Biochemical Systematics and Ecology最新文献

{"title":"Chemical constituents of Alchornea rugosa and their chemotaxonomic significance","authors":"Xin-Xin Liang ,&nbsp;Ming-Hao Mao ,&nbsp;Si-Cheng Jin ,&nbsp;Jia-Yi Zhang ,&nbsp;Lei Wu ,&nbsp;Jiao-Ying Qu ,&nbsp;Jiao-Jiao Pan ,&nbsp;Xiang-Guo Meng","doi":"10.1016/j.bse.2025.105118","DOIUrl":"10.1016/j.bse.2025.105118","url":null,"abstract":"<div><div>A phytochemical investigation of <em>Alchornea rugosa</em> resulted in the isolation of one stilbene glycoside (<strong>1</strong>), four megastigmane-type sesquiterpenes (<strong>2</strong>–<strong>5</strong>), nine flavonoids (<strong>6–14</strong>) and four phenols (<strong>15</strong>–<strong>18</strong>). These compounds were elucidated using spectroscopic methods and comparing their data to those reported in the literature. Among them, compounds <strong>1</strong>, <strong>2</strong>, and <strong>12</strong>–<strong>15</strong> were first isolated from Euphorbiaceae family. Compounds <strong>3</strong>–<strong>6</strong>, <strong>8</strong>, <strong>11</strong>, and <strong>18</strong> were initially obtained from the genus <em>Alchornea</em>, while compounds <strong>7</strong>, <strong>9</strong>, <strong>10</strong>, <strong>16</strong>, and <strong>17</strong> have not been previously isolated from this species. In addition, the chemotaxonomic significance of the isolated compounds was discussed.</div></div>","PeriodicalId":8799,"journal":{"name":"Biochemical Systematics and Ecology","volume":"123 ","pages":"Article 105118"},"PeriodicalIF":2.0,"publicationDate":"2025-08-30","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"144917036","PeriodicalName":null,"FirstCategoryId":null,"ListUrlMain":null,"RegionNum":4,"RegionCategory":"生物学","ArticlePicture":[],"TitleCN":null,"AbstractTextCN":null,"PMCID":"","EPubDate":null,"PubModel":null,"JCR":null,"JCRName":null,"Score":null,"Total":0}

{"title":"Chemical constituents of Cachrys libanotis L. and their chemotaxonomic significance","authors":"Nabila Bouderdra ,&nbsp;Salah Akkal ,&nbsp;Kamel Medjroubi ,&nbsp;Hamza Fadel ,&nbsp;Elisabeth Seguin","doi":"10.1016/j.bse.2025.105117","DOIUrl":"10.1016/j.bse.2025.105117","url":null,"abstract":"<div><div>Through a phytochemical analysis of the aerial portions of <em>Cachrys libanotis</em> L., eight compounds, including seven coumarins and a derivative of a flavonoid glycoside, as well as a novel linear dihydropyranocoumarin was isolated and characterized. Spectroscopic analysis was used to clarify the separated chemicals' structures. <em>C. libanotis</em> was the source of compounds <strong>3</strong> and <strong>4</strong>, whereas compound <strong>5</strong> was a novel angular pyranocoumarin derivative. In fact, compounds <strong>3</strong>, <strong>5</strong>, and <strong>6</strong> have been isolated for the first time from the genus <em>Cachrys</em>. Moreover, the chemotaxonomic significance of these identified chemicals was covered in this article.</div></div>","PeriodicalId":8799,"journal":{"name":"Biochemical Systematics and Ecology","volume":"123 ","pages":"Article 105117"},"PeriodicalIF":2.0,"publicationDate":"2025-08-29","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"144912184","PeriodicalName":null,"FirstCategoryId":null,"ListUrlMain":null,"RegionNum":4,"RegionCategory":"生物学","ArticlePicture":[],"TitleCN":null,"AbstractTextCN":null,"PMCID":"","EPubDate":null,"PubModel":null,"JCR":null,"JCRName":null,"Score":null,"Total":0}

{"title":"Chemophenetically relevant iridoids and phenolics from Betonica and Stachys (Lamioideae, Lamiaceae)","authors":"Isabelle Herre ,&nbsp;Thomas Stegemann ,&nbsp;Christian Zidorn","doi":"10.1016/j.bse.2025.105113","DOIUrl":"10.1016/j.bse.2025.105113","url":null,"abstract":"<div><div>Betonica L. and <em>Stachys</em> L. are closely related genera within the Lamiaceae family, yet comparative phytochemical data on their secondary metabolites remain limited. In this study, we investigated and compared the iridoid and phenolic profiles of selected species from both genera to better understand their secondary metabolite diversity. RP-UHPLC-DAD-HRMS analyses of the methanolic extracts of three <em>Betonica</em> species (<em>B. alopecuros</em> L., <em>B</em>. <em>macrantha</em> K.Koch, and <em>B. officinalis</em> L.) and three <em>Stachys</em> species [<em>S</em>. <em>arvensis</em> (L.) L., <em>S. byzantina</em> K.Koch, and <em>S. sylvatica</em> L.] revealed pronounced differences in their secondary metabolite profiles. Chlorogenic acid, harpagide, and martynoside were detected in all investigated species. The iridoid glycoside allobetonicoside was present exclusively in the examined <em>Betonica</em> species, while flavone glycosides showed genus-specific patterns: isoscutellarein and hypolaetin derivatives occurred only in <em>Stachys</em>, whereas tricin and tricetin glucuronides were restricted to <em>Betonica</em>. These differences highlight distinct secondary metabolite profiles between the two genera. Allobetonicoside, tricin 7-<em>O</em>-glucuronide, and tricetin 3′,4′,5′-trimethyl ether-7-<em>O</em>-glucuronide might therefore serve as chemophenetic markers for the genus <em>Betonica</em>, while the presence of hypolaetin 4′-methylether 7-<em>O</em>-[6‴-acetylallosyl (1→2) glucoside] and isoscutellarein 7-<em>O</em>-[6‴-acetylallosyl (1→2) glucoside] exclusively in <em>Stachys</em> supports their value as marker compounds for this genus.</div><div>Tricetin 3′,4′,5′-trimethyl ether-7-<em>O</em>-glucuronide, which had previously only been reported from <em>Artemisia frigida</em> Willd. (Asteraceae) as friginoside A, was isolated from <em>B. officinalis</em>. A detailed analysis of the methanolic extract of <em>B. officinalis</em> confirmed the presence of known compounds, including the phenylpropanoids verbascoside, forsythoside B, leucosceptoside B, martynoside, betonyoside F, and stachysoside B; the iridoids harpagide, 8-<em>O</em>-acetylharpagide, and allobetonicoside; and the flavonoid isoorientin. These findings might contribute to chemophentically characterize the genera <em>Betonica</em> and <em>Stachys</em>.</div></div>","PeriodicalId":8799,"journal":{"name":"Biochemical Systematics and Ecology","volume":"123 ","pages":"Article 105113"},"PeriodicalIF":2.0,"publicationDate":"2025-08-26","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"144895895","PeriodicalName":null,"FirstCategoryId":null,"ListUrlMain":null,"RegionNum":4,"RegionCategory":"生物学","ArticlePicture":[],"TitleCN":null,"AbstractTextCN":null,"PMCID":"","EPubDate":null,"PubModel":null,"JCR":null,"JCRName":null,"Score":null,"Total":0}

{"title":"Corrigendum to “Biomarker identification in warehouse beetle (Trogoderma variabile) larvae: Tracking metabolic shifts across grain hosts” [Biochem. Systemat. Ecol. 120 (2025) 104983]","authors":"Thamer Al-Shuwaili ,&nbsp;Khalid Mohammed ,&nbsp;Pushpendra Koli ,&nbsp;Sonu Kumar Mahawer ,&nbsp;Anup Kumar","doi":"10.1016/j.bse.2025.105116","DOIUrl":"10.1016/j.bse.2025.105116","url":null,"abstract":"","PeriodicalId":8799,"journal":{"name":"Biochemical Systematics and Ecology","volume":"123 ","pages":"Article 105116"},"PeriodicalIF":2.0,"publicationDate":"2025-08-25","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"145004153","PeriodicalName":null,"FirstCategoryId":null,"ListUrlMain":null,"RegionNum":4,"RegionCategory":"生物学","ArticlePicture":[],"TitleCN":null,"AbstractTextCN":null,"PMCID":"","EPubDate":null,"PubModel":null,"JCR":null,"JCRName":null,"Score":null,"Total":0}

{"title":"Chemical constituents with chemotaxonomic value from Yunnanopilia longistaminaea","authors":"Liangrui Yang ,&nbsp;Yan Wu ,&nbsp;Shengqi Zhang ,&nbsp;Yaxin Liu ,&nbsp;Lifu Wu ,&nbsp;Yongfan Zi ,&nbsp;Tianpeng Yin ,&nbsp;Le Cai","doi":"10.1016/j.bse.2025.105112","DOIUrl":"10.1016/j.bse.2025.105112","url":null,"abstract":"<div><div>A systematic investigation was conducted on the chemical constituents of <em>Yunnanopilia longistaminaea</em>, a wild edible woody plant endemic to China. Twenty-two compounds, including one lactone (<strong>1</strong>), one phenolic acid (<strong>2</strong>), three phenylpropanoids (<strong>3</strong>–<strong>5</strong>), five terpenoids (<strong>6</strong>–<strong>10</strong>), eight nitrogen-containing heterocyclic compounds (<strong>11</strong>–<strong>18</strong>), three steroids (<strong>19</strong>–<strong>21</strong>), and one aliphatic chain compound (<strong>22</strong>), were isolated and identified. Among these, 18 compounds were isolated from this plant for the first time. An evaluating of the chemotaxonomic significance of these compounds revealed that compounds <strong>1</strong>, <strong>5</strong>, <strong>6</strong>, <strong>7</strong>, <strong>11</strong>, and <strong>22</strong> exhibit notable distribution specificity within the genus <em>Yunnanopilia</em>, serving as characteristic chemotaxonomic markers for both the genus and the family Opiliaceae. These findings provide new chemical evidence for the taxonomy and phylogenetic studies of <em>Y</em>. <em>longistaminaea</em>.</div></div>","PeriodicalId":8799,"journal":{"name":"Biochemical Systematics and Ecology","volume":"123 ","pages":"Article 105112"},"PeriodicalIF":2.0,"publicationDate":"2025-08-22","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"144885794","PeriodicalName":null,"FirstCategoryId":null,"ListUrlMain":null,"RegionNum":4,"RegionCategory":"生物学","ArticlePicture":[],"TitleCN":null,"AbstractTextCN":null,"PMCID":"","EPubDate":null,"PubModel":null,"JCR":null,"JCRName":null,"Score":null,"Total":0}

{"title":"Chemical constituents from Magnolia grandiflora Linn leaves and their chemotaxonomic significance","authors":"Fang Liu ,&nbsp;Zhongqin Zhang ,&nbsp;Chunmao Yuan ,&nbsp;Jun Jin","doi":"10.1016/j.bse.2025.105110","DOIUrl":"10.1016/j.bse.2025.105110","url":null,"abstract":"<div><div>A phytochemical investigation of the leaves of <em>Magnolia grandiflora</em> Linn. afforded eighteen compounds, including six sequiterpenes (<strong>1</strong>–<strong>6</strong>), six alkaloids (<strong>7</strong>–<strong>12</strong>), four phenylpropanoids (<strong>13</strong>–<strong>16</strong>), and two benzaldehyde derivatives (<strong>17</strong>–<strong>18</strong>). Their structural elucidation was achieved by comprehensive NMR analysis as well as by comparison of their spectroscopic date with the literature. Among them, <strong>2</strong> and <strong>3</strong> are firstly isolated and identified as nature products from plant source, <strong>11</strong> and <strong>12</strong> are being firstly reported from the family Magnoliaceae, and <strong>4</strong>–<strong>6</strong> and <strong>15</strong> were obtained from the genus <em>Magnolia</em> for the first time. This work contributes to the understanding of the chemical diversity of <em>M</em>. <em>grandiflora</em> and also the chemotaxonomic significance of these isolated compounds is discussed.</div></div>","PeriodicalId":8799,"journal":{"name":"Biochemical Systematics and Ecology","volume":"123 ","pages":"Article 105110"},"PeriodicalIF":2.0,"publicationDate":"2025-08-19","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"144866024","PeriodicalName":null,"FirstCategoryId":null,"ListUrlMain":null,"RegionNum":4,"RegionCategory":"生物学","ArticlePicture":[],"TitleCN":null,"AbstractTextCN":null,"PMCID":"","EPubDate":null,"PubModel":null,"JCR":null,"JCRName":null,"Score":null,"Total":0}

{"title":"The chemotypes of Ethiopian Echinops kebericho accessions","authors":"Bekri Melka Abdo ,&nbsp;Bizuayehu Tesfaye Asfaw ,&nbsp;M. Iqbal Choudhary ,&nbsp;Sammer Yousuf ,&nbsp;Solomon Abate Mekonnen ,&nbsp;Wendawek Abebe Mengesha","doi":"10.1016/j.bse.2025.105111","DOIUrl":"10.1016/j.bse.2025.105111","url":null,"abstract":"<div><div>The chemotype of essential oils plays a crucial role in classifying plant subspecies with similar morphological traits and optimizing their biological activities. This study characterized and classified the chemotype of 45 accessions of <em>Echinops kebericho</em>, collected from different geographical areas of Ethiopia, based on 15 major chemical constituents of their root essential oil. The chemical composition was analyzed using GC-MS, and chemotype classification was performed through multivariate statistical analysis. Principal component analysis and hierarchical clustering formed the accessions into four groups, leading to the identification of three distinct chemotypes. Chemotype A was characterized by a high concentration of dehydrocostus lactone, β-guaiene, and δ-cadinene, while chemotype B contained dehydrocostus lactone, β-guaiene, and caryophyllene oxide. Chemotype C, designated as the dehydrocostus lactone type, was dominated by dehydrocostus lactone. The north Ethiopia kebericho population was uniformly classified as chemotype C, whereas the other populations exhibited chemotypic diversity, encompassing all three chemotypes. These findings highlight significant chemical variability among kebericho accessions, which originated from various geographical locations of Ethiopia. This chemophenetic approach provides a valuable foundation for the targeted improvement, sustainable production, utilization, and conservation of kebericho plant.</div></div>","PeriodicalId":8799,"journal":{"name":"Biochemical Systematics and Ecology","volume":"123 ","pages":"Article 105111"},"PeriodicalIF":2.0,"publicationDate":"2025-08-18","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"144860877","PeriodicalName":null,"FirstCategoryId":null,"ListUrlMain":null,"RegionNum":4,"RegionCategory":"生物学","ArticlePicture":[],"TitleCN":null,"AbstractTextCN":null,"PMCID":"","EPubDate":null,"PubModel":null,"JCR":null,"JCRName":null,"Score":null,"Total":0}

{"title":"Chemical, chemophenetic and antiproliferative studies of Cattleya purpurata","authors":"Diego Luiz Lucca ,&nbsp;Gredson Keiff de Souza ,&nbsp;Silas Halede de Carvalho ,&nbsp;Silvana Maria de Oliveira ,&nbsp;Melyssa Fernanda Norman Negri ,&nbsp;Deisiany Gomes ,&nbsp;Paula Derksen Macruz ,&nbsp;Eduardo Jorge Pilau ,&nbsp;Maria Auxiliadora Milaneze-Gutierre ,&nbsp;Armando Mateus Pomini","doi":"10.1016/j.bse.2025.105114","DOIUrl":"10.1016/j.bse.2025.105114","url":null,"abstract":"<div><div>This study investigates the phytochemical composition, cytotoxic activity, and chemophenetic relationships of <em>Cattleya purpurata</em>, a prominent Brazilian orchid. Despite its widespread cultivation for ornamental and commercial purposes, the phytochemical profile of <em>C. purpurata</em> remains underexplored. Phytochemical analysis led to the isolation and identification of 12 compounds using nuclear magnetic resonance (NMR) spectroscopy: the triterpene 24-methylenecycloartanol (<strong>1</strong>), the steroids β-sitosterol (<strong>2</strong>), stigmasterol (<strong>3</strong>), and campesterol (<strong>4</strong>), the phenanthrenequinones phocanthone (<strong>5</strong>) and ephemeranthoquinone (<strong>8</strong>), the stilbenoids stilbostemin J (<strong>6</strong>) and 3′-<em>O</em>-methylbatatasin III (<strong>10</strong>), the dihydrophenanthrenes coelonin (<strong>11</strong>) and lusianthridin (<strong>12</strong>), and the phenolic acids salicylic acid (<strong>7</strong>) and phloretic acid (<strong>9</strong>). Dereplication studies employing ultra-high-performance liquid chromatography coupled with high-resolution time-of-flight mass spectrometry (UHPLC-QToF-HR-MS/MS) enabled the putative identification of additional compounds, the alkaloid feruloytyramine (<strong>13</strong>), the monoterpene lactone loliolide (<strong>14</strong>), the nucleoside methylsulfinyladenosine (<strong>15</strong>), the stilbene gigantol (<strong>16</strong>), and the phenolic compounds methoxyhydroxytyrosol (<strong>17</strong>) and syringic acid glucosyl ester (<strong>18</strong>). Cytotoxicity assays were conducted on human HeLa cancer cells and non-tumor VERO cell lines using the crude extract and fractions. Chemophenetic analysis suggests a close relationship between <em>C. purpurata</em> and the related species <em>C. tigrina</em> and <em>C. intermedia</em>, supported by shared morphological and genetic traits that facilitate even natural hybridization. These findings underscore <em>C. purpurata</em> as a valuable taxon for chemophenetic studies within the <em>Cattleya</em> genus.</div></div>","PeriodicalId":8799,"journal":{"name":"Biochemical Systematics and Ecology","volume":"123 ","pages":"Article 105114"},"PeriodicalIF":2.0,"publicationDate":"2025-08-17","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"144858271","PeriodicalName":null,"FirstCategoryId":null,"ListUrlMain":null,"RegionNum":4,"RegionCategory":"生物学","ArticlePicture":[],"TitleCN":null,"AbstractTextCN":null,"PMCID":"","EPubDate":null,"PubModel":null,"JCR":null,"JCRName":null,"Score":null,"Total":0}

{"title":"Triterpenoid saponins from the seeds of Aralia elata (Miq.) Seem. and their chemotaxonomic significance","authors":"Wu-Di Zhai ,&nbsp;Wen-Hao Zong ,&nbsp;Bo-Yue Xiao ,&nbsp;Chen-Yang Liu ,&nbsp;Xiao-Ping Zhang ,&nbsp;Yan Zhang","doi":"10.1016/j.bse.2025.105115","DOIUrl":"10.1016/j.bse.2025.105115","url":null,"abstract":"<div><div>Phytochemical research was conducted on the seeds of <em>Aralia elata</em> (Miq.) Seem., resulting in the isolation of twelve compounds. The chemical structures of the compounds were elucidated through spectral analysis, and the obtained nuclear magnetic resonance (NMR) spectra were systematically compared with published literature values. Among the isolated compounds, compound <strong>1</strong> was an undescribed compound, while compound <strong>6</strong> was isolated for the first time from the genus <em>Aralia</em>. The chemotaxonomic significance was further analyzed and discussed.</div></div>","PeriodicalId":8799,"journal":{"name":"Biochemical Systematics and Ecology","volume":"123 ","pages":"Article 105115"},"PeriodicalIF":2.0,"publicationDate":"2025-08-16","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"144853004","PeriodicalName":null,"FirstCategoryId":null,"ListUrlMain":null,"RegionNum":4,"RegionCategory":"生物学","ArticlePicture":[],"TitleCN":null,"AbstractTextCN":null,"PMCID":"","EPubDate":null,"PubModel":null,"JCR":null,"JCRName":null,"Score":null,"Total":0}

{"title":"A new norlignan and other compounds from Artemisia frigida Willd","authors":"Xin-Ya Dong ,&nbsp;Ru-Ya Li ,&nbsp;Hong-Xia Tang ,&nbsp;Ya-Jie Li ,&nbsp;Jun Chen ,&nbsp;Jin-Guo Luo ,&nbsp;Na Yu ,&nbsp;Xiang-Wei Xu ,&nbsp;Xu-Dong Zhou","doi":"10.1016/j.bse.2025.105102","DOIUrl":"10.1016/j.bse.2025.105102","url":null,"abstract":"<div><div><em>Artemisia frigida</em> is an endemic plant that only grows in China and its phytochemistry has never been fully appreciated and sufficiently studied. In the present study, a phytochemical investigation on the aerial parts of <em>A</em>. <em>frigida</em> resulted in the isolation of a new norlignan (<strong>1</strong>), together with twelve known constituents (<strong>2</strong>–<strong>13</strong>). Their structures were established by NMR spectroscopic analysis and comparison of their data with previous literature. Compound <strong>1</strong> existed as racemic mixtures, and all of the compounds were isolated from <em>A. frigida</em> for the first time except compounds <strong>2</strong>–<strong>5</strong>. Moreover, the chemotaxonomic significance corresponding to the above compounds was investigated.</div></div>","PeriodicalId":8799,"journal":{"name":"Biochemical Systematics and Ecology","volume":"123 ","pages":"Article 105102"},"PeriodicalIF":2.0,"publicationDate":"2025-08-05","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"144772208","PeriodicalName":null,"FirstCategoryId":null,"ListUrlMain":null,"RegionNum":4,"RegionCategory":"生物学","ArticlePicture":[],"TitleCN":null,"AbstractTextCN":null,"PMCID":"","EPubDate":null,"PubModel":null,"JCR":null,"JCRName":null,"Score":null,"Total":0}