Basidiomycetes with a wide variety of skeletons of secondary metabolites can be expected to be the source of new interesting biological compounds. During our research on basidiomycetes, two new C-29 oxygenated oleanane-type triterpenes (1 and 2) and torulosacid (3), a muurolene type sesquiterpenoid with a five-membered ether ring along with nine known compounds (4–12), were isolated from the MeOH extract of the fruiting bodies of Fuscoporia torulosa. The structures of 1–3 were determined by NMR and HREIMS analysis. Further studies on the stereochemistry of 3 were conducted using X-ray crystallographic analysis and comparison of experimental and calculated ECD spectra. In the antimicrobial assay of isolates, 1, 7, and 9 showed growth inhibitory activity against methicillin-resistant Staphylococcus aureus and other gram-positive strains. Isolation of oleanane type triterpenes from fungi including basidiomycetes, is a unique report that could lead to further isolation of new compounds and the discovery of unique biosynthetic enzymes.
{"title":"Isolation of C-29 oxygenated oleanane triterpenoids and a (+)-muurolene type sesquiterpenoid from the fruiting bodies of Fuscoporia torulosa and their bioactivities","authors":"Tatsuro Yoneyama, Chian Chen, Yoshihiro Ichimura, Katsuyuki Nakashima, Hiromichi Kenmoku, Hiroshi Imagawa, Akemi Umeyama, Masaaki Noji","doi":"10.1007/s11418-024-01832-z","DOIUrl":"10.1007/s11418-024-01832-z","url":null,"abstract":"<div><p>Basidiomycetes with a wide variety of skeletons of secondary metabolites can be expected to be the source of new interesting biological compounds. During our research on basidiomycetes, two new C-29 oxygenated oleanane-type triterpenes (<b>1</b> and <b>2</b>) and torulosacid (<b>3</b>), a muurolene type sesquiterpenoid with a five-membered ether ring along with nine known compounds (<b>4</b>–<b>12</b>), were isolated from the MeOH extract of the fruiting bodies of <i>Fuscoporia torulosa</i>. The structures of <b>1</b>–<b>3</b> were determined by NMR and HREIMS analysis. Further studies on the stereochemistry of <b>3</b> were conducted using X-ray crystallographic analysis and comparison of experimental and calculated ECD spectra. In the antimicrobial assay of isolates, <b>1</b>,<b> 7</b>, and <b>9</b> showed growth inhibitory activity against methicillin-resistant <i>Staphylococcus aureus</i> and other gram-positive strains. Isolation of oleanane type triterpenes from fungi including basidiomycetes, is a unique report that could lead to further isolation of new compounds and the discovery of unique biosynthetic enzymes.</p><h3>Graphical abstract</h3><div><figure><div><div><picture><source><img></source></picture></div></div></figure></div></div>","PeriodicalId":654,"journal":{"name":"Journal of Natural Medicines","volume":"78 4","pages":"919 - 928"},"PeriodicalIF":2.5,"publicationDate":"2024-08-10","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"141911310","PeriodicalName":null,"FirstCategoryId":null,"ListUrlMain":null,"RegionNum":4,"RegionCategory":"医学","ArticlePicture":[],"TitleCN":null,"AbstractTextCN":null,"PMCID":"","EPubDate":null,"PubModel":null,"JCR":null,"JCRName":null,"Score":null,"Total":0}
Phytochemical study on the flowers of Hypericum formosanum Maxim. (Hypericaceae) led to the isolation of formohyperins G–L (1–6), whose structures were assigned by detailed spectroscopic analysis. Formohyperins G–L (1–6) are new benzoylphloroglucinols substituted by a C10 unit, a prenyl group, and a methyl group. Formohyperins G–J (1–4) possess a 6/6/6-tricyclic structure, while formohyperins K (5) and L (6) have a unique 6/6/5/4-tetracyclic structure consisting of cyclohexadienone, dihydropyrane, cyclopentane, and cyclobutane rings. The absolute configurations of 1–6 were deduced by analysis of the ECD spectra. Formohyperins G–J (1–4) and L (6) were found to show potent inhibitory activities against IL-1β release from LPS-treated murine microglial cells with EC50 values of 5.0, 10.9, 6.3, 10.8, and 13.7 µM, respectively, without cytotoxicity. 6-O-Methylformohyperins G (1a) and I (3a) also exhibited the inhibitory activities with EC50 values of 4.7 and 2.7 µM, respectively, although they were cytotoxic against microglial cells.
{"title":"Formohyperins G–L, polycyclic prenylated benzoylphloroglucinols from the flowers of Hypericum formosanum","authors":"Rena Takizawa, Yusei Shimomoto, Daisuke Tsuji, Kiyoshi Imabayashi, Kohji Itoh, Reiko Akagi, Yoshiki Kashiwada, Naonobu Tanaka","doi":"10.1007/s11418-024-01839-6","DOIUrl":"10.1007/s11418-024-01839-6","url":null,"abstract":"<div><p>Phytochemical study on the flowers of <i>Hypericum formosanum</i> Maxim. (Hypericaceae) led to the isolation of formohyperins G–L (<b>1–6</b>), whose structures were assigned by detailed spectroscopic analysis. Formohyperins G–L (<b>1–6</b>) are new benzoylphloroglucinols substituted by a C<sub>10</sub> unit, a prenyl group, and a methyl group. Formohyperins G–J (<b>1–4</b>) possess a 6/6/6-tricyclic structure, while formohyperins K (<b>5</b>) and L (<b>6</b>) have a unique 6/6/5/4-tetracyclic structure consisting of cyclohexadienone, dihydropyrane, cyclopentane, and cyclobutane rings. The absolute configurations of <b>1–6</b> were deduced by analysis of the ECD spectra. Formohyperins G–J (<b>1–4</b>) and L (<b>6</b>) were found to show potent inhibitory activities against IL-1β release from LPS-treated murine microglial cells with EC<sub>50</sub> values of 5.0, 10.9, 6.3, 10.8, and 13.7 µM, respectively, without cytotoxicity. 6-<i>O</i>-Methylformohyperins G (<b>1a</b>) and I (<b>3a</b>) also exhibited the inhibitory activities with EC<sub>50</sub> values of 4.7 and 2.7 µM, respectively, although they were cytotoxic against microglial cells.</p><h3>Graphical abstract</h3><div><figure><div><div><picture><source><img></source></picture></div></div></figure></div></div>","PeriodicalId":654,"journal":{"name":"Journal of Natural Medicines","volume":"78 4","pages":"970 - 977"},"PeriodicalIF":2.5,"publicationDate":"2024-08-10","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"141911281","PeriodicalName":null,"FirstCategoryId":null,"ListUrlMain":null,"RegionNum":4,"RegionCategory":"医学","ArticlePicture":[],"TitleCN":null,"AbstractTextCN":null,"PMCID":"","EPubDate":null,"PubModel":null,"JCR":null,"JCRName":null,"Score":null,"Total":0}
Pub Date : 2024-08-05DOI: 10.1007/s11418-024-01835-w
Guantong Yu, Ruirui Wang, Xiaomei Liu, Yuhong Li, Lin Li, Xiaoming Wang, Yuhong Huang, Guixiang Pan
As a traditional Chinese medicine (TCM), Cortex Periplocae (CP) has a wide range of pharmacological effects, as well as toxic side effects. The main toxic components of it are cardiac glycosides, which tend to cause cardiotoxicity. Currently, it has also been reported in studies to cause hepatotoxicity, but it is not clear whether the hepatotoxicity is related to the toxicity caused by the reactive metabolites. This study aims to investigate the target components of CP that generate reactive metabolic toxicity. The fluorescent probe method was used to detect glutathione (GSH)-trapped reactive metabolites in a co-incubation system of CP extract with rat liver microsomes. Identification of GSH conjugates was performed by LC–MS/MS and that of the possible precursor components that produce reactive metabolites was conducted by UPLC–Q-TOF/MS. Cell viability assays were performed on HepG2 and L02 cells to determine the cytotoxicity of the target components. The findings of our study demonstrate that the extract derived from CP has the ability to generate metabolites that exhaust the intracellular GSH levels, resulting in the formation of GSH conjugates and subsequent cytotoxic effects. Through the utilization of the UPLC–Q-TOF/MS technique, we were able to accurately determine the molecular weight of the precursor compound in CP to be 355.1023. The primary evidence to determining the GSH conjugetes relies on the appearance of characteristic product ions resulting from central neutral loss (CNL) scanning of 129 Da and product scanning of m/z 660 in the positive MS/MS spectrum. Through analysis, it was ultimately ascertained that the presence of chlorogenic acid (CGA) and its isomers, namely neochlorogenic acid (NCGA) and cryptochlorogenic acid (CCGA), could lead to the production of GSH conjugates, resulting in cytotoxicity at elevated levels. Taking these findings into consideration, the underlying cause for the potential hepatotoxicity of CP was initially determined.
{"title":"Screening and identification of reactive metabolic compounds of Cortex Periplocae based on glutathione capture-mass spectrometry","authors":"Guantong Yu, Ruirui Wang, Xiaomei Liu, Yuhong Li, Lin Li, Xiaoming Wang, Yuhong Huang, Guixiang Pan","doi":"10.1007/s11418-024-01835-w","DOIUrl":"10.1007/s11418-024-01835-w","url":null,"abstract":"<div><p>As a traditional Chinese medicine (TCM), Cortex Periplocae (CP) has a wide range of pharmacological effects, as well as toxic side effects. The main toxic components of it are cardiac glycosides, which tend to cause cardiotoxicity. Currently, it has also been reported in studies to cause hepatotoxicity, but it is not clear whether the hepatotoxicity is related to the toxicity caused by the reactive metabolites. This study aims to investigate the target components of CP that generate reactive metabolic toxicity. The fluorescent probe method was used to detect glutathione (GSH)-trapped reactive metabolites in a co-incubation system of CP extract with rat liver microsomes. Identification of GSH conjugates was performed by LC–MS/MS and that of the possible precursor components that produce reactive metabolites was conducted by UPLC–Q-TOF/MS. Cell viability assays were performed on HepG2 and L02 cells to determine the cytotoxicity of the target components. The findings of our study demonstrate that the extract derived from CP has the ability to generate metabolites that exhaust the intracellular GSH levels, resulting in the formation of GSH conjugates and subsequent cytotoxic effects. Through the utilization of the UPLC–Q-TOF/MS technique, we were able to accurately determine the molecular weight of the precursor compound in CP to be 355.1023. The primary evidence to determining the GSH conjugetes relies on the appearance of characteristic product ions resulting from central neutral loss (CNL) scanning of 129 Da and product scanning of <i>m</i>/<i>z</i> 660 in the positive MS/MS spectrum. Through analysis, it was ultimately ascertained that the presence of chlorogenic acid (CGA) and its isomers, namely neochlorogenic acid (NCGA) and cryptochlorogenic acid (CCGA), could lead to the production of GSH conjugates, resulting in cytotoxicity at elevated levels. Taking these findings into consideration, the underlying cause for the potential hepatotoxicity of CP was initially determined.</p><h3>Graphical abstract</h3>\u0000<div><figure><div><div><picture><source><img></source></picture></div></div></figure></div></div>","PeriodicalId":654,"journal":{"name":"Journal of Natural Medicines","volume":"78 4","pages":"1044 - 1056"},"PeriodicalIF":2.5,"publicationDate":"2024-08-05","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"https://link.springer.com/content/pdf/10.1007/s11418-024-01835-w.pdf","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"141892538","PeriodicalName":null,"FirstCategoryId":null,"ListUrlMain":null,"RegionNum":4,"RegionCategory":"医学","ArticlePicture":[],"TitleCN":null,"AbstractTextCN":null,"PMCID":"OA","EPubDate":null,"PubModel":null,"JCR":null,"JCRName":null,"Score":null,"Total":0}
Pub Date : 2024-08-05DOI: 10.1007/s11418-024-01834-x
He Sun, Dandan Xiao, Xue Li, Tong Sun, Fanying Meng, Xinting Shao, Yuling Ding, Yong Li
Fungi, such as Trichophyton rubrum (T. rubrum) and Microsporum canis Bodin Anamorph (M. canis Bodin Anamorph) are the main pathogens of dermatophysis. According to ancient books records, Rumex japonicus Houtt. (RJH) has a miraculous effect on the treatment of dermatophysis. To reveal the anti-fungi (T. rubrum and M. canis Bodin Anamorph) components and its mechanism of the Rumex japonicus Houtt. The vinegar extraction and alcohol precipitation, HPLC and nuclear magnetic resonance spectroscopy (NMR) were employed for analyzing the chemical compositions of RJH; in vitro anti-fungal experiment was investigated including test the minimum inhibitory concentration (MIC) and the minimum fungicidal concentration (MFC), spore germination rate, nucleic acid, protein leakage rate, biofilm structure, and the mechanism of anti-fungal and anti-fungal biofilms in RJH. Seven anthraquinones and their glycoside compounds were obtained in this study respectively, such as chrysophanol, physcion, aloe-emodin, emodin, rhein, emodin-8-O-β-D-glucoside and chrysophanol-8-O-β-D-glucoside. In vitro anti-fungal experiment results showed that RJH extracts have good anti-fungal activity for dermatophytic fungi. Among them, the MIC of the rhein, emodin and aloe-emodin against T. rubrum are 1.9 µg/ml, 3.9 µg/ml and 15.6 µg/ml, respectively; the MIC of emodin and aloe-emodin against M. canis Bodin Anamorph are 7.8 µg/ml and 62.5 µg/ml, respectively. In addition, its active components can inhibit fungal spore germination and the formation of bud tube, change cell membrane permeability, prevent hyphal growth, destroy biofilm structure, and down-regulate the expression of agglutinin-like sequence family 1 of the adhesion phase of biofilm growth. The study shows that RJH play a fungicidal role.
{"title":"Study on the chemical composition and anti-fungi activities of anthraquinones and its glycosides from Rumex japonicus Houtt.","authors":"He Sun, Dandan Xiao, Xue Li, Tong Sun, Fanying Meng, Xinting Shao, Yuling Ding, Yong Li","doi":"10.1007/s11418-024-01834-x","DOIUrl":"10.1007/s11418-024-01834-x","url":null,"abstract":"<div><p>Fungi, such as <i>Trichophyton rubrum</i> (<i>T. rubrum</i>) and <i>Microsporum canis Bodin Anamorph</i> (<i>M. canis Bodin Anamorph</i>) are the main pathogens of dermatophysis. According to ancient books records, <i>Rumex japonicus</i> Houtt. (RJH) has a miraculous effect on the treatment of dermatophysis. To reveal the anti-fungi (<i>T. rubrum</i> and <i>M. canis Bodin Anamorph</i>) components and its mechanism of the <i>Rumex japonicus</i> Houtt. The vinegar extraction and alcohol precipitation, HPLC and nuclear magnetic resonance spectroscopy (NMR) were employed for analyzing the chemical compositions of RJH; in vitro anti-fungal experiment was investigated including test the minimum inhibitory concentration (MIC) and the minimum fungicidal concentration (MFC), spore germination rate, nucleic acid, protein leakage rate, biofilm structure, and the mechanism of anti-fungal and anti-fungal biofilms in RJH. Seven anthraquinones and their glycoside compounds were obtained in this study respectively, such as chrysophanol, physcion, aloe-emodin, emodin, rhein, emodin-8-O-<i>β</i>-D-glucoside and chrysophanol-8-O-<i>β</i>-D-glucoside. In <i>vitro</i> anti-fungal experiment results showed that RJH extracts have good anti-fungal activity for dermatophytic fungi. Among them, the MIC of the rhein, emodin and aloe-emodin against <i>T. rubrum</i> are 1.9 µg/ml, 3.9 µg/ml and 15.6 µg/ml, respectively; the MIC of emodin and aloe-emodin against <i>M. canis Bodin Anamorph</i> are 7.8 µg/ml and 62.5 µg/ml, respectively. In addition, its active components can inhibit fungal spore germination and the formation of bud tube, change cell membrane permeability, prevent hyphal growth, destroy biofilm structure, and down-regulate the expression of agglutinin-like sequence family 1 of the adhesion phase of biofilm growth. The study shows that RJH play a fungicidal role.</p><h3>Graphic abstract</h3>\u0000<div><figure><div><div><picture><source><img></source></picture></div></div></figure></div></div>","PeriodicalId":654,"journal":{"name":"Journal of Natural Medicines","volume":"78 4","pages":"929 - 951"},"PeriodicalIF":2.5,"publicationDate":"2024-08-05","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"141892539","PeriodicalName":null,"FirstCategoryId":null,"ListUrlMain":null,"RegionNum":4,"RegionCategory":"医学","ArticlePicture":[],"TitleCN":null,"AbstractTextCN":null,"PMCID":"","EPubDate":null,"PubModel":null,"JCR":null,"JCRName":null,"Score":null,"Total":0}
This study established an Orthogonal Partial Least Squares (OPLS) model combining 1H-NMR and GC-MS data to identify characteristic metabolites in complex extracts. Both in metabolomics studies, and natural product chemistry, the reliable identification of marker metabolites usually requires laborious isolation and purification steps, which remains a bottleneck in many studies. Both ginger (GR) and processed ginger (PGR) are listed in the Japanese pharmacopeia. The plant of origin, the rhizome of Zingiber officinale Roscoe, is differently processed for these crude drugs. Notably, the quality of crude drugs is affected by genetic and environmental factors, making it difficult to maintain a certain quality standard. Therefore, characteristic markers for the quality control of GR and PGR are required. Metabolomic analysis using 1H-NMR was able to discriminate between GR and PGR, but there were unidentified signals that were difficult to distinguish based on NMR data alone. Therefore, we combined 1H-NMR and GC-MS analytical data to identify them by OPLS. As a result, αr-curcumene was found to be a useful marker for these identifications. This new approach enabled rapid identification of characteristic marker compounds and reduced the labor involved in the isolation process.
{"title":"Development of a determination method for quality control markers utilizing metabolic profiling and its application on processed Zingiber officinale Roscoe rhizome","authors":"Tomohisa Kanai, Tatsuya Shirahata, Shunsuke Nakamori, Yota Koizumi, Eiichi Kodaira, Noriko Sato, Hiroyuki Fuchino, Noriaki Kawano, Nobuo Kawahara, Takayuki Hoshino, Kayo Yoshimatsu, Yoshinori Kobayashi","doi":"10.1007/s11418-024-01837-8","DOIUrl":"10.1007/s11418-024-01837-8","url":null,"abstract":"<div><p>This study established an Orthogonal Partial Least Squares (OPLS) model combining <sup>1</sup>H-NMR and GC-MS data to identify characteristic metabolites in complex extracts. Both in metabolomics studies, and natural product chemistry, the reliable identification of marker metabolites usually requires laborious isolation and purification steps, which remains a bottleneck in many studies. Both ginger (GR) and processed ginger (PGR) are listed in the Japanese pharmacopeia. The plant of origin, the rhizome of <i>Zingiber officinale</i> Roscoe, is differently processed for these crude drugs. Notably, the quality of crude drugs is affected by genetic and environmental factors, making it difficult to maintain a certain quality standard. Therefore, characteristic markers for the quality control of GR and PGR are required. Metabolomic analysis using <sup>1</sup>H-NMR was able to discriminate between GR and PGR, but there were unidentified signals that were difficult to distinguish based on NMR data alone. Therefore, we combined <sup>1</sup>H-NMR and GC-MS analytical data to identify them by OPLS. As a result, α<i>r</i>-curcumene was found to be a useful marker for these identifications. This new approach enabled rapid identification of characteristic marker compounds and reduced the labor involved in the isolation process.</p><h3>Graphical abstract</h3>\u0000<div><figure><div><div><picture><source><img></source></picture></div></div></figure></div></div>","PeriodicalId":654,"journal":{"name":"Journal of Natural Medicines","volume":"78 4","pages":"952 - 969"},"PeriodicalIF":2.5,"publicationDate":"2024-08-03","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"https://link.springer.com/content/pdf/10.1007/s11418-024-01837-8.pdf","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"141886801","PeriodicalName":null,"FirstCategoryId":null,"ListUrlMain":null,"RegionNum":4,"RegionCategory":"医学","ArticlePicture":[],"TitleCN":null,"AbstractTextCN":null,"PMCID":"OA","EPubDate":null,"PubModel":null,"JCR":null,"JCRName":null,"Score":null,"Total":0}
Pub Date : 2024-08-02DOI: 10.1007/s11418-024-01833-y
Yasumasa Hara
The genus Nocardia are gram-positive bacteria, many of which possess pathogenicity and infect human lungs, skin, brain, and other organs. Since research on the genus Nocardia has not progressed as rapidly as that on the genus Streptomyces, the genus Nocardia is considered a useful undeveloped resource for exploring natural products. On the other hand, when the genus Nocardia infects the human body, the strains are attacked by immune cells such as macrophages. Therefore, we suggested a new method for screening natural products by culturing the genus Nocardia in the presence of animal cells. In this review, we describe our recent results in searching for natural products from the genus Nocardia.
{"title":"Search for natural products from actinomycetes of the genus Nocardia","authors":"Yasumasa Hara","doi":"10.1007/s11418-024-01833-y","DOIUrl":"10.1007/s11418-024-01833-y","url":null,"abstract":"<div><p>The genus <i>Nocardia</i> are gram-positive bacteria, many of which possess pathogenicity and infect human lungs, skin, brain, and other organs. Since research on the genus <i>Nocardia</i> has not progressed as rapidly as that on the genus <i>Streptomyces</i>, the genus <i>Nocardia</i> is considered a useful undeveloped resource for exploring natural products. On the other hand, when the genus <i>Nocardia</i> infects the human body, the strains are attacked by immune cells such as macrophages. Therefore, we suggested a new method for screening natural products by culturing the genus <i>Nocardia</i> in the presence of animal cells. In this review, we describe our recent results in searching for natural products from the genus <i>Nocardia</i>.</p><h3>Graphical abstract</h3>\u0000<div><figure><div><div><picture><img></picture></div></div></figure></div></div>","PeriodicalId":654,"journal":{"name":"Journal of Natural Medicines","volume":"78 4","pages":"828 - 837"},"PeriodicalIF":2.5,"publicationDate":"2024-08-02","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"https://www.ncbi.nlm.nih.gov/pmc/articles/PMC11364655/pdf/","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"141873886","PeriodicalName":null,"FirstCategoryId":null,"ListUrlMain":null,"RegionNum":4,"RegionCategory":"医学","ArticlePicture":[],"TitleCN":null,"AbstractTextCN":null,"PMCID":"OA","EPubDate":null,"PubModel":null,"JCR":null,"JCRName":null,"Score":null,"Total":0}
Inflammation-induced intestinal epithelial barrier (IEB) dysfunction is one of the important reasons for the occurrence and development of intestinal inflammatory-related diseases, including ulcerative colitis (UC), Crohn’s disease and necrotizing enterocolitis (NEC). Dragon’s blood (DB) is a traditional Chinese medicine and has been clinically used to treat UC. However, the protective mechanism of DB on intestinal inflammatory-related diseases has still not been elucidated. The present study aimed to explore the protection mechanism of DB on IEB dysfunction in rat ileum and human colorectal adenocarcinoma cells (Caco-2)/human umbilical vein endothelial cells (HUVECs) coculture system induced by lipopolysaccharide (LPS). DB could ameliorate rat ileum mucosa morphological injury, reduce the accumulation of lipid-peroxidation products and increase the expression of junction proteins. DB also alleviated LPS-induced Caco-2 cells barrier integrity destruction in Caco-2/ HUVECs coculture system, leading to increased trans-endothelial electrical resistance (TEER), reduced cell permeability, and upregulation of expressions of F-actin and junction proteins. DB contributed to the assembly of actin cytoskeleton by upregulating the FAK-DOCK180-Rac1-WAVE2-Arp3 pathway and contributed to the formation of intercellular junctions by downregulating TLR4-MyD88-NF-κB pathway, thus reversing LPS-induced IEB dysfunction. These novel findings illustrated the potential protective mechanism of DB on intestinal inflammatory-related diseases and might be useful for further clinical application of DB.
{"title":"Dragon’s blood attenuates LPS-induced intestinal epithelial barrier dysfunction via upregulation of FAK-DOCK180-Rac1-WAVE2-Arp3 and downregulation of TLR4/NF-κB signaling pathways","authors":"Huayan Liu, Ranran Yan, Yongzhi Li, Jiaping Wang, Yulin Deng, Yujuan Li","doi":"10.1007/s11418-024-01824-z","DOIUrl":"10.1007/s11418-024-01824-z","url":null,"abstract":"<div><p>Inflammation-induced intestinal epithelial barrier (IEB) dysfunction is one of the important reasons for the occurrence and development of intestinal inflammatory-related diseases, including ulcerative colitis (UC), Crohn’s disease and necrotizing enterocolitis (NEC). Dragon’s blood (DB) is a traditional Chinese medicine and has been clinically used to treat UC. However, the protective mechanism of DB on intestinal inflammatory-related diseases has still not been elucidated. The present study aimed to explore the protection mechanism of DB on IEB dysfunction in rat ileum and human colorectal adenocarcinoma cells (Caco-2)/human umbilical vein endothelial cells (HUVECs) coculture system induced by lipopolysaccharide (LPS). DB could ameliorate rat ileum mucosa morphological injury, reduce the accumulation of lipid-peroxidation products and increase the expression of junction proteins. DB also alleviated LPS-induced Caco-2 cells barrier integrity destruction in Caco-2/ HUVECs coculture system, leading to increased trans-endothelial electrical resistance (TEER), reduced cell permeability, and upregulation of expressions of F-actin and junction proteins. DB contributed to the assembly of actin cytoskeleton by upregulating the FAK-DOCK180-Rac1-WAVE2-Arp3 pathway and contributed to the formation of intercellular junctions by downregulating TLR4-MyD88-NF-κB pathway, thus reversing LPS-induced IEB dysfunction. These novel findings illustrated the potential protective mechanism of DB on intestinal inflammatory-related diseases and might be useful for further clinical application of DB.</p><h3>Graphical abstract</h3>\u0000<div><figure><div><div><picture><source><img></source></picture></div></div></figure></div></div>","PeriodicalId":654,"journal":{"name":"Journal of Natural Medicines","volume":"78 4","pages":"1013 - 1028"},"PeriodicalIF":2.5,"publicationDate":"2024-07-17","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"https://link.springer.com/content/pdf/10.1007/s11418-024-01824-z.pdf","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"141625556","PeriodicalName":null,"FirstCategoryId":null,"ListUrlMain":null,"RegionNum":4,"RegionCategory":"医学","ArticlePicture":[],"TitleCN":null,"AbstractTextCN":null,"PMCID":"OA","EPubDate":null,"PubModel":null,"JCR":null,"JCRName":null,"Score":null,"Total":0}
Pub Date : 2024-07-17DOI: 10.1007/s11418-024-01830-1
Yukiko Matsuo, Yoshihiro Mimaki
Chemical investigations of higher plants, with particular attention paid to their steroidal glycosides, present a promising approach for generating anti-cancer agents from natural products. We conducted a systematic phytochemical investigation of nine higher plants—whole plants and rhizomes of Convallaria majalis, whole plants of Agave utahensis, roots of Adonis amurensis, seeds of Adonis aestivalis, bulbs of Bessera elegans, bulbs of Fritillaria meleagris, seeds of Digitalis purpurea, underground parts of Yucca glauca, and bulbs of Lilium pumilum—which led to the discovery of novel steroidal glycosides. The structures of these new constituents were determined based on spectroscopic data and chemical transformations. The identification of the monosaccharides including their absolute configurations was carried out by direct HPLC analysis of their hydrolysates using an optical rotation detector. Cytotoxicity of the isolated steroidal glycosides was evaluated against various tumor cells (A549, ACHN, HepG-2, HL-60, HSC-2, HSC-3, HSC-4, HSG, and SBC-3) and normal cells (Fa2 N-4, HK-2, and TIG-3 cells). Certain steroidal glycosides exhibit selective cytotoxicity and synergistic effects, making them potential lead compounds for use as anti-cancer agents. We document the isolation of 139 steroidal glycosides from higher plants and assessment their cytotoxic activities.
{"title":"Search for new steroidal glycosides with anti-cancer potential from natural resources","authors":"Yukiko Matsuo, Yoshihiro Mimaki","doi":"10.1007/s11418-024-01830-1","DOIUrl":"10.1007/s11418-024-01830-1","url":null,"abstract":"<div><p>Chemical investigations of higher plants, with particular attention paid to their steroidal glycosides, present a promising approach for generating anti-cancer agents from natural products. We conducted a systematic phytochemical investigation of nine higher plants—whole plants and rhizomes of <i>Convallaria majalis</i>, whole plants of <i>Agave utahensis</i>, roots of <i>Adonis amurensis</i>, seeds of <i>Adonis aestivalis</i>, bulbs of <i>Bessera elegans</i>, bulbs of <i>Fritillaria meleagris</i>, seeds of <i>Digitalis purpurea</i>, underground parts of <i>Yucca glauca</i>, and bulbs of <i>Lilium pumilum—</i>which led to the discovery of novel steroidal glycosides. The structures of these new constituents were determined based on spectroscopic data and chemical transformations. The identification of the monosaccharides including their absolute configurations was carried out by direct HPLC analysis of their hydrolysates using an optical rotation detector. Cytotoxicity of the isolated steroidal glycosides was evaluated against various tumor cells (A549, ACHN, HepG-2, HL-60, HSC-2, HSC-3, HSC-4, HSG, and SBC-3) and normal cells (Fa2 N-4, HK-2, and TIG-3 cells). Certain steroidal glycosides exhibit selective cytotoxicity and synergistic effects, making them potential lead compounds for use as anti-cancer agents. We document the isolation of 139 steroidal glycosides from higher plants and assessment their cytotoxic activities.</p><h3>Graphical abstract</h3><div><figure><div><div><picture><source><img></source></picture></div></div></figure></div></div>","PeriodicalId":654,"journal":{"name":"Journal of Natural Medicines","volume":"78 4","pages":"807 - 827"},"PeriodicalIF":2.5,"publicationDate":"2024-07-17","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"https://www.ncbi.nlm.nih.gov/pmc/articles/PMC11364615/pdf/","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"141625557","PeriodicalName":null,"FirstCategoryId":null,"ListUrlMain":null,"RegionNum":4,"RegionCategory":"医学","ArticlePicture":[],"TitleCN":null,"AbstractTextCN":null,"PMCID":"OA","EPubDate":null,"PubModel":null,"JCR":null,"JCRName":null,"Score":null,"Total":0}
{"title":"Correction: Visualizing the spatial distribution of ustalic acid in the fruiting body of Tricholoma kakishimeji","authors":"Tetsuro Ito, Shu Taira, Wataru Aoki, Hiroyuki Nagai, Masashi Fukaya, Kaori Ryu, Akiyoshi Yamada","doi":"10.1007/s11418-024-01828-9","DOIUrl":"10.1007/s11418-024-01828-9","url":null,"abstract":"","PeriodicalId":654,"journal":{"name":"Journal of Natural Medicines","volume":"78 4","pages":"844 - 844"},"PeriodicalIF":2.5,"publicationDate":"2024-07-08","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"141557771","PeriodicalName":null,"FirstCategoryId":null,"ListUrlMain":null,"RegionNum":4,"RegionCategory":"医学","ArticlePicture":[],"TitleCN":null,"AbstractTextCN":null,"PMCID":"","EPubDate":null,"PubModel":null,"JCR":null,"JCRName":null,"Score":null,"Total":0}
A phytochemical investigation of Kaempferia champasakensis rhizomes led to the isolation of five new pimarane diterpenes, kaempferiols E–I (1–5). The structures of 1–5 were elucidated by extensive spectroscopic techniques, including HR-ESI–MS, UV, IR, and 1D and 2D NMR. The absolute configurations of 1–3 were determined by the modified Mosher method, and those of 4 and 5 were established by ECD calculations. Further cytotoxic assay for all isolated compounds against three human cancer cell lines, lung cancer (A549), cervical cancer (HeLa), and breast cancer (MCF-7) indicated that 5 showed moderate cytotoxic activities against the three tested cell lines, with IC50 values of 44.78, 25.97, and 41.39 Mμ for A549, HeLa, and MCF-7 cell lines, respectively.
{"title":"Five pimarane diterpenoids from Kaempferia champasakensis and their cytotoxic activities","authors":"Kiep Minh Do, Shotaro Hoshino, Takeshi Kodama, Hien Minh Nguyen, Naotaka Ikumi, Hiroyasu Onaka, Hiroyuki Morita","doi":"10.1007/s11418-024-01829-8","DOIUrl":"10.1007/s11418-024-01829-8","url":null,"abstract":"<div><p>A phytochemical investigation of <i>Kaempferia champasakensis</i> rhizomes led to the isolation of five new pimarane diterpenes, kaempferiols E–I (<b>1–5</b>). The structures of <b>1–5</b> were elucidated by extensive spectroscopic techniques, including HR-ESI–MS, UV, IR, and 1D and 2D NMR. The absolute configurations of <b>1–3</b> were determined by the modified Mosher method, and those of <b>4</b> and <b>5</b> were established by ECD calculations. Further cytotoxic assay for all isolated compounds against three human cancer cell lines, lung cancer (A549), cervical cancer (HeLa), and breast cancer (MCF-7) indicated that <b>5</b> showed moderate cytotoxic activities against the three tested cell lines, with IC<sub>50</sub> values of 44.78, 25.97, and 41.39 Mμ for A549, HeLa, and MCF-7 cell lines, respectively.</p><h3>Graphical abstract</h3>\u0000<div><figure><div><div><picture><source><img></source></picture></div></div></figure></div></div>","PeriodicalId":654,"journal":{"name":"Journal of Natural Medicines","volume":"78 4","pages":"908 - 918"},"PeriodicalIF":2.5,"publicationDate":"2024-07-02","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"141490436","PeriodicalName":null,"FirstCategoryId":null,"ListUrlMain":null,"RegionNum":4,"RegionCategory":"医学","ArticlePicture":[],"TitleCN":null,"AbstractTextCN":null,"PMCID":"","EPubDate":null,"PubModel":null,"JCR":null,"JCRName":null,"Score":null,"Total":0}
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