Pennelliiside D, a New Acyl Glucose from <i>Solanum pennellii</i> and Chemical Synthesis of Pennelliisides
Acyl glucoses are a group of specialized metabolites produced by Solanaceae. <i>Solanum pennellii</i>, a wild-type tomato plant, produces acyl glucoses in its hair-like epidermal structures known as trichomes. These compounds have been found to be herbicides, microbial growth inhibitors,...
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MDPI AG
2022-06-01
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| author | Rishni Masimbula Hiroto Kobayashi Tenki Nakashima Yurika Nambu Naoki Kitaoka Hideyuki Matsuura |
| author_facet | Rishni Masimbula Hiroto Kobayashi Tenki Nakashima Yurika Nambu Naoki Kitaoka Hideyuki Matsuura |
| author_sort | Rishni Masimbula |
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| description | Acyl glucoses are a group of specialized metabolites produced by Solanaceae. <i>Solanum pennellii</i>, a wild-type tomato plant, produces acyl glucoses in its hair-like epidermal structures known as trichomes. These compounds have been found to be herbicides, microbial growth inhibitors, or allelopathic compounds. However, there are a few reports regarding isolation and investigation of biological activities of acyl glucoses in its pure form due to the difficulty of isolation. Here, we report a new acyl glucose, pennelliiside D, isolated and identified from <i>S. pennellii</i>. Its structure was determined by 1D NMR and 2D NMR, together with FD-MS analysis. To clarify the absolute configuration of the acyl moiety of 2-methylbutyryl in the natural compound, two possible isomers were synthesized starting from <i>β</i>-D-glucose pentaacetate. By comparing the spectroscopic data of natural and synthesized compounds of isomers, the structure of pennelliiside D was confirmed to be 3,4-<i>O</i>-diisobutyryl-2-<i>O</i>-((<i>S</i>)-2-methylbutyryl)-D-glucose. Pennelliiside D and its constituent fatty acid moiety, (<i>S</i>)-2-methylbutanoic acid, did not show root growth-inhibitory activity. Additionally, in this study, chemical synthesis pathways toward pennelliisides A and B were adapted to give 1,6-<i>O</i>-dibenzylpennelliisides A and B. |
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| last_indexed | 2024-03-09T22:56:05Z |
| publishDate | 2022-06-01 |
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| series | Molecules |
| spelling | doaj.art-4d9c2ae4c08e4dbd802d3a907d3dce112023-11-23T18:10:14ZengMDPI AGMolecules1420-30492022-06-012712372810.3390/molecules27123728Pennelliiside D, a New Acyl Glucose from <i>Solanum pennellii</i> and Chemical Synthesis of PennelliisidesRishni Masimbula0Hiroto Kobayashi1Tenki Nakashima2Yurika Nambu3Naoki Kitaoka4Hideyuki Matsuura5Research Faculty of Agriculture, Hokkaido University, Kita 9 Nishi 9, Kita-ku, Sapporo 060-8589, JapanResearch Faculty of Agriculture, Hokkaido University, Kita 9 Nishi 9, Kita-ku, Sapporo 060-8589, JapanResearch Faculty of Agriculture, Hokkaido University, Kita 9 Nishi 9, Kita-ku, Sapporo 060-8589, JapanResearch Faculty of Agriculture, Hokkaido University, Kita 9 Nishi 9, Kita-ku, Sapporo 060-8589, JapanResearch Faculty of Agriculture, Hokkaido University, Kita 9 Nishi 9, Kita-ku, Sapporo 060-8589, JapanResearch Faculty of Agriculture, Hokkaido University, Kita 9 Nishi 9, Kita-ku, Sapporo 060-8589, JapanAcyl glucoses are a group of specialized metabolites produced by Solanaceae. <i>Solanum pennellii</i>, a wild-type tomato plant, produces acyl glucoses in its hair-like epidermal structures known as trichomes. These compounds have been found to be herbicides, microbial growth inhibitors, or allelopathic compounds. However, there are a few reports regarding isolation and investigation of biological activities of acyl glucoses in its pure form due to the difficulty of isolation. Here, we report a new acyl glucose, pennelliiside D, isolated and identified from <i>S. pennellii</i>. Its structure was determined by 1D NMR and 2D NMR, together with FD-MS analysis. To clarify the absolute configuration of the acyl moiety of 2-methylbutyryl in the natural compound, two possible isomers were synthesized starting from <i>β</i>-D-glucose pentaacetate. By comparing the spectroscopic data of natural and synthesized compounds of isomers, the structure of pennelliiside D was confirmed to be 3,4-<i>O</i>-diisobutyryl-2-<i>O</i>-((<i>S</i>)-2-methylbutyryl)-D-glucose. Pennelliiside D and its constituent fatty acid moiety, (<i>S</i>)-2-methylbutanoic acid, did not show root growth-inhibitory activity. Additionally, in this study, chemical synthesis pathways toward pennelliisides A and B were adapted to give 1,6-<i>O</i>-dibenzylpennelliisides A and B.https://www.mdpi.com/1420-3049/27/12/3728<i>Solanum pennellii</i>acyl glucosepennelliisidestrichomesacyl sugars |
| spellingShingle | Rishni Masimbula Hiroto Kobayashi Tenki Nakashima Yurika Nambu Naoki Kitaoka Hideyuki Matsuura Pennelliiside D, a New Acyl Glucose from <i>Solanum pennellii</i> and Chemical Synthesis of Pennelliisides Molecules <i>Solanum pennellii</i> acyl glucose pennelliisides trichomes acyl sugars |
| title | Pennelliiside D, a New Acyl Glucose from <i>Solanum pennellii</i> and Chemical Synthesis of Pennelliisides |
| title_full | Pennelliiside D, a New Acyl Glucose from <i>Solanum pennellii</i> and Chemical Synthesis of Pennelliisides |
| title_fullStr | Pennelliiside D, a New Acyl Glucose from <i>Solanum pennellii</i> and Chemical Synthesis of Pennelliisides |
| title_full_unstemmed | Pennelliiside D, a New Acyl Glucose from <i>Solanum pennellii</i> and Chemical Synthesis of Pennelliisides |
| title_short | Pennelliiside D, a New Acyl Glucose from <i>Solanum pennellii</i> and Chemical Synthesis of Pennelliisides |
| title_sort | pennelliiside d a new acyl glucose from i solanum pennellii i and chemical synthesis of pennelliisides |
| topic | <i>Solanum pennellii</i> acyl glucose pennelliisides trichomes acyl sugars |
| url | https://www.mdpi.com/1420-3049/27/12/3728 |
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