Pub Date : 2024-12-09DOI: 10.1016/j.phytochem.2024.114357
Hong-Ping Long , Xi Zhou , Si-Qian Zhou , Lan-Qing Li , Ai-Lin Liang , Wen-Yu Lu , Wen-Xuan Wang , Shao Liu , Jing Li , Ji-Kai Liu
Five brasilane-type sesquiterpenoids, including four previously undescribed compounds named xylaribrasilaids A–D, along with a known analogue, were isolated from the ethyl acetate extracts of solid fermentation from Xylaria nigripes. X. nigripes, a traditional Chinese medicinal fungus utilized for treating various ailments such as insomnia, trauma, and depression, has garnered attention due to its pharmacological potential. Their structures and absolute configurations were elucidated through comprehensive spectroscopic analysis, including NMR, HRESIMS, and experimental ECD data. In vitro bioassays were conducted to assess the neuroprotective activities of these compounds against glutamate-induced damage in PC12 cells. Remarkably, all isolated compounds demonstrated significant enhancements in cell viability while concurrently inhibiting apoptosis. Moreover, they effectively attenuated oxidative stress markers, as evidenced by increased activities of superoxide dismutase and glutathione. Furthermore, these compounds displayed the capacity to mitigate intracellular reactive oxygen species accumulation, highlighting their potential in combating oxidative stress-related neurodegenerative disorders.
从黑木霉固体发酵的乙酸乙酯萃取物中分离得到5个巴西烷型倍半萜类化合物，包括4个先前未被描述的化合物xylaribrasilaids a - d，以及一个已知的类似物。黑木耳是一种用于治疗失眠、创伤、抑郁等各种疾病的传统中药真菌，因其药理潜力而受到关注。通过NMR、hremsims和实验ECD数据等综合光谱分析，阐明了它们的结构和绝对构型。体外生物测定评估了这些化合物对谷氨酸诱导的PC12细胞损伤的神经保护活性。值得注意的是，所有分离的化合物都能显著增强细胞活力，同时抑制细胞凋亡。此外，它们有效地减弱了氧化应激标志物，如超氧化物歧化酶和谷胱甘肽活性的增加。此外，这些化合物显示出减轻细胞内活性氧积累的能力，突出了它们在对抗氧化应激相关神经退行性疾病方面的潜力。
{"title":"Five brasilane-type sesquiterpenoids with neuroprotective activities from Xylaria nigripes","authors":"Hong-Ping Long , Xi Zhou , Si-Qian Zhou , Lan-Qing Li , Ai-Lin Liang , Wen-Yu Lu , Wen-Xuan Wang , Shao Liu , Jing Li , Ji-Kai Liu","doi":"10.1016/j.phytochem.2024.114357","DOIUrl":"10.1016/j.phytochem.2024.114357","url":null,"abstract":"<div><div>Five brasilane-type sesquiterpenoids, including four previously undescribed compounds named xylaribrasilaids A–D, along with a known analogue, were isolated from the ethyl acetate extracts of solid fermentation from <em>Xylaria nigripes</em>. <em>X</em>. <em>nigripes</em>, a traditional Chinese medicinal fungus utilized for treating various ailments such as insomnia, trauma, and depression, has garnered attention due to its pharmacological potential. Their structures and absolute configurations were elucidated through comprehensive spectroscopic analysis, including NMR, HRESIMS, and experimental ECD data. <em>In vitro</em> bioassays were conducted to assess the neuroprotective activities of these compounds against glutamate-induced damage in PC12 cells. Remarkably, all isolated compounds demonstrated significant enhancements in cell viability while concurrently inhibiting apoptosis. Moreover, they effectively attenuated oxidative stress markers, as evidenced by increased activities of superoxide dismutase and glutathione. Furthermore, these compounds displayed the capacity to mitigate intracellular reactive oxygen species accumulation, highlighting their potential in combating oxidative stress-related neurodegenerative disorders.</div></div>","PeriodicalId":20170,"journal":{"name":"Phytochemistry","volume":"231 ","pages":"Article 114357"},"PeriodicalIF":3.2,"publicationDate":"2024-12-09","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"142814114","PeriodicalName":null,"FirstCategoryId":null,"ListUrlMain":null,"RegionNum":2,"RegionCategory":"生物学","ArticlePicture":[],"TitleCN":null,"AbstractTextCN":null,"PMCID":"","EPubDate":null,"PubModel":null,"JCR":null,"JCRName":null,"Score":null,"Total":0}
Pub Date : 2024-12-09DOI: 10.1016/j.phytochem.2024.114352
Min Tan , Xiao-Cong Liu , Dan Liu, Xuan-Qin Chen, Rong-Tao Li, Zhi-Jun Zhang
An undescribed coumarin–limonene hybrid (morusalin A, 1), an unreported steppogenin–limonene hybrid (morusalin B, 2), and three undescribed isoprenylated flavonoids (morusalins C–E, 3–5), along with forty-one known ones (6–46), were isolated from the dried roots bark of Morus alba. Their structures with absolute configurations were elucidated by detailed interpretation of NMR spectroscopy, mass spectrometry, single-crystal X-ray diffraction, and ECD calculations. In addition, all these isolated compounds were assayed for their inhibitory activity against lipopolysaccharide (LPS)-induced nitric oxide (NO) production in murine macro-phage RAW 264.7 cells and for their cytotoxic activities against human colon cancer (HCT 8) and hepatoma (HepG 2) cells. Moreover, a biosynthetic pathway for the formation of compounds 1–6 is also proposed.
从桑树的干根树皮中分离出一种未被描述的香豆素-柠檬烯杂交体（morusalin A, 1），一种未被报道的steppogenin-柠檬烯杂交体（morusalin B, 2）和三种未被描述的异戊烯化黄酮类化合物（morusalins C-E, 3-5），以及41种已知的黄酮类化合物（6-46）。通过核磁共振谱、质谱、单晶x射线衍射和ECD计算，对它们的绝对构型结构进行了详细的解释。此外，我们还检测了所有分离得到的化合物对脂多糖（LPS）诱导的小鼠巨噬细胞RAW 264.7细胞一氧化氮（NO）产生的抑制活性以及对人结肠癌（HCT 8）和肝癌（HepG 2）细胞的细胞毒活性。此外，还提出了化合物1-6形成的生物合成途径。
{"title":"Isolation, characterization and biological activities of phenolics from the roots bark of Morus alba","authors":"Min Tan , Xiao-Cong Liu , Dan Liu, Xuan-Qin Chen, Rong-Tao Li, Zhi-Jun Zhang","doi":"10.1016/j.phytochem.2024.114352","DOIUrl":"10.1016/j.phytochem.2024.114352","url":null,"abstract":"<div><div>An undescribed coumarin–limonene hybrid (morusalin A, <strong>1</strong>), an unreported steppogenin–limonene hybrid (morusalin B, <strong>2</strong>), and three undescribed isoprenylated flavonoids (morusalins C–E, <strong>3</strong>–<strong>5</strong>), along with forty-one known ones (<strong>6</strong>–<strong>46</strong>), were isolated from the dried roots bark of <em>Morus alba</em>. Their structures with absolute configurations were elucidated by detailed interpretation of NMR spectroscopy, mass spectrometry, single-crystal X-ray diffraction, and ECD calculations. In addition, all these isolated compounds were assayed for their inhibitory activity against lipopolysaccharide (LPS)-induced nitric oxide (NO) production in murine macro-phage RAW 264.7 cells and for their cytotoxic activities against human colon cancer (HCT 8) and hepatoma (HepG 2) cells. Moreover, a biosynthetic pathway for the formation of compounds <strong>1</strong>–<strong>6</strong> is also proposed.</div></div>","PeriodicalId":20170,"journal":{"name":"Phytochemistry","volume":"231 ","pages":"Article 114352"},"PeriodicalIF":3.2,"publicationDate":"2024-12-09","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"142814116","PeriodicalName":null,"FirstCategoryId":null,"ListUrlMain":null,"RegionNum":2,"RegionCategory":"生物学","ArticlePicture":[],"TitleCN":null,"AbstractTextCN":null,"PMCID":"","EPubDate":null,"PubModel":null,"JCR":null,"JCRName":null,"Score":null,"Total":0}
Pub Date : 2024-12-09DOI: 10.1016/j.phytochem.2024.114355
Zhong-Shun Zhou , Wen-Biao Zu , Yan-Yan Zhu , Mei-Zhen Wei , Yue-Ming Jiang , Zhao-Jie Wang , Yun-Li Zhao , Xiao-Dong Luo
Ten previously undescribed phyto-oxylipins siegesoxylipin A‒J (1–10), along with four known analogs (11–14), were isolated from the aerial parts of Sigesbeckia orientalis. The elucidation of their structures was accomplished through spectroscopic analyses, base-catalyzed hydrolysis and X-ray diffraction. Moreover, unmethylesterified 4-methylpentanoic acid siegesoxylipins 1, 2, and 4–7 exhibited potent inhibitory bioactivity against methicillin-resistant Staphylococcus aureus (MRSA) and vancomycin-resistant Enterococci (VRE) strains with MIC values of 8 μg/mL, in which siegesoxylipin A (1) inhibited bacteria by inducing membrane damage. Siegesoxylipins represent an original class of anti-MRSA and anti-VRE agents with 4-methylpentanoates incorporating fatty acid moieties. This discovery holds promise for the development of new therapeutic strategies to combat antibiotic-resistant infections.
{"title":"Siegesoxylipin A‒J, previously undescribed phyto-oxylipins inhibition of methicillin-resistant Staphylococcus aureus and vancomycin-resistant Enterococci from Sigesbeckia orientalis","authors":"Zhong-Shun Zhou , Wen-Biao Zu , Yan-Yan Zhu , Mei-Zhen Wei , Yue-Ming Jiang , Zhao-Jie Wang , Yun-Li Zhao , Xiao-Dong Luo","doi":"10.1016/j.phytochem.2024.114355","DOIUrl":"10.1016/j.phytochem.2024.114355","url":null,"abstract":"<div><div>Ten previously undescribed phyto-oxylipins siegesoxylipin A‒J (<strong>1</strong>–<strong>10</strong>), along with four known analogs (<strong>11</strong>–<strong>14</strong>), were isolated from the aerial parts of <em>Sigesbeckia orientalis</em>. The elucidation of their structures was accomplished through spectroscopic analyses, base-catalyzed hydrolysis and X-ray diffraction. Moreover, unmethylesterified 4-methylpentanoic acid siegesoxylipins <strong>1</strong>, <strong>2</strong>, and <strong>4</strong>–<strong>7</strong> exhibited potent inhibitory bioactivity against methicillin-resistant <em>Staphylococcus aureus</em> (MRSA) and vancomycin-resistant <em>Enterococci</em> (VRE) strains with MIC values of 8 μg/mL, in which siegesoxylipin A (<strong>1</strong>) inhibited bacteria by inducing membrane damage. Siegesoxylipins represent an original class of anti-MRSA and anti-VRE agents with 4-methylpentanoates incorporating fatty acid moieties. This discovery holds promise for the development of new therapeutic strategies to combat antibiotic-resistant infections.</div></div>","PeriodicalId":20170,"journal":{"name":"Phytochemistry","volume":"231 ","pages":"Article 114355"},"PeriodicalIF":3.2,"publicationDate":"2024-12-09","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"142814117","PeriodicalName":null,"FirstCategoryId":null,"ListUrlMain":null,"RegionNum":2,"RegionCategory":"生物学","ArticlePicture":[],"TitleCN":null,"AbstractTextCN":null,"PMCID":"","EPubDate":null,"PubModel":null,"JCR":null,"JCRName":null,"Score":null,"Total":0}
Pub Date : 2024-11-28DOI: 10.1016/j.phytochem.2024.114342
Ying Gao , Juan Chen , Junjun Liu , Zijian Huang , Xiaogang Peng , Wanpeng Li , Chunlun Qin , Hanli Ruan
In this study, incartrilactones A (1) and B (2), two previously undescribed schinortriterpenoids (SNTs) possessing an unprecedented 5/5/6/5/7/5-fused hexacyclic skeleton, together with one previously undescribed (3) and one known (4) analogues, were isolated from the stems of Schisandra incarnata Stapf. Their structures with absolute configurations were determined by comprehensive spectroscopic analysis, X-ray crystallography and electronic circular dichroism calculation. Compounds 1 and 2 represent the first class of 14,15-seco-15,17-cyclolancifoartane-type SNTs containing the unusual linkage of ‒C14‒C16‒C13‒C17‒C15. The hypothetical biogenetic pathway of compounds 1 and 2 was postulated. Compounds 1 and 2 exhibited potent α-glucosidase inhibitory activity with IC50 values of 133.1 and 165.3 μM, representing that they were more active than the positive control, acarbose (IC50 = 232.8 μM). Compound 4 showed moderate in vitro immunosuppressive effect against ConA-induced T cell and LPS-induced B cell proliferation, with IC50 values of 35.3 ± 0.9 μM and 24.9 ± 0.6 μM, respectively. The cytotoxicity of compounds 1−4 against three human cancer cell lines was also tested, with no obvious cytotoxicity being observed.
{"title":"Incartrilactones A and B: Two schinortriterpenoids with a 14,15-seco-15,17-cyclolancifoartane skeleton from Schisandra incarnata","authors":"Ying Gao , Juan Chen , Junjun Liu , Zijian Huang , Xiaogang Peng , Wanpeng Li , Chunlun Qin , Hanli Ruan","doi":"10.1016/j.phytochem.2024.114342","DOIUrl":"10.1016/j.phytochem.2024.114342","url":null,"abstract":"<div><div>In this study, incartrilactones A (<strong>1</strong>) and B (<strong>2</strong>), two previously undescribed schinortriterpenoids (SNTs) possessing an unprecedented 5/5/6/5/7/5-fused hexacyclic skeleton, together with one previously undescribed (<strong>3</strong>) and one known (<strong>4</strong>) analogues, were isolated from the stems of <em>Schisandra incarnata</em> Stapf. Their structures with absolute configurations were determined by comprehensive spectroscopic analysis, X-ray crystallography and electronic circular dichroism calculation. Compounds <strong>1</strong> and <strong>2</strong> represent the first class of 14,15-seco-15,17-cyclolancifoartane-type SNTs containing the unusual linkage of ‒C14‒C16‒C13‒C17‒C15. The hypothetical biogenetic pathway of compounds <strong>1</strong> and <strong>2</strong> was postulated. Compounds <strong>1</strong> and <strong>2</strong> exhibited potent <em>α</em>-glucosidase inhibitory activity with IC<sub>50</sub> values of 133.1 and 165.3 μM, representing that they were more active than the positive control, acarbose (IC<sub>50</sub> = 232.8 μM). Compound <strong>4</strong> showed moderate <em>in vitro</em> immunosuppressive effect against ConA-induced T cell and LPS-induced B cell proliferation, with IC<sub>50</sub> values of 35.3 ± 0.9 μM and 24.9 ± 0.6 μM, respectively. The cytotoxicity of compounds <strong>1</strong>−<strong>4</strong> against three human cancer cell lines was also tested, with no obvious cytotoxicity being observed.</div></div>","PeriodicalId":20170,"journal":{"name":"Phytochemistry","volume":"231 ","pages":"Article 114342"},"PeriodicalIF":3.2,"publicationDate":"2024-11-28","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"142755515","PeriodicalName":null,"FirstCategoryId":null,"ListUrlMain":null,"RegionNum":2,"RegionCategory":"生物学","ArticlePicture":[],"TitleCN":null,"AbstractTextCN":null,"PMCID":"","EPubDate":null,"PubModel":null,"JCR":null,"JCRName":null,"Score":null,"Total":0}
Pub Date : 2024-11-28DOI: 10.1016/j.phytochem.2024.114344
Jialin Li , Hao Jia , Chen Chen , Shu An , Jianchen Yu , Jie Yuan , Yuhua Long , Mengfeng Li
Under the guidance of LC‒MS/MS-based molecular networking, three previously undescribed berkeleyacetal type meroterpenoids, amestolknoids A-C (1–3), together with ten known analogues (4–13) were isolated and identified from the mangrove endophytic fungus Talaromyces amestolkiae SCNU–F0041. Amestolknoids A (1) and B (2) are unprecedentedly congested 6/7/6/5/5/5/5 heptacyclic scaffolds characterized by two chiral spiroketal centers. Amestolknoids A (1) and C (3) represent the first examples of chlorinated berkeleyacetal type meroterpenoids. Their structures were established by extensive spectroscopic analyses and single crystal X-ray diffraction. Bioassays revealed that amestolknoid C (3) exhibited excellent antiviral activity against SARS-CoV-2 with an EC50 value of 2.50 μM and strong inhibitory effects on nitric oxide production in lipopolysaccharide-activated RAW 264.7 cells with an IC50 value of 4.10 μM. Compounds 2, 4, 6, 9 and 11 showed moderate to good anti-inflammatory activities with IC50 values of 41.78, 3.91, 43.52, 20.79, and 33.26 μM, respectively.
{"title":"Congested heptacyclic meroterpenoids with anti-SARS-CoV-2 and anti-inflammatory activities from mangrove endophytic fungus Talaromyces amestolkiae SCNU–F0041","authors":"Jialin Li , Hao Jia , Chen Chen , Shu An , Jianchen Yu , Jie Yuan , Yuhua Long , Mengfeng Li","doi":"10.1016/j.phytochem.2024.114344","DOIUrl":"10.1016/j.phytochem.2024.114344","url":null,"abstract":"<div><div>Under the guidance of LC‒MS/MS-based molecular networking, three previously undescribed berkeleyacetal type meroterpenoids, amestolknoids A-C (<strong>1</strong>–<strong>3</strong>), together with ten known analogues (<strong>4</strong>–<strong>13</strong>) were isolated and identified from the mangrove endophytic fungus <em>Talaromyces amestolkiae</em> SCNU–F0041. Amestolknoids A (<strong>1</strong>) and B (<strong>2</strong>) are unprecedentedly congested 6/7/6/5/5/5/5 heptacyclic scaffolds characterized by two chiral spiroketal centers. Amestolknoids A (<strong>1</strong>) and C (<strong>3</strong>) represent the first examples of chlorinated berkeleyacetal type meroterpenoids. Their structures were established by extensive spectroscopic analyses and single crystal X-ray diffraction. Bioassays revealed that amestolknoid C (<strong>3</strong>) exhibited excellent antiviral activity against SARS-CoV-2 with an EC<sub>50</sub> value of 2.50 μM and strong inhibitory effects on nitric oxide production in lipopolysaccharide-activated RAW 264.7 cells with an IC<sub>50</sub> value of 4.10 μM. Compounds <strong>2</strong>, <strong>4</strong>, <strong>6</strong>, <strong>9</strong> and <strong>11</strong> showed moderate to good anti-inflammatory activities with IC<sub>50</sub> values of 41.78, 3.91, 43.52, 20.79, and 33.26 μM, respectively.</div></div>","PeriodicalId":20170,"journal":{"name":"Phytochemistry","volume":"231 ","pages":"Article 114344"},"PeriodicalIF":3.2,"publicationDate":"2024-11-28","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"142755511","PeriodicalName":null,"FirstCategoryId":null,"ListUrlMain":null,"RegionNum":2,"RegionCategory":"生物学","ArticlePicture":[],"TitleCN":null,"AbstractTextCN":null,"PMCID":"","EPubDate":null,"PubModel":null,"JCR":null,"JCRName":null,"Score":null,"Total":0}
Pub Date : 2024-11-28DOI: 10.1016/j.phytochem.2024.114343
Hui-Lin Zhang , Na Wang , Xu-Liu Shi , Miao-Miao Wang , Qi-Meng Zhu , Jing Chang , Yan-Li Feng , Juan Zhang , Feng Qiu , Cheng-Peng Sun
The immune system serves as a role of diseases, such as Parkinson's disease, and acute lung injury. An immunoregulatory activity-directed separation depended on phorbol 12-myristate 13-acetate (PMA) plus ionomycin (Ion)-mediated Jurkat leukemic T cells was used for studying chemical constituents from Inula britannica L. in depth. Five previously undescribed aromatic sesquiterpenoid dimers inulabritanoids J−N (1−5) and a previously undescribed germacrane-type sesquiterpenoid britanicafanin F (6) were afforded from I. britannica as well as eight known sesquiterpenoids (7–14). Their structures were elucidated through 1D and 2D NMR, HRMS, and ECD spectra along with quantum chemical calculations. Immunomodulatory effects of compounds 1–14 were assayed in PMA plus Ion-mediated Jurkat cells, and indicated that compounds 8, 9, and 13 displayed significantly inhibitory effects toward IL-2 and IFN-γ. Further investigation of mechanism of action revealed that compound 13 inhibited phosphorylations of p38, ERK, and JNK to suppress c-Jun and c-Fos expressions, resulting in blocking the nuclear translocation of AP-1 (a complex of c-Jun and c-Fos) to regulate mRNA expressions of IL-2 and IFN-γ. Molecular docking analysis demonstrated that compound 13 could enter into the cavity of p38, ERK, and JNK, and from hydrogen bond interactions with Gly33, Lys53 Ser154, and Asp168 for p38, Lys54, Glu71, Ser153, and Asp167 for ERK, and Met149 and Asn152 for JNK, which supported the abovementioned results. These findings suggested that sesquiterpenoids from the genus Inula served as immunomodulators for treating diseases involved in immune and inflammatory responses.
{"title":"Sesquiterpenoids from Inula britannica and their potential mechanism for immunomodulation","authors":"Hui-Lin Zhang , Na Wang , Xu-Liu Shi , Miao-Miao Wang , Qi-Meng Zhu , Jing Chang , Yan-Li Feng , Juan Zhang , Feng Qiu , Cheng-Peng Sun","doi":"10.1016/j.phytochem.2024.114343","DOIUrl":"10.1016/j.phytochem.2024.114343","url":null,"abstract":"<div><div>The immune system serves as a role of diseases, such as Parkinson's disease, and acute lung injury. An immunoregulatory activity-directed separation depended on phorbol 12-myristate 13-acetate (PMA) plus ionomycin (Ion)-mediated Jurkat leukemic T cells was used for studying chemical constituents from <em>Inula britannica</em> L. in depth<em>.</em> Five previously undescribed aromatic sesquiterpenoid dimers inulabritanoids J−N (<strong>1−5</strong>) and a previously undescribed germacrane-type sesquiterpenoid britanicafanin F (<strong>6</strong>) were afforded from <em>I</em>. <em>britannica</em> as well as eight known sesquiterpenoids (<strong>7</strong>–<strong>14</strong>). Their structures were elucidated through 1D and 2D NMR, HRMS, and ECD spectra along with quantum chemical calculations. Immunomodulatory effects of compounds <strong>1</strong>–<strong>14</strong> were assayed in PMA plus Ion-mediated Jurkat cells, and indicated that compounds <strong>8</strong>, <strong>9</strong>, and <strong>13</strong> displayed significantly inhibitory effects toward IL-2 and IFN-<em>γ</em>. Further investigation of mechanism of action revealed that compound <strong>13</strong> inhibited phosphorylations of p38, ERK, and JNK to suppress c-Jun and c-Fos expressions, resulting in blocking the nuclear translocation of AP-1 (a complex of c-Jun and c-Fos) to regulate mRNA expressions of IL-2 and IFN-<em>γ</em>. Molecular docking analysis demonstrated that compound <strong>13</strong> could enter into the cavity of p38, ERK, and JNK, and from hydrogen bond interactions with Gly33, Lys53 Ser154, and Asp168 for p38, Lys54, Glu71, Ser153, and Asp167 for ERK, and Met149 and Asn152 for JNK, which supported the abovementioned results. These findings suggested that sesquiterpenoids from the genus <em>Inula</em> served as immunomodulators for treating diseases involved in immune and inflammatory responses.</div></div>","PeriodicalId":20170,"journal":{"name":"Phytochemistry","volume":"231 ","pages":"Article 114343"},"PeriodicalIF":3.2,"publicationDate":"2024-11-28","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"142755529","PeriodicalName":null,"FirstCategoryId":null,"ListUrlMain":null,"RegionNum":2,"RegionCategory":"生物学","ArticlePicture":[],"TitleCN":null,"AbstractTextCN":null,"PMCID":"","EPubDate":null,"PubModel":null,"JCR":null,"JCRName":null,"Score":null,"Total":0}
Pub Date : 2024-11-28DOI: 10.1016/j.phytochem.2024.114341
Shi-qi Liu , Qing-ling Xie , Ya-si Deng , Ling Liang , Han-wen Yuan , Bin Li , Huang-he Yu , Xing Tian , Yi-xing Qiu , Guy Paulin Kemayou Mouthe , Nuzhat Shehla , Ye Zhang , Ze-bo Cai , Wei Wang , Yu-pei Yang
In this study, six compounds (four triterpenoids named heilaohutriterpenes A-D and two lignans name heilaohusuins F and G) together with 21 known compounds were isolated from roots of Kadsura coccinea (Lem.) A. C. Smith guided by molecular networking. Their structures were determined using a combination of HR-ESI-MS, 1D, 2D-NMR anatysis, NMR calculation, and electronic circular dichroism (ECD) calculations. Moreover, the ability of the isolated compounds to inhibit the proliferation of rheumatoid arthritis-fibroblastoid synovial (RA-FLS) cells was evaluated in vitro. Heilaohutriterpene B (2), heilaohutriterpene D (4), coccinone B (7), and kadsuralignan H (24) demonstrated significant inhibitory activities against RA-FLS cells, with IC50 values of 9.57 ± 0.84, 16.22 ± 1.71, 3.08 ± 1.59, and 19.09 ± 2.42 μM, respectively. Meanwhile, western blotting analysis revealed that compound 2 down-regulated the level of P–NF-κB p65 and up-regulated that of Bax and IκBα. These results collectively suggest that compound 2 promoted the apoptosis of RA-FLS cells by inhibiting the NF-κB pathway. Taken together, this study contributed to the structural diversity of compounds derived from K. coccinea and lays a basis for further anti-RA-related studies.
{"title":"Targeted isolation of lignans and triterpenoids from kadsura coccinea by molecular networking and anti-RA-FLS activity","authors":"Shi-qi Liu , Qing-ling Xie , Ya-si Deng , Ling Liang , Han-wen Yuan , Bin Li , Huang-he Yu , Xing Tian , Yi-xing Qiu , Guy Paulin Kemayou Mouthe , Nuzhat Shehla , Ye Zhang , Ze-bo Cai , Wei Wang , Yu-pei Yang","doi":"10.1016/j.phytochem.2024.114341","DOIUrl":"10.1016/j.phytochem.2024.114341","url":null,"abstract":"<div><div>In this study, six compounds (four triterpenoids named heilaohutriterpenes A-D and two lignans name heilaohusuins F and G) together with 21 known compounds were isolated from roots of <em>Kadsura coccinea</em> (Lem.) A. C. Smith guided by molecular networking. Their structures were determined using a combination of HR-ESI-MS, 1D, 2D-NMR anatysis, NMR calculation, and electronic circular dichroism (ECD) calculations. Moreover, the ability of the isolated compounds to inhibit the proliferation of rheumatoid arthritis-fibroblastoid synovial (RA-FLS) cells was evaluated <em>in vitro</em>. Heilaohutriterpene B (<strong>2</strong>), heilaohutriterpene D (<strong>4</strong>), coccinone B (<strong>7</strong>), and kadsuralignan H (<strong>24</strong>) demonstrated significant inhibitory activities against RA-FLS cells, with IC<sub>50</sub> values of 9.57 ± 0.84, 16.22 ± 1.71, 3.08 ± 1.59, and 19.09 ± 2.42 μM, respectively. Meanwhile, western blotting analysis revealed that compound <strong>2</strong> down-regulated the level of <em>P</em>–NF-κB p65 and up-regulated that of Bax and IκBα. These results collectively suggest that compound <strong>2</strong> promoted the apoptosis of RA-FLS cells by inhibiting the NF-κB pathway. Taken together, this study contributed to the structural diversity of compounds derived from <em>K. coccinea</em> and lays a basis for further anti-RA-related studies.</div></div>","PeriodicalId":20170,"journal":{"name":"Phytochemistry","volume":"231 ","pages":"Article 114341"},"PeriodicalIF":3.2,"publicationDate":"2024-11-28","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"142755037","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}
Four undescribed cytochalasins (1−4), three undescribed orsellinic acid derivatives (5−7) and two known metabolites including methyl lecanorate (8) and methyl orsellinate (9) were isolated from the solid-state cultivation of a soil-derived fungus Trichocladium asperum SQ2-3 collected in Qinghai-Tibet Plateau. Their structures were elucidated by analysis of NMR (1D and 2D) and mass spectrometry data. The absolute configurations of 1−7 were assigned by a combination of the modified Mosher's method, microscale derivatization and Mo2(OAc)4-induced circular dichroism experiment. Compounds 1, 2, 3 and 6 showed significant cytotoxicity against HL-60, A3494, SMMC-7721, MDA-MB-231 and SW480 cell lines with IC50 values ranging from 4.74 to 15.84 μM, respectively. Meanwhile, compound 1 could obviously damage mitochondrial membrane potential and induce G2/M cell cycle arrest in A549 cells.
{"title":"Cytochalasins and orsellinic acid derivatives with cytotoxicity from the soil-derived fungus Trichocladium asperum","authors":"Yi-Jie Zhai , Shu-Hui Zhao , Jin-Ming Gao , Wen-Bo Han","doi":"10.1016/j.phytochem.2024.114340","DOIUrl":"10.1016/j.phytochem.2024.114340","url":null,"abstract":"<div><div>Four undescribed cytochalasins (<strong>1</strong>−<strong>4</strong>), three undescribed orsellinic acid derivatives (<strong>5</strong>−<strong>7</strong>) and two known metabolites including methyl lecanorate (<strong>8</strong>) and methyl orsellinate (<strong>9</strong>) were isolated from the solid-state cultivation of a soil-derived fungus <em>Trichocladium asperum</em> SQ2-3 collected in Qinghai-Tibet Plateau. Their structures were elucidated by analysis of NMR (1D and 2D) and mass spectrometry data. The absolute configurations of <strong>1</strong>−<strong>7</strong> were assigned by a combination of the modified Mosher's method, microscale derivatization and Mo<sub>2</sub>(OAc)<sub>4</sub>-induced circular dichroism experiment. Compounds <strong>1</strong>, <strong>2</strong>, <strong>3</strong> and <strong>6</strong> showed significant cytotoxicity against HL-60, A3494, SMMC-7721, MDA-MB-231 and SW480 cell lines with IC<sub>50</sub> values ranging from 4.74 to 15.84 μM, respectively. Meanwhile, compound <strong>1</strong> could obviously damage mitochondrial membrane potential and induce G2/M cell cycle arrest in A549 cells.</div></div>","PeriodicalId":20170,"journal":{"name":"Phytochemistry","volume":"231 ","pages":"Article 114340"},"PeriodicalIF":3.2,"publicationDate":"2024-11-26","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"142751018","PeriodicalName":null,"FirstCategoryId":null,"ListUrlMain":null,"RegionNum":2,"RegionCategory":"生物学","ArticlePicture":[],"TitleCN":null,"AbstractTextCN":null,"PMCID":"","EPubDate":null,"PubModel":null,"JCR":null,"JCRName":null,"Score":null,"Total":0}
Pub Date : 2024-11-26DOI: 10.1016/j.phytochem.2024.114339
Shaoqiang Fan , Jia Chen , Zhuo Zhang , Guohua Gong , Yu Mu , Dongsong Bai , Dan Zheng , Xueshi Huang , Liya Li
Ixeris chinensis is an edible and medicinal plant possessing anti-inflammatory activity. However, knowledge about the bioactive components of I. chinensis remains limited. Herein, comprehensive phytochemical study led to isolation and identification of 31 sesquiterpene lactones (SLs) from I. chinensis ethanol extract. Among them, 7 were previously undescribed guaianolides (1–4, 12–13, 24) and 16 were reported from this plant for the first time. Ixerisoside A (6) was proved to be the most predominant SL present in I. chinensis, and its content was determined as 0.34 ± 0.02% by HPLC-DAD method. Eleven SLs showed inhibition against NO production in LPS-induced RAW264.7 cells (IC50 value ranging from 12.13 to 31.10 μM). Compounds 6 and 13 could suppress IL-6 and IL-1β release, and down-regulate gene expression levels of IL-6, IL-1β, and iNOS. Network pharmacology study identified MAPK among those of the core targets of SLs against inflammation, which was validated by molecular docking. Cellular study proved that SLs could suppress phosphorylation of ERK and p38. Our work highlights therapeutic potential of SLs against inflammatory diseases, and offers valuable insights for developing I. chinensis as functional food in the nutraceutical industry.
{"title":"Characterization and anti-inflammatory investigation of sesquiterpene lactones from Ixeris chinensis","authors":"Shaoqiang Fan , Jia Chen , Zhuo Zhang , Guohua Gong , Yu Mu , Dongsong Bai , Dan Zheng , Xueshi Huang , Liya Li","doi":"10.1016/j.phytochem.2024.114339","DOIUrl":"10.1016/j.phytochem.2024.114339","url":null,"abstract":"<div><div><em>Ixeris chinensis</em> is an edible and medicinal plant possessing anti-inflammatory activity. However, knowledge about the bioactive components of <em>I. chinensis</em> remains limited. Herein, comprehensive phytochemical study led to isolation and identification of 31 sesquiterpene lactones (SLs) from <em>I. chinensis</em> ethanol extract. Among them, 7 were previously undescribed guaianolides (<strong>1</strong>–<strong>4</strong>, <strong>12</strong>–<strong>13</strong>, <strong>24</strong>) and 16 were reported from this plant for the first time. Ixerisoside A (<strong>6</strong>) was proved to be the most predominant SL present in <em>I. chinensis</em>, and its content was determined as 0.34 ± 0.02% by HPLC-DAD method. Eleven SLs showed inhibition against NO production in LPS-induced RAW264.7 cells (IC<sub>50</sub> value ranging from 12.13 to 31.10 μM). Compounds <strong>6</strong> and <strong>13</strong> could suppress IL-6 and IL-1β release, and down-regulate gene expression levels of <em>IL-6</em>, <em>IL-1β</em>, and <em>iNOS</em>. Network pharmacology study identified MAPK among those of the core targets of SLs against inflammation, which was validated by molecular docking. Cellular study proved that SLs could suppress phosphorylation of ERK and p38. Our work highlights therapeutic potential of SLs against inflammatory diseases, and offers valuable insights for developing <em>I. chinensis</em> as functional food in the nutraceutical industry.</div></div>","PeriodicalId":20170,"journal":{"name":"Phytochemistry","volume":"231 ","pages":"Article 114339"},"PeriodicalIF":3.2,"publicationDate":"2024-11-26","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"142740081","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}
Flavonoids are specialized metabolites that play important roles in plants, including interactions with the environment. The high structural diversity of this metabolite group is largely due to enzyme-mediated modifications of flavonoid core skeletons. In particular, glycosylation with different sugars is very common. In this study, the functions of the Arabidopsis thaliana glycoside hydrolase family 1-type glycosyltransferase proteins BGLU1, BGLU3, and BGLU4 were investigated, using a reverse genetics approach and untargeted metabolic fingerprinting. We screened for metabolic differences between A. thaliana wild type, loss-of-function mutants, and overexpression lines and partially identified differentially accumulating metabolites, which are putative products and/or substrates of the BGLU enzymes. Our study revealed that the investigated BGLU proteins are glycosyltransferases involved in the glycosylation of already glycosylated flavonoids using different substrates. While BGLU1 appears to be involved in the rhamnosylation of a kaempferol diglycoside in leaves, BGLU3 and BGLU4 are likely involved in the glycosylation of quercetin diglycosides in A. thaliana seeds. In addition, we present evidence that BGLU3 is a multifunctional enzyme that catalyzes other metabolic reactions with more complex substrates. This study deepens our understanding of the metabolic pathways and enzymes that contribute to the high structural diversity of flavonoids.
{"title":"Metabolic fingerprinting reveals roles of Arabidopsis thaliana BGLU1, BGLU3, and BGLU4 in glycosylation of various flavonoids","authors":"Jana-Freja Frommann , Boas Pucker , Lennart Malte Sielmann , Caroline Müller , Bernd Weisshaar , Ralf Stracke , Rabea Schweiger","doi":"10.1016/j.phytochem.2024.114338","DOIUrl":"10.1016/j.phytochem.2024.114338","url":null,"abstract":"<div><div>Flavonoids are specialized metabolites that play important roles in plants, including interactions with the environment. The high structural diversity of this metabolite group is largely due to enzyme-mediated modifications of flavonoid core skeletons. In particular, glycosylation with different sugars is very common. In this study, the functions of the <em>Arabidopsis thaliana</em> glycoside hydrolase family 1-type glycosyltransferase proteins BGLU1, BGLU3, and BGLU4 were investigated, using a reverse genetics approach and untargeted metabolic fingerprinting. We screened for metabolic differences between <em>A. thaliana</em> wild type, loss-of-function mutants, and overexpression lines and partially identified differentially accumulating metabolites, which are putative products and/or substrates of the BGLU enzymes. Our study revealed that the investigated BGLU proteins are glycosyltransferases involved in the glycosylation of already glycosylated flavonoids using different substrates. While BGLU1 appears to be involved in the rhamnosylation of a kaempferol diglycoside in leaves, BGLU3 and BGLU4 are likely involved in the glycosylation of quercetin diglycosides in <em>A. thaliana</em> seeds. In addition, we present evidence that BGLU3 is a multifunctional enzyme that catalyzes other metabolic reactions with more complex substrates. This study deepens our understanding of the metabolic pathways and enzymes that contribute to the high structural diversity of flavonoids.</div></div>","PeriodicalId":20170,"journal":{"name":"Phytochemistry","volume":"231 ","pages":"Article 114338"},"PeriodicalIF":3.2,"publicationDate":"2024-11-26","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"142740148","PeriodicalName":null,"FirstCategoryId":null,"ListUrlMain":null,"RegionNum":2,"RegionCategory":"生物学","ArticlePicture":[],"TitleCN":null,"AbstractTextCN":null,"PMCID":"OA","EPubDate":null,"PubModel":null,"JCR":null,"JCRName":null,"Score":null,"Total":0}
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