Ellagitannins and Oligomeric Proanthocyanidins of Three Polygonaceous Plants
The aim of this study was to characterize hydrolyzable tannins in Polygonaceous plants, as only a few plants have previously been reported to contain ellagitannins. From <i>Persicaria chinensis</i>, a new hydrolyzable tannin called persicarianin was isolated and characterized to be 3-<...
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| Format: | Article |
| Language: | English |
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MDPI AG
2021-01-01
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| Series: | Molecules |
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| Online Access: | https://www.mdpi.com/1420-3049/26/2/337 |
| _version_ | 1797413148468183040 |
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| author | Yun-Qiu Li Masako Kitaoka Juri Takayoshi Ya-Feng Wang Yosuke Matsuo Yoshinori Saito Yong-Lin Huang Dian-Peng Li Gen-ichiro Nonaka Zhi-Hong Jiang Takashi Tanaka |
| author_facet | Yun-Qiu Li Masako Kitaoka Juri Takayoshi Ya-Feng Wang Yosuke Matsuo Yoshinori Saito Yong-Lin Huang Dian-Peng Li Gen-ichiro Nonaka Zhi-Hong Jiang Takashi Tanaka |
| author_sort | Yun-Qiu Li |
| collection | DOAJ |
| description | The aim of this study was to characterize hydrolyzable tannins in Polygonaceous plants, as only a few plants have previously been reported to contain ellagitannins. From <i>Persicaria chinensis</i>, a new hydrolyzable tannin called persicarianin was isolated and characterized to be 3-<i>O</i>-galloyl-4,6-(<i>S</i>)-dehydrohexahydroxydiphenoyl-<span style="font-variant: small-caps;">d</span>-glucose. Interestingly, acid hydrolysis of this compound afforded ellagic acid, despite the absence of a hexahydroxydiphenoyl group. From the rhizome of <i>Polygonum runcinatum</i> var. <i>sinense</i>, a large amount of granatin A, along with minor ellagitannins, helioscpoinin A, davicratinic acids B and C, and a new ellagitannin called polygonanin A, were isolated. Based on 2D nuclear magnetic resonance (NMR) spectroscopic examination, the structure of polygonanin A was determined to be 1,6-(<i>S</i>)-hexahydroxydiphenoyl-2,4-hydroxychebuloyl-β-<span style="font-variant: small-caps;">d</span>-glucopyranose. These are the second and third hydrolyzable tannins isolated from Polygonaceous plants. In addition, oligomeric proanthocyanidins of <i>Persicaria capitatum</i> and <i>P. chinensis</i> were characterized by thiol degradation. These results suggested that some Polygonaceous plants are the source of hydrolyzable tannins not only proanthocyanidins. |
| first_indexed | 2024-03-09T05:13:26Z |
| format | Article |
| id | doaj.art-cbc61238e2d94f42ad3b127c1ba1d871 |
| institution | Directory Open Access Journal |
| issn | 1420-3049 |
| language | English |
| last_indexed | 2024-03-09T05:13:26Z |
| publishDate | 2021-01-01 |
| publisher | MDPI AG |
| record_format | Article |
| series | Molecules |
| spelling | doaj.art-cbc61238e2d94f42ad3b127c1ba1d8712023-12-03T12:47:12ZengMDPI AGMolecules1420-30492021-01-0126233710.3390/molecules26020337Ellagitannins and Oligomeric Proanthocyanidins of Three Polygonaceous PlantsYun-Qiu Li0Masako Kitaoka1Juri Takayoshi2Ya-Feng Wang3Yosuke Matsuo4Yoshinori Saito5Yong-Lin Huang6Dian-Peng Li7Gen-ichiro Nonaka8Zhi-Hong Jiang9Takashi Tanaka10Department of Natural Product Chemistry, Graduate School of Biomedical Sciences, Nagasaki University, 1-14 Bunkyo-machi, Nagasaki 852-8521, JapanDepartment of Natural Product Chemistry, School of Pharmaceutical Sciences, Nagasaki University, 1-14 Bunkyo-machi, Nagasaki 852-8521, JapanDepartment of Natural Product Chemistry, School of Pharmaceutical Sciences, Nagasaki University, 1-14 Bunkyo-machi, Nagasaki 852-8521, JapanGuangxi Key Laboratory of Functional Phytochemicals Research and Utilization, Guangxi Institute of Botany, Guilin 541006, ChinaDepartment of Natural Product Chemistry, Graduate School of Biomedical Sciences, Nagasaki University, 1-14 Bunkyo-machi, Nagasaki 852-8521, JapanDepartment of Natural Product Chemistry, Graduate School of Biomedical Sciences, Nagasaki University, 1-14 Bunkyo-machi, Nagasaki 852-8521, JapanGuangxi Key Laboratory of Functional Phytochemicals Research and Utilization, Guangxi Institute of Botany, Guilin 541006, ChinaGuangxi Key Laboratory of Functional Phytochemicals Research and Utilization, Guangxi Institute of Botany, Guilin 541006, ChinaUsaien Pharmaceutical Company, Ltd., 1-4-6 Zaimoku, Saga 840-0055, JapanInstitute for Applied Research in Medicine and Health, Macau University of Science and Technology, Taipa, Macau 999078, ChinaDepartment of Natural Product Chemistry, Graduate School of Biomedical Sciences, Nagasaki University, 1-14 Bunkyo-machi, Nagasaki 852-8521, JapanThe aim of this study was to characterize hydrolyzable tannins in Polygonaceous plants, as only a few plants have previously been reported to contain ellagitannins. From <i>Persicaria chinensis</i>, a new hydrolyzable tannin called persicarianin was isolated and characterized to be 3-<i>O</i>-galloyl-4,6-(<i>S</i>)-dehydrohexahydroxydiphenoyl-<span style="font-variant: small-caps;">d</span>-glucose. Interestingly, acid hydrolysis of this compound afforded ellagic acid, despite the absence of a hexahydroxydiphenoyl group. From the rhizome of <i>Polygonum runcinatum</i> var. <i>sinense</i>, a large amount of granatin A, along with minor ellagitannins, helioscpoinin A, davicratinic acids B and C, and a new ellagitannin called polygonanin A, were isolated. Based on 2D nuclear magnetic resonance (NMR) spectroscopic examination, the structure of polygonanin A was determined to be 1,6-(<i>S</i>)-hexahydroxydiphenoyl-2,4-hydroxychebuloyl-β-<span style="font-variant: small-caps;">d</span>-glucopyranose. These are the second and third hydrolyzable tannins isolated from Polygonaceous plants. In addition, oligomeric proanthocyanidins of <i>Persicaria capitatum</i> and <i>P. chinensis</i> were characterized by thiol degradation. These results suggested that some Polygonaceous plants are the source of hydrolyzable tannins not only proanthocyanidins.https://www.mdpi.com/1420-3049/26/2/337ellagitanninhydrolyzable tanninproanthocyanidinPersicariaPolygonumPolygonaceae |
| spellingShingle | Yun-Qiu Li Masako Kitaoka Juri Takayoshi Ya-Feng Wang Yosuke Matsuo Yoshinori Saito Yong-Lin Huang Dian-Peng Li Gen-ichiro Nonaka Zhi-Hong Jiang Takashi Tanaka Ellagitannins and Oligomeric Proanthocyanidins of Three Polygonaceous Plants Molecules ellagitannin hydrolyzable tannin proanthocyanidin Persicaria Polygonum Polygonaceae |
| title | Ellagitannins and Oligomeric Proanthocyanidins of Three Polygonaceous Plants |
| title_full | Ellagitannins and Oligomeric Proanthocyanidins of Three Polygonaceous Plants |
| title_fullStr | Ellagitannins and Oligomeric Proanthocyanidins of Three Polygonaceous Plants |
| title_full_unstemmed | Ellagitannins and Oligomeric Proanthocyanidins of Three Polygonaceous Plants |
| title_short | Ellagitannins and Oligomeric Proanthocyanidins of Three Polygonaceous Plants |
| title_sort | ellagitannins and oligomeric proanthocyanidins of three polygonaceous plants |
| topic | ellagitannin hydrolyzable tannin proanthocyanidin Persicaria Polygonum Polygonaceae |
| url | https://www.mdpi.com/1420-3049/26/2/337 |
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