Pub Date : 2025-11-07DOI: 10.1016/j.phytochem.2025.114717
Lo-Yun Chen , Bo-Rong Peng , You-Ying Chen , Huong-Giang Le , Ngoc-Thac Pham , Yi-Ying Lin , Hung-Yi Chen , Pei-Jhen Hsieh , Mohamed El-Shazly , Kuei-Hung Lai
Lobane- and prenyleudesmane-type diterpenoids represent structurally unique and biologically diverse natural products, predominantly isolated from soft corals in the genera Lobophytum and Sinularia. This review comprehensively covers the literature from 1978 to 2025, isolation methods, structural elucidation, biological evaluations, and proposed biosynthetic pathways. Based on their reported bioactivities, the compounds were systematically classified, and their potential biosynthetic pathways were proposed. Additionally, a structure–activity relationship (SAR) analysis was conducted to further elucidate the functional groups responsible for their anti-inflammatory, toxicity and anti-fungal properties. To address the challenge of insufficient supply for biological assays, recent total syntheses of representative compounds were also highlighted, providing alternative solutions for future drug discovery and mechanistic studies. This review not only consolidates current knowledge but also provides perspectives for future biosynthetic studies and the development of marine-derived diterpenoids as therapeutic leads.
{"title":"Rare and underexplored lobane- and prenyleudesmane-type diterpenes primarily from corals with additional plant sources—Biosynthesis and pharmacological perspectives","authors":"Lo-Yun Chen , Bo-Rong Peng , You-Ying Chen , Huong-Giang Le , Ngoc-Thac Pham , Yi-Ying Lin , Hung-Yi Chen , Pei-Jhen Hsieh , Mohamed El-Shazly , Kuei-Hung Lai","doi":"10.1016/j.phytochem.2025.114717","DOIUrl":"10.1016/j.phytochem.2025.114717","url":null,"abstract":"<div><div>Lobane- and prenyleudesmane-type diterpenoids represent structurally unique and biologically diverse natural products, predominantly isolated from soft corals in the genera <em>Lobophytum</em> and <em>Sinularia</em>. This review comprehensively covers the literature from 1978 to 2025, isolation methods, structural elucidation, biological evaluations, and proposed biosynthetic pathways. Based on their reported bioactivities, the compounds were systematically classified, and their potential biosynthetic pathways were proposed. Additionally, a structure–activity relationship (SAR) analysis was conducted to further elucidate the functional groups responsible for their anti-inflammatory, toxicity and anti-fungal properties. To address the challenge of insufficient supply for biological assays, recent total syntheses of representative compounds were also highlighted, providing alternative solutions for future drug discovery and mechanistic studies. This review not only consolidates current knowledge but also provides perspectives for future biosynthetic studies and the development of marine-derived diterpenoids as therapeutic leads.</div></div>","PeriodicalId":20170,"journal":{"name":"Phytochemistry","volume":"242 ","pages":"Article 114717"},"PeriodicalIF":3.4,"publicationDate":"2025-11-07","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"145482705","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 : 2025-11-04DOI: 10.1016/j.phytochem.2025.114716
Su Hui Seong , Bohyun Yun , Jin-Ho Kim , Chan Seo , Seahee Han , Tae-Su Kim , Bo-Ram Kim , Ha-Nul Lee , Sua Im , Jung Eun Kim , Ji-Min Jung , Kyung-Min Choi , Jin-Woo Jeong
The genus Sedum is recognized for its diverse biological activities; however, the potential anti-depressive properties of Sedum kamtschaticum Fisch. & C. A. Mey. and S. takesimense Nakai, along with their bioactive constituents, remain unexplored. Therefore, this study was conducted to profile the phytochemicals of SK and ST and evaluate their antioxidant, anti-aging, and anti-monoamine oxidase potential in vitro. The 70 % ethanolic extracts of SK and ST showed radical-scavenging, anti-aging, and monoamine oxidase inhibitory activities. Through ultra-performance liquid chromatography–electrospray ionization–high-resolution quadrupole time-of-flight mass spectrometry, three phenolic acids, 12 phenolic glucosides, one ellagic acid, and 14 flavonoids were identified. Notably, four flavonoids were reported for the first time: gossypetin-3,5-di-O-β-d-glucopyranoside-8-O-β-d-xylopyranoside (7), gossypetin-3,5-di-O-β-d-glucopyranoside-8-O-α-l-arabinopyranoside (8), herbacetin-3,5-di-O-β-d-glucopyranoside-8-O-β-d-xylopyranoside (10), and herbacetin-3,5-di-O-β-d-glucopyranoside-8-O-α-l-arabinopyranoside (11), as characterized through mass spectrometry, ultraviolet, electronic circular dichroism, and nuclear magnetic resonance analyses. The biological activity assay revealed that most flavonoids exhibited significant antioxidant and lifespan-extending activities. Moreover, their aglycones—gossypetin and herbacetin—exhibited potent and selective inhibition of monoamine oxidase-B. These findings suggest that gossypetin- and herbacetin-based flavonols, the main active compounds in S. kamtschaticum Fisch. & C. A. Mey. and S. takesimense Nakai, may be employed as lead structures in the development of functional foods or drugs to prevent diseases caused by aging and neurotransmitter imbalances.
景天属以其多样的生物活性而闻名；然而，景天潜在的抗抑郁特性。& C. A.好的。和S. takesimense Nakai及其生物活性成分仍未被探索。因此，本研究对其植物化学成分进行了分析，并对其体外抗氧化、抗衰老和抗单胺氧化酶活性进行了评价。70%乙醇提取物具有清除自由基、抗衰老和抑制单胺氧化酶活性。通过超高效液相色谱-电喷雾电离-高分辨率四极杆飞行时间质谱分析，鉴定出3种酚类酸、12种酚类糖苷、1种鞣花酸和14种黄酮类化合物。值得注意的是，通过质谱、紫外、电子圆二色性和核磁共振分析，首次报道了四种黄酮类化合物：棉苷-3,5-二- o -β- d -葡萄糖吡喃苷-8- o -α- l -阿拉伯糖吡喃苷(7)、棉苷-3,5-二- o -β- d -葡萄糖吡喃苷-8- o -α- l -阿拉伯糖吡喃苷(8)、草糖苷-3,5-二- o -β- d -葡萄糖吡喃苷-8- o -α- l -阿拉伯糖吡喃苷（10）和草糖苷-3,5-二- o -β- d -葡萄糖吡喃苷-8- o -α- l -阿拉伯糖吡喃苷（11）。生物活性分析表明，大多数黄酮类化合物具有显著的抗氧化和延寿活性。此外，它们的糖基——棉籽苷和草菌素——表现出对单胺氧化酶- b的有效和选择性抑制。这些结果表明，棉黄酮醇和草黄酮醇是金缕草的主要活性化合物。& C. A.好的。和S. takesimense Nakai，可能被用作开发功能食品或药物的先导结构，以预防由衰老和神经递质失衡引起的疾病。
{"title":"Herbacetin and gossypetin glycosides from Sedum kamtschaticum Fisch. & C. A. Mey. and S. takesimense Nakai, and their antioxidant, anti-aging, and monoamine oxidase inhibitory activities","authors":"Su Hui Seong , Bohyun Yun , Jin-Ho Kim , Chan Seo , Seahee Han , Tae-Su Kim , Bo-Ram Kim , Ha-Nul Lee , Sua Im , Jung Eun Kim , Ji-Min Jung , Kyung-Min Choi , Jin-Woo Jeong","doi":"10.1016/j.phytochem.2025.114716","DOIUrl":"10.1016/j.phytochem.2025.114716","url":null,"abstract":"<div><div>The genus <em>Sedum</em> is recognized for its diverse biological activities; however, the potential anti-depressive properties of <em>Sedum kamtschaticum</em> Fisch. & C. A. Mey. and <em>S</em>. <em>takesimense</em> Nakai, along with their bioactive constituents, remain unexplored. Therefore, this study was conducted to profile the phytochemicals of SK and ST and evaluate their antioxidant, anti-aging, and anti-monoamine oxidase potential <em>in vitro</em>. The 70 % ethanolic extracts of SK and ST showed radical-scavenging, anti-aging, and monoamine oxidase inhibitory activities. Through ultra-performance liquid chromatography–electrospray ionization–high-resolution quadrupole time-of-flight mass spectrometry, three phenolic acids, 12 phenolic glucosides, one ellagic acid, and 14 flavonoids were identified. Notably, four flavonoids were reported for the first time: gossypetin-3,5-di-<em>O</em>-β-<span>d</span>-glucopyranoside-8-<em>O</em>-β-<span>d</span>-xylopyranoside (<strong>7</strong>), gossypetin-3,5-di-<em>O</em>-β-<span>d</span>-glucopyranoside-8-<em>O</em>-α-<span>l</span>-arabinopyranoside (<strong>8</strong>), herbacetin-3,5-di-<em>O</em>-β-<span>d</span>-glucopyranoside-8-<em>O</em>-β-<span>d</span>-xylopyranoside (<strong>10</strong>), and herbacetin-3,5-di-<em>O</em>-β-<span>d</span>-glucopyranoside-8-<em>O</em>-α-<span>l</span>-arabinopyranoside (<strong>11</strong>), as characterized through mass spectrometry, ultraviolet, electronic circular dichroism, and nuclear magnetic resonance analyses. The biological activity assay revealed that most flavonoids exhibited significant antioxidant and lifespan-extending activities. Moreover, their aglycones—gossypetin and herbacetin—exhibited potent and selective inhibition of monoamine oxidase-B. These findings suggest that gossypetin- and herbacetin-based flavonols, the main active compounds in <em>S</em>. <em>kamtschaticum</em> Fisch. & C. A. Mey. and <em>S</em>. <em>takesimense</em> Nakai, may be employed as lead structures in the development of functional foods or drugs to prevent diseases caused by aging and neurotransmitter imbalances.</div></div>","PeriodicalId":20170,"journal":{"name":"Phytochemistry","volume":"242 ","pages":"Article 114716"},"PeriodicalIF":3.4,"publicationDate":"2025-11-04","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"145459487","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 : 2025-10-26DOI: 10.1016/j.phytochem.2025.114713
Ming Hu , Run-Cheng Yan , Qiao-Ling Wei, Jiang-Li Su, Bi-Juan Yang, Wen-Chao Tu, Gan-Peng Li, Xing-De Wu
Chemical investigation of the plant pathogen Alternaria solani, associated with Hypoestes phyllostachya, led to the isolation of alternsolain A (1), an unprecedented alternariol-zinnol hybrid, and alternsolains B-G (2–7), six previously undescribed zinnol derivatives containing two pairs of enantiomers, (±)-alternsolains E (5) and F (6), along with five known compounds (8–12). Their structures were elucidated using comprehensive spectral analysis, single-crystal X-ray diffraction, NMR computational techniques, and electronic circular dichroism calculations. Compound 1 possessed a previously unreported carbon skeleton formed through the linkage of alternariol and zinnol via C-8-C-4′ bond. Compound 2 featured a rare dimeric skeleton composed of two zinnol units connected by an ether bond. Plausible biosynthetic pathways for 1 and 2 were also postulated. Additionally, compound 9 showed potent cytotoxic activities against HL-60, MDA-MB-231, and SW480 human cancer cell lines, with IC50 values of 10.73 ± 0.08, 19.40 ± 0.97, and 29.72 ± 1.61 μM, respectively. These results enrich the diversity of zinnols and may provide active compounds for the development of new anticancer drugs.
{"title":"An unprecedented alternariol-zinnol hybrid and six undescribed zinnol derivatives from the phytopathogen Alternaria solani and their cytotoxic activities","authors":"Ming Hu , Run-Cheng Yan , Qiao-Ling Wei, Jiang-Li Su, Bi-Juan Yang, Wen-Chao Tu, Gan-Peng Li, Xing-De Wu","doi":"10.1016/j.phytochem.2025.114713","DOIUrl":"10.1016/j.phytochem.2025.114713","url":null,"abstract":"<div><div>Chemical investigation of the plant pathogen <em>Alternaria solani</em>, associated with <em>Hypoestes phyllostachya</em>, led to the isolation of alternsolain A (<strong>1</strong>), an unprecedented alternariol-zinnol hybrid, and alternsolains B-G (<strong>2</strong>–<strong>7</strong>), six previously undescribed zinnol derivatives containing two pairs of enantiomers, (±)-alternsolains E (<strong>5</strong>) and F (<strong>6</strong>), along with five known compounds (<strong>8</strong>–<strong>12</strong>). Their structures were elucidated using comprehensive spectral analysis, single-crystal X-ray diffraction, NMR computational techniques, and electronic circular dichroism calculations. Compound <strong>1</strong> possessed a previously unreported carbon skeleton formed through the linkage of alternariol and zinnol via C-8-C-4′ bond. Compound <strong>2</strong> featured a rare dimeric skeleton composed of two zinnol units connected by an ether bond. Plausible biosynthetic pathways for <strong>1</strong> and <strong>2</strong> were also postulated. Additionally, compound <strong>9</strong> showed potent cytotoxic activities against HL-60, MDA-MB-231, and SW480 human cancer cell lines, with IC<sub>50</sub> values of 10.73 ± 0.08, 19.40 ± 0.97, and 29.72 ± 1.61 μM, respectively. These results enrich the diversity of zinnols and may provide active compounds for the development of new anticancer drugs.</div></div>","PeriodicalId":20170,"journal":{"name":"Phytochemistry","volume":"242 ","pages":"Article 114713"},"PeriodicalIF":3.4,"publicationDate":"2025-10-26","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"145392166","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 : 2025-10-24DOI: 10.1016/j.phytochem.2025.114715
Ruitao Yu , Shiwen Kang , Yuanren Ma , Haitao Cheng , Jinghua Chen , Yanduo Tao , Wei Xiong , Xinzhou Yang
Eight previously undescribed compounds, davidinins B–G (1–4, 5a, 5b, 6a and 6b), including two sets of enantiomeric pairs (5a/5b and 6a/6b) together with six known compounds, were isolated from the ethyl acetate fractions of the roots of Sophora davidii (Franch.) Skeels. Using chiral HPLC, the enantiomers (+)-(3R,4R)-davidinin F (5a), (−)-(3S,4S)-davidinin F (5b), (+)-(R)-davidinin G (6a), and (−)-(S)-davidinin G (6b) were successfully separated and obtained. Their planer structures were established through analysis of 1D and 2D NMR and HRESIMS data. The absolute configurations of the previously undescribed compounds were mainly determined by NMR calculation and electronic circular dichroism (ECD) calculation. At a concentration of 20 μg/mL, compounds 1–4, 5a, 5b, 6a, 6b, and 7–9 modulated GLUT4 translocation to 1.15–2.47-fold of the control; among them, compound 4 exhibited the strongest increase.
从苦参（Sophora davidii）根的乙酸乙酯部分分离得到8个先前未被描述的化合物，davidinins B-G (1 - 4,5a, 5b, 6a， 6a和6b)，包括两组对映体对（5a/5b和6a/6b）和6个已知化合物。斯基尔。采用手性高效液相色谱法成功分离得到(+)-(3R,4R)-davidinin F (5a),(−)-(3S,4S)-davidinin F (5b), (+)-(R)-davidinin G (6a),(−)-(S)-davidinin G （6b）对映体。通过分析一维和二维NMR和hremsims数据，建立了它们的平面结构。上述化合物的绝对构型主要通过核磁共振计算和电子圆二色性（ECD）计算确定。在浓度为20 μg/mL时，化合物1-4、5a、5b、6a、6b和7-9调节GLUT4易位为对照的1.15 - 2.47倍；其中化合物4增幅最大。
{"title":"Previously undescribed isoflavan-stilbene dimers from the roots of Sophora davidii (Franch.) skeels and their glucose transporter 4 translocation activities","authors":"Ruitao Yu , Shiwen Kang , Yuanren Ma , Haitao Cheng , Jinghua Chen , Yanduo Tao , Wei Xiong , Xinzhou Yang","doi":"10.1016/j.phytochem.2025.114715","DOIUrl":"10.1016/j.phytochem.2025.114715","url":null,"abstract":"<div><div>Eight previously undescribed compounds, davidinins B–G (<strong>1</strong>–<strong>4</strong>, <strong>5a</strong>, <strong>5b</strong>, <strong>6a</strong> and <strong>6b</strong>), including two sets of enantiomeric pairs (<strong>5a</strong>/<strong>5b</strong> and <strong>6a</strong>/<strong>6b</strong>) together with six known compounds, were isolated from the ethyl acetate fractions of the roots of <em>Sophora davidii</em> (Franch.) Skeels. Using chiral HPLC, the enantiomers (+)-(3<em>R</em>,4<em>R</em>)-davidinin F (<strong>5a</strong>), (−)-(3<em>S</em>,4<em>S</em>)-davidinin F (<strong>5b</strong>), (+)-(<em>R</em>)-davidinin G (<strong>6a</strong>), and (−)-(<em>S</em>)-davidinin G (<strong>6b</strong>) were successfully separated and obtained. Their planer structures were established through analysis of 1D and 2D NMR and HRESIMS data. The absolute configurations of the previously undescribed compounds were mainly determined by NMR calculation and electronic circular dichroism (ECD) calculation. At a concentration of 20 μg/mL, compounds <strong>1</strong>–<strong>4</strong>, <strong>5a</strong>, <strong>5b</strong>, <strong>6a</strong>, <strong>6b</strong>, and <strong>7</strong>–<strong>9</strong> modulated GLUT4 translocation to 1.15–2.47-fold of the control; among them, compound <strong>4</strong> exhibited the strongest increase.</div></div>","PeriodicalId":20170,"journal":{"name":"Phytochemistry","volume":"242 ","pages":"Article 114715"},"PeriodicalIF":3.4,"publicationDate":"2025-10-24","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"145417757","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}
A phytochemical investigation into the low-polarity fraction of Artemisia capillaris facilitated the isolation of twenty-two natural compounds. These compounds, termed Artemicapillasin O-X (1a/1b-4a/4b, 5a, 6a/6b-8a/8b, 9a, 10b, 11b, 12a, and 12b), were identified as previously undescribed 2,3-dihydrobenzofuran (2,3-DHB) derivatives. Their structures were elucidated using NMR analysis, which included coupling constant analysis, chiroptical characterization (electronic circular dichroism [ECD] and optical rotatory dispersion [ORD]), computational approaches (DP4+ probability analysis and dJ/iJ-DP4 protocol), and X-ray diffraction. Subsequent analyses identified that for 2,3-DHB derivatives featuring only two chiral centers at C-2 and C-10, the determination of absolute configuration relies on coupling constants, Cotton effects in CD spectra, and ORD measurements. A novel rule, termed Chen's Rule, was established to facilitate rapid discrimination of stereochemical relationships between H-2 and H-10 in 2,3-DHB derivatives. This rule prompted structural revisions of similar compounds reported in the prior literature. Furthermore, all compounds were assayed at a concentration of 100 μM for their inhibitory activity against xanthine oxidase (XOD) in vitro, where compounds 7a and 7b displayed moderate effects, whereas the others demonstrated negligible activity.
{"title":"Challenges in chiral discrimination at the H-2 and H-10 positions of dihydrobenzofuran from Artemisia capillaris","authors":"Junping Chen , Maoni Ren , Liangyu Huang , Yuxia Lou , Xinyao Hou , Yuge Zhang , Guozheng Huang , Jianguo Cao","doi":"10.1016/j.phytochem.2025.114711","DOIUrl":"10.1016/j.phytochem.2025.114711","url":null,"abstract":"<div><div>A phytochemical investigation into the low-polarity fraction of <em>Artemisia capillaris</em> facilitated the isolation of twenty-two natural compounds. These compounds, termed Artemicapillasin O-X (<strong>1a</strong>/<strong>1b</strong>-<strong>4a</strong>/<strong>4b</strong>, <strong>5a</strong>, <strong>6a</strong>/<strong>6b</strong>-<strong>8a</strong>/<strong>8b</strong>, <strong>9a</strong>, <strong>10b</strong>, <strong>11b</strong>, <strong>12a</strong>, and <strong>12b</strong>), were identified as previously undescribed 2,3-dihydrobenzofuran (2,3-DHB) derivatives. Their structures were elucidated using NMR analysis, which included coupling constant analysis, chiroptical characterization (electronic circular dichroism [ECD] and optical rotatory dispersion [ORD]), computational approaches (DP4+ probability analysis and d<em>J</em>/i<em>J</em>-DP4 protocol), and X-ray diffraction. Subsequent analyses identified that for 2,3-DHB derivatives featuring only two chiral centers at C-2 and C-10, the determination of absolute configuration relies on coupling constants, Cotton effects in CD spectra, and ORD measurements. A novel rule, termed Chen's Rule, was established to facilitate rapid discrimination of stereochemical relationships between H-2 and H-10 in 2,3-DHB derivatives. This rule prompted structural revisions of similar compounds reported in the prior literature. Furthermore, all compounds were assayed at a concentration of 100 μM for their inhibitory activity against xanthine oxidase (XOD) <em>in vitro</em>, where compounds <strong>7a</strong> and <strong>7b</strong> displayed moderate effects, whereas the others demonstrated negligible activity.</div></div>","PeriodicalId":20170,"journal":{"name":"Phytochemistry","volume":"242 ","pages":"Article 114711"},"PeriodicalIF":3.4,"publicationDate":"2025-10-23","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"145370440","PeriodicalName":null,"FirstCategoryId":null,"ListUrlMain":null,"RegionNum":2,"RegionCategory":"生物学","ArticlePicture":[],"TitleCN":null,"AbstractTextCN":null,"PMCID":"","EPubDate":null,"PubModel":null,"JCR":null,"JCRName":null,"Score":null,"Total":0}
Four previously undescribed Euphorbia diterpenoids (1–3, 13), along with 19 known derivatives (4–12, 14–23), were isolated from the whole plant of Euphorbia peplus. Their structures were characterized by a combination of spectroscopic studies, single-crystal X-ray diffraction and ECD calculations. In this study, all isolates were investigated for their effects on the expression of ABCA1 protein in BV-2 cells. Compound 4 increased ABCA1 levels in a dose-dependent manner. Network pharmacology analysis predicted that PPARγ might be the potential target for the anti-AD effect of compound 4. Binding of 4 to the PPARγ was further confirmed by the fluorescence quenching assay, surface plasmon resonance, fluorescein-labeled differential scanning fluorimetry method, and molecular docking technology. Thus, compound 4 may exert anti-AD effect by targeting PPARγ and upregulating the level of ABCA1.
{"title":"Euphorbia diterpenoids from Euphorbia peplus possessing anti-Alzheimer's activity via targeting PPARγ and upregulating the level of ABCA1","authors":"Yanlan Yang , Shoulun He , Yingting Lin, Junjie Chen, Renjing Yang, Xueli Li, Jingyu Sun, Guanghui Wang, Wenjing Tian, Haifeng Chen","doi":"10.1016/j.phytochem.2025.114712","DOIUrl":"10.1016/j.phytochem.2025.114712","url":null,"abstract":"<div><div>Four previously undescribed <em>Euphorbia</em> diterpenoids (<strong>1–3</strong>, <strong>13</strong>), along with 19 known derivatives (<strong>4</strong>–<strong>12</strong>, <strong>14</strong>–<strong>23</strong>), were isolated from the whole plant of <em>Euphorbia peplus</em>. Their structures were characterized by a combination of spectroscopic studies, single-crystal X-ray diffraction and ECD calculations. In this study, all isolates were investigated for their effects on the expression of ABCA1 protein in BV-2 cells. Compound <strong>4</strong> increased ABCA1 levels in a dose-dependent manner. Network pharmacology analysis predicted that PPAR<em>γ</em> might be the potential target for the anti-AD effect of compound <strong>4</strong>. Binding of <strong>4</strong> to the PPAR<em>γ</em> was further confirmed by the fluorescence quenching assay, surface plasmon resonance, fluorescein-labeled differential scanning fluorimetry method, and molecular docking technology. Thus, compound <strong>4</strong> may exert anti-AD effect by targeting PPAR<em>γ</em> and upregulating the level of ABCA1.</div></div>","PeriodicalId":20170,"journal":{"name":"Phytochemistry","volume":"242 ","pages":"Article 114712"},"PeriodicalIF":3.4,"publicationDate":"2025-10-22","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"145368542","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 : 2025-10-21DOI: 10.1016/j.phytochem.2025.114714
Tingting Guo , Kepu Huang , Qingfang Wang , Chen Peng , Xingping Zhang , Congxi Gao , Kou Wang , Hongping He , Mingming Li
Six undescribed flavans (1–6) and four known analogues (7–10) were isolated from the leaves of Broussonetia papyrifera with the guidance of 1H NMR. Among them, 1 and 2 were characterized as prenylflavan derivatives with hydroxymethyl and ethoxy moiety, respectively. Their structures were established through comprehensive analysis of spectroscopic data, including HRESIMS, 1D and 2D NMR. The absolute configurations were determined by theoretical calculations of electronic circular dichroism. Notably, compounds 5 and 6 exhibited superior α-glucosidase inhibitory activities with IC50 values of 5.87 and 6.26 μM, respectively. Additionally, molecular docking and molecular dynamics simulations were performed using 5 and 6 with IMA1, an α-glucosidase derived from Saccharomyces cerevisiae, to analyze their potential binding sites.
{"title":"1H NMR guided isolation of flavans from Broussonetia papyrifera and their α-glucosidase inhibitory activity","authors":"Tingting Guo , Kepu Huang , Qingfang Wang , Chen Peng , Xingping Zhang , Congxi Gao , Kou Wang , Hongping He , Mingming Li","doi":"10.1016/j.phytochem.2025.114714","DOIUrl":"10.1016/j.phytochem.2025.114714","url":null,"abstract":"<div><div>Six undescribed flavans (<strong>1–6</strong>) and four known analogues (<strong>7–10</strong>) were isolated from the leaves of <em>Broussonetia papyrifera</em> with the guidance of <sup>1</sup>H NMR. Among them, <strong>1</strong> and <strong>2</strong> were characterized as prenylflavan derivatives with hydroxymethyl and ethoxy moiety, respectively. Their structures were established through comprehensive analysis of spectroscopic data, including HRESIMS, 1D and 2D NMR. The absolute configurations were determined by theoretical calculations of electronic circular dichroism. Notably, compounds <strong>5</strong> and <strong>6</strong> exhibited superior <em>α</em>-glucosidase inhibitory activities with IC<sub>50</sub> values of 5.87 and 6.26 μM, respectively. Additionally, molecular docking and molecular dynamics simulations were performed using <strong>5</strong> and <strong>6</strong> with IMA1, an <em>α</em>-glucosidase derived from <em>Saccharomyces cerevisiae</em>, to analyze their potential binding sites.</div></div>","PeriodicalId":20170,"journal":{"name":"Phytochemistry","volume":"242 ","pages":"Article 114714"},"PeriodicalIF":3.4,"publicationDate":"2025-10-21","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"145355664","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 : 2025-10-21DOI: 10.1016/j.phytochem.2025.114710
Yury Shkryl , Olga Grishchenko , Elena Vasileva , Natalia Mishchenko , Elena Vasyutkina , Egor Alaverdov , Olesya Kudinova , Galina Tchernoded , Alexandra Fialko , Zhargalma Tsydeneshieva , Maria Sorokina , Yulia Yaroshenko , Anton Degtyarenko , Sergey Fedoreyev , Victor Bulgakov , Yulia Yugay
This study investigates how the Ib-rolB/C (root locus B/C) gene from sweet potato (Ipomoea batatas), a naturally transgenic plant, influences growth and secondary metabolism in Rubia cordifolia callus cultures. Specifically, its role in regulating anthraquinone (AQ) biosynthesis via calcium-dependent signaling pathways was examined. Transgenic callus lines expressing Ib-rolB/C exhibited robust growth and up to a sixfold increase in AQ production compared to non-transformed controls, particularly when cultured on cytokinin-enriched media. Gene expression analysis revealed strong upregulation of key biosynthetic genes (RcICS, RcOSBS, RcOSBL, and RcIPPi) as well as several calcium-dependent protein kinase (CDPK) isoforms, supporting the hypothesis that Ib-rolB/C modulates calcium-responsive pathways that contribute to the activation of secondary metabolism. Experiments under calcium-deficient and calcium-excess conditions in the culture medium, together with calcium channel inhibitor treatments, confirmed that AQ biosynthesis in transgenic lines is tightly coupled to calcium levels, whereas biomass accumulation was less affected. These findings highlight the regulatory function of Ib-rolB/C in linking calcium signaling with secondary metabolism and offer new insights into the molecular mechanisms of naturally transgenic systems.
{"title":"Calcium-dependent regulation of anthraquinone biosynthesis by the sweet potato Ib-rolb/C gene in Rubia cordifolia callus cultures","authors":"Yury Shkryl , Olga Grishchenko , Elena Vasileva , Natalia Mishchenko , Elena Vasyutkina , Egor Alaverdov , Olesya Kudinova , Galina Tchernoded , Alexandra Fialko , Zhargalma Tsydeneshieva , Maria Sorokina , Yulia Yaroshenko , Anton Degtyarenko , Sergey Fedoreyev , Victor Bulgakov , Yulia Yugay","doi":"10.1016/j.phytochem.2025.114710","DOIUrl":"10.1016/j.phytochem.2025.114710","url":null,"abstract":"<div><div>This study investigates how the <em>Ib-rolB/C</em> (<u>ro</u>ot <u>l</u>ocus <em>B/C</em>) gene from sweet potato (<em>Ipomoea batatas</em>), a naturally transgenic plant, influences growth and secondary metabolism in <em>Rubia cordifolia</em> callus cultures. Specifically, its role in regulating anthraquinone (AQ) biosynthesis via calcium-dependent signaling pathways was examined. Transgenic callus lines expressing <em>Ib-rolB/C</em> exhibited robust growth and up to a sixfold increase in AQ production compared to non-transformed controls, particularly when cultured on cytokinin-enriched media. Gene expression analysis revealed strong upregulation of key biosynthetic genes (<em>RcICS</em>, <em>RcOSBS</em>, <em>RcOSBL</em>, and <em>RcIPPi</em>) as well as several calcium-dependent protein kinase (<em>CDPK</em>) isoforms, supporting the hypothesis that <em>Ib-rolB/C</em> modulates calcium-responsive pathways that contribute to the activation of secondary metabolism. Experiments under calcium-deficient and calcium-excess conditions in the culture medium, together with calcium channel inhibitor treatments, confirmed that AQ biosynthesis in transgenic lines is tightly coupled to calcium levels, whereas biomass accumulation was less affected. These findings highlight the regulatory function of <em>Ib-rolB/C</em> in linking calcium signaling with secondary metabolism and offer new insights into the molecular mechanisms of naturally transgenic systems.</div></div>","PeriodicalId":20170,"journal":{"name":"Phytochemistry","volume":"242 ","pages":"Article 114710"},"PeriodicalIF":3.4,"publicationDate":"2025-10-21","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"145355671","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 : 2025-10-20DOI: 10.1016/j.phytochem.2025.114709
Jonathan Sorres , Juliette Segret , Elsa Van-Elslande , David Touboul , Véronique Eparvier
An original approach was undertaken to explore the metabolomic variability of macroscopic fungi collected in French Guiana. Extracts from 160 specimens, representing 13 fungal orders, were analyzed using liquid chromatography coupled with tandem mass spectrometry (LC-MS/MS). The resulting metabolomic profiles enabled the construction of chemotaxonomic dendrograms, which successfully grouped most samples assigned to the order Xylariales and highlighted chemodiversity at both the genus and species levels within this lineage. Principal Component Analysis based on molecular family presence/absence revealed 35 discriminant clusters, including specific markers distinguishing Thamnomyces chordalis and Phylacia sp. Five previously undescribed natural products were isolated and structurally characterized: four polyketides—prochordapyrone (1) and chordapyrones A–C (2–4)—and one terpenoid, chordapyranone (5). Structural elucidation was accomplished through a combination of nuclear magnetic resonance (NMR) spectroscopy, circular dichroism and single-crystal X-ray diffraction. Based on structural and mechanistic considerations, a putative biosynthetic pathway was proposed for the formation of the polyketide compounds.
{"title":"Metabolomic analysis of macromycetes from French Guiana reveals chemodiversity in Xylariales order","authors":"Jonathan Sorres , Juliette Segret , Elsa Van-Elslande , David Touboul , Véronique Eparvier","doi":"10.1016/j.phytochem.2025.114709","DOIUrl":"10.1016/j.phytochem.2025.114709","url":null,"abstract":"<div><div>An original approach was undertaken to explore the metabolomic variability of macroscopic fungi collected in French Guiana. Extracts from 160 specimens, representing 13 fungal orders, were analyzed using liquid chromatography coupled with tandem mass spectrometry (LC-MS/MS). The resulting metabolomic profiles enabled the construction of chemotaxonomic dendrograms, which successfully grouped most samples assigned to the order Xylariales and highlighted chemodiversity at both the genus and species levels within this lineage. Principal Component Analysis based on molecular family presence/absence revealed 35 discriminant clusters, including specific markers distinguishing <em>Thamnomyces chordalis</em> and <em>Phylacia</em> sp. Five previously undescribed natural products were isolated and structurally characterized: four polyketides—prochordapyrone (<strong>1</strong>) and chordapyrones A–C (<strong>2</strong>–<strong>4</strong>)—and one terpenoid, chordapyranone (<strong>5</strong>). Structural elucidation was accomplished through a combination of nuclear magnetic resonance (NMR) spectroscopy, circular dichroism and single-crystal X-ray diffraction. Based on structural and mechanistic considerations, a putative biosynthetic pathway was proposed for the formation of the polyketide compounds.</div></div>","PeriodicalId":20170,"journal":{"name":"Phytochemistry","volume":"242 ","pages":"Article 114709"},"PeriodicalIF":3.4,"publicationDate":"2025-10-20","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"145346430","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}
Anethole, a naturally-occurring aromatic phenylpropene compound, is commonly present in the essential oils derived from botanically diverse plants, including anise, star anise, fennel and basil. It is highly regarded for its therapeutic properties, imparting various health benefits spanning many different conditions. This comprehensive and critical review unites the knowledge on anethole up to the year 2024, available from the scientific platforms Scopus, PubMed and Web of Science, retrieved using the search term “Anethole". A bibliometrics overview is also provided which outlines the trend in the publication output over time, the major contributing authors, collaborative networks and popular research topics on this molecule. The collected data suggests that, in addition to its significance in the flavour and fragrance sectors, anethole exhibits a host of diverse medicinal activities. In-depth research highlights its contributing potential in addressing cancer, infections, wounds, and conditions related to the liver, lungs and skin. However, the research on anethole lacks comprehensive investigations into its mechanisms of action and synergistic effects with other compounds, hindering the understanding of its full therapeutic potential. While it holds promise beyond culinary uses, further research is needed to address this knowledge void and develop targeted therapeutic interventions.
茴香醚是一种天然存在的芳香苯丙烯化合物，通常存在于从多种植物中提取的精油中，包括大茴香、八角茴香、茴香和罗勒。它因其治疗特性而受到高度重视，在许多不同的条件下赋予各种健康益处。这篇全面而批判性的综述结合了截至2024年的有关麻醉药的知识，这些知识可以从科学平台Scopus、PubMed和Web of Science上获得，使用搜索词“麻醉药”进行检索。本文还提供了文献计量学综述，概述了随着时间的推移，该分子的出版输出趋势，主要贡献作者，合作网络和流行的研究课题。收集到的数据表明，除了其在风味和香料领域的重要性外，茴香油还具有多种药用活性。深入的研究突出了它在治疗癌症、感染、伤口以及与肝、肺和皮肤有关的疾病方面的贡献潜力。然而，对茴香脑的研究缺乏对其作用机制和与其他化合物协同作用的全面研究，阻碍了对其全部治疗潜力的认识。虽然它在烹饪应用之外具有前景，但需要进一步的研究来解决这一知识空白并开发有针对性的治疗干预措施。
{"title":"More than just flavour and fragrance – the chemistry and pharmacological potential of anethole","authors":"Ruchi Badoni Semwal , Deepak Kumar Semwal , Ankit Kumar , Maxleene Sandasi , Alvaro Viljoen","doi":"10.1016/j.phytochem.2025.114708","DOIUrl":"10.1016/j.phytochem.2025.114708","url":null,"abstract":"<div><div>Anethole, a naturally-occurring aromatic phenylpropene compound, is commonly present in the essential oils derived from botanically diverse plants, including anise, star anise, fennel and basil. It is highly regarded for its therapeutic properties, imparting various health benefits spanning many different conditions. This comprehensive and critical review unites the knowledge on anethole up to the year 2024, available from the scientific platforms Scopus, PubMed and Web of Science, retrieved using the search term “Anethole\". A bibliometrics overview is also provided which outlines the trend in the publication output over time, the major contributing authors, collaborative networks and popular research topics on this molecule. The collected data suggests that, in addition to its significance in the flavour and fragrance sectors, anethole exhibits a host of diverse medicinal activities. In-depth research highlights its contributing potential in addressing cancer, infections, wounds, and conditions related to the liver, lungs and skin. However, the research on anethole lacks comprehensive investigations into its mechanisms of action and synergistic effects with other compounds, hindering the understanding of its full therapeutic potential. While it holds promise beyond culinary uses, further research is needed to address this knowledge void and develop targeted therapeutic interventions.</div></div>","PeriodicalId":20170,"journal":{"name":"Phytochemistry","volume":"242 ","pages":"Article 114708"},"PeriodicalIF":3.4,"publicationDate":"2025-10-15","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"145313276","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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