Manh Tuan Ha , Thi Thanh Le , Da Yeong Lee , Chung Sub Kim , Ui Joung Youn , Sang Hee Kim , Jeong Ah Kim , Byung Sun Min
{"title":"Chemical constituents of Himantormia lugubris collected from Antarctica and their PTP1B and α-glucosidase inhibitory activities","authors":"Manh Tuan Ha , Thi Thanh Le , Da Yeong Lee , Chung Sub Kim , Ui Joung Youn , Sang Hee Kim , Jeong Ah Kim , Byung Sun Min","doi":"10.1016/j.phytol.2025.02.009","DOIUrl":"10.1016/j.phytol.2025.02.009","url":null,"abstract":"<div><div>A phytochemical investigation of an Antarctic endemic species [<em>Himantormia lugubris</em> (Hue) M. Lamb] led to the isolation and structural elucidation of three new compounds including one lanostane-type triterpenoid (<strong>1</strong>, himanlugubrol A), one ergostane-type sterol (<strong>2</strong>, himanlugubrol B), one benzyl orsellinate derivative (<strong>3</strong>, himanlugubrin A), along with ten known compounds (<strong>4</strong>−<strong>13</strong>). The chemical structures of new compounds were determined using diverse NMR techniques, HRESIMS data analysis, and computational approaches supported by advanced statistics (DP4+). The anti-diabetic potential of all isolated compounds was investigated by evaluating their inhibitory effects on PTP1B and α-glucosidase enzymes. As a result, compound <strong>3</strong> moderately inhibited PTP1B with an IC<sub>50</sub> value of 43.86 µM and significantly inhibited α-glucosidase (IC<sub>50</sub> = 73.46 µM) in comparison to the positive controls, ursolic acid (IC<sub>50</sub> = 5.92 µM) and acarbose (IC<sub>50</sub> = 210.11 µM), respectively. Enzyme kinetic analysis revealed that compound <strong>3</strong> demonstrated noncompetitive inhibition of PTP1B and mixed-type inhibition of α-glucosidase. Additionally, molecular docking results supported these in vitro findings, showing that compound <strong>3</strong> had strong binding affinities for the active sites of both PTP1B and α-glucosidase, indicated by the key H-bond and van der Waals interactions and negative binding energies.</div></div>","PeriodicalId":20408,"journal":{"name":"Phytochemistry Letters","volume":"66 ","pages":"Pages 91-99"},"PeriodicalIF":1.3,"publicationDate":"2025-02-24","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"143474041","PeriodicalName":null,"FirstCategoryId":null,"ListUrlMain":null,"RegionNum":4,"RegionCategory":"生物学","ArticlePicture":[],"TitleCN":null,"AbstractTextCN":null,"PMCID":"","EPubDate":null,"PubModel":null,"JCR":null,"JCRName":null,"Score":null,"Total":0}
Junzhi Pan , Guohao Hu , Feijing Lv , Zhongyang Shi , Wuming Dong , Yu Qi , Chaojie Wang , Haibing Tong , Fangjian Huang , Pengcheng Yan
{"title":"Sargafusal, a rare norsesquiterpenoid from the edible brown alga Sargassum fusiforme","authors":"Junzhi Pan , Guohao Hu , Feijing Lv , Zhongyang Shi , Wuming Dong , Yu Qi , Chaojie Wang , Haibing Tong , Fangjian Huang , Pengcheng Yan","doi":"10.1016/j.phytol.2025.02.008","DOIUrl":"10.1016/j.phytol.2025.02.008","url":null,"abstract":"<div><div>A previously undescribed C<sub>14</sub>-norsesquiterpenoid aldehyde with a hexahydrobenzofuran scaffold, sargafusal (<strong>1</strong>), was isolated from an EtOAc-soluble extract of the edible brown alga <em>Sargassum fusiforme</em>, together with three known norisoprenoids (<strong>2</strong>–<strong>4</strong>). The chemical structure of sargafusal (<strong>1</strong>) was established by extensive spectroscopic analyses, including 1D and 2D NMR, ECD and DFT-calculated ECD, and HR-ESI-MS data. Sargafusal (<strong>1</strong>) represents the first C<sub>14</sub>-norsesquiterpenoid aldehyde from the family Sargassaceae<em>.</em> Compounds <strong>1</strong>, <strong>3</strong>, and <strong>4</strong> showed potent antioxidant neuroprotective effects against H<sub>2</sub>O<sub>2</sub>-induced oxidative damage in neuron-like PC12 cells. This study provides new insight into the drug discovery efforts on the promising neuroprotective lead compounds from marine algae resource.</div></div>","PeriodicalId":20408,"journal":{"name":"Phytochemistry Letters","volume":"66 ","pages":"Pages 86-90"},"PeriodicalIF":1.3,"publicationDate":"2025-02-19","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"143444353","PeriodicalName":null,"FirstCategoryId":null,"ListUrlMain":null,"RegionNum":4,"RegionCategory":"生物学","ArticlePicture":[],"TitleCN":null,"AbstractTextCN":null,"PMCID":"","EPubDate":null,"PubModel":null,"JCR":null,"JCRName":null,"Score":null,"Total":0}
Ke-Xin Qin , Hao Wang , Li Yang , Yan-Mei Wei , Cai-Hong Cai , Hui-Qin Chen , Wen-Hua Dong , Wei Li , Xian-Yun Yan , Jun Zeng , Wen-Li Mei , Jie Jian , Haofu Dai
{"title":"Two unprecedented 5,6,7,8-tetrahydro-2-(2-phenylethyl)chromones with anti-Helicobacter pylori activity from agarwood of Aquilaria sinensis 'Reke 1'","authors":"Ke-Xin Qin , Hao Wang , Li Yang , Yan-Mei Wei , Cai-Hong Cai , Hui-Qin Chen , Wen-Hua Dong , Wei Li , Xian-Yun Yan , Jun Zeng , Wen-Li Mei , Jie Jian , Haofu Dai","doi":"10.1016/j.phytol.2025.01.1002","DOIUrl":"10.1016/j.phytol.2025.01.1002","url":null,"abstract":"<div><div>Two new 5,6,7,8-tetrahydro-2-(2-phenylethyl)chromones (<strong>1</strong> and <strong>2</strong>), together with one known compound (<strong>3</strong>), were isolated from the ethanol extract of agarwood produced from <em>Aquilaria sinensis</em> 'Reke 1'. The structures of compounds <strong>1</strong> and <strong>2</strong> were precisely elucidated on the basis of HR-ESI-MS, 1D and 2D NMR, TDDFT-ECD, as well as by comparison with the literature data. All compounds were evaluated for anti<em>-Helicobacter pylori</em> activity. Compound <strong>2</strong> exhibited significant inhibitory effect against <em>H. pylori</em> with the minimum inhibition concentration (MIC) value of 20 µM.</div></div>","PeriodicalId":20408,"journal":{"name":"Phytochemistry Letters","volume":"66 ","pages":"Pages 77-80"},"PeriodicalIF":1.3,"publicationDate":"2025-02-17","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"143428734","PeriodicalName":null,"FirstCategoryId":null,"ListUrlMain":null,"RegionNum":4,"RegionCategory":"生物学","ArticlePicture":[],"TitleCN":null,"AbstractTextCN":null,"PMCID":"","EPubDate":null,"PubModel":null,"JCR":null,"JCRName":null,"Score":null,"Total":0}
Jia-Jin Liu , Sheng-Run Guo , Hou Zhu, Dan Liu, Hong-Mei Li, Rong-Tao Li
{"title":"Three new maaliane-type sesquiterpenoids from the roots and rhizomes of Valeriana officinalis var. latifolia","authors":"Jia-Jin Liu , Sheng-Run Guo , Hou Zhu, Dan Liu, Hong-Mei Li, Rong-Tao Li","doi":"10.1016/j.phytol.2025.01.996","DOIUrl":"10.1016/j.phytol.2025.01.996","url":null,"abstract":"<div><div>Ten sesquiterpenoids, including three new maaliane-type ones, valeratines A–C (<strong>1</strong>–<strong>3</strong>), were obtained from <em>Valeriana officinalis</em> var. <em>latifolia</em>. By means of extensive spectroscopic analysis, the structures of new compounds were established. Additionally, anti-inflammatory, cytotoxic, together with anti-influenza A virus effects of them were also tested.</div></div>","PeriodicalId":20408,"journal":{"name":"Phytochemistry Letters","volume":"66 ","pages":"Pages 66-69"},"PeriodicalIF":1.3,"publicationDate":"2025-02-17","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"143420547","PeriodicalName":null,"FirstCategoryId":null,"ListUrlMain":null,"RegionNum":4,"RegionCategory":"生物学","ArticlePicture":[],"TitleCN":null,"AbstractTextCN":null,"PMCID":"","EPubDate":null,"PubModel":null,"JCR":null,"JCRName":null,"Score":null,"Total":0}
Xian-Yun Yan , Wei Li , Hao Wang , Wen-Hua Dong , Jun Zeng , Fei Wu , Wen-Li Mei , Lin-Fu Liang , Hao-Fu Dai
{"title":"Three new dimeric 2-(2-phenethyl)chromones from the agarwood of Aquilaria malaccensis","authors":"Xian-Yun Yan , Wei Li , Hao Wang , Wen-Hua Dong , Jun Zeng , Fei Wu , Wen-Li Mei , Lin-Fu Liang , Hao-Fu Dai","doi":"10.1016/j.phytol.2025.02.003","DOIUrl":"10.1016/j.phytol.2025.02.003","url":null,"abstract":"<div><div>Three unreported 2-(2-phenethyl)chromone dimers, malaccenones A–C (<strong>1</strong>–<strong>3</strong>), were isolated and identified from the agarwood <em>Aquilaria malaccensis</em>. These compounds were purified by various column chromatographic techniques, and their structures were elucidated based on the analysis of UV, HRESIMS, 1D and 2D NMR, and ECD spectroscopic data, as well as comparison with literature data. Compounds <strong>1</strong>–<strong>3</strong> were evaluated for their inhibition effects on nitric oxide production in lipopolysaccharide-stimulated RAW264.7 cells. All of these compounds exhibited anti-inflammatory activity with IC<sub>50</sub> values ranging from 21.79 ± 1.05–31.44 ± 1.65 <em>μ</em>M.</div></div>","PeriodicalId":20408,"journal":{"name":"Phytochemistry Letters","volume":"66 ","pages":"Pages 81-85"},"PeriodicalIF":1.3,"publicationDate":"2025-02-17","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"143428736","PeriodicalName":null,"FirstCategoryId":null,"ListUrlMain":null,"RegionNum":4,"RegionCategory":"生物学","ArticlePicture":[],"TitleCN":null,"AbstractTextCN":null,"PMCID":"","EPubDate":null,"PubModel":null,"JCR":null,"JCRName":null,"Score":null,"Total":0}
Wen Wen , Delan Yang , Hao Wang , Huiqin Chen , Yanbo Zeng
{"title":"Anti-inflammatory steroids from the soft coral Cladiella sp.","authors":"Wen Wen , Delan Yang , Hao Wang , Huiqin Chen , Yanbo Zeng","doi":"10.1016/j.phytol.2025.02.006","DOIUrl":"10.1016/j.phytol.2025.02.006","url":null,"abstract":"<div><div>A new undescribed steroid 23,24-epoxy-24-methylchol-5-ene-3<em>β</em>-ol (<strong>1</strong>), together with two known steroids (24<em>S</em>)-24-methylcholest-5-ene-3<em>β</em>,25-diol (<strong>2</strong>) and 16-hydroxysarcosterol (<strong>3</strong>) was extracted from the soft coral <em>Cladiella</em> sp. Their structures were investigated by IR, MS, 1D and 2D NMR spectra, while QM-NMR calculations were utilized to ascertain the configuration of compound <strong>1</strong>. The potential anti-inflammatory properties of all compounds were assessed. Compound <strong>1</strong> exerted a moderate suppressive effect on LPS-stimulated inflammatory reactions in RAW264.7 macrophage cells, with IC<sub>50</sub> value of 32.93 ± 2.32 <em>μ</em>M. Compounds <strong>2</strong> and <strong>3</strong> demonstrated weaker inhibitory effects, with IC<sub>50</sub> values of 80.05 ± 7.11 and 54.05 ± 2.82 <em>μ</em>M, respectively.</div></div>","PeriodicalId":20408,"journal":{"name":"Phytochemistry Letters","volume":"66 ","pages":"Pages 70-76"},"PeriodicalIF":1.3,"publicationDate":"2025-02-17","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"143428735","PeriodicalName":null,"FirstCategoryId":null,"ListUrlMain":null,"RegionNum":4,"RegionCategory":"生物学","ArticlePicture":[],"TitleCN":null,"AbstractTextCN":null,"PMCID":"","EPubDate":null,"PubModel":null,"JCR":null,"JCRName":null,"Score":null,"Total":0}
Xiaoran Min , Junping Chen , Wenhao Mu , Jiayi Huang , Guozheng Huang , Jianguo Cao
{"title":"A new dimeric sesquiterpenoid from Ajania fruticulosa","authors":"Xiaoran Min , Junping Chen , Wenhao Mu , Jiayi Huang , Guozheng Huang , Jianguo Cao","doi":"10.1016/j.phytol.2025.02.001","DOIUrl":"10.1016/j.phytol.2025.02.001","url":null,"abstract":"<div><div>One new sesquiterpenoid (<strong>1</strong>) and eighteen known natural compounds (<strong>2–19</strong>) were obtained from the aerial parts of <em>Ajania fruticulosa</em>. Their structures were established by spectroscopic methods, and the absolute configurations were further determined by single-crystal X-ray diffraction analysis for compounds <strong>1</strong> and <strong>3</strong>. Compound <strong>1</strong> is a guaianolide-type dimeric sesquiterpenoid which might be a product of [4 + 2] addition reaction between compound <strong>3</strong> and its 1,2-dehydro analogue. Compound <strong>12</strong> showed a potent xanthine oxidase (XOD) inhibitory activity (IC<sub>50</sub> value of 23.82 ± 0.35 μM) and acted as a mixed-type inhibitor of XOD. Compounds <strong>12</strong> and <strong>13</strong> showed low toxicity while significantly inhibiting LPS-induced NO production in RAW264.7 cells.</div></div>","PeriodicalId":20408,"journal":{"name":"Phytochemistry Letters","volume":"66 ","pages":"Pages 60-65"},"PeriodicalIF":1.3,"publicationDate":"2025-02-16","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"143419305","PeriodicalName":null,"FirstCategoryId":null,"ListUrlMain":null,"RegionNum":4,"RegionCategory":"生物学","ArticlePicture":[],"TitleCN":null,"AbstractTextCN":null,"PMCID":"","EPubDate":null,"PubModel":null,"JCR":null,"JCRName":null,"Score":null,"Total":0}
{"title":"Synthesis of formononetin derivatives and their neuroprotective activities","authors":"Zeping Luo, Liwei Pan","doi":"10.1016/j.phytol.2025.01.999","DOIUrl":"10.1016/j.phytol.2025.01.999","url":null,"abstract":"<div><div>To develop a series of derivatives (C1–14) of Formononetin (FMN) and evaluate their neuroprotective effects and potential mechanisms in N2a/APP695 cells. The levels of Aβ1–42 were quantified using ELISA, while mitochondrial membrane potential and ROS content were assessed via JC-1 and DCFH-DA methods, respectively. Additionally, mitochondrial function was evaluated by measuring ATP levels. Protein expressions of PINK1, Parkin, p62, LC3, and p-Tau S396 were analyzed using Western blotting. The results showed that compared to the control group, C1–14 significantly reduced the level of Aβ1–42, with C7 exhibiting the most pronounced effect. Further investigation revealed that C7 improved mitochondrial function, upregulated the expression of PINK1, Parkin, and LC3, and downregulated the levels of p62 and p-Tau S396. The results indicate that C7 demonstrates a neuroprotective effect by activating mitochondrial autophagy, optimizing mitochondrial function, and inhibiting the accumulation of Aβ1–42 and p-Tau S396 in nerve cells. This is achieved through the promotion of mitochondrial autophagy-related proteins PINK1 and Parkin. Thus, C7 represents a promising candidate for the prevention and treatment of AD, offering a novel therapeutic strategy</div></div>","PeriodicalId":20408,"journal":{"name":"Phytochemistry Letters","volume":"66 ","pages":"Pages 39-48"},"PeriodicalIF":1.3,"publicationDate":"2025-02-15","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"143420545","PeriodicalName":null,"FirstCategoryId":null,"ListUrlMain":null,"RegionNum":4,"RegionCategory":"生物学","ArticlePicture":[],"TitleCN":null,"AbstractTextCN":null,"PMCID":"","EPubDate":null,"PubModel":null,"JCR":null,"JCRName":null,"Score":null,"Total":0}
{"title":"Structural determination of two undescribed triterpenoids from Punica granatum L. peels","authors":"Tomoki Iguchi, Norika Shibata, Hiyoka Ito, Tamami Shimazaki, Yoshihiro Mimaki","doi":"10.1016/j.phytol.2025.02.005","DOIUrl":"10.1016/j.phytol.2025.02.005","url":null,"abstract":"<div><div>Seven triterpenoids (<strong>1</strong>–<strong>7</strong>) comprising four oleanane-type (<strong>1</strong>–<strong>4</strong>), two ursane-type (<strong>5</strong> and <strong>6</strong>), and one lupane-type (<strong>7</strong>), were isolated from <em>Punica granatum</em> L. peels. The structures of two undescribed compounds (<strong>1</strong> and <strong>2</strong>) were elucidated primarily by two-dimensional NMR spectroscopic analysis. This is the first reported isolation of <strong>3</strong>, <strong>6</strong>, and <strong>7</strong> from <em>P. granatum</em>. The cytotoxicity of <strong>1</strong>–<strong>7</strong> was evaluated in SBC-3 human small-cell lung cancer cells using a modified 3-(4,5-dimethylthiazol-2-yl)-2,5-diphenyl-2-tetrazolium bromide assay. Compounds <strong>3</strong>–<strong>7</strong> exhibited moderate cytotoxicity against SBC-3 cells, with IC<sub>50</sub> values ranging from 52 to 61 μM.</div></div>","PeriodicalId":20408,"journal":{"name":"Phytochemistry Letters","volume":"66 ","pages":"Pages 54-59"},"PeriodicalIF":1.3,"publicationDate":"2025-02-15","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"143420601","PeriodicalName":null,"FirstCategoryId":null,"ListUrlMain":null,"RegionNum":4,"RegionCategory":"生物学","ArticlePicture":[],"TitleCN":null,"AbstractTextCN":null,"PMCID":"","EPubDate":null,"PubModel":null,"JCR":null,"JCRName":null,"Score":null,"Total":0}
Christina Barda , Maria-Eleni Grafakou , Joerg Heilmann , Helen Skaltsa
{"title":"Exploring the phytochemical composition of Crepis heldreichiana (Kuntze) Greuter: A unique endemic species of Greece","authors":"Christina Barda , Maria-Eleni Grafakou , Joerg Heilmann , Helen Skaltsa","doi":"10.1016/j.phytol.2025.01.1003","DOIUrl":"10.1016/j.phytol.2025.01.1003","url":null,"abstract":"<div><div>Within the genus <em>Crepis</em> of the Asteraceae family (Cichorieae), <em>Crepis heldreichiana</em> (Kuntze) Greuter is recognized as a native plant in the Greek flora, with a distribution limited to the Taigetos and Parnonas mountains of the Peloponnese.</div><div>Taking into consideration the restricted geographic range and the unexplored chemical profile of <em>C</em>. <em>heldreichiana</em>. This study was designed to unveil its phytochemical profile revealing 13 compounds, among which four are identified as sesquiterpene lactones, including a previously unreported one, as well as an apocaroteonoid, while the remaining are primarily phenolic derivatives.</div><div>Various spectrometric and spectroscopic techniques were employed to elucidate the structures of the isolated compounds. The relative configurations of the compounds were established through analysis of NMR spectroscopic and HRESIMS spectrometric data, complemented by CD spectroscopic measurements.</div></div>","PeriodicalId":20408,"journal":{"name":"Phytochemistry Letters","volume":"66 ","pages":"Pages 49-53"},"PeriodicalIF":1.3,"publicationDate":"2025-02-15","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"143420546","PeriodicalName":null,"FirstCategoryId":null,"ListUrlMain":null,"RegionNum":4,"RegionCategory":"生物学","ArticlePicture":[],"TitleCN":null,"AbstractTextCN":null,"PMCID":"","EPubDate":null,"PubModel":null,"JCR":null,"JCRName":null,"Score":null,"Total":0}