{"title":"濒危植物 Heptacodium miconioides 的主要特殊天然产品、潜在药用价值以及对其长期悬而未决的系统分类的见解。","authors":"","doi":"10.1016/j.phytochem.2024.114259","DOIUrl":null,"url":null,"abstract":"<div><p>A comprehensive phytochemical investigation of the flower buds and leaves/twigs of <em>Heptacodium miconioides</em>, 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 (<strong>1</strong>–<strong>4</strong>, <strong>7</strong>–<strong>20</strong>), 11 pentacyclic triterpenoids (<strong>5</strong>, <strong>6</strong>, <strong>21</strong>–<strong>29</strong>), eight secoiridoid glycosides (<strong>30</strong>–<strong>37</strong>), three quinic acid derivatives (<strong>38</strong>–<strong>40</strong>), and a few miscellaneous components (<strong>41</strong>–<strong>45</strong>). Among them, (+)-<em>α</em>-intermedianol (<strong>1</strong>), (+)-holophyllol A (<strong>2</strong>), and (−)-pseudolarkaemin A (<strong>3</strong>) represent previously unreported enantiomeric lignans, while (+)-7′(<em>R</em>)-hydroxymatairesinol (<strong>4</strong>) is an undescribed naturally occurring lignan. Heptacoacids A (<strong>5</strong>) and B (<strong>6</strong>) are undescribed 24-<em>nor</em>-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 <em>Heptacodium</em>, 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 <em>H. miconioides</em> and two other Caprifoliaceae plants (i.e., <em>Lonicera japonica</em> and <em>Abelia</em> × <em>grandiflora</em>) could offer enhanced understanding of the systematic placement of <em>Heptacodium</em>. Additionally, compounds <strong>39</strong> and <strong>40</strong> displayed remarkable inhibitory activities against ATP-citrate lyase (ACL), with IC<sub>50</sub> values of 0.11 and 1.10 μM, 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.</p></div>","PeriodicalId":20170,"journal":{"name":"Phytochemistry","volume":null,"pages":null},"PeriodicalIF":3.2000,"publicationDate":"2024-08-24","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":"0","resultStr":"{\"title\":\"Major specialized natural products from the endangered plant Heptacodium miconioides, potential medicinal uses and insights into its longstanding unresolved systematic classification\",\"authors\":\"\",\"doi\":\"10.1016/j.phytochem.2024.114259\",\"DOIUrl\":null,\"url\":null,\"abstract\":\"<div><p>A comprehensive phytochemical investigation of the flower buds and leaves/twigs of <em>Heptacodium miconioides</em>, 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 (<strong>1</strong>–<strong>4</strong>, <strong>7</strong>–<strong>20</strong>), 11 pentacyclic triterpenoids (<strong>5</strong>, <strong>6</strong>, <strong>21</strong>–<strong>29</strong>), eight secoiridoid glycosides (<strong>30</strong>–<strong>37</strong>), three quinic acid derivatives (<strong>38</strong>–<strong>40</strong>), and a few miscellaneous components (<strong>41</strong>–<strong>45</strong>). Among them, (+)-<em>α</em>-intermedianol (<strong>1</strong>), (+)-holophyllol A (<strong>2</strong>), and (−)-pseudolarkaemin A (<strong>3</strong>) represent previously unreported enantiomeric lignans, while (+)-7′(<em>R</em>)-hydroxymatairesinol (<strong>4</strong>) is an undescribed naturally occurring lignan. Heptacoacids A (<strong>5</strong>) and B (<strong>6</strong>) are undescribed 24-<em>nor</em>-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 <em>Heptacodium</em>, 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 <em>H. miconioides</em> and two other Caprifoliaceae plants (i.e., <em>Lonicera japonica</em> and <em>Abelia</em> × <em>grandiflora</em>) could offer enhanced understanding of the systematic placement of <em>Heptacodium</em>. Additionally, compounds <strong>39</strong> and <strong>40</strong> displayed remarkable inhibitory activities against ATP-citrate lyase (ACL), with IC<sub>50</sub> values of 0.11 and 1.10 μM, 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.</p></div>\",\"PeriodicalId\":20170,\"journal\":{\"name\":\"Phytochemistry\",\"volume\":null,\"pages\":null},\"PeriodicalIF\":3.2000,\"publicationDate\":\"2024-08-24\",\"publicationTypes\":\"Journal Article\",\"fieldsOfStudy\":null,\"isOpenAccess\":false,\"openAccessPdf\":\"\",\"citationCount\":\"0\",\"resultStr\":null,\"platform\":\"Semanticscholar\",\"paperid\":null,\"PeriodicalName\":\"Phytochemistry\",\"FirstCategoryId\":\"99\",\"ListUrlMain\":\"https://www.sciencedirect.com/science/article/pii/S0031942224002966\",\"RegionNum\":2,\"RegionCategory\":\"生物学\",\"ArticlePicture\":[],\"TitleCN\":null,\"AbstractTextCN\":null,\"PMCID\":null,\"EPubDate\":\"\",\"PubModel\":\"\",\"JCR\":\"Q2\",\"JCRName\":\"BIOCHEMISTRY & MOLECULAR BIOLOGY\",\"Score\":null,\"Total\":0}","platform":"Semanticscholar","paperid":null,"PeriodicalName":"Phytochemistry","FirstCategoryId":"99","ListUrlMain":"https://www.sciencedirect.com/science/article/pii/S0031942224002966","RegionNum":2,"RegionCategory":"生物学","ArticlePicture":[],"TitleCN":null,"AbstractTextCN":null,"PMCID":null,"EPubDate":"","PubModel":"","JCR":"Q2","JCRName":"BIOCHEMISTRY & MOLECULAR BIOLOGY","Score":null,"Total":0}
引用次数: 0
摘要
Heptacodium miconioides 是一种原产于中国的栽培观赏植物,被归类为 "易危 "植物,对其花蕾和叶/枝进行的全面植物化学调查分离出了 45 种结构多样的化合物、其中包括 18 种苯基丙酸类化合物(1-4、7-20)、11 种五环三萜类化合物(5、6、21-29)、8 种琥珀酰胺苷类化合物(30-37)、3 种喹酸衍生物(38-40)以及一些杂项成分(41-45)。其中,(+)-α-intermedianol (1)、(+)-Holophyllol A (2)和(-)-pseudolarkaemin A (3)代表了以前未报道过的对映体木质素,而(+)-7'(R)-hydroxymatairesinol (4)则是一种未被描述过的天然木质素。Heptacoacids A (5) 和 B (6) 是未被描述过的 24-去甲-乌苏-28-酸衍生物。它们的化学结构是通过二维核磁共振以及特定旋转和圆二色光谱的证据确定的。鉴于 Heptacodium 的系统定位存在不确定性,因此采用了综合分类法 (ITA),这是一种用于定义有争议物种的方法。化学分类法是综合分类法的一个重要方面。通过采用层次聚类分析(HCA)和合成模式分析方法,基于 H. miconioides 和另外两种 Caprifoliaceae 植物(即 Lonicera japonica 和 Abelia × grandiflora)花蕾中的主要特化天然产物进行分类学研究,可以加深对 Heptacodium 的系统定位的理解。此外,化合物 39 和 40 对 ATP 柠檬酸酶(ACL)具有显著的抑制活性,IC50 值分别为 0.11 和 1.10 μM。总之,发现医学特性和完善系统分类可以为保护工作奠定坚实的基础,从而在解决人类疾病问题的同时减少物种多样性的丧失。
Major specialized natural products from the endangered plant Heptacodium miconioides, potential medicinal uses and insights into its longstanding unresolved systematic classification
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 (1–4, 7–20), 11 pentacyclic triterpenoids (5, 6, 21–29), eight secoiridoid glycosides (30–37), three quinic acid derivatives (38–40), and a few miscellaneous components (41–45). Among them, (+)-α-intermedianol (1), (+)-holophyllol A (2), and (−)-pseudolarkaemin A (3) represent previously unreported enantiomeric lignans, while (+)-7′(R)-hydroxymatairesinol (4) is an undescribed naturally occurring lignan. Heptacoacids A (5) and B (6) 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 × grandiflora) could offer enhanced understanding of the systematic placement of Heptacodium. Additionally, compounds 39 and 40 displayed remarkable inhibitory activities against ATP-citrate lyase (ACL), with IC50 values of 0.11 and 1.10 μM, 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.
期刊介绍:
Phytochemistry is a leading international journal publishing studies of plant chemistry, biochemistry, molecular biology and genetics, structure and bioactivities of phytochemicals, including ''-omics'' and bioinformatics/computational biology approaches. Phytochemistry is a primary source for papers dealing with phytochemicals, especially reports concerning their biosynthesis, regulation, and biological properties both in planta and as bioactive principles. Articles are published online as soon as possible as Articles-in-Press and in 12 volumes per year. Occasional topic-focussed special issues are published composed of papers from invited authors.