Pub Date : 2025-02-06DOI: 10.1016/j.phytochem.2025.114423
Yao-Yao Zheng, Guang-Shan Yao, Jiao-Jiao Li, Na Han, Jun-Qiu Mao, Ya-Hui Zhang, Ling Lv, Yang Liu, Chang-Yun Wang
The chemical investigation of the marine sediment-derived fungus Aspergillus terreus PPS1 led to the isolation and identification of seven previously undescribed secondary metabolites, including three alkaloids, asperspiroids A, B (1, 2) and astepyrazinol C (3), two lumazine peptides, terrelumamides C, D (5, 6), and two polyketides, scytalols E, F (8, 9), together with two known compounds. The structures of these undescribed compounds were elucidated by comprehensive spectroscopic analysis of NMR and HRESIMS data, and the absolute configurations were determined using ECD calculations, modified Mosher's method, and Marfey's analysis. Notably, asperspiroids A, B (1, 2) were uncommon alkaloids characterized by a rare 6/5/6 indole spirocyclolactone structure found naturally. The isolated compounds were assessed for their potential antibacterial, cytotoxic and anti-inflammatory activities. Astepyrazinol C (3) and its analog astepyrazinol B (4) demonstrated significant inhibition activity against LPS-induced NO production in RAW264.7 macrophages, with inhibition rates of 37.4% and 64.6%, respectively, at a concentration of 20 μM.
{"title":"Undescribed alkaloids, peptides and polyketides from marine sediment-derived fungus Aspergillus terreus PPS1.","authors":"Yao-Yao Zheng, Guang-Shan Yao, Jiao-Jiao Li, Na Han, Jun-Qiu Mao, Ya-Hui Zhang, Ling Lv, Yang Liu, Chang-Yun Wang","doi":"10.1016/j.phytochem.2025.114423","DOIUrl":"https://doi.org/10.1016/j.phytochem.2025.114423","url":null,"abstract":"<p><p>The chemical investigation of the marine sediment-derived fungus Aspergillus terreus PPS1 led to the isolation and identification of seven previously undescribed secondary metabolites, including three alkaloids, asperspiroids A, B (1, 2) and astepyrazinol C (3), two lumazine peptides, terrelumamides C, D (5, 6), and two polyketides, scytalols E, F (8, 9), together with two known compounds. The structures of these undescribed compounds were elucidated by comprehensive spectroscopic analysis of NMR and HRESIMS data, and the absolute configurations were determined using ECD calculations, modified Mosher's method, and Marfey's analysis. Notably, asperspiroids A, B (1, 2) were uncommon alkaloids characterized by a rare 6/5/6 indole spirocyclolactone structure found naturally. The isolated compounds were assessed for their potential antibacterial, cytotoxic and anti-inflammatory activities. Astepyrazinol C (3) and its analog astepyrazinol B (4) demonstrated significant inhibition activity against LPS-induced NO production in RAW264.7 macrophages, with inhibition rates of 37.4% and 64.6%, respectively, at a concentration of 20 μM.</p>","PeriodicalId":20170,"journal":{"name":"Phytochemistry","volume":" ","pages":"114423"},"PeriodicalIF":3.2,"publicationDate":"2025-02-06","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"143374640","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 : 2025-01-30DOI: 10.1016/j.phytochem.2025.114418
Ahmed F. Essa , Mai M. Elghonemy , Rehab F. Taher , Rasha M. Allam , Abdelsamed I. Elshamy
As part of efforts to identify natural modulators of multi-drug-resistant breast cancer, Euphorbia mauritanica L. chloroform extract yielded four undescribed oxygenated diterpenes, including three nor-ent-abietanes, euphomauritanol C-E (1–3), and one polyacylated jatrophane, euphomauritanolide A (4), along with two knowns, helioscopinolide A (5) and enukokurin (6). The chemical structures and configurations of compounds were established by combination of HRMS, FTIR, and NMR spectroscopic tools along with experimental and calculated TDDFT-ECD. The cytotoxicity evaluation of isolated compounds against the MCF-7ADR revealed 4 and 2 are the most potent with IC50 values of 3.2 ± 0.58 and 4.67 ± 0.29 μM, respectively. Co-administration of compounds 4 and 2 with DOX improved its cytotoxic effect, with a combination index value of 0.41 for 4, indicating a synergistic effect. Mechanistically, 4 modulated DOX anticancer properties via potentiating DOX-induced Go/G1 cell cycle arrest rather than G2M arrest of DOX alone and shifting the cell death of DOX to be mainly apoptotic cell death. Furthermore, 4 alone and combined with DOX showed promising anti-migratory effects against MCF-7ADR. In conclusion, 4 showed promising co-chemotherapeutic effects to the DOX against MCF-7ADR, indicating that this compound possesses potential as an auspicious lead chemical to target breast cancer cells resistant to doxorubicin.
{"title":"Undescribed diterpenes from Euphorbia mauritanica L. as modulators of the breast cancer resistance: Mechanistic and in silico studies","authors":"Ahmed F. Essa , Mai M. Elghonemy , Rehab F. Taher , Rasha M. Allam , Abdelsamed I. Elshamy","doi":"10.1016/j.phytochem.2025.114418","DOIUrl":"10.1016/j.phytochem.2025.114418","url":null,"abstract":"<div><div>As part of efforts to identify natural modulators of multi-drug-resistant breast cancer, <em>Euphorbia mauritanica</em> L. chloroform extract yielded four undescribed oxygenated diterpenes, including three nor-<em>ent</em>-abietanes, euphomauritanol C-E (<strong>1–3</strong>), and one polyacylated jatrophane, euphomauritanolide A (<strong>4</strong>), along with two knowns, helioscopinolide A (<strong>5</strong>) and enukokurin (<strong>6</strong>). The chemical structures and configurations of compounds were established by combination of HRMS, FTIR, and NMR spectroscopic tools along with experimental and calculated TDDFT-ECD. The cytotoxicity evaluation of isolated compounds against the MCF-7<sup>ADR</sup> revealed <strong>4</strong> and <strong>2</strong> are the most potent with IC<sub>50</sub> values of 3.2 ± 0.58 and 4.67 ± 0.29 μM, respectively<strong>.</strong> Co-administration of compounds <strong>4</strong> and <strong>2</strong> with DOX improved its cytotoxic effect, with a combination index value of 0.41 for <strong>4</strong>, indicating a synergistic effect. Mechanistically, <strong>4</strong> modulated DOX anticancer properties via potentiating DOX-induced Go/G1 cell cycle arrest rather than G2M arrest of DOX alone and shifting the cell death of DOX to be mainly apoptotic cell death. Furthermore, <strong>4</strong> alone and combined with DOX showed promising anti-migratory effects against MCF-7<sup>ADR</sup>. In conclusion, <strong>4</strong> showed promising co-chemotherapeutic effects to the DOX against MCF-7<sup>ADR</sup>, indicating that this compound possesses potential as an auspicious lead chemical to target breast cancer cells resistant to doxorubicin.</div></div>","PeriodicalId":20170,"journal":{"name":"Phytochemistry","volume":"234 ","pages":"Article 114418"},"PeriodicalIF":3.2,"publicationDate":"2025-01-30","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"143075056","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 : 2025-01-30DOI: 10.1016/j.phytochem.2025.114422
Siyu Qin , Jianbing Tan , Yuting Zheng , Shujuan Zhu , Bin Jiang , Chen Chen , Linjie Wei , Xuanxuan Weng , Zhenxing Zou
A comprehensive chemical investigation of the EtOAc extract derived from the dried branches and leaves of Phyllanthus franchetianus H. Lév had successfully resulted to the isolation of six undescribed cleistanthane diterpenoids phyllanfranins A-F (1–6), along with three known compounds phyllarheophol C (7), phyacioid C (8), and spruceanol (9). The chemical structures of these compounds were elucidated by combined means of HRESIMS, 1D and 2D NMR spectra, together with ECD calculations. The absolute configuration of phyllanfranin A (1) was established by single crystal X-ray diffraction analysis. Notably, phyllanfranin F (6) represents the first ent-cleistanthane diterpenoid with the unique 6/6/6/6 tetracyclic system occurring in nature. Additionally, all the isolates were evaluated for anti-inflammatory activities. As a result, compounds 4 and 8 showed notable inhibitory activity against NO production in LPS-stimulated macrophages RAW264.7 cells, with IC50 values of 19.03 and 18.14 μM, respectively.
{"title":"Phyllanfranins A-F, anti-inflammatory ent-cleistanthane diterpenoids from Phyllanthus franchetianus","authors":"Siyu Qin , Jianbing Tan , Yuting Zheng , Shujuan Zhu , Bin Jiang , Chen Chen , Linjie Wei , Xuanxuan Weng , Zhenxing Zou","doi":"10.1016/j.phytochem.2025.114422","DOIUrl":"10.1016/j.phytochem.2025.114422","url":null,"abstract":"<div><div>A comprehensive chemical investigation of the EtOAc extract derived from the dried branches and leaves of <em>Phyllanthus franchetianus</em> H. Lév had successfully resulted to the isolation of six undescribed cleistanthane diterpenoids phyllanfranins A-F (<strong>1</strong>–<strong>6</strong>), along with three known compounds phyllarheophol C (<strong>7</strong>), phyacioid C (<strong>8</strong>), and spruceanol (<strong>9</strong>). The chemical structures of these compounds were elucidated by combined means of HRESIMS, 1D and 2D NMR spectra, together with ECD calculations. The absolute configuration of phyllanfranin A (<strong>1</strong>) was established by single crystal X-ray diffraction analysis. Notably, phyllanfranin F (<strong>6</strong>) represents the first <em>ent</em>-cleistanthane diterpenoid with the unique 6/6/6/6 tetracyclic system occurring in nature. Additionally, all the isolates were evaluated for anti-inflammatory activities. As a result, compounds <strong>4</strong> and <strong>8</strong> showed notable inhibitory activity against NO production in LPS-stimulated macrophages RAW264.7 cells, with IC<sub>50</sub> values of 19.03 and 18.14 μM, respectively.</div></div>","PeriodicalId":20170,"journal":{"name":"Phytochemistry","volume":"234 ","pages":"Article 114422"},"PeriodicalIF":3.2,"publicationDate":"2025-01-30","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"143075034","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 : 2025-01-30DOI: 10.1016/j.phytochem.2025.114421
Lihang Niu , Jiahang Li , Qiang Zhang , Haoxuan Jin , Chunfeng Xie , Cheng Yang
Nine previously undescribed polyoxygenated cyclohexenes uvacalols L–T (1–9), together with five known analogues (10–14) were obtained from the stems of Uvaria calamistrata. Their structures were established through spectroscopic data analysis, circular dichroism calculations and single-crystal X-ray diffraction. Uvacalols L–N (1–3) are chlorinated analogues. Some compounds were measured for their anti-inflammatory activities through NO generation inhibition in RAW 264.7 cells. Compound 8 had the best inhibitory activity with an IC50 value of 4.49 ± 0.38 μM.
{"title":"Polyoxygenated cyclohexenes from the stems of Uvaria calamistrata","authors":"Lihang Niu , Jiahang Li , Qiang Zhang , Haoxuan Jin , Chunfeng Xie , Cheng Yang","doi":"10.1016/j.phytochem.2025.114421","DOIUrl":"10.1016/j.phytochem.2025.114421","url":null,"abstract":"<div><div>Nine previously undescribed polyoxygenated cyclohexenes uvacalols L–T (<strong>1</strong>–<strong>9</strong>), together with five known analogues (<strong>10</strong>–<strong>14</strong>) were obtained from the stems of <em>Uvaria calamistrata</em>. Their structures were established through spectroscopic data analysis, circular dichroism calculations and single-crystal X-ray diffraction. Uvacalols L–N (<strong>1</strong>–<strong>3</strong>) are chlorinated analogues. Some compounds were measured for their anti-inflammatory activities through NO generation inhibition in RAW 264.7 cells. Compound <strong>8</strong> had the best inhibitory activity with an IC<sub>50</sub> value of 4.49 ± 0.38 μM.</div></div>","PeriodicalId":20170,"journal":{"name":"Phytochemistry","volume":"234 ","pages":"Article 114421"},"PeriodicalIF":3.2,"publicationDate":"2025-01-30","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"143075046","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 : 2025-01-30DOI: 10.1016/j.phytochem.2025.114420
Hau Thi Hong Bui , Ajay Uprety , Trung Huy Ngo , Yun-Seo Kil , Punam Thapa , Jongseo Mo , Hyukjae Choi , Soo Young Kim , Joo-Won Nam
Japanese dodder (Cuscuta japonica Choisy) is a parasitic plant with diverse pharmaceutical properties that has demonstrated great promise for the development of dietary supplements and herbal medicines. A systematic phytochemical investigation of dodder seeds yielded 12 previously undescribed aromatic glycosides (1−12) and eight known constituents (13−20) from various groups, including phenolics, flavonoids, and lignan glycosides. Compound structures were determined using a combination of high-resolution electrospray ionization mass spectrometry and nuclear magnetic resonance (NMR) spectroscopy. Moreover, quantum mechanics-driven 1H iterative full spin analysis revealed intricate NMR spectral details for the isolated glycosides, including multiplicities and coupling constants that were previously ambiguous, providing crucial insight into the presence of higher-order resonance effects in the sugar units as well as long-range couplings in unsaturated molecules. Furthermore, the abilities of the plant extract as well as compounds 1, 2, 4–7, 10, 11, and 14–20 to restore cell viability and reduce reactive oxygen species production in SH-SY5Y cells suggest that C. japonica and its isolates are potential antioxidant neuroprotective therapeutic candidates.
{"title":"Quantum mechanics-based structural analysis of phenolic glycosides from Cuscuta japonica seeds with protective effects against H2O2-induced oxidative stress in SH-SY5Y cells","authors":"Hau Thi Hong Bui , Ajay Uprety , Trung Huy Ngo , Yun-Seo Kil , Punam Thapa , Jongseo Mo , Hyukjae Choi , Soo Young Kim , Joo-Won Nam","doi":"10.1016/j.phytochem.2025.114420","DOIUrl":"10.1016/j.phytochem.2025.114420","url":null,"abstract":"<div><div>Japanese dodder (<em>Cuscuta japonica</em> Choisy) is a parasitic plant with diverse pharmaceutical properties that has demonstrated great promise for the development of dietary supplements and herbal medicines. A systematic phytochemical investigation of dodder seeds yielded 12 previously undescribed aromatic glycosides (<strong>1</strong>−<strong>12</strong>) and eight known constituents (<strong>13</strong>−<strong>20</strong>) from various groups, including phenolics, flavonoids, and lignan glycosides. Compound structures were determined using a combination of high-resolution electrospray ionization mass spectrometry and nuclear magnetic resonance (NMR) spectroscopy. Moreover, quantum mechanics-driven <sup>1</sup>H iterative full spin analysis revealed intricate NMR spectral details for the isolated glycosides, including multiplicities and coupling constants that were previously ambiguous, providing crucial insight into the presence of higher-order resonance effects in the sugar units as well as long-range couplings in unsaturated molecules. Furthermore, the abilities of the plant extract as well as compounds <strong>1</strong>, <strong>2</strong>, <strong>4</strong>–<strong>7</strong>, <strong>10</strong>, <strong>11</strong>, and <strong>14</strong>–<strong>20</strong> to restore cell viability and reduce reactive oxygen species production in SH-SY5Y cells suggest that <em>C. japonica</em> and its isolates are potential antioxidant neuroprotective therapeutic candidates.</div></div>","PeriodicalId":20170,"journal":{"name":"Phytochemistry","volume":"234 ","pages":"Article 114420"},"PeriodicalIF":3.2,"publicationDate":"2025-01-30","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"143075049","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 : 2025-01-30DOI: 10.1016/j.phytochem.2025.114419
Oybek Abdullajanov , Adkham Ganiev , Ablajan Turak , Nurmirza Begmatov , Khayrulla Bobakulov , Jiangyu Zhao , Bo Zhao , Nasrulla Abdullaev , Fei He , Haji Akber Aisa
This experiment focused on investigating the chemical constituents of the plant Artemisia porrecta Krasch.ex Poljakov, resulting in the isolation and characterization of twenty-seven sesquiterpene lactones belonging to the eudesmanolides, germacronolides, melampolides, and heliangolide types. These compounds include ten undescribed sesquiterpene lactones, Porrectolide A-I, 11-epi-Deacetylherbolide D and seventeen known ones. All known compounds were isolated from this plant for the first time. Their structures were established by 1D, 2D NMR spectroscopic and HR-ESI-MS data, electronic circular dichroism, and single crystal X-ray diffraction analysis. Evaluations of the anti-inflammatory activity revealed that 6 had moderate anti-inflammatory activity on lipopolysaccharide-induced nitric oxide production in RAW264.7 cells with the IC50 value of 14.57 ± 0.24 μM.
{"title":"Sesquiterpene lactones from Artemisia porrecta Krasch.ex Poljakov and their anti-inflammatory, cytotoxic and anti-vitiligo activities","authors":"Oybek Abdullajanov , Adkham Ganiev , Ablajan Turak , Nurmirza Begmatov , Khayrulla Bobakulov , Jiangyu Zhao , Bo Zhao , Nasrulla Abdullaev , Fei He , Haji Akber Aisa","doi":"10.1016/j.phytochem.2025.114419","DOIUrl":"10.1016/j.phytochem.2025.114419","url":null,"abstract":"<div><div>This experiment focused on investigating the chemical constituents of the plant <em>Artemisia porrecta</em> Krasch.ex Poljakov, resulting in the isolation and characterization of twenty-seven sesquiterpene lactones belonging to the eudesmanolides, germacronolides, melampolides, and heliangolide types. These compounds include ten undescribed sesquiterpene lactones, Porrectolide A-I, 11-<em>epi</em>-Deacetylherbolide D and seventeen known ones. All known compounds were isolated from this plant for the first time. Their structures were established by 1D, 2D NMR spectroscopic and HR-ESI-MS data, electronic circular dichroism, and single crystal X-ray diffraction analysis. Evaluations of the anti-inflammatory activity revealed that <strong>6</strong> had moderate anti-inflammatory activity on lipopolysaccharide-induced nitric oxide production in RAW264.7 cells with the IC<sub>50</sub> value of 14.57 ± 0.24 μM.</div></div>","PeriodicalId":20170,"journal":{"name":"Phytochemistry","volume":"234 ","pages":"Article 114419"},"PeriodicalIF":3.2,"publicationDate":"2025-01-30","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"143075053","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 : 2025-01-29DOI: 10.1016/j.phytochem.2025.114415
Gang-Zhong Zhou , Ruo-Xi Hu , Qi-Jing Fan , Chu-Chu Xi , Yan-Gang Cao , Jia-Rui Li , Zheng-Yu Cao , Chun-Lei Zhang
Eleven previously undescribed coumarin derivatives, bonenncarpas A–K (1–11), along with three known analogues (12–14), were isolated from the whole plant of Boenninghausenia sessilicarpa. The structures of these compounds were elucidated through comprehensive spectroscopic and spectrometric analyses. Their absolute configurations were determined by comparing experimental and calculated electronic circular dichroism data, as well as by X-ray crystallography. Notably, compound 1 features an open-ring coumarin structure with a five-membered lactone ring, while compounds 9–11 are characterized by a dihydrofuran ring at C-3 and C-4. All compounds were evaluated for their inhibitory effects on lipopolysaccharide-induced nitric oxide production in RAW 264.7 macrophage cells. At a concentration of 10 μM, compounds (−)-3, (+)-5, (+)-6, (+)-9, (−)-9, (+)-10, and (−)-10 exhibited inhibition of NO production, ranging from 25.5% to 95.0%.
{"title":"Bonenncarpas A–K: Coumarin derivatives with anti-inflammatory activity from Boenninghausenia sessilicarpa","authors":"Gang-Zhong Zhou , Ruo-Xi Hu , Qi-Jing Fan , Chu-Chu Xi , Yan-Gang Cao , Jia-Rui Li , Zheng-Yu Cao , Chun-Lei Zhang","doi":"10.1016/j.phytochem.2025.114415","DOIUrl":"10.1016/j.phytochem.2025.114415","url":null,"abstract":"<div><div>Eleven previously undescribed coumarin derivatives, bonenncarpas A–K (<strong>1</strong>–<strong>11</strong>), along with three known analogues (<strong>12</strong>–<strong>14</strong>), were isolated from the whole plant of <em>Boenninghausenia sessilicarpa</em>. The structures of these compounds were elucidated through comprehensive spectroscopic and spectrometric analyses. Their absolute configurations were determined by comparing experimental and calculated electronic circular dichroism data, as well as by X-ray crystallography. Notably, compound <strong>1</strong> features an open-ring coumarin structure with a five-membered lactone ring, while compounds <strong>9</strong>–<strong>11</strong> are characterized by a dihydrofuran ring at C-3 and C-4. All compounds were evaluated for their inhibitory effects on lipopolysaccharide-induced nitric oxide production in RAW 264.7 macrophage cells. At a concentration of 10 μM, compounds (−)-<strong>3</strong>, (+)-<strong>5</strong>, (+)-<strong>6</strong>, (+)-<strong>9</strong>, (−)-<strong>9</strong>, (+)-<strong>10</strong>, and (−)-<strong>10</strong> exhibited inhibition of NO production, ranging from 25.5% to 95.0%.</div></div>","PeriodicalId":20170,"journal":{"name":"Phytochemistry","volume":"234 ","pages":"Article 114415"},"PeriodicalIF":3.2,"publicationDate":"2025-01-29","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"143075031","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 : 2025-01-28DOI: 10.1016/j.phytochem.2025.114417
Peng Gao , Yu-Qi Wang , Shuo Yuan, Yan-Hang Wang, Ming-Bo Zhao, Ke-Wu Zeng, Yong Jiang, Qing-Ying Zhang, Peng-Fei Tu
Four pairs of previously undescribed enantiomers, including two pairs of dimeric phthalide-benzophenanthridine alkaloid and two pairs phthalides derivatives, corydecumbenpines A–D, were isolated from the rhizomes of Corydalis decumbens. Their planar structures were elucidated by extensive spectroscopic analysis including UV, IR, HRESIMS, 1D and 2D NMR. Optically pure compounds were obtained by chiral chromatography and their absolute configurations were determined by single-crystal X-ray crystallography and comparison of experimental and calculated ECD spectra. Corydecumbenpines A and B were previously undescribed phthalideisoquinolines which were benzophenanthridine linked to phthalide and corydecumbenpines C and D were previously undescribed phthalide hemiacetal derivatives. (+)-Corydecumbenpine A showed cytotoxic activity on A549, GIST-882, and PANC-1 cell lines with IC50 values of 10.1 μM, 8.2 μM, and 7.1 μM respectively.
{"title":"(+)/(−)-Corydecumbenpines A and B, two pairs of dimeric phthalide-benzophenanthridine alkaloids with cytotoxicity from Corydalis decumbens","authors":"Peng Gao , Yu-Qi Wang , Shuo Yuan, Yan-Hang Wang, Ming-Bo Zhao, Ke-Wu Zeng, Yong Jiang, Qing-Ying Zhang, Peng-Fei Tu","doi":"10.1016/j.phytochem.2025.114417","DOIUrl":"10.1016/j.phytochem.2025.114417","url":null,"abstract":"<div><div>Four pairs of previously undescribed enantiomers, including two pairs of dimeric phthalide-benzophenanthridine alkaloid and two pairs phthalides derivatives, corydecumbenpines A–D, were isolated from the rhizomes of <em>Corydalis decumbens</em>. Their planar structures were elucidated by extensive spectroscopic analysis including UV, IR, HRESIMS, 1D and 2D NMR. Optically pure compounds were obtained by chiral chromatography and their absolute configurations were determined by single-crystal X-ray crystallography and comparison of experimental and calculated ECD spectra. Corydecumbenpines A and B were previously undescribed phthalideisoquinolines which were benzophenanthridine linked to phthalide and corydecumbenpines C and D were previously undescribed phthalide hemiacetal derivatives. (+)-Corydecumbenpine A showed cytotoxic activity on A549, GIST-882, and PANC-1 cell lines with IC<sub>50</sub> values of 10.1 μM, 8.2 μM, and 7.1 μM respectively.</div></div>","PeriodicalId":20170,"journal":{"name":"Phytochemistry","volume":"233 ","pages":"Article 114417"},"PeriodicalIF":3.2,"publicationDate":"2025-01-28","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"143067284","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 : 2025-01-28DOI: 10.1016/j.phytochem.2025.114416
Xiao Han , Di Zhang , Xiaolei Li , Xiaobin Li , Xuli Tang , Guoqiang Li
Two undescribed rearranged diterpenoids, lobopaucinoids A and B (1 and 2), along with thirteen undescribed lobane-type diterpenoids lobopaucinoids C–O (3–15) including a C18 (11) and two C17 (12 and 13) undescribed norditerpenoids, were isolated from the soft coral Lobophytum pauciflorum Ehrenberg (Sarcophytidae family) collected from Xisha Islands of the South China Sea. Additionally, two undescribed prenyleudesmane-type diterpenoids, lobopaucinoids P and Q (16 and 17), as well as two known lobane diterpenoids (18 and 19), were also obtained. Their structures were elucidated based on comprehensive spectroscopic data, Mosher's method, Mo2(OAc)4 or Rh2(OCOCF3)4-induced circular dichroism experiment, quantum chemical calculations, and single-crystal X-ray diffraction and literature comparison. Biological evaluation indicated that compounds 3, 4 and 15 exhibited weak anti-inflammatory activities with the rates from 24.34 % to 35.13 % at the concentration of 20 μM. In addition, compound 1 showed significant hepatoprotective activity in zebrafish model.
{"title":"Lobopaucinoids A-Q, bioactive terpenoids from the soft coral Lobophytum pauciflorum collected in the South China Sea","authors":"Xiao Han , Di Zhang , Xiaolei Li , Xiaobin Li , Xuli Tang , Guoqiang Li","doi":"10.1016/j.phytochem.2025.114416","DOIUrl":"10.1016/j.phytochem.2025.114416","url":null,"abstract":"<div><div>Two undescribed rearranged diterpenoids, lobopaucinoids A and B (<strong>1</strong> and <strong>2</strong>), along with thirteen undescribed lobane-type diterpenoids lobopaucinoids C–O (<strong>3</strong>–<strong>15</strong>) including a C<sub>18</sub> (<strong>11</strong>) and two C<sub>17</sub> (<strong>12</strong> and <strong>13</strong>) undescribed norditerpenoids, were isolated from the soft coral <em>Lobophytum pauciflorum</em> Ehrenberg (Sarcophytidae family) collected from Xisha Islands of the South China Sea. Additionally, two undescribed prenyleudesmane-type diterpenoids, lobopaucinoids P and Q (<strong>16</strong> and <strong>17</strong>), as well as two known lobane diterpenoids (<strong>18</strong> and <strong>19</strong>), were also obtained. Their structures were elucidated based on comprehensive spectroscopic data, Mosher's method, Mo<sub>2</sub>(OAc)<sub>4</sub> or Rh<sub>2</sub>(OCOCF<sub>3</sub>)<sub>4</sub>-induced circular dichroism experiment, quantum chemical calculations, and single-crystal X-ray diffraction and literature comparison. Biological evaluation indicated that compounds <strong>3</strong>, <strong>4</strong> and <strong>15</strong> exhibited weak anti-inflammatory activities with the rates from 24.34 % to 35.13 % at the concentration of 20 μM. In addition, compound <strong>1</strong> showed significant hepatoprotective activity in zebrafish model.</div></div>","PeriodicalId":20170,"journal":{"name":"Phytochemistry","volume":"234 ","pages":"Article 114416"},"PeriodicalIF":3.2,"publicationDate":"2025-01-28","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"143067291","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 : 2025-01-22DOI: 10.1016/j.phytochem.2025.114411
Liangxiu Liao , Junguo Huang , Tao Zhu , Shan Ran , Qingpei Liu , Wenjing Wang , Xiaolong Yang
Cultivation of the endophytic fungus Robillarda sessilis XL-308 with SAHA resulted in the discovery of two previously undescribed cyclonerane sesquiterpenes (1 and 2), one previously unreported norcadinane type sesquiterpene (3), and seven suberanilohydroxamic acid (SAHA) derivatives (4–10). The identification of previously undescribed compounds was confirmed through NMR spectroscopic analyses, quantum chemistry calculations, and single-crystal X-ray crystallography. Among them, compounds 1 and 2 were products of the silenced genome in XL-308 that activated by SAHA. Concurrently, SAHA underwent biotransformation because of its moderate toxicity towards this fungus. It was hypothesized that the hydroxamic acid group in SAHA triggering the self-defense mechanism of XL-308 and converting SAHA into a less toxic derivative 5.
通过用 SAHA 培养内生真菌 Robillarda sessilis XL-308，发现了两种以前未曾报道过的环戊烷类倍半萜（1 和 2）、一种以前未曾报道过的去甲丁烷类倍半萜（3）和七种亚伯兰羟肟酸（SAHA）衍生物（4-10）。通过核磁共振光谱分析、量子化学计算和单晶 X 射线晶体学研究，确认了以前未曾报道过的化合物。其中，化合物 1 和 2 是 XL-308 中被 SAHA 激活的沉默基因组的产物。同时，由于 SAHA 对该真菌具有中等毒性，因此会发生生物转化。据推测，SAHA 中的羟肟酸基团触发了 XL-308 的自我防御机制，并将 SAHA 转化为毒性较低的衍生物 5。
{"title":"HDAC inhibitor SAHA triggers the production of previously undescribed sesquiterpenes and undergoes biotransformation by the fungus Robillarda sessilis from Verbena officinalis L.","authors":"Liangxiu Liao , Junguo Huang , Tao Zhu , Shan Ran , Qingpei Liu , Wenjing Wang , Xiaolong Yang","doi":"10.1016/j.phytochem.2025.114411","DOIUrl":"10.1016/j.phytochem.2025.114411","url":null,"abstract":"<div><div>Cultivation of the endophytic fungus <em>Robillarda sessilis</em> XL-308 with SAHA resulted in the discovery of two previously undescribed cyclonerane sesquiterpenes (<strong>1</strong> and <strong>2</strong>), one previously unreported norcadinane type sesquiterpene (<strong>3</strong>), and seven suberanilohydroxamic acid (SAHA) derivatives (<strong>4</strong>–<strong>10</strong>). The identification of previously undescribed compounds was confirmed through NMR spectroscopic analyses, quantum chemistry calculations, and single-crystal X-ray crystallography. Among them, compounds <strong>1</strong> and <strong>2</strong> were products of the silenced genome in XL-308 that activated by SAHA. Concurrently, SAHA underwent biotransformation because of its moderate toxicity towards this fungus. It was hypothesized that the hydroxamic acid group in SAHA triggering the self-defense mechanism of XL-308 and converting SAHA into a less toxic derivative <strong>5</strong>.</div></div>","PeriodicalId":20170,"journal":{"name":"Phytochemistry","volume":"233 ","pages":"Article 114411"},"PeriodicalIF":3.2,"publicationDate":"2025-01-22","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"143040983","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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