Preliminary Quality Evaluation and Characterization of Phenolic Constituents in Cynanchi Wilfordii Radix
A new phenolic compound, 2-O-β-laminaribiosyl-4-hydroxyacetophenone (1), was isolated from Cynanchi Wilfordii Radix (CWR, the root of Cynanchum wilfordii Hemsley), along with 10 known aromatic compounds, including cynandione A (2), bungeisides-C (7) and –D (8), p-hydroxyacetophenone (9), 2′,5′-dihyd...
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MDPI AG
2018-03-01
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| Series: | Molecules |
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| Online Access: | http://www.mdpi.com/1420-3049/23/3/656 |
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| author | Takashi Uchikura Hiroaki Tanaka Hidemi Sugiwaki Morio Yoshimura Naoko Sato-Masumoto Takashi Tsujimoto Nahoko Uchiyama Takashi Hakamatsuka Yoshiaki Amakura |
| author_facet | Takashi Uchikura Hiroaki Tanaka Hidemi Sugiwaki Morio Yoshimura Naoko Sato-Masumoto Takashi Tsujimoto Nahoko Uchiyama Takashi Hakamatsuka Yoshiaki Amakura |
| author_sort | Takashi Uchikura |
| collection | DOAJ |
| description | A new phenolic compound, 2-O-β-laminaribiosyl-4-hydroxyacetophenone (1), was isolated from Cynanchi Wilfordii Radix (CWR, the root of Cynanchum wilfordii Hemsley), along with 10 known aromatic compounds, including cynandione A (2), bungeisides-C (7) and –D (8), p-hydroxyacetophenone (9), 2′,5′-dihydroxyacetophenone (10), and 2′,4′-dihydroxyacetophenone (11). The structure of the new compound (1) was elucidated using spectroscopic methods and chemical methods. The structure of cynandione A (2), including a linkage mode of the biphenyl parts that remained uncertain, was unambiguously confirmed using the 2D 13C–13C incredible natural abundance double quantum transfer experiment (INADEQUATE) spectrum. Additionally, health issues related to the use of Cynanchi Auriculati Radix (CAR, the root of Cynanchum auriculatum Royle ex Wight) instead of CWR have emerged. Therefore, constituents present in methanolic extracts of commercially available CWRs and CARs were examined using UV-sensitive high-performance liquid chromatography (HPLC), resulting in common detection of three major peaks ascribed to cynandione A (2), p-hydroxyacetophenone (9), and 2′,4′-dihydroxyacetophenone (11). Thus, to distinguish between these ingredients, a thin-layer chromatography (TLC) method, combined with only UV irradiation detection, focusing on wilfosides C1N (12) and K1N (13) as marker compounds characteristic of CAR, was performed. Furthermore, we propose this method as a simple and convenient strategy for the preliminary distinction of CWR and CAR to ensure the quality and safety of their crude drugs. |
| first_indexed | 2024-12-12T05:55:21Z |
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| issn | 1420-3049 |
| language | English |
| last_indexed | 2024-12-12T05:55:21Z |
| publishDate | 2018-03-01 |
| publisher | MDPI AG |
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| series | Molecules |
| spelling | doaj.art-c25d70446a164130bd3b42078fc7d4992022-12-22T00:35:34ZengMDPI AGMolecules1420-30492018-03-0123365610.3390/molecules23030656molecules23030656Preliminary Quality Evaluation and Characterization of Phenolic Constituents in Cynanchi Wilfordii RadixTakashi Uchikura0Hiroaki Tanaka1Hidemi Sugiwaki2Morio Yoshimura3Naoko Sato-Masumoto4Takashi Tsujimoto5Nahoko Uchiyama6Takashi Hakamatsuka7Yoshiaki Amakura8Department of Pharmacognosy, College of Pharmaceutical Sciences, Matsuyama University, 4-2 Bunkyo-cho, Matsuyama, Ehime 790-8578, JapanDepartment of Pharmacognosy, College of Pharmaceutical Sciences, Matsuyama University, 4-2 Bunkyo-cho, Matsuyama, Ehime 790-8578, JapanDepartment of Pharmacognosy, College of Pharmaceutical Sciences, Matsuyama University, 4-2 Bunkyo-cho, Matsuyama, Ehime 790-8578, JapanDepartment of Pharmacognosy, College of Pharmaceutical Sciences, Matsuyama University, 4-2 Bunkyo-cho, Matsuyama, Ehime 790-8578, JapanDivision of Pharmacognosy, Phytochemistry and Narcotics, National Institute of Health Sciences, 3-25-26 Tonomachi, Kawasaki-ku, Kawasaki, Kanagawa 210-9501, JapanDivision of Pharmacognosy, Phytochemistry and Narcotics, National Institute of Health Sciences, 3-25-26 Tonomachi, Kawasaki-ku, Kawasaki, Kanagawa 210-9501, JapanDivision of Pharmacognosy, Phytochemistry and Narcotics, National Institute of Health Sciences, 3-25-26 Tonomachi, Kawasaki-ku, Kawasaki, Kanagawa 210-9501, JapanDivision of Pharmacognosy, Phytochemistry and Narcotics, National Institute of Health Sciences, 3-25-26 Tonomachi, Kawasaki-ku, Kawasaki, Kanagawa 210-9501, JapanDepartment of Pharmacognosy, College of Pharmaceutical Sciences, Matsuyama University, 4-2 Bunkyo-cho, Matsuyama, Ehime 790-8578, JapanA new phenolic compound, 2-O-β-laminaribiosyl-4-hydroxyacetophenone (1), was isolated from Cynanchi Wilfordii Radix (CWR, the root of Cynanchum wilfordii Hemsley), along with 10 known aromatic compounds, including cynandione A (2), bungeisides-C (7) and –D (8), p-hydroxyacetophenone (9), 2′,5′-dihydroxyacetophenone (10), and 2′,4′-dihydroxyacetophenone (11). The structure of the new compound (1) was elucidated using spectroscopic methods and chemical methods. The structure of cynandione A (2), including a linkage mode of the biphenyl parts that remained uncertain, was unambiguously confirmed using the 2D 13C–13C incredible natural abundance double quantum transfer experiment (INADEQUATE) spectrum. Additionally, health issues related to the use of Cynanchi Auriculati Radix (CAR, the root of Cynanchum auriculatum Royle ex Wight) instead of CWR have emerged. Therefore, constituents present in methanolic extracts of commercially available CWRs and CARs were examined using UV-sensitive high-performance liquid chromatography (HPLC), resulting in common detection of three major peaks ascribed to cynandione A (2), p-hydroxyacetophenone (9), and 2′,4′-dihydroxyacetophenone (11). Thus, to distinguish between these ingredients, a thin-layer chromatography (TLC) method, combined with only UV irradiation detection, focusing on wilfosides C1N (12) and K1N (13) as marker compounds characteristic of CAR, was performed. Furthermore, we propose this method as a simple and convenient strategy for the preliminary distinction of CWR and CAR to ensure the quality and safety of their crude drugs.http://www.mdpi.com/1420-3049/23/3/656Cynanchum wilfordiiphenolic glycoside2-O-β-laminaribiosyl-4-hydroxyacetophenonecynandione Athin layer chromatographyCynanchum auriculatum |
| spellingShingle | Takashi Uchikura Hiroaki Tanaka Hidemi Sugiwaki Morio Yoshimura Naoko Sato-Masumoto Takashi Tsujimoto Nahoko Uchiyama Takashi Hakamatsuka Yoshiaki Amakura Preliminary Quality Evaluation and Characterization of Phenolic Constituents in Cynanchi Wilfordii Radix Molecules Cynanchum wilfordii phenolic glycoside 2-O-β-laminaribiosyl-4-hydroxyacetophenone cynandione A thin layer chromatography Cynanchum auriculatum |
| title | Preliminary Quality Evaluation and Characterization of Phenolic Constituents in Cynanchi Wilfordii Radix |
| title_full | Preliminary Quality Evaluation and Characterization of Phenolic Constituents in Cynanchi Wilfordii Radix |
| title_fullStr | Preliminary Quality Evaluation and Characterization of Phenolic Constituents in Cynanchi Wilfordii Radix |
| title_full_unstemmed | Preliminary Quality Evaluation and Characterization of Phenolic Constituents in Cynanchi Wilfordii Radix |
| title_short | Preliminary Quality Evaluation and Characterization of Phenolic Constituents in Cynanchi Wilfordii Radix |
| title_sort | preliminary quality evaluation and characterization of phenolic constituents in cynanchi wilfordii radix |
| topic | Cynanchum wilfordii phenolic glycoside 2-O-β-laminaribiosyl-4-hydroxyacetophenone cynandione A thin layer chromatography Cynanchum auriculatum |
| url | http://www.mdpi.com/1420-3049/23/3/656 |
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