Terpenoids from Glechoma hederacea var. longituba and their biological activities

Abstract

Glechoma hederacea var. longituba (common name: ground ivy) has been used for the treatment of asthma, bronchitis, cholelithiasis, colds, and inflammation. In the present study, three new sesquiterpene glycosides (1–3), two new diterpene glycosides (4 and 5), and four known compounds (6–9) were isolated from its MeOH extract. A structure elucidation was performed for the five new compounds (1–5) using 1D and 2D NMR, HRESIMS, DP4+ and ECD calculations, and chemical methods. All the isolates (1–9) were assessed for their antineuroinflammatory activities on nitric oxide (NO) production in lipopolysaccharide (LPS)-activated BV-2 cells, nerve growth factor (NGF) secretion stimulation activities in C6 glioma cells, and cytotoxic activities against four human cancer cell lines (A549, SK-OV-3, SK-MEL-2, and HCT15). Compounds 2 and 5–7 exhibited inhibitory effects on the NO production with IC50 values of 52.21, 47.90, 61.61, and 25.35 μM, respectively. Compound 5 also exhibited a significant stimulating effect on NGF secretion (122.77 ± 8.10%). Compound 9 showed potent cytotoxic activity against SK-OV-3 (IC50 = 3.76 μM) and SK-MEL-2 (IC50 = 1.48 μM) cell lines, while 7 displayed a strong cytotoxic activity against the SK-MEL-2 (IC50 = 9.81 μM) cell line.

New Aspect of Composition and Biological Properties of Glechoma hederacea L. Herb: Detailed Phytochemical Analysis and Evaluation of Antioxidant, Anticoagulant Activity and Toxicity in Selected Human Cells and Plasma In Vitro

“…Recently, Kim et al [ 51 ] have isolated different terpenoids from G. hederacea , which had various biological properties, including cytotoxic activity against selected human cancer cell lines such as malignant ovarian ascites (SK-OV-3) and skin melanoma (SK-MEL-2). Some of these terpenoids exhibited inhibitory effects on NO production, a significant stimulating effect on nerve growth factor (NGF) secretion in C6 glioma cells, and a neurotrophic effect [ 51 ].…”

Determination of the Absolute Configuration of Secondary Alcohols in a Compound Mixture via the Application of Competing Enantioselective Acylation Coupled with LC/MS Analysis

“…This process entailed the experimental NMR data comparison with the calculated Gauge-Independent Atomic Orbital (GIAO) NMR chemical shifts and δ x calc values for potential isomers. The DP4+ analysis was executed utilizing an Excel sheet [ 30 , 31 , 32 , 33 ].…”

Optimization of the Extraction Procedure for the Phenolic-Rich Glechoma hederacea L. Herb and Evaluation of Its Cytotoxic and Antioxidant Potential

“…Pharmacological effects are most often related to the presence of phenolics, such as phenolic acids and flavonoids, which are found in significant amounts in this plant species [12,[16][17][18][19]. Nevertheless, phytochemical studies on G. hederacea L. aerial parts revealed also the presence of triterpenes and diterpenes, essential oil, alkaloids, fatty acids, and tannins [1,3,[20][21][22][23][24].…”