Zhao, Ze-Yu and Wan, Jiang and Chen, Hao-Wei and Sun, Zhong-Shuai and Tao, Yu-Tian and Tong, Yingpeng and Zang, Yi and Choo, Yeun-Mun and Wang, Pan and Li, Yue-Ling and Jiang, Chun-Xiao and Li, Junming and Xiong, Juan and Li, Jia and Jin, Ze-Xin and Hu, Jin-Feng (2024) Major specialized natural products from the endangered plant Heptacodium miconioides, , potential medicinal uses and insights into its longstanding unresolved systematic classification. Phytochemistry, 228. p. 114259. ISSN 0031-9422, DOI https://doi.org/10.1016/j.phytochem.2024.114259.
Full text not available from this repository.Abstract
A comprehensive phytochemical investigation of the flower buds and leaves/twigs of Heptacodium miconioides, a cultivated ornamental plant native to China and categorized as `vulnerable', has led to the isolation of 45 structurally diverse compounds, which comprise 18 phenylpropanoids (<bold>1</bold>-<bold>4</bold>, <bold>7</bold>-<bold>20</bold>), 11 pentacyclic triterpenoids (<bold>5</bold>, <bold>6</bold>, <bold>21</bold>-<bold>29</bold>), eight secoiridoid glycosides (<bold>30</bold>-<bold>37</bold>), three quinic acid derivatives (<bold>38</bold>-<bold>40</bold>), and a few miscellaneous components (<bold>41</bold>-<bold>45</bold>). Among them, (+)-alpha-intermedianol (<bold>1</bold>), (+)-holophyllol A (<bold>2</bold>), and (-)-pseudolarkaemin A (<bold>3</bold>) represent previously unreported enantiomeric lignans, while (+)-7 `(R)-hydroxymatairesinol (<bold>4</bold>) is an undescribed naturally occurring lignan. Heptacoacids A (<bold>5</bold>) and B (<bold>6</bold>) are undescribed 24-nor-urs-28-oic acid derivatives. Their chemical structures were determined by 2D-NMR, supplemented by evidence from specific rotations and circular dichroism spectra. Given the uncertainty surrounding the systematic position of Heptacodium, integrative taxonomy (ITA), a method utilized to define contentious species, is applied. Chemotaxonomy, a vital aspect of ITA, becomes significant. By employing hierarchical clustering analysis (HCA) and syntenic pattern analysis methods, a taxonomic examination based on the major specialized natural products from the flower buds of H. miconioides and two other Caprifoliaceae plants (i.e., Lonicera japonica and Abelia x grandiflora) could offer enhanced understanding of the systematic placement of Heptacodium. Additionally, compounds <bold>39</bold> and <bold>40</bold> displayed remarkable inhibitory activities against ATP-citrate lyase (ACL), with IC50 values of 0.11 and 1.10 mu M, respectively. In summary, the discovery of medical properties and refining systematic classification can establish a sturdy groundwork for conservation efforts aimed at mitigating species diversity loss while addressing human diseases.
| Item Type: | Article |
|---|---|
| Funders: | National Natural Science Foundation of China (NSFC) (21937002) ; (81773599), Natural Science Foundation of Zhejiang Province (LY23H300001) ; (LTY22C030002) |
| Uncontrolled Keywords: | Heptacodium miconioides; Caprifoliaceae; Systematic position; Chemotaxonomy; Enantiomeric lignans; Triterpenoids; Quinic acid derivatives; ACL inhibitory |
| Subjects: | Q Science > QK Botany R Medicine > RM Therapeutics. Pharmacology R Medicine > RS Pharmacy and materia medica |
| Divisions: | Faculty of Science > Department of Chemistry |
| Depositing User: | Ms. Juhaida Abd Rahim |
| Date Deposited: | 09 Apr 2025 06:38 |
| Last Modified: | 09 Apr 2025 06:38 |
| URI: | http://eprints.um.edu.my/id/eprint/46604 |
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