Pub Date : 2025-09-18DOI: 10.1016/j.bse.2025.105139
Hou-Lin Peng , Man-Hui Yang , Wu-Di Zhai , Wen-Juan Li , Jing Liu , Yan Zhang
Phytochemical studies on the water extract of Gynostemma pentaphyllum led to the isolation of fifteen compounds, including three phenols, six phenylpropanoids, five lignans, and one five-membered alicyclic derivative. Extensive spectroscopic analysis and comparison with previously reported data were used to determine the chemical structures of the compounds. All constituents were firstly isolated from the genus for the first time. Furthermore, the chemotaxonomic significance of all isolated compounds was investigated.
{"title":"The chemotaxonomic significance of chemical constituents from Gynostemma pentaphyllum","authors":"Hou-Lin Peng , Man-Hui Yang , Wu-Di Zhai , Wen-Juan Li , Jing Liu , Yan Zhang","doi":"10.1016/j.bse.2025.105139","DOIUrl":"10.1016/j.bse.2025.105139","url":null,"abstract":"<div><div>Phytochemical studies on the water extract of <em>Gynostemma pentaphyllum</em> led to the isolation of fifteen compounds, including three phenols, six phenylpropanoids, five lignans, and one five-membered alicyclic derivative. Extensive spectroscopic analysis and comparison with previously reported data were used to determine the chemical structures of the compounds. All constituents were firstly isolated from the genus for the first time. Furthermore, the chemotaxonomic significance of all isolated compounds was investigated.</div></div>","PeriodicalId":8799,"journal":{"name":"Biochemical Systematics and Ecology","volume":"124 ","pages":"Article 105139"},"PeriodicalIF":2.0,"publicationDate":"2025-09-18","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"145107093","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}
Pub Date : 2025-09-12DOI: 10.1016/j.bse.2025.105122
Shivani Bhati, Aruna Joshi
The oleo-gum resins and essential oils from genus Commiphora Jacq. have been widely used commercially for different medicinal purposes all over the world. This study presents a tentative phytochemical profile of one of its lesser-known endangered species Commiphora stocksiana (Engl.) Engl. and a comparative assessment with Commiphora wightii (Arn.) Bhandari stem fractions. The fractionation was performed across three different solvent polarities; analysis of the fractions were performed using HPLC-MS-QToF in both positive and negative electrospray ionization (ESI) modes. The statistical analysis performed for the comparative assessment of the two species revealed that methanolic fractions displayed the most pronounced species-level separation, followed by moderate differentiation in ethyl acetate fractions, while petroleum ether fractions exhibited considerable overlap, indicating compositional similarity. The spectral library-based comparison of the features observed in each fraction led to tentative identification of 61 metabolites of varying compound classes in C. stocksiana. Further MS/MS fragmentation analysis of some features observed in petroleum ether fraction of C. stocksiana revealed the presence of Guggulsterone E, confirmed by alignment with a positive control from C. wightii using exact ion chromatogram tool in MS-DIAL. These findings were verified using HPLC analysis by using reference standard mix of Guggulsterone E and Z isomer. Additional feature showed retro-Diels-Alder (RDA) type cleavage of precursor ions, suggesting the presence of ursane- and oleanane-type pentacyclic triterpenoids, highly similar to the boswellic acid derivatives.
{"title":"Phytochemical investigation of Commiphora stocksiana (Engl.) Engl. and its comparative metabolomic study with Commiphora wightii (Arn.) Bhandari. Using HPLC-MS-Qtof","authors":"Shivani Bhati, Aruna Joshi","doi":"10.1016/j.bse.2025.105122","DOIUrl":"10.1016/j.bse.2025.105122","url":null,"abstract":"<div><div>The oleo-gum resins and essential oils from genus <em>Commiphora</em> Jacq. have been widely used commercially for different medicinal purposes all over the world. This study presents a tentative phytochemical profile of one of its lesser-known endangered species <em>Commiphora stocksiana</em> (Engl.) Engl. and a comparative assessment with <em>Commiphora wightii</em> (Arn.) Bhandari stem fractions. The fractionation was performed across three different solvent polarities; analysis of the fractions were performed using HPLC-MS-QToF in both positive and negative electrospray ionization (ESI) modes. The statistical analysis performed for the comparative assessment of the two species revealed that methanolic fractions displayed the most pronounced species-level separation, followed by moderate differentiation in ethyl acetate fractions, while petroleum ether fractions exhibited considerable overlap, indicating compositional similarity. The spectral library-based comparison of the features observed in each fraction led to tentative identification of 61 metabolites of varying compound classes in <em>C. stocksiana</em>. Further MS/MS fragmentation analysis of some features observed in petroleum ether fraction of <em>C. stocksiana</em> revealed the presence of Guggulsterone E, confirmed by alignment with a positive control from <em>C. wightii</em> using exact ion chromatogram tool in MS-DIAL. These findings were verified using HPLC analysis by using reference standard mix of Guggulsterone E and Z isomer. Additional feature showed retro-Diels-Alder (RDA) type cleavage of precursor ions, suggesting the presence of ursane- and oleanane-type pentacyclic triterpenoids, highly similar to the boswellic acid derivatives.</div></div>","PeriodicalId":8799,"journal":{"name":"Biochemical Systematics and Ecology","volume":"124 ","pages":"Article 105122"},"PeriodicalIF":2.0,"publicationDate":"2025-09-12","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"145046805","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}
Pub Date : 2025-09-11DOI: 10.1016/j.bse.2025.105136
Jin-Xin Zhu , Ze-Yu Zhao , Chi Song , Juan Xiong , Jin-Feng Hu
The white-berry yew [Pseudotaxus chienii (W. C. Cheng) W. C. Cheng], a monotypic species of the genus within the family Taxaceae, is an endangered Chinese endemic relict conifer. A preliminary phytochemical investigation on the ethyl acetate soluble fraction of the 90 % methanol extract from the renewable twigs and needles of P. chienii resulted in the isolation and characterization of 14 compounds, including one δ-tocopherol derivative (1), one nor-labdane (2) with a rare C14-skeleton, two taxoids (3, 4), one abietane-type diterpenoid (5), five ent-kaurane-type diterpenoids (6–10), one isopimarane-type diterpenoid (11), and three pentacyclic triterpenoids (12–14). Among them, compound 1 is previously undescribed. Compound 2 is reported herein as a new natural product. This study also briefly discussed the chemotaxonomic significance of the isolated taxane-type compounds (3, 4), which were obtained from the genus Pseudotaxus for the first time.
白莓红豆杉（Pseudotaxus chienii (W. C. Cheng) W. C. Cheng）是红豆杉科红豆杉属的单型种，是一种濒危的中国特有孑遗针叶树。对可再生木细枝和针叶90%甲醇提取物的乙酸乙酯可溶性组分进行了初步的植物化学研究，分离并鉴定了14个化合物，包括1个δ-生育酚衍生物(1)、1个具有罕见c14骨架的非labdane(2)、2个taxoids（3,4）、1个abietane-type二萜(5)、5个对-kaurane-type二萜（6-10）、1个异海玛烷-type二萜（11）和3个pentacyclic三萜（12-14）。其中，化合物1先前未描述过。化合物2是一种新的天然产物。本文还简要讨论了首次从Pseudotaxus属中分离得到的紫杉烷类化合物（3,4）的化学分类意义。
{"title":"Chemical constituents from the endangered tertiary relict conifer Pseudotaxus chienii (W. C. Cheng) W. C. Cheng and their chemotaxonomic significance","authors":"Jin-Xin Zhu , Ze-Yu Zhao , Chi Song , Juan Xiong , Jin-Feng Hu","doi":"10.1016/j.bse.2025.105136","DOIUrl":"10.1016/j.bse.2025.105136","url":null,"abstract":"<div><div>The white-berry yew [<em>Pseudotaxus chienii</em> (W. C. Cheng) W. C. Cheng], a monotypic species of the genus within the family Taxaceae, is an endangered Chinese endemic relict conifer. A preliminary phytochemical investigation on the ethyl acetate soluble fraction of the 90 % methanol extract from the renewable twigs and needles of <em>P. chienii</em> resulted in the isolation and characterization of 14 compounds, including one <em>δ-</em>tocopherol derivative (<strong>1</strong>), one <em>nor</em>-labdane (<strong>2</strong>) with a rare C14-skeleton, two taxoids (<strong>3</strong>, <strong>4</strong>), one abietane-type diterpenoid (<strong>5</strong>), five <em>ent</em>-kaurane-type diterpenoids (<strong>6</strong>–<strong>10</strong>), one isopimarane-type diterpenoid (<strong>11</strong>), and three pentacyclic triterpenoids (<strong>12</strong>–<strong>14</strong>). Among them, compound <strong>1</strong> is previously undescribed. Compound <strong>2</strong> is reported herein as a new natural product. This study also briefly discussed the chemotaxonomic significance of the isolated taxane-type compounds (<strong>3</strong>, <strong>4</strong>), which were obtained from the genus <em>Pseudotaxus</em> for the first time.</div></div>","PeriodicalId":8799,"journal":{"name":"Biochemical Systematics and Ecology","volume":"124 ","pages":"Article 105136"},"PeriodicalIF":2.0,"publicationDate":"2025-09-11","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"145046802","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}
Pub Date : 2025-09-11DOI: 10.1016/j.bse.2025.105121
Khadijeh Rihai Rad , Alireza Babaei , Mahmoud Kiani , Daniel Potter , Hamidreza Ardalani
This research employed GC-MS metabolomics profiling on bulbs of three genera i.e., Ornithogalum, Loncomelos, and Melomphis (Asparagaceae), to elucidate their taxonomic relationships. The analysis of 30 specimens across 8 species (Ornithogalum comprising 3 species: O. cuspidatum, O. neurostegium, O. orthophyllum; Loncomelos including 4 species: L. arcuatum, L. brachystachys, L. bungei, L. kurdicum; and Melomphis persica) from Iran revealed 147 detected metabolites, classified in several main superclasses e.g., organic oxygen compounds (40 %), organic acids (23 %), and lipids (18 %). Additionally, the metabolites were grouped into classes, with carbohydrates comprising the majority (42 %), followed by carboxylic acids (17 %) and fatty acids (14 %). Multivariate statistics including the variable importance in projection, and hierarchical clustering heat map discerned metabolites differentiating the genera. Projections to latent structures discriminant analysis revealed that Ornithogalum exhibited significant metabolic divergence from the closely related taxa Loncomelos and Melomphis, aligning with their established phylogenetic divisions. Overall, this work significantly expands knowledge of the chemodiversity of these taxa. The findings provide a phylogenetic framework to guide further ethno-pharmacological, phytochemical, and evolutionary research on these geophyte taxa.
{"title":"Metabolome fingerprinting elucidates chemodiversity in Ornithogalum, Loncomelos, and Melomphis (Asparagaceae)","authors":"Khadijeh Rihai Rad , Alireza Babaei , Mahmoud Kiani , Daniel Potter , Hamidreza Ardalani","doi":"10.1016/j.bse.2025.105121","DOIUrl":"10.1016/j.bse.2025.105121","url":null,"abstract":"<div><div>This research employed GC-MS metabolomics profiling on bulbs of three genera i.e., <em>Ornithogalum</em>, <em>Loncomelos</em>, and <em>Melomphis</em> (Asparagaceae), to elucidate their taxonomic relationships. The analysis of 30 specimens across 8 species (<em>Ornithogalum</em> comprising 3 species: <em>O. cuspidatum</em>, <em>O. neurostegium</em>, <em>O. orthophyllum</em>; <em>Loncomelos</em> including 4 species: <em>L. arcuatum</em>, <em>L. brachystachys</em>, <em>L. bungei</em>, <em>L. kurdicum</em>; and <em>Melomphis persica</em>) from Iran revealed 147 detected metabolites, classified in several main superclasses e.g., organic oxygen compounds (40 %), organic acids (23 %), and lipids (18 %). Additionally, the metabolites were grouped into classes, with carbohydrates comprising the majority (42 %), followed by carboxylic acids (17 %) and fatty acids (14 %). Multivariate statistics including the variable importance in projection, and hierarchical clustering heat map discerned metabolites differentiating the genera. Projections to latent structures discriminant analysis revealed that <em>Ornithogalum</em> exhibited significant metabolic divergence from the closely related taxa <em>Loncomelos</em> and <em>Melomphis</em>, aligning with their established phylogenetic divisions. Overall, this work significantly expands knowledge of the chemodiversity of these taxa. The findings provide a phylogenetic framework to guide further ethno-pharmacological, phytochemical, and evolutionary research on these geophyte taxa.</div></div>","PeriodicalId":8799,"journal":{"name":"Biochemical Systematics and Ecology","volume":"124 ","pages":"Article 105121"},"PeriodicalIF":2.0,"publicationDate":"2025-09-11","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"145046803","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}
Pub Date : 2025-09-07DOI: 10.1016/j.bse.2025.105131
Haijun Wang , Jing Wang , Chunyu Fu , Jiafeng Wang , Lei Liu , Jiaming Wang
A phytochemical investigation of the aerial parts of Baeckea frutescens L. (Myrtaceae) identified twenty-two compounds, including seven flavonoids (1–7), five coumarins (8–12), five triterpenoids (13–17), one monophenol (18), one phenolic glycoside (19), one chromone (20), one ionone (21) and one dihydrochalcone (22). The structures of these compounds were determined by spectroscopic data analysis and comparison with literature. Compounds 3–7, 8, 9, 10, 12, 14, 16 and 22 were first found from the genus Baeckea, while compounds 11, 19 and 20 were first reported within the family Myrtaceae. Furthermore, the chemotaxonomic significance of these compounds was discussed.
{"title":"Chemical constituents of Baeckea frutescens L. and their chemotaxonomic significance","authors":"Haijun Wang , Jing Wang , Chunyu Fu , Jiafeng Wang , Lei Liu , Jiaming Wang","doi":"10.1016/j.bse.2025.105131","DOIUrl":"10.1016/j.bse.2025.105131","url":null,"abstract":"<div><div>A phytochemical investigation of the aerial parts of <em>Baeckea frutescens</em> L. (Myrtaceae) identified twenty-two compounds, including seven flavonoids (<strong>1</strong>–<strong>7</strong>), five coumarins (<strong>8</strong>–<strong>12</strong>), five triterpenoids (<strong>13</strong>–<strong>17</strong>), one monophenol (<strong>18</strong>), one phenolic glycoside (<strong>19</strong>), one chromone (<strong>20</strong>), one ionone (<strong>21</strong>) and one dihydrochalcone (<strong>22</strong>). The structures of these compounds were determined by spectroscopic data analysis and comparison with literature. Compounds <strong>3</strong>–<strong>7</strong>, <strong>8</strong>, <strong>9</strong>, <strong>10</strong>, <strong>12</strong>, <strong>14</strong>, <strong>16</strong> and <strong>22</strong> were first found from the genus <em>Baeckea</em>, while compounds <strong>11</strong>, <strong>19</strong> and <strong>20</strong> were first reported within the family Myrtaceae. Furthermore, the chemotaxonomic significance of these compounds was discussed.</div></div>","PeriodicalId":8799,"journal":{"name":"Biochemical Systematics and Ecology","volume":"124 ","pages":"Article 105131"},"PeriodicalIF":2.0,"publicationDate":"2025-09-07","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"145011045","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}
Comprehensive metabolomic analysis on the leaf extracts of Scilla lakusicii and S. litardierei revealed the presence of 175 secondary metabolites. The identified compounds were categorized into several groups based on their chemical structures: hydroxybenzoic acids, hydroxycinnamic acids, saponins, flavonoid glycosides, flavonoid aglycones, homoisoflavonoid glycosides, homoisoflavonoid aglycones, and other metabolites. Saponins were the most abundant in both species, with some detected for the first time in plant tissues. Regarding volatile compounds, extracts from both species contained α- and β-pinene, neophytadiene, and phytol. S. litardierei showed a higher capacity to neutralize DPPH radicals, while S. lakusicii was more effective in scavenging hydroxyl radicals and reducing Fe3+ and Cu2+ ions. Both species exhibited similar capacities for H2O2 removal and Fe chelation. In terms of anticandidal activity, S. lakusicii was particularly effective against Candida glabrata and resistant C. auris, the latter of which showed no response to the standard drug ketoconazole. S. litardierei was more effective against C. glabrata. Both extracts demonstrated significant efficacy against resistant Escherichia coli in terms of antibacterial activity, while S. litardierei proved more effective against resistant Pseudomonas aeruginosa. Overall, leaf extracts of both Scilla species displayed significant antioxidant and antimicrobial activity, attributable to their specific chemical composition. The richness of secondary metabolites and pronounced biological activity enable the adaptation of these Scilla species to karst environments.
{"title":"Secondary metabolites and biochemical adaptations of Scilla lakusicii and S. litardierei to karst environments: a metabolomic perspective","authors":"Biljana Kukavica , Siniša Škondrić , Uroš Gašić , Dejan Stojković , Filip Nikolić , Tanja Trifković , Đura Nakarada , Miloš Mojović , Danijela Mišić","doi":"10.1016/j.bse.2025.105123","DOIUrl":"10.1016/j.bse.2025.105123","url":null,"abstract":"<div><div>Comprehensive metabolomic analysis on the leaf extracts of <em>Scilla lakusicii</em> and <em>S. litardierei</em> revealed the presence of 175 secondary metabolites. The identified compounds were categorized into several groups based on their chemical structures: hydroxybenzoic acids, hydroxycinnamic acids, saponins, flavonoid glycosides, flavonoid aglycones, homoisoflavonoid glycosides, homoisoflavonoid aglycones, and other metabolites. Saponins were the most abundant in both species, with some detected for the first time in plant tissues. Regarding volatile compounds, extracts from both species contained α- and β-pinene, neophytadiene, and phytol. <em>S. litardierei</em> showed a higher capacity to neutralize DPPH radicals, while <em>S. lakusicii</em> was more effective in scavenging hydroxyl radicals and reducing Fe<sup>3+</sup> and Cu<sup>2+</sup> ions. Both species exhibited similar capacities for H<sub>2</sub>O<sub>2</sub> removal and Fe chelation. In terms of anticandidal activity, <em>S. lakusicii</em> was particularly effective against <em>Candida glabrata</em> and resistant <em>C. auris</em>, the latter of which showed no response to the standard drug ketoconazole. <em>S. litardierei</em> was more effective against <em>C. glabrata</em>. Both extracts demonstrated significant efficacy against resistant <em>Escherichia coli</em> in terms of antibacterial activity, while <em>S. litardierei</em> proved more effective against resistant <em>Pseudomonas aeruginosa</em>. Overall, leaf extracts of both <em>Scilla</em> species displayed significant antioxidant and antimicrobial activity, attributable to their specific chemical composition. The richness of secondary metabolites and pronounced biological activity enable the adaptation of these <em>Scilla</em> species to karst environments.</div></div>","PeriodicalId":8799,"journal":{"name":"Biochemical Systematics and Ecology","volume":"124 ","pages":"Article 105123"},"PeriodicalIF":2.0,"publicationDate":"2025-09-06","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"145004394","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}
Pub Date : 2025-09-02DOI: 10.1016/j.bse.2025.105120
Yang Liu , Jie Chen , Wan-Wan Yu , Yong-Ming Luo , Meng-Li He , Xin-Yu Chen , Fang-You Chen
Continual phytochemical investigation on the aerial parts of Sarcandra glabra (Thunb.) Nakai afforded fifteen compounds (1–15), comprising twelve sesquiterpenoids (1–12) and three monoterpenoids (13–15). The structures of these compounds were assigned by means of spectroscopic analysis, including 1D/2D NMR, HRESIMS, ECD calculations, and single-crystal X-ray diffractions. Compound 1 was a previously undescribed cadinane-type sesquiterpene, while compounds 4, 5, 9, and 12–15 were isolated from S. glabra for the first time. Moreover, the chemotaxonomic significance of these constituents was also discussed.
{"title":"Sesquiterpenoids and monoterpenoids from the aerial parts of Sarcandra glabra (Thunb.) Nakai","authors":"Yang Liu , Jie Chen , Wan-Wan Yu , Yong-Ming Luo , Meng-Li He , Xin-Yu Chen , Fang-You Chen","doi":"10.1016/j.bse.2025.105120","DOIUrl":"10.1016/j.bse.2025.105120","url":null,"abstract":"<div><div>Continual phytochemical investigation on the aerial parts of <em>Sarcandra glabra</em> (Thunb.) Nakai afforded fifteen compounds (<strong>1</strong>–<strong>15</strong>), comprising twelve sesquiterpenoids (<strong>1</strong>–<strong>12</strong>) and three monoterpenoids (<strong>13</strong>–<strong>15</strong>). The structures of these compounds were assigned by means of spectroscopic analysis, including 1D/2D NMR, HRESIMS, ECD calculations, and single-crystal X-ray diffractions. Compound <strong>1</strong> was a previously undescribed cadinane-type sesquiterpene, while compounds <strong>4</strong>, <strong>5</strong>, <strong>9</strong>, and <strong>12</strong>–<strong>15</strong> were isolated from <em>S. glabra</em> for the first time. Moreover, the chemotaxonomic significance of these constituents was also discussed.</div></div>","PeriodicalId":8799,"journal":{"name":"Biochemical Systematics and Ecology","volume":"123 ","pages":"Article 105120"},"PeriodicalIF":2.0,"publicationDate":"2025-09-02","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"144925748","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}
Pub Date : 2025-08-30DOI: 10.1016/j.bse.2025.105119
Li Yan, Wan-Bai Su, Zhi-Yang Tang, Yang Yu, Jin-Song Liu, Yun-Peng Sun, Guo-Kai Wang
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.
{"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":"10.1016/j.bse.2025.105119","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":2.0,"publicationDate":"2025-08-30","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"144917037","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}
Pub Date : 2025-08-30DOI: 10.1016/j.bse.2025.105118
Xin-Xin Liang , Ming-Hao Mao , Si-Cheng Jin , Jia-Yi Zhang , Lei Wu , Jiao-Ying Qu , Jiao-Jiao Pan , Xiang-Guo Meng
A phytochemical investigation of Alchornea rugosa resulted in the isolation of one stilbene glycoside (1), four megastigmane-type sesquiterpenes (2–5), nine flavonoids (6–14) and four phenols (15–18). These compounds were elucidated using spectroscopic methods and comparing their data to those reported in the literature. Among them, compounds 1, 2, and 12–15 were first isolated from Euphorbiaceae family. Compounds 3–6, 8, 11, and 18 were initially obtained from the genus Alchornea, while compounds 7, 9, 10, 16, and 17 have not been previously isolated from this species. In addition, the chemotaxonomic significance of the isolated compounds was discussed.
{"title":"Chemical constituents of Alchornea rugosa and their chemotaxonomic significance","authors":"Xin-Xin Liang , Ming-Hao Mao , Si-Cheng Jin , Jia-Yi Zhang , Lei Wu , Jiao-Ying Qu , Jiao-Jiao Pan , 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}
Pub Date : 2025-08-29DOI: 10.1016/j.bse.2025.105117
Nabila Bouderdra , Salah Akkal , Kamel Medjroubi , Hamza Fadel , Elisabeth Seguin
Through a phytochemical analysis of the aerial portions of Cachrys libanotis 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. C. libanotis was the source of compounds 3 and 4, whereas compound 5 was a novel angular pyranocoumarin derivative. In fact, compounds 3, 5, and 6 have been isolated for the first time from the genus Cachrys. Moreover, the chemotaxonomic significance of these identified chemicals was covered in this article.
{"title":"Chemical constituents of Cachrys libanotis L. and their chemotaxonomic significance","authors":"Nabila Bouderdra , Salah Akkal , Kamel Medjroubi , Hamza Fadel , 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}
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