Back to Search
Start Over
Isolation and Biological Characterization of Homoisoflavanoids and the Alkylamide N-p-Coumaroyltyramine from Crinum biflorum Rottb., an Amaryllidaceae Species Collected in Senegal
- Source :
- Biomolecules, Volume 11, Issue 9, Biomolecules, Vol 11, Iss 1298, p 1298 (2021)
- Publication Year :
- 2021
- Publisher :
- MDPI AG, 2021.
-
Abstract
- 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.
- Subjects :
- antioxidant
Molecular Conformation
Coumaric Acid
HeLa Cell
Biochemistry
HeLa
Alkylamide
chemistry.chemical_compound
Crinum
HaCaT Cells
HaCaT Cell
Cholinesterase Inhibitor
Homoisoflavanoid
Cytotoxicity
Hydrogen peroxide
Antidiabetic and anti‐acetylcholinesterase activitie
Cell Death
biology
antidiabetic and anti-acetylcholinesterase activities
Fluoresceins
QR1-502
Senegal
Acrylamide
Acetylcholinesterase
Metabolome
cytotoxicity
Fluorescein
Human
Coumaric Acids
Cell Survival
Stereochemistry
alkylamides
Crinum biflorum
Microbiology
Antiviral Agents
Article
Humans
Hypoglycemic Agents
Molecular Biology
Flavonoids
Antiviral Agent
Hypoglycemic Agent
Amaryllidaceae
Carbon-13 NMR
biology.organism_classification
HaCaT
homoisoflavanoids
chemistry
Flavonoid
HIV-1
Cholinesterase Inhibitors
alpha-Amylases
HeLa Cells
Subjects
Details
- ISSN :
- 2218273X
- Volume :
- 11
- Database :
- OpenAIRE
- Journal :
- Biomolecules
- Accession number :
- edsair.doi.dedup.....7fd0c8c388f76e38e7d6779cd9e7a16f