Pub Date : 2024-11-15DOI: 10.1016/j.phytochem.2024.114335
Wen-Chao Tu , Peng-Yun Yang , Xing-Jie Zhang , Yuan-Lin Kong , Bo Li , Hui-Juan Wang , Muhammad Aurang Zeb , Xiao-Li Li , Mei-Feng Liu , Wei-Lie Xiao
Orthosiphon wulfenioides is a medicinal plant to treat arthritis, vascular inflammation, edema, and dyspepsia. To explore the anti-inflammatory components and their mechanism of action, 12 previously undescribed highly oxidized diterpenes, wulfenioidones L−W (1−12), were isolated from O. wulfenioides by bioactivity orientation. Their structures were elucidated using HRESIMS, NMR, specific rotation, single-crystal X-ray diffraction, and ECD spectra analysis. Compounds 1−4 exhibited significant inhibition on LDH release by preventing macrophage J774A.1 pyroptosis. Compound 1 showed the most potent inhibitory effect with an IC50 value of 5.81 μM. It was revealed in the Western blot experiment that compound 1 not only significantly and dose-dependently decreased the activation of CASP1 and IL-1β, but also prevented GSDMD-FL from splitting into GSDMD-NT, the membrane pore-forming protein to release inflammatory factors, thus blocking the extracellular release of IL-1β. More interestingly, compound 1 not only blocked the activation of NLRP3 inflammasome, but also strikingly enhanced the orange fluorescence of JC-1 aggregates, thus showing the activity of maintaining mitochondrial membrane potential and reversing mitochondria damage.
{"title":"Bioactivity-guided isolation of potent inflammasome and mitochondria damage inhibitory diterpenoids from Orthosiphon wulfenioides","authors":"Wen-Chao Tu , Peng-Yun Yang , Xing-Jie Zhang , Yuan-Lin Kong , Bo Li , Hui-Juan Wang , Muhammad Aurang Zeb , Xiao-Li Li , Mei-Feng Liu , Wei-Lie Xiao","doi":"10.1016/j.phytochem.2024.114335","DOIUrl":"10.1016/j.phytochem.2024.114335","url":null,"abstract":"<div><div><em>Orthosiphon wulfenioides</em> is a medicinal plant to treat arthritis, vascular inflammation, edema, and dyspepsia. To explore the anti-inflammatory components and their mechanism of action, 12 previously undescribed highly oxidized diterpenes, wulfenioidones L−W (<strong>1</strong>−<strong>12</strong>), were isolated from <em>O. wulfenioides</em> by bioactivity orientation. Their structures were elucidated using HRESIMS, NMR, specific rotation, single-crystal X-ray diffraction, and ECD spectra analysis. Compounds <strong>1</strong>−<strong>4</strong> exhibited significant inhibition on LDH release by preventing macrophage J774A.1 pyroptosis. Compound <strong>1</strong> showed the most potent inhibitory effect with an IC<sub>50</sub> value of 5.81 μM. It was revealed in the Western blot experiment that compound <strong>1</strong> not only significantly and dose-dependently decreased the activation of CASP1 and IL-1<em>β</em>, but also prevented GSDMD-FL from splitting into GSDMD-NT, the membrane pore-forming protein to release inflammatory factors, thus blocking the extracellular release of IL-1<em>β</em>. More interestingly, compound <strong>1</strong> not only blocked the activation of NLRP3 inflammasome, but also strikingly enhanced the orange fluorescence of JC-1 aggregates, thus showing the activity of maintaining mitochondrial membrane potential and reversing mitochondria damage.</div></div>","PeriodicalId":20170,"journal":{"name":"Phytochemistry","volume":"230 ","pages":"Article 114335"},"PeriodicalIF":3.2,"publicationDate":"2024-11-15","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"142644292","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 : 2024-11-15DOI: 10.1016/j.phytochem.2024.114329
Olivier Potterat , Marina Kaufmann , Cécile Tschopp , Michaela Caj , Jakob K. Reinhardt , Alessandro Prescimone , Devika Shah , Stephan Baumgartner , Michel-Angelo Sciotti , Laura Suter-Dick
Twelve bufadienolides and six 19-norbufadienolides were isolated from the aerial parts of Helleborus foetidus. They consist of aglycons and glucosides and include nine previously undescribed compounds and a compound reported for the first time as a genuine natural product. Their structures were established by extensive spectroscopic analysis and the structure and absolute configuration of two previously unreported 3,4-epoxy derivatives were confirmed by single crystal X-ray diffraction analysis. The compounds were tested for their cytotoxicity on MCF-7 human breast cancer cells. They show differential cytotoxic activity with IC50 values in the range of 2.4 nM - >10 μM. The potency of the activity strongly correlates with the presence of a C-19 aldehyde group. The data complement the scientific basis underpinning the use of H. foetidus in anthroposophic medicine for the integrative treatment of cancer.
{"title":"Bufadienolides from Helleborus foetidus and their cytotoxic properties on MCF-7 breast cancer cells","authors":"Olivier Potterat , Marina Kaufmann , Cécile Tschopp , Michaela Caj , Jakob K. Reinhardt , Alessandro Prescimone , Devika Shah , Stephan Baumgartner , Michel-Angelo Sciotti , Laura Suter-Dick","doi":"10.1016/j.phytochem.2024.114329","DOIUrl":"10.1016/j.phytochem.2024.114329","url":null,"abstract":"<div><div>Twelve bufadienolides and six 19-norbufadienolides were isolated from the aerial parts of <em>Helleborus foetidus</em>. They consist of aglycons and glucosides and include nine previously undescribed compounds and a compound reported for the first time as a genuine natural product. Their structures were established by extensive spectroscopic analysis and the structure and absolute configuration of two previously unreported 3,4-epoxy derivatives were confirmed by single crystal X-ray diffraction analysis. The compounds were tested for their cytotoxicity on MCF-7 human breast cancer cells. They show differential cytotoxic activity with IC<sub>50</sub> values in the range of 2.4 nM - >10 μM. The potency of the activity strongly correlates with the presence of a C-19 aldehyde group. The data complement the scientific basis underpinning the use of <em>H. foetidus</em> in anthroposophic medicine for the integrative treatment of cancer.</div></div>","PeriodicalId":20170,"journal":{"name":"Phytochemistry","volume":"230 ","pages":"Article 114329"},"PeriodicalIF":3.2,"publicationDate":"2024-11-15","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"142644293","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}
Pub Date : 2024-11-15DOI: 10.1016/j.phytochem.2024.114336
Bang-Yin Tan , Hua Lin , Heng-Gang Zhang , Jing-Zhi Zhao , Shi-Yu Deng , Rui-Rong Guo , Xin Wei , Lan-Chun Zhang , Rong-Ping Zhang , Hao-Fei Yu
Chemical investigation of the native medicinal plant Tabernaemontana bovina led to the isolation of five previously unreported monoterpenoid indole alkaloids tabernovinaines A-E (1–5) together with twenty-seven known analogs (6–32), including a bisindole alkaloid 1 with the (E)-4-aminobut-3-en-2-one fragment, as well as a unique cage skeleton 2 containing 6/5/8/6/6 ring system. The chemical structures of these unreported compounds were elucidated using mass spectrometry, NMR spectroscopy, circular dichroism, density functional theory calculations, and derivatizations. The activity evaluation shows that the bisindole alkaloid 1 revealed a potential cytotoxic effect by inducing HepG2 cell apoptosis and damaging clonal sphere expansion.
{"title":"Cytotoxic monoterpenoid indole alkaloids from Tabernaemontana bovina","authors":"Bang-Yin Tan , Hua Lin , Heng-Gang Zhang , Jing-Zhi Zhao , Shi-Yu Deng , Rui-Rong Guo , Xin Wei , Lan-Chun Zhang , Rong-Ping Zhang , Hao-Fei Yu","doi":"10.1016/j.phytochem.2024.114336","DOIUrl":"10.1016/j.phytochem.2024.114336","url":null,"abstract":"<div><div>Chemical investigation of the native medicinal plant <em>Tabernaemontana bovina</em> led to the isolation of five previously unreported monoterpenoid indole alkaloids tabernovinaines A-E (<strong>1</strong>–<strong>5</strong>) together with twenty-seven known analogs (<strong>6</strong>–<strong>32</strong>), including a bisindole alkaloid <strong>1</strong> with the (<em>E</em>)-4-aminobut-3-en-2-one fragment, as well as a unique cage skeleton <strong>2</strong> containing 6/5/8/6/6 ring system. The chemical structures of these unreported compounds were elucidated using mass spectrometry, NMR spectroscopy, circular dichroism, density functional theory calculations, and derivatizations. The activity evaluation shows that the bisindole alkaloid <strong>1</strong> revealed a potential cytotoxic effect by inducing HepG2 cell apoptosis and damaging clonal sphere expansion.</div></div>","PeriodicalId":20170,"journal":{"name":"Phytochemistry","volume":"230 ","pages":"Article 114336"},"PeriodicalIF":3.2,"publicationDate":"2024-11-15","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"142644294","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 : 2024-11-15DOI: 10.1016/j.phytochem.2024.114337
Zi Kang Meng , Si Min Rao , Yu Kai Hu , Xuan Zhou , Qian Yang , Ren Xiang Tan , Yi Shuang Wang
Endophytic actinomycetes exhibit considerable potential for the production of biologically active metabolites due to their coevolution with plant hosts. In this study, an endophytic Streptomyces chartreusis M7 was isolated from Houttuynia cordata Thunb. Bioactivity-guided investigation of the metabolites produced by this strain led to the identification of thirteen anthracycline-derived polyketides, including five unreported anthraquinones designated streptoquinones A-E (1–5) and two undescribed angular polyketides named chartins A and B (6–7) along with six knowns. Their structures were elucidated through comprehensive spectroscopic analysis and ECD calculations. Notably, chartins A (6) and B (7) feature angular tetracyclic and pentacyclic skeletons, respectively, which have undergone several oxidative rearrangements. Moreover, streptoquinone A (1) exhibited moderate cytotoxicity against A549 cells, with an IC50 value of 4.8 μM.
{"title":"Discovery of undescribed anthracycline-derived polyketides with cytotoxicity from endophytic Streptomyces chartreusis M7","authors":"Zi Kang Meng , Si Min Rao , Yu Kai Hu , Xuan Zhou , Qian Yang , Ren Xiang Tan , Yi Shuang Wang","doi":"10.1016/j.phytochem.2024.114337","DOIUrl":"10.1016/j.phytochem.2024.114337","url":null,"abstract":"<div><div>Endophytic actinomycetes exhibit considerable potential for the production of biologically active metabolites due to their coevolution with plant hosts. In this study, an endophytic <em>Streptomyces chartreusis</em> M7 was isolated from <em>Houttuynia cordata</em> Thunb. Bioactivity-guided investigation of the metabolites produced by this strain led to the identification of thirteen anthracycline-derived polyketides, including five unreported anthraquinones designated streptoquinones A-E (<strong>1</strong>–<strong>5</strong>) and two undescribed angular polyketides named chartins A and B (<strong>6</strong>–<strong>7</strong>) along with six knowns. Their structures were elucidated through comprehensive spectroscopic analysis and ECD calculations. Notably, chartins A (<strong>6</strong>) and B (<strong>7</strong>) feature angular tetracyclic and pentacyclic skeletons, respectively, which have undergone several oxidative rearrangements. Moreover, streptoquinone A (<strong>1</strong>) exhibited moderate cytotoxicity against A549 cells, with an IC<sub>50</sub> value of 4.8 μM.</div></div>","PeriodicalId":20170,"journal":{"name":"Phytochemistry","volume":"230 ","pages":"Article 114337"},"PeriodicalIF":3.2,"publicationDate":"2024-11-15","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"142644295","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 : 2024-11-14DOI: 10.1016/j.phytochem.2024.114333
Hai-Hui Guo , Chun-Xu Li , Min Yang , Feng-Feng Li , Hui-Yun Yang , Ming Yin , Jia-Peng Wang , Fu-Sheng Wang
Gentidelasides A−G (1−7) seven unreported loganin derivatives and fourteen known compounds (8−21) were isolated from the flowers of Gentiana delavayi Franch. Their structures including absolute configurations were unambiguously elucidated by analysis of extensive NMR spectroscopy, ECD, and HRESIMS, as well as enzymatic hydrolysis. In vitro bioassay, compound 7 showed obvious inhibitory effects on the production of Aβ40 and Aβ42, with IC50 values of 0.052 ± 0.0023 nM and 1.52 ± 0.95 nM, respectively, which probably exert their prevention of Alzheimer's disease by inhibiting the expression of β-site amyloid precursor protein cleaving enzyme 1. The molecular docking simulation revealed that compound 7 inhibited BACE1 through hydrophilic and hydrophobic interactions in the active site cavities.
{"title":"Gentidelasides A−G: Loganin derivatives from Gentiana delavayi with reducing Aβ secretion via suppressing BACE1 expression","authors":"Hai-Hui Guo , Chun-Xu Li , Min Yang , Feng-Feng Li , Hui-Yun Yang , Ming Yin , Jia-Peng Wang , Fu-Sheng Wang","doi":"10.1016/j.phytochem.2024.114333","DOIUrl":"10.1016/j.phytochem.2024.114333","url":null,"abstract":"<div><div>Gentidelasides A−G (<strong>1</strong>−<strong>7</strong>) seven unreported loganin derivatives and fourteen known compounds (<strong>8</strong>−<strong>21</strong>) were isolated from the flowers of <em>Gentiana delavayi</em> Franch. Their structures including absolute configurations were unambiguously elucidated by analysis of extensive NMR spectroscopy, ECD, and HRESIMS, as well as enzymatic hydrolysis. <em>In vitro</em> bioassay, compound <strong>7</strong> showed obvious inhibitory effects on the production of A<em>β</em>40 and A<em>β</em>42, with IC<sub>50</sub> values of 0.052 ± 0.0023 nM and 1.52 ± 0.95 nM, respectively, which probably exert their prevention of Alzheimer's disease by inhibiting the expression of <em>β</em>-site amyloid precursor protein cleaving enzyme 1. The molecular docking simulation revealed that compound <strong>7</strong> inhibited BACE1 through hydrophilic and hydrophobic interactions in the active site cavities.</div></div>","PeriodicalId":20170,"journal":{"name":"Phytochemistry","volume":"230 ","pages":"Article 114333"},"PeriodicalIF":3.2,"publicationDate":"2024-11-14","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"142639453","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 : 2024-11-14DOI: 10.1016/j.phytochem.2024.114330
Chae-Yeong An , Pisey Pel , Mingoo Bae , Chan-Woong Park , Haeun Kwon , Hyun Suk Lee , Luong Van Dung , Changmu Kim , Dongho Lee , Young Hee Choi , Young-Won Chin
Nine previously undescribed (1–9) and seven known (10–16) cycloartane-type triterpenoids were isolated and characterized from Combretum quadrangulare Kurz using physicochemical and spectroscopic methods. The absolute configurations of these compounds were determined through modified Mosher's method and quantum chemical calculation of electronic circular dichroism (ECD) and vibrational circular dichroism (VCD) spectra. Their inhibitory activities against PCSK9 secretion were assessed, and a plausible structure-activity relationship was delineated. Compounds 2, 14, and 15 exhibited notable inhibitory effects on PCSK9 mRNA and protein levels, and significant PCSK9 mRNA inhibition was observed when co-treated with atorvastatin. Compound 15 showed the most potent activity, markedly enhancing LDL uptake compared to the negative control. In vivo pharmacokinetic studies confirmed that compound 15 exhibited higher distribution in the liver than plasma, where PCSK9 is predominantly synthesized. These findings emphasize the potential significance of the cycloartane-type triterpenoid scaffold in discovering PCSK9 inhibitors.
{"title":"Cycloartane-type triterpenoids from Combretum quadrangulare Kurz with PCSK9 secretion inhibitory activities","authors":"Chae-Yeong An , Pisey Pel , Mingoo Bae , Chan-Woong Park , Haeun Kwon , Hyun Suk Lee , Luong Van Dung , Changmu Kim , Dongho Lee , Young Hee Choi , Young-Won Chin","doi":"10.1016/j.phytochem.2024.114330","DOIUrl":"10.1016/j.phytochem.2024.114330","url":null,"abstract":"<div><div>Nine previously undescribed (<strong>1</strong>–<strong>9</strong>) and seven known (<strong>10</strong>–<strong>16</strong>) cycloartane-type triterpenoids were isolated and characterized from <em>Combretum quadrangulare</em> Kurz using physicochemical and spectroscopic methods. The absolute configurations of these compounds were determined through modified Mosher's method and quantum chemical calculation of electronic circular dichroism (ECD) and vibrational circular dichroism (VCD) spectra. Their inhibitory activities against PCSK9 secretion were assessed, and a plausible structure-activity relationship was delineated. Compounds <strong>2</strong>, <strong>14</strong>, and <strong>15</strong> exhibited notable inhibitory effects on PCSK9 mRNA and protein levels, and significant PCSK9 mRNA inhibition was observed when co-treated with atorvastatin. Compound <strong>15</strong> showed the most potent activity, markedly enhancing LDL uptake compared to the negative control. <em>In vivo</em> pharmacokinetic studies confirmed that compound <strong>15</strong> exhibited higher distribution in the liver than plasma, where PCSK9 is predominantly synthesized. These findings emphasize the potential significance of the cycloartane-type triterpenoid scaffold in discovering PCSK9 inhibitors.</div></div>","PeriodicalId":20170,"journal":{"name":"Phytochemistry","volume":"230 ","pages":"Article 114330"},"PeriodicalIF":3.2,"publicationDate":"2024-11-14","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"142639451","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 : 2024-11-14DOI: 10.1016/j.phytochem.2024.114334
Yang Fu , Jingya Ruan , Ping Zhang , Wei Zhang , Dingshan Yang , Yaqi Zhang , Zhunan Dang , Yi Zhang , Tao Wang
Multiple spectroscopic, chromatographic, and chemical reaction methods were combined to investigate the chemical components in the fruits of Elaeagnus angustifolia L. As results, thirty-two compounds were obtained from it as natural products. Six of them, elangphenosides A (1), B (2), C (3) and D (4), elangmegastigmanoside A (5), and elangorganic acid A1 (6) were retrieved by Scifinder as previously undescribed ones. Additionally, a previously undescribed artificial product, elangorganic acid A2, as well as a known artificial one, (3R) 5-ethoxy-3-(ethoxycarbonyl)-3-hydroxy-5-oxopentanoic acid, were yielded. Following the phytochemical investigation, LC-MS analysis was employed to conduct a systematical characterization of the constituents from E. angustifolia fruits. Ultimately, fifty-six compounds, including seventeen phenols, one ionone, twenty-four triterpenes, and fourteen other ones, were unambiguously detected and identified. Moreover, in vitro anti-inflammatory activity screening of forty-four natural compounds presented in E. angustifolia fruits was performed by using the LPS-induced RAW264.7 cell model. Twenty-six compounds, including phenols, organic acids, and other compounds, showed assignable activity. Furthermore, their structure-activity relationships were summarized. Combined with the previous research work in our lab, triterpenes, phenols, and organic acids were speculated to be key components during the E. angustifolia fruits exerting anti-inflammatory activity. In summary, this article fully explored the chemical composition of E. angustifolia fruits, assayed their in vitro NO production inhibitory effects, greatly expanding its material foundation and laying a solid foundation for further research and development.
结合光谱法、色谱法和化学反应法等多种方法，研究了鹅掌楸（Elaeagnus angustifolia L.）果实中的化学成分。Scifinder 检索到了其中六种化合物，即鹅掌楸苷 A (1)、B (2)、C (3)和 D (4)，鹅掌楸黄芪苷 A (5)，以及鹅掌楸无机酸 A1 (6)，它们是以前未曾描述过的化合物。此外，还得到了一种以前未曾描述过的人工产物--鞣花有机酸 A2，以及一种已知的人工产物--(3R) 5-乙氧基-3-（乙氧基羰基）-3-羟基-5-氧代戊酸。植物化学研究之后，采用 LC-MS 分析法对 E. angustifolia 果实中的成分进行了系统表征。最终，明确检测并鉴定出 56 种化合物，包括 17 种酚类、1 种离子酮、24 种三萜类和 14 种其他化合物。此外，利用 LPS 诱导的 RAW264.7 细胞模型，对 E. angustifolia 果实中的 44 种天然化合物进行了体外抗炎活性筛选。包括酚类、有机酸和其他化合物在内的 26 种化合物显示出了可分配的活性。此外，还总结了这些化合物的结构-活性关系。结合我们实验室之前的研究工作，推测三萜类、酚类和有机酸是 E. angustifolia 果实中具有抗炎活性的关键成分。综上所述，本文充分探讨了白头翁果实的化学成分，测定了其体外抑制NO生成的作用，极大地拓展了其物质基础，为进一步的研究和开发奠定了坚实的基础。
{"title":"The bioactive constituents from the fruits of Elaeagnus angustifolia L.","authors":"Yang Fu , Jingya Ruan , Ping Zhang , Wei Zhang , Dingshan Yang , Yaqi Zhang , Zhunan Dang , Yi Zhang , Tao Wang","doi":"10.1016/j.phytochem.2024.114334","DOIUrl":"10.1016/j.phytochem.2024.114334","url":null,"abstract":"<div><div>Multiple spectroscopic, chromatographic, and chemical reaction methods were combined to investigate the chemical components in the fruits of <em>Elaeagnus angustifolia</em> L. As results, thirty-two compounds were obtained from it as natural products. Six of them, elangphenosides A (<strong>1</strong>), B (<strong>2</strong>), C (<strong>3</strong>) and D (<strong>4</strong>), elangmegastigmanoside A (<strong>5</strong>), and elangorganic acid A<sub>1</sub> (<strong>6</strong>) were retrieved by Scifinder as previously undescribed ones. Additionally, a previously undescribed artificial product, elangorganic acid A<sub>2</sub>, as well as a known artificial one, (3<em>R</em>) 5-ethoxy-3-(ethoxycarbonyl)-3-hydroxy-5-oxopentanoic acid, were yielded. Following the phytochemical investigation, LC-MS analysis was employed to conduct a systematical characterization of the constituents from <em>E. angustifolia</em> fruits. Ultimately, fifty-six compounds, including seventeen phenols, one ionone, twenty-four triterpenes, and fourteen other ones, were unambiguously detected and identified. Moreover, <em>in vitro</em> anti-inflammatory activity screening of forty-four natural compounds presented in <em>E. angustifolia</em> fruits was performed by using the LPS-induced RAW264.7 cell model. Twenty-six compounds, including phenols, organic acids, and other compounds, showed assignable activity. Furthermore, their structure-activity relationships were summarized. Combined with the previous research work in our lab, triterpenes, phenols, and organic acids were speculated to be key components during the <em>E. angustifolia</em> fruits exerting anti-inflammatory activity. In summary, this article fully explored the chemical composition of <em>E. angustifolia</em> fruits, assayed their <em>in vitro</em> NO production inhibitory effects, greatly expanding its material foundation and laying a solid foundation for further research and development.</div></div>","PeriodicalId":20170,"journal":{"name":"Phytochemistry","volume":"230 ","pages":"Article 114334"},"PeriodicalIF":3.2,"publicationDate":"2024-11-14","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"142644296","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 : 2024-11-14DOI: 10.1016/j.phytochem.2024.114332
Patrycja Wojtaczka , Anna Ciarkowska , Marta Krawczak , Jacek Kęsy , Junio Flores Castellanos , Joerg Fettke , Maciej Ostrowski
Osmotic shock is the first step of high salt or drought action that involves biochemical and molecular changes during plant response to these unfavorable conditions. Indole-3-acetyl-aspartate (IAA-aspartate, IAA-Asp) is the main amide conjugate of auxin in pea (Pisum sativum L.) tissues. Although the exact molecular mechanism of the IAA-Asp action is unknown, this conjugate's indole-3-acetic acid (IAA)-independent biological activity has been observed during physiological and stress conditions. In this work, we investigated the effect of IAA-Asp alone, as well as in combination with NaCl or polyethylene glycol (PEG) (osmotic shock) on reduced/oxidized glutathione (GSH/GSSG) ratio, activities of enzymes modulating glutathione concentration, protein S-glutathionylation, and IAA homeostasis. We did not observe the hydrolysis of IAA-Asp to IAA in pea seedlings, which, together with other results, suggests that IAA-Asp modulates plant response to abiotic stimuli independently of IAA. Moreover, despite the effect of IAA-Asp on the enzymes responsible for IAA conjugation, no changes in this phytohormone level were visible. Furthermore, 3h plant treatment with IAA-Asp increased the activity of glutathione reductase (GR), which correlates with an elevated GSH/GSSG ratio. On the contrary, more extended (48h) incubation with IAA-Asp diminished the GSH/GSSG ratio and increased the activity of glutathione peroxidase (GPX). IAA-Asp reduced GR activity during salt treatment but did not affect the GSH/GSSG ratio. Similarly, under plant incubation with PEG, IAA-Asp did not change the GSH/GSSG ratio but increased glutathione S-transferase (GST) activity. We also analyzed the effect of IAA-Asp on pea protein S-glutathionylation. Increased S-glutathionylation of heat shock 70 kDa protein (HSP70) was observed after plant treatment with IAA-Asp, PEG, or IAA-Asp combined with PEG. The proteomic analysis also revealed that IAA-Asp diminished S-glutathionylation of lipoxygenase during plant incubation with PEG. Thus, we suggest that IAA-Asp modulates redox status in pea during oxidative stress and under normal physiological conditions.
{"title":"Biochemical and proteomic approaches to investigating effects of IAA-aspartate in pea (Pisum sativum L.) seedlings during osmotic shock","authors":"Patrycja Wojtaczka , Anna Ciarkowska , Marta Krawczak , Jacek Kęsy , Junio Flores Castellanos , Joerg Fettke , Maciej Ostrowski","doi":"10.1016/j.phytochem.2024.114332","DOIUrl":"10.1016/j.phytochem.2024.114332","url":null,"abstract":"<div><div>Osmotic shock is the first step of high salt or drought action that involves biochemical and molecular changes during plant response to these unfavorable conditions. Indole-3-acetyl-aspartate (IAA-aspartate, IAA-Asp) is the main amide conjugate of auxin in pea (<em>Pisum sativum</em> L.) tissues. Although the exact molecular mechanism of the IAA-Asp action is unknown, this conjugate's indole-3-acetic acid (IAA)-independent biological activity has been observed during physiological and stress conditions. In this work, we investigated the effect of IAA-Asp alone, as well as in combination with NaCl or polyethylene glycol (PEG) (osmotic shock) on reduced/oxidized glutathione (GSH/GSSG) ratio, activities of enzymes modulating glutathione concentration, protein S-glutathionylation, and IAA homeostasis. We did not observe the hydrolysis of IAA-Asp to IAA in pea seedlings, which, together with other results, suggests that IAA-Asp modulates plant response to abiotic stimuli independently of IAA. Moreover, despite the effect of IAA-Asp on the enzymes responsible for IAA conjugation, no changes in this phytohormone level were visible. Furthermore, 3h plant treatment with IAA-Asp increased the activity of glutathione reductase (GR), which correlates with an elevated GSH/GSSG ratio. On the contrary, more extended (48h) incubation with IAA-Asp diminished the GSH/GSSG ratio and increased the activity of glutathione peroxidase (GPX). IAA-Asp reduced GR activity during salt treatment but did not affect the GSH/GSSG ratio. Similarly, under plant incubation with PEG, IAA-Asp did not change the GSH/GSSG ratio but increased glutathione S-transferase (GST) activity. We also analyzed the effect of IAA-Asp on pea protein S-glutathionylation. Increased S-glutathionylation of heat shock 70 kDa protein (HSP70) was observed after plant treatment with IAA-Asp, PEG, or IAA-Asp combined with PEG. The proteomic analysis also revealed that IAA-Asp diminished S-glutathionylation of lipoxygenase during plant incubation with PEG. Thus, we suggest that IAA-Asp modulates redox status in pea during oxidative stress and under normal physiological conditions.</div></div>","PeriodicalId":20170,"journal":{"name":"Phytochemistry","volume":"230 ","pages":"Article 114332"},"PeriodicalIF":3.2,"publicationDate":"2024-11-14","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"142639450","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 : 2024-11-14DOI: 10.1016/j.phytochem.2024.114331
Huynh Nguyen Khanh Tran , Long Hoang To , Soo-Jin Heo , Eun-A Kim , Nalae Kang , Min Jin Kim , Le Viet Ha Tran , Yeon-Ju Lee
Twelve neomanoalide derivatives (1–12) and two halisulfate derivatives (13 and 14), nine of which are unprecedented (4–9, 11, 12, and 14; coscilides A–H and halisulfate 11, respectively), were isolated from the sponge Coscinoderma bakusi. The previously unreported neomanoalide derivatives show distinct features in their 6,7-double bond geometry (4 and 9) or terpenoid moieties (5–8, 11, and 12) compared to the reported ones, as elucidated using NMR spectroscopy and HRMS analysis. Among these derivatives, compounds 11 and 12 contain terpenoid moieties that are rarely found in marine natural products. The isolated compounds showed low activity against hTRPA1, six pathogenic bacterial strains, 10 cancer cell lines, except in the case of 7, which exhibited activity against hTRPA1 (IC50, 34.5 μM) and Staphylococcus aureus (MIC, 32.0 μg/mL). The halisulfate derivative 14 inhibited NO production in LPS-activated RAW 246.7 macrophage by 45% at a concentration of 10.0 μM. Although no significant activity was observed for the compounds in this study, the compounds reported herein would contribute to the chemical diversity of marine sesterterpenoids.
{"title":"Sesterterpenoids isolated from the marine sponge Coscinoderma bakusi","authors":"Huynh Nguyen Khanh Tran , Long Hoang To , Soo-Jin Heo , Eun-A Kim , Nalae Kang , Min Jin Kim , Le Viet Ha Tran , Yeon-Ju Lee","doi":"10.1016/j.phytochem.2024.114331","DOIUrl":"10.1016/j.phytochem.2024.114331","url":null,"abstract":"<div><div>Twelve neomanoalide derivatives (<strong>1</strong>–<strong>12</strong>) and two halisulfate derivatives (<strong>13</strong> and <strong>14</strong>), nine of which are unprecedented (<strong>4</strong>–<strong>9</strong>, <strong>11</strong>, <strong>12</strong>, and <strong>14</strong>; coscilides A–H and halisulfate 11, respectively), were isolated from the sponge <em>Coscinoderma bakusi</em>. The previously unreported neomanoalide derivatives show distinct features in their 6,7-double bond geometry (<strong>4</strong> and <strong>9</strong>) or terpenoid moieties (<strong>5</strong>–<strong>8</strong>, <strong>11</strong>, and <strong>12</strong>) compared to the reported ones, as elucidated using NMR spectroscopy and HRMS analysis. Among these derivatives, compounds <strong>11</strong> and <strong>12</strong> contain terpenoid moieties that are rarely found in marine natural products. The isolated compounds showed low activity against hTRPA1, six pathogenic bacterial strains, 10 cancer cell lines, except in the case of <strong>7</strong>, which exhibited activity against hTRPA1 (IC<sub>50</sub>, 34.5 μM) and <em>Staphylococcus aureus</em> (MIC, 32.0 μg/mL). The halisulfate derivative <strong>14</strong> inhibited NO production in LPS-activated RAW 246.7 macrophage by 45% at a concentration of 10.0 μM. Although no significant activity was observed for the compounds in this study, the compounds reported herein would contribute to the chemical diversity of marine sesterterpenoids.</div></div>","PeriodicalId":20170,"journal":{"name":"Phytochemistry","volume":"230 ","pages":"Article 114331"},"PeriodicalIF":3.2,"publicationDate":"2024-11-14","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"142639454","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 : 2024-11-08DOI: 10.1016/j.phytochem.2024.114316
Peixin Shi, Xiaohui Yu, Min Zhang, Lin Wang, Linkui Deng, Jun Yin, Na Han
Fourteen benzofuran compounds were identified in the fruits of Psoralea corylifolia L., with four previously undescribed compounds (4, 9–11) being discovered. Their chemical structures were definitively determined through comprehensive spectral data analysis. The compounds were investigated for their antioxidant, anti-tumor, and anti-inflammatory properties, revealing that benzofuran compounds exhibit significant anti-inflammatory effects. Compound 2 demonstrated the most potent anti-inflammatory effect, surpassing that of the positive control drug. The potential anti-inflammatory mechanism of 2 was extensively explored through network pharmacology research. Subsequent validation of the selected targets via Western blot analysis confirmed that 2 exerts its anti-inflammatory effects by activating the TLR4/NF-κB pathway. These findings offer a novel perspective on the development of benzofuran glycoside compounds and Psoralea fructus.
在 Psoralea corylifolia L. 果实中鉴定出 14 种苯并呋喃类化合物，其中发现了 4 种以前未曾描述过的化合物（4, 9-11）。通过全面的光谱数据分析，确定了这些化合物的化学结构。研究人员对这些化合物的抗氧化、抗肿瘤和抗炎特性进行了研究，发现苯并呋喃类化合物具有显著的抗炎作用。化合物 2 的抗炎效果最强，超过了阳性对照药物。通过网络药理学研究，对 2 的潜在抗炎机制进行了广泛探索。随后通过 Western 印迹分析对所选靶点进行验证，证实 2 通过激活 TLR4/NF-κB 通路发挥抗炎作用。这些发现为苯并呋喃苷类化合物和红景天的开发提供了一个新的视角。
{"title":"Biological activities of benzofurans from the fruits of Psoralea corylifolia L. and their mechanism based on network pharmacology and biological verification","authors":"Peixin Shi, Xiaohui Yu, Min Zhang, Lin Wang, Linkui Deng, Jun Yin, Na Han","doi":"10.1016/j.phytochem.2024.114316","DOIUrl":"10.1016/j.phytochem.2024.114316","url":null,"abstract":"<div><div>Fourteen benzofuran compounds were identified in the fruits <em>of Psoralea corylifoli</em>a L., with four previously undescribed compounds (<strong>4</strong>, <strong>9</strong>–<strong>11</strong>) being discovered. Their chemical structures were definitively determined through comprehensive spectral data analysis. The compounds were investigated for their antioxidant, anti-tumor, and anti-inflammatory properties, revealing that benzofuran compounds exhibit significant anti-inflammatory effects. Compound <strong>2</strong> demonstrated the most potent anti-inflammatory effect, surpassing that of the positive control drug. The potential anti-inflammatory mechanism of <strong>2</strong> was extensively explored through network pharmacology research. Subsequent validation of the selected targets via Western blot analysis confirmed that <strong>2</strong> exerts its anti-inflammatory effects by activating the TLR4/NF-κB pathway. These findings offer a novel perspective on the development of benzofuran glycoside compounds and Psoralea fructus.</div></div>","PeriodicalId":20170,"journal":{"name":"Phytochemistry","volume":"230 ","pages":"Article 114316"},"PeriodicalIF":3.2,"publicationDate":"2024-11-08","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"142626203","PeriodicalName":null,"FirstCategoryId":null,"ListUrlMain":null,"RegionNum":2,"RegionCategory":"生物学","ArticlePicture":[],"TitleCN":null,"AbstractTextCN":null,"PMCID":"","EPubDate":null,"PubModel":null,"JCR":null,"JCRName":null,"Score":null,"Total":0}
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