Pub Date : 2025-01-15DOI: 10.1016/j.phytochem.2025.114404
Xiaoqian Ding , Yuxuan Qiu , Shuang Yao , Wenshuai Bao , Xiachang Wang , Qi Lv , Leilei Gao , Yiwen Chu , Yinan Zhang , Yang Hu
On the basis of the co-culture strategy, five previously undescribed S-bridged pyranonaphthoquinones, crepidamycins A–E (1–5) and five known analogues (6–10) were isolated from a medicinal plant endophytic Streptomyces sp. MG-F-1 in Dendrobium crepidatum with Bacillus cereus MG-1. The structures and absolute configurations of 1–5 were elucidated by the interpretation of data from detailed spectroscopic analysis and electronic circular dichroism spectra, together with consideration of the biogenetic origins. Interestingly, these previously undescribed compounds were only found in the co-cultures and absent from the pure culture controls. Compounds 1–10 were assayed for their anti-inflammatory potential using LPS-stimulated RAW264.7 cells, of which compound 4 showed strong nitric oxide inhibitory effect with an IC50 of 0.22 ± 0.16 μM. The results of extracellular acidification rate and molecular docking suggest that it may play a role by regulating PKM2-mediated glycolysis.
在共培养策略的基础上，从石斛内生真菌Streptomyces sp. MG-F-1和蜡样芽孢杆菌MG-1中分离出5个先前未被描述的s桥联吡萘醌、crepidamyins a - e（1-5）和5个已知的类似物（6-10）。通过详细的光谱分析和电子圆二色光谱数据的解释，并考虑生物成因，阐明了1-5的结构和绝对构型。有趣的是，这些先前未描述的化合物仅在共培养中发现，而在纯培养对照中不存在。利用lps刺激RAW264.7细胞检测化合物1 ~ 10的抗炎活性，其中化合物4表现出较强的一氧化氮抑制作用，IC50为0.22±0.16 μM。细胞外酸化速率和分子对接结果提示其可能通过调节pkm2介导的糖酵解发挥作用。
{"title":"Crepidamycins A–E, pyranonaphthoquinones from endophytic Streptomyces sp. MG-F-1 of Dendrobium crepidatum by the co-culture strategy","authors":"Xiaoqian Ding , Yuxuan Qiu , Shuang Yao , Wenshuai Bao , Xiachang Wang , Qi Lv , Leilei Gao , Yiwen Chu , Yinan Zhang , Yang Hu","doi":"10.1016/j.phytochem.2025.114404","DOIUrl":"10.1016/j.phytochem.2025.114404","url":null,"abstract":"<div><div>On the basis of the co-culture strategy, five previously undescribed <em>S</em>-bridged pyranonaphthoquinones, crepidamycins A–E (<strong>1</strong>–<strong>5</strong>) and five known analogues (<strong>6</strong>–<strong>10</strong>) were isolated from a medicinal plant endophytic <em>Streptomyces</em> sp. MG-F-1 in <em>Dendrobium crepidatum</em> with <em>Bacillus cereus</em> MG-1. The structures and absolute configurations of <strong>1</strong>–<strong>5</strong> were elucidated by the interpretation of data from detailed spectroscopic analysis and electronic circular dichroism spectra, together with consideration of the biogenetic origins. Interestingly, these previously undescribed compounds were only found in the co-cultures and absent from the pure culture controls. Compounds <strong>1</strong>–<strong>10</strong> were assayed for their anti-inflammatory potential using LPS-stimulated RAW264.7 cells, of which compound 4 showed strong nitric oxide inhibitory effect with an IC<sub>50</sub> of 0.22 ± 0.16 μM. The results of extracellular acidification rate and molecular docking suggest that it may play a role by regulating PKM2-mediated glycolysis.</div></div>","PeriodicalId":20170,"journal":{"name":"Phytochemistry","volume":"233 ","pages":"Article 114404"},"PeriodicalIF":3.2,"publicationDate":"2025-01-15","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"143009709","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 : 2025-01-13DOI: 10.1016/j.phytochem.2024.114376
Kang Ding , Xuege Pan , Weifeng Yin , Lin Li , Hongjin Bai , Maoli Bai , Jiekun Xu , Jun He , Weiku Zhang
Daphnane diterpenoids, as one of the representative types of diterpenoid compounds with rich structural diversity and significant biological activities, have an uncommon 5/7/6 tricyclic skeleton mainly found in species of Thymelaeaceae and Euphorbiaceae families. Due to the unique peculiarity of the framework and remarkable pharmacological activities, over the past three decades, novel structures have been continuously discovered and more structural subtypes have been derived. However, there is always a lack of a unified and convincing structural classification strategy for the summary of daphnane diterpenoids, which affects the in-depth and systematic research of pharmaceutical chemists and pharmacologists. In addition, the distinctive skeleton, continuous chiral centers, and prominent bioactivities of daphnane diterpenoids have attracted widespread interest among synthetic chemists. However, there are currently only a few reports of complete synthesis of compounds with low overall yields. Given the broad attention paid to daphnane diterpenoids in recent years, this review summarized the sources, structural classification, biological activities, and synthesis of around 300 natural daphnane diterpenoids discovered from 1993 to 2023, providing a reference for further discovery of novel structures, chemical and biological synthesis, and drug research.
{"title":"Natural promising daphnane diterpenoids: An integrated review of their sources, structural classification, biological activities, and synthesis","authors":"Kang Ding , Xuege Pan , Weifeng Yin , Lin Li , Hongjin Bai , Maoli Bai , Jiekun Xu , Jun He , Weiku Zhang","doi":"10.1016/j.phytochem.2024.114376","DOIUrl":"10.1016/j.phytochem.2024.114376","url":null,"abstract":"<div><div>Daphnane diterpenoids, as one of the representative types of diterpenoid compounds with rich structural diversity and significant biological activities, have an uncommon 5/7/6 tricyclic skeleton mainly found in species of Thymelaeaceae and Euphorbiaceae families. Due to the unique peculiarity of the framework and remarkable pharmacological activities, over the past three decades, novel structures have been continuously discovered and more structural subtypes have been derived. However, there is always a lack of a unified and convincing structural classification strategy for the summary of daphnane diterpenoids, which affects the in-depth and systematic research of pharmaceutical chemists and pharmacologists. In addition, the distinctive skeleton, continuous chiral centers, and prominent bioactivities of daphnane diterpenoids have attracted widespread interest among synthetic chemists. However, there are currently only a few reports of complete synthesis of compounds with low overall yields. Given the broad attention paid to daphnane diterpenoids in recent years, this review summarized the sources, structural classification, biological activities, and synthesis of around 300 natural daphnane diterpenoids discovered from 1993 to 2023, providing a reference for further discovery of novel structures, chemical and biological synthesis, and drug research.</div></div>","PeriodicalId":20170,"journal":{"name":"Phytochemistry","volume":"233 ","pages":"Article 114376"},"PeriodicalIF":3.2,"publicationDate":"2025-01-13","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"143009747","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}
From the tuber of Alisma orientale (Sam.) Juzep. (Alismataceae), twenty-four compounds were isolated, including six (1, 2, 3, 10, 14, and 17) that were not yet characterized. Spectroscopic investigations (IR, UV, HRESIMS, and NMR) were used to clarify their structures, and the ECD spectra of two compounds (8 and 9) were interpreted to identify their absolute configurations. Through an apoptotic signaling pathway, compounds 7, 15, 17, and 19 decreased the level of apoptosis in lung epithelial cells, indicating that they may have potential anti-pulmonary fibrosis (anti-PF) activity.
{"title":"Alkaloids and lignans isolated from Alisma orientale exhibit anti-pulmonary fibrosis activities by modulating an apoptotic signaling pathway","authors":"Deng-Hui Zhu , Jing-Ke Zhang , Peng-Li Guo , Si-Qi Tao , Meng-Nan Zeng , Xiao-Ke Zheng , Wei-Sheng Feng","doi":"10.1016/j.phytochem.2025.114382","DOIUrl":"10.1016/j.phytochem.2025.114382","url":null,"abstract":"<div><div>From the tuber of <em>Alisma orientale</em> (Sam.) Juzep. (<em>Alismataceae</em>), twenty-four compounds were isolated, including six (<strong>1</strong>, <strong>2</strong>, <strong>3</strong>, <strong>10</strong>, <strong>14</strong>, and <strong>17</strong>) that were not yet characterized. Spectroscopic investigations (IR, UV, HRESIMS, and NMR) were used to clarify their structures, and the ECD spectra of two compounds (<strong>8</strong> and <strong>9</strong>) were interpreted to identify their absolute configurations. Through an apoptotic signaling pathway, compounds <strong>7</strong>, <strong>15</strong>, <strong>17</strong>, and <strong>19</strong> decreased the level of apoptosis in lung epithelial cells, indicating that they may have potential anti-pulmonary fibrosis (anti-PF) activity.</div></div>","PeriodicalId":20170,"journal":{"name":"Phytochemistry","volume":"233 ","pages":"Article 114382"},"PeriodicalIF":3.2,"publicationDate":"2025-01-04","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"142953109","PeriodicalName":null,"FirstCategoryId":null,"ListUrlMain":null,"RegionNum":2,"RegionCategory":"生物学","ArticlePicture":[],"TitleCN":null,"AbstractTextCN":null,"PMCID":"OA","EPubDate":null,"PubModel":null,"JCR":null,"JCRName":null,"Score":null,"Total":0}
Forty-two Amaryllidaceae alkaloids, including eleven previously undescribed alkaloids, crinasiaticines C–M, and three undescribed naturally occurring alkaloids, (+)-dihydroepivittatine, (+)-dihydrovittatine and (+)-dihydrohamayne, were isolated from the leaves of Crinum asiaticum L. var. asiaticum. Their structures and configurations were elucidated using NMR and MS spectroscopic techniques, along with the comparison of experimental electronic circular dichroism spectra to calculated data. The anti-inflammatory activity against nitric oxide (NO) production in lipopolysaccharide-stimulated RAW264.7 cells was evaluated for most of the isolated alkaloids. Compounds 39, 21, 22, and 35 exhibited considerable NO inhibitory activity, with IC50 values of 2.5–2.6 μM, compared to positive control dexamethasone (IC50 2.7 μM). However, these compounds demonstrated cytotoxic effects on cells. Compound 15 also possessed the highest selectivity index of 22.5 with minimal cytotoxicity.
从asiatium L. var. asiatium的叶中分离得到42种Amaryllidaceae生物碱，包括11种未被描述的crinasiaticines C-M和3种未被描述的天然生物碱(+)-二氢维塔碱、(+)-二氢维塔碱和(+)-二氢维塔碱。利用核磁共振和质谱技术分析了它们的结构和构型，并将实验电子圆二色光谱与计算数据进行了比较。大多数分离的生物碱对脂多糖刺激RAW264.7细胞一氧化氮（NO）产生的抗炎活性进行了评价。化合物39、21、22和35与阳性对照地塞米松（IC50为2.7 μM）相比，具有明显的NO抑制活性，IC50值为2.5 ~ 2.6 μM。然而，这些化合物对细胞有细胞毒性作用。化合物15具有最高的选择性指数（22.5）和最小的细胞毒性。
{"title":"Amaryllidaceae alkaloids with nitric oxide inhibitory activity from the leaves of Crinum asiaticum L. var. asiaticum","authors":"Waraluck Chaichompoo , Pornchai Rojsitthisak , Nassareen Supaweera , Preeyaporn Poldorn , Wachirachai Pabuprapap , Warangkana Chunglok , Yutthana Wongnongwa , Apichart Suksamrarn","doi":"10.1016/j.phytochem.2025.114383","DOIUrl":"10.1016/j.phytochem.2025.114383","url":null,"abstract":"<div><div>Forty-two Amaryllidaceae alkaloids, including eleven previously undescribed alkaloids, crinasiaticines C–M, and three undescribed naturally occurring alkaloids, (+)-dihydroepivittatine, (+)-dihydrovittatine and (+)-dihydrohamayne, were isolated from the leaves of <em>Crinum asiaticum</em> L. var. <em>asiaticum</em>. Their structures and configurations were elucidated using NMR and MS spectroscopic techniques, along with the comparison of experimental electronic circular dichroism spectra to calculated data. The anti-inflammatory activity against nitric oxide (NO) production in lipopolysaccharide-stimulated RAW264.7 cells was evaluated for most of the isolated alkaloids. Compounds <strong>39</strong>, <strong>21</strong>, <strong>22</strong>, and <strong>35</strong> exhibited considerable NO inhibitory activity, with IC<sub>50</sub> values of 2.5–2.6 μM, compared to positive control dexamethasone (IC<sub>50</sub> 2.7 μM). However, these compounds demonstrated cytotoxic effects on cells. Compound <strong>15</strong> also possessed the highest selectivity index of 22.5 with minimal cytotoxicity.</div></div>","PeriodicalId":20170,"journal":{"name":"Phytochemistry","volume":"233 ","pages":"Article 114383"},"PeriodicalIF":3.2,"publicationDate":"2025-01-03","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"142932167","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 : 2025-01-03DOI: 10.1016/j.phytochem.2025.114380
Yi-Wei Liu , Xue-Yi Hu , Xiao-Dan Chen , Xiao-Ming Li , Sui-Qun Yang , Hong-Lei Li , Bin-Gui Wang
Six previously undescribed spiromeroterpenoids, chermesins I–N (1–6), were isolated and identified from the marine-sourced fungus Penicillium chermesinum AS-400. Their structures were determined by nuclear magnetic resonance and mass spectroscopic data, and the relative and absolute configurations were confirmed based on nuclear Overhauser effect spectroscopic experiments, electronic circular dichroism (ECD) calculations and X-ray crystallographic analysis, and by comparisons of ECD Cotton effects with those of known congeners as well. Structurally, compound 1 represents the first example of spiromeroterpenoid demethylated at C-4. The isolated compounds exhibited inhibitory activities against several aquatic and human pathogenic bacteria with MIC values ranging from 4 to 64 μg/mL.
{"title":"Chermesins I-N: Bioactive spiromeroterpenoids from the marine-sourced fungus Penicillium chermesinum AS-400","authors":"Yi-Wei Liu , Xue-Yi Hu , Xiao-Dan Chen , Xiao-Ming Li , Sui-Qun Yang , Hong-Lei Li , Bin-Gui Wang","doi":"10.1016/j.phytochem.2025.114380","DOIUrl":"10.1016/j.phytochem.2025.114380","url":null,"abstract":"<div><div>Six previously undescribed spiromeroterpenoids, chermesins I–N (<strong>1</strong>–<strong>6</strong>), were isolated and identified from the marine-sourced fungus <em>Penicillium chermesinum</em> AS-400. Their structures were determined by nuclear magnetic resonance and mass spectroscopic data, and the relative and absolute configurations were confirmed based on nuclear Overhauser effect spectroscopic experiments, electronic circular dichroism (ECD) calculations and X-ray crystallographic analysis, and by comparisons of ECD Cotton effects with those of known congeners as well. Structurally, compound <strong>1</strong> represents the first example of spiromeroterpenoid demethylated at C-4. The isolated compounds exhibited inhibitory activities against several aquatic and human pathogenic bacteria with MIC values ranging from 4 to 64 <em>μ</em>g/mL.</div></div>","PeriodicalId":20170,"journal":{"name":"Phytochemistry","volume":"233 ","pages":"Article 114380"},"PeriodicalIF":3.2,"publicationDate":"2025-01-03","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"142927764","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 : 2025-01-03DOI: 10.1016/j.phytochem.2025.114384
Yang Liu , Xi Chen , Xue-Jin Liu , Ren Liu , Hui-Ling Hu , Shan-Xue Min , Chao-Hui Huang , Lin Liu , Gui-Shan Tan
Five racemic phthalides (1–5), including four undescribed phthalides monomers [(+)-1, (+)-2, (−)-2 and (−)-3], four undescribed phthalide dimers [(+)-4, (−)-4, (+)-5 and (−)-5], together with two known compounds [(−)-1 and (+)-3], were isolated from the aerial parts of Lycopodistrum casuarinoides. Their chemical structures were delineated by extensive spectroscopic data (UV, 1D/2D NMR, HRESIMS), in combination with the comparison of the experimental and calculated electronic circular dichroism spectra, calculated spin-spin coupling constants, and calculated NMR. All compounds were reported from Lycopodiaceae family for the first time. In addition, all isolates were tested for their neuroprotective effects on HT-22 cell injury induced by glutamate. Interestingly, among the five racemic phthalides, only the homologous dimers [(±)-5] displayed significant differences in neuroprotective effects, and (−)-5 exhibited the best neuroprotective activity against glutamate-induced HT-22 cells damage, with 29.3% increase rate in cell survival at 5 μM concentration. The neuroprotective effect of (−)-5 at different concentrations is equivalent to that of the positive control drug D/L-3-n-butylphthalide (racemic NBP). Furthermore, the biological evaluation revealed that (−)-5 could ameliorate glutamate-induced neuronal cell death via the Bax/Bcl-2 anti-apoptotic pathway.
从木麻黄番茄的地上部分分离得到5个外消旋苯酞（1-5），包括4个未被描述的苯酞单体[(+)-1、(+)-2、(-)-2和(-)-3]，4个未被描述的苯酞二聚体[(+)-4、(-)-4、(+)-5和(-)-5]，以及2个已知化合物[(-)-1和(+)-3]。通过广泛的光谱数据（UV, 1D/2D NMR, hresms），结合实验和计算的电子圆二色光谱的比较，计算的自旋-自旋耦合常数和计算的NMR，描述了它们的化学结构。所有化合物均为首次从石松科植物中分离得到。此外，我们还检测了所有分离物对谷氨酸诱导的HT-22细胞损伤的神经保护作用。有趣的是，在5种外消旋苯酞中，只有同源二聚体[±)-5]对谷氨酸诱导的HT-22细胞损伤表现出显著的神经保护作用，(-)-5对谷氨酸诱导的HT-22细胞损伤表现出最好的神经保护作用，5 μM浓度下细胞存活率提高29.3%。不同浓度(-)-5的神经保护作用与阳性对照药物D/ l -3-正丁基酞（消旋NBP）相当。此外，生物学评价显示(-)-5可以通过Bax/Bcl-2抗凋亡途径改善谷氨酸诱导的神经元细胞死亡。
{"title":"Five racemic phthalides from the aerial parts of Lycopodiastrum casuarinoides and their neuroprotective activities","authors":"Yang Liu , Xi Chen , Xue-Jin Liu , Ren Liu , Hui-Ling Hu , Shan-Xue Min , Chao-Hui Huang , Lin Liu , Gui-Shan Tan","doi":"10.1016/j.phytochem.2025.114384","DOIUrl":"10.1016/j.phytochem.2025.114384","url":null,"abstract":"<div><div>Five racemic phthalides (<strong>1</strong>–<strong>5</strong>), including four undescribed phthalides monomers [(+)-<strong>1</strong>, (+)-<strong>2</strong>, (−)-<strong>2</strong> and (−)-<strong>3</strong>], four undescribed phthalide dimers [(+)-<strong>4</strong>, (−)-<strong>4</strong>, (+)-<strong>5</strong> and (−)-<strong>5</strong>], together with two known compounds [(−)-<strong>1</strong> and (+)-<strong>3</strong>], were isolated from the aerial parts of <em>Lycopodistrum casuarinoides</em>. Their chemical structures were delineated by extensive spectroscopic data (UV, 1D/2D NMR, HRESIMS), in combination with the comparison of the experimental and calculated electronic circular dichroism spectra, calculated spin-spin coupling constants, and calculated NMR. All compounds were reported from Lycopodiaceae family for the first time. In addition, all isolates were tested for their neuroprotective effects on HT-22 cell injury induced by glutamate. Interestingly, among the five racemic phthalides, only the homologous dimers [(±)-<strong>5</strong>] displayed significant differences in neuroprotective effects, and (−)-<strong>5</strong> exhibited the best neuroprotective activity against glutamate-induced HT-22 cells damage, with 29.3% increase rate in cell survival at 5 μM concentration. The neuroprotective effect of (−)-<strong>5</strong> at different concentrations is equivalent to that of the positive control drug D/L-3-<em>n</em>-butylphthalide (racemic NBP). Furthermore, the biological evaluation revealed that (−)-<strong>5</strong> could ameliorate glutamate-induced neuronal cell death via the Bax/Bcl-2 anti-apoptotic pathway.</div></div>","PeriodicalId":20170,"journal":{"name":"Phytochemistry","volume":"233 ","pages":"Article 114384"},"PeriodicalIF":3.2,"publicationDate":"2025-01-03","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"142932338","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 : 2025-01-03DOI: 10.1016/j.phytochem.2025.114381
An Huang , Mengmeng Yu , Houli Jiang , Danyang Zhang , Zhenyu Zan , Jun Luo , Yi Li
Fifteen sesquiterpenoids, including five previously undescribed monomers with oxidative rearranged skeletons (sarglabenoids A–E, 1–5) and three previously unreported lindenane [2 + 2] dimers (sarglabenoids F–H, 6–8), alongside seven related precursors (9–15), were isolated from the root of Sarcandra glabra. The structures of these compounds were elucidated using a combination of high-resolution electrospray ionization mass spectrometry, one-dimensional and two-dimensional nuclear magnetic resonance spectroscopy, the circular dichroism exciton chirality method, electronic circular dichroism, and nuclear magnetic resonance calculations integrated with DP4+ analysis. Compounds 1 and 2 feature an unique 5/5 spiro ring system, which is likely derived from a pinacol rearrangement of precursor 14. Compounds 3 and 4 are seco-C8/9 derivatives formed via Baeyer-Villiger oxidation of precursors 14 and 15, while compounds 6–8 represent the [2 + 2] dimers of various lindenane monomers (9–13). Notably, compounds 4 and 5 exhibited moderate inhibition of Interleukin-1β production in non-cytotoxic concentration in lipopolysaccharide-induced Tohoku Hospital Pediatrics-1 cells, with IC50 values of 16.28 ± 0.76 μM and 11.32 ± 0.77 μM respectively.
{"title":"Structurally diverse sesquiterpenoids from Sarcandra glabra and their anti-inflammatory activities","authors":"An Huang , Mengmeng Yu , Houli Jiang , Danyang Zhang , Zhenyu Zan , Jun Luo , Yi Li","doi":"10.1016/j.phytochem.2025.114381","DOIUrl":"10.1016/j.phytochem.2025.114381","url":null,"abstract":"<div><div>Fifteen sesquiterpenoids, including five previously undescribed monomers with oxidative rearranged skeletons (sarglabenoids A–E, <strong>1</strong>–<strong>5</strong>) and three previously unreported lindenane [2 + 2] dimers (sarglabenoids F–H, <strong>6</strong>–<strong>8</strong>), alongside seven related precursors (<strong>9</strong>–<strong>15</strong>), were isolated from the root of <em>Sarcandra glabra</em>. The structures of these compounds were elucidated using a combination of high-resolution electrospray ionization mass spectrometry, one-dimensional and two-dimensional nuclear magnetic resonance spectroscopy, the circular dichroism exciton chirality method, electronic circular dichroism, and nuclear magnetic resonance calculations integrated with DP4+ analysis. Compounds <strong>1</strong> and <strong>2</strong> feature an unique 5/5 spiro ring system, which is likely derived from a pinacol rearrangement of precursor <strong>14</strong>. Compounds <strong>3</strong> and <strong>4</strong> are seco-C8/9 derivatives formed via Baeyer-Villiger oxidation of precursors <strong>14</strong> and <strong>15</strong>, while compounds <strong>6</strong>–<strong>8</strong> represent the [2 + 2] dimers of various lindenane monomers (<strong>9</strong>–<strong>13</strong>). Notably, compounds <strong>4</strong> and <strong>5</strong> exhibited moderate inhibition of Interleukin-1<em>β</em> production in non-cytotoxic concentration in lipopolysaccharide-induced Tohoku Hospital Pediatrics-1 cells, with IC<sub>50</sub> values of 16.28 ± 0.76 μM and 11.32 ± 0.77 μM respectively.</div></div>","PeriodicalId":20170,"journal":{"name":"Phytochemistry","volume":"233 ","pages":"Article 114381"},"PeriodicalIF":3.2,"publicationDate":"2025-01-03","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"142932421","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 : 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}
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