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Ginkwanghols A and B, osteogenic coumaric acid-aliphatic alcohol hybrids from the leaves of Ginkgo biloba

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Abstract

Ginkgo biloba (Ginkgoaceae), commonly known as “ginkgo”, is called a living fossil, and it has been cultivated early in human history for various uses in traditional medicine and as a source of food. As part of ongoing research to explore the chemical diversity and biologically active compounds from natural resources, two new coumaric acid-aliphatic alcohol hybrids, ginkwanghols A (1) and B (2) were isolated from the leaves of G. biloba. The coumaric acid-aliphatic alcohol hybrids of natural products have rarely been reported. The structures of the new compounds were determined by extensive NMR spectroscopic analysis, HRESI-MS, and quantum chemical ECD calculations, and by comparing the experimental HRESI-MS/MS spectrum of chemically transformed compound 1a with the predicted HRESI-MS/MS spectra proposed from CFM-ID 3.0, a software tool for MS/MS spectral prediction and MS-based compound identification. Ginkwanghols A (1) and B (2) increased alkaline phosphatase (ALP) production in C3H10T1/2, a mouse mesenchymal stem cell line, in a dose-dependent manner. In addition, ginkwanghols A and B mediated the promotion of osteogenic differentiation as indicated by the induction of the mRNA expression of the osteogenic markers ALP and osteopontin (OPN).

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Acknowledgements

This work was supported by a National Research Foundation of Korea (NRF) Grant funded by the Korean government (2019R1A5A2027340 and 2021R1A2C2007937) and the Korea Institute of Science and Technology intramural research Grant (2E30641). This work was also supported by the Nano Convergence Industrial Strategic Technology Development Program (20000105, Development of Cosmeceutical Material Platform using Organo-Nano Complexes based on Natural Active Compounds) funded by the Ministry of Trade, Industry & Energy (MOTIE, Korea).

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Correspondence to Ki Hyun Kim.

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Lee, K.H., Kim, J.K., Yu, J.S. et al. Ginkwanghols A and B, osteogenic coumaric acid-aliphatic alcohol hybrids from the leaves of Ginkgo biloba. Arch. Pharm. Res. 44, 514–524 (2021). https://doi.org/10.1007/s12272-021-01329-3

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  • DOI: https://doi.org/10.1007/s12272-021-01329-3

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