Bioactive Pentacyclic Triterpenes from the Root Bark Extract of Myrianthus arboreus, a Species Used Traditionally to Treat Type-2 Diabetes

Journal of Natural Products
2018.0

Abstract

Four new Δ<sup>12</sup> ursene-type pentacyclic triterpenes containing the trans-feruloyl moiety (1-4), along with ursolic acid (5), were isolated from a Myrianthus arboreus root bark ethanol extract, after bioassay-guided subfractionation of its hexane fraction. The structures of 1-4 were established on the basis of the results of standard spectroscopic analytical methods (IR, HRESIMS, GC-MS, 1D and 2D NMR). The compounds 3β- O- trans-feruloyl-2α,19α-dihydroxyurs-12-en-28-oic acid (1), 2α-acetoxy-3β- O- trans-feruloyl-19α-hydroxyurs-12-en-28-oic acid (3), and 5 were determined to decrease the activity of hepatocellular glucose-6-phosphatase (G6Pase) and to activate glycogen synthase (GS). Their action on G6Pase activity implicated both Akt and AMPK activation. In addition, these compounds were determined to stimulate GS via the phosphorylation of glycogen synthase kinase-3. Compound 3 showed the most potent effect in modulating glucose homeostasis in liver cells. This is the first comprehensive report on novel phytochemical components of the root bark extract of M. arboreus based on the isolation of the principles responsible for its antidiabetic effects.

Knowledge Graph

Similar Paper

Bioactive Pentacyclic Triterpenes from the Root Bark Extract of <i>Myrianthus arboreus</i>, a Species Used Traditionally to Treat Type-2 Diabetes
Journal of Natural Products 2018.0
Bioassay-Guided Isolation of the Antidiabetic Principle from <i>Sorbus decora</i> (Rosaceae) Used Traditionally by the Eeyou Istchee Cree First Nations
Journal of Natural Products 2010.0
Antidiabetic potential of phytochemicals isolated from the stem bark of Myristica fatua Houtt. var. magnifica (Bedd.) Sinclair
Bioorganic &amp; Medicinal Chemistry 2018.0
Glucose Uptake-Stimulating Galloyl Ester Triterpenoids from <i>Castanopsis sieboldii</i>
Journal of Natural Products 2020.0
Prenylated Phenolic Compounds from the Aerial Parts of <i>Glycyrrhiza uralensis</i> as PTP1B and α-Glucosidase Inhibitors
Journal of Natural Products 2020.0
Antidiabetic activity of some pentacyclic acid triterpenoids, role of PTP–1B: In vitro, in silico, and in vivo approaches
European Journal of Medicinal Chemistry 2011.0
Triterpenoids from the Leaves of <i>Diospyros kaki</i> (Persimmon) and Their Inhibitory Effects on Protein Tyrosine Phosphatase 1B
Journal of Natural Products 2008.0
Tadehaginosides A–J, Phenylpropanoid Glucosides from<i>Tadehagi triquetrum</i>, Enhance Glucose Uptake via the Upregulation of PPARγ and GLUT-4 in C2C12 Myotubes
Journal of Natural Products 2016.0
Antidiabetic activity of phenolic compounds from Pecan bark in streptozotocin-induced diabetic rats
Phytochemistry Letters 2011.0
Terpenoids from Tripterigyum hypoglaucum
Phytochemistry 2000.0