Phytochemistry Letters最新文献

{"title":"Two hispidin dimers from Piptoporellus baudonii (Fomitopsidaceae) with anticancer activity","authors":"Jenifer Reine Ngnouzouba Kuete ,&nbsp;Olyvia Gwladys Fadeyi ,&nbsp;Boris Armel Olou ,&nbsp;Frank Wilson Tiatsop Kenmoe ,&nbsp;Bienvenu Tsakem ,&nbsp;Rémy Bertrand Teponno ,&nbsp;Léon Azefack Tapondjou ,&nbsp;Simeon Fogue Kouam ,&nbsp;Nourou Soulemane Yorou","doi":"10.1016/j.phytol.2024.11.002","DOIUrl":"10.1016/j.phytol.2024.11.002","url":null,"abstract":"<div><div>Chemical analysis of the ethanol extract from the stromata of <em>Piptoporellus baudonii</em> led to the isolation and characterization of two unreported bishispidin derivatives named 11-hydroxysquarrosidine (<strong>1</strong>) and laetipohispidin (<strong>2</strong>) together with two known terpenoids: ergosterol (<strong>3</strong>) and eburicoic acid (<strong>4</strong>). Their structures were elucidated by spectroscopic methods including 1D and 2D NMR, UV, IR, ECD as well as the high-resolution mass spectrometry. Although metabolite <strong>1</strong> was reported in a patent as a synthetic compound, this is the first report on its isolation from natural source. Compounds <strong>1</strong> and <strong>2</strong> were evaluated for their antimicrobial and cytotoxic activities. 11-hydroxysquarrosidine (<strong>1</strong>) exhibited a moderate activity against all the tested human cancer cell lines with IC₅₀ values ranging from 25.79 to 73.41 µM.</div></div>","PeriodicalId":20408,"journal":{"name":"Phytochemistry Letters","volume":"65 ","pages":"Pages 19-23"},"PeriodicalIF":1.3,"publicationDate":"2024-11-15","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"142663071","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":"Announcements of the Phytochemical Society of Europe","authors":"","doi":"10.1016/S1874-3900(24)00157-5","DOIUrl":"10.1016/S1874-3900(24)00157-5","url":null,"abstract":"","PeriodicalId":20408,"journal":{"name":"Phytochemistry Letters","volume":"64 ","pages":"Pages I-III"},"PeriodicalIF":1.3,"publicationDate":"2024-11-15","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"142655433","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 phenolic glycosides from the rhizomes of Paris yunnanensis","authors":"Yu-Rui Xie ,&nbsp;Shan-Shan Ling ,&nbsp;Yan-Xi Li ,&nbsp;Mei-Ru Wang ,&nbsp;Hai-Yang Liu","doi":"10.1016/j.phytol.2024.11.007","DOIUrl":"10.1016/j.phytol.2024.11.007","url":null,"abstract":"<div><div>Phytochemical investigation on the rhizomes of <em>Paris yunnanensis</em> led to the isolation of two undescribed phenolic glycosides (<strong>1</strong> and <strong>2</strong>), and three known analogues (<strong>3</strong>-<strong>5</strong>). Their structures were determined by extensive spectroscopic analysis, including 1D and 2D NMR, MS, and UV. Among them, compounds <strong>1</strong> and <strong>2</strong> have a rare 4-<em>O</em>-<em>β</em>-D-apiofuranosyl group. The DPPH radical scavenging activities of the isolated compounds were evaluated and compound <strong>3</strong> exhibited moderate DPPH radical scavenging activity with an EC₅₀ value of 72.6 μM, while Vitamin C was used as the positive control (EC₅₀ = 24.6 μM).</div></div>","PeriodicalId":20408,"journal":{"name":"Phytochemistry Letters","volume":"65 ","pages":"Pages 15-18"},"PeriodicalIF":1.3,"publicationDate":"2024-11-14","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"142663070","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 yellow pigments related to the pitholides from the Endophyte Sordariomycetes sp.","authors":"Kousei Shimizu ,&nbsp;Reo Takahashi ,&nbsp;Zulfikar ,&nbsp;Mayuka Hakozaki ,&nbsp;Yuko Kanno ,&nbsp;Shota Uesugi ,&nbsp;Takuya Koseki ,&nbsp;Yoshihito Shiono","doi":"10.1016/j.phytol.2024.11.008","DOIUrl":"10.1016/j.phytol.2024.11.008","url":null,"abstract":"<div><div>Two novel yellow pigments, 7,8-dihydro-12-<em>O</em>-methylpitholide B (<strong>1</strong>) and 12-<em>O</em>-methylpitholide B (<strong>2</strong>), and two known compounds, pitholide B (<strong>3</strong>) and anishidiol (<strong>4</strong>), were isolated from an endophytic strain of <em>Sordariomycetes</em> sp. S-3. The structures of the new compounds, including their absolute configurations, were elucidated by nuclear magnetic resonance, infrared, ultraviolet, mass spectrometry, and electrochemical detection. The cytotoxicity and antimicrobial activities of the isolated compounds were also evaluated. Compound <strong>1</strong> exhibited cytotoxicity against HL60 cells with an IC₅₀ of 15.8 <em>μ</em>M, whereas compound <strong>3</strong> exhibited moderate cytotoxicity. Compound 3 inhibited <em>B. subtilis</em> at 50 <em>µ</em>g/disk, and <strong>4</strong> inhibited <em>Candida tropicalis</em>, <em>B. subtilis</em>, and <em>Aspergillus niger</em> at 50 µg/disk.</div></div>","PeriodicalId":20408,"journal":{"name":"Phytochemistry Letters","volume":"65 ","pages":"Pages 10-14"},"PeriodicalIF":1.3,"publicationDate":"2024-11-12","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"142663069","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":"Chalcones, flavonoids, and aristolactam alkaloids from Friesodielsia kingii and their biological activities","authors":"Sorraya Champakam ,&nbsp;Virayu Suthiphasilp ,&nbsp;Brian O. Patrick ,&nbsp;Zi Han Loh ,&nbsp;Tharakorn Maneerat ,&nbsp;Thidarat Duangyod ,&nbsp;Rawiwan Charoensup ,&nbsp;Panom Winyayong ,&nbsp;Phunrawie Promnart ,&nbsp;Sarot Cheenpracha ,&nbsp;Siau Hui Mah ,&nbsp;Raymond J. Andersen ,&nbsp;Surat Laphookhieo","doi":"10.1016/j.phytol.2024.11.004","DOIUrl":"10.1016/j.phytol.2024.11.004","url":null,"abstract":"<div><div>A new chlorinated-chalcone derivative, friesokinone A (<strong>1</strong>), and a new 3-flavene, friesokinone B (<strong>20</strong>), together with 18 known compounds (<strong>2</strong>–<strong>19</strong>), were isolated from the twigs and leaves of <em>Friesodielsia kingii</em> (J. Sinclair) Steenis<em>.</em> The dehydration of 5-methoxy-8-formyl-4,7-dihydroxy-6-methylflavan (<strong>13</strong>) to <strong>20</strong> suggests the possibility that <strong>20</strong> may be an artifact. The structures of the new compounds were elucidated based on spectroscopic data and HRESITOFMS data. In addition, the structures of <strong>1</strong> and <strong>13</strong> were confirmed by single-crystal X-ray diffraction crystallography. Compounds isolated in sufficient quantities underwent evaluation for their nitric oxide (NO) production inhibitory, glucose consumption, and glucose uptake activities. Compounds <strong>2</strong>–<strong>5</strong> possessed NO production inhibition with IC₅₀ values ranging from 17.3 to 27.6 <em>μ</em>M. Notably, compound <strong>2</strong> exhibited the strongest inhibitory effect on NO production. Compound <strong>9</strong> promoted good activities for glucose consumption with an IC₅₀ value of 73.9 <em>μ</em>M and glucose uptake with a ratio of 2.0-fold.</div></div>","PeriodicalId":20408,"journal":{"name":"Phytochemistry Letters","volume":"65 ","pages":"Pages 5-9"},"PeriodicalIF":1.3,"publicationDate":"2024-11-12","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"142663068","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":"Alkaloids from Dendrobium nobile and their anti-inflammatory activities","authors":"Zao-Yu Xu ,&nbsp;Chao-Fan Wang ,&nbsp;Wen Li ,&nbsp;Nan Fu ,&nbsp;Rui Zhan","doi":"10.1016/j.phytol.2024.11.003","DOIUrl":"10.1016/j.phytol.2024.11.003","url":null,"abstract":"<div><div>To identify anti-inflammatory alkaloids, we investigated the aerial parts of cultivated <em>Dendrobium nobile</em> Lindl. Thirteen alkaloids, including a new one, were isolated from the chloroform extract, and their structures were determined using spectroscopic methods. Bioassays assessed the anti-inflammatory activities of these isolates. Compounds <strong>1</strong> and <strong>9</strong> demonstrated inhibition of nitric oxide production in LPS-activated RAW264.7 macrophages, with IC₅₀ values of 16.7 μM and 24.4 μM, respectively.</div></div>","PeriodicalId":20408,"journal":{"name":"Phytochemistry Letters","volume":"65 ","pages":"Pages 1-4"},"PeriodicalIF":1.3,"publicationDate":"2024-11-11","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"142663067","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":"Five new chromane meroditerpenoids from the brown alga Sargassum siliquastrum of China Sea","authors":"Junzhi Pan ,&nbsp;Huayuan Liu ,&nbsp;Junpeng Xu ,&nbsp;Xiaofeng Xu ,&nbsp;Yu Qi ,&nbsp;Chaojie Wang ,&nbsp;Changle Wu ,&nbsp;Zhongmin Sun ,&nbsp;Yali Lv ,&nbsp;Pengcheng Yan","doi":"10.1016/j.phytol.2024.11.001","DOIUrl":"10.1016/j.phytol.2024.11.001","url":null,"abstract":"<div><div>Five previously undescribed chromane-type meroditerpenoids, sargasilols J–N (<strong>1</strong>–<strong>5</strong>), were isolated from an EtOAc-soluble extract of the brown alga <em>Sargassum siliquastrum</em> collected in the China Sea. The chemical structures of these meroditerpenoids were determined by extensive spectroscopic analyses, including 1D/2D NMR, ECD, and HR-ESI-MS data. Compound <strong>3</strong> exhibited potent anti-neuroinflammatory activity against lipopolysaccharide (LPS)-induced nitric oxide (NO) production in BV-2 microglia cells, with an IC₅₀ value of 9.9 <em>μ</em>M.</div></div>","PeriodicalId":20408,"journal":{"name":"Phytochemistry Letters","volume":"64 ","pages":"Pages 133-137"},"PeriodicalIF":1.3,"publicationDate":"2024-11-06","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"142592654","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":"Water-soluble amino acid derivatives isolated from cultures of three fungal strains","authors":"Matheus Gotha ,&nbsp;Gabriel C. Junqueira ,&nbsp;Ariane F. Bertonha ,&nbsp;Julie P.G. Rodríguez ,&nbsp;Juliana R. Gubiani ,&nbsp;Emanuele F. Pissinati ,&nbsp;Rafaely N. Lima ,&nbsp;Lara D. Sette ,&nbsp;Simone P. de Lira ,&nbsp;Luciane F.P. Oliveira ,&nbsp;Andrea N.L. Batista ,&nbsp;João M. Batista Jr. ,&nbsp;Antonio G. Ferreira ,&nbsp;Márcio W. Paixão ,&nbsp;Marcelo R. Amorim ,&nbsp;Roberto G.S. Berlinck","doi":"10.1016/j.phytol.2024.10.005","DOIUrl":"10.1016/j.phytol.2024.10.005","url":null,"abstract":"<div><div>The isolation of amino acid-derived metabolites from the aqueous fractions of cultures of three fungal strains is reported. From cultures of <em>Penicillium coffeae</em> M3 two β-carboline alkaloids were isolated and identified, the new (+)-(1<em>R</em>,3<em>R</em>)-1-methyl-1,2,3,4-tetrahydro-<em>β</em>-carboline-3-carboxylic acid (<strong>1</strong>) and the known (–)-lycoperodine-1 (<strong>2</strong>), along with the diketopiperazine <em>cyclo</em>[<span>l</span>-prolyl-<span>l</span>-tyrosyl] (<strong>3</strong>) and the isocoumarin 6,8-dihydroxy-3-methylisocoumarin (<strong>5</strong>). The diketopiperazines (<strong>3</strong>), <em>cyclo</em>[<span>d</span>-prolyl-<span>l</span>-phenylalanyl] (<strong>4</strong>) and <em>cyclo</em>[<span>l</span>-prolyl-<span>l</span>-phenylalanyl] (<strong>6</strong>) were isolated and identified from cultures of <em>Trichoderma</em> sp. L2–2. The peptaibol trichokonin VI (<strong>7</strong>) was also identified by UPLC-MS/MS analysis in aqueous fractions from cultures of the same <em>Trichoderma</em> sp. strain, by comparison with an authentic standard, isolated and identified from the organic fraction of the same fungus culture. The amino acid derivatives formyl-<span>l</span>-tryptophyl-<span>l</span>-alanine (<strong>8</strong>), <em>cyclo</em>-(<span>d</span>-Trp- <span>l</span>-Glu) (<strong>9</strong>), and (<em>S</em>)-<em>N</em>-acetyl-kynurenine (<strong>10</strong>), were isolated from cultures of the endophytic fungus <em>Paecilomyces</em> sp. Aa1. The planar structures of the amino acid derivatives <strong>1</strong>-<strong>4</strong>, <strong>6</strong>, <strong>8</strong>-<strong>10</strong>, as well as of the isocoumarin <strong>5</strong>, were established by analysis of spectroscopic data, including MS/MS fragmentation and comparison with literature data. The configurational assignments were performed by analysis of Marfey derivatives and/or by comparison between experimental and calculated ECD data. The results obtained give further support that investigation of aqueous fractions of fungal cultures may provide structurally relevant and potentially bioactive secondary metabolites.</div></div>","PeriodicalId":20408,"journal":{"name":"Phytochemistry Letters","volume":"64 ","pages":"Pages 123-132"},"PeriodicalIF":1.3,"publicationDate":"2024-11-05","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"142586790","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":"Discovery of polyoxygenated briaranes from octocoral Briareum stechei","authors":"Yue-Wen Chuang ,&nbsp;Wei-Chen Ting ,&nbsp;Su-Ying Chien ,&nbsp;Li-Guo Zheng ,&nbsp;Chih-Yin Huang ,&nbsp;Zhi-Hong Wen ,&nbsp;Yu-Jen Wu ,&nbsp;Junichi Tanaka ,&nbsp;You-Ying Chen ,&nbsp;Jui-Hsin Su ,&nbsp;Ping-Jyun Sung","doi":"10.1016/j.phytol.2024.10.008","DOIUrl":"10.1016/j.phytol.2024.10.008","url":null,"abstract":"<div><div>A new 8,17-epoxybriarane, briastecholide O (<strong>1</strong>), was isolated from an encrusting algae-containing cultured octocoral <em>Briareum stechei</em>. Moreover, wild-type <em>B. stechei</em> collected from Okinawan waters yielded a new 8,17-epoxybriarane, briastecholide P (<strong>2</strong>), along with two known analogs, namely, briaexcavatins G (<strong>3</strong>) and X (<strong>4</strong>). Single-crystal X-ray diffraction was conducted to determine the absolute configurations of <strong>2</strong>–<strong>4</strong>, while the structure of <strong>1</strong> was established by spectroscopic elucidation. Briaranes <strong>1</strong> and <strong>3</strong> were active in enhancing the growth of MG-63 human mesenchymal stem cells.</div></div>","PeriodicalId":20408,"journal":{"name":"Phytochemistry Letters","volume":"64 ","pages":"Pages 117-122"},"PeriodicalIF":1.3,"publicationDate":"2024-11-04","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"142577980","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":"Anti-inflammatory pregnene steroids from the oleo-gum resin of Commiphora mukul: in-vitro and in-silico studies","authors":"Mohamed H. Abd El-Razek ,&nbsp;Ahmed H. Afifi ,&nbsp;Mohamed Hassan Nasraa ,&nbsp;Ahmed A. Elrashedy ,&nbsp;Mohamed Aboelmagd ,&nbsp;Abdelhalim A. Elgahamy ,&nbsp;Mai M. Elghonemy ,&nbsp;Tarik A. Mohamed ,&nbsp;Mohamed-Elamir F. Hegazy ,&nbsp;Ahmed H. El-Desoky","doi":"10.1016/j.phytol.2024.10.006","DOIUrl":"10.1016/j.phytol.2024.10.006","url":null,"abstract":"<div><div>Phytochemical investigation of a methanolic extract derived from the oleo-gum resin of <em>Commiphora mukul</em> resulted in the isolation of seven pregnene-type steroids (<strong>1</strong>-<strong>7</strong>), including a new compound named commukulsterol A (<strong>1</strong>). Their structures were decided by extensive analyses of 1D, 2D-NMR and Mass spectra. The relative configurations of commukulsterols A (<strong>1</strong>) and B (<strong>2</strong>) were determined <em>via</em> DFT calculations of their ¹H and ¹³C chemical shifts, followed by DP4+ statistical analysis. Absolute configurations were then decided by biogenetic similarities and specific rotations. Such analyses led to the revision of the structure of <strong>2</strong>, initially elucidated as 20<em>S</em>-acetyloxy-4-pregnene-3,16-dione, to pro-20<em>R</em>. <strong>1</strong>-<strong>7</strong> showed varying inhibitory effects on LPS-induced NO release in RAW264.7 macrophages, with IC₅₀ values ranging from 7.6 to 53.9 μM for (<strong>1</strong>-<strong>6)</strong>, while <strong>7</strong> didn’t show activity up to 100 μM. On the other hand, molecular docking revealed that <strong>3</strong> &amp; <strong>4</strong> could bind to the catalytic site of inducible nitric oxide synthase (iNOS). Moreover, molecular dynamics simulation of <strong>3</strong> &amp; <strong>4</strong> in association with iNOS were examined for 200 ns, revealing adequate stability. ADMET analysis indicated good oral bioavailability and drug-like properties. The observed chemical profile highlighted a unique chemical relationship between Burseraceae and Simaroubaceae families.</div></div>","PeriodicalId":20408,"journal":{"name":"Phytochemistry Letters","volume":"64 ","pages":"Pages 106-116"},"PeriodicalIF":1.3,"publicationDate":"2024-11-01","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"142572159","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}