A-Type Proanthocyanidins from the Stems of Ephedra sinica (Ephedraceae) and Their Antimicrobial Activities
Phytochemical investigation of the n-BuOH-soluble fraction of the EtOH extract of the herbaceous stems of Ephedra sinica, which is known as Ephedrae Herba in Traditional Chinese Medicine, led to the isolation and identification of 12 A-type proanthocyanidins, containing five dimers, two trimers and...
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MDPI AG
2013-05-01
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| Series: | Molecules |
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| Online Access: | http://www.mdpi.com/1420-3049/18/5/5172 |
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| author | Xinyu Zang Mingying Shang Feng Xu Jing Liang Xuan Wang Masayuki Mikage Shaoqing Cai |
| author_facet | Xinyu Zang Mingying Shang Feng Xu Jing Liang Xuan Wang Masayuki Mikage Shaoqing Cai |
| author_sort | Xinyu Zang |
| collection | DOAJ |
| description | Phytochemical investigation of the n-BuOH-soluble fraction of the EtOH extract of the herbaceous stems of Ephedra sinica, which is known as Ephedrae Herba in Traditional Chinese Medicine, led to the isolation and identification of 12 A-type proanthocyanidins, containing five dimers, two trimers and five tetramers [i.e., (+)-epigallocatechin-(2α→O→7,4α→8)-(-)-catechin, named ephedrannin D1, a dimer; epigallocatechin-(2α→O→7,4α→8)-epigallocatechin-(4α→8)-catechin (ephedrannin Tr1), a trimer; and epigallocatechin-(2α→O→7,4α→8)-epigallocatechin-(4α→8)-epigallocatechin-(2α→O→7,4α→8)-gallocatechin, named ephedrannin Te1, a tetramer). Tetramers composed of gallocatechin are reported for the first time in Ephedraceae. Catechin, epicatechin, gallocatechin, epigallocatechin and four known dimers were also isolated. The structures were elucidated by extensive spectroscopic analysis. The absolute configurations of the 4α linkages, which were confirmed by NOESY and CD experiments, are the outstanding characteristic of most of these isolated A-type proanthocyanidins. The antimicrobial activities of these compounds were tested by measuring the minimum inhibitory concentrations (MIC) against bacteria (both Gram positive and Gram negative) and fungi, and were found to be in the range of 0.00515–1.38 mM. Compounds 6, 8, 10 and 11 exhibited moderate antimicrobial activities against Canidia albicans. |
| first_indexed | 2024-12-12T02:49:02Z |
| format | Article |
| id | doaj.art-9dd48717f5254946919327b6bbf851d3 |
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| issn | 1420-3049 |
| language | English |
| last_indexed | 2024-12-12T02:49:02Z |
| publishDate | 2013-05-01 |
| publisher | MDPI AG |
| record_format | Article |
| series | Molecules |
| spelling | doaj.art-9dd48717f5254946919327b6bbf851d32022-12-22T00:40:57ZengMDPI AGMolecules1420-30492013-05-011855172518910.3390/molecules18055172A-Type Proanthocyanidins from the Stems of Ephedra sinica (Ephedraceae) and Their Antimicrobial ActivitiesXinyu ZangMingying ShangFeng XuJing LiangXuan WangMasayuki MikageShaoqing CaiPhytochemical investigation of the n-BuOH-soluble fraction of the EtOH extract of the herbaceous stems of Ephedra sinica, which is known as Ephedrae Herba in Traditional Chinese Medicine, led to the isolation and identification of 12 A-type proanthocyanidins, containing five dimers, two trimers and five tetramers [i.e., (+)-epigallocatechin-(2α→O→7,4α→8)-(-)-catechin, named ephedrannin D1, a dimer; epigallocatechin-(2α→O→7,4α→8)-epigallocatechin-(4α→8)-catechin (ephedrannin Tr1), a trimer; and epigallocatechin-(2α→O→7,4α→8)-epigallocatechin-(4α→8)-epigallocatechin-(2α→O→7,4α→8)-gallocatechin, named ephedrannin Te1, a tetramer). Tetramers composed of gallocatechin are reported for the first time in Ephedraceae. Catechin, epicatechin, gallocatechin, epigallocatechin and four known dimers were also isolated. The structures were elucidated by extensive spectroscopic analysis. The absolute configurations of the 4α linkages, which were confirmed by NOESY and CD experiments, are the outstanding characteristic of most of these isolated A-type proanthocyanidins. The antimicrobial activities of these compounds were tested by measuring the minimum inhibitory concentrations (MIC) against bacteria (both Gram positive and Gram negative) and fungi, and were found to be in the range of 0.00515–1.38 mM. Compounds 6, 8, 10 and 11 exhibited moderate antimicrobial activities against Canidia albicans.http://www.mdpi.com/1420-3049/18/5/5172Ephedra sinicaEphedraceaeA-type proanthocyanidinephedrannin D1ephedrannin Tr1ephedrannin Te1antimicrobial activities |
| spellingShingle | Xinyu Zang Mingying Shang Feng Xu Jing Liang Xuan Wang Masayuki Mikage Shaoqing Cai A-Type Proanthocyanidins from the Stems of Ephedra sinica (Ephedraceae) and Their Antimicrobial Activities Molecules Ephedra sinica Ephedraceae A-type proanthocyanidin ephedrannin D1 ephedrannin Tr1 ephedrannin Te1 antimicrobial activities |
| title | A-Type Proanthocyanidins from the Stems of Ephedra sinica (Ephedraceae) and Their Antimicrobial Activities |
| title_full | A-Type Proanthocyanidins from the Stems of Ephedra sinica (Ephedraceae) and Their Antimicrobial Activities |
| title_fullStr | A-Type Proanthocyanidins from the Stems of Ephedra sinica (Ephedraceae) and Their Antimicrobial Activities |
| title_full_unstemmed | A-Type Proanthocyanidins from the Stems of Ephedra sinica (Ephedraceae) and Their Antimicrobial Activities |
| title_short | A-Type Proanthocyanidins from the Stems of Ephedra sinica (Ephedraceae) and Their Antimicrobial Activities |
| title_sort | a type proanthocyanidins from the stems of ephedra sinica ephedraceae and their antimicrobial activities |
| topic | Ephedra sinica Ephedraceae A-type proanthocyanidin ephedrannin D1 ephedrannin Tr1 ephedrannin Te1 antimicrobial activities |
| url | http://www.mdpi.com/1420-3049/18/5/5172 |
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