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Hokkaido University Collection of Scholarly and Academic Papers >
Graduate School of Agriculture / Faculty of Agriculture >
Peer-reviewed Journal Articles, etc >
Pennelliiside D, a New Acyl Glucose from Solanum pennellii and Chemical Synthesis of Pennelliisides
| Title: | Pennelliiside D, a New Acyl Glucose from Solanum pennellii and Chemical Synthesis of Pennelliisides |
| Authors: | Masimbula, Rishni Browse this author | | Kobayashi, Hiroto Browse this author | | Nakashima, Tenki Browse this author | | Nambu, Yurika Browse this author | | Kitaoka, Naoki Browse this author →KAKEN DB | | Matsuura, Hideyuki Browse this author →KAKEN DB |
| Keywords: | Solanum pennellii | | acyl glucose | | pennelliisides | | trichomes | | acyl sugars |
| Issue Date: | Jun-2022 |
| Publisher: | MDPI |
| Journal Title: | Molecules |
| Volume: | 27 |
| Issue: | 12 |
| Start Page: | 3728 |
| Publisher DOI: | 10.3390/molecules27123728 |
| Abstract: | Acyl glucoses are a group of specialized metabolites produced by Solanaceae. Solanum pennellii, 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 S. pennellii. 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 beta-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-O-diisobutyryl-2-O-((S)-2-methylbutyryl)-D-glucose. Pennelliiside D and its constituent fatty acid moiety, (S)-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-O-dibenzylpennelliisides A and B. |
| Type: | article |
| URI: | http://hdl.handle.net/2115/86346 |
| Appears in Collections: | 農学院・農学研究院 (Graduate School of Agriculture / Faculty of Agriculture) > 雑誌発表論文等 (Peer-reviewed Journal Articles, etc)
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