Insights into the Phytochemistry of the Cuban Endemic Medicinal Plant Phyllanthus orbicularis: Fideloside, a Novel Bioactive 8-C-glycosyl 2,3-Dihydroflavonol

Autor: Antonio Francioso, Katrin Franke, Luciana Mosca, Maria D'Erme, Ludger A. Wessjohann, Wolfgang Brandt, Angel Sánchez-Lamar, Claudio Villani, Stefan Frischbutter
Jazyk: angličtina
Rok vydání: 2019
Předmět:
plant extracts
natural products
Flavonoid
Pharmaceutical Science
molecular structure
01 natural sciences
Fideloside
Analytical Chemistry
chemistry.chemical_compound
Drug Discovery
Phyllanthus orbicularis
high pressure liquid
humans
anti-inflammatory activity
mass spectrometry
chemistry.chemical_classification
medicinal
Traditional medicine
plants
stereochemistry
Cuba
c-glycoside
chromatography
circular dichroism
cuba
cytokines
fideloside
flavonoid
nmr
phyllanthus chamacristoides
phyllanthus orbicularis
traditional medicine
chromatography
high pressure liquid
flavonoids
models
molecular
monocytes
phyllanthus
phytochemicals
plants
medicinal
spectrum analysis
C-glycoside
Phyllanthus chamacristoides
Chemistry (miscellaneous)
Molecular Medicine
Phytochemistry
Chemical structure
Biology
lcsh:QD241-441
models
lcsh:Organic chemistry
Glycosyl
molecular
Physical and Theoretical Chemistry
010405 organic chemistry
Organic Chemistry
Flavanonol
Phyllanthaceae
biology.organism_classification
NMR
0104 chemical sciences
010404 medicinal & biomolecular chemistry
chemistry
Polyphenol
Zdroj: Molecules
Volume 24
Issue 15
Molecules, Vol 24, Iss 15, p 2855 (2019)
ISSN: 1420-3049
DOI: 10.3390/molecules24152855
Popis: Phyllanthus orbicularis (Phyllanthaceae) is an endemic evergreen tropical plant of Cuba that grows in the western part of the island and is used in traditional medicine as an infusion. The aqueous extract of this plant presents a wide range of pharmacological activitiessuch as antimutagenic, antioxidant and antiviral effects. Given the many beneficial effects and the great interest in the development of new pharmacological products from natural sources, the aim of this work was to investigate the phytochemistry of this species and to elucidate the structure of the main bioactive principles. Besides the presence of several known polyphenols, the major constituent was hitherto not described. The chemical structure of this compound, here named Fideloside, was elucidated by means of HR-ESIMS/MSn, 1D/2D NMR, FT-IR, and ECD as (2R,3R)-(&minus
)-3&rsquo
4&prime
5,7-tetrahydroxydihydroflavonol-8-C-&beta
D-glucopyranoside. The compound, as well as the plant aqueous preparations, showed promising bioactive properties, i.e., anti-inflammatory capacity in human explanted monocytes, corroborating future pharmacological use for this new natural C-glycosyl flavanonol.
Databáze: OpenAIRE
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