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Anti-Inflammatory, Antidiabetic Properties and In Silico Modeling of Cucurbitane-Type Triterpene Glycosides from Fruits of an Indian Cultivar of Momordica charantia L
- Source :
- Molecules, Molecules, Vol 26, Iss 1038, p 1038 (2021), Volume 26, Issue 4
- Publication Year :
- 2021
- Publisher :
- MDPI, 2021.
-
Abstract
- Diabetes mellitus is a chronic disease and one of the fastest-growing health challenges of the last decades. Studies have shown that chronic low-grade inflammation and activation of the innate immune system are intimately involved in type 2 diabetes pathogenesis. Momordica charantia L. fruits are used in traditional medicine to manage diabetes. Herein, we report the purification of a new 23-O-β-d-allopyranosyl-5β,19-epoxycucurbitane-6,24-diene triterpene (charantoside XV, 6) along with 25ξ-isopropenylchole-5(6)-ene-3-O-β-d-glucopyranoside (1), karaviloside VI (2), karaviloside VIII (3), momordicoside L (4), momordicoside A (5) and kuguaglycoside C (7) from an Indian cultivar of Momordica charantia. At 50 µM compounds, 2-6 differentially affected the expression of pro-inflammatory markers IL-6, TNF-α, and iNOS, and mitochondrial marker COX-2. Compounds tested for the inhibition of α-amylase and α-glucosidase enzymes at 0.87 mM and 1.33 mM, respectively. Compounds showed similar α-amylase inhibitory activity than acarbose (0.13 mM) of control (68.0-76.6%). Karaviloside VIII (56.5%) was the most active compound in the α-glucosidase assay, followed by karaviloside VI (40.3%), while momordicoside L (23.7%), A (33.5%), and charantoside XV (23.9%) were the least active compounds. To better understand the mode of binding of cucurbitane-triterpenes to these enzymes, in silico docking of the isolated compounds was evaluated with α-amylase and α-glucosidase.
- Subjects :
- Momordica charantia
Proton Magnetic Resonance Spectroscopy
Anti-Inflammatory Agents
Molecular Conformation
Pharmaceutical Science
Ligands
01 natural sciences
Analytical Chemistry
Mice
chemistry.chemical_compound
Triterpene
Drug Discovery
Glycosides
Momordicoside
anti-inflammatory activity
Acarbose
chemistry.chemical_classification
Momordica
biology
Traditional medicine
Molecular Docking Simulation
cucurbitane-type triterpene glycosides
Chemistry (miscellaneous)
Molecular Medicine
Biological Assay
α-glucosidase
medicine.drug
medicine.drug_class
in silico study
charantoside XV
Cucurbitane
Anti-inflammatory
Article
lcsh:QD241-441
lcsh:Organic chemistry
medicine
Animals
Hypoglycemic Agents
Computer Simulation
RNA, Messenger
Carbon-13 Magnetic Resonance Spectroscopy
Physical and Theoretical Chemistry
010405 organic chemistry
Organic Chemistry
Glycoside
alpha-Glucosidases
biology.organism_classification
Triterpenes
0104 chemical sciences
010404 medicinal & biomolecular chemistry
α-amylase
RAW 264.7 Cells
Enzyme
chemistry
Fruit
alpha-Amylases
Subjects
Details
- Language :
- English
- ISSN :
- 14203049
- Volume :
- 26
- Issue :
- 4
- Database :
- OpenAIRE
- Journal :
- Molecules
- Accession number :
- edsair.doi.dedup.....55fcc680e617cab6508d08189fcaf4c8