Ellagitannin Oligomers from <i>Eucalyptus camaldulensis</i> Leaves and Their Role in the Detoxification of Aluminum
<i>Eucalyptus camaldulensis</i> of the Myrtaceae family shows high resistance to aluminum (Al) ions and contains various compounds such as steroids, terpenoids, saponins, flavonoids, glycosides, alkaloids, and tannins. Although the ellagitannin oenothein B (<b>12</b>) isolate...
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2025-05-01
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| author | Haruna Uemori Ayano Inoue Shoichi Suzuki Yuji Iwaoka Tsutomu Hatano Morio Yoshimura Yoshiaki Amakura Toshiyuki Murakami Ko Tahara Hideyuki Ito |
| author_facet | Haruna Uemori Ayano Inoue Shoichi Suzuki Yuji Iwaoka Tsutomu Hatano Morio Yoshimura Yoshiaki Amakura Toshiyuki Murakami Ko Tahara Hideyuki Ito |
| author_sort | Haruna Uemori |
| collection | DOAJ |
| description | <i>Eucalyptus camaldulensis</i> of the Myrtaceae family shows high resistance to aluminum (Al) ions and contains various compounds such as steroids, terpenoids, saponins, flavonoids, glycosides, alkaloids, and tannins. Although the ellagitannin oenothein B (<b>12</b>) isolated from <i>E. camaldulensis</i> exhibits remarkable properties for Al detoxification, likely contributing to its Al resistance, other ellagitannin oligomers present in <i>E. camaldulensis</i> have not been investigated in detail. In this study, novel dimeric and trimeric ellagitannin oligomers eucarpanin D<sub>2</sub> (<b>1</b>) and eucamalin A (<b>2</b>), together with known gallotannins (<b>7</b>, <b>8</b>, and <b>10</b>), monomeric ellagitannins (<b>4</b>–<b>6</b>, and <b>11</b>), and dimeric ellagitannins (<b>3</b>, <b>9</b>, and <b>12</b>–<b>14</b>), were isolated from <i>E. camaldulensis</i> leaves. The structures of these novel compounds were elucidated based on their chemical and physicochemical properties, including the orientations of tergalloyl groups in compounds <b>1</b> and <b>2</b>. Similar to compound <b>12</b>, previously isolated from the roots of <i>E. camaldulensis</i>, the ellagitannins demonstrated good Al detoxification properties. Hence, these tannins may play a critical role in the high Al resistance of <i>E. camaldulensis</i> in acidic soils. This paper reports for the first time the isolation of ellagitannin oligomers from the leaves of <i>E. camaldulensis</i>. |
| format | Article |
| id | doaj-art-5396f16647c245ee8ecc3452bc1580f3 |
| institution | Kabale University |
| issn | 1420-3049 |
| language | English |
| publishDate | 2025-05-01 |
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| series | Molecules |
| spelling | doaj-art-5396f16647c245ee8ecc3452bc1580f32025-08-20T03:48:02ZengMDPI AGMolecules1420-30492025-05-013010221610.3390/molecules30102216Ellagitannin Oligomers from <i>Eucalyptus camaldulensis</i> Leaves and Their Role in the Detoxification of AluminumHaruna Uemori0Ayano Inoue1Shoichi Suzuki2Yuji Iwaoka3Tsutomu Hatano4Morio Yoshimura5Yoshiaki Amakura6Toshiyuki Murakami7Ko Tahara8Hideyuki Ito9Doctorate Course of Health and Welfare Science, Graduate School of Okayama Prefectural University, 111 Kuboki, Soja 719-1197, Okayama, JapanFaculty of Health and Welfare Science, Okayama Prefectural University, 111 Kuboki, Soja 719-1197, Okayama, JapanFaculty of Health and Welfare Science, Okayama Prefectural University, 111 Kuboki, Soja 719-1197, Okayama, JapanDoctorate Course of Health and Welfare Science, Graduate School of Okayama Prefectural University, 111 Kuboki, Soja 719-1197, Okayama, JapanDivision of Pharmaceutical Sciences, Graduate School of Medicine, Dentistry, Pharmaceutical Sciences, Okayama University, 1-1-1 Tsushima-Naka, Kita-ku 700-8530, Okayama, JapanPharmaceutical Sciences, Matsuyama University, 4-2 Bunkyo-cho, Matsuyama 790-8578, Ehime, JapanPharmaceutical Sciences, Matsuyama University, 4-2 Bunkyo-cho, Matsuyama 790-8578, Ehime, JapanResearch Center, Maruzen Pharmaceuticals, Co., Ltd., 1089-8 Sagata, Shinnichi-Cho, Fukuyama 729-3102, Hiroshima, JapanForestry and Forest Products Research Institute, 1 Matunosato, Tsukuba 305-8687, Ibaraki, JapanDoctorate Course of Health and Welfare Science, Graduate School of Okayama Prefectural University, 111 Kuboki, Soja 719-1197, Okayama, Japan<i>Eucalyptus camaldulensis</i> of the Myrtaceae family shows high resistance to aluminum (Al) ions and contains various compounds such as steroids, terpenoids, saponins, flavonoids, glycosides, alkaloids, and tannins. Although the ellagitannin oenothein B (<b>12</b>) isolated from <i>E. camaldulensis</i> exhibits remarkable properties for Al detoxification, likely contributing to its Al resistance, other ellagitannin oligomers present in <i>E. camaldulensis</i> have not been investigated in detail. In this study, novel dimeric and trimeric ellagitannin oligomers eucarpanin D<sub>2</sub> (<b>1</b>) and eucamalin A (<b>2</b>), together with known gallotannins (<b>7</b>, <b>8</b>, and <b>10</b>), monomeric ellagitannins (<b>4</b>–<b>6</b>, and <b>11</b>), and dimeric ellagitannins (<b>3</b>, <b>9</b>, and <b>12</b>–<b>14</b>), were isolated from <i>E. camaldulensis</i> leaves. The structures of these novel compounds were elucidated based on their chemical and physicochemical properties, including the orientations of tergalloyl groups in compounds <b>1</b> and <b>2</b>. Similar to compound <b>12</b>, previously isolated from the roots of <i>E. camaldulensis</i>, the ellagitannins demonstrated good Al detoxification properties. Hence, these tannins may play a critical role in the high Al resistance of <i>E. camaldulensis</i> in acidic soils. This paper reports for the first time the isolation of ellagitannin oligomers from the leaves of <i>E. camaldulensis</i>.https://www.mdpi.com/1420-3049/30/10/2216<i>Eucalyptus camaldulensis</i> Dehnh.ellagitannin oligomereucamalin Aeucarpanin D<sub>2</sub>eurobustin CAl detoxification |
| spellingShingle | Haruna Uemori Ayano Inoue Shoichi Suzuki Yuji Iwaoka Tsutomu Hatano Morio Yoshimura Yoshiaki Amakura Toshiyuki Murakami Ko Tahara Hideyuki Ito Ellagitannin Oligomers from <i>Eucalyptus camaldulensis</i> Leaves and Their Role in the Detoxification of Aluminum Molecules <i>Eucalyptus camaldulensis</i> Dehnh. ellagitannin oligomer eucamalin A eucarpanin D<sub>2</sub> eurobustin C Al detoxification |
| title | Ellagitannin Oligomers from <i>Eucalyptus camaldulensis</i> Leaves and Their Role in the Detoxification of Aluminum |
| title_full | Ellagitannin Oligomers from <i>Eucalyptus camaldulensis</i> Leaves and Their Role in the Detoxification of Aluminum |
| title_fullStr | Ellagitannin Oligomers from <i>Eucalyptus camaldulensis</i> Leaves and Their Role in the Detoxification of Aluminum |
| title_full_unstemmed | Ellagitannin Oligomers from <i>Eucalyptus camaldulensis</i> Leaves and Their Role in the Detoxification of Aluminum |
| title_short | Ellagitannin Oligomers from <i>Eucalyptus camaldulensis</i> Leaves and Their Role in the Detoxification of Aluminum |
| title_sort | ellagitannin oligomers from i eucalyptus camaldulensis i leaves and their role in the detoxification of aluminum |
| topic | <i>Eucalyptus camaldulensis</i> Dehnh. ellagitannin oligomer eucamalin A eucarpanin D<sub>2</sub> eurobustin C Al detoxification |
| url | https://www.mdpi.com/1420-3049/30/10/2216 |
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