Phytochemistry Letters最新文献

{"title":"Molecular docking studies and in-vitro cholinesterase inhibitory activities of chemical constituents of Calophyllum gracilentum","authors":"Nurr Maria Ulfa Seruji ,&nbsp;Vivien Yi Mian Jong ,&nbsp;Thiruventhan Karunakaran ,&nbsp;Nor Hisam Zamakshshari ,&nbsp;Siau Hui Mah ,&nbsp;Natalie Vivien Gunter ,&nbsp;Mas Atikah Lizazman ,&nbsp;Arai Masayoshi","doi":"10.1016/j.phytol.2024.08.007","DOIUrl":"10.1016/j.phytol.2024.08.007","url":null,"abstract":"<div><p><em>Calophyllum</em> species are well known due to their abundance of potentially beneficial phytochemicals, such as xanthones, coumarins, and others. However, <em>Calophyllum gracilentum</em> is an understudied specie with very limited information. Medicinal plants have been proven to have therapeutic potential in managing neurological disorders associated with acetylcholinesterase (AChE) dysregulation. Still, there has been little investigation on <em>Calophyllum</em> plants for this purpose. Herein, we report on the isolation of a new oxygenated xanthone 5,10-dihydroxy-9-methoxy-2,2-dimethyl-12-(3-methylbut-2-enyl) pyrano[3,2-<em>b</em>] xanthen-6(2 H)-one (<strong>1</strong>) and eleven known xanthones (<strong>2–12</strong>), three chromanone acids (<strong>13–15</strong>), and phytosterols (<strong>16–18</strong>), respectively from the stem bark of the <em>Calophyllum gracilentum.</em> The evaluation of AChE inhibitory activity showed that all the extracts and xanthones (<strong>2</strong>, <strong>5</strong>, <strong>6</strong>, <strong>8</strong>, <strong>9</strong>, <strong>12</strong>) tested have potential AChE inhibitory activity. Compounds (<strong>5</strong>) and (<strong>12</strong>) are prospective AChE inhibitors with IC₅₀ values of 1.8 ± 0.0001 and 4.0 ± 0.0002 µmol/L. The molecular docking analysis demonstrated compound (<strong>5</strong>) and compound (<strong>12</strong>) bind well to the active site which is the anionic site containing Trp 84 and Asp 72 in the of <em>Torpedo californica</em> acetylcholinesterase (TcAChE) through π-π stacking, hydrogen bonding, and π-donor hydrogen bond from the xanthone ring, besides π-alkyl and π-σ interactions from the substituent group with the binding energy of −11.1 kcal/mol for compound (<strong>5</strong>) and binding energy of −10.4 kcal/mol for compound (<strong>12</strong>).</p></div>","PeriodicalId":20408,"journal":{"name":"Phytochemistry Letters","volume":"63 ","pages":"Pages 93-100"},"PeriodicalIF":1.3,"publicationDate":"2024-08-22","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"142040961","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":"An alternative fate of taraxasteryl cation in young shoots of Rosa multiflora: Deprotonation of H-19 produces taraxast-19-en-3β-ol and related triterpenoids","authors":"Marika Furuya,&nbsp;Taichi Akano,&nbsp;Hiroshi Araya,&nbsp;Yoshinori Fujimoto","doi":"10.1016/j.phytol.2024.08.006","DOIUrl":"10.1016/j.phytol.2024.08.006","url":null,"abstract":"<div><p>Taraxast-19-en-3β-ol (<strong>1</strong>) and taraxast-19-en-3-one (<strong>2</strong>) were isolated from the surface lipids of young shoots of <em>Rosa multiflora</em> Thunb. The results provide the first evidence that deprotonation of H-19 can occur to produce the tetra-substituted triterpenes, in addition to the known formation taraxasterol and ϕ-taraxasterol by deprotonation of H-30 and H-21, respectively. Furthermore, taraxast-19(29)-ene-3β,20α-diol (<strong>3</strong>), which is presumed to be formed from compound <strong>1</strong> was isolated. The structures of the new compounds <strong>1</strong>-<strong>3</strong> with the α-orientation of H-18 were determined by spectroscopic methods including NOE studies. In addition, 19,20-seco-3β-hydroxyursane-19,20-dione (<strong>4</strong>), a 3β-hydroxy analog of the known 19,20-seco-ursane-3,19,20-trione was isolated. It is of note that compound <strong>4</strong> has the β-orientation of H-18, which is opposite to the α-orientation of H-18 of compounds <strong>1</strong>-<strong>3</strong>.</p></div>","PeriodicalId":20408,"journal":{"name":"Phytochemistry Letters","volume":"63 ","pages":"Pages 87-92"},"PeriodicalIF":1.3,"publicationDate":"2024-08-21","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"142020816","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":"Steroids and Epicoccarines from Penicillium aurantiancobrunneum","authors":"Charmaine A. Lindsay ,&nbsp;Choon Y. Tan ,&nbsp;Deepa Krishnan ,&nbsp;Dmitriy Uchenik ,&nbsp;Gerardo D. Anaya Eugenio ,&nbsp;Eric D. Salinas ,&nbsp;Esperanza J. Carcache de Blanco ,&nbsp;A. Douglas Kinghorn ,&nbsp;Harinantenaina L. Rakotondraibe","doi":"10.1016/j.phytol.2024.08.008","DOIUrl":"10.1016/j.phytol.2024.08.008","url":null,"abstract":"<div><p>Lichens are symbiotic organisms comprised of mycobionts and photobiont partners. They are known to produce bioactive secondary metabolites and most of these are biosynthesized by mycobionts. Investigations of cultures of isolated lichen-associated fungi have shown promise for the discovery of cytotoxic compounds. Thus, the lichen-associated fungus <em>Penicillium aurantiacobrunneum</em> was studied for its potential to produce novel compounds and the new sterols (20 <em>S</em>*)-hydroxy-24(28)-dehydrocampesterol (<strong>1</strong>), 7α-methoxy-8β-hydroxypaxisterol (<strong>2</strong>), 14-<em>nor</em>-epicoccarine A (<strong>3</strong>) and 14-<em>nor</em>-epicoccarine B (<strong>4</strong>), as well as the known compound PF1140 (<strong>5</strong>), were isolated. The structures of these compounds were elucidated using methods including nuclear magnetic resonance (NMR) spectroscopy and high-resolution electrospray ionization mass spectrometry (HRESIMS). Following cytotoxicity assays, compound <strong>1</strong> demonstrated activity against the pancreatic adenocarcinoma epithelial HPAC cell line at 17.76 ± 5.35 μM. Since the structures of compounds <strong>3</strong> and <strong>4</strong> were very similar to tetramic acid derivatives that were reported to be biosynthesized from a polyketide synthase- non-ribosomal peptide synthetase (PKS-NRPS) hybrid pathway, a plausible biosynthetic route for production in <em>P. aurantiacobrunneum</em> is proposed herein.</p></div>","PeriodicalId":20408,"journal":{"name":"Phytochemistry Letters","volume":"63 ","pages":"Pages 79-86"},"PeriodicalIF":1.3,"publicationDate":"2024-08-16","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"141997811","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":"Biodiversity and emergence of viral pandemics","authors":"Bruno David","doi":"10.1016/j.phytol.2024.08.001","DOIUrl":"10.1016/j.phytol.2024.08.001","url":null,"abstract":"<div><p>Phytochemists are aware of the contribution of plant biodiversity in providing chemical entities to the therapeutic arsenal, but the links between biodiversity and the emergence of pandemics are less described. \"Healthy\" biodiverse ecosystems protect us humans against emergence of infectious diseases and transmission as exemplified by the \"dilution effect\" developed upon the eco-epidemiological tick-borne Lyme disease. The emergence and spread of viral pandemics is not only due to the degradation of biodiversity but also compounded by anthropogenic factors such as the intensification and acceleration of trade and intercontinental transport, unprecedented urban human concentrations, climate change, industrialisation, massification and genetic uniformity in industrial breeding, consumption of bushmeat and promiscuity in certain markets with living animals. \"One-Health\" holistic approach to sustainable development is an excellent option to reduce the emergence of future pandemics. It tackles global environmental, human and animal health issues while respecting climate and ecological climate objectives. Surprisingly, this type of strategy implies accepting parasites and viruses and not seeing them as enemies to be eliminated. It also calls for recognition of the role of the local and indigenous communities in taking care traditionally and sustainably of more than a quarter of the world's land area. Only by thinking globally and acting locally this way, we will be able to reduce the risk of (re)-emergences of zoonoses and parasitic diseases.</p></div>","PeriodicalId":20408,"journal":{"name":"Phytochemistry Letters","volume":"63 ","pages":"Pages 69-78"},"PeriodicalIF":1.3,"publicationDate":"2024-08-13","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"141978994","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":"Inulabritanthymols A and B, thymols from Inula britannica and their anti-inflammatory effects","authors":"Rong Bai ,&nbsp;Xiucong Fan ,&nbsp;Fang Fang ,&nbsp;Dan Qiao ,&nbsp;Juan Zhang","doi":"10.1016/j.phytol.2024.07.014","DOIUrl":"10.1016/j.phytol.2024.07.014","url":null,"abstract":"<div><p><em>Inula britannica</em> is a traditional Chinese medicine that possesses various pharmacological effects, including expectorant, cough suppressant, and antibacterial effects. Phytochemical investigation of <em>I. britannica</em> resulted in the isolation of a pair of novel thymols, (8 <em>S</em>,9 <em>S</em>)-inulabritanthymol A (<strong>1a</strong>) and (8 <em>R</em>,9 <em>R</em>)-inulabritanthymol A (<strong>1b</strong>), and a new thymol inulabritanthymol B (<strong>2</strong>) as well as five known thymols (<strong>3</strong>−<strong>7</strong>). Their structures were characterized using 1D and 2D NMR, HRMS, and electronic circular dichroism (ECD) spectra, and quantum chemical calculations. Compounds <strong>5</strong>–<strong>7</strong> showed inhibitory potentials toward NO production, and their IC₅₀ values were 6.39, 5.80, and 8.53 μM, respectively. Molecular docking indicated the interaction of compound <strong>6</strong> with iNOS. These findings demonstrated that thymols served as potential candidates for developing anti-inflammatory drugs.</p></div>","PeriodicalId":20408,"journal":{"name":"Phytochemistry Letters","volume":"63 ","pages":"Pages 64-68"},"PeriodicalIF":1.3,"publicationDate":"2024-08-12","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"141978993","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":"Two undescribed monoterpenoids from the fruit of Gardenia jasminoides Ellis","authors":"Di Lu ,&nbsp;Yan-Gang Cao ,&nbsp;Yan-Ling Liu ,&nbsp;Xu Chen ,&nbsp;Xiang-Da Li ,&nbsp;Xin-Yi Ma ,&nbsp;Ying Niu ,&nbsp;Xiao-Ke Zheng ,&nbsp;Wei-Sheng Feng","doi":"10.1016/j.phytol.2024.08.003","DOIUrl":"10.1016/j.phytol.2024.08.003","url":null,"abstract":"<div><p>Two uncharacterized monoterpenoids (<strong>1</strong>–<strong>2</strong>) and six known analogues (<strong>3</strong>–<strong>8</strong>) were isolated from the fruit of <em>Gardenia jasminoides.</em> Their structures were determined by comprehensive spectroscopic data analysis, and the absolute configuration of <strong>2</strong> was elucidated by comparing the calculated electronic circular dichroism (ECD) spectrum with experimental ECD spectrum. Additionally, the results of preliminary activity evaluation indicated that these compounds showed slightly <em>α</em>-glucosidase inhibitory activity.</p></div>","PeriodicalId":20408,"journal":{"name":"Phytochemistry Letters","volume":"63 ","pages":"Pages 60-63"},"PeriodicalIF":1.3,"publicationDate":"2024-08-12","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"141964697","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":"Two new neo-clerodane diterpenoids from Tinospora cordifolia stems","authors":"Nhat Nam Hoang ,&nbsp;Shotaro Hoshino ,&nbsp;Takeshi Kodama ,&nbsp;Thao Xuan Hoang ,&nbsp;Hiroyasu Onaka ,&nbsp;Hiroyuki Morita","doi":"10.1016/j.phytol.2024.08.004","DOIUrl":"10.1016/j.phytol.2024.08.004","url":null,"abstract":"<div><p>Phytochemical studies of the 70 % ethanol extract of <em>Tinospora cordifolia</em> stems led to the isolation of two new <em>neo</em>-clerodane diterpenoids, including tinocordifoliols C (<strong>1</strong>) and D (<strong>2</strong>). Their structures were determined by experimental 1D and 2D NMR, HR-ESI-MS, ECD, and statistical analyses, including DP4+ probability based on DFT calculations of NMR chemical shifts. According to the previous report for two <em>neo</em>-clerodane diterpenoids, tinocordifoliols A and B, the inhibitory activities of <strong>1</strong> and <strong>2</strong> against human arginases I and II were also evaluated. In contrast to the previously reported two <em>neo</em>-clerodane diterpenoids, <strong>1</strong> and <strong>2</strong> did not show inhibitory activities against human arginases I and II. These results provide insight into the structure-activity relationship of <em>neo</em>-clerodane diterpenoids.</p></div>","PeriodicalId":20408,"journal":{"name":"Phytochemistry Letters","volume":"63 ","pages":"Pages 54-59"},"PeriodicalIF":1.3,"publicationDate":"2024-08-10","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"141963967","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 inhibition of DPP-4 by Plantago asiatica L. and the discovery of active compounds","authors":"Jian Su ,&nbsp;Chun-yun Huang ,&nbsp;Yuan-yuan Jiang ,&nbsp;Ying Hu","doi":"10.1016/j.phytol.2024.07.015","DOIUrl":"10.1016/j.phytol.2024.07.015","url":null,"abstract":"<div><p>The objective of this study was to investigate the inhibitory effects of <em>Plantago asiatica</em> L. on DPP-4 and to determine the active compounds responsible for this inhibition. Extracts were prepared from the root and aerial portions of the plant using various polar solvents. The DPP-4 inhibition of these extracts was analyzed in an extracellular assay and then assigned to either the high or low inhibition group. The chemical profiles of these extracts were analyzed using an LC-MS method. The ion fragments that were potent in the high inhibition extracts were selected through OPLS-DA and correlation analysis, and then identified and obtained for verification of DPP-4 inhibition in both the extracellular assay and the Caco-2 cell line. The extracts showed various inhibitory activities with an average inhibition of 28.4 %. A total of 20 compounds were selected from the extracts with higher inhibitory activity and identified. Six of them, baicalein, scutellarein, calceolarioside B, isoacteoside, verbascoside, and plantamajoside, exhibited DPP-4 inhibition with IC₅₀ values of 44.32, 59.90, 112.71, 157.02, 154.58, and 195.07 μg/mL, respectively, in extracellular assays. They also showed inhibition of DPP-4 on the Caco-2 cell line, with IC₅₀ values of 31.56, 34.71, 20.29, 33.29, 24.52, and 87.88 μg/mL, respectively. The extracts from PAL showed inhibitory activity towards DPP-4, and the related compounds were identified and verified.</p></div>","PeriodicalId":20408,"journal":{"name":"Phytochemistry Letters","volume":"63 ","pages":"Pages 47-53"},"PeriodicalIF":1.3,"publicationDate":"2024-08-09","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"141949487","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":"A new neo-lignan from culture broth of Phellinus linteus and its dengue virus type-2 inhibition activity","authors":"Young-Hee Kim ,&nbsp;Dae-Cheol Choi ,&nbsp;Dae-Won Ki ,&nbsp;Ji-Yul Kim ,&nbsp;Jae-Hyoung Song ,&nbsp;Hyun-Jeong Ko ,&nbsp;In-Kyoung Lee ,&nbsp;Bong-Sik Yun","doi":"10.1016/j.phytol.2024.08.005","DOIUrl":"10.1016/j.phytol.2024.08.005","url":null,"abstract":"<div><p>Several species within the genus <em>Phellinus</em> are used as a traditional medicine for various health conditions. A new neo-lignan derivative, phelignan A (<strong>1</strong>), and a known neo-lignan (<strong>2</strong>) were isolated from the culture broth of <em>P</em>. <em>linteus</em>. The chemical structures of the isolated compounds were determined using 1D- and 2D-NMR and MS data and by comparisons of the data with those reported in the literature. The anti-viral activity of the isolated compounds against dengue virus-2 (DENV-2) was evaluated. Compounds <strong>1</strong> and <strong>2</strong> exhibited anti-viral activity against DENV-2, with IC₅₀ values of 1.45 and 2.15 µM, respectively.</p></div>","PeriodicalId":20408,"journal":{"name":"Phytochemistry Letters","volume":"63 ","pages":"Pages 43-46"},"PeriodicalIF":1.3,"publicationDate":"2024-08-08","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"141949488","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":"Corrigendum to “Euphpepluone S, a new lathyrane diterpenoid with anti-inflammatory activity from Euphorbia peplus L.” [Phytochem. Lett. 55 2023, 61–66]","authors":"Shi-Peng Guan ,&nbsp;Ying Yang ,&nbsp;Mao Sun ,&nbsp;Min Cai ,&nbsp;Xue-Xue Pu ,&nbsp;Jian-Yi Huang ,&nbsp;Ping Yi ,&nbsp;Lin Liu ,&nbsp;Ming-Rui Yuan ,&nbsp;Yuan-Yuan Cheng ,&nbsp;Ying-Tong Di","doi":"10.1016/j.phytol.2024.07.016","DOIUrl":"10.1016/j.phytol.2024.07.016","url":null,"abstract":"","PeriodicalId":20408,"journal":{"name":"Phytochemistry Letters","volume":"63 ","pages":"Page 37"},"PeriodicalIF":1.3,"publicationDate":"2024-08-02","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"https://www.sciencedirect.com/science/article/pii/S1874390024001174/pdfft?md5=4a36f95057841e348bc05a19d48659a2&pid=1-s2.0-S1874390024001174-main.pdf","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"141884006","PeriodicalName":null,"FirstCategoryId":null,"ListUrlMain":null,"RegionNum":4,"RegionCategory":"生物学","ArticlePicture":[],"TitleCN":null,"AbstractTextCN":null,"PMCID":"OA","EPubDate":null,"PubModel":null,"JCR":null,"JCRName":null,"Score":null,"Total":0}