UHPLC-DPPH method reveals antioxidant tyramine and octopamine derivatives in Celtis occidentalis

Ayanlowo, Abisola Grace; Garádi, Zsófia; Boldizsár, Imre; Darcsi, András; Nedves, Andrea Nagyné; Varjas, Bence; Simon, Alexandra; Alberti, Ágnes; Riethmüller, Eszter

doi:10.1016/j.jpba.2020.113612

Cited by 33Phytochemistry and Biological ActivitiesPlant chemical constituents analysisMedicinal Plant Research

UHPLC-DPPH method reveals antioxidant tyramine and octopamine derivatives in Celtis occidentalis

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Ayanlowo, Abisola Grace, Garádi, Zsófia, Boldizsár, Imre, Darcsi, András, Nedves, Andrea Nagyné, Varjas, Bence, Simon, Alexandra, Alberti, Ágnes +1 more·2020·Journal of Pharmaceutical and Biomedical Analysis

DOI 10.1016/j.jpba.2020.113612

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Abstract

Celtis occidentalis L. (common Hackberry, Cannabaceae) has been applied in the traditional medicine for a long time as a remedy for sore throat, aid during menstruation and for treating jaundice. Nevertheless, the phytochemical exploration of the plant is still incomplete, literature data is limited to flavonoid derivatives isolated from the leaves. The present study reports screening approaches for bioactive compounds in C. occidentalis by fast and simple UHPLC-coupled assays. The UHPLC-DPPH method revealed six constituents in the methanolic extract of the twigs that had not been reported in C. occidentalis before. The antioxidant compounds were isolated by the means of flash chromatography and semi-preparative HPLC and identified by Orbitrap® MS and NMR spectroscopy as N-trans-p-coumaroyloctopamine (1), N-trans-feruloyloctopamine (2), N-trans-caffeoyltyramine (3), 2-trans-3-(4-hydroxyphenyl)-N-[2-(4-hydroxyphenyl)-2-oxoethyl] prop-2-enamide (4), N-trans-p-coumaroyltryramine (5) and N-trans-feruloyltyramine (6). Despite the high antioxidant activity measured in the present study and literature data suggesting potential positive effects of the compounds in the central nervous system, the PAMPA-BBB assay performed with the Celtis extract revealed that none of the aforementioned compounds are able to penetrate across the blood-brain barrier via transcellular passive diffusion.

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A DPPH assay on Celtis occidentalis extract reported antioxidant activity ranking: N-trans-caffeoyltyramine (IC50 = 31.6 μM) > N-trans-feruloyltyramine (47.9 μM) > N-p-trans-coumaroyltyramine (1378 μM).
“They reported the antioxidant activity of HCAAs as such: N-trans-caffeoyltyramine (IC50 = 31.6 μM) > N-trans-feruloyltyramine (IC50 = 47.9 μM) > N-p-trans-coumaroyltyramine (IC50 = 1378 μM) [77].”
From Exploring the Lesser-Known Bioactive Natural Products of Plant Species of the Genus Cannabis L.: Alkaloids, Phenolic Compounds, and Their Therapeutic Potential (2025) · cites this paper as [77]

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Authors: Ayanlowo, A. G., Garádi, Z., Boldizsár, I., Darcsi, A., Nedves, A. N., Varjas, B., Simon, A., Alberti, Á., & Riethmüller, E.
Affiliations: Semmelweis University (HU)
Eötvös Loránd University (HU)
Corresponding author: Riethmüller, Eszter
ORCID: Garádi, Zsófia
Boldizsár, Imre
Darcsi, András
Nedves, Andrea Nagyné
Simon, Alexandra
Alberti, Ágnes
Riethmüller, Eszter
Venue: Journal of Pharmaceutical and Biomedical Analysis
Publisher: Elsevier BV
Published: 2020-11
Volume: 191
Pages: 113612
ISSN: 0731-7085 (ISSN-L)
DOI: 10.1016/j.jpba.2020.113612
OpenAlex: W3084417922
Cited by: 33
References: 20
Citations by year: 2026: 9 · 2025: 5 · 2024: 9 · 2023: 4 · 2022: 5 · 2021: 1
FWCI: 1.61
Type: journal article
Language: en
Open access: hybrid
doi.org
Licence: cc-by-nc-nd
www.elsevier.com/tdm/userlicense/1.0/ (tdm)
www.elsevier.com/legal/tdmrep-license (tdm)
creativecommons.org/licenses/by-nc-nd/4.0/ (vor)
Locations: Journal of Pharmaceutical and Biomedical Analysis (publishedVersion, cc-by-nc-nd)
PubMed (publishedVersion)
Repository of the Academy's Library (Library of the Hungarian Academy of Sciences) (acceptedVersion)
Funders: Magyar Tudományos Akadémia (1783-3/2018/FEKUTSRAT)
National Research, Development and Innovation Office
Nemzeti Kutatási Fejlesztési és Innovációs Hivatal (FK 125302, K 120342, VEKOP-2.3.3-15-2017-00020)
Topics: Life Sciences › Agricultural and Biological Sciences › Plant Science › Phytochemistry and Biological Activities
Life Sciences › Agricultural and Biological Sciences › Plant Science › Plant chemical constituents analysis
Life Sciences › Agricultural and Biological Sciences › Plant Science › Medicinal Plant Research
Keywords: Celtis occidentalis, hackberry, tyramine derivatives, antioxidants, bioactive compound screening, blood-brain barrier permeability, traditional medicine
MeSH terms: Antioxidants, Chromatography, High Pressure Liquid, Female, Humans, Octopamine, Plant Extracts, Tyramine, Ulmaceae

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UHPLC-DPPH method reveals antioxidant tyramine and octopamine derivatives in Celtis occidentalis

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