A specialized flavone biosynthetic pathway has evolved in the medicinal plant, Scutellaria baicalensis
Wogonin and baicalein are bioactive flavones in the popular Chinese herbal remedy Huang-Qin (Scutellaria baicalensis Georgi). These specialized flavones lack a 4′-hydroxyl group on the B ring (4′-deoxyflavones) and induce apoptosis in a wide spectrum of human tumor cells in vitro and inhibit tumor g...
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| Format: | Article |
| Language: | en_US |
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American Association for the Advancement of Science (AAAS)
2016
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| Online Access: | http://hdl.handle.net/1721.1/105844 |
| _version_ | 1826214724006576128 |
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| author | Zhao, Q. Zhang, Y. Wang, G. Hill, L. Chen, X.-Y. Xue, H. Martin, C. Weng, Jing-Ke |
| author2 | Massachusetts Institute of Technology. Department of Biology |
| author_facet | Massachusetts Institute of Technology. Department of Biology Zhao, Q. Zhang, Y. Wang, G. Hill, L. Chen, X.-Y. Xue, H. Martin, C. Weng, Jing-Ke |
| author_sort | Zhao, Q. |
| collection | MIT |
| description | Wogonin and baicalein are bioactive flavones in the popular Chinese herbal remedy Huang-Qin (Scutellaria baicalensis Georgi). These specialized flavones lack a 4′-hydroxyl group on the B ring (4′-deoxyflavones) and induce apoptosis in a wide spectrum of human tumor cells in vitro and inhibit tumor growth in vivo in different mouse tumor models. Root-specific flavones (RSFs) from Scutellaria have a variety of reported additional beneficial effects including antioxidant and antiviral properties. We describe the characterization of a new pathway for the synthesis of these compounds, in which pinocembrin (a 4′-deoxyflavanone) serves as a key intermediate. Although two genes encoding flavone synthase II (FNSII) are expressed in the roots of S. baicalensis, FNSII-1 has broad specificity for flavanones as substrates, whereas FNSII-2 is specific for pinocembrin. FNSII-2 is responsible for the synthesis of 4′-deoxyRSFs, such as chrysin and wogonin, wogonoside, baicalein, and baicalin, which are synthesized from chrysin. A gene encoding a cinnamic acid–specific coenzyme A ligase (SbCLL-7), which is highly expressed in roots, is required for the synthesis of RSFs by FNSII-2, as demonstrated by gene silencing. A specific isoform of chalcone synthase (SbCHS-2) that is highly expressed in roots producing RSFs is also required for the synthesis of chrysin. Our studies reveal a recently evolved pathway for biosynthesis of specific, bioactive 4′-deoxyflavones in the roots of S. baicalensis. |
| first_indexed | 2024-09-23T16:10:27Z |
| format | Article |
| id | mit-1721.1/105844 |
| institution | Massachusetts Institute of Technology |
| language | en_US |
| last_indexed | 2024-09-23T16:10:27Z |
| publishDate | 2016 |
| publisher | American Association for the Advancement of Science (AAAS) |
| record_format | dspace |
| spelling | mit-1721.1/1058442022-10-02T06:51:00Z A specialized flavone biosynthetic pathway has evolved in the medicinal plant, Scutellaria baicalensis Zhao, Q. Zhang, Y. Wang, G. Hill, L. Chen, X.-Y. Xue, H. Martin, C. Weng, Jing-Ke Massachusetts Institute of Technology. Department of Biology Whitehead Institute for Biomedical Research Weng, Jing-Ke Wogonin and baicalein are bioactive flavones in the popular Chinese herbal remedy Huang-Qin (Scutellaria baicalensis Georgi). These specialized flavones lack a 4′-hydroxyl group on the B ring (4′-deoxyflavones) and induce apoptosis in a wide spectrum of human tumor cells in vitro and inhibit tumor growth in vivo in different mouse tumor models. Root-specific flavones (RSFs) from Scutellaria have a variety of reported additional beneficial effects including antioxidant and antiviral properties. We describe the characterization of a new pathway for the synthesis of these compounds, in which pinocembrin (a 4′-deoxyflavanone) serves as a key intermediate. Although two genes encoding flavone synthase II (FNSII) are expressed in the roots of S. baicalensis, FNSII-1 has broad specificity for flavanones as substrates, whereas FNSII-2 is specific for pinocembrin. FNSII-2 is responsible for the synthesis of 4′-deoxyRSFs, such as chrysin and wogonin, wogonoside, baicalein, and baicalin, which are synthesized from chrysin. A gene encoding a cinnamic acid–specific coenzyme A ligase (SbCLL-7), which is highly expressed in roots, is required for the synthesis of RSFs by FNSII-2, as demonstrated by gene silencing. A specific isoform of chalcone synthase (SbCHS-2) that is highly expressed in roots producing RSFs is also required for the synthesis of chrysin. Our studies reveal a recently evolved pathway for biosynthesis of specific, bioactive 4′-deoxyflavones in the roots of S. baicalensis. 2016-12-15T21:49:25Z 2016-12-15T21:49:25Z 2016-05 2015-12 Article http://purl.org/eprint/type/JournalArticle 2375-2548 http://hdl.handle.net/1721.1/105844 Zhao, Q. et al. “A Specialized Flavone Biosynthetic Pathway Has Evolved in the Medicinal Plant, Scutellaria Baicalensis.” Science Advances 2.4 (2016): e1501780–e1501780. en_US http://dx.doi.org/10.1126/sciadv.1501780 Science Advances Creative Commons Attribution-NonCommercial 4.0 International http://creativecommons.org/licenses/by-nc/4.0/ application/pdf American Association for the Advancement of Science (AAAS) Science |
| spellingShingle | Zhao, Q. Zhang, Y. Wang, G. Hill, L. Chen, X.-Y. Xue, H. Martin, C. Weng, Jing-Ke A specialized flavone biosynthetic pathway has evolved in the medicinal plant, Scutellaria baicalensis |
| title | A specialized flavone biosynthetic pathway has evolved in the medicinal plant, Scutellaria baicalensis |
| title_full | A specialized flavone biosynthetic pathway has evolved in the medicinal plant, Scutellaria baicalensis |
| title_fullStr | A specialized flavone biosynthetic pathway has evolved in the medicinal plant, Scutellaria baicalensis |
| title_full_unstemmed | A specialized flavone biosynthetic pathway has evolved in the medicinal plant, Scutellaria baicalensis |
| title_short | A specialized flavone biosynthetic pathway has evolved in the medicinal plant, Scutellaria baicalensis |
| title_sort | specialized flavone biosynthetic pathway has evolved in the medicinal plant scutellaria baicalensis |
| url | http://hdl.handle.net/1721.1/105844 |
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