BJOC - Terpenoids from Glechoma hederacea var. longituba and their biological activities

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Supporting Information File 1: HRESIMS and 1D and 2D NMR data of compounds 1–5, experimental ECD data of 1–3, comparison with standard samples and monosaccharides of 1–5, coordinates of the conformers, cytotoxic activity, NO production, NGF secretion, and cell viability assays.
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Terpenoids from Glechoma hederacea var. longituba and their biological activities

Dong Hyun Kim, Song Lim Ham, Zahra Khan, Sun Yeou Kim, Sang Un Choi, Chung Sub Kim and Kang Ro Lee

Beilstein J. Org. Chem. 2022, 18, 555–566. https://doi.org/10.3762/bjoc.18.58

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Kim, D. H.; Ham, S. L.; Khan, Z.; Kim, S. Y.; Choi, S. U.; Kim, C. S.; Lee, K. R. Beilstein J. Org. Chem. 2022, 18, 555–566. doi:10.3762/bjoc.18.58

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TY  - JOUR
A1  - Kim, Dong Hyun
A1  - Ham, Song Lim
A1  - Khan, Zahra
A1  - Kim, Sun Yeou
A1  - Choi, Sang Un
A1  - Kim, Chung Sub
A1  - Lee, Kang Ro
T1  - Terpenoids from Glechoma hederacea var. longituba and their biological activities
JF  - Beilstein Journal of Organic Chemistry
PY  - 2022///
VL  - 18
SP  - 555
EP  - 566
SN  - 1860-5397
DO  - 10.3762/bjoc.18.58
PB  - Beilstein-Institut
JA  - Beilstein J. Org. Chem.
UR  - https://doi.org/10.3762/bjoc.18.58
KW  - antineuroinflammation
KW  - cytotoxicity
KW  - Glechoma hederacea var. longituba
KW  - neurotrophic effect
KW  - terpenoid
N2  - 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.
ER  -

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Lee, B. S.; Kim, H.; Baek, J.; Ryoo, R.; Lee, S. R.; Kim, K. H. Determination of the Absolute Configuration of Secondary Alcohols in a Compound Mixture via the Application of Competing Enantioselective Acylation Coupled with LC/MS Analysis. Pharmaceutics 2024, 16, 364. doi:10.3390/pharmaceutics16030364
Yuan, M.-M.; Xu, F.; Zheng, Y.-B.; Zhou, L.-G.; Deng, Y.; Zhou, G.-P.; Wu, X.; Ji, T.-F. Diverse terpenoid glycosides with in vitro cytotoxicity from Glechoma longituba. Phytochemistry 2023, 217, 113923. doi:10.1016/j.phytochem.2023.113923
Sławińska, N.; Kluska, M.; Moniuszko-Szajwaj, B.; Stochmal, A.; Woźniak, K.; Olas, B. 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. Nutrients 2023, 15, 1671. doi:10.3390/nu15071671
Grabowska, K.; Amanowicz, K.; Paśko, P.; Podolak, I.; Galanty, A. Optimization of the Extraction Procedure for the Phenolic-Rich Glechoma hederacea L. Herb and Evaluation of Its Cytotoxic and Antioxidant Potential. Plants (Basel, Switzerland) 2022, 11, 2217. doi:10.3390/plants11172217

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