Phytochemistry Letters最新文献

{"title":"Spectroscopic effects on natural occurring O-sulfated flavones from Wissadula periplocifolia","authors":"Yanna C.F. Teles ,&nbsp;Paulo G. Pereira-Júnior ,&nbsp;Carlos V. Santos-Jr ,&nbsp;Renaldo T. Moura Jr. ,&nbsp;Maria de Fátima V. de Souza","doi":"10.1016/j.phytol.2024.12.010","DOIUrl":"10.1016/j.phytol.2024.12.010","url":null,"abstract":"<div><div>Natural occurring <em>O-</em>sulfated flavonoids have been reported from the plant specie <em>Wissadula periplocifolia</em> Presl. (Malvaceae). Sulfated flavonoids are considered uncommon flavonoid derivatives and the biological relevance of sulfation on specialized metabolites are still poorly understood. In the recent years, the interest on <em>O</em>-sulfated flavonoids has aroused since they have shown anticoagulant, larvicidal and antiproliferative potential. Due the low occurrence of <em>O</em>-sulfated flavonoids the literature is scarce regarding specific isolation, identification and spectroscopic data. In this approach, the complete NMR data of a new bi-<em>O</em>-sulfated flavone isolated from <em>W. periplocifolia</em> are presented. Additionally, based on the obtained experimental and theoretical NMR data, the spectroscopic effects caused by the <em>O</em>-sulfate groups in natural occurring falvones were evaluated in order to better understand the additional effects on multiple <em>O</em>-sulfated compounds. The identified substance was purified from aerial parts of <em>W. periplocifolia</em> using Sephadex chromatographic column. The compound was identified by 1D and 2D NMR and HRMS as the unreported compound 4’-<em>O</em>-methyl-7,8-di-<em>O</em>-sulfate isoscutellarein (telescutellarein). The experimental NMR data was complemented by DFT calculations at the ωB97X-D3/def2-TZVP level of theory. The theoretical NMR spectra were simulated using the GIAO approach, and the observed chemical shifts due to the two <em>O</em>-sulfate groups were analyzed using chemical bond descriptors (QTAIM and OP/TOP) to study the bonds between the aromatic ring and their substituent groups. The anticipated electron-withdrawing and electron-donating effects of the <em>O</em>-sulfate and OH substituents on the aromatic ring were explored through a synergic experimental and theoretical analysis.</div></div>","PeriodicalId":20408,"journal":{"name":"Phytochemistry Letters","volume":"65 ","pages":"Pages 117-123"},"PeriodicalIF":1.3,"publicationDate":"2025-02-01","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"143170922","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 diterpenoid alkaloid from the Aconitum scaposum","authors":"Cheng-En Fu ,&nbsp;Gui-Fang Li ,&nbsp;Guo-Qing Sun ,&nbsp;Shuai Huang ,&nbsp;Lin Chen ,&nbsp;Xian-Li Zhou","doi":"10.1016/j.phytol.2024.12.002","DOIUrl":"10.1016/j.phytol.2024.12.002","url":null,"abstract":"<div><div>A new atisine-type C₂₀-diterpenoid alkaloid (scaposum A) and twelve known compounds (<strong>2–13</strong>) were isolated from the dried tuberous roots of <em>Aconitum scaposum</em> Franch and characterized by spectroscopic analyses such as IR, HR-ESI-MS and NMR. All compounds were isolated from this plant for the first time and tested for their anti-proliferative effects on Sf9 and 4T1 cells, inhibition of NO production from LPS-induced BV2 and RAW264.7 cells, and inhibition of acetylcholinesterase from Electrophorus electricus (eeAChE). The results showed that compounds <strong>8</strong> (81.26 %) and <strong>11</strong> (80.99 %) exhibited anti-proliferative effects on 4T1 cells at 100 <em>μ</em>M, which were comparable to that of camptothecin (81.61 %), and compound <strong>7</strong> (30 <em>μ</em>M) exhibited a moderate inhibitory effect on NO release from LPS-induced BV2 cells, in addition to the moderate inhibitory effect of all compounds on the eeAChE.</div></div>","PeriodicalId":20408,"journal":{"name":"Phytochemistry Letters","volume":"65 ","pages":"Pages 89-93"},"PeriodicalIF":1.3,"publicationDate":"2025-02-01","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"143170915","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":"Sesquiterpene glycosides from Sapindus mukorossi","authors":"Le Thi Vien ,&nbsp;Do Hoang Anh ,&nbsp;Pham Thi Mai Huong ,&nbsp;Pham Thi Cham ,&nbsp;Ninh Thi Ngoc ,&nbsp;Nguyen Mai Anh ,&nbsp;Nguyen The Cuong ,&nbsp;Tran Thi Hong Hanh ,&nbsp;Nguyen Xuan Cuong","doi":"10.1016/j.phytol.2025.01.001","DOIUrl":"10.1016/j.phytol.2025.01.001","url":null,"abstract":"<div><div>A phytochemical investigation of <em>Sapindus mukorossi</em> pericarps yielded six acyclic sesquiterpene glycosides (<strong>1</strong>−<strong>6</strong>), including three new compounds, named mukuroziosides A−C (<strong>1</strong>−<strong>3</strong>). Structural characterization was confirmed by an extensive analysis of 1D and 2D NMR and HR-ESI-QTOF mass spectra. Notably, compound <strong>4</strong> was isolated from natural sources for the first time. The antibacterial effects of all compounds were evaluated against six bacterial strains: <em>Enterococcus faecalis</em> (ATCC299212), <em>Staphylococcus aureus</em> (ATCC25923), <em>Bacillus cereus</em> (ATCC14579), <em>Escherichia coli</em> (ATCC25922), <em>Pseudomonas aeruginosa</em> (ATCC27853), and <em>Salmonella enterica</em> (ATCC13076). All compounds were demonstrated minimum inhibitory concentration of &gt;400 μM, indicating inactivity against these bacterial strains.</div></div>","PeriodicalId":20408,"journal":{"name":"Phytochemistry Letters","volume":"65 ","pages":"Pages 128-132"},"PeriodicalIF":1.3,"publicationDate":"2025-02-01","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"143170924","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":"Bioassay-guided isolation of acetylcholinesterase and butyrylcholinesterase inhibitors from Horsfieldia tomentosa fruits (Myristicaceae)","authors":"Mohammed Idris ,&nbsp;Thaigarajan Parumasivam ,&nbsp;Khalijah Awang ,&nbsp;Azeana Zahari ,&nbsp;Marc Litaudon ,&nbsp;Cécile Apel ,&nbsp;Unang Supratman ,&nbsp;Mohammad Tasyriq Che Omar ,&nbsp;Mohamad Nurul Azmi","doi":"10.1016/j.phytol.2025.01.007","DOIUrl":"10.1016/j.phytol.2025.01.007","url":null,"abstract":"<div><div>Alzheimer's disease (AD) is the most common form of dementia associated with the accumulation of abnormal protein deposits in the brain, including beta-amyloid plaques and <em>tau</em> tangles, as well as oxidative stress. The limited effectiveness of current medications in temporarily treating symptoms has driven interest in natural products for their diverse biological activities. This study investigates the bioactive potential of various extracts obtained from the fruits of <em>Horsfieldia tomentosa</em>, focusing on their antioxidant and anticholinesterase properties. Total phenolic and flavonoid contents were quantified, antioxidant and anticholinesterase activities were evaluated. The ethyl acetate extract exhibited the highest bioactivity, with total flavonoid content (361.11 ± 26.24 mg QE/g), total phenolic content (1601.46 ± 1.23 mg GAE/g), antioxidant activity (1.81 ± 0.06 µg/L), and significant anticholinesterase activities (AChE = 6.0 ± 0.30 µg/mL; BuChE = 32.1 µg/mL). Three previously undescribed phenolic compounds along with four known compounds were purified from this extract. The assayed isolated compounds exhibit selective cholinesterase inhibition, with compound <strong>2</strong> showing the strongest activity (IC₅₀ value of 3.9 µM against AChE), while compound <strong>1</strong> was more effective against butyrylcholinesterase (IC₅₀ value of 7.8 µM). Molecular docking supported the in vitro findings, revealing binding energies of - 9.0 ± 0.5, - 8.5 ± 0.1, and - 8.3 ± 0.1 kcal mol⁻¹ for compounds <strong>1</strong>, <strong>2</strong> and <strong>5</strong>, respectively, against butyrylcholine protease (6ESY). Compound <strong>1</strong> also showed significant binding energy (- 8.0 ± 0.1 kcal mol⁻¹⁾ against acetylcholine protease (4MOE). In these results, compound <strong>2</strong> acts as a dual inhibitor, while compounds <strong>1</strong> and <strong>5</strong> primarily inhibit butyrylcholinesterase. These results underscore the therapeutic potential of <em>Horsfieldia tomentosa</em> in treating Alzheimer’s disease.</div></div>","PeriodicalId":20408,"journal":{"name":"Phytochemistry Letters","volume":"65 ","pages":"Pages 133-140"},"PeriodicalIF":1.3,"publicationDate":"2025-02-01","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"143170925","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 eremophilane-type sesquiterpenoid and new chromanone isolated from marine derived fungus Humicola sp. GXIMD02070","authors":"Quan Teng ,&nbsp;Qiuxia Nong ,&nbsp;Xin Jin ,&nbsp;Chenghai Gao ,&nbsp;Along Zhang ,&nbsp;Nannan Xing ,&nbsp;Xianqiang Chen","doi":"10.1016/j.phytol.2024.11.011","DOIUrl":"10.1016/j.phytol.2024.11.011","url":null,"abstract":"<div><div>Chemical investigation of a marine-derived fungus <em>Humicola</em> sp. GXIMD02070 resulted in the isolation of one new eremophilane-type sesquiterpenoid (<strong>1</strong>), one new chromanone analogue (<strong>2</strong>), and three previously described metabolites, namely chaetosemin D (<strong>3</strong>), butyrolactone I (<strong>4</strong>), and isoochracinic acid (<strong>5</strong>). Their structures were elucidated by comprehensive analyses of the spectroscopic methods, quantum chemical calculation of NMR, and electronic circular dichroism (ECD) calculations. Compounds <strong>1</strong> and <strong>2</strong> exhibited inhibitory effects on NO production with EC₅₀ value of 82.04 ± 0.12 μM and 100.2 ± 0.13 μM, respectively, indicating moderate anti-inflammatory activity.</div></div>","PeriodicalId":20408,"journal":{"name":"Phytochemistry Letters","volume":"65 ","pages":"Pages 48-52"},"PeriodicalIF":1.3,"publicationDate":"2025-02-01","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"143171798","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":"Chemical composition and antibacterial activity of chaulmoogra oil from Hydnocarpus wightiana: A detailed analysis of volatile and fatty acid fractions","authors":"Natalia Schäfer ,&nbsp;Katarzyna Pokajewicz ,&nbsp;Radosław Balwierz ,&nbsp;Adam Byrski ,&nbsp;Paweł Biernat ,&nbsp;Jacek Lipok","doi":"10.1016/j.phytol.2024.12.008","DOIUrl":"10.1016/j.phytol.2024.12.008","url":null,"abstract":"<div><div>The aim of the study was to ascertain the chemical composition of the volatile and fatty acid fractions of chaulmoogra oil from <em>Hydnocarpus wightiana</em>. A series of GC-MS/SPME analyses revealed that chaulmoogra oil contains a diverse array of volatile compounds, with a notable proportion comprising terpene compounds (22.3 %). The GC-MS analysis confirmed the presence of cyclopentenyl fatty acids in chaulmoogra oil from <em>Hydnocarpus wightiana</em> which constituted about 80 % of the fatty acid fraction. Furthermore, the chaulmoogra oil was extracted using methanol. The methanol extract obtained was subjected to GC-MS analysis for the identification of fatty compounds and volatile compounds. Methanol was identified as an effective extractant for the cyclopentenyl fatty acid fraction. The quantitative content of cyclopentenyl fatty acids in the methanol extract was similar to the content of these acids in the whole chaulmoogra oil. This proves that the derivatization method used in this work was appropriate. A further crucial aspect of the research was the assessment of the antibacterial activity of both the whole oil and its methanol extract against reference bacterial strains such as <em>Escherichia coli</em>, <em>Staphylococcus aureus</em> and <em>Bacillus subtilis</em>. The results indicate that both the oil and its fraction obtained through methanol extraction exert a slight bacteriostatic effect on the aforementioned bacterial strains.</div></div>","PeriodicalId":20408,"journal":{"name":"Phytochemistry Letters","volume":"65 ","pages":"Pages 102-112"},"PeriodicalIF":1.3,"publicationDate":"2025-02-01","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"143171102","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":"Four aromatic polyketides from the endophytic fungus Epicoccum nigrum","authors":"Jingshu Zhang ,&nbsp;Pengran Cao ,&nbsp;Wensen Li,&nbsp;Yongxin Wei,&nbsp;Lingyi Kong,&nbsp;Minghua Yang","doi":"10.1016/j.phytol.2025.01.002","DOIUrl":"10.1016/j.phytol.2025.01.002","url":null,"abstract":"<div><div>Four aromatic polyketides (<strong>1</strong>-<strong>4</strong>) were isolated from the strains of the endophytic <em>Epicoccum nigrum</em>. Their structures were confirmed by comprehensive spectroscopic analysis. Compounds <strong>1–4</strong> possessed two unusual carbon skeletons and were proposed to be dimeric products of pyrogallol analogs. All compounds displayed moderate inhibitory activity against <em>Candida glabrata</em>, with MIC values ranging from 2.50 to 8.20 μg/mL.</div></div>","PeriodicalId":20408,"journal":{"name":"Phytochemistry Letters","volume":"65 ","pages":"Pages 152-155"},"PeriodicalIF":1.3,"publicationDate":"2025-02-01","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"143170927","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":"Extraction and assessment of antifungal properties of natural products from the culture medium of Trichoderma sp. 18F0056","authors":"Ming-Jen Cheng ,&nbsp;Jih-Jung Chen ,&nbsp;Hsia-Wei Liu ,&nbsp;Ming-Der Wu ,&nbsp;Yu-Hui Wei ,&nbsp;Guey-Yuh Liou ,&nbsp;Min Tseng","doi":"10.1016/j.phytol.2024.10.009","DOIUrl":"10.1016/j.phytol.2024.10.009","url":null,"abstract":"<div><div>Two previously undescribed chromone derivatives, <strong>1</strong> and <strong>2</strong>, were isolated from the EtOAc-soluble fraction of the culture broth of <em>Trichoderma</em> sp. 18F0056. Their structures were elucidated on the basis of extensive analyses of spectroscopic data and comparison with literature data. Their antifungal activity was also evaluated. Our results showed that both constituents possessed weak antifungal activity against <em>Fusarium</em> sp. LC8, <em>Neopestalotiopsis</em> sp. BCRC 35002, and <em>Colletotrichum gloeosporioides</em> BCRC 35178. In the past, chromone derivatives were rarely found from the genus <em>Trichoderma</em>. This time, the research on the products of this new species of <em>Trichoderma</em> is of significant significance. <em>Trichoderma</em> natural products deserve further evaluation as anti-fungal agents for biocontrol.</div></div>","PeriodicalId":20408,"journal":{"name":"Phytochemistry Letters","volume":"65 ","pages":"Pages 44-47"},"PeriodicalIF":1.3,"publicationDate":"2024-11-25","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"142704459","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 compounds from Apiospora xenocordella culture medium and their inhibitory effects on TNF-α-induced ROS generation and MMP-1 secretion","authors":"Haeun Kwon ,&nbsp;Hee Woon Ann ,&nbsp;Jin Su Lee ,&nbsp;Jaeyoung Kwon ,&nbsp;Keunwan Park ,&nbsp;Yuanqiang Guo ,&nbsp;Bang Yeon Hwang ,&nbsp;Jae-Jin Kim ,&nbsp;Joung Han Yim ,&nbsp;Il-Chan Kim ,&nbsp;Dae Sik Jang ,&nbsp;Sullim Lee ,&nbsp;Dongho Lee","doi":"10.1016/j.phytol.2024.11.005","DOIUrl":"10.1016/j.phytol.2024.11.005","url":null,"abstract":"<div><div>A new cytosporin derivative (<strong>1</strong>) and a new phenolic compound (<strong>2</strong>), together with cytosporin D (<strong>3</strong>), were isolated from an EtOAc extract of <em>Apiospora xenocordella</em> culture medium. The isolation workflow was guided by a Molecular Networking-based dereplication strategy. The chemical structures of the new compounds were determined by using MS and NMR spectroscopic techniques, and the absolute configurations were established by the modified Mosher’s method and quantum chemical calculation of electronic circular dichroism. UV radiation activates pro-inflammatory cytokines, such as TNF-α, a major contributor to skin aging through ROS generation and MMP-1 secretion. Cytosporin D (<strong>3</strong>) exhibited the inhibition of TNF-α-induced ROS and MMP-1. UV radiation activates pro-inflammatory cytokines including TNF-α which is a major contributor to skin aging through reactive oxygen species (ROS) generation and matrix metalloproteinase-1 (MMP-1) secretion. Cytosporin D (<strong>3</strong>) exhibited moderate inhibition against TNF-α-induced ROS and MMP-1. This compound docked computationally into the active site of MMP-1 (−5.9 kcal/mol). Compound <strong>1</strong>, though not tested due to limited quantity, showed a docking simulation result (−6.0 kcal/mol) similar to cytosporin D (<strong>3</strong>), indicating potential activity.</div></div>","PeriodicalId":20408,"journal":{"name":"Phytochemistry Letters","volume":"65 ","pages":"Pages 38-43"},"PeriodicalIF":1.3,"publicationDate":"2024-11-22","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"142704458","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 untargeted metabolomic analysis of Ammodaucus leucotrichus Coss. & Dur. seeds reveals previously undescribed polar lignans and terpenoids","authors":"Musa Kisiriko ,&nbsp;Gabin T.M. Bitchagno ,&nbsp;Clarice Noleto-Dias ,&nbsp;Imane Naboulsi ,&nbsp;Maria Anastasiadi ,&nbsp;Leon A. Terry ,&nbsp;Mansour Sobeh ,&nbsp;Michael H. Beale ,&nbsp;Jane L. Ward","doi":"10.1016/j.phytol.2024.11.006","DOIUrl":"10.1016/j.phytol.2024.11.006","url":null,"abstract":"<div><div>The polar metabolome of the medicinal plant <em>Ammodaucus leucotrichus</em> Coss. &amp; Dur. has not been comprehensively characterised. In this study, the chemical composition of a water/methanol (4:1) extract of seeds was determined through a combination of UHPLC-MS and NMR techniques. Sixty compounds were identified from the extract with 36 of these confirmed using UHPLC-MS and/or NMR data while the remaining 24 were given putative identifications based on UHPLC-MS data. The compounds included lignans, terpenes, phenolics, flavonoids, and alkaloid derivatives together with some amino- and organic acids. Of these 2 terpenoids and 3 lignans were found to be novel and were isolated and structures determined by comprehensive NMR studies. A further novel lignan glycoside was tentatively identified. Together these data represent the most comprehensive profile of this traditional medicinal plant, providing an annotated profile that can form the basis of future correlative metabolomic investigations to determine active principles behind its reported bioactivities.</div></div>","PeriodicalId":20408,"journal":{"name":"Phytochemistry Letters","volume":"65 ","pages":"Pages 28-37"},"PeriodicalIF":1.3,"publicationDate":"2024-11-21","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"142704457","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}