Isolation and Biological Characterization of Homoisoflavanoids and the Alkylamide N-p-Coumaroyltyramine from Crinum biflorum Rottb., an Amaryllidaceae Species Collected in Senegal
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Crinum biflorum Rottb. (syn. Crinum distichum) is an Amaryllidaceae plant used in African traditional medicine but very few studies have been performed on this species from a chemical and applicative point of view. Bulbs of C. biflorum, collected in Senegal, were extracted with ethanol by Soxhlet and the corresponding organic extract was purified using chromatographic methods. The pure compounds were chemically characterized by spectroscopic techniques (1D and 2D 1H and 13C NMR, HR MS and ECD) and X-ray analysis. Four homoisoflavonoids (1–4) and one alkylamide (5) were isolated and characterized as 5,6,7-trimethoxy-3-(4-hydroxybenzyl)chroman-4-one (1), as 3-hydroxy-5,6,7-trimethoxy-3-(4-hydroxybenzyl)chroman-4-one (2), as 3-hydroxy-5,6,7-trimethoxy-3-(4-methoxybenzyl)chroman-4-one (3) and as 5,6,7-trimethoxy-3-(4-methoxybenzyl)chroman-4-one (4), and the alkylamide as (E)-N-(4-hydroxyphenethyl)-3-(4-hydroxyphenyl)acrylamide (5), commonly named N-p-coumaroyltyramine. The relative configuration of compound 1 was verified thanks to the X-ray analysis which also allowed us to confirm its racemic nature. The absolute configurations of compounds 2 and 3 were assigned by comparing their ECD spectra with those previously reported for urgineanins A and B. Flavanoids 1, 3 and 4 showed promising anticancer properties being cytotoxic at low micromolar concentrations towards HeLa and A431 human cancer cell lines. The N-p-coumaroyltyramine (5) was selectively toxic to A431 and HeLa cancer cells while it protected immortalized HaCaT cells against oxidative stress induced by hydrogen peroxide. Compounds 1–4 also inhibited acetylcholinesterase activity with compound 3 being the most potent. The anti-amylase and the strong anti-glucosidase activity of compound 5 were confirmed. Our results show that C. biflorum produces compounds of therapeutic interest with anti-diabetic, anti-tumoral and anti-acetylcholinesterase properties.
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N-p-trans-coumaroyltyramine significantly reduces HeLa and A431 cell viability in a dose- and time-dependent manner, at 10 μM for 24 h and 5 μM for 48 h.
“Its antiproliferative activity was tested on HeLa (cervical cancer) and A431 (epidermoid carcinoma) cell lines and it was found that N-p-trans-coumaroyltyramine significantly reduced cell viability in a dose- and time-dependent manner, at 10 μM for a 24 h treatment, and at 5 μM for 48 h of exposure [68].”
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 [68]
Results §3.2 reports that N-p-coumaroyltyramine was toxic to HeLa and A431 cells and that the tested metabolites acted in a dose- and time-dependent manner. It does not specifically report a significant viability reduction for this compound at 10 μM after 24 h or 5 μM after 48 h; the explicit 5 μM, 48 h result concerns metabolite 1, not N-p-coumaroyltyramine (metabolite 5). (LLM, conf=0.88)
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- Authors
- Masi, M., Koirala, M., Delicato, A., Di Lecce, R., Merindol, N., Ka, S., Seck, M., Tuzi, A., Desgagne-Penix, I., Calabrò, V., & Evidente, A.
- Affiliations
- University of Naples Federico II (IT)
- Université du Québec à Trois-Rivières (CA)
- Dipartimento di Scienze Chimiche, Universita’ di Napoli Federico II, Complesso Universitario Monte Sant’Angelo, Via Cintia 4, 80126 Napoli, Italy
- Département de Chimie, Biochimie et Physique, Université du Québec à Trois-Rivières, 3351, Boul. des Forges, C.P. 500, Trois-Rivières, QC G8Z 4M3, Canada
- Cheikh Anta Diop University (SN)
- Corresponding author
- Masi, Marco
- Calabrò, Viola
- ORCID
- Venue
- Biomolecules
- Publisher
- MDPI AG
- Published
- 2021-08-31
- Volume
- 11
- Issue
- 9
- Pages
- 1298
- ISSN
- 2218-273X (ISSN-L)
- PMC
- PMC8466962
- OpenAlex
- W3198268993
- Cited by
- 25
- References
- 73
- Citations by year
- 2026: 5 · 2025: 5 · 2024: 8 · 2023: 3 · 2022: 3 · 2021: 1
- FWCI
- 1.49
- Type
- journal article
- Language
- en
- Open access
- gold
- doi.org
- Licence
- Locations
- Biomolecules (publishedVersion, cc-by)
- Europe PMC (PubMed Central) (publishedVersion, other-oa)
- PubMed Central (publishedVersion, cc-by)
- PubMed (publishedVersion)
- Archivio istituzionale della ricerca (Alma Mater Studiorum Università di Bologna) (submittedVersion, cc-by)
- Le dépôt institutionnel (Université du Québec à Trois-Rivières) (submittedVersion)
- DOAJ (DOAJ: Directory of Open Access Journals) (submittedVersion, cc-by-sa)
- Funders
- Canada Research Chairs (950-232164)
- Topics
- Physical Sciences › Chemistry › Organic Chemistry › Chemical synthesis and alkaloids
- Life Sciences › Biochemistry, Genetics and Molecular Biology › Molecular Biology › Bioactive natural compounds
- Life Sciences › Agricultural and Biological Sciences › Plant Science › Phytochemistry and Biological Activities
- Keywords
- homoisoflavonoids, alkylamides, Amaryllidaceae, natural product isolation, absolute configuration, anticancer activity, cytotoxicity, HeLa cells, A431 cells, acetylcholinesterase inhibition, α-glucosidase inhibition, α-amylase inhibition, antioxidant activity, hydrogen peroxide, traditional medicine, bulbs, X-ray crystal structure, electronic circular dichroism
- MeSH terms
- Amaryllidaceae, HaCaT Cells, Acetylcholinesterase, alpha-Amylases, Antiviral Agents, Cell Survival, Cholinesterase Inhibitors, Coumaric Acids, Flavonoids, Fluoresceins, HeLa Cells, Humans, Hypoglycemic Agents, Molecular Conformation, Senegal, HIV-1, Cell Death, Crinum, Metabolome
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