Pub Date : 2024-11-07DOI: 10.1016/j.phytochem.2024.114317
Parviz Sukhrobov , Jun Li , Liu Liu , Sodik Numonov , Haji Akber Aisa
Eleven undescribed sesquiterpenes, vachanins A−K covering types of germacrane, eudesmane, guaiacane, and cadinane, along with fifteen known analogs were isolated from the aerial parts of Artemisia vachanica Krasch. ex Poljakov. Their structures were established on the basis of HRMS and NMR data, and their absolute configurations were successfully determined by single-crystal X-ray diffraction analysis, 13C-NMR calculations and DP4+ probability analysis, and ECD data in corporation with quantum chemical calculations. Vachanin A is the first example of germacrane bearing an uncommon C5, C10-oxygen bridge. All isolated compounds were assayed for anti-inflammatory and anti-diabetic activities. Compounds 15 and 22 presented weak anti-inflammatory activity by inhibiting the release of NO in RAW 264.7 cells induced by LPS with IC50 values of 42.82 ± 1.43, and 63.37 ± 3.28 μM.
从蒿属植物Krasch. ex Poljakov的气生部分分离出了11种尚未描述过的倍半萜烯类化合物，即蒿苷A-K，包括germacrane、eudesmane、guaiacane和cadinane等类型，以及15种已知的类似物。根据 HRMS 和 NMR 数据确定了它们的结构，并通过单晶 X 射线衍射分析、13C-NMR 计算和 DP4+ 概率分析以及结合量子化学计算的 ECD 数据成功确定了它们的绝对构型。Vachanin A是第一个带有不常见的C5、C10-氧桥的胚芽鞘氨醇。对所有分离出的化合物进行了抗炎和抗糖尿病活性测定。化合物 15 和 22 通过抑制 LPS 诱导的 RAW 264.7 细胞中 NO 的释放而表现出微弱的抗炎活性，IC50 值分别为 42.82 ± 1.43 和 63.37 ± 3.28 μM。
{"title":"Sesquiterpenes from the aerial parts of Artemisia vachanica krasch. ex poljakov and their anti-inflammatory and anti-diabetic activities","authors":"Parviz Sukhrobov , Jun Li , Liu Liu , Sodik Numonov , Haji Akber Aisa","doi":"10.1016/j.phytochem.2024.114317","DOIUrl":"10.1016/j.phytochem.2024.114317","url":null,"abstract":"<div><div>Eleven undescribed sesquiterpenes, vachanins A−K covering types of germacrane, eudesmane, guaiacane, and cadinane, along with fifteen known analogs were isolated from the aerial parts of <em>Artemisia vachanica</em> Krasch. ex Poljakov. Their structures were established on the basis of HRMS and NMR data, and their absolute configurations were successfully determined by single-crystal X-ray diffraction analysis, <sup>13</sup>C-NMR calculations and DP4+ probability analysis, and ECD data in corporation with quantum chemical calculations. Vachanin A is the first example of germacrane bearing an uncommon C<sub>5</sub>, C<sub>10</sub>-oxygen bridge. All isolated compounds were assayed for anti-inflammatory and anti-diabetic activities. Compounds <strong>15</strong> and <strong>22</strong> presented weak anti-inflammatory activity by inhibiting the release of NO in RAW 264.7 cells induced by LPS with IC<sub>50</sub> values of 42.82 ± 1.43, and 63.37 ± 3.28 <em>μ</em>M.</div></div>","PeriodicalId":20170,"journal":{"name":"Phytochemistry","volume":"230 ","pages":"Article 114317"},"PeriodicalIF":3.2,"publicationDate":"2024-11-07","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"142626204","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 : 2024-11-06DOI: 10.1016/j.phytochem.2024.114315
Mohamed A. Tammam , Nikolaos Tsoureas , Dafni-Ioanna Diakaki , Carlos M. Duarte , Vassilios Roussis , Efstathia Ioannou
Thuwalamides A–E (1, 3, 5, 6 and 8), previously undescribed polychlorinated amides, along with ten previously reported related compounds (2, 4, 7 and 9–15), were isolated from the organic extract of the marine sponge Lamellodysidea herbacea (Keller), collected off the village of Thuwal in the Red Sea at Saudi Arabia. The structures of the isolated compounds have been determined through extensive analysis of their NMR and MS data, while their absolute stereochemistry was unequivocally established via single crystal X-ray diffraction. Additionally, the absolute stereochemistry of the previously reported compounds 2 and 4, whose configuration was not determined, has also been established using single-crystal X-ray crystallographic analysis. The antibacterial activity of compounds 1–15 was evaluated against Escherichia coli and Staphylococcus aureus. Among them, compound 14 displayed activity against S. aureus comparable to vancomycin that was used as a positive control with a MIC value of 4 μg/mL.
从沙特阿拉伯红海 Thuwal 村附近采集的海洋海绵 Lamellodysidea herbacea（Keller）的有机萃取物中分离出了 Thuwalamides A-E（1、3、5、6 和 8），它们是之前未曾描述过的多氯酰胺，以及之前报道过的 10 种相关化合物（2、4、7 和 9-15）。通过对这些分离化合物的核磁共振和质谱数据进行广泛分析，确定了它们的结构，并通过单晶 X 射线衍射明确确定了它们的绝对立体化学结构。此外，先前报告的化合物 2 和 4 的构型尚未确定，其绝对立体化学结构也通过单晶 X 射线晶体分析得以确定。评估了化合物 1-15 对大肠杆菌和金黄色葡萄球菌的抗菌活性。其中，化合物 14 对金黄色葡萄球菌的活性与作为阳性对照的万古霉素相当，其 MIC 值为 4 μg/mL。
{"title":"Thuwalamides A–E: Polychlorinated amides from the marine sponge Lamellodysidea herbacea collected from the Saudi Arabian Red Sea","authors":"Mohamed A. Tammam , Nikolaos Tsoureas , Dafni-Ioanna Diakaki , Carlos M. Duarte , Vassilios Roussis , Efstathia Ioannou","doi":"10.1016/j.phytochem.2024.114315","DOIUrl":"10.1016/j.phytochem.2024.114315","url":null,"abstract":"<div><div>Thuwalamides A–E (<strong>1</strong>, <strong>3</strong>, <strong>5</strong>, <strong>6</strong> and <strong>8</strong>), previously undescribed polychlorinated amides, along with ten previously reported related compounds (<strong>2</strong>, <strong>4</strong>, <strong>7</strong> and <strong>9</strong>–<strong>15</strong>), were isolated from the organic extract of the marine sponge <em>Lamellodysidea herbacea</em> (Keller), collected off the village of Thuwal in the Red Sea at Saudi Arabia. The structures of the isolated compounds have been determined through extensive analysis of their NMR and MS data, while their absolute stereochemistry was unequivocally established via single crystal X-ray diffraction. Additionally, the absolute stereochemistry of the previously reported compounds <strong>2</strong> and <strong>4</strong>, whose configuration was not determined, has also been established using single-crystal X-ray crystallographic analysis. The antibacterial activity of compounds <strong>1</strong>–<strong>15</strong> was evaluated against <em>Escherichia coli</em> and <em>Staphylococcus aureus</em>. Among them, compound <strong>14</strong> displayed activity against <em>S. aureus</em> comparable to vancomycin that was used as a positive control with a MIC value of 4 μg/mL.</div></div>","PeriodicalId":20170,"journal":{"name":"Phytochemistry","volume":"230 ","pages":"Article 114315"},"PeriodicalIF":3.2,"publicationDate":"2024-11-06","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"142626211","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 : 2024-10-24DOI: 10.1016/j.phytochem.2024.114311
Zhengyang Lu , Gui Mei , Fangfang Zhong , Yingzi Gu , Jiahe Xi , Xianghong Chen , Jing Xu , Xianju Huang , Guangzhong Yang , Yu Chen
Seven undescribed iridoids, identified as valeriridoids A-E (compounds 1, 5, 18, 19a, 19b, 20a, and 20b), were isolated from the roots and rhizomes of Valeriana officinalis L., along with sixteen known iridoids and nine known lignans. The structures were elucidated using NMR and MS spectroscopy, and the absolute configurations of the undescribed iridoids were determined through ECD calculations. Valeriridoids D and E were found to be epimeric and scalemic mixtures, which were successfully resolved through a chiral column. These isolated iridoids were evaluated for their antiproliferative activities, with valeriridoid A, jatamanvaltrates P, and Q showing significant effects against human non-small cell lung cancer cells, with IC50 values of 14.68, 8.77, and 10.07 μM, respectively. Furthermore, the antihyperglycemic properties of the compounds were investigated in insulin-resistant human hepatoblastoma cells induced by palmitic acid treatment, revealing that valeriridoid A, jatamanvaltrates P, and Q at a concentration of 10 μM led to a notable increase in glucose consumption.
从 Valeriana officinalis L. 的根和根茎中分离出了七种未被描述的虹彩类化合物（化合物 1、5、18、19a、19b、20a 和 20b），以及十六种已知的虹彩类化合物和九种已知的木脂素。利用核磁共振和质谱法阐明了它们的结构，并通过 ECD 计算确定了未被描述的虹彩类化合物的绝对构型。发现缬烷基环氧乙烷 D 和 E 是外嵌体和鳞片状混合物，并通过手性色谱柱成功地将其分离出来。对这些分离出的虹彩类化合物进行了抗增殖活性评估，其中缬烷基虹彩类化合物 A、鸦胆子缬烷酸酯 P 和 Q 对人类非小细胞肺癌细胞具有显著的抗癌作用，其 IC50 值分别为 14.68、8.77 和 10.07 μM。此外，还研究了这些化合物在棕榈酸处理诱导的胰岛素抗性人肝母细胞瘤细胞中的抗高血糖特性，结果表明，浓度为 10 μM 的缬烷酸 A、鸦胆子缬烷酸 P 和 Q 能明显增加葡萄糖的消耗。
{"title":"Iridoids and lignans from Valeriana officinalis and their bioactivities","authors":"Zhengyang Lu , Gui Mei , Fangfang Zhong , Yingzi Gu , Jiahe Xi , Xianghong Chen , Jing Xu , Xianju Huang , Guangzhong Yang , Yu Chen","doi":"10.1016/j.phytochem.2024.114311","DOIUrl":"10.1016/j.phytochem.2024.114311","url":null,"abstract":"<div><div>Seven undescribed iridoids, identified as valeriridoids A-E (compounds <strong>1</strong>, <strong>5</strong>, <strong>18</strong>, <strong>19a</strong>, <strong>19b</strong>, <strong>20a</strong>, and <strong>20b</strong>), were isolated from the roots and rhizomes of <em>Valeriana officinalis</em> L., along with sixteen known iridoids and nine known lignans. The structures were elucidated using NMR and MS spectroscopy, and the absolute configurations of the undescribed iridoids were determined through ECD calculations. Valeriridoids D and E were found to be epimeric and scalemic mixtures, which were successfully resolved through a chiral column. These isolated iridoids were evaluated for their antiproliferative activities, with valeriridoid A, jatamanvaltrates P, and Q showing significant effects against human non-small cell lung cancer cells, with IC<sub>50</sub> values of 14.68, 8.77, and 10.07 μM, respectively. Furthermore, the antihyperglycemic properties of the compounds were investigated in insulin-resistant human hepatoblastoma cells induced by palmitic acid treatment, revealing that valeriridoid A, jatamanvaltrates P, and Q at a concentration of 10 μM led to a notable increase in glucose consumption.</div></div>","PeriodicalId":20170,"journal":{"name":"Phytochemistry","volume":"229 ","pages":"Article 114311"},"PeriodicalIF":3.2,"publicationDate":"2024-10-24","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"142505940","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}
Euphohelinodes D–I (1–6), six previously unreported ent-abietane lactones, along with two known analogues (7 and 8), were isolated from the anti-inflammatory fraction extracted from E. helioscopia by a bioactivity-guided isolation. Their structures were characterized using a combination of spectroscopic data interpretation, single-crystal X-ray diffraction and ECD analysis. The anti-inflammatory activity of these compounds was evaluated by measuring their inhibitory effects on NO production in LPS-stimulated RAW264.7 macrophages. The most active candidate, euphohelinode H (5), had better inhibitory activity against NO production with an IC50 value of 30.23 ± 2.33 μM. Further study revealed that 5 significantly suppressed the expressions of iNOS and COX-2 through the NF-κB signaling pathway.
通过生物活性指导分离法，从E. helioscopia提取的抗炎馏分中分离出了Euphohelinodes D-I（1-6）、六种以前未报道过的ent-abietane内酯以及两种已知的类似物（7和8）。通过光谱数据解读、单晶 X 射线衍射和 ECD 分析，对它们的结构进行了表征。通过测量这些化合物对 LPS 刺激的 RAW264.7 巨噬细胞产生的 NO 的抑制作用，评估了它们的抗炎活性。活性最高的候选化合物 euphohelinode H（5）对 NO 生成具有较好的抑制活性，其 IC50 值为 30.23 ± 2.33 μM。进一步研究发现，5 通过 NF-κB 信号通路明显抑制了 iNOS 和 COX-2 的表达。
{"title":"ent-Abietane-type lactones with anti-inflammatory activity from Euphorbia helioscopia","authors":"Hong-Ying Yang, Pei-Zhi Huang, Wei-Jiao Feng, Pei-Wei Si, Kun Gao, Jian-Jun Chen","doi":"10.1016/j.phytochem.2024.114313","DOIUrl":"10.1016/j.phytochem.2024.114313","url":null,"abstract":"<div><div>Euphohelinodes D–I (<strong>1</strong>–<strong>6</strong>), six previously unreported <em>ent-</em>abietane lactones, along with two known analogues (<strong>7</strong> and <strong>8</strong>), were isolated from the anti-inflammatory fraction extracted from <em>E. helioscopia</em> by a bioactivity-guided isolation. Their structures were characterized using a combination of spectroscopic data interpretation, single-crystal X-ray diffraction and ECD analysis. The anti-inflammatory activity of these compounds was evaluated by measuring their inhibitory effects on NO production in LPS-stimulated RAW264.7 macrophages. The most active candidate, euphohelinode H (<strong>5</strong>), had better inhibitory activity against NO production with an IC<sub>50</sub> value of 30.23 ± 2.33 <em>μ</em>M. Further study revealed that <strong>5</strong> significantly suppressed the expressions of iNOS and COX-2 through the NF-<em>κ</em>B signaling pathway.</div></div>","PeriodicalId":20170,"journal":{"name":"Phytochemistry","volume":"229 ","pages":"Article 114313"},"PeriodicalIF":3.2,"publicationDate":"2024-10-24","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"142505939","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 : 2024-10-24DOI: 10.1016/j.phytochem.2024.114310
Ding Luo , Qian Xie , He Tian , Xin-Kai Zheng , Jia-Wen Zou , Yue-Hao Huang , Yan-Jun Chen , Chun-Lin Fan , Li-Jun Hu , Jian-Xin Chen , Hao Wang , Guo-Cai Wang , Yu-Bo Zhang
The four matrine-derived alkaloids, namely sophflarines B−E (1−4), with distinct skeleton types, were isolated from Sophora flavescens. Compounds 1 and 2 possess rare 1-aza-11-oxatricyclo[5.3.1.02,6] undecane cores, featuring unprecedented N,O-heterocyclic systems of 5/5/6/6/6 and 6/5/5/6/6, respectively. Compounds 3 and 4 exhibit two novel C15 units with tetracyclic skeletons of 5/6/6/6 and 6/5/6/6, respectively. The structures were elucidated through spectroscopic analyses, quantum chemical calculations, and X-ray diffraction data. A plausible biosynthetic pathway for these newly discovered compounds was proposed. Furthermore, compounds 1 and 2 showed anti-neuroinflammatory activity against the cytokines NO, TNF-α, and IL-6. Compound 2 exhibited a neuroprotective effect potentially mediated by activating the Keap1-Nrf2/HO-1 pathway to reduce inflammation and oxidative stress.
{"title":"Sophflarines B−E, four distinctive matrine alkaloids from Sophora flavescens with potential neuroprotective activities","authors":"Ding Luo , Qian Xie , He Tian , Xin-Kai Zheng , Jia-Wen Zou , Yue-Hao Huang , Yan-Jun Chen , Chun-Lin Fan , Li-Jun Hu , Jian-Xin Chen , Hao Wang , Guo-Cai Wang , Yu-Bo Zhang","doi":"10.1016/j.phytochem.2024.114310","DOIUrl":"10.1016/j.phytochem.2024.114310","url":null,"abstract":"<div><div>The four matrine-derived alkaloids, namely sophflarines B−E (<strong>1−4</strong>), with distinct skeleton types, were isolated from <em>Sophora flavescens</em>. Compounds <strong>1</strong> and <strong>2</strong> possess rare 1-aza-11-oxatricyclo[5.3.1.0<sup>2,6</sup>] undecane cores, featuring unprecedented N,O-heterocyclic systems of 5/5/6/6/6 and 6/5/5/6/6, respectively. Compounds <strong>3</strong> and <strong>4</strong> exhibit two novel C<sub>15</sub> units with tetracyclic skeletons of 5/6/6/6 and 6/5/6/6, respectively. The structures were elucidated through spectroscopic analyses, quantum chemical calculations, and X-ray diffraction data. A plausible biosynthetic pathway for these newly discovered compounds was proposed. Furthermore, compounds <strong>1</strong> and <strong>2</strong> showed anti-neuroinflammatory activity against the cytokines NO, TNF-α, and IL-6. Compound <strong>2</strong> exhibited a neuroprotective effect potentially mediated by activating the Keap1-Nrf2/HO-1 pathway to reduce inflammation and oxidative stress.</div></div>","PeriodicalId":20170,"journal":{"name":"Phytochemistry","volume":"229 ","pages":"Article 114310"},"PeriodicalIF":3.2,"publicationDate":"2024-10-24","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"142505943","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 : 2024-10-24DOI: 10.1016/j.phytochem.2024.114306
Li-Li Shao , Kai-Qin Lin , Han-Fei Liu , Zhi-Yao Li , Ni Zhang , Chao Chen , Wei-Dong Pan , Hua-Yong Lou , Jin-Yu Li
{"title":"Corrigendum to “Meliasanines A–L, tirucallane-type triterpenoids from Melia toosendan with anti-inflammatory properties via NF-κB signaling pathway” [Phytochemistry 225 (2024) 114192]>","authors":"Li-Li Shao , Kai-Qin Lin , Han-Fei Liu , Zhi-Yao Li , Ni Zhang , Chao Chen , Wei-Dong Pan , Hua-Yong Lou , Jin-Yu Li","doi":"10.1016/j.phytochem.2024.114306","DOIUrl":"10.1016/j.phytochem.2024.114306","url":null,"abstract":"","PeriodicalId":20170,"journal":{"name":"Phytochemistry","volume":"229 ","pages":"Article 114306"},"PeriodicalIF":3.2,"publicationDate":"2024-10-24","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"142505944","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 : 2024-10-22DOI: 10.1016/j.phytochem.2024.114312
Jun Gu Kim , Jae Sang Han , Yong Beom Cho , Beom Kyun An , Dongho Lee , Mi Kyeong Lee , Bang Yeon Hwang
Seven previously undescribed dihydro-β-agarofurans (1–7) together with 28 known compounds were isolated from Celastrus orbiculatus fruits using LC-MS/MS-based molecular networking-guided purification. Their structures were elucidated through 1D and 2D-NMR, HRESIMS analysis, and ECD quantum chemical calculations. The inhibitory effects of all isolated compounds on α-MSH-induced melanin production in B16F0 melanoma cells were tested. Compounds 1, 11, 12, 19–21, 23, 29, 31, 34, and 35 showed significant inhibitory effects on melanin production with IC50 values ranging from 11.3 to 30.1 μM.
{"title":"Molecular networking-guided isolation of melanogenesis inhibitory dihydro-β-agarofuran sesquiterpenoids from Celastrus orbiculatus","authors":"Jun Gu Kim , Jae Sang Han , Yong Beom Cho , Beom Kyun An , Dongho Lee , Mi Kyeong Lee , Bang Yeon Hwang","doi":"10.1016/j.phytochem.2024.114312","DOIUrl":"10.1016/j.phytochem.2024.114312","url":null,"abstract":"<div><div>Seven previously undescribed dihydro-<em>β</em>-agarofurans (<strong>1</strong>–<strong>7</strong>) together with 28 known compounds were isolated from <em>Celastrus orbiculatus</em> fruits using LC-MS/MS-based molecular networking-guided purification. Their structures were elucidated through 1D and 2D-NMR, HRESIMS analysis, and ECD quantum chemical calculations. The inhibitory effects of all isolated compounds on <em>α</em>-MSH-induced melanin production in B16F0 melanoma cells were tested. Compounds <strong>1</strong>, <strong>11</strong>, <strong>12</strong>, <strong>19</strong>–<strong>21</strong>, <strong>23</strong>, <strong>29</strong>, <strong>31</strong>, <strong>34</strong>, and <strong>35</strong> showed significant inhibitory effects on melanin production with IC<sub>50</sub> values ranging from 11.3 to 30.1 μM.</div></div>","PeriodicalId":20170,"journal":{"name":"Phytochemistry","volume":"229 ","pages":"Article 114312"},"PeriodicalIF":3.2,"publicationDate":"2024-10-22","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"142505941","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 : 2024-10-22DOI: 10.1016/j.phytochem.2024.114314
Fang-Lu Wei , Hui Liu , Shu-Han Zhang , Jiao-Xian Du , Tao Feng , Juan He
Chemical investigation on the rice fermentation of the fungus Physisporinus vitreus led to the isolation of ten previously undescribed lanostane triterpenoids, physivitrins I–R, and three known analogues. The new structures were elucidated on the basis of extensive spectroscopic methods, including 1D & 2D NMR, HRESIMS, UV and ECD. Physivitrins I and P exhibited significant inhibitory activities against NO production in LPS-activated RAW267.4 macrophages with IC50 values of 8.2 and 11.5 μM, respectively. The comprehensive data indicated that P. vitreus is rich in lanostane triterpenes and has potential anti-inflammatory application prospects.
通过对真菌 Physisporinus vitreus 的水稻发酵进行化学研究，分离出了 10 种以前未曾描述过的羊角甾烷三萜类化合物 Physivitrins I-R 和 3 种已知的类似物。这些新结构是在广泛的光谱方法（包括一维和二维核磁共振、HRESIMS、紫外光谱和电离辐射光谱）基础上阐明的。Physivitrins I 和 P 对 LPS 激活的 RAW267.4 巨噬细胞产生的 NO 具有显著的抑制活性，IC50 值分别为 8.2 和 11.5 μM。综合数据表明，玻璃酸浆富含羊毛甾烷三萜类化合物，具有潜在的抗炎应用前景。
{"title":"Physivitrins I–R, lanostane triterpenoids with anti-inflammatory activities from the fungus Physisporinus vitreus","authors":"Fang-Lu Wei , Hui Liu , Shu-Han Zhang , Jiao-Xian Du , Tao Feng , Juan He","doi":"10.1016/j.phytochem.2024.114314","DOIUrl":"10.1016/j.phytochem.2024.114314","url":null,"abstract":"<div><div>Chemical investigation on the rice fermentation of the fungus <em>Physisporinus vitreus</em> led to the isolation of ten previously undescribed lanostane triterpenoids, physivitrins I–R, and three known analogues. The new structures were elucidated on the basis of extensive spectroscopic methods, including 1D & 2D NMR, HRESIMS, UV and ECD. Physivitrins I and P exhibited significant inhibitory activities against NO production in LPS-activated RAW267.4 macrophages with IC<sub>50</sub> values of 8.2 and 11.5 μM, respectively. The comprehensive data indicated that <em>P</em>. <em>vitreus</em> is rich in lanostane triterpenes and has potential anti-inflammatory application prospects.</div></div>","PeriodicalId":20170,"journal":{"name":"Phytochemistry","volume":"229 ","pages":"Article 114314"},"PeriodicalIF":3.2,"publicationDate":"2024-10-22","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"142505945","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 : 2024-10-22DOI: 10.1016/j.phytochem.2024.114307
Shu-Lan Liu , Xue-Ling Huang , Shun-Hua Zhong , Yong-Hui Ma , Feng Wei , Yu-Ye Zhang , Jin Li , Ke-Jian Pang , Ping Zhao , Xin-Zhou Yang
Seven unreported compounds were isolated from dried flower buds of Ochrocarpus longifolius in this study, including an alkaloid ochrocaracid A (1), five coumarins ochrocarpins I (2), J (3), K (4), L (5), and M (6), and one styryl-2-pyranone compound iresinoacid (7) and nine known compounds (8–16). All these compounds were found in O. longifolius for the first time. Their structural elucidation was achieved through NMR, HR-ESI-MS, and ECD data. Additionally, a glucose uptake-promoting activity assay revealed that compounds 10 (128.21 μM) and 16 (123.15 μM) increased the glucose uptake capacity of L6 cells by 1.49-fold and 1.48-fold, respectively. These bioactive compounds could be potential candidates for further pharmaceutical applications.
本研究从 Ochrocarpus longifolius 的干燥花蕾中分离出了七种未报道的化合物，包括一种生物碱 ochrocaracid A (1)，五种香豆素 ochrocarpins I (2)、J (3)、K (4)、L (5) 和 M (6)，一种苯乙烯基-2-吡喃酮化合物 iresinoacid (7) 以及九种已知化合物 (8-16)。所有这些化合物都是首次在 O. longifolius 中发现。通过 NMR、HR-ESI-MS 和 ECD 数据，这些化合物的结构得以阐明。此外，葡萄糖摄取促进活性测定显示，化合物 10（128.21 μM）和 16（123.15 μM）分别将 L6 细胞的葡萄糖摄取能力提高了 1.49 倍和 1.48 倍。这些生物活性化合物可能成为进一步的药物应用候选化合物。
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Pub Date : 2024-10-19DOI: 10.1016/j.phytochem.2024.114308
Warsan Nora Mohamed , Hussain Shakeel Butt , Thomas J. Schmidt , Andrea Angelov Eltvik , Desheng Wu , Karl Egil Malterud , Marit Inngjerdingen , Kari Tvete Inngjerdingen , Helle Wangensteen
Daphne mezereum L. (Thymelaeaceae) was an important medicinal plant in Norway during the 18th and 19th centuries and used against diseases such as diarrhea, swelling, stomach pain, and tuberculosis. Five previously undescribed phenolic compounds, including two biflavonoids with a catechin core structure, two tricoumarins, and one bicoumarin, together with ten known compounds were isolated from a 50% EtOH extract of the bark of D. mezereum. Using NMR, HRESIMS, acid hydrolysis, and circular dichroism spectra, the biflavonoids were identified as 3′-hydroxygenkwanol A and 3′-hydroxydihydrodaphnodorin B, and the coumarins were identified as 3‴-O-acetyltriumbellin, triumbellin 4‴-O-β-d-glucopyranoside, and daphnogitin-7-O-β-d-glucopyranoside. The absolute configuration of dihydrodaphnodorin B was for the first time established as 2R, 3S, 2″S, 3″S. Daphnin, syringin, 3′-hydroxydihydrodaphnodorin B, dihydrodaphnodorin B, and neochamaejasmin A and B were identified as the major secondary metabolites in the extract. Neochamaejasmin A and B showed the most potent inhibition of TNF-α secretion in Con A stimulated peripheral blood mononuclear cells (PBMCs) with 71.3 ± 3.4 and 83.5 ± 11.5% inhibition, respectively, at 50 μM.
Daphne mezereum L.（百里香科）在十八和十九世纪是挪威的一种重要药用植物，可用于治疗腹泻、浮肿、胃痛和肺结核等疾病。从 D. mezereum 树皮的 50% EtOH 提取物中分离出了五种以前未曾描述过的酚类化合物，包括两种具有儿茶素核心结构的双黄酮类化合物、两种三香豆素类化合物和一种双香豆素类化合物，以及十种已知化合物。利用核磁共振、HRESIMS、酸水解和圆二色光谱，双黄酮被鉴定为 3'-hydroxygenkwanol A 和 3'-hydroxydihydrodaphnodorin B，香豆素被鉴定为 3'''-O-acetyltriumbellin, triumbellin 4'''-O-β-D-glucopyranoside 和 daphnogitin-7-O-β-D-glucopyranoside 。首次确定了二氢萘啶 B 的绝对构型为 2R、3S、2''S、3''S。经鉴定，提取物中的主要次生代谢物为水飞蓟素、丁香素、3'-羟基二氢水飞蓟素 B、二氢水飞蓟素 B、新矢车菊素 A 和 B。新蛇床子素 A 和 B 对 Con A 刺激的外周血单核细胞（PBMCs）分泌 TNF-α 的抑制作用最强，在 50 μM 时的抑制率分别为 71.3 ± 3.4% 和 83.5 ± 11.5%。
{"title":"Biflavonoids and bi- and tricoumarins from Daphne mezereum and inhibition of TNF-α secretion","authors":"Warsan Nora Mohamed , Hussain Shakeel Butt , Thomas J. Schmidt , Andrea Angelov Eltvik , Desheng Wu , Karl Egil Malterud , Marit Inngjerdingen , Kari Tvete Inngjerdingen , Helle Wangensteen","doi":"10.1016/j.phytochem.2024.114308","DOIUrl":"10.1016/j.phytochem.2024.114308","url":null,"abstract":"<div><div><em>Daphne mezereum</em> L. (Thymelaeaceae) was an important medicinal plant in Norway during the 18th and 19th centuries and used against diseases such as diarrhea, swelling, stomach pain, and tuberculosis. Five previously undescribed phenolic compounds, including two biflavonoids with a catechin core structure, two tricoumarins, and one bicoumarin, together with ten known compounds were isolated from a 50% EtOH extract of the bark of <em>D</em>. <em>mezereum</em>. Using NMR, HRESIMS, acid hydrolysis, and circular dichroism spectra, the biflavonoids were identified as 3′-hydroxygenkwanol A and 3′-hydroxydihydrodaphnodorin B, and the coumarins were identified as 3‴-<em>O</em>-acetyltriumbellin, triumbellin 4‴-<em>O</em>-β-<span>d</span>-glucopyranoside, and daphnogitin-7-<em>O</em>-β-<span>d</span>-glucopyranoside. The absolute configuration of dihydrodaphnodorin B was for the first time established as 2R, 3S, 2″S, 3″S. Daphnin, syringin, 3′-hydroxydihydrodaphnodorin B, dihydrodaphnodorin B, and neochamaejasmin A and B were identified as the major secondary metabolites in the extract. Neochamaejasmin A and B showed the most potent inhibition of TNF-α secretion in Con A stimulated peripheral blood mononuclear cells (PBMCs) with 71.3 ± 3.4 and 83.5 ± 11.5% inhibition, respectively, at 50 μM.</div></div>","PeriodicalId":20170,"journal":{"name":"Phytochemistry","volume":"229 ","pages":"Article 114308"},"PeriodicalIF":3.2,"publicationDate":"2024-10-19","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"142472498","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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