and 256 scans, spectral width 20 ppm, relaxation delay 5 s. They were tracts for the prevention of AD. To this end, the chemical analysis done processed with 0.3 Hz line broadening, automatically phased and through NMR and UPLC-HR-MS was complemented with biochemical, baseline corrected. Chemical shifts were internally calibrated to the DSS biophysical and biological assays, the last carried out on SH-SY5Y peak at 0.0 ppm. Compound identification and assignment were done human neuroblastoma cell line. with the support of 2D NMR experiments, comparison with reported assignments and the SMA analysis tool integrated in MestreNova 2. Experimental section Software. The 1H,1H-TOCSY (Total Correlation SpectroscopY) spectra were acquired with 48 scans and 512 increments, a mixing time of All chemicals and solvents were purchased from Sigma-Aldrich or 80 ms and relaxation delay of 2 s. 1H, 13C-HSQC (Heteronuclear Single Fisher scientific and used without further purification. Quantum Coherence) spectra were acquired with 64 scans and 512 increments, relaxation delay 2 s. 2.1. Preparation of plant extracts 2.3.2 Ultra-performance liquid chromatography/electrospray ionization- Samples of Peaucedanum ostruthium (rhizome and leaves) were field- high resolution mass spectrometry (UPLC/ESI-HR-MS) collected (Barmasc, Rû Courtod, Ayas, AO, Italy, 1900 mt above sea The UPLC/ESI-HR-MS analysis was carried by coupling an Acquity level) on August 13, 2016 and identified by a local ethnobotanical UPLC separation module (Waters, Milford, MA, USA) with in-line expert (Dr. Fiorenza Cout). photodiode array (PDA) eλ detector (Waters) to a Q Exactive hybrid Samples were frozen in liquid nitrogen and grounded into a fine quadrupole-Orbitrap mass spectrometer and an HESI-II probe for elec- powder. 1 g of each sample was introduced into a cellulose thimble and trospray ionization (Thermo Scientific, San Jose, CA, USA). The ion extracted in a Soxhlet apparatus (100 mL) with a hydroalcoholic mix- source and interface conditions were: spray voltage +3.0/−2.5 kV, ture (80% EtOH) during 10 cycles. Finally, the organic phase was re- sheath gas flow 60, auxiliary gas flow 20 and temperature 300 °C,ca- moved under reduced pressure at 40 °C and the aqueous residue was pillary temperature 350 °C. Positive
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