Challenging Structure Elucidation of Lumnitzeralactone, an Ellagic Acid Derivative from the Mangrove <i>Lumnitzera racemosa</i>
The previously undescribed natural product lumnitzeralactone (<b>1</b>), which represents a derivative of ellagic acid, was isolated from the anti-bacterial extract of the Indonesian mangrove species <i>Lumnitzera racemosa</i> Willd. The structure of lumnitzeralactone (<b&...
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| Format: | Article |
| Language: | English |
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MDPI AG
2023-04-01
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| Series: | Marine Drugs |
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| Online Access: | https://www.mdpi.com/1660-3397/21/4/242 |
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| author | Jonas Kappen Jeprianto Manurung Tristan Fuchs Sahithya Phani Babu Vemulapalli Lea M. Schmitz Andrej Frolov Andria Agusta Alexandra N. Muellner-Riehl Christian Griesinger Katrin Franke Ludger A. Wessjohann |
| author_facet | Jonas Kappen Jeprianto Manurung Tristan Fuchs Sahithya Phani Babu Vemulapalli Lea M. Schmitz Andrej Frolov Andria Agusta Alexandra N. Muellner-Riehl Christian Griesinger Katrin Franke Ludger A. Wessjohann |
| author_sort | Jonas Kappen |
| collection | DOAJ |
| description | The previously undescribed natural product lumnitzeralactone (<b>1</b>), which represents a derivative of ellagic acid, was isolated from the anti-bacterial extract of the Indonesian mangrove species <i>Lumnitzera racemosa</i> Willd. The structure of lumnitzeralactone (<b>1</b>), a proton-deficient and highly challenging condensed aromatic ring system, was unambiguously elucidated by extensive spectroscopic analyses involving high-resolution mass spectrometry (HRMS), 1D <sup>1</sup>H and <sup>13</sup>C nuclear magnetic resonance spectroscopy (NMR), and 2D NMR (including 1,1-ADEQUATE and 1,n-ADEQUATE). Determination of the structure was supported by computer-assisted structure elucidation (CASE system applying ACD-SE), density functional theory (DFT) calculations, and a two-step chemical synthesis. Possible biosynthetic pathways involving mangrove-associated fungi have been suggested. |
| first_indexed | 2024-03-11T04:48:24Z |
| format | Article |
| id | doaj.art-31bb33cff86942eea3ef23f6e461bed1 |
| institution | Directory Open Access Journal |
| issn | 1660-3397 |
| language | English |
| last_indexed | 2024-03-11T04:48:24Z |
| publishDate | 2023-04-01 |
| publisher | MDPI AG |
| record_format | Article |
| series | Marine Drugs |
| spelling | doaj.art-31bb33cff86942eea3ef23f6e461bed12023-11-17T20:10:29ZengMDPI AGMarine Drugs1660-33972023-04-0121424210.3390/md21040242Challenging Structure Elucidation of Lumnitzeralactone, an Ellagic Acid Derivative from the Mangrove <i>Lumnitzera racemosa</i>Jonas Kappen0Jeprianto Manurung1Tristan Fuchs2Sahithya Phani Babu Vemulapalli3Lea M. Schmitz4Andrej Frolov5Andria Agusta6Alexandra N. Muellner-Riehl7Christian Griesinger8Katrin Franke9Ludger A. Wessjohann10Department of Bioorganic Chemistry, Leibniz Institute of Plant Biochemistry (IPB), Weinberg 3, 06120 Halle (Saale), GermanyDepartment of Bioorganic Chemistry, Leibniz Institute of Plant Biochemistry (IPB), Weinberg 3, 06120 Halle (Saale), GermanyDepartment of Bioorganic Chemistry, Leibniz Institute of Plant Biochemistry (IPB), Weinberg 3, 06120 Halle (Saale), GermanyDepartment of NMR-Based Structural Biology, Max Planck Institute for Multidisciplinary Sciences, Am Fassberg 11, 37077 Göttingen, GermanyDepartment of Bioorganic Chemistry, Leibniz Institute of Plant Biochemistry (IPB), Weinberg 3, 06120 Halle (Saale), GermanyDepartment of Bioorganic Chemistry, Leibniz Institute of Plant Biochemistry (IPB), Weinberg 3, 06120 Halle (Saale), GermanyResearch Center for Pharmaceutical Ingredients and Traditional Medicine, National Research and Innovation Agency (BRIN), Jl. M.H. Thamrin No. 8, Jakarta 10340, IndonesiaDepartment of Molecular Evolution and Plant Systematics & Herbarium (LZ), Institute of Biology, Leipzig University, Johannisallee 21-23, 04103 Leipzig, GermanyDepartment of NMR-Based Structural Biology, Max Planck Institute for Multidisciplinary Sciences, Am Fassberg 11, 37077 Göttingen, GermanyDepartment of Bioorganic Chemistry, Leibniz Institute of Plant Biochemistry (IPB), Weinberg 3, 06120 Halle (Saale), GermanyDepartment of Bioorganic Chemistry, Leibniz Institute of Plant Biochemistry (IPB), Weinberg 3, 06120 Halle (Saale), GermanyThe previously undescribed natural product lumnitzeralactone (<b>1</b>), which represents a derivative of ellagic acid, was isolated from the anti-bacterial extract of the Indonesian mangrove species <i>Lumnitzera racemosa</i> Willd. The structure of lumnitzeralactone (<b>1</b>), a proton-deficient and highly challenging condensed aromatic ring system, was unambiguously elucidated by extensive spectroscopic analyses involving high-resolution mass spectrometry (HRMS), 1D <sup>1</sup>H and <sup>13</sup>C nuclear magnetic resonance spectroscopy (NMR), and 2D NMR (including 1,1-ADEQUATE and 1,n-ADEQUATE). Determination of the structure was supported by computer-assisted structure elucidation (CASE system applying ACD-SE), density functional theory (DFT) calculations, and a two-step chemical synthesis. Possible biosynthetic pathways involving mangrove-associated fungi have been suggested.https://www.mdpi.com/1660-3397/21/4/242<i>Lumnitzera racemosa</i>lumnitzeralactoneisolationsynthesisstructure elucidationellagic acid |
| spellingShingle | Jonas Kappen Jeprianto Manurung Tristan Fuchs Sahithya Phani Babu Vemulapalli Lea M. Schmitz Andrej Frolov Andria Agusta Alexandra N. Muellner-Riehl Christian Griesinger Katrin Franke Ludger A. Wessjohann Challenging Structure Elucidation of Lumnitzeralactone, an Ellagic Acid Derivative from the Mangrove <i>Lumnitzera racemosa</i> Marine Drugs <i>Lumnitzera racemosa</i> lumnitzeralactone isolation synthesis structure elucidation ellagic acid |
| title | Challenging Structure Elucidation of Lumnitzeralactone, an Ellagic Acid Derivative from the Mangrove <i>Lumnitzera racemosa</i> |
| title_full | Challenging Structure Elucidation of Lumnitzeralactone, an Ellagic Acid Derivative from the Mangrove <i>Lumnitzera racemosa</i> |
| title_fullStr | Challenging Structure Elucidation of Lumnitzeralactone, an Ellagic Acid Derivative from the Mangrove <i>Lumnitzera racemosa</i> |
| title_full_unstemmed | Challenging Structure Elucidation of Lumnitzeralactone, an Ellagic Acid Derivative from the Mangrove <i>Lumnitzera racemosa</i> |
| title_short | Challenging Structure Elucidation of Lumnitzeralactone, an Ellagic Acid Derivative from the Mangrove <i>Lumnitzera racemosa</i> |
| title_sort | challenging structure elucidation of lumnitzeralactone an ellagic acid derivative from the mangrove i lumnitzera racemosa i |
| topic | <i>Lumnitzera racemosa</i> lumnitzeralactone isolation synthesis structure elucidation ellagic acid |
| url | https://www.mdpi.com/1660-3397/21/4/242 |
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