Phytochemistry Letters最新文献

{"title":"Acylphloroglucinol derivatives from the aerial parts of Syzygium borneense and their cytotoxic activities","authors":"Thi Van Nguyen ,&nbsp;Thi Quynh Do ,&nbsp;Marc Litaudon ,&nbsp;Thuy Linh Nguyen ,&nbsp;Van Nam Vu ,&nbsp;Thu Huong Tran ,&nbsp;Thi Mai Huong Doan ,&nbsp;Van Cuong Pham","doi":"10.1016/j.phytol.2024.07.006","DOIUrl":"10.1016/j.phytol.2024.07.006","url":null,"abstract":"<div><p>Four new acylphloroglucinol derivatives, borneensinones A-D (<strong>1–4</strong>) along with five known compounds (<strong>5</strong>-<strong>9</strong>) were isolated from the aerial parts of <em>Syzygium borneense.</em> Their structures were elucidated based on the interpretation of spectrometric and spectroscopic data (HRESI-MS, 1D- and 2D-NMR) and by comparison with literature data for known compounds. All acylphloroglucinol derivatives (<strong>1–6)</strong> were tested for their cytotoxic activities against four human cancer cell lines (KB, MCF-7, HepG-2, and A549). Among the six tested compounds, compound <strong>6</strong> exhibited the strongest inhibitory activity against four tested cancer cell lines, with IC₅₀ values ranging from 6.21 to 26.96 μM. Compound <strong>1</strong> was more active against KB and HepG2 comparing to the A549 and MCF7 cells. Compound <strong>5</strong> had a moderate cytotoxicity with IC₅₀ values ranging from 27.71 to 97.32 μM.</p></div>","PeriodicalId":20408,"journal":{"name":"Phytochemistry Letters","volume":"62 ","pages":"Pages 78-83"},"PeriodicalIF":1.3,"publicationDate":"2024-07-18","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"141638020","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":"Alliaceumolide A: A rare undescribed 17-membered macrolide from Indonesian Dysoxylum alliaceum","authors":"Sandra Amalia Riyadi ,&nbsp;Al Arofatus Naini ,&nbsp;Tri Mayanti ,&nbsp;Kindi Farabi ,&nbsp;Desi Harneti ,&nbsp;Nurlelasari ,&nbsp;Rani Maharani ,&nbsp;Ronny Lesmana ,&nbsp;Sofa Fajriah ,&nbsp;Siriporn Jungsuttiwong ,&nbsp;Khalijah Awang ,&nbsp;Mohamad Nurul Azmi ,&nbsp;Unang Supratman","doi":"10.1016/j.phytol.2024.07.004","DOIUrl":"10.1016/j.phytol.2024.07.004","url":null,"abstract":"<div><p>Alliaceumolide A (<strong>1</strong>), a new macrolide together with known ivorenolide B (<strong>2</strong>) were isolated from <em>Dysoxylum alliaceum</em> (Blume) Blume ex A.Juss. These compounds were classified as 17-membered macrolide, which is a rare structure for plant-derived natural products. The structures were elucidated by extensive spectroscopic analyses, and the absolute configuration of <strong>1</strong> was determined by electronic circular dichroism (ECD) using TDDFT method. Furthermore, compounds <strong>1</strong> and <strong>2</strong> were tested for cytotoxic activity against two cancer MCF-7 and HeLa cell lines.</p></div>","PeriodicalId":20408,"journal":{"name":"Phytochemistry Letters","volume":"62 ","pages":"Pages 73-77"},"PeriodicalIF":1.3,"publicationDate":"2024-07-17","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"141638022","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":"The influence of complex compounds of zinc, copper and platinum on germination, growth and amount of secondary metabolites of alfalfa (Medicago sativa L.)","authors":"Bojana Veljković ,&nbsp;Andrija Ćirić ,&nbsp;Tanja Soldatović","doi":"10.1016/j.phytol.2024.07.002","DOIUrl":"https://doi.org/10.1016/j.phytol.2024.07.002","url":null,"abstract":"<div><p><em>Medicago sativa</em> L. (alfalfa) is a herbaceous plant of great importance in agriculture. The chemical composition of the substrate affects the mineral supply as well as the growth, development and metabolism of the plants. Therefore, the aim of this experiment is to determine the influence of zinc, copper and platinum complexes ([ZnCl₂(en)], [CuCl₂(en)], <em>cis</em>-[PtCl₂(NH₃)₂], en = ethylenediamine) on the germination and growth of alfalfa and on the content of phenolic compounds. Alfalfa seeds were sown in three separate groups and treated with the above complexes, the fourth group being the control. The growth of the vegetative part was observed after the tenth, twentieth and thirtieth day. The percentage of germination was recorded for each experimental group. At the end of the treatment, the aerial parts of each group were dried and prepared for extraction with methanol, after which the quantitative composition of phenolic compounds was analyzed by liquid chromatography.The results obtained show that [CuCl₂(en)] has the best effect on the germination percentage, while the treatment with the platinum(II) complex - <em>cis</em>-[PtCl₂(NH₃)₂] showed a significant effect on the growth of alfalfa. The results of chromatographic analysis showed that [ZnCl₂(en)] and [CuCl₂(en)] improved the synthesis of phenolic compounds of alfalfa, with a significant content of catechins in the treatment with the copper complex compared to the control group. Based on the obtained results, it was concluded that the complex compounds have a significant effect on the germination, growth and phenolic compounds content of alfalfa, with different effects for each of the studied processes.</p></div>","PeriodicalId":20408,"journal":{"name":"Phytochemistry Letters","volume":"62 ","pages":"Pages 68-72"},"PeriodicalIF":1.3,"publicationDate":"2024-07-13","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"141606183","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":"Design, isolation, synthesis, and mechanistic insight of flavonoids isolated from Beilschmiedia obscura, as potential α-glucosidase inhibitors","authors":"Suzanne L. Nyemeck ,&nbsp;Kenneth O. Eyong ,&nbsp;Ronald Bidingha ,&nbsp;Michael HK. Kamdem ,&nbsp;Derek T. Ndinteh ,&nbsp;Patricia O. Odumosu ,&nbsp;Gabriel N. Folefoc ,&nbsp;Danielle C. Bilanda ,&nbsp;Andrew E. Egbe ,&nbsp;Thomas Werner ,&nbsp;Boris D. Bekono ,&nbsp;Fidele Ntie-Kang","doi":"10.1016/j.phytol.2024.06.004","DOIUrl":"https://doi.org/10.1016/j.phytol.2024.06.004","url":null,"abstract":"<div><p>Flavonoids based on the flavone <strong>1–</strong>3 and a biflavanoid <strong>4</strong> with a flavan nucleus were isolated from <em>Beilschmiedia obscura</em> (Stapf). These compounds which include 5- hydroxy - 7,8-dimethoxyflavanone (<strong>5</strong>), (<em>2 S,4 R</em>)-5, 6,7-trimethoxyflavan-4-ol (<strong>6</strong>), beilschmieflavonoid B (<strong>7</strong>), (2 <em>R</em>,3 <em>S</em>)-5,6,7-trimethoxyflavan-3-ol (<strong>8</strong>), as well as pipyahyine (<strong>9</strong>), (<em>E</em>,<em>E</em>)-1,6-bis(4-hydroxy-3-methoxyphenyl) hexa-1,5-diene-3,4-dione (<strong>10</strong>), β-sitosterol (<strong>11</strong>), pentadecanoic acid (<strong>12</strong>), pentadecan-1-ol (<strong>13</strong>), stearic acid (<strong>14</strong>) and docosane-1,2,4-triol (<strong>15</strong>), were evaluated as α-glucosidase inhibitors. The most abundant compound <strong>5</strong>, was structurally modified by acetylation to compound <strong>16</strong> and NaBH₄ reduction to compound <strong>17</strong> which represent two new derivatives of this compound class. These compounds <strong>5–10</strong>, <strong>16–17</strong> including kaempferol <strong>18</strong>, and epicatechin <strong>19</strong> were screened for α-glucosidase from <em>Bacillus stearothermophyllus</em> and showed good inhibitory activity with IC₅₀ values = (30.55±0.12, 31.8±0.12, 32.47±0.17, 46.53±0.16, 36.43±0.12, 33, 48±0,12, 32.63±0.11 and 43.31±0.12 µM respectively) compared to acarbose (IC₅₀ = 63.77±0.08 µM) as reference drug. Molecular docking and SAR studies further confirmed the plausible binding interactions between the flavonoids and the enzyme α-glucosidase. The results show that these compounds bind effectively to the active site of the protein X-ray structure 3wy1, which is in accordance of the observed α-glucosidase inhibitory activity.</p></div>","PeriodicalId":20408,"journal":{"name":"Phytochemistry Letters","volume":"62 ","pages":"Pages 59-67"},"PeriodicalIF":1.3,"publicationDate":"2024-07-08","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"141583263","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":"Three new chemical constituents of Senecio raphanifolius","authors":"Shu-Wen Huang ,&nbsp;Huan He ,&nbsp;Zhi-Qiang Li ,&nbsp;Yu-Wei Wang ,&nbsp;Yuan-Ying Fang ,&nbsp;Yu-Lin Feng ,&nbsp;Zhi-Feng Li ,&nbsp;Qi Wang","doi":"10.1016/j.phytol.2024.07.003","DOIUrl":"https://doi.org/10.1016/j.phytol.2024.07.003","url":null,"abstract":"<div><p>Three new constituents, 4a-hydroxy-1-methyl-4,4a,8,8a-tetrahydro-1 H-isochromene-3,7-dione (<strong>1</strong>), 1-(2-(prop-1-en-2-yl)-3-((3,4,5-trihydroxy-6-(hydroxymethyl)tetrahydro-2 H-pyran-2-yl)oxy)-2,3-dihydrobenzofuran-5-yl)ethan-1-one (<strong>2</strong>), and 5-(hydroxymethyl)-2,3-dihydro-1 H-pyrrolizin-1-one (<strong>3</strong>), together with 3 known flavonoids (<strong>4</strong>-<strong>6</strong>), 6 organic acids (<strong>7</strong>-<strong>12</strong>), 1 glycoside (<strong>13</strong>), and 2 terpenoids (<strong>14</strong>-<strong>15</strong>) were isolated from the 50 % ethanol extract of the whole plant of <em>Senecio raphanifolius</em> Wall. ex DC. The structures of these novel compounds were determined using high-resolution electrospray ionization–mass spectrometry and NMR, mainly using 2D NMR. The anti-inflammatory activities of compounds <strong>1</strong>-<strong>3</strong> were evaluated based on their ability to inhibit nitric oxide (NO) production in lipopolysaccharide-stimulated RAW264.7 cells. Compound <strong>1</strong> could reduce NO levels and had an inhibition rate of 42.86 % at 100 µM.</p></div>","PeriodicalId":20408,"journal":{"name":"Phytochemistry Letters","volume":"62 ","pages":"Pages 53-58"},"PeriodicalIF":1.3,"publicationDate":"2024-07-08","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"141583346","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":"New cassane diterpenoids from the seeds of Pterolobium macropterum","authors":"Yue-ping Lan,&nbsp;Wen-jian Gu,&nbsp;Ming Yang,&nbsp;Pu-Zhao Zhang","doi":"10.1016/j.phytol.2024.06.008","DOIUrl":"https://doi.org/10.1016/j.phytol.2024.06.008","url":null,"abstract":"<div><p>Three undescribed cassane diterpenoids were isolated from the seeds of <em>Pterolobium macropterum</em>. The structures of these compounds were elucidated based on the extensive spectroscopic techniques. All isolated compounds were evaluated for their efficacy on the lipopolysaccharide induced nitric oxide (NO) production in BV-2 microglial cells. Compound <strong>1</strong> could significantly inhibited the production of NO with IC₅₀ value of 7.18 ± 0.40 <em>μ</em>M.</p></div>","PeriodicalId":20408,"journal":{"name":"Phytochemistry Letters","volume":"62 ","pages":"Pages 44-48"},"PeriodicalIF":1.3,"publicationDate":"2024-07-06","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"141583344","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":"Primary and secondary metabolites from the soil-root interaction in the rhizosphere facilitates extreme water depletion tolerance in olive trees","authors":"Beligh Mechri ,&nbsp;Meriem Tekaya ,&nbsp;Ahlem Guesmi ,&nbsp;Ammar Houas ,&nbsp;Mohamed Hammami ,&nbsp;Naoufel Ben Hamadi ,&nbsp;Hechmi Chehab","doi":"10.1016/j.phytol.2024.06.009","DOIUrl":"https://doi.org/10.1016/j.phytol.2024.06.009","url":null,"abstract":"<div><p>Water is vital for all living rhizospheric organisms. However, numerous microorganisms have adapted to survive in environments in which water is scarce. Recent evidence has indicated that sugars from root or microbial source is linked with water deficit tolerance of crops. Here we described in olive trees the changes in sugars accumulation in roots, in combination with corresponding changes in microbial and soluble sugar profiles in the rhizosphere under drought conditions. A marked increase in mannitol content occurred in roots of water-stressed plants. Application of drought stress caused a significant increase in the level of microbial trehalose when compared to the control. Trehalose may increase the soil water surface tension, which could facilitate drought tolerance of olive. We showed that complex interactions of root and microbial community in the rhizosphere maintained the relative water content at 60 % under drought conditions and have the potential to regulate the water uptake by olive.</p></div>","PeriodicalId":20408,"journal":{"name":"Phytochemistry Letters","volume":"62 ","pages":"Pages 49-52"},"PeriodicalIF":1.3,"publicationDate":"2024-07-06","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"141583345","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":"Dimeric piperidinoquinoline alkaloids from the seeds of Chimonanthus salicifolius","authors":"Zhan-Peng Yu ,&nbsp;Yu-Xia Wang ,&nbsp;Li-Hong Hong ,&nbsp;Ya-Lin Li ,&nbsp;Jian-Fei Zhang ,&nbsp;Mu Li ,&nbsp;Ping Ying ,&nbsp;Qiang Zheng ,&nbsp;Ling-Yi Kong ,&nbsp;Jian-Guang Luo","doi":"10.1016/j.phytol.2024.07.001","DOIUrl":"https://doi.org/10.1016/j.phytol.2024.07.001","url":null,"abstract":"<div><p>A chemical investigation of extracts from the seeds of <em>Chimonanthus salicifolius</em> has led to the isolation of four new dimeric piperidinoquinoline alkaloids (<strong>1</strong>-<strong>4</strong>) and one new dimeric tryptamine alkaloid (<strong>5</strong>), along with five known alkaloids (<strong>6</strong>-<strong>10</strong>). Notably, compounds <strong>3</strong> and <strong>4</strong> were identified as two unusual dimeric piperidinoquinoline alkaloid-fatty acid hybrids. The new structures were elucidated using HRESIMS, NMR, and ECD spectroscopic techniques. The isolated compounds were subjected to cytotoxicity testing against HCT-116, HT-1080, and A549 cell lines. Compound <strong>5</strong> exhibited moderate activity against the HCT-116 and HT-1080 cell lines, with IC₅₀ values of 44.59 ± 2.08 <em>μ</em>M and 37.39 ± 2.31 <em>μ</em>M, respectively.</p></div>","PeriodicalId":20408,"journal":{"name":"Phytochemistry Letters","volume":"62 ","pages":"Pages 38-43"},"PeriodicalIF":1.3,"publicationDate":"2024-07-04","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"141540919","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":"Maytenhoiridosides A and B, two new iridoid glycosides from the branches of Maytenus hookeri","authors":"Huijing Lv ,&nbsp;Qinghong Kong ,&nbsp;Changwei Song ,&nbsp;Jiawei Yang ,&nbsp;Lingjie Meng","doi":"10.1016/j.phytol.2024.06.007","DOIUrl":"https://doi.org/10.1016/j.phytol.2024.06.007","url":null,"abstract":"<div><p>Two new iridoid glycosides, maytenhoiridosides A (<strong>1</strong>) and maytenhoiridosides B (<strong>2</strong>), along with three known compounds (<strong>3</strong>–<strong>5</strong>), were isolated from the branches of <em>Maytenus hookeri</em>. Their chemical structures were elucidated by HR-ESI-MS, 1D and 2D-NMR spectra, acid hydrolysis analysis, and comparison with literature data. Among the isolated compounds, compound <strong>5</strong> exhibited significant cytotoxic activity against the HCT-116, SKOV3 and SK-Hep-1 cells, with IC₅₀ values of 9.49±1.40, 34.66±1.48 and 12.66±3.32 µM, respectively, while the others showed weak or no activity at 50 μM.</p></div>","PeriodicalId":20408,"journal":{"name":"Phytochemistry Letters","volume":"62 ","pages":"Pages 34-37"},"PeriodicalIF":1.3,"publicationDate":"2024-07-01","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"141482060","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":"New antibacterial penicimenolide G with unusual 12-membered resorcylic acid lactone ring isolated from endophytic fungus Aspergillus giganteus","authors":"Abul Hasnat Md Shamim ,&nbsp;Md Abdul Mojid Mondol ,&nbsp;Miraj Hossain ,&nbsp;Tanvir Islam Shovo ,&nbsp;Minhaz Uddin ,&nbsp;Mohammad Nur-e-Alam ,&nbsp;Iftekhar Alam ,&nbsp;Hattan A. Alharbi ,&nbsp;A.F.M. Motiur Rahman","doi":"10.1016/j.phytol.2024.06.003","DOIUrl":"https://doi.org/10.1016/j.phytol.2024.06.003","url":null,"abstract":"<div><p>Current antibiotics are increasingly losing their effectiveness against multidrug-resistant pathogenic bacteria, necessitating the search for new antibiotics. Endophytic fungi are widely recognized as valuable sources of structurally novel secondary metabolites with diverse biological activities. In this study, an endophytic fungus, designated KRL01, was isolated from a leaf of <em>Capparis carandas</em>. The strain was identified as <em>Aspergillus giganteus</em> through analysis of its internal transcribed spacer (ITS) rDNA sequence. Subsequently, the fungus was cultured in a rice medium and extracted using ethyl acetate. A novel metabolite, named penicimenolide G (<strong>1</strong>), was isolated from the extract using chromatography. Compound <strong>1</strong> demonstrated potent antibacterial activity against both Gram-positive and Gram-negative bacterial strains, including those resistant to the standard antibiotic amoxicillin.</p></div>","PeriodicalId":20408,"journal":{"name":"Phytochemistry Letters","volume":"62 ","pages":"Pages 18-23"},"PeriodicalIF":1.3,"publicationDate":"2024-06-24","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"141482058","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}