Pub Date : 2025-12-01DOI: 10.1016/j.phytochem.2025.114736
Bingyang Zhang , Linghui Shi , Hongqin Liu , Di Liu , Tie Yao , Shijie Cao , Ning Kang , Xinchi Feng , Feng Qiu
Sacraoxides I–Q (1–9), nine undescribed cembranoids were isolated from the gum resin of Boswellia sacra as well as two known analogues (10 and 11). Their structures were determined by the analysis of 1D/2D NMR and HRESIMS data, quantum chemical calculations, modified Mosher's method, and a single-crystal X-ray diffraction study. Compounds 1 and 2 possess an unprecedented 15,16-dioxatricyclo[7.5.1.12,5]hexadecane polyether skeleton. Compound 3 has been identified as the first instance of nor-cembranoid bearing a 13-oxabicyclo[8.2.1]tridecane skeleton. Meanwhile, compounds 4 and 5 have been characterized as unusual 5,6-seco- and 7,8-seco-cembranoids. Plausible biosynthetic pathways were proposed from the naturally occurring cembranoids. The isolated cembranoids were evaluated for their activation towards transient receptor potential vanilloid 3 (TRPV3) by using calcium fluorescent assay and manual whole-cell patch-clamp technique. The results revealed that sacraoxide P (8) significantly activates TRPV3 at 50 μM. Molecular docking and molecular dynamic studies preliminarily undercover that compound 8 targets TRPV3 by forming hydrophobic interactions, hydrogen bond, and van der Waals forces with residues at the nexus of the linker domain, pre-S1 and TRP helices.
{"title":"Structurally diverse cembranoids as natural TRPV3 agonists from gum resin of Boswellia sacra","authors":"Bingyang Zhang , Linghui Shi , Hongqin Liu , Di Liu , Tie Yao , Shijie Cao , Ning Kang , Xinchi Feng , Feng Qiu","doi":"10.1016/j.phytochem.2025.114736","DOIUrl":"10.1016/j.phytochem.2025.114736","url":null,"abstract":"<div><div>Sacraoxides I–Q (<strong>1</strong>–<strong>9</strong>), nine undescribed cembranoids were isolated from the gum resin of <em>Boswellia sacra</em> as well as two known analogues (<strong>10</strong> and <strong>11</strong>). Their structures were determined by the analysis of 1D/2D NMR and HRESIMS data, quantum chemical calculations, modified Mosher's method, and a single-crystal X-ray diffraction study. Compounds <strong>1</strong> and <strong>2</strong> possess an unprecedented 15,16-dioxatricyclo[7.5.1.1<sup>2,5</sup>]hexadecane polyether skeleton. Compound <strong>3</strong> has been identified as the first instance of nor-cembranoid bearing a 13-oxabicyclo[8.2.1]tridecane skeleton. Meanwhile, compounds <strong>4</strong> and <strong>5</strong> have been characterized as unusual 5,6-<em>seco</em>- and 7,8-<em>seco</em>-cembranoids. Plausible biosynthetic pathways were proposed from the naturally occurring cembranoids. The isolated cembranoids were evaluated for their activation towards transient receptor potential vanilloid 3 (TRPV3) by using calcium fluorescent assay and manual whole-cell patch-clamp technique. The results revealed that sacraoxide P (<strong>8</strong>) significantly activates TRPV3 at 50 <em>μ</em>M. Molecular docking and molecular dynamic studies preliminarily undercover that compound <strong>8</strong> targets TRPV3 by forming hydrophobic interactions, hydrogen bond, and van der Waals forces with residues at the nexus of the linker domain, pre-S1 and TRP helices.</div></div>","PeriodicalId":20170,"journal":{"name":"Phytochemistry","volume":"243 ","pages":"Article 114736"},"PeriodicalIF":3.4,"publicationDate":"2025-12-01","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"145669105","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}
Fifteen undescribed polyketides aculeatides A-O and one known compound xylarinol A were isolated from the endophytic fungus Aspergillus aculeatus. Their structures were identified by spectroscopic data, electronic circular dichroism (ECD) calculations and comparisons, Mo2(OAc)4-induced ECD, Rh2(OCOCF3)4-induced ECD, and the modified Mosher's method. Aculeatides A and B represent the first benzo[c]oxepine derivatives bearing a C6 side chain, while aculeatides C-I possessed a benzofuran ring system featuring a unique C8 side chain. Biologically, aculeatides J and K showed significant herbicidal activities with IC50 values of 3.01 ± 0.40 and 3.33 ± 0.52 μM.
{"title":"Structurally diverse polyketides with herbicidal activity from the fungus Aspergillus aculeatus.","authors":"Fei Liu, Shanshan Hong, Xiaoxia Gu, Qian Zhang, Qin Li, Weiguang Sun, Chunmei Chen, Yonghui Zhang, Hucheng Zhu","doi":"10.1016/j.phytochem.2025.114631","DOIUrl":"10.1016/j.phytochem.2025.114631","url":null,"abstract":"<p><p>Fifteen undescribed polyketides aculeatides A-O and one known compound xylarinol A were isolated from the endophytic fungus Aspergillus aculeatus. Their structures were identified by spectroscopic data, electronic circular dichroism (ECD) calculations and comparisons, Mo<sub>2</sub>(OAc)<sub>4</sub>-induced ECD, Rh<sub>2</sub>(OCOCF<sub>3</sub>)<sub>4</sub>-induced ECD, and the modified Mosher's method. Aculeatides A and B represent the first benzo[c]oxepine derivatives bearing a C6 side chain, while aculeatides C-I possessed a benzofuran ring system featuring a unique C8 side chain. Biologically, aculeatides J and K showed significant herbicidal activities with IC<sub>50</sub> values of 3.01 ± 0.40 and 3.33 ± 0.52 μM.</p>","PeriodicalId":20170,"journal":{"name":"Phytochemistry","volume":" ","pages":"114631"},"PeriodicalIF":3.4,"publicationDate":"2025-12-01","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"144785028","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 : 2025-12-01DOI: 10.1016/j.phytochem.2025.114740
Jia-Xin Huang , Long-Gao Xiao , Tao-Bin He , Huan Yan , Xiao-Xiao Huang , Hai-Yang Liu
Seven previously undescribed sesquiterpenoids, designated as chloranholosins N‒T (1–7), including two acorane-type sesquiterpenoids (1–2), two lindenane-type sesquiterpenoids (3–4), and three eudesmane-type sesquiterpenoids (5–7), together with six known analogues (8–13) were isolated from the whole plants of Chloranthus holostegius var. Shimianensis. Their structures and absolute configurations were elucidated by a comprehensive method including the spectroscopic data, electronic circular dichroism calculations, and single-crystal X-ray diffraction. Compounds 5 and 6 are the first instances of eudesmane-type sesquiterpenoids with tigloyl and senecioyl substitutions at C-15, respectively. Additionally, the isolates were evaluated for their inhibitory activities against LPS induced nitric oxide production in RAW 264.7 macrophage cells. Among them, compounds 5 and 10 showed significant inhibitory activities with IC50 values of 9.35 ± 1.49 and 3.94 ± 0.69 μM, respectively. Compounds 1, 3, 4, 6, 9, and 12 showed moderate inhibitory activities with IC50 values from 10.48 to 35.36 μM, compared with that of the positive drug dexamethasone at 15.01 ± 1.33 μM.
{"title":"Sesquiterpenoids from Chloranthus holostegius var. shimianensis: Structures and anti-inflammatory activities","authors":"Jia-Xin Huang , Long-Gao Xiao , Tao-Bin He , Huan Yan , Xiao-Xiao Huang , Hai-Yang Liu","doi":"10.1016/j.phytochem.2025.114740","DOIUrl":"10.1016/j.phytochem.2025.114740","url":null,"abstract":"<div><div>Seven previously undescribed sesquiterpenoids, designated as chloranholosins N‒T (<strong>1</strong>–<strong>7</strong>), including two acorane-type sesquiterpenoids (<strong>1</strong>–<strong>2</strong>), two lindenane-type sesquiterpenoids (<strong>3</strong>–<strong>4</strong>), and three eudesmane-type sesquiterpenoids (<strong>5</strong>–<strong>7</strong>), together with six known analogues (<strong>8</strong>–<strong>13</strong>) were isolated from the whole plants of <em>Chloranthus holostegius</em> var. <em>Shimianensis</em>. Their structures and absolute configurations were elucidated by a comprehensive method including the spectroscopic data, electronic circular dichroism calculations, and single-crystal X-ray diffraction. Compounds <strong>5</strong> and <strong>6</strong> are the first instances of eudesmane-type sesquiterpenoids with tigloyl and senecioyl substitutions at C-15, respectively. Additionally, the isolates were evaluated for their inhibitory activities against LPS induced nitric oxide production in RAW 264.7 macrophage cells. Among them, compounds <strong>5</strong> and <strong>10</strong> showed significant inhibitory activities with IC<sub>50</sub> values of 9.35 ± 1.49 and 3.94 ± 0.69 μM, respectively. Compounds <strong>1</strong>, <strong>3</strong>, <strong>4</strong>, <strong>6</strong>, <strong>9</strong>, and <strong>12</strong> showed moderate inhibitory activities with IC<sub>50</sub> values from 10.48 to 35.36 μM, compared with that of the positive drug dexamethasone at 15.01 ± 1.33 μM.</div></div>","PeriodicalId":20170,"journal":{"name":"Phytochemistry","volume":"243 ","pages":"Article 114740"},"PeriodicalIF":3.4,"publicationDate":"2025-12-01","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"145669076","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 : 2025-12-01Epub Date: 2025-08-06DOI: 10.1016/j.phytochem.2025.114630
Li-Li Guo, Yu Wang, Xinyang Li, He-Ping Chen, Ji-Kai Liu
Epigenetic modification is an effective strategy for uncovering novel metabolites in fungi. In this study, chemical epigenetic manipulation was applied to culture of the fungicolous fungus Montagnula donacina, resulting in significant changes of its specialised metabolite profile. Seventeen undescribed (nor)-bergamotane-type sesquiterpenoids (1-17) were isolated from the culture broth of M. donacina that treated with epigenetic modifier vorinostat. Their structures were established via extensive spectroscopic methods and computational analyses. Compound 1 features a previously undescribed 12-nor-10(9→8)abeo-bergamotane scaffold, postulated to arise via multi-step oxidation and rearrangement reactions from the precursor massarinolin C. All compounds were evaluated for cytotoxicity against the human cancer line HL-60 and for their ability to inhibit nitric oxide production. Compounds 4, 5, and 17 showed moderate inhibition effects on nitric oxide production with inhibition rates of 61.5 %, 24.0 %, and 43.8 % at a concentration of 50 μM, respectively. This study expands the knowledge of bergamotane-type sesquiterpenes and underscores the effectiveness of epigenetic manipulation as a strategy to activate silent biosynthetic pathways and generate novel specialised metabolites in fungi.
{"title":"Bergamotane-family sesquiterpenes from histone deacetylase inhibitor modified cultures of the fungicolous fungus Montagnula donacina (Niessl) Wanas., E.B.G. Jones & K.D. Hyde.","authors":"Li-Li Guo, Yu Wang, Xinyang Li, He-Ping Chen, Ji-Kai Liu","doi":"10.1016/j.phytochem.2025.114630","DOIUrl":"10.1016/j.phytochem.2025.114630","url":null,"abstract":"<p><p>Epigenetic modification is an effective strategy for uncovering novel metabolites in fungi. In this study, chemical epigenetic manipulation was applied to culture of the fungicolous fungus Montagnula donacina, resulting in significant changes of its specialised metabolite profile. Seventeen undescribed (nor)-bergamotane-type sesquiterpenoids (1-17) were isolated from the culture broth of M. donacina that treated with epigenetic modifier vorinostat. Their structures were established via extensive spectroscopic methods and computational analyses. Compound 1 features a previously undescribed 12-nor-10(9→8)abeo-bergamotane scaffold, postulated to arise via multi-step oxidation and rearrangement reactions from the precursor massarinolin C. All compounds were evaluated for cytotoxicity against the human cancer line HL-60 and for their ability to inhibit nitric oxide production. Compounds 4, 5, and 17 showed moderate inhibition effects on nitric oxide production with inhibition rates of 61.5 %, 24.0 %, and 43.8 % at a concentration of 50 μM, respectively. This study expands the knowledge of bergamotane-type sesquiterpenes and underscores the effectiveness of epigenetic manipulation as a strategy to activate silent biosynthetic pathways and generate novel specialised metabolites in fungi.</p>","PeriodicalId":20170,"journal":{"name":"Phytochemistry","volume":" ","pages":"114630"},"PeriodicalIF":3.4,"publicationDate":"2025-12-01","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"144799919","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 : 2025-11-30DOI: 10.1016/j.phytochem.2025.114739
Baodan Zhang , Longhui Liu , Sen Wang , Xiaoqi Sun , Guangrong Zi , Kui Hong , Liyan Sun , Ling Liu
Three previously undescribed citrinin dimers, penicitrones A–C (1–3), and one previously unreported tetramic acid derivative, penipyrrone A (4), along with fourteen previously known compounds (5–18) were isolated from the crude extract of the mangrove-derived fungus Penicillium citrinum WHUF05149. The structures of compounds 1–4 were elucidated through comprehensive spectroscopic analyses and their absolute configurations were determined by the modified Snatzke's method and ECD calculations. Compound 3 demonstrated moderate antifungal activities against three strains of Cryptococcus gattii (3284G14, R265 and 3271G1). Compound 15 displayed antibacterial effects against Bacillus subtilis, Bacillus paranthracis and methicillin-resistant Staphylococcus aureus (MRSA) along with anti-biofilm effects against these pathogens. In addition, compound 15 exhibits anti-MRSA activity by disrupting cell membrane integrity, inducing the leakage of intracellular constituents and reducing intracellular ATP levels.
{"title":"Discovery of antimicrobial citrinin dimers from the mangrove-derived fungus Penicillium citrinum","authors":"Baodan Zhang , Longhui Liu , Sen Wang , Xiaoqi Sun , Guangrong Zi , Kui Hong , Liyan Sun , Ling Liu","doi":"10.1016/j.phytochem.2025.114739","DOIUrl":"10.1016/j.phytochem.2025.114739","url":null,"abstract":"<div><div>Three previously undescribed citrinin dimers, penicitrones A–C (<strong>1</strong>–<strong>3</strong>), and one previously unreported tetramic acid derivative, penipyrrone A (<strong>4</strong>), along with fourteen previously known compounds (<strong>5</strong>–<strong>18</strong>) were isolated from the crude extract of the mangrove-derived fungus <em>Penicillium citrinum</em> WHUF05149. The structures of compounds <strong>1</strong>–<strong>4</strong> were elucidated through comprehensive spectroscopic analyses and their absolute configurations were determined by the modified Snatzke's method and ECD calculations. Compound <strong>3</strong> demonstrated moderate antifungal activities against three strains of <em>Cryptococcus gattii</em> (3284G14, R265 and 3271G1). Compound <strong>15</strong> displayed antibacterial effects against <em>Bacillus subtilis</em>, <em>Bacillus paranthracis</em> and methicillin-resistant <em>Staphylococcus aureus</em> (MRSA) along with anti-biofilm effects against these pathogens. In addition, compound <strong>15</strong> exhibits anti-MRSA activity by disrupting cell membrane integrity, inducing the leakage of intracellular constituents and reducing intracellular ATP levels.</div></div>","PeriodicalId":20170,"journal":{"name":"Phytochemistry","volume":"243 ","pages":"Article 114739"},"PeriodicalIF":3.4,"publicationDate":"2025-11-30","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"145661670","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 : 2025-11-30DOI: 10.1016/j.phytochem.2025.114733
Appolinaire Kene Dongmo , Eric Tameko Mbasso , Raymond Ngansop Nono , Gabin Thierry Mbahbou Bitchagno , Abdou Tchoukoua , Marcus Persicke , Blandine Kampa-Kuemkon Nkenfou , David Ngnokam , Pépin Nkeng-Efouet Alango , Bruno Ndjakou Lenta , Norbert Sewald , Jean Rodolphe Chouna
Natural products have made important contributions to the fight against human diseases, including infectious diseases. However, research on natural products still faces many challenges, such as technical barriers to in-depth screening of biomaterials. The genus Keetia is a valuable source of flavonoids, although the specific types and complete profile of most of its species remain undisclosed. The flavonoid profile of the methanol crude extract and derived extracts from Keetia venosa (Oliv.) Bridson leaves was unveiled using a feature-based molecular networking-guided fractionation strategy. This approach enables a comprehensive exploration of the plant chemical diversity, including the detection of minor components often missed out during traditional isolation and characterisation. Four previously undescribed kaempferol glycosides were isolated, together with sixteen known compounds. Their structures were elucidated by examining their physical, mass spectrometry (MS) and nuclear magnetic resonance (NMR) spectroscopic data. Fourteen additional already reported compounds were putatively identified from a comparative analysis of their MS2 features with similar analogues available in well-known databases. Furthermore, crude extract, partitioned extracts and isolated compounds were evaluated for their antibacterial activity against both Gram-positive and -negative bacteria, including Salmonella enterica, Pseudomonas aeruginosa and Klebsiella pneumoniae. The n-butanol extract, kotschyanoside A, and kaempferol 7-O-α-l-rhamnopyranoside displayed promising antibacterial activity against Gram-negative bacteria such as S. enterica, P. aeruginosa and K. pneumoniae with MIC values of 3.9–62.5 μg/mL.
天然产物对防治人类疾病，包括传染病作出了重要贡献。然而，天然产物的研究仍然面临着许多挑战，如生物材料深度筛选的技术障碍。Keetia属是黄酮类化合物的宝贵来源，尽管其大多数物种的具体类型和完整概况仍未公开。研究了黄酮醇粗提物及其衍生物的类黄酮谱。布里特森叶子使用基于特征的分子网络引导的分馏策略。这种方法能够全面探索植物化学多样性，包括检测在传统分离和表征过程中经常错过的次要成分。分离了四种先前未描述的山奈酚苷，以及16种已知化合物。通过物理、质谱和核磁共振等光谱数据对它们的结构进行了鉴定。另外14种已报道的化合物通过与知名数据库中类似类似物的MS2特征比较分析被推定鉴定出来。此外，还对粗提物、萃取物和分离物的抑菌活性进行了评价，包括革兰氏阳性菌和阴性菌，包括肠沙门氏菌、铜绿假单胞菌和肺炎克雷伯菌。正丁醇提取物、山奈酚7-O-α- l -鼠李糖苷A和山奈酚7-O-α- l -鼠李糖苷对革兰氏阴性菌肠链球菌、铜绿假单胞菌和肺炎克雷伯菌的MIC值为3.9 ~ 62.5 μg/mL，具有良好的抑菌活性。
{"title":"Feature-based molecular networking-guided isolation of kaempferol glycosides from Keetia venosa (Oliv.) Bridson leaves and their antibacterial activity","authors":"Appolinaire Kene Dongmo , Eric Tameko Mbasso , Raymond Ngansop Nono , Gabin Thierry Mbahbou Bitchagno , Abdou Tchoukoua , Marcus Persicke , Blandine Kampa-Kuemkon Nkenfou , David Ngnokam , Pépin Nkeng-Efouet Alango , Bruno Ndjakou Lenta , Norbert Sewald , Jean Rodolphe Chouna","doi":"10.1016/j.phytochem.2025.114733","DOIUrl":"10.1016/j.phytochem.2025.114733","url":null,"abstract":"<div><div>Natural products have made important contributions to the fight against human diseases, including infectious diseases. However, research on natural products still faces many challenges, such as technical barriers to in-depth screening of biomaterials. The genus <em>Keetia</em> is a valuable source of flavonoids, although the specific types and complete profile of most of its species remain undisclosed. The flavonoid profile of the methanol crude extract and derived extracts from <em>Keetia venosa</em> (Oliv.) Bridson leaves was unveiled using a feature-based molecular networking-guided fractionation strategy. This approach enables a comprehensive exploration of the plant chemical diversity, including the detection of minor components often missed out during traditional isolation and characterisation. Four previously undescribed kaempferol glycosides were isolated, together with sixteen known compounds. Their structures were elucidated by examining their physical, mass spectrometry (MS) and nuclear magnetic resonance (NMR) spectroscopic data. Fourteen additional already reported compounds were putatively identified from a comparative analysis of their MS<sup>2</sup> features with similar analogues available in well-known databases. Furthermore, crude extract, partitioned extracts and isolated compounds were evaluated for their antibacterial activity against both Gram-positive and -negative bacteria, including <em>Salmonella enterica</em>, <em>Pseudomonas aeruginosa</em> and <em>Klebsiella pneumoniae.</em> The <em>n</em>-butanol extract, kotschyanoside A, and kaempferol 7-<em>O</em>-<em>α</em>-<span>l</span>-rhamnopyranoside displayed promising antibacterial activity against Gram-negative bacteria such as <em>S. enterica</em>, <em>P. aeruginosa</em> and <em>K. pneumoniae</em> with MIC values of 3.9–62.5 μg/mL.</div></div>","PeriodicalId":20170,"journal":{"name":"Phytochemistry","volume":"243 ","pages":"Article 114733"},"PeriodicalIF":3.4,"publicationDate":"2025-11-30","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"145661649","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 : 2025-11-30DOI: 10.1016/j.phytochem.2025.114734
Si-Hang Lin , Ning Diao , Yan Wang , Dong Liang
Sixteen previously undescribed sesquiterpenoid glycosides (1−16), bearing eudesmane-type (1−4) and cadinane-type skeletons (5−16), were obtained from the stems of Cissampelopsis spelaeicola. The structural elucidation and absolute configuration assignment of compounds 1−16 were accomplished through multiple spectroscopic analyses, computed ECD/NMR, and X-ray crystallography. Furthermore, anti-neuroinflammatory effects of all isolates were assessed by NO inhibition in LPS-stimulated BV-2 microglia. Compounds 12 and 14−16 exhibited potent NO inhibitory effects (IC50 = 5.62–19.29 μM), outperforming the positive control L-NMMA (IC50 = 21.20 ± 0.57 μM). Further evaluation revealed that compound 15 (IC50 = 5.62 ± 0.37 μM) effectively attenuated LPS-stimulated overexpression of IL-1β, IL-6, iNOS, and TNF-α in BV-2 cells.
{"title":"Structurally diverse sesquiterpenoid glycosides with anti-inflammatory activity from Cissampelopsis spelaeicola","authors":"Si-Hang Lin , Ning Diao , Yan Wang , Dong Liang","doi":"10.1016/j.phytochem.2025.114734","DOIUrl":"10.1016/j.phytochem.2025.114734","url":null,"abstract":"<div><div>Sixteen previously undescribed sesquiterpenoid glycosides (<strong>1</strong>−<strong>16</strong>), bearing eudesmane-type (<strong>1</strong>−<strong>4</strong>) and cadinane-type skeletons (<strong>5</strong>−<strong>16</strong>), were obtained from the stems of <em>Cissampelopsis spelaeicola</em>. The structural elucidation and absolute configuration assignment of compounds <strong>1</strong>−<strong>16</strong> were accomplished through multiple spectroscopic analyses, computed ECD/NMR, and X-ray crystallography. Furthermore, anti-neuroinflammatory effects of all isolates were assessed by NO inhibition in LPS-stimulated BV-2 microglia. Compounds <strong>12</strong> and <strong>14</strong>−<strong>16</strong> exhibited potent NO inhibitory effects (IC<sub>50</sub> = 5.62–19.29 μM), outperforming the positive control L-NMMA (IC<sub>50</sub> = 21.20 ± 0.57 μM). Further evaluation revealed that compound <strong>15</strong> (IC<sub>50</sub> = 5.62 ± 0.37 μM) effectively attenuated LPS-stimulated overexpression of IL-1β, IL-6, iNOS, and TNF-α in BV-2 cells.</div></div>","PeriodicalId":20170,"journal":{"name":"Phytochemistry","volume":"243 ","pages":"Article 114734"},"PeriodicalIF":3.4,"publicationDate":"2025-11-30","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"145661636","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 : 2025-11-30DOI: 10.1016/j.phytochem.2025.114737
Xing-Yan Feng , Sui-Qun Yang , Xiao-Ming Li , Xin Li , Bin-Gui Wang , Ling-Hong Meng
Chemical investigation of the cold-seep-sourced fungus Talaromyces trachyspermus CS-106 resulted in the isolation of six previously undescribed phenolic glucopyranosides, talarosides A–F (1–6), two previously undescribed phenolic cysteine derivatives, talacysteines A and B (7 and 8), and five known congeners 9–13. The results from in vitro bioassay indicated that compounds 3, 6, and 9 displayed potent activities against several tested phytopathogenic fungal strains. Specially, the chloroquinone derivative, 2-chloro-5-methoxy-3-methylcyclohexa-2,5-diene-1,4-dione (compound 9), exhibited a broad spectrum of fungicidal activity against Alternaria brassicae, Colletotrichum gloeosporioides, Fusarium graminearum, and F. oxysporum, with MIC values ranging from 0.5 to 4 μg/mL. In vivo testing on tomato fruits showed that 9 displayed considerable curative efficacy against F. oxysporum. Both scanning electron microscopy and cryo-SEM analysis indicated that 9 possessed a strong ability to destroy the surface morphology of mycelia and seriously interfere with the growth of the fungal pathogen. Compound 9 also exhibited pronounced succinate dehydrogenase (SDH) inhibitory activity from the in vitro SDH inhibitory assay. Molecular docking simulations were performed to explore the intermolecular interaction of 9 with SDH enzyme from F. oxysporum. These findings presented a promising lead compound such as compound 9 for the discovery of SDH inhibitor as antifungal agents.
{"title":"Antifungal phenolic glucosides and related congeners from the cold-seep-derived Talaromyces trachyspermus CS-106","authors":"Xing-Yan Feng , Sui-Qun Yang , Xiao-Ming Li , Xin Li , Bin-Gui Wang , Ling-Hong Meng","doi":"10.1016/j.phytochem.2025.114737","DOIUrl":"10.1016/j.phytochem.2025.114737","url":null,"abstract":"<div><div>Chemical investigation of the cold-seep-sourced fungus <em>Talaromyces trachyspermus</em> CS-106 resulted in the isolation of six previously undescribed phenolic glucopyranosides, talarosides A<strong>–</strong>F (<strong>1</strong>–<strong>6</strong>), two previously undescribed phenolic cysteine derivatives, talacysteines A and B (<strong>7</strong> and <strong>8</strong>), and five known congeners <strong>9</strong>–<strong>13</strong>. The results from <em>in vitro</em> bioassay indicated that compounds <strong>3</strong>, <strong>6</strong>, and <strong>9</strong> displayed potent activities against several tested phytopathogenic fungal strains. Specially, the chloroquinone derivative, 2-chloro-5-methoxy-3-methylcyclohexa-2,5-diene-1,4-dione (compound <strong>9</strong>), exhibited a broad spectrum of fungicidal activity against <em>Alternaria brassicae</em>, <em>Colletotrichum gloeosporioides</em>, <em>Fusarium graminearum</em>, and <em>F. oxysporum</em>, with MIC values ranging from 0.5 to 4 μg/mL. <em>In vivo</em> testing on tomato fruits showed that <strong>9</strong> displayed considerable curative efficacy against <em>F. oxysporum</em>. Both scanning electron microscopy and cryo-SEM analysis indicated that <strong>9</strong> possessed a strong ability to destroy the surface morphology of mycelia and seriously interfere with the growth of the fungal pathogen. Compound <strong>9</strong> also exhibited pronounced succinate dehydrogenase (SDH) inhibitory activity from the <em>in vitro</em> SDH inhibitory assay. Molecular docking simulations were performed to explore the intermolecular interaction of <strong>9</strong> with SDH enzyme from <em>F. oxysporum</em>. These findings presented a promising lead compound such as compound <strong>9</strong> for the discovery of SDH inhibitor as antifungal agents.</div></div>","PeriodicalId":20170,"journal":{"name":"Phytochemistry","volume":"243 ","pages":"Article 114737"},"PeriodicalIF":3.4,"publicationDate":"2025-11-30","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"145661631","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 : 2025-11-27DOI: 10.1016/j.phytochem.2025.114726
Wei Li , Miaomiao Chai , Longfei Zhang , Mengting Yang , Zhenzhen Zhang , Zhenhui Wang , Xueqian He
Six aloe-emodin derivatives, anthractones A-F (1–6), along with the known compound N-phenethylacetamide (7), were obtained from the biotransformation of aloe-emodin by Fusarium citricola HPU-L64, a fungus isolated from the Yellow River wetland. The structures of 1–7 were elucidated by comprehensive analysis of NMR spectroscopy, HRESIMS data, and X-ray crystallography. Anthracetones possess a distinctive fused 6/6/6/6/6 pentacyclic ring system, contrasting with the typical 6/6/6 tricyclic scaffold of previously reported aloe-emodin derivatives. Anthractone D exhibited enhanced antibacterial activity against Bacillus subtilis (MIC = 2.6 μM), demonstrating greater potency than aloe-emodin (MIC = 14.8 μM).
{"title":"Anthractones A-F, antibacterial anthraquinone lactones from the biotransformation of aloe-emodin by Fusarium citricola","authors":"Wei Li , Miaomiao Chai , Longfei Zhang , Mengting Yang , Zhenzhen Zhang , Zhenhui Wang , Xueqian He","doi":"10.1016/j.phytochem.2025.114726","DOIUrl":"10.1016/j.phytochem.2025.114726","url":null,"abstract":"<div><div>Six aloe-emodin derivatives, anthractones A-F (<strong>1</strong>–<strong>6</strong>), along with the known compound <em>N</em>-phenethylacetamide (<strong>7</strong>), were obtained from the biotransformation of aloe-emodin by <em>Fusarium citricola</em> HPU-L64, a fungus isolated from the Yellow River wetland. The structures of <strong>1</strong>–<strong>7</strong> were elucidated by comprehensive analysis of NMR spectroscopy, HRESIMS data, and X-ray crystallography. Anthracetones possess a distinctive fused 6/6/6/6/6 pentacyclic ring system, contrasting with the typical 6/6/6 tricyclic scaffold of previously reported aloe-emodin derivatives. Anthractone D exhibited enhanced antibacterial activity against <em>Bacillus subtilis</em> (MIC = 2.6 μM), demonstrating greater potency than aloe-emodin (MIC = 14.8 μM).</div></div>","PeriodicalId":20170,"journal":{"name":"Phytochemistry","volume":"243 ","pages":"Article 114726"},"PeriodicalIF":3.4,"publicationDate":"2025-11-27","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"145637684","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 : 2025-11-27DOI: 10.1016/j.phytochem.2025.114720
Liting Ma , Yizhu Wang , Tao Ren, Lijia Pan, Xinze Li, Shen Wang, Dihao Li, Meiyu Zhang, Fangtong Li, Fei Zheng, Hao Yue
Emerging evidence indicates that metabolic dysfunction-associated steatotic liver disease (MASLD) is strongly associated with gut microbial dysbiosis and disruption of the intestinal mucosal barrier function. Scutellaria baicalensis extract (SBE) has anti-inflammatory and hepatoprotective effects. In this study, the investigation conducted explored whether SBE can alleviate MASLD and the possible mechanism involving the gut-liver axis. Qualitative and quantitative analyses of SBE using UPLC-Q-Orbitrap-MS and UPLC-QqQ-MS revealed that the major component of SBE was Baicalin, which accounted for approximately 94.12 %. A mice model of MASLD was established by feeding mice a high-fat diet (HFD) and administering SBE intragastrically. The effects of SBE on liver biochemical parameters, intestinal histopathology, intestinal integrity, and gut microbiota were evaluated. SBE restored the expression of TJs in the intestine and ameliorated the increased permeability of the intestinal mucosa induced by the HFD, thereby enhancing the function of the intestinal barrier. In addition, SBE altered the composition of the gut microbiota in mice with MASLD, decreasing the abundance of Helicobacter and increasing the abundance of Bacteroidota. The results of fecal metabolomics showed that medium-dose SBE significantly upregulated the levels of 11 metabolites, including cholic acid, and downregulated the levels of 13 metabolites, including allantoic acid. Moreover, SBE may reverse HFD-induced hepatic steatosis in mice, suggesting that SBE could serve as a potential therapeutic strategy for MASLD.
{"title":"Scutellaria baicalensis extract prevents metabolic dysfunction-associated steatotic liver disease by modulating the gut-liver axis in high-fat diet mice","authors":"Liting Ma , Yizhu Wang , Tao Ren, Lijia Pan, Xinze Li, Shen Wang, Dihao Li, Meiyu Zhang, Fangtong Li, Fei Zheng, Hao Yue","doi":"10.1016/j.phytochem.2025.114720","DOIUrl":"10.1016/j.phytochem.2025.114720","url":null,"abstract":"<div><div>Emerging evidence indicates that metabolic dysfunction-associated steatotic liver disease (MASLD) is strongly associated with gut microbial dysbiosis and disruption of the intestinal mucosal barrier function. <em>Scutellaria baicalensis</em> extract (SBE) has anti-inflammatory and hepatoprotective effects. In this study, the investigation conducted explored whether SBE can alleviate MASLD and the possible mechanism involving the gut-liver axis. Qualitative and quantitative analyses of SBE using UPLC-Q-Orbitrap-MS and UPLC-QqQ-MS revealed that the major component of SBE was Baicalin, which accounted for approximately 94.12 %. A mice model of MASLD was established by feeding mice a high-fat diet (HFD) and administering SBE intragastrically. The effects of SBE on liver biochemical parameters, intestinal histopathology, intestinal integrity, and gut microbiota were evaluated. SBE restored the expression of TJs in the intestine and ameliorated the increased permeability of the intestinal mucosa induced by the HFD, thereby enhancing the function of the intestinal barrier. In addition, SBE altered the composition of the gut microbiota in mice with MASLD, decreasing the abundance of <em>Helicobacter</em> and increasing the abundance of <em>Bacteroidota</em>. The results of fecal metabolomics showed that medium-dose SBE significantly upregulated the levels of 11 metabolites, including cholic acid, and downregulated the levels of 13 metabolites, including allantoic acid. Moreover, SBE may reverse HFD-induced hepatic steatosis in mice, suggesting that SBE could serve as a potential therapeutic strategy for MASLD.</div></div>","PeriodicalId":20170,"journal":{"name":"Phytochemistry","volume":"243 ","pages":"Article 114720"},"PeriodicalIF":3.4,"publicationDate":"2025-11-27","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"145637623","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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