{"title":"来自 Chasmanthera dependens Hochst.(Menispermaceae)中的一种新的抗菌新橙皮烷二萜类化合物和其他成分及其化学分类学意义","authors":"Serges H. Ngalaha Ediah , Elodie Gaële Matheuda , Brio Azonsop Kefossang , Yves M.Mba Nguekeu , Takeshi Kodama , Saw Yu Yu Hnin , Zhuang Qian , Maurice Ducret Awouafack , Apollinaire Tsopmo , Hiroyuki Morita , Mathieu Tene","doi":"10.1016/j.bse.2024.104922","DOIUrl":null,"url":null,"abstract":"<div><div>The leaves, stems and fruits methanol extracts of <em>Chasmanthera dependens</em> were chemically investigated to afford one new <em>neo</em>-clerodane diterpenoid (<strong>1</strong>) along with seventeen known compounds including three diterpenoids (<strong>2</strong>–<strong>4</strong>), six triterpenoids (<strong>5</strong>–<strong>10</strong>), four steroids (<strong>11</strong>–<strong>14</strong>), one sesquiterpenoid (<strong>15</strong>), one lignan (<strong>16</strong>) and two phenolic acids (<strong>17</strong> and 1<strong>8</strong>). Structures were established by analysis of their spectroscopic and spectrometric data and in comparison with those reported from the literature. Except columbin (<strong>2</strong>), compounds are reported for the first time from the genus <em>Chasmanthera</em>. The extracts, fractions, and isolated compounds were subjected to <em>in vitro</em> antibacterial assays against three Gram-positive and three Gram-negative bacteria, using the broth microdilution method. The MeOH extract of the leaves and its fractions F1<strong>–</strong>F4 had significant (MIC = 93.8 μg/mL for F4) or moderate (187.5 ≤ MIC ≤ 375 μg/mL) activities against <em>Pseudomonas aeruginosa</em>. Chasmantherenolide (<strong>1</strong>) was moderately active (MIC = 75 μg/mL, 202.6 μM) against Gram-positive bacterial strains. Significant antibacterial activity (MIC = 9.4 μg/mL, 20.6 μM) was recorded for oleanolic acid (<strong>7</strong>) against <em>Mycobacterium smegmatis</em>. The chemotaxonomic significance of the isolated compounds was discussed.</div></div>","PeriodicalId":8799,"journal":{"name":"Biochemical Systematics and Ecology","volume":"118 ","pages":"Article 104922"},"PeriodicalIF":1.4000,"publicationDate":"2024-11-22","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":"0","resultStr":"{\"title\":\"A new antibacterial neo-clerodane diterpenoid and other constituents from Chasmanthera dependens Hochst. (Menispermaceae) and their chemotaxonomic significance\",\"authors\":\"Serges H. Ngalaha Ediah , Elodie Gaële Matheuda , Brio Azonsop Kefossang , Yves M.Mba Nguekeu , Takeshi Kodama , Saw Yu Yu Hnin , Zhuang Qian , Maurice Ducret Awouafack , Apollinaire Tsopmo , Hiroyuki Morita , Mathieu Tene\",\"doi\":\"10.1016/j.bse.2024.104922\",\"DOIUrl\":null,\"url\":null,\"abstract\":\"<div><div>The leaves, stems and fruits methanol extracts of <em>Chasmanthera dependens</em> were chemically investigated to afford one new <em>neo</em>-clerodane diterpenoid (<strong>1</strong>) along with seventeen known compounds including three diterpenoids (<strong>2</strong>–<strong>4</strong>), six triterpenoids (<strong>5</strong>–<strong>10</strong>), four steroids (<strong>11</strong>–<strong>14</strong>), one sesquiterpenoid (<strong>15</strong>), one lignan (<strong>16</strong>) and two phenolic acids (<strong>17</strong> and 1<strong>8</strong>). Structures were established by analysis of their spectroscopic and spectrometric data and in comparison with those reported from the literature. Except columbin (<strong>2</strong>), compounds are reported for the first time from the genus <em>Chasmanthera</em>. The extracts, fractions, and isolated compounds were subjected to <em>in vitro</em> antibacterial assays against three Gram-positive and three Gram-negative bacteria, using the broth microdilution method. The MeOH extract of the leaves and its fractions F1<strong>–</strong>F4 had significant (MIC = 93.8 μg/mL for F4) or moderate (187.5 ≤ MIC ≤ 375 μg/mL) activities against <em>Pseudomonas aeruginosa</em>. Chasmantherenolide (<strong>1</strong>) was moderately active (MIC = 75 μg/mL, 202.6 μM) against Gram-positive bacterial strains. Significant antibacterial activity (MIC = 9.4 μg/mL, 20.6 μM) was recorded for oleanolic acid (<strong>7</strong>) against <em>Mycobacterium smegmatis</em>. The chemotaxonomic significance of the isolated compounds was discussed.</div></div>\",\"PeriodicalId\":8799,\"journal\":{\"name\":\"Biochemical Systematics and Ecology\",\"volume\":\"118 \",\"pages\":\"Article 104922\"},\"PeriodicalIF\":1.4000,\"publicationDate\":\"2024-11-22\",\"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/S0305197824001418\",\"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/S0305197824001418","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}
A new antibacterial neo-clerodane diterpenoid and other constituents from Chasmanthera dependens Hochst. (Menispermaceae) and their chemotaxonomic significance
The leaves, stems and fruits methanol extracts of Chasmanthera dependens were chemically investigated to afford one new neo-clerodane diterpenoid (1) along with seventeen known compounds including three diterpenoids (2–4), six triterpenoids (5–10), four steroids (11–14), one sesquiterpenoid (15), one lignan (16) and two phenolic acids (17 and 18). Structures were established by analysis of their spectroscopic and spectrometric data and in comparison with those reported from the literature. Except columbin (2), compounds are reported for the first time from the genus Chasmanthera. The extracts, fractions, and isolated compounds were subjected to in vitro antibacterial assays against three Gram-positive and three Gram-negative bacteria, using the broth microdilution method. The MeOH extract of the leaves and its fractions F1–F4 had significant (MIC = 93.8 μg/mL for F4) or moderate (187.5 ≤ MIC ≤ 375 μg/mL) activities against Pseudomonas aeruginosa. Chasmantherenolide (1) was moderately active (MIC = 75 μg/mL, 202.6 μM) against Gram-positive bacterial strains. Significant antibacterial activity (MIC = 9.4 μg/mL, 20.6 μM) was recorded for oleanolic acid (7) against Mycobacterium smegmatis. The chemotaxonomic significance of the isolated compounds was discussed.
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.