Pub Date : 2025-12-12DOI: 10.1016/j.phytochem.2025.114749
Qinlin Cao , Xiaoyan Pang , Mengjing Cong , Ziqing Li , Junfeng Wang , Xuefeng Zhou , Bin Yang , Weijia Zhang , Yonghong Liu
Two undescribed triterpene glycosides (1–2), one undescribed sesquiterpene glycoside (3), three undescribed α-pyrone derivatives (4–6) and one undescribed aliphatic hydrocarbon (7), along with twelve known compounds (8–19), were obtained from a culture of the fungus Nigrocephalum sp. SCSIO41049, separated from Mariana Trench sediment. Compounds 1 and 2 were the first discovered lanostane-type triterpenes with a d-mannose attached at the C-23. Compound 14 was isolated from nature for the first time. Their structures were elucidated based on 1D, 2D NMR and HR-ESI-MS spectral data analysis, followed by electronic circular dichroism (ECD) calculations, single-crystal X-ray diffraction analysis and acid hydrolysis reaction. All compounds were tested for their antimicrobial, enzyme inhibition and antitumor effects. Compound 1 displayed the potent inhibitory effect on Fusarium oxysporum HNM1003 with MIC value of 4 μg/mL. Compounds 6, 8, 11 and 15 demonstrated moderate inhibitory effects on Curvularia australiensis. Compounds 1, 2 and 10 exhibited significant neuraminidase inhibitory activity with IC50 values ranging from 33.02 to 43.55 μM.
{"title":"Structurally specialised metabolites with antimicrobial and enzyme inhibitory activities from Hadal Trench-derived Nigrocephalum sp. SCSIO41049","authors":"Qinlin Cao , Xiaoyan Pang , Mengjing Cong , Ziqing Li , Junfeng Wang , Xuefeng Zhou , Bin Yang , Weijia Zhang , Yonghong Liu","doi":"10.1016/j.phytochem.2025.114749","DOIUrl":"10.1016/j.phytochem.2025.114749","url":null,"abstract":"<div><div>Two undescribed triterpene glycosides (<strong>1</strong>–<strong>2</strong>), one undescribed sesquiterpene glycoside (<strong>3</strong>), three undescribed α-pyrone derivatives (<strong>4</strong>–<strong>6</strong>) and one undescribed aliphatic hydrocarbon (<strong>7</strong>), along with twelve known compounds (<strong>8</strong>–<strong>19</strong>), were obtained from a culture of the fungus <em>Nigrocephalum</em> sp. SCSIO41049, separated from Mariana Trench sediment. Compounds <strong>1</strong> and <strong>2</strong> were the first discovered lanostane-type triterpenes with a <sub><span>d</span></sub>-mannose attached at the C-23. Compound <strong>14</strong> was isolated from nature for the first time. Their structures were elucidated based on 1D, 2D NMR and HR-ESI-MS spectral data analysis, followed by electronic circular dichroism (ECD) calculations, single-crystal X-ray diffraction analysis and acid hydrolysis reaction. All compounds were tested for their antimicrobial, enzyme inhibition and antitumor effects. Compound <strong>1</strong> displayed the potent inhibitory effect on <em>Fusarium oxysporum</em> HNM1003 with MIC value of 4 μg/mL. Compounds <strong>6</strong>, <strong>8</strong>, <strong>11</strong> and <strong>15</strong> demonstrated moderate inhibitory effects on <em>Curvularia australiensis</em>. Compounds <strong>1</strong>, <strong>2</strong> and <strong>10</strong> exhibited significant neuraminidase inhibitory activity with IC<sub>50</sub> values ranging from 33.02 to 43.55 μM.</div></div>","PeriodicalId":20170,"journal":{"name":"Phytochemistry","volume":"244 ","pages":"Article 114749"},"PeriodicalIF":3.4,"publicationDate":"2025-12-12","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"145756221","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 : 2025-12-12DOI: 10.1016/j.phytochem.2025.114748
Jiangping Wu , Shihan He , Zhu Yang , Jianping Zhao , Yiping Yang , Qiangbao Xu , Juan Feng , Qiuyue Lv , Zhongmei Zou , Jun Han
Ten withanolides (1–10) were isolated from Physalis minima L., a medicinal and edible plant. Among them, five (1–5) are previously undescribed. Their chemical structures were established through comprehensive spectroscopic and spectrometric analyses. In vitro bioassays revealed that compounds 2–5 and 8 significantly inhibited nitric oxide production in lipopolysaccharide (LPS)-stimulated murine RAW 264.7 cells, exhibiting anti-inflammatory effects with IC50 values ranging from 4.29 to 25.54 μM. Compound 2, which was identified as phyminiolide B and was the most abundant and potent one, potently reduced inflammatory cytokines release and downregulated COX-2 and iNOS expression. Mechanistically, it inhibited the activation of the NF-κB and MAPK pathways by blocking the phosphorylation of IKKα/β, IκBα, ERK, JNK, and p38. Furthermore, molecular docking and molecular dynamics simulation revealed that phyminiolide B exhibited strong binding affinity for the TLR4/MD2 complex, with a calculated binding energy of −9.0 kcal/mol. Additionally, in vivo experiments confirmed that phyminiolide B markedly alleviated LPS-induced acute lung injury in animal models, underscoring its therapeutic potential for inflammatory diseases. The findings provided valuable insights into the structural diversity and anti-inflammatory mechanisms of withanolides from P. minima.
{"title":"Withanolides from Physalis minima as potential anti-inflammatory agents: From isolation to in vitro and in vivo validation","authors":"Jiangping Wu , Shihan He , Zhu Yang , Jianping Zhao , Yiping Yang , Qiangbao Xu , Juan Feng , Qiuyue Lv , Zhongmei Zou , Jun Han","doi":"10.1016/j.phytochem.2025.114748","DOIUrl":"10.1016/j.phytochem.2025.114748","url":null,"abstract":"<div><div>Ten withanolides (<strong>1</strong>–<strong>10</strong>) were isolated from <em>Physalis minima</em> L., a medicinal and edible plant. Among them, five (<strong>1</strong>–<strong>5</strong>) are previously undescribed. Their chemical structures were established through comprehensive spectroscopic and spectrometric analyses. <em>In vitro</em> bioassays revealed that compounds <strong>2</strong>–<strong>5</strong> and <strong>8</strong> significantly inhibited nitric oxide production in lipopolysaccharide (LPS)-stimulated murine RAW 264.7 cells, exhibiting anti-inflammatory effects with IC<sub>50</sub> values ranging from 4.29 to 25.54 μM. Compound <strong>2</strong>, which was identified as phyminiolide B and was the most abundant and potent one, potently reduced inflammatory cytokines release and downregulated COX-2 and iNOS expression. Mechanistically, it inhibited the activation of the NF-<em>κ</em>B and MAPK pathways by blocking the phosphorylation of IKKα/β, IκBα, ERK, JNK, and p38. Furthermore, molecular docking and molecular dynamics simulation revealed that phyminiolide B exhibited strong binding affinity for the TLR4/MD2 complex, with a calculated binding energy of −9.0 kcal/mol. Additionally, <em>in vivo</em> experiments confirmed that phyminiolide B markedly alleviated LPS-induced acute lung injury in animal models, underscoring its therapeutic potential for inflammatory diseases. The findings provided valuable insights into the structural diversity and anti-inflammatory mechanisms of withanolides from <em>P. minima</em>.</div></div>","PeriodicalId":20170,"journal":{"name":"Phytochemistry","volume":"244 ","pages":"Article 114748"},"PeriodicalIF":3.4,"publicationDate":"2025-12-12","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"145756182","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 : 2025-12-12DOI: 10.1016/j.phytochem.2025.114747
Da-Le Guo , Li Huang , Hui-Min Zhang , Yu-Ting Mu , Hao-Ran Lei , Li-Lian Zhao , Su Hu , Yun-Jie Hu , Cong-Cong Li , Meng-Dan Liu , Yu-Cheng Gu , Guan-Kui Yang , Wei-Zhen Dong , Dong Wang , Yun Deng
Nine previously undescribed coumarin congeners, including ailancoumaquinone A (1) and ailancoumarins M-T (2−9), were isolated from the root bark of Ailanthus altissima (Mill.) Swingle. Their structures were confirmed through spectral analyses, computational approaches, and the Mosher's method. Among these compounds, ailancoumaquinone A (1) was identified as a rare hybrid of a coumarin and a naphthoquinone, featuring an unprecedented carbon skeleton in its naphthoquinone moiety. Furthermore, 1 demonstrated significant anti-inflammatory potential, as it not only inhibits pro-inflammatory factors, including nitric oxide (NO) and reactive oxygen species (ROS) in LPS-induced RAW 264.7 macrophages at a concentration of 7.5 μM but also suppresses ROS secretion in the gastrointestinal tract of LPS-treated zebrafish embryos at a concentration of 3.75 μM. Subsequent pharmacological investigations revealed that 1 inhibits the phosphorylation of Janus kinase 2 (P-JAK2), thereby affecting the phosphorylation of nodal proteins in the downstream signaling pathways that are closely associated with inflammation. Molecular docking analysis indicated that 1 occupies the core ATP-binding pocket within the kinase domain of JAK2 (docking score: −8.214 kcal/mol), suggesting that it may function as a competitive inhibitor of JAK2 kinase activity.
{"title":"Ailancoumaquinone A and ailancoumarins M-T, undescribed terpenylated coumarins from Ailanthus altissima and their anti-inflammatory activity","authors":"Da-Le Guo , Li Huang , Hui-Min Zhang , Yu-Ting Mu , Hao-Ran Lei , Li-Lian Zhao , Su Hu , Yun-Jie Hu , Cong-Cong Li , Meng-Dan Liu , Yu-Cheng Gu , Guan-Kui Yang , Wei-Zhen Dong , Dong Wang , Yun Deng","doi":"10.1016/j.phytochem.2025.114747","DOIUrl":"10.1016/j.phytochem.2025.114747","url":null,"abstract":"<div><div>Nine previously undescribed coumarin congeners, including ailancoumaquinone A (<strong>1</strong>) and ailancoumarins M-T (<strong>2</strong>−<strong>9</strong>), were isolated from the root bark of <em>Ailanthus altissima</em> (Mill.) Swingle. Their structures were confirmed through spectral analyses, computational approaches, and the Mosher's method. Among these compounds, ailancoumaquinone A (<strong>1</strong>) was identified as a rare hybrid of a coumarin and a naphthoquinone, featuring an unprecedented carbon skeleton in its naphthoquinone moiety. Furthermore, <strong>1</strong> demonstrated significant anti-inflammatory potential, as it not only inhibits pro-inflammatory factors, including nitric oxide (NO) and reactive oxygen species (ROS) in LPS-induced RAW 264.7 macrophages at a concentration of 7.5 μM but also suppresses ROS secretion in the gastrointestinal tract of LPS-treated zebrafish embryos at a concentration of 3.75 μM. Subsequent pharmacological investigations revealed that <strong>1</strong> inhibits the phosphorylation of Janus kinase 2 (P-JAK2), thereby affecting the phosphorylation of nodal proteins in the downstream signaling pathways that are closely associated with inflammation. Molecular docking analysis indicated that <strong>1</strong> occupies the core ATP-binding pocket within the kinase domain of JAK2 (docking score: −8.214 kcal/mol), suggesting that it may function as a competitive inhibitor of JAK2 kinase activity.</div></div>","PeriodicalId":20170,"journal":{"name":"Phytochemistry","volume":"244 ","pages":"Article 114747"},"PeriodicalIF":3.4,"publicationDate":"2025-12-12","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"145757368","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 : 2025-12-10DOI: 10.1016/j.phytochem.2025.114745
Chang-Sheng Gao , Pei-Lin Su , Mei-Ya Lian, Zhi-Kang Duan, Shu-Hui Dong, Shao-Jiang Song
Tripterygium wilfordii Hook. f. (Celastraceae family) is a well-recognized medicinal plant valued for its structurally diverse and pharmacologically active specialized metabolites, particularly dihydro-β-agarofuran sesquiterpenoids and macrocyclic sesquiterpene pyridine alkaloids. These compounds exhibit a broad range of biological activities, including anti-inflammatory, anticancer, and neuroprotective effects, with promising potential in the treatment of neuroinflammatory conditions. This review provides a systematic overview of the phytochemical composition and pharmacological properties of T. wilfordii, with a particular emphasis on the tissue-specific distribution of dihydro-β-agarofuran sesquiterpenoids and macrocyclic sesquiterpene pyridine alkaloids across various plant parts and among related genera within the Celastraceae family. These compounds not only demonstrate notable bioactivity but also serve as distinctive chemotaxonomic markers. The findings underscore that compound-enriched tissues may provide novel insights for in-depth phytochemical exploration and the development of potential therapeutics.
{"title":"Tripterygium wilfordii Hook. f.: A comprehensive review on phytochemical, pharmacological and tissue-specific distribution of active components","authors":"Chang-Sheng Gao , Pei-Lin Su , Mei-Ya Lian, Zhi-Kang Duan, Shu-Hui Dong, Shao-Jiang Song","doi":"10.1016/j.phytochem.2025.114745","DOIUrl":"10.1016/j.phytochem.2025.114745","url":null,"abstract":"<div><div><em>Tripterygium wilfordii</em> Hook. f. (Celastraceae family) is a well-recognized medicinal plant valued for its structurally diverse and pharmacologically active specialized metabolites, particularly dihydro-<em>β</em>-agarofuran sesquiterpenoids and macrocyclic sesquiterpene pyridine alkaloids. These compounds exhibit a broad range of biological activities, including anti-inflammatory, anticancer, and neuroprotective effects, with promising potential in the treatment of neuroinflammatory conditions. This review provides a systematic overview of the phytochemical composition and pharmacological properties of <em>T. wilfordii</em>, with a particular emphasis on the tissue-specific distribution of dihydro-<em>β</em>-agarofuran sesquiterpenoids and macrocyclic sesquiterpene pyridine alkaloids across various plant parts and among related genera within the Celastraceae family. These compounds not only demonstrate notable bioactivity but also serve as distinctive chemotaxonomic markers. The findings underscore that compound-enriched tissues may provide novel insights for in-depth phytochemical exploration and the development of potential therapeutics.</div></div>","PeriodicalId":20170,"journal":{"name":"Phytochemistry","volume":"244 ","pages":"Article 114745"},"PeriodicalIF":3.4,"publicationDate":"2025-12-10","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"145743760","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 : 2025-12-09DOI: 10.1016/j.phytochem.2025.114744
Xin-Wen Luo , Fang-Lu Wei , Hong-Fei Li , Jin-Yao Mao , Yan-Ling Yang , Juan He , Tao Feng
The systematic chemical investigation of the ethyl acetate extract of the rice-fermented fungus Aspergillus flavus J302-03 led to the isolation of six previously unreported compounds, including four polyketides, aspergullains A–D, and two drimane-type sesquiterpenoids, aspergullains E and F, along with sixteen known compounds. Their structures were characterized through spectroscopic data interpretation, ECD and NMR calculations, DP4+ analysis, and X-ray crystallography. Structurally, aspergullain A was a unique polyketide with a cyclohexanedione−furan hybrid skeleton, while aspergullain B possessed a rare cyclopentenone-tetrahydrofuran moiety. Biologically, aspergullain B, aspergullain C, and aspergullain F exhibited certain antibacterial activities against Pseudomonas syringae pv. actinidiae, with inhibition rates ranging from 70 % to 80 %. Furthermore, aspergullain A and astellolide A exhibited NO production inhibitory effects among tested compounds, with IC50 values of 27.31 ± 2.01 and 21.91 ± 0.87 μM, respectively. The comprehensive data indicated that A. flavus is rich in polyketides and drimane sesquiterpenoids, which have potential antibacterial and anti-inflammatory application prospects.
{"title":"Polyketides and drimane sesquiterpenoids from kiwi plant endophytic fungus Aspergillus flavus J302-03 with antibacterial and anti-inflammatory activities","authors":"Xin-Wen Luo , Fang-Lu Wei , Hong-Fei Li , Jin-Yao Mao , Yan-Ling Yang , Juan He , Tao Feng","doi":"10.1016/j.phytochem.2025.114744","DOIUrl":"10.1016/j.phytochem.2025.114744","url":null,"abstract":"<div><div>The systematic chemical investigation of the ethyl acetate extract of the rice-fermented fungus <em>Aspergillus flavus</em> J302-03 led to the isolation of six previously unreported compounds, including four polyketides, aspergullains A–D, and two drimane-type sesquiterpenoids, aspergullains E and F, along with sixteen known compounds. Their structures were characterized through spectroscopic data interpretation, ECD and NMR calculations, DP4+ analysis, and X-ray crystallography. Structurally, aspergullain A was a unique polyketide with a cyclohexanedione−furan hybrid skeleton, while aspergullain B possessed a rare cyclopentenone-tetrahydrofuran moiety. Biologically, aspergullain B, aspergullain C, and aspergullain F exhibited certain antibacterial activities against <em>Pseudomonas syringae</em> pv. <em>actinidiae</em>, with inhibition rates ranging from 70 % to 80 %. Furthermore, aspergullain A and astellolide A exhibited NO production inhibitory effects among tested compounds, with IC<sub>50</sub> values of 27.31 ± 2.01 and 21.91 ± 0.87 μM, respectively. The comprehensive data indicated that <em>A. flavus</em> is rich in polyketides and drimane sesquiterpenoids, which have potential antibacterial and anti-inflammatory application prospects.</div></div>","PeriodicalId":20170,"journal":{"name":"Phytochemistry","volume":"243 ","pages":"Article 114744"},"PeriodicalIF":3.4,"publicationDate":"2025-12-09","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"145737355","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 : 2025-12-08DOI: 10.1016/j.phytochem.2025.114743
Ling-Ling Yu , Lijin Jiao , Yan-Xi Li , Xu-Hong Li , Shan-Shan Ling , Long-Gao Xiao , Rui-Qi Liu , Wei Ni , Huan Yan , Yunheng Ji , Hai-Yang Liu
Nine previously undescribed oxidized- and hydroxylated-pennogenin saponins, named parisfargosides F–N (1–9), along with fifteen reported analogues, were isolated from the total saponin of Paris fargesii rhizomes with hemostatic activity. Their structures were elucidated by extensive spectroscopic analysis (including HR-ESI-MS, 1D and 2D NMR) and chemical methods. Parisfargoside F (1) has a rare aglycone with a peroxide bridge between C-5/C-8, and parisfargosides G-I (2–4) possess an α, β-unsaturated ketone unit in the B ring. Furthermore, the hemostatic activity of all isolates was evaluated. The results exhibited that six saponins (5, 18, 20–22, and 24) showed platelet aggregation-inducing activity, of which saponin 24 displayed remarkable activity with an EC50 value of 50.1 μM. Additionally, the structure-activity relationships of these isolates were discussed. These results uncovered the hemostatic constituents of P. fargesii.
{"title":"Oxidized- and hydroxylated-pennogenin saponins from the rhizomes of Paris fargesii and their hemostatic activity","authors":"Ling-Ling Yu , Lijin Jiao , Yan-Xi Li , Xu-Hong Li , Shan-Shan Ling , Long-Gao Xiao , Rui-Qi Liu , Wei Ni , Huan Yan , Yunheng Ji , Hai-Yang Liu","doi":"10.1016/j.phytochem.2025.114743","DOIUrl":"10.1016/j.phytochem.2025.114743","url":null,"abstract":"<div><div>Nine previously undescribed oxidized- and hydroxylated-pennogenin saponins, named parisfargosides F–N (<strong>1</strong>–<strong>9</strong>), along with fifteen reported analogues, were isolated from the total saponin of <em>Paris fargesii</em> rhizomes with hemostatic activity. Their structures were elucidated by extensive spectroscopic analysis (including HR-ESI-MS, 1D and 2D NMR) and chemical methods. Parisfargoside F (<strong>1</strong>) has a rare aglycone with a peroxide bridge between C-5/C-8, and parisfargosides G-I (<strong>2</strong>–<strong>4</strong>) possess an <em>α</em>, <em>β</em>-unsaturated ketone unit in the B ring. Furthermore, the hemostatic activity of all isolates was evaluated. The results exhibited that six saponins (<strong>5</strong>, <strong>18</strong>, <strong>20</strong>–<strong>22</strong>, and <strong>24</strong>) showed platelet aggregation-inducing activity, of which saponin <strong>24</strong> displayed remarkable activity with an EC<sub>50</sub> value of 50.1 μM. Additionally, the structure-activity relationships of these isolates were discussed. These results uncovered the hemostatic constituents of <em>P. fargesii</em>.</div></div>","PeriodicalId":20170,"journal":{"name":"Phytochemistry","volume":"243 ","pages":"Article 114743"},"PeriodicalIF":3.4,"publicationDate":"2025-12-08","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"145725055","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 : 2025-12-05DOI: 10.1016/j.phytochem.2025.114742
Mariam G.A. Alex , Seham S. El Hawary , Farouk R. Melek , Amira S. El Senousy , Samar M. Bassam , Mohamed M. Mohyeldin
Crinum L. (Amaryllidaceae) is widely recognized for its ornamental significance and phytochemical richness, particularly its diverse bioactive alkaloids. These alkaloids demonstrate promising anticancer properties, with mechanisms involving the induction of apoptosis, inhibition of tumor proliferation, and suppression of angiogenesis. Studies on Crinum L. species have revealed that bulbs and roots harbor the highest concentrations of bioactive alkaloids, making them the most valuable sources for pharmaceutical applications. These organs are rich in lycorine-, crinine-, and galantamine-type alkaloids, which exhibit potent cytotoxicity against various cancer cell lines. However, only 35 out of 130 Crinum L. species have undergone phytochemical investigation, presenting a considerable research gap. This review examines over 60 Crinum L. species and covers ∼200 alkaloids. It provides a holistic and updated overview of Crinum L. alkaloids from 2013 to 2025, including their biosynthetic pathways, structural classification, and biological activities, with an emphasis on their potential in cancer therapeutics. Additionally, future research directions are proposed, including the development of advanced drug delivery systems, synthetic modifications, and clinical applications, to bridge the gap between phytochemical studies and medical applications.
{"title":"An updated comprehensive review on phytochemical Crinum L. genus alkaloids (2013–2025): Unlocking their anticancer potential","authors":"Mariam G.A. Alex , Seham S. El Hawary , Farouk R. Melek , Amira S. El Senousy , Samar M. Bassam , Mohamed M. Mohyeldin","doi":"10.1016/j.phytochem.2025.114742","DOIUrl":"10.1016/j.phytochem.2025.114742","url":null,"abstract":"<div><div>Crinum L. (Amaryllidaceae) is widely recognized for its ornamental significance and phytochemical richness, particularly its diverse bioactive alkaloids. These alkaloids demonstrate promising anticancer properties, with mechanisms involving the induction of apoptosis, inhibition of tumor proliferation, and suppression of angiogenesis. Studies on <em>Crinum</em> L. species have revealed that bulbs and roots harbor the highest concentrations of bioactive alkaloids, making them the most valuable sources for pharmaceutical applications. These organs are rich in lycorine-<strong>,</strong> crinine-, and galantamine<strong>-</strong>type alkaloids, which exhibit potent cytotoxicity against various cancer cell lines. However, only 35 out of 130 <em>Crinum</em> L. species have undergone phytochemical investigation, presenting a considerable research gap. This review examines over 60 <em>Crinum</em> L. species and covers ∼200 alkaloids. It provides a holistic and updated overview of <em>Crinum</em> L. alkaloids from 2013 to 2025, including their biosynthetic pathways, structural classification, and biological activities, with an emphasis on their potential in cancer therapeutics. Additionally, future research directions are proposed, including the development of advanced drug delivery systems, synthetic modifications, and clinical applications, to bridge the gap between phytochemical studies and medical applications.</div></div>","PeriodicalId":20170,"journal":{"name":"Phytochemistry","volume":"243 ","pages":"Article 114742"},"PeriodicalIF":3.4,"publicationDate":"2025-12-05","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"145701604","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}
Sixteen guaiane-type sesquiterpenoids, including four undescribed 4,5-seco-guaiane derivatives (1–4) and one undescribed guaiane (6), were isolated from the volatile oil of Pogostemon cablin. Their structures were determined using extensive spectroscopic evidence, including NMR, IR, HR-ESI-MS, and ECD calculations. Their anti-depressive effects were evaluated in corticosterone (CORT)-induced PC12 cells in vitro. Compound 5 (7-epi-chabrolidione A) was previously reported by our group to exhibit neuroprotective properties. However, the present study further demonstrated that compounds 1–5 had protective effects against CORT-induced injury in PC12 cells. Hoechst 33258 staining, high-content screening, and western blot analysis revealed that compound 5 activated the CaMKII/CREB/BDNF signaling pathway, thereby reducing apoptosis in CORT-injured PC12 cells and inhibiting intracellular calcium levels. Furthermore, compound 5 effectively rescued reserpine-induced depression and cognitive impairment in zebrafish in vivo. Collectively, these findings indicate that 4,5-seco-guaiane sesquiterpenoids from Pogostemon cablin (especially compound 5) possess potential anti-depressive activity.
{"title":"Guaiane-type sesquiterpenoids from patchouli oil and their potential anti-depressive effects","authors":"Qi Zheng , Huan Zhu , He-ping Yang , Cheng Peng , Guang-xu Wu , Qin-mei Zhou , Liang Xiong","doi":"10.1016/j.phytochem.2025.114738","DOIUrl":"10.1016/j.phytochem.2025.114738","url":null,"abstract":"<div><div>Sixteen guaiane-type sesquiterpenoids, including four undescribed 4,5-<em>seco</em>-guaiane derivatives (<strong>1</strong>–<strong>4</strong>) and one undescribed guaiane (<strong>6</strong>), were isolated from the volatile oil of <em>Pogostemon cablin</em>. Their structures were determined using extensive spectroscopic evidence, including NMR, IR, HR-ESI-MS, and ECD calculations. Their anti-depressive effects were evaluated in corticosterone (CORT)-induced PC12 cells <em>in vitro</em>. Compound <strong>5</strong> (7-epi-chabrolidione A) was previously reported by our group to exhibit neuroprotective properties. However, the present study further demonstrated that compounds <strong>1</strong>–<strong>5</strong> had protective effects against CORT-induced injury in PC12 cells. Hoechst 33258 staining, high-content screening, and western blot analysis revealed that compound <strong>5</strong> activated the CaMKII/CREB/BDNF signaling pathway, thereby reducing apoptosis in CORT-injured PC12 cells and inhibiting intracellular calcium levels. Furthermore, compound <strong>5</strong> effectively rescued reserpine-induced depression and cognitive impairment in zebrafish <em>in vivo</em>. Collectively, these findings indicate that 4,5-<em>seco</em>-guaiane sesquiterpenoids from <em>Pogostemon cablin</em> (especially compound <strong>5</strong>) possess potential anti-depressive activity.</div></div>","PeriodicalId":20170,"journal":{"name":"Phytochemistry","volume":"243 ","pages":"Article 114738"},"PeriodicalIF":3.4,"publicationDate":"2025-12-03","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"145678231","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}
The first phytochemical investigation of the leaves of Fissistigma fulgens (Hook.f. & Thomson) Merr. led to the isolation and identification of five previously undescribed dihydrochalcone derivatives, including two dimeric dihydrochalcones, fissisfulgenones A and B (1 and 2), and three monomeric dihydrochalcones, fissisfulgenones C–E (3–5), along with three known compounds. Their structures were elucidated by spectroscopic analysis. The dimeric structure of fissisfulgenone A (1) was confirmed by single-crystal X-ray diffraction analysis using Cu–Kα radiation. The pure enantiomers of the scalemic mixtures of 1–3 were successfully resolved using chiral-phase HPLC, and their absolute configurations were determined by comparing experimental and calculated ECD spectra. Fissisfulgenones A (1), C (3), and D (4) were evaluated for biological activities, including cytotoxicity against human breast adenocarcinoma (MDA-MB231), human lung carcinoma (A549), human hepatocellular carcinoma (Huh7), and human colorectal adenocarcinoma (SW480 and HT29), antiviral activity against dengue virus (DENV), and nitric oxide production inhibitory activity in LPS-stimulated RAW 264.7 macrophages. Among them, fissisfulgenone C (3) exhibited the highest cytotoxicity against SW480 and HT29 cells with IC50 values of 40.6 and 68.0 μM, respectively, whereas fissisfulgenone D (4) showed cytotoxicity against MDA-MB231, A549, and Huh7 cell lines with IC50 values of 48.7, 38.3, and 21.2 μM, respectively. Notably, fissisfulgenone A (1) significantly reduced virus production in DENV-infected Huh7 cells at a sub-toxic dose of 50.0 μM. Regarding anti-inflammatory activity, fissisfulgenone C (3) exhibited strong nitric oxide inhibition, markedly reducing LPS-induced levels with an IC50 value of 5.27 μM and preserving normal macrophage morphology. Fissisfulgenone A (1) also showed similar effects at lower, non-toxic concentrations.
{"title":"Phytochemical study of Fissistigma fulgens (Hook.f. & Thomson) Merr. leaves: Previously undescribed dihydrochalcone derivatives and their biological activities","authors":"Passakorn Teerapongpisan , Wuttichai Jaidee , Theanchai Wiwasuku , Sarot Cheenpracha , Natcha Injan , Somkiat Nokbin , Kittirat Saharat , Atthapan Morchang , Phateep Hankittichai , Rawiwan Charoensup , Raymond J. Andersen , Surat Laphookhieo","doi":"10.1016/j.phytochem.2025.114735","DOIUrl":"10.1016/j.phytochem.2025.114735","url":null,"abstract":"<div><div>The first phytochemical investigation of the leaves of <em>Fissistigma fulgens</em> (Hook.f. & Thomson) Merr. led to the isolation and identification of five previously undescribed dihydrochalcone derivatives, including two dimeric dihydrochalcones, fissisfulgenones A and B (<strong>1</strong> and <strong>2</strong>), and three monomeric dihydrochalcones, fissisfulgenones C–E (<strong>3</strong>–<strong>5</strong>), along with three known compounds. Their structures were elucidated by spectroscopic analysis. The dimeric structure of fissisfulgenone A (<strong>1</strong>) was confirmed by single-crystal X-ray diffraction analysis using Cu–Kα radiation. The pure enantiomers of the scalemic mixtures of <strong>1</strong>–<strong>3</strong> were successfully resolved using chiral-phase HPLC, and their absolute configurations were determined by comparing experimental and calculated ECD spectra. Fissisfulgenones A (<strong>1</strong>), C (<strong>3</strong>), and D (<strong>4</strong>) were evaluated for biological activities, including cytotoxicity against human breast adenocarcinoma (MDA-MB231), human lung carcinoma (A549), human hepatocellular carcinoma (Huh7), and human colorectal adenocarcinoma (SW480 and HT29), antiviral activity against dengue virus (DENV), and nitric oxide production inhibitory activity in LPS-stimulated RAW 264.7 macrophages. Among them, fissisfulgenone C (<strong>3</strong>) exhibited the highest cytotoxicity against SW480 and HT29 cells with IC<sub>50</sub> values of 40.6 and 68.0 μM, respectively, whereas fissisfulgenone D (<strong>4</strong>) showed cytotoxicity against MDA-MB231, A549, and Huh7 cell lines with IC<sub>50</sub> values of 48.7, 38.3, and 21.2 μM, respectively. Notably, fissisfulgenone A (<strong>1</strong>) significantly reduced virus production in DENV-infected Huh7 cells at a sub-toxic dose of 50.0 μM. Regarding anti-inflammatory activity, fissisfulgenone C (<strong>3</strong>) exhibited strong nitric oxide inhibition, markedly reducing LPS-induced levels with an IC<sub>50</sub> value of 5.27 μM and preserving normal macrophage morphology. Fissisfulgenone A (<strong>1</strong>) also showed similar effects at lower, non-toxic concentrations.</div></div>","PeriodicalId":20170,"journal":{"name":"Phytochemistry","volume":"243 ","pages":"Article 114735"},"PeriodicalIF":3.4,"publicationDate":"2025-12-02","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"145678307","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}
Lethal contagious pathogens wreak havoc on human life and the global economy, especially influenza and other respiratory pathogens, as exemplified by the enduring impact of COVID-19. This study reports that triterpenoids isolated from the stems of medicinal plants Kadsura japonica L. (Schisandraceae), which exhibit potent anti-viral activity against collected influenza viruses. Collectively, four undescribed schitriterpenoids named kadsujanonols J-M (1-4) along with five previously reported, schincarin D (5), ananosin E (6), changnanic acid (7), longipedlactone A (8), and schiglansin S (9), were isolated and identified. Their chemical structures were determined using 1H-, 13C-, and 2D-NMR spectra in conjunction with spectroscopic analyses, such as UV, IR, ECD, and HRESIMS. These schitriterpenoids were then subjected to antiviral examination against the collected H1N1 influenza viruses, in which several, changnanic acid (7) in particular, unveiled excellent anti-H1N1 activity compared to Tamiflu.
{"title":"Potential anti-H1N1 schitriterpenoids from Kadsura japonica L. vines.","authors":"Hung-Tse Huang, Chun-Tang Chiou, Yu-Chi Lin, Li-Jie Zhang, Chih-Hua Chao, Ping-Jyun Sung, Jih-Jung Chen, Tsung-Lin Li, I-Wen Lo, Chia-Ching Liaw","doi":"10.1016/j.phytochem.2025.114632","DOIUrl":"10.1016/j.phytochem.2025.114632","url":null,"abstract":"<p><p>Lethal contagious pathogens wreak havoc on human life and the global economy, especially influenza and other respiratory pathogens, as exemplified by the enduring impact of COVID-19. This study reports that triterpenoids isolated from the stems of medicinal plants Kadsura japonica L. (Schisandraceae), which exhibit potent anti-viral activity against collected influenza viruses. Collectively, four undescribed schitriterpenoids named kadsujanonols J-M (1-4) along with five previously reported, schincarin D (5), ananosin E (6), changnanic acid (7), longipedlactone A (8), and schiglansin S (9), were isolated and identified. Their chemical structures were determined using <sup>1</sup>H-, <sup>13</sup>C-, and 2D-NMR spectra in conjunction with spectroscopic analyses, such as UV, IR, ECD, and HRESIMS. These schitriterpenoids were then subjected to antiviral examination against the collected H1N1 influenza viruses, in which several, changnanic acid (7) in particular, unveiled excellent anti-H1N1 activity compared to Tamiflu.</p>","PeriodicalId":20170,"journal":{"name":"Phytochemistry","volume":" ","pages":"114632"},"PeriodicalIF":3.4,"publicationDate":"2025-12-01","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"144817267","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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