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KMID : 0043320210440050514
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Archives of Pharmacal Research
2021 Volume.44 No. 5 p.514 ~ p.524
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Ginkwanghols A and B, osteogenic coumaric acid-aliphatic alcohol hybrids from the leaves of Ginkgo biloba
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Lee Kwang-Ho
Kim Jung-Kyu
Yu Jae-Sik
Jeong Se-Yun
Choi Jin-Hee
Kim Jin-Chul
Ko Yoon-Joo
Kim Seon-Hee
Kim Ki-Hyun
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Abstract
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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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KEYWORD
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Ginkgo biloba, MS/MS, CFM-ID 3.0, ECD calculations, Alkaline phosphatase
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