New metabolites from the biotransformation of ginsenoside Rb1 by Paecilomyces bainier sp.229 and activities in inducing osteogenic differentiation by Wnt/β-catenin signaling activation
Background: Ginseng is a well-known traditional Chinese medicine that has been widely used in a range of therapeutic and healthcare applications in East Asian countries. Microbial transformation is regarded as an effective and useful technology in modification of nature products for finding new chem...
| Main Authors: | , , , , |
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| Format: | Article |
| Language: | English |
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Elsevier
2018-04-01
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| Series: | Journal of Ginseng Research |
| Online Access: | http://www.sciencedirect.com/science/article/pii/S1226845316302937 |
| _version_ | 1828378715566899200 |
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| author | Wei Zhou Hai Huang Haiyan Zhu Pei Zhou Xunlong Shi |
| author_facet | Wei Zhou Hai Huang Haiyan Zhu Pei Zhou Xunlong Shi |
| author_sort | Wei Zhou |
| collection | DOAJ |
| description | Background: Ginseng is a well-known traditional Chinese medicine that has been widely used in a range of therapeutic and healthcare applications in East Asian countries. Microbial transformation is regarded as an effective and useful technology in modification of nature products for finding new chemical derivatives with potent bioactivities. In this study, three minor derivatives of ginsenoside compound K were isolated and the inducing effects in the Wingless-type MMTV integration site (Wnt) signaling pathway were also investigated. Methods: New compounds were purified from scale-up fermentation of ginsenoside Rb1 by Paecilomyces bainier sp. 229 through repeated silica gel column chromatography and high pressure liquid chromatography. Their structures were determined based on spectral data and X-ray diffraction. The inductive activities of these compounds on the Wnt signaling pathway were conducted on MC3T3-E1 cells by quantitative real-time polymerase chain reaction analysis. Results: The structures of a known 3-keto derivative and two new dehydrogenated metabolites were elucidated. The crystal structure of the 3-keto derivative was reported for the first time and its conformation was compared with that of ginsenoside compound K. The inductive effects of these compounds on osteogenic differentiation by activating the Wnt/β-catenin signaling pathway were explained for the first time. Conclusion: This study may provide a new insight into the metabolic pathway of ginsenoside by microbial transformation. In addition, the results might provide a reasonable explanation for the activity of ginseng in treating osteoporosis and supply good monomer ginsenoside resources for nutraceutical or pharmaceutical development. Keywords: biotransformation, ginsenoside, osteogenic differentiation, Wnt/β-catenin signal |
| first_indexed | 2024-04-14T08:30:57Z |
| format | Article |
| id | doaj.art-4120a77ce94c48b1adb03445973b6ed2 |
| institution | Directory Open Access Journal |
| issn | 1226-8453 |
| language | English |
| last_indexed | 2024-04-14T08:30:57Z |
| publishDate | 2018-04-01 |
| publisher | Elsevier |
| record_format | Article |
| series | Journal of Ginseng Research |
| spelling | doaj.art-4120a77ce94c48b1adb03445973b6ed22022-12-22T02:03:55ZengElsevierJournal of Ginseng Research1226-84532018-04-01422199207New metabolites from the biotransformation of ginsenoside Rb1 by Paecilomyces bainier sp.229 and activities in inducing osteogenic differentiation by Wnt/β-catenin signaling activationWei Zhou0Hai Huang1Haiyan Zhu2Pei Zhou3Xunlong Shi4Department of Chemistry, Fudan University, Shanghai, ChinaSchool of Pharmacy, Fudan University, Shanghai, ChinaSchool of Pharmacy, Fudan University, Shanghai, ChinaSchool of Pharmacy, Fudan University, Shanghai, ChinaSchool of Pharmacy, Fudan University, Shanghai, China; Corresponding author. School of Pharmacy, Fudan University, 826 Zhangheng Road, Zhangjiang Hi-Tech Park, Shanghai 201203, China.Background: Ginseng is a well-known traditional Chinese medicine that has been widely used in a range of therapeutic and healthcare applications in East Asian countries. Microbial transformation is regarded as an effective and useful technology in modification of nature products for finding new chemical derivatives with potent bioactivities. In this study, three minor derivatives of ginsenoside compound K were isolated and the inducing effects in the Wingless-type MMTV integration site (Wnt) signaling pathway were also investigated. Methods: New compounds were purified from scale-up fermentation of ginsenoside Rb1 by Paecilomyces bainier sp. 229 through repeated silica gel column chromatography and high pressure liquid chromatography. Their structures were determined based on spectral data and X-ray diffraction. The inductive activities of these compounds on the Wnt signaling pathway were conducted on MC3T3-E1 cells by quantitative real-time polymerase chain reaction analysis. Results: The structures of a known 3-keto derivative and two new dehydrogenated metabolites were elucidated. The crystal structure of the 3-keto derivative was reported for the first time and its conformation was compared with that of ginsenoside compound K. The inductive effects of these compounds on osteogenic differentiation by activating the Wnt/β-catenin signaling pathway were explained for the first time. Conclusion: This study may provide a new insight into the metabolic pathway of ginsenoside by microbial transformation. In addition, the results might provide a reasonable explanation for the activity of ginseng in treating osteoporosis and supply good monomer ginsenoside resources for nutraceutical or pharmaceutical development. Keywords: biotransformation, ginsenoside, osteogenic differentiation, Wnt/β-catenin signalhttp://www.sciencedirect.com/science/article/pii/S1226845316302937 |
| spellingShingle | Wei Zhou Hai Huang Haiyan Zhu Pei Zhou Xunlong Shi New metabolites from the biotransformation of ginsenoside Rb1 by Paecilomyces bainier sp.229 and activities in inducing osteogenic differentiation by Wnt/β-catenin signaling activation Journal of Ginseng Research |
| title | New metabolites from the biotransformation of ginsenoside Rb1 by Paecilomyces bainier sp.229 and activities in inducing osteogenic differentiation by Wnt/β-catenin signaling activation |
| title_full | New metabolites from the biotransformation of ginsenoside Rb1 by Paecilomyces bainier sp.229 and activities in inducing osteogenic differentiation by Wnt/β-catenin signaling activation |
| title_fullStr | New metabolites from the biotransformation of ginsenoside Rb1 by Paecilomyces bainier sp.229 and activities in inducing osteogenic differentiation by Wnt/β-catenin signaling activation |
| title_full_unstemmed | New metabolites from the biotransformation of ginsenoside Rb1 by Paecilomyces bainier sp.229 and activities in inducing osteogenic differentiation by Wnt/β-catenin signaling activation |
| title_short | New metabolites from the biotransformation of ginsenoside Rb1 by Paecilomyces bainier sp.229 and activities in inducing osteogenic differentiation by Wnt/β-catenin signaling activation |
| title_sort | new metabolites from the biotransformation of ginsenoside rb1 by paecilomyces bainier sp 229 and activities in inducing osteogenic differentiation by wnt β catenin signaling activation |
| url | http://www.sciencedirect.com/science/article/pii/S1226845316302937 |
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