Pub Date : 2025-10-27DOI: 10.1016/j.phytol.2025.104064
Hao Gong , Kuan Lin , Lei Zhang , Yi Huang , Li-Juan Hu , Xiao-Ya Liu , Hao Ming , Si-Qi Wang , Qing-Qin He , Xian-Sheng Ye , Shu-Xiu Zhu
Two new sesquiterpene lactones, namely yjaponica D (1) and E (2), along with five known analogs, were isolated from Youngia japonica. Their structures were elucidated by NMR, HRESIMS, ECD and calculated ECD. The cytotoxic activities of all compounds against A549, GL261, U87, and HeLa cell lines were detected by a CCK-8 assay, and the apoptosis-inducing effects and regulation of cancer-related proteins in A549 cells by compound 2 were evaluated. Results showed that compound 2 exhibited distinct cytotoxic activity against A549 cells and induced the apoptosis of A549 cells. Western blotting results showed that compound 2 significantly upregulated the expression of p-JNK, p-ERK, and Bax, while downregulating the expression of p-AKT, p-p38, and Bcl-2 in A549 cells. Collectively, compound 2 shows potential as a lead candidate for further development in lung cancer treatments.
{"title":"Bioactive sesquiterpene lactones with cytotoxic activity from Youngia japonica","authors":"Hao Gong , Kuan Lin , Lei Zhang , Yi Huang , Li-Juan Hu , Xiao-Ya Liu , Hao Ming , Si-Qi Wang , Qing-Qin He , Xian-Sheng Ye , Shu-Xiu Zhu","doi":"10.1016/j.phytol.2025.104064","DOIUrl":"10.1016/j.phytol.2025.104064","url":null,"abstract":"<div><div>Two new sesquiterpene lactones, namely yjaponica D (<strong>1</strong>) and E (<strong>2</strong>), along with five known analogs, were isolated from <em>Youngia japonica</em>. Their structures were elucidated by NMR, HRESIMS, ECD and calculated ECD. The cytotoxic activities of all compounds against A549, GL261, U87, and HeLa cell lines were detected by a CCK-8 assay, and the apoptosis-inducing effects and regulation of cancer-related proteins in A549 cells by compound <strong>2</strong> were evaluated. Results showed that compound <strong>2</strong> exhibited distinct cytotoxic activity against A549 cells and induced the apoptosis of A549 cells. Western blotting results showed that compound <strong>2</strong> significantly upregulated the expression of p-JNK, p-ERK, and Bax, while downregulating the expression of p-AKT, p-p38, and Bcl-2 in A549 cells. Collectively, compound <strong>2</strong> shows potential as a lead candidate for further development in lung cancer treatments.</div></div>","PeriodicalId":20408,"journal":{"name":"Phytochemistry Letters","volume":"70 ","pages":"Article 104064"},"PeriodicalIF":1.4,"publicationDate":"2025-10-27","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"145417139","PeriodicalName":null,"FirstCategoryId":null,"ListUrlMain":null,"RegionNum":4,"RegionCategory":"生物学","ArticlePicture":[],"TitleCN":null,"AbstractTextCN":null,"PMCID":"","EPubDate":null,"PubModel":null,"JCR":null,"JCRName":null,"Score":null,"Total":0}
Pub Date : 2025-10-24DOI: 10.1016/j.phytol.2025.104065
Nai-Dong Li , Cheng-Shan Wei , Chun-Xia Song , Chun-Jiang Du , Juan Xu
Two previously unreported aromatic natural products, toonasinetin A (1) and toonasinetin B (2), along with three known compounds (3–5), were isolated from the methanolic extracts of the branches and leaves of Toona sinensis. The chemical structures of compounds 1 and 2 were established by 1D, 2D NMR, HRESIMS, UV, IR analysis, and calculating electronic circular dichroism (ECD). The structures of known compounds 3–5 were determined by comparison of their spectral data with those reported in the literature. These findings expand the known phytochemical diversity of this species and contribute to its chemotaxonomic characterization.
{"title":"Toonasinetins A and B, two new compounds from the branches and leaves of Toona sinensis","authors":"Nai-Dong Li , Cheng-Shan Wei , Chun-Xia Song , Chun-Jiang Du , Juan Xu","doi":"10.1016/j.phytol.2025.104065","DOIUrl":"10.1016/j.phytol.2025.104065","url":null,"abstract":"<div><div>Two previously unreported aromatic natural products, toonasinetin A (1) and toonasinetin B (2), along with three known compounds (3–5), were isolated from the methanolic extracts of the branches and leaves of <em>Toona sinensis</em>. The chemical structures of compounds 1 and 2 were established by 1D, 2D NMR, HRESIMS, UV, IR analysis, and calculating electronic circular dichroism (ECD). The structures of known compounds 3–5 were determined by comparison of their spectral data with those reported in the literature. These findings expand the known phytochemical diversity of this species and contribute to its chemotaxonomic characterization.</div></div>","PeriodicalId":20408,"journal":{"name":"Phytochemistry Letters","volume":"70 ","pages":"Article 104065"},"PeriodicalIF":1.4,"publicationDate":"2025-10-24","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"145363271","PeriodicalName":null,"FirstCategoryId":null,"ListUrlMain":null,"RegionNum":4,"RegionCategory":"生物学","ArticlePicture":[],"TitleCN":null,"AbstractTextCN":null,"PMCID":"","EPubDate":null,"PubModel":null,"JCR":null,"JCRName":null,"Score":null,"Total":0}
Pub Date : 2025-10-23DOI: 10.1016/j.phytol.2025.104059
Sabry A.H. Zidan , Mostafa A. Asmaey , Mohamed R. Kamel , Eman Fawzy El Azab , Saleha Y.M. Alakilli , Mohamed N. Ibrahim , Mohamed A. Tantawy , Khaled M. Elokely , Katsuyoshi Matsunami , Waleed A. Abdel-Naime
In this study, a cytotoxicity-guided isolation approach was employed to isolate bioactive compounds from the crude extract of the Red Sea soft coral Sarcophyton ehrenbergi (S. ehrenbergi). The isolated compounds were tested against A549 and HepG2 cancer cell lines using the MTT colorimetric assay. This process led to the discovery of a new butanolide derivative (1), along with three known related metabolites (2, 3, and 4), as well as two steroids (5 and 6) from the most active ethyl acetate (EtOAc) fraction. The structures of these compounds were determined through comprehensive NMR spectroscopic analyses, HRESI-MS, and comparison with previously reported data. In bioassays, compound 5 demonstrated potent cytotoxicity against HepG2 cells, whereas compound 6 exhibited noticeable activity against A549 cells, comparable to that of etoposide. Molecular docking studies revealed a strong binding affinity of compounds 5 and 6 to the active site of potential targeted enzymes, highlighting their mechanisms of action. However, the isolated compounds did not display any anti-leishmanial activity against Leishmania major. This research provides valuable insights into the bioactive compounds of S. ehrenbergi and their potential as anticancer agents. Further studies are recommended to validate these findings in vivo.
{"title":"Bioactive butanolides and steroids from the Red Sea soft coral Sarcophyton ehrenbergi","authors":"Sabry A.H. Zidan , Mostafa A. Asmaey , Mohamed R. Kamel , Eman Fawzy El Azab , Saleha Y.M. Alakilli , Mohamed N. Ibrahim , Mohamed A. Tantawy , Khaled M. Elokely , Katsuyoshi Matsunami , Waleed A. Abdel-Naime","doi":"10.1016/j.phytol.2025.104059","DOIUrl":"10.1016/j.phytol.2025.104059","url":null,"abstract":"<div><div>In this study, a cytotoxicity-guided isolation approach was employed to isolate bioactive compounds from the crude extract of the Red Sea soft coral <em>Sarcophyton ehrenbergi</em> (<em>S. ehrenbergi</em>). The isolated compounds were tested against A549 and HepG2 cancer cell lines using the MTT colorimetric assay. This process led to the discovery of a new butanolide derivative (<strong>1</strong>), along with three known related metabolites (<strong>2</strong>, <strong>3</strong>, and <strong>4</strong>), as well as two steroids (<strong>5</strong> and <strong>6</strong>) from the most active ethyl acetate (EtOAc) fraction. The structures of these compounds were determined through comprehensive NMR spectroscopic analyses, HRESI-MS, and comparison with previously reported data. In bioassays, compound <strong>5</strong> demonstrated potent cytotoxicity against HepG2 cells, whereas compound <strong>6</strong> exhibited noticeable activity against A549 cells, comparable to that of etoposide. Molecular docking studies revealed a strong binding affinity of compounds <strong>5</strong> and <strong>6</strong> to the active site of potential targeted enzymes, highlighting their mechanisms of action. However, the isolated compounds did not display any anti-leishmanial activity against <em>Leishmania major</em>. This research provides valuable insights into the bioactive compounds of <em>S. ehrenbergi</em> and their potential as anticancer agents. Further studies are recommended to validate these findings <em>in vivo</em>.</div></div>","PeriodicalId":20408,"journal":{"name":"Phytochemistry Letters","volume":"70 ","pages":"Article 104059"},"PeriodicalIF":1.4,"publicationDate":"2025-10-23","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"145363267","PeriodicalName":null,"FirstCategoryId":null,"ListUrlMain":null,"RegionNum":4,"RegionCategory":"生物学","ArticlePicture":[],"TitleCN":null,"AbstractTextCN":null,"PMCID":"","EPubDate":null,"PubModel":null,"JCR":null,"JCRName":null,"Score":null,"Total":0}
Pub Date : 2025-10-22DOI: 10.1016/j.phytol.2025.104063
Rodrigo A. Contreras, Marisol Pizarro, Pablo Zamora , Gustavo E. Zúñiga
Lichens are symbiotic organisms that inhabit all climate zones of this planet, including even those in Antarctica, thanks to their sophisticated biochemical machinery. This study investigated the phytochemical composition of three lichen species (Pleopsidium sp., Sarcogyne sp., and Rusavskia sp.) collected from Mount Rossman, Antarctica. We used liquid chromatography coupled with tandem mass spectrometry (LC-MS/MS) to putatively assign key secondary metabolites, including anthraquinones and various depsides and depsidones, important for UV protection and antimicrobial defense. We also quantified the lichens’ sugar profiles by high-performance liquid chromatography with refractive index detection (HPLC-RID) using external standards. Here, we provide new perspectives on how these lichens utilize metabolic strategies to survive under extreme desiccation conditions in their terrestrial environment and highlight their biotechnological and pharmaceutical applications.
{"title":"Phytochemistry of crustose lichens from Mount Rossman, Ellsworth Land, Antarctica","authors":"Rodrigo A. Contreras, Marisol Pizarro, Pablo Zamora , Gustavo E. Zúñiga","doi":"10.1016/j.phytol.2025.104063","DOIUrl":"10.1016/j.phytol.2025.104063","url":null,"abstract":"<div><div>Lichens are symbiotic organisms that inhabit all climate zones of this planet, including even those in Antarctica, thanks to their sophisticated biochemical machinery. This study investigated the phytochemical composition of three lichen species (<em>Pleopsidium</em> sp., <em>Sarcogyne</em> sp., and <em>Rusavskia</em> sp.) collected from Mount Rossman, Antarctica. We used liquid chromatography coupled with tandem mass spectrometry (LC-MS/MS) to putatively assign key secondary metabolites, including anthraquinones and various depsides and depsidones, important for UV protection and antimicrobial defense. We also quantified the lichens’ sugar profiles by high-performance liquid chromatography with refractive index detection (HPLC-RID) using external standards. Here, we provide new perspectives on how these lichens utilize metabolic strategies to survive under extreme desiccation conditions in their terrestrial environment and highlight their biotechnological and pharmaceutical applications.</div></div>","PeriodicalId":20408,"journal":{"name":"Phytochemistry Letters","volume":"70 ","pages":"Article 104063"},"PeriodicalIF":1.4,"publicationDate":"2025-10-22","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"145363270","PeriodicalName":null,"FirstCategoryId":null,"ListUrlMain":null,"RegionNum":4,"RegionCategory":"生物学","ArticlePicture":[],"TitleCN":null,"AbstractTextCN":null,"PMCID":"","EPubDate":null,"PubModel":null,"JCR":null,"JCRName":null,"Score":null,"Total":0}
Pub Date : 2025-10-22DOI: 10.1016/j.phytol.2025.104062
Lirong Zheng , Jianguo Sun , Ruifen Zhang , Huan Li , Tingting Jia , Hairong Zhang , He Su
Hypoxia/Reoxygenation (H/R)-induced cardiomyocyte injury is the primary cause of Myocardial ischemia-reperfusion injury (MI/R injury), and protecting cardiomyocyte is an effective therapeutic strategy for MI/R injury. The Dangong-3 (DG3) is a common Mongolian medicine that exhibits a beneficial protective effect on cardiomyocytes, but the underlying mechanisms and key compounds of DG3 in protecting against H/R-mediated cardiomyocyte injury remain unclear. First, a total of 36 compounds of DG3 were identified by UPLC-Q-TOF-MS/MS analysis, and 306 potential targets of DG3 in protecting against H/R-mediated cardiomyocyte injury were screened out through network pharmacology. Moreover, protein-protein interaction analysis highlighted COX-2 as core target through which DG3 ameliorates H/R- induced cardiomyocyte injury, and KEGG enrichment analysis revealed that the AGE-RAGE signaling pathway plays a crucial role. Molecular docking was employed to screen key compounds of DG3 for protecting against H/R-induced cardiomyocyte injury, and compounds binding with core targets were validated by CETSA assay. The results showed 3,4-Dicaffeoylquinic acid, i.e. isochlorogenic acid B (ICha B), can bind well with COX-2 and may be the key compound of DG3. The CETSA assay also confirmed that ICha B can target COX-2. Western blotting indicated that ICha B exerts cardioprotective effects by suppressing the RAGE signaling pathway. In summary, we discovered that ICha B was the key compound of DG3, which can target and inhibit COX-2 to protect against H/R-induced cardiomyocyte injury by suppressing RAGE signaling pathway. These findings provide data support for further research and application of DG3 in the treatment of MI/R injury.
{"title":"Isochlorogenic acid B targets COX-2 to protect against Hypoxia/Reoxygenation-induced cardiomyocyte injury through the RAGE signaling pathway","authors":"Lirong Zheng , Jianguo Sun , Ruifen Zhang , Huan Li , Tingting Jia , Hairong Zhang , He Su","doi":"10.1016/j.phytol.2025.104062","DOIUrl":"10.1016/j.phytol.2025.104062","url":null,"abstract":"<div><div>Hypoxia/Reoxygenation (H/R)-induced cardiomyocyte injury is the primary cause of Myocardial ischemia-reperfusion injury (MI/R injury), and protecting cardiomyocyte is an effective therapeutic strategy for MI/R injury. The Dangong-3 (DG3) is a common Mongolian medicine that exhibits a beneficial protective effect on cardiomyocytes, but the underlying mechanisms and key compounds of DG3 in protecting against H/R-mediated cardiomyocyte injury remain unclear. First, a total of 36 compounds of DG3 were identified by UPLC-Q-TOF-MS/MS analysis, and 306 potential targets of DG3 in protecting against H/R-mediated cardiomyocyte injury were screened out through network pharmacology. Moreover, protein-protein interaction analysis highlighted COX-2 as core target through which DG3 ameliorates H/R- induced cardiomyocyte injury, and KEGG enrichment analysis revealed that the AGE-RAGE signaling pathway plays a crucial role. Molecular docking was employed to screen key compounds of DG3 for protecting against H/R-induced cardiomyocyte injury, and compounds binding with core targets were validated by CETSA assay. The results showed 3,4-Dicaffeoylquinic acid, i.e. isochlorogenic acid B (ICha B), can bind well with COX-2 and may be the key compound of DG3. The CETSA assay also confirmed that ICha B can target COX-2. Western blotting indicated that ICha B exerts cardioprotective effects by suppressing the RAGE signaling pathway. In summary, we discovered that ICha B was the key compound of DG3, which can target and inhibit COX-2 to protect against H/R-induced cardiomyocyte injury by suppressing RAGE signaling pathway. These findings provide data support for further research and application of DG3 in the treatment of MI/R injury.</div></div>","PeriodicalId":20408,"journal":{"name":"Phytochemistry Letters","volume":"70 ","pages":"Article 104062"},"PeriodicalIF":1.4,"publicationDate":"2025-10-22","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"145363268","PeriodicalName":null,"FirstCategoryId":null,"ListUrlMain":null,"RegionNum":4,"RegionCategory":"生物学","ArticlePicture":[],"TitleCN":null,"AbstractTextCN":null,"PMCID":"","EPubDate":null,"PubModel":null,"JCR":null,"JCRName":null,"Score":null,"Total":0}
Pub Date : 2025-10-21DOI: 10.1016/j.phytol.2025.104061
Pham Thi Mai Huong , Pham Thi Cham , Le Thi Vien , Tran Thi Hong Hanh , Nguyen The Cuong , Nguyen Xuan Cuong , Nguyen Hoai Nam
Phytochemical study of Smallanthus sonchifolius tubers led to the isolation of seven ent-kaurane derivatives, including three new compounds, namely sonchifoliosides A−C (1−3). Their structures were confirmed by a detailed analysis of the 1D and 2D NMR and HR-ESI-QTOF mass spectra. Among the isolates, 16α,17,19-trihydroxy-ent-kaurane 19-O-β-D-glucopyranoside (5) exhibited α-glucosidase inhibitory activity with an IC50 value of 104.71 ± 0.45 μM.
{"title":"ent-Kaurane derivatives from Smallanthus sonchifolius","authors":"Pham Thi Mai Huong , Pham Thi Cham , Le Thi Vien , Tran Thi Hong Hanh , Nguyen The Cuong , Nguyen Xuan Cuong , Nguyen Hoai Nam","doi":"10.1016/j.phytol.2025.104061","DOIUrl":"10.1016/j.phytol.2025.104061","url":null,"abstract":"<div><div>Phytochemical study of <em>Smallanthus sonchifolius</em> tubers led to the isolation of seven <em>ent</em>-kaurane derivatives, including three new compounds, namely sonchifoliosides A−C (<strong>1</strong>−<strong>3</strong>). Their structures were confirmed by a detailed analysis of the 1D and 2D NMR and HR-ESI-QTOF mass spectra. Among the isolates, 16<em>α</em>,17,19-trihydroxy-<em>ent</em>-kaurane 19-<em>O</em>-<em>β</em>-D-glucopyranoside (<strong>5</strong>) exhibited α-glucosidase inhibitory activity with an IC<sub>50</sub> value of 104.71 ± 0.45 μM.</div></div>","PeriodicalId":20408,"journal":{"name":"Phytochemistry Letters","volume":"70 ","pages":"Article 104061"},"PeriodicalIF":1.4,"publicationDate":"2025-10-21","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"145363269","PeriodicalName":null,"FirstCategoryId":null,"ListUrlMain":null,"RegionNum":4,"RegionCategory":"生物学","ArticlePicture":[],"TitleCN":null,"AbstractTextCN":null,"PMCID":"","EPubDate":null,"PubModel":null,"JCR":null,"JCRName":null,"Score":null,"Total":0}
Pub Date : 2025-10-18DOI: 10.1016/j.phytol.2025.104048
Chao-Yuan Xiao , Zhi-You Hao , Meng Yang , Qi-Mei Tie , Jun-Yang Zhang , Xu-Dong Ma , Xiao Ke Zheng , Yan-Jun Sun , Wei-Sheng Feng
Three previously undescribed compounds, including one pregnane steroid (1), one isoflavone (2), one diketopiperazine (3), along with eight known ones (4–11) were isolated from Poria cocos. The structural elucidation was accomplished through comprehensive spectroscopic analysis, while the absolute configurations were unequivocally established by correlating experimental ECD spectra with quantum chemically calculated spectra. The isolated compounds were screened for in vitro anti-asthmatic activity by assessing their inhibitory effects on C48/80-induced degranulation in RBL-2H3 mast cells. The results showed compounds 2 and 4–10 significantly inhibited the release of β-Hexosaminidase (β-Hex) (P < 0.01) and attenuated the degranulation process in RBL-2H3 cells at 10.0 μM. It is proposed that they may exert anti-asthmatic effects by inhibiting mast cell degranulation.
{"title":"In vitro anti-asthmatic activities of phytochemicals isolated from Poria cocos","authors":"Chao-Yuan Xiao , Zhi-You Hao , Meng Yang , Qi-Mei Tie , Jun-Yang Zhang , Xu-Dong Ma , Xiao Ke Zheng , Yan-Jun Sun , Wei-Sheng Feng","doi":"10.1016/j.phytol.2025.104048","DOIUrl":"10.1016/j.phytol.2025.104048","url":null,"abstract":"<div><div>Three previously undescribed compounds, including one pregnane steroid (<strong>1</strong>), one isoflavone (<strong>2</strong>), one diketopiperazine (<strong>3</strong>), along with eight known ones (<strong>4–11</strong>) were isolated from <em>Poria cocos</em>. The structural elucidation was accomplished through comprehensive spectroscopic analysis, while the absolute configurations were unequivocally established by correlating experimental ECD spectra with quantum chemically calculated spectra. The isolated compounds were screened for in vitro <em>anti</em>-asthmatic activity by assessing their inhibitory effects on C48/80-induced degranulation in RBL-2H3 mast cells. The results showed compounds <strong>2</strong> and <strong>4–10</strong> significantly inhibited the release of <em>β</em>-Hexosaminidase (<em>β</em>-Hex) (<em>P</em> < 0.01) and attenuated the degranulation process in RBL-2H3 cells at 10.0 <em>μ</em>M. It is proposed that they may exert <em>anti</em>-asthmatic effects by inhibiting mast cell degranulation.</div></div>","PeriodicalId":20408,"journal":{"name":"Phytochemistry Letters","volume":"70 ","pages":"Article 104048"},"PeriodicalIF":1.4,"publicationDate":"2025-10-18","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"145321913","PeriodicalName":null,"FirstCategoryId":null,"ListUrlMain":null,"RegionNum":4,"RegionCategory":"生物学","ArticlePicture":[],"TitleCN":null,"AbstractTextCN":null,"PMCID":"","EPubDate":null,"PubModel":null,"JCR":null,"JCRName":null,"Score":null,"Total":0}
Pub Date : 2025-10-17DOI: 10.1016/j.phytol.2025.104058
Theresa Bayerl , Veronika R. Huber , Herbert Riepl , Corinna Urmann
The flavonoid class encompasses over 700 distinct structural variants, all of which have been demonstrated to confer a multitude of beneficial effects on human health. Given the correlation between oxidative stress and over 100 diseases, including neurodegenerative, cardiovascular, and inflammatory diseases, it is a valuable target for the development of therapeutic agents. This study examined the effects of prenylated chalcones and flavanones derived from hops (Humulus lupulus L.), including xanthohumol, xanthohumol A, and C, as well as isoxanthohumol, 6- and 8-prenylnaringenin, and 8-geranylnaringenin, on cell viability and on revising the effect of sodium nitroprusside (SNP) on cell viability in the neuroblastoma cell line SH-SY5Y. The lowest IC50 (10.14–20.42 µM) was observed in treatment with chalcones. With regard to the protective effect against SNP, a structure-activity relationship of prenylated and geranylated flavanones indicated that the extension of the prenyl side chain is beneficial for the protective effect of prenylated flavanones against SNP treatment. In accordance with the aforementioned methodology, 8-farnesylnaringenin, comprising a chain of three isoprene units, was synthesized and the effect on cell viability and protection against SNP-induced reduction of cell viability was subsequently evaluated. The strongest impact on cell viability (IC50) was observed for 8-farnesylnaringenin, which also demonstrated the most robust protective effect (25 %).
{"title":"Effects of prenylflavonoids from hops against sodium nitroprusside-induced cell viability reduction in SH-SY5Y cells: Role of side chain length","authors":"Theresa Bayerl , Veronika R. Huber , Herbert Riepl , Corinna Urmann","doi":"10.1016/j.phytol.2025.104058","DOIUrl":"10.1016/j.phytol.2025.104058","url":null,"abstract":"<div><div>The flavonoid class encompasses over 700 distinct structural variants, all of which have been demonstrated to confer a multitude of beneficial effects on human health. Given the correlation between oxidative stress and over 100 diseases, including neurodegenerative, cardiovascular, and inflammatory diseases, it is a valuable target for the development of therapeutic agents. This study examined the effects of prenylated chalcones and flavanones derived from hops (<em>Humulus lupulus</em> L.), including xanthohumol, xanthohumol A, and C, as well as isoxanthohumol, 6- and 8-prenylnaringenin, and 8-geranylnaringenin, on cell viability and on revising the effect of sodium nitroprusside (SNP) on cell viability in the neuroblastoma cell line SH-SY5Y. The lowest IC<sub>50</sub> (10.14–20.42 µM) was observed in treatment with chalcones. With regard to the protective effect against SNP, a structure-activity relationship of prenylated and geranylated flavanones indicated that the extension of the prenyl side chain is beneficial for the protective effect of prenylated flavanones against SNP treatment. In accordance with the aforementioned methodology, 8-farnesylnaringenin, comprising a chain of three isoprene units, was synthesized and the effect on cell viability and protection against SNP-induced reduction of cell viability was subsequently evaluated. The strongest impact on cell viability (IC<sub>50</sub>) was observed for 8-farnesylnaringenin, which also demonstrated the most robust protective effect (25 %).</div></div>","PeriodicalId":20408,"journal":{"name":"Phytochemistry Letters","volume":"70 ","pages":"Article 104058"},"PeriodicalIF":1.4,"publicationDate":"2025-10-17","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"145321914","PeriodicalName":null,"FirstCategoryId":null,"ListUrlMain":null,"RegionNum":4,"RegionCategory":"生物学","ArticlePicture":[],"TitleCN":null,"AbstractTextCN":null,"PMCID":"","EPubDate":null,"PubModel":null,"JCR":null,"JCRName":null,"Score":null,"Total":0}
Pub Date : 2025-10-17DOI: 10.1016/j.phytol.2025.104050
Chi-I. Chang , Yih-Fwu Chan , Ching-Chuan Kuo , Yueh-Hsiung Kuo
Three new ent-17-norkaurane diterpenoids, ent-19-acetoxy-17-norkauran-16-one (1), ent-19-(Z)-coumaroyloxy-17-norkauran-16-one (2), and ent-19-(E)-coumaroyloxy-17-norkauran-16-one (3), along with one known ent-17-norkaurane diterpenoid, ent-17-norkauran-16α-ol (4), were isolated from the leaves of Chamaecyparis obtusa var. formosana. Their structures were elucidated by 1D and 2D NMR (1H, 13C, COSY, HSQC, HMBC, and NOESY) and HR-EI-MS spectroscopic analysis and comparison of spectral data with those of known analogues. Compounds 2 and 3 were evaluated for their cytotoxic activity against HONE-1 human carcinoma cell lines and exhibited significant activity, with IC₅₀ values of 9.1 and 12.4 µM, respectively.
{"title":"Three new ent-17-norkaurane diterpenoids from the leaves of Chamaecyparis obtusa var. formosana and their cytotoxic activity against HONE-1 human carcinoma cell lines","authors":"Chi-I. Chang , Yih-Fwu Chan , Ching-Chuan Kuo , Yueh-Hsiung Kuo","doi":"10.1016/j.phytol.2025.104050","DOIUrl":"10.1016/j.phytol.2025.104050","url":null,"abstract":"<div><div>Three new <em>ent</em>-17-norkaurane diterpenoids, <em>ent</em>-19-acetoxy-17-norkauran-16-one (<strong>1</strong>), <em>ent</em>-19-(<em>Z</em>)-coumaroyloxy-17-norkauran-16-one (<strong>2</strong>), and <em>ent</em>-19-(<em>E</em>)-coumaroyloxy-17-norkauran-16-one (<strong>3</strong>), along with one known <em>ent</em>-17-norkaurane diterpenoid, <em>ent</em>-17-norkauran-16α-ol (<strong>4</strong>), were isolated from the leaves of <em>Chamaecyparis obtusa</em> var. <em>formosana</em>. Their structures were elucidated by 1D and 2D NMR (<sup>1</sup>H, <sup>13</sup>C, COSY, HSQC, HMBC, and NOESY) and HR-EI-MS spectroscopic analysis and comparison of spectral data with those of known analogues. Compounds <strong>2</strong> and <strong>3</strong> were evaluated for their cytotoxic activity against HONE-1 human carcinoma cell lines and exhibited significant activity, with IC₅₀ values of 9.1 and 12.4 µM, respectively.</div></div>","PeriodicalId":20408,"journal":{"name":"Phytochemistry Letters","volume":"70 ","pages":"Article 104050"},"PeriodicalIF":1.4,"publicationDate":"2025-10-17","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"145321911","PeriodicalName":null,"FirstCategoryId":null,"ListUrlMain":null,"RegionNum":4,"RegionCategory":"生物学","ArticlePicture":[],"TitleCN":null,"AbstractTextCN":null,"PMCID":"","EPubDate":null,"PubModel":null,"JCR":null,"JCRName":null,"Score":null,"Total":0}
One new aryltetralin lignan, blachianol D (1), together with other six known compounds (2–7) were isolated from the stems of Blachia pentzii (Euphorbiaceae) for the first time. Their structures were identified by spectroscopic analyses, especially 1D, 2D NMR, and ECD calculations for 1. Compound 1 was further evaluated for anti-inflammatory activities that reduced LPS-induced NO production of RAW 264.7 cells. In addition, 1 could match well in the binding pocket of ABCG2 protein by molecular docking. Although 1 did not exert anti-inflammatory activity, it could find application in other fields of medicine as a potential inhibitor of ABCG2.
{"title":"One new aryltetralin lignan and other components from Blachia pentzii","authors":"Yan-Yan Zhang , Feng-Cheng Zhang , Yue Zhang , Hong-Yan Yu , Hai-Rong Xu , Xiao-Yun Dong , Chang-Shui Yang","doi":"10.1016/j.phytol.2025.104057","DOIUrl":"10.1016/j.phytol.2025.104057","url":null,"abstract":"<div><div>One new aryltetralin lignan, blachianol D (1), together with other six known compounds (2–7) were isolated from the stems of <em>Blachia pentzii</em> (Euphorbiaceae) for the first time. Their structures were identified by spectroscopic analyses, especially 1D, 2D NMR, and ECD calculations for 1. Compound 1 was further evaluated for anti-inflammatory activities that reduced LPS-induced NO production of RAW 264.7 cells. In addition, 1 could match well in the binding pocket of ABCG2 protein by molecular docking. Although 1 did not exert anti-inflammatory activity, it could find application in other fields of medicine as a potential inhibitor of ABCG2.</div></div>","PeriodicalId":20408,"journal":{"name":"Phytochemistry Letters","volume":"70 ","pages":"Article 104057"},"PeriodicalIF":1.4,"publicationDate":"2025-10-16","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"145321912","PeriodicalName":null,"FirstCategoryId":null,"ListUrlMain":null,"RegionNum":4,"RegionCategory":"生物学","ArticlePicture":[],"TitleCN":null,"AbstractTextCN":null,"PMCID":"","EPubDate":null,"PubModel":null,"JCR":null,"JCRName":null,"Score":null,"Total":0}
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