Pub Date : 2025-01-03DOI: 10.1016/j.phytochem.2025.114379
Xiao-Shan Shi , Sui-Qun Yang , Xiao-Ming Li , Yan-He Li , Dun-Jia Wang , Xin Li , Ling-Hong Meng , Xing-Wang Zhou , Bin-Gui Wang
Seven previously undescribed polyketide derivatives, fusariumtides A–G (1–7), together with three known analogues (8–10), were isolated from the culture extract of Fusarium asiaticum QA-6, an endophytic fungus obtained from the fresh stem tissue of the medicinal plant Artemisia argyi H. Lev. & Vaniot. Their structures were elucidated by detailed interpretation of 1D/2D NMR spectroscopic and mass spectrometric data, and the absolute configuration of compound 1 was established on the basis of X-ray crystallographic analysis and ECD and specific rotation (SR) calculations. The isolated compounds, which possessed a functionalized decalin moiety, were evaluated for antimicrobial activities. Compounds 1 and 10 exhibited broad-spectrum inhibitory activities against nine tested pathogenic bacteria with MIC values ranging from 1 to 64 μg/mL, while compound 8 showed potent inhibitory activities against aquatic pathogens Aeromonas hydrophilia, Pseudomonas aeruginosa, Vibrio harveyi, and V. vulnificus, which were comparable to/or stronger than those of the positive control chloramphenicol.
从药用植物艾蒿（Artemisia argyi H. Lev）的新鲜茎组织中获得的内生真菌亚洲镰刀菌QA-6的培养提取物中分离出7个先前未描述的聚酮衍生物，镰刀菌A-G（1-7）和3个已知的类似物（8-10）。& Vaniot。通过对1D/2D核磁共振光谱和质谱数据的详细解释，确定了化合物1的结构；通过x射线晶体学分析、ECD和比旋光度（SR）计算，确定了化合物1的绝对构型。分离得到的化合物具有功能化的十氢化萘片段，并对其抗菌活性进行了评价。化合物1和10对9种病原菌具有广谱抑制活性，MIC值为1 ~ 64 μg/mL；化合物8对水生病原菌亲水气单胞菌、铜绿假单胞菌、哈维弧菌和创伤弧菌具有较强的抑制活性，与阳性对照氯霉素相当或更强。
{"title":"Antimicrobial polyketides from the endophytic fungus Fusarium asiaticum QA-6 derived from medicinal plant Artemisia argyi","authors":"Xiao-Shan Shi , Sui-Qun Yang , Xiao-Ming Li , Yan-He Li , Dun-Jia Wang , Xin Li , Ling-Hong Meng , Xing-Wang Zhou , Bin-Gui Wang","doi":"10.1016/j.phytochem.2025.114379","DOIUrl":"10.1016/j.phytochem.2025.114379","url":null,"abstract":"<div><div>Seven previously undescribed polyketide derivatives, fusariumtides A–G (<strong>1</strong>–<strong>7</strong>), together with three known analogues (<strong>8</strong>–<strong>10</strong>), were isolated from the culture extract of <em>Fusarium asiaticum</em> QA-6, an endophytic fungus obtained from the fresh stem tissue of the medicinal plant <em>Artemisia argyi</em> H. Lev. & Vaniot. Their structures were elucidated by detailed interpretation of 1D/2D NMR spectroscopic and mass spectrometric data, and the absolute configuration of compound <strong>1</strong> was established on the basis of X-ray crystallographic analysis and ECD and specific rotation (SR) calculations. The isolated compounds, which possessed a functionalized decalin moiety, were evaluated for antimicrobial activities. Compounds <strong>1</strong> and <strong>10</strong> exhibited broad-spectrum inhibitory activities against nine tested pathogenic bacteria with MIC values ranging from 1 to 64 μg/mL, while compound <strong>8</strong> showed potent inhibitory activities against aquatic pathogens <em>Aeromonas hydrophilia</em>, <em>Pseudomonas aeruginosa</em>, <em>Vibrio harveyi</em>, and <em>V. vulnificus</em>, which were comparable to/or stronger than those of the positive control chloramphenicol.</div></div>","PeriodicalId":20170,"journal":{"name":"Phytochemistry","volume":"233 ","pages":"Article 114379"},"PeriodicalIF":3.2,"publicationDate":"2025-01-03","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"142927763","PeriodicalName":null,"FirstCategoryId":null,"ListUrlMain":null,"RegionNum":2,"RegionCategory":"生物学","ArticlePicture":[],"TitleCN":null,"AbstractTextCN":null,"PMCID":"","EPubDate":null,"PubModel":null,"JCR":null,"JCRName":null,"Score":null,"Total":0}
Pub Date : 2024-12-30DOI: 10.1016/j.phytochem.2024.114377
Mamdouh Nabil Samy , Eman Zekry Attia , Basmaa Ali Khalifa , Ahmed G. Darwish , Ahmed A. Al-Karmalawy , Radwan Alnajjar , Usama Ramadan Abdelmohsen , Mohamed Ali Ibrahim , Samir Anis Ross
Chemical investigation of the ethyl acetate extract of the endophytic fungus Aspergillus terreus AArEF2 found in the fresh leaves of Artemisia arborescens L. led to isolation of five previously undescribed butenolides, asperterreunolides A-E (1-5), along with the known metabolite butyrolactone IV (6). The structure elucidation of these metabolites was established by detailed spectroscopic analyses (1D, 2D NMR and HR-ESI-MS analyses). The absolute configuration of compounds 4 and 5 was determined using the modified Mosher's method. The isolated metabolites (1–6) were evaluated for their cytotoxic activity against A-431, C4–2B, and MDA PCa 2b cell lines by MTT assay using a 96-well microplate. The findings revealed that all the isolated compounds had notable cytotoxic properties with IC50 values ranging from 3.72 to 6.27 μmol/L. Moreover, molecular docking was applied to propose the mechanism of action for the potential antitumor activity of the five previously undescribed butenolides, asperterreunolides A-E (1–5), along with known metabolite butyrolactone IV (6) to be attributed to type IIA topoisomerase inhibition. Furthermore, molecular dynamic simulations were implemented for 200 ns to study the stability of the asperterreunolides A-E (1–5) and butyrolactone IV (6) inside the active site of the type IIA topoisomerase.
{"title":"Undescribed cytotoxic butenolides; asperterreunolides A-E, isolated from endophytic fungus Aspergillus terreus derived from Artemisia arborescens L. supported with in silico study","authors":"Mamdouh Nabil Samy , Eman Zekry Attia , Basmaa Ali Khalifa , Ahmed G. Darwish , Ahmed A. Al-Karmalawy , Radwan Alnajjar , Usama Ramadan Abdelmohsen , Mohamed Ali Ibrahim , Samir Anis Ross","doi":"10.1016/j.phytochem.2024.114377","DOIUrl":"10.1016/j.phytochem.2024.114377","url":null,"abstract":"<div><div>Chemical investigation of the ethyl acetate extract of the endophytic fungus <em>Aspergillus terreus</em> AArEF2 found in the fresh leaves of <em>Artemisia arborescens</em> L. led to isolation of five previously undescribed butenolides, asperterreunolides A-E (<strong>1-5</strong>), along with the known metabolite butyrolactone IV (<strong>6</strong>). The structure elucidation of these metabolites was established by detailed spectroscopic analyses (1D, 2D NMR and HR-ESI-MS analyses). The absolute configuration of compounds <strong>4</strong> and <strong>5</strong> was determined using the modified Mosher's method. The isolated metabolites (<strong>1</strong>–<strong>6</strong>) were evaluated for their cytotoxic activity against A-431, C4–2B, and MDA PCa 2b cell lines by MTT assay using a 96-well microplate. The findings revealed that all the isolated compounds had notable cytotoxic properties with IC<sub>50</sub> values ranging from 3.72 to 6.27 μmol/L. Moreover, molecular docking was applied to propose the mechanism of action for the potential antitumor activity of the five previously undescribed butenolides, asperterreunolides A-E (<strong>1</strong>–<strong>5</strong>), along with known metabolite butyrolactone IV (<strong>6</strong>) to be attributed to type IIA topoisomerase inhibition. Furthermore, molecular dynamic simulations were implemented for 200 ns to study the stability of the asperterreunolides A-E (<strong>1</strong>–<strong>5</strong>) and butyrolactone IV (<strong>6</strong>) inside the active site of the type IIA topoisomerase.</div></div>","PeriodicalId":20170,"journal":{"name":"Phytochemistry","volume":"232 ","pages":"Article 114377"},"PeriodicalIF":3.2,"publicationDate":"2024-12-30","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"142915285","PeriodicalName":null,"FirstCategoryId":null,"ListUrlMain":null,"RegionNum":2,"RegionCategory":"生物学","ArticlePicture":[],"TitleCN":null,"AbstractTextCN":null,"PMCID":"","EPubDate":null,"PubModel":null,"JCR":null,"JCRName":null,"Score":null,"Total":0}
Pub Date : 2024-12-27DOI: 10.1016/j.phytochem.2024.114375
Jin-Chang Huang , Xin-Yu Jia , Yi-Fan Lv , Hong-Hong Xu , Ming Han , Qiang-Qiang Yu , Yu-Ting Lu , Hong-Xun Yang , Yang Yang , Jing-Ya Li , Ai-Jun Hou
As a both edible and medicinal plant, Hypericum patulum (Hypericaceae) is used as a natural herbal tea, scented tea, and folk medicine. In this study, eight undescribed bicyclic polyprenylated acylphloroglucinol-related meroterpenoids named hyperpatins A–H, along with eight known ones, were isolated from this plant. Their structures were elucidated on the basis of spectroscopic techniques, chemical method, X-ray crystallographic experiments, and electronic circular dichroism analyses. Hyperpatins A–H possess a characteristic pyran ring system diversely fused with the bicyclo[3.3.1]nonane-2,4,9-trione core, and hyperpatins C and D incorporate a unique α,β-unsaturated aldehyde moiety. Some of the isolates exhibited potent inhibitory effects on death-associated protein kinase-related apoptosis-inducing kinase 2 with IC50 values ranging from 2.60 ± 0.29 to 17.93 ± 3.08 μM. This is the first report of DRAK2 inhibitory activity for acylphloroglucinol-related meroterpenoids. The most active molecule hyperpatins C showed binding affinity with DRAK2 by hydrogen-bond and hydrophobic interactions in molecular docking and promoted the glucose-stimulated insulin secretion ability of primary islets.
作为一种可食用和药用的植物，金丝桃（金丝桃科）被用作天然凉茶，花茶和民间药物。本研究从该植物中分离到8个未描述的双环聚戊烯基酰基间苯三酚相关的甲氧基萜类化合物，命名为hyperpatins A-H，以及8个已知的萜类化合物。通过光谱技术、化学方法、x射线晶体学实验和电子圆二色分析对其结构进行了分析。Hyperpatins a - h具有独特的吡喃环体系，与双环[3.3.1]壬烷-2,4,9-三酮核心多元融合，Hyperpatins C和D包含独特的α，β-不饱和醛部分。部分菌株对死亡相关蛋白激酶相关凋亡诱导激酶2有较强的抑制作用，IC50值为2.60±0.29 ~ 17.93±3.08 μM。这是首次报道DRAK2抑制酰基间苯三酚相关的巯基萜类化合物的活性。活性最强的分子hyperpatins C在分子对接中通过氢键和疏水相互作用与DRAK2结合，促进原代胰岛葡萄糖刺激的胰岛素分泌能力。
{"title":"Bicyclic polyprenylated acylphloroglucinol-related meroterpenoids as potent DRAK2 inhibitors from Hypericum patulum","authors":"Jin-Chang Huang , Xin-Yu Jia , Yi-Fan Lv , Hong-Hong Xu , Ming Han , Qiang-Qiang Yu , Yu-Ting Lu , Hong-Xun Yang , Yang Yang , Jing-Ya Li , Ai-Jun Hou","doi":"10.1016/j.phytochem.2024.114375","DOIUrl":"10.1016/j.phytochem.2024.114375","url":null,"abstract":"<div><div>As a both edible and medicinal plant, <em>Hypericum patulum</em> (Hypericaceae) is used as a natural herbal tea, scented tea, and folk medicine. In this study, eight undescribed bicyclic polyprenylated acylphloroglucinol-related meroterpenoids named hyperpatins A–H, along with eight known ones, were isolated from this plant. Their structures were elucidated on the basis of spectroscopic techniques, chemical method, X-ray crystallographic experiments, and electronic circular dichroism analyses. Hyperpatins A–H possess a characteristic pyran ring system diversely fused with the bicyclo[3.3.1]nonane-2,4,9-trione core, and hyperpatins C and D incorporate a unique <em>α</em>,<em>β</em>-unsaturated aldehyde moiety. Some of the isolates exhibited potent inhibitory effects on death-associated protein kinase-related apoptosis-inducing kinase 2 with IC<sub>50</sub> values ranging from 2.60 ± 0.29 to 17.93 ± 3.08 μM. This is the first report of DRAK2 inhibitory activity for acylphloroglucinol-related meroterpenoids. The most active molecule hyperpatins C showed binding affinity with DRAK2 by hydrogen-bond and hydrophobic interactions in molecular docking and promoted the glucose-stimulated insulin secretion ability of primary islets.</div></div>","PeriodicalId":20170,"journal":{"name":"Phytochemistry","volume":"232 ","pages":"Article 114375"},"PeriodicalIF":3.2,"publicationDate":"2024-12-27","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"142903440","PeriodicalName":null,"FirstCategoryId":null,"ListUrlMain":null,"RegionNum":2,"RegionCategory":"生物学","ArticlePicture":[],"TitleCN":null,"AbstractTextCN":null,"PMCID":"","EPubDate":null,"PubModel":null,"JCR":null,"JCRName":null,"Score":null,"Total":0}
Pub Date : 2024-12-24DOI: 10.1016/j.phytochem.2024.114372
Gui-Min Xue , Jin-Feng Xue , Hao Pan , Hao Feng , Jing-Wei Lei , Hui Chen , Wei-Sheng Feng , Guo-Sheng Li , Yan Wang
Five phenylpropanoid dimers chrysanthephenyls A−E, with the 1-O-1′-type (1) and 1-O-2′-type (2−5) ether bond linking modes, were isolated from the aerial parts of Chrysanthemum indicum. Among them, chrysanthephenyls D and E were two pairs of enantiomers, and chrysanthephenyl E was further resolved into its enantiomers (+)-chrysanthephenyl E and (−)-chrysanthephenyl E via chiral-phase HPLC. Their structures were characterized on the basic analysis of the spectroscopic techniques (IR, HRESIMS, 1D and 2D NMR), and their absolute configurations were determined by DP4+ NMR analysis and ECD calculation method. The antioxidant activity of chrysanthephenyls A−E was determined by measuring their free radical scavenging effects using the trolox equivalent antioxidant activity (TEAC) assay, and chrysanthephenyls D and E showed 17 and 15 times better activity respectively than that of the positive control trolox. Moreover, a mechanistic study revealed that the potential antioxidant activity of chrysanthephenyl D decreased the level of reactive oxygen species (ROS) mediated via activating nuclear factor E2-related factor 2 (Nrf2) and its downstream oxidases.
从菊花的地上部分分离到5个苯丙类二聚体菊苯A-E，它们具有1- o -1‘型(1)和1- o -2’型（2-5）醚键连接模式。其中，菊花苯基D和E为两对对映体，菊花苯基E通过手性相高效液相色谱进一步分解为对映体(+)-菊花苯基E和(-)-菊花苯基E。通过基本的光谱技术（IR、hresms、1D和2D NMR）对它们的结构进行了表征，并通过DP4+ NMR分析和ECD计算方法确定了它们的绝对构型。采用trolox等效抗氧化活性（TEAC）法测定了菊花酚A-E的抗氧化活性，结果表明，菊花酚D和E的抗氧化活性分别比阳性对照trolox强17倍和15倍。此外，一项机制研究表明，菊花苯基D的潜在抗氧化活性降低了通过激活核因子e2相关因子2 （Nrf2）及其下游氧化酶介导的活性氧（ROS）水平。
{"title":"Phenylpropanoid dimers from Chrysanthemum indicum with antioxidant effects via activating the Nrf2 signaling pathway","authors":"Gui-Min Xue , Jin-Feng Xue , Hao Pan , Hao Feng , Jing-Wei Lei , Hui Chen , Wei-Sheng Feng , Guo-Sheng Li , Yan Wang","doi":"10.1016/j.phytochem.2024.114372","DOIUrl":"10.1016/j.phytochem.2024.114372","url":null,"abstract":"<div><div>Five phenylpropanoid dimers chrysanthephenyls A−E, with the 1-<em>O</em>-1′-type (<strong>1</strong>) and 1-<em>O</em>-2′-type (<strong>2</strong>−<strong>5</strong>) ether bond linking modes, were isolated from the aerial parts of <em>Chrysanthemum indicum</em>. Among them, chrysanthephenyls D and E were two pairs of enantiomers, and chrysanthephenyl E was further resolved into its enantiomers (+)-chrysanthephenyl E and (−)-chrysanthephenyl E via chiral-phase HPLC. Their structures were characterized on the basic analysis of the spectroscopic techniques (IR, HRESIMS, 1D and 2D NMR), and their absolute configurations were determined by DP4+ NMR analysis and ECD calculation method. The antioxidant activity of chrysanthephenyls A−E was determined by measuring their free radical scavenging effects using the trolox equivalent antioxidant activity (TEAC) assay, and chrysanthephenyls D and E showed 17 and 15 times better activity respectively than that of the positive control trolox. Moreover, a mechanistic study revealed that the potential antioxidant activity of chrysanthephenyl D decreased the level of reactive oxygen species (ROS) mediated via activating nuclear factor E2-related factor 2 (Nrf2) and its downstream oxidases.</div></div>","PeriodicalId":20170,"journal":{"name":"Phytochemistry","volume":"232 ","pages":"Article 114372"},"PeriodicalIF":3.2,"publicationDate":"2024-12-24","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"142896706","PeriodicalName":null,"FirstCategoryId":null,"ListUrlMain":null,"RegionNum":2,"RegionCategory":"生物学","ArticlePicture":[],"TitleCN":null,"AbstractTextCN":null,"PMCID":"","EPubDate":null,"PubModel":null,"JCR":null,"JCRName":null,"Score":null,"Total":0}
Pub Date : 2024-12-20DOI: 10.1016/j.phytochem.2024.114371
Jianjin Guo , Shan-Shan Zhang , Jing Gao , Yan Guo , Chi-Tang Ho , Naisheng Bai
Fraxinus L., a member of the Oleaceae family with approximately 60 species worldwide, is widely distributed in the warm temperate zone of the northern hemisphere. It is not only used as a folk medicine for treating various illnesses but is also documented in medical books. The traditional Chinese medicine "Qin Pi" originated from this genus and is known for its efficacy in treating conditions such as intestinal inflammation, redness and pain in the eyes, abomination of redness and leucorrhoea, and bacterial infections. This paper aims to fill the gap in the existing literature by providing a comprehensive review and critical analysis of the Fraxinus genus plant. The discussion in this paper covers various aspects of the plant, including its botany, traditional and modern applications, phytochemistry, bioactivity, role in ecosystems, phytogenetic evolution, economic benefits, and future challenges. By synthesizing this information, the review aims to offer valuable insights for the advancement, utilization, and further research of the Fraxinus spp.. Phytochemical studies have identified a total of 281 chemical constituents in Fraxinus spp., including secoiridoids, coumarins, and flavonoids. These Fraxinus spp. plants exhibit a wide range of biological activities, such as anti-inflammatory, antioxidant, and antibacterial properties. Furthermore, this paper delves into potential research directions within the genus and addresses the challenges associated with achieving a comprehensive understanding of Fraxinus spp. This paper provides a comprehensive overview of Fraxinus spp., highlighting their bioactivity mechanism and the opportunity to facilitate the advancement of new pharmaceuticals.
{"title":"The genus Fraxinus L. (Oleaceae): A review of botany, traditional and modern applications, phytochemistry, and bioactivity","authors":"Jianjin Guo , Shan-Shan Zhang , Jing Gao , Yan Guo , Chi-Tang Ho , Naisheng Bai","doi":"10.1016/j.phytochem.2024.114371","DOIUrl":"10.1016/j.phytochem.2024.114371","url":null,"abstract":"<div><div><em>Fraxinus L</em>., a member of the Oleaceae family with approximately 60 species worldwide, is widely distributed in the warm temperate zone of the northern hemisphere. It is not only used as a folk medicine for treating various illnesses but is also documented in medical books. The traditional Chinese medicine \"Qin Pi\" originated from this genus and is known for its efficacy in treating conditions such as intestinal inflammation, redness and pain in the eyes, abomination of redness and leucorrhoea, and bacterial infections. This paper aims to fill the gap in the existing literature by providing a comprehensive review and critical analysis of the <em>Fraxinus</em> genus plant. The discussion in this paper covers various aspects of the plant, including its botany, traditional and modern applications, phytochemistry, bioactivity, role in ecosystems, phytogenetic evolution, economic benefits, and future challenges. By synthesizing this information, the review aims to offer valuable insights for the advancement, utilization, and further research of the <em>Fraxinus</em> spp.. Phytochemical studies have identified a total of 281 chemical constituents in <em>Fraxinus</em> spp., including secoiridoids, coumarins, and flavonoids. These <em>Fraxinus</em> spp. plants exhibit a wide range of biological activities, such as anti-inflammatory, antioxidant, and antibacterial properties. Furthermore, this paper delves into potential research directions within the genus and addresses the challenges associated with achieving a comprehensive understanding of <em>Fraxinus</em> spp. This paper provides a comprehensive overview of <em>Fraxinus</em> spp., highlighting their bioactivity mechanism and the opportunity to facilitate the advancement of new pharmaceuticals.</div></div>","PeriodicalId":20170,"journal":{"name":"Phytochemistry","volume":"232 ","pages":"Article 114371"},"PeriodicalIF":3.2,"publicationDate":"2024-12-20","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"142877815","PeriodicalName":null,"FirstCategoryId":null,"ListUrlMain":null,"RegionNum":2,"RegionCategory":"生物学","ArticlePicture":[],"TitleCN":null,"AbstractTextCN":null,"PMCID":"","EPubDate":null,"PubModel":null,"JCR":null,"JCRName":null,"Score":null,"Total":0}
Pub Date : 2024-12-19DOI: 10.1016/j.phytochem.2024.114364
Hai-Yin Wang , Yu Shen , Wei Nie , Wen-Chao Tu , Suling Huang , Xing-De Wu
Fibraurea recisa Pierre is a vine plant and its vine stems are used as a traditional Chinese medicine to treat heat toxin, constipation, diarrhea, sore throat, eye inflammation, carbuncles, and skin ulcers. The alkaloid chemical composition of this plant has been extensively studied; however, investigations into non-alkaloid components remain limited. In this study, phytochemical studies of the vine stems of F. recisa were conducted, leading to the isolation and identification of twenty highly oxidized clerodane diterpenoids, including ten previously undescribed compounds, designated fibrecins A-J (1–10). The structures and absolute configurations of 1–10 were determined through comprehensive spectroscopic methods (IR, HRESIMS, 1D and 2D NMR), electronic circular dichroism data, and single-crystal X-ray diffraction. Notably, compounds 1 and 2 are rare 18-nor-clerodane diterpenoids. Excessive hepatic gluconeogenesis is an important cause of hyperglycemia and type 2 diabetes mellitus. Herein, compounds 1, 9, 14, and 15 were found to exhibit moderate hepatic gluconeogenesis inhibitory activity in primary mouse hepatocytes, suggesting that these compounds might have potential effect on ameliorating the hyperglycaemia.
{"title":"Clerodane diterpenoids from the vine stems of Fibraurea recisa Pierre and their hepatic gluconeogenesis inhibitory activity","authors":"Hai-Yin Wang , Yu Shen , Wei Nie , Wen-Chao Tu , Suling Huang , Xing-De Wu","doi":"10.1016/j.phytochem.2024.114364","DOIUrl":"10.1016/j.phytochem.2024.114364","url":null,"abstract":"<div><div><em>Fibraurea recisa</em> Pierre is a vine plant and its vine stems are used as a traditional Chinese medicine to treat heat toxin, constipation, diarrhea, sore throat, eye inflammation, carbuncles, and skin ulcers. The alkaloid chemical composition of this plant has been extensively studied; however, investigations into non-alkaloid components remain limited. In this study, phytochemical studies of the vine stems of <em>F</em>. <em>recisa</em> were conducted, leading to the isolation and identification of twenty highly oxidized clerodane diterpenoids, including ten previously undescribed compounds, designated fibrecins A-J (<strong>1</strong>–<strong>10</strong>). The structures and absolute configurations of <strong>1</strong>–<strong>10</strong> were determined through comprehensive spectroscopic methods (IR, HRESIMS, 1D and 2D NMR), electronic circular dichroism data, and single-crystal X-ray diffraction. Notably, compounds <strong>1</strong> and <strong>2</strong> are rare 18-nor-clerodane diterpenoids. Excessive hepatic gluconeogenesis is an important cause of hyperglycemia and type 2 diabetes mellitus. Herein, compounds <strong>1</strong>, <strong>9</strong>, <strong>14</strong>, and <strong>15</strong> were found to exhibit moderate hepatic gluconeogenesis inhibitory activity in primary mouse hepatocytes, suggesting that these compounds might have potential effect on ameliorating the hyperglycaemia.</div></div>","PeriodicalId":20170,"journal":{"name":"Phytochemistry","volume":"232 ","pages":"Article 114364"},"PeriodicalIF":3.2,"publicationDate":"2024-12-19","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"142872229","PeriodicalName":null,"FirstCategoryId":null,"ListUrlMain":null,"RegionNum":2,"RegionCategory":"生物学","ArticlePicture":[],"TitleCN":null,"AbstractTextCN":null,"PMCID":"","EPubDate":null,"PubModel":null,"JCR":null,"JCRName":null,"Score":null,"Total":0}
Pub Date : 2024-12-19DOI: 10.1016/j.phytochem.2024.114374
Yuan Wang , Tian-Ze Li , Yun-Bao Ma , Chang-An Geng , Yong Cui Wang , Ji-Jun Chen
Two unprecedented sesquiterpene and monoterpene heterodimers and ten previously undescribed sesquiterpenoids, artemordosins A−L (1−12), as well as ten known sesquiterpenoids (13−22), were obtained from Artemisia ordosica. Their structures were elucidated based on comprehensive analyses of NMR, IR, HRESIMS, GIAO NMR calculations with DP4+ probability analysis, and ECD calculations. Notably, artemordosins A and B (1 and 2) were the first examples of cadinane–monoterpene dimers, and artemordosin A (1) was a cadinane–myrceane heterodimer with a 6/6/6/6 ring system formed by [4 + 2] cycloaddition, while artemordosin B (2) was a 4,5-seco-cadinane-artemisane dimer connected through a C-5−O–C-4′ linkage. Artemordosin C (3) was the first example of 10(5 → 4)-abeo-eudesmane sesquiterpenoid featuring an unprecedented bicyclo[5.3.0]decane skeleton in natural products. Artemordosin B (2) and epi-deoxyarteannuin B (14) showed inhibitory activity on three hepatoma cells with IC50 values of 37.1 and 15.4 μM (HepG2), 27.7 and 16.4 μM (Huh-7), 39.6 and 22.6 μM (SK-Hep-1).
{"title":"Artemordosins A−L, cadinane-monoterpene heterodimers and sesquiterpenoids with antihepatoma activity from Artemisia ordosica","authors":"Yuan Wang , Tian-Ze Li , Yun-Bao Ma , Chang-An Geng , Yong Cui Wang , Ji-Jun Chen","doi":"10.1016/j.phytochem.2024.114374","DOIUrl":"10.1016/j.phytochem.2024.114374","url":null,"abstract":"<div><div>Two unprecedented sesquiterpene and monoterpene heterodimers and ten previously undescribed sesquiterpenoids, artemordosins A−L (<strong>1</strong>−<strong>12</strong>), as well as ten known sesquiterpenoids (<strong>13</strong>−<strong>22</strong>), were obtained from <em>Artemisia ordosica</em>. Their structures were elucidated based on comprehensive analyses of NMR, IR, HRESIMS, GIAO NMR calculations with DP4+ probability analysis, and ECD calculations. Notably, artemordosins A and B (<strong>1</strong> and <strong>2</strong>) were the first examples of cadinane–monoterpene dimers, and artemordosin A (<strong>1</strong>) was a cadinane–myrceane heterodimer with a 6/6/6/6 ring system formed by [4 + 2] cycloaddition, while artemordosin B (<strong>2</strong>) was a 4,5-<em>seco</em>-cadinane-artemisane dimer connected through a C-5−O–C-4′ linkage. Artemordosin C (<strong>3</strong>) was the first example of 10(5 → 4)-<em>abeo</em>-eudesmane sesquiterpenoid featuring an unprecedented bicyclo[5.3.0]decane skeleton in natural products. Artemordosin B (<strong>2</strong>) and <em>epi</em>-deoxyarteannuin B (<strong>14)</strong> showed inhibitory activity on three hepatoma cells with IC<sub>50</sub> values of 37.1 and 15.4 μM (HepG2), 27.7 and 16.4 μM (Huh-7), 39.6 and 22.6 μM (SK-Hep-1).</div></div>","PeriodicalId":20170,"journal":{"name":"Phytochemistry","volume":"232 ","pages":"Article 114374"},"PeriodicalIF":3.2,"publicationDate":"2024-12-19","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"142872172","PeriodicalName":null,"FirstCategoryId":null,"ListUrlMain":null,"RegionNum":2,"RegionCategory":"生物学","ArticlePicture":[],"TitleCN":null,"AbstractTextCN":null,"PMCID":"","EPubDate":null,"PubModel":null,"JCR":null,"JCRName":null,"Score":null,"Total":0}
Pub Date : 2024-12-19DOI: 10.1016/j.phytochem.2024.114373
Song Wang , De-Zhi Wang , Xia Zhang , Zi-Wei Li , Dong-Hao Lu , Zheng-Jin Jiang , Min Ma , Min Song , Xiao-Qi Zhang
Eleven undescribed piperidine alkaloids, arecachines A‒J (1–11), were isolated from the peels of Areca catechu. Compounds 8–11 are featured as bis-piperidine alkaloids. Their structures were elucidated by analysis of UV, IR, HRESIMS, 1D and 2D NMR spectra. Compounds 1–4, 6, and 8–11 were evaluated for the monoamine oxidases (MAOs) inhibitory activity. Among them, compounds 3, 4, 6, and 10 showed MAOA inhibitory activity with IC50 values of 7.85–55.96 μM, while compounds 1–4, 8, 10, and 11 showed MAOB inhibitory activity with IC50 values of 11.92–77.87 μM.
{"title":"Piperidine and bis-piperidine alkaloids from the peels of Areca catechu and their monoamine oxidases inhibitory activity","authors":"Song Wang , De-Zhi Wang , Xia Zhang , Zi-Wei Li , Dong-Hao Lu , Zheng-Jin Jiang , Min Ma , Min Song , Xiao-Qi Zhang","doi":"10.1016/j.phytochem.2024.114373","DOIUrl":"10.1016/j.phytochem.2024.114373","url":null,"abstract":"<div><div>Eleven undescribed piperidine alkaloids, arecachines A‒J (<strong>1</strong>–<strong>11</strong>), were isolated from the peels of <em>Areca catechu</em>. Compounds <strong>8</strong>–<strong>11</strong> are featured as bis-piperidine alkaloids. Their structures were elucidated by analysis of UV, IR, HRESIMS, 1D and 2D NMR spectra. Compounds <strong>1</strong>–<strong>4</strong>, <strong>6</strong>, and <strong>8</strong>–<strong>11</strong> were evaluated for the monoamine oxidases (MAOs) inhibitory activity. Among them, compounds <strong>3</strong>, <strong>4</strong>, <strong>6</strong>, and <strong>10</strong> showed MAOA inhibitory activity with IC<sub>50</sub> values of 7.85–55.96 μM, while compounds <strong>1</strong>–<strong>4</strong>, <strong>8</strong>, <strong>10</strong>, and <strong>11</strong> showed MAOB inhibitory activity with IC<sub>50</sub> values of 11.92–77.87 μM.</div></div>","PeriodicalId":20170,"journal":{"name":"Phytochemistry","volume":"232 ","pages":"Article 114373"},"PeriodicalIF":3.2,"publicationDate":"2024-12-19","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"142872392","PeriodicalName":null,"FirstCategoryId":null,"ListUrlMain":null,"RegionNum":2,"RegionCategory":"生物学","ArticlePicture":[],"TitleCN":null,"AbstractTextCN":null,"PMCID":"","EPubDate":null,"PubModel":null,"JCR":null,"JCRName":null,"Score":null,"Total":0}
Pub Date : 2024-12-18DOI: 10.1016/j.phytochem.2024.114370
Ding-Xun Wu , Jue Yang , Li-Hua Chen , Shuang-Yu Xu , Jun Jin , Ya-Nan Li , Xiao-Jiang Hao , Chun-Mao Yuan
Six previously undescribed sesquiterpenes, magnogranoides A–F (1–6), along with 10 known terpenes, were isolated from the leaves of Magnolia grandiflora L. Six previously undescribed sesquiterpene derivatives (11a–11e and 14a) were synthesized using chemical methods. Those structures were identified through extensive spectroscopic data and quantum chemical calculations. Notably, compound 1 represents the first sesquiterpene with a previously undescribed 8/5/5 tricyclic ring, and compound 2 was elucidated to be the first 13-norguaiane-type sesquiterpenoid with a 5/7/5 tricyclic ring system. Four compounds (3, 7, 8, and 16) exhibited better anti-neuroinflammatory activities in BV-2 cells with IC50 values ranging from 3.23 ± 0.23 μM to 15.98 ± 1.79 μM than the positive control, minocycline (IC50: 20.56 ± 0.93). Furthermore, the chemotaxonomic significance of the isolates was also discussed.
{"title":"Anti-neuroinflammatory terpenes from Magnolia grandiflora","authors":"Ding-Xun Wu , Jue Yang , Li-Hua Chen , Shuang-Yu Xu , Jun Jin , Ya-Nan Li , Xiao-Jiang Hao , Chun-Mao Yuan","doi":"10.1016/j.phytochem.2024.114370","DOIUrl":"10.1016/j.phytochem.2024.114370","url":null,"abstract":"<div><div>Six previously undescribed sesquiterpenes, magnogranoides A–F (<strong>1</strong>–<strong>6</strong>), along with 10 known terpenes, were isolated from the leaves of <em>Magnolia grandiflora</em> L. Six previously undescribed sesquiterpene derivatives (<strong>11a</strong>–<strong>11e</strong> and <strong>14a</strong>) were synthesized using chemical methods. Those structures were identified through extensive spectroscopic data and quantum chemical calculations. Notably, compound <strong>1</strong> represents the first sesquiterpene with a previously undescribed 8/5/5 tricyclic ring, and compound <strong>2</strong> was elucidated to be the first 13-norguaiane-type sesquiterpenoid with a 5/7/5 tricyclic ring system. Four compounds (<strong>3</strong>, <strong>7</strong>, <strong>8</strong>, and <strong>16</strong>) exhibited better anti-neuroinflammatory activities in BV-2 cells with IC<sub>50</sub> values ranging from 3.23 ± 0.23 μM to 15.98 ± 1.79 μM than the positive control, minocycline (IC<sub>50</sub>: 20.56 ± 0.93). Furthermore, the chemotaxonomic significance of the isolates was also discussed.</div></div>","PeriodicalId":20170,"journal":{"name":"Phytochemistry","volume":"232 ","pages":"Article 114370"},"PeriodicalIF":3.2,"publicationDate":"2024-12-18","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"142872044","PeriodicalName":null,"FirstCategoryId":null,"ListUrlMain":null,"RegionNum":2,"RegionCategory":"生物学","ArticlePicture":[],"TitleCN":null,"AbstractTextCN":null,"PMCID":"","EPubDate":null,"PubModel":null,"JCR":null,"JCRName":null,"Score":null,"Total":0}
Pub Date : 2024-12-18DOI: 10.1016/j.phytochem.2024.114369
Yu-Peng Li , Ying Li , Wen-Jing Gao , Chu-Hong Fang , Ming-Jun Lv , Jian-Min Yue , Jin-Hai Yu
A phytochemical investigation into the plants of Euphorbia esula L. has yielded 19 diterpenoids, comprising 17 jatrophane-type (1−7 and 9−18) and two ingenane-type (8 and 19). The structures of these compounds were elucidated by a combination of spectrum elucidations, quantum chemical calculations, and X-ray single crystal diffraction. Biological evaluations demonstrated that compounds 6, 8, 18, and 19 show significant anti-inflammatory activity with IC50 values within 10 μM, without displaying any morphological signs of cytotoxicity. Further biological analysis revealed that euphoresulin A (8) is involved in the suppression of inflammatory response by blocking the activation of NF-κB/MAPK and activating Nrf2/HO-1 singling pathways.
{"title":"Jatrophane and ingenane diterpenoids with anti-inflammatory activity from Euphorbia esula","authors":"Yu-Peng Li , Ying Li , Wen-Jing Gao , Chu-Hong Fang , Ming-Jun Lv , Jian-Min Yue , Jin-Hai Yu","doi":"10.1016/j.phytochem.2024.114369","DOIUrl":"10.1016/j.phytochem.2024.114369","url":null,"abstract":"<div><div>A phytochemical investigation into the plants of <em>Euphorbia esula</em> L. has yielded 19 diterpenoids, comprising 17 jatrophane-type (<strong>1</strong>−<strong>7</strong> and <strong>9</strong>−<strong>18</strong>) and two ingenane-type (<strong>8</strong> and <strong>19</strong>). The structures of these compounds were elucidated by a combination of spectrum elucidations, quantum chemical calculations, and X-ray single crystal diffraction. Biological evaluations demonstrated that compounds <strong>6</strong>, <strong>8</strong>, <strong>18</strong>, and <strong>19</strong> show significant anti-inflammatory activity with IC<sub>50</sub> values within 10 μM, without displaying any morphological signs of cytotoxicity. Further biological analysis revealed that euphoresulin A (<strong>8</strong>) is involved in the suppression of inflammatory response by blocking the activation of NF-κB/MAPK and activating Nrf2/HO-1 singling pathways.</div></div>","PeriodicalId":20170,"journal":{"name":"Phytochemistry","volume":"232 ","pages":"Article 114369"},"PeriodicalIF":3.2,"publicationDate":"2024-12-18","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"142872365","PeriodicalName":null,"FirstCategoryId":null,"ListUrlMain":null,"RegionNum":2,"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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