Li Yan, Wan-Bai Su, Zhi-Yang Tang, Yang Yu, Jin-Song Liu, Yun-Peng Sun, Guo-Kai Wang
{"title":"中国脚草的化学成分及其化学分类意义","authors":"Li Yan, Wan-Bai Su, Zhi-Yang Tang, Yang Yu, Jin-Song Liu, Yun-Peng Sun, Guo-Kai Wang","doi":"10.1016/j.bse.2025.105119","DOIUrl":null,"url":null,"abstract":"<div><div>Twenty-five compounds were isolated from the aerial parts of <em>Clinopodium chinense</em> (Benth.) O. Kuntze, including eight triterpenoids (<strong>1</strong>–<strong>8</strong>), nine flavonoids (<strong>9</strong>–<strong>17</strong>), three megastigmanes (<strong>18</strong>–<strong>20</strong>), four phenylpropanoids (<strong>21</strong>–<strong>24</strong>), and one phenolic compound (<strong>25</strong>). Their structures were elucidated using NMR spectroscopy and verified by comparison with literature data. Among them, compounds <strong>3</strong> and <strong>4</strong> were obtained from this plant for the first time. Compounds <strong>23</strong> was isolated for the first time from the genus <em>Clinopodium</em>. Compounds <strong>18</strong>, <strong>19</strong>, <strong>24</strong>, and <strong>25</strong> were reported for the first time in the family Lamiaceae. Additionally, <strong>3</strong>, <strong>7</strong>, <strong>23</strong>, and <strong>25</strong> exhibited notable anti-inflammatory activity, with <strong>7</strong> displaying the most potent inhibitory effect (IC<sub>50</sub> = 3.33 ± 0.52 μM). Furthermore, a detailed discussion was provided regarding the chemotaxonomic significance of the isolated compounds. These findings not only offer chemotaxonomic evidence for evaluating the phylogenetic relationships between Lamiaceae and other plant families, but also substantially expand the known structural diversity of specialized metabolites within this family.</div></div>","PeriodicalId":8799,"journal":{"name":"Biochemical Systematics and Ecology","volume":"123 ","pages":"Article 105119"},"PeriodicalIF":2.0000,"publicationDate":"2025-08-30","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":"0","resultStr":"{\"title\":\"Chemical constituents from Clinopodium chinense and their chemotaxonomic significance\",\"authors\":\"Li Yan, Wan-Bai Su, Zhi-Yang Tang, Yang Yu, Jin-Song Liu, Yun-Peng Sun, Guo-Kai Wang\",\"doi\":\"10.1016/j.bse.2025.105119\",\"DOIUrl\":null,\"url\":null,\"abstract\":\"<div><div>Twenty-five compounds were isolated from the aerial parts of <em>Clinopodium chinense</em> (Benth.) O. Kuntze, including eight triterpenoids (<strong>1</strong>–<strong>8</strong>), nine flavonoids (<strong>9</strong>–<strong>17</strong>), three megastigmanes (<strong>18</strong>–<strong>20</strong>), four phenylpropanoids (<strong>21</strong>–<strong>24</strong>), and one phenolic compound (<strong>25</strong>). Their structures were elucidated using NMR spectroscopy and verified by comparison with literature data. Among them, compounds <strong>3</strong> and <strong>4</strong> were obtained from this plant for the first time. Compounds <strong>23</strong> was isolated for the first time from the genus <em>Clinopodium</em>. Compounds <strong>18</strong>, <strong>19</strong>, <strong>24</strong>, and <strong>25</strong> were reported for the first time in the family Lamiaceae. Additionally, <strong>3</strong>, <strong>7</strong>, <strong>23</strong>, and <strong>25</strong> exhibited notable anti-inflammatory activity, with <strong>7</strong> displaying the most potent inhibitory effect (IC<sub>50</sub> = 3.33 ± 0.52 μM). Furthermore, a detailed discussion was provided regarding the chemotaxonomic significance of the isolated compounds. These findings not only offer chemotaxonomic evidence for evaluating the phylogenetic relationships between Lamiaceae and other plant families, but also substantially expand the known structural diversity of specialized metabolites within this family.</div></div>\",\"PeriodicalId\":8799,\"journal\":{\"name\":\"Biochemical Systematics and Ecology\",\"volume\":\"123 \",\"pages\":\"Article 105119\"},\"PeriodicalIF\":2.0000,\"publicationDate\":\"2025-08-30\",\"publicationTypes\":\"Journal Article\",\"fieldsOfStudy\":null,\"isOpenAccess\":false,\"openAccessPdf\":\"\",\"citationCount\":\"0\",\"resultStr\":null,\"platform\":\"Semanticscholar\",\"paperid\":null,\"PeriodicalName\":\"Biochemical Systematics and Ecology\",\"FirstCategoryId\":\"99\",\"ListUrlMain\":\"https://www.sciencedirect.com/science/article/pii/S0305197825001681\",\"RegionNum\":4,\"RegionCategory\":\"生物学\",\"ArticlePicture\":[],\"TitleCN\":null,\"AbstractTextCN\":null,\"PMCID\":null,\"EPubDate\":\"\",\"PubModel\":\"\",\"JCR\":\"Q4\",\"JCRName\":\"BIOCHEMISTRY & MOLECULAR BIOLOGY\",\"Score\":null,\"Total\":0}","platform":"Semanticscholar","paperid":null,"PeriodicalName":"Biochemical Systematics and Ecology","FirstCategoryId":"99","ListUrlMain":"https://www.sciencedirect.com/science/article/pii/S0305197825001681","RegionNum":4,"RegionCategory":"生物学","ArticlePicture":[],"TitleCN":null,"AbstractTextCN":null,"PMCID":null,"EPubDate":"","PubModel":"","JCR":"Q4","JCRName":"BIOCHEMISTRY & MOLECULAR BIOLOGY","Score":null,"Total":0}
Chemical constituents from Clinopodium chinense and their chemotaxonomic significance
Twenty-five compounds were isolated from the aerial parts of Clinopodium chinense (Benth.) O. Kuntze, including eight triterpenoids (1–8), nine flavonoids (9–17), three megastigmanes (18–20), four phenylpropanoids (21–24), and one phenolic compound (25). Their structures were elucidated using NMR spectroscopy and verified by comparison with literature data. Among them, compounds 3 and 4 were obtained from this plant for the first time. Compounds 23 was isolated for the first time from the genus Clinopodium. Compounds 18, 19, 24, and 25 were reported for the first time in the family Lamiaceae. Additionally, 3, 7, 23, and 25 exhibited notable anti-inflammatory activity, with 7 displaying the most potent inhibitory effect (IC50 = 3.33 ± 0.52 μM). Furthermore, a detailed discussion was provided regarding the chemotaxonomic significance of the isolated compounds. These findings not only offer chemotaxonomic evidence for evaluating the phylogenetic relationships between Lamiaceae and other plant families, but also substantially expand the known structural diversity of specialized metabolites within this family.
期刊介绍:
Biochemical Systematics and Ecology is devoted to the publication of original papers and reviews, both submitted and invited, in two subject areas: I) the application of biochemistry to problems relating to systematic biology of organisms (biochemical systematics); II) the role of biochemistry in interactions between organisms or between an organism and its environment (biochemical ecology).
In the Biochemical Systematics subject area, comparative studies of the distribution of (secondary) metabolites within a wider taxon (e.g. genus or family) are welcome. Comparative studies, encompassing multiple accessions of each of the taxa within their distribution are particularly encouraged. Welcome are also studies combining classical chemosystematic studies (such as comparative HPLC-MS or GC-MS investigations) with (macro-) molecular phylogenetic studies. Studies that involve the comparative use of compounds to help differentiate among species such as adulterants or substitutes that illustrate the applied use of chemosystematics are welcome. In contrast, studies solely employing macromolecular phylogenetic techniques (gene sequences, RAPD studies etc.) will be considered out of scope. Discouraged are manuscripts that report known or new compounds from a single source taxon without addressing a systematic hypothesis. Also considered out of scope are studies using outdated and hard to reproduce macromolecular techniques such as RAPDs in combination with standard chemosystematic techniques such as GC-FID and GC-MS.