Ming-Jen Cheng , Jih-Jung Chen , Hsia-Wei Liu , Ming-Der Wu , Yu-Hui Wei , Guey-Yuh Liou , Min Tseng
{"title":"Extraction and assessment of antifungal properties of natural products from the culture medium of Trichoderma sp. 18F0056","authors":"Ming-Jen Cheng , Jih-Jung Chen , Hsia-Wei Liu , Ming-Der Wu , Yu-Hui Wei , Guey-Yuh Liou , 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}
Haeun Kwon , Hee Woon Ann , Jin Su Lee , Jaeyoung Kwon , Keunwan Park , Yuanqiang Guo , Bang Yeon Hwang , Jae-Jin Kim , Joung Han Yim , Il-Chan Kim , Dae Sik Jang , Sullim Lee , Dongho Lee
{"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 , Hee Woon Ann , Jin Su Lee , Jaeyoung Kwon , Keunwan Park , Yuanqiang Guo , Bang Yeon Hwang , Jae-Jin Kim , Joung Han Yim , Il-Chan Kim , Dae Sik Jang , Sullim Lee , 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}
Musa Kisiriko , Gabin T.M. Bitchagno , Clarice Noleto-Dias , Imane Naboulsi , Maria Anastasiadi , Leon A. Terry , Mansour Sobeh , Michael H. Beale , Jane L. Ward
{"title":"The untargeted metabolomic analysis of Ammodaucus leucotrichus Coss. & Dur. seeds reveals previously undescribed polar lignans and terpenoids","authors":"Musa Kisiriko , Gabin T.M. Bitchagno , Clarice Noleto-Dias , Imane Naboulsi , Maria Anastasiadi , Leon A. Terry , Mansour Sobeh , Michael H. Beale , 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. & 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}
Thi Tu Oanh Nguyen , Thi Minh Hang Nguyen , Mai Thao Vu , Yohan Seo , SeonJu Park , Van Cuong Pham , Van Hung Nguyen , Xuan Nhiem Nguyen
{"title":"A new furanoditerpene from Saururus chinensis aerial parts","authors":"Thi Tu Oanh Nguyen , Thi Minh Hang Nguyen , Mai Thao Vu , Yohan Seo , SeonJu Park , Van Cuong Pham , Van Hung Nguyen , Xuan Nhiem Nguyen","doi":"10.1016/j.phytol.2024.11.009","DOIUrl":"10.1016/j.phytol.2024.11.009","url":null,"abstract":"<div><div>A new furanoditerpene, saurufuranol (<strong>1</strong>) along with a flavonoid, 3,5,7,3′,4′-pentamethoxyflavone (<strong>2</strong>), and eight lignans including macelignan (<strong>3</strong>), 5-((2<em>R</em>,3<em>R</em>)-4-(3,4-dimethoxyphenyl)-2,3-dimethylbutyl)benzo[<em>d</em>][1,3]dioxole (<strong>4</strong>), dihydroguaiaretic acid (<strong>5</strong>), <strong>(+)-</strong>zuonin A (<strong>6</strong>), sauchinone (<strong>7</strong>), saucerneol A (<strong>8</strong>), manassantin A (<strong>9</strong>) and saucerneol C (<strong>10</strong>). Their structures were determined by extensive spectroscopic studies using NMR spectroscopy and mass spectrometry in combination with literature. These compounds were evaluated cytotoxicity on PC-9 and HT-29 cancer cell line. Compound <strong>8</strong> showed significant activity on both of cancer cell lines with IC<sub>50</sub> values of 1.33±0.23 and 1.18±0.27 µM, respectively.</div></div>","PeriodicalId":20408,"journal":{"name":"Phytochemistry Letters","volume":"65 ","pages":"Pages 24-27"},"PeriodicalIF":1.3,"publicationDate":"2024-11-20","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"142704456","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 hispidin dimers from Piptoporellus baudonii (Fomitopsidaceae) with anticancer activity","authors":"Jenifer Reine Ngnouzouba Kuete , Olyvia Gwladys Fadeyi , Boris Armel Olou , Frank Wilson Tiatsop Kenmoe , Bienvenu Tsakem , Rémy Bertrand Teponno , Léon Azefack Tapondjou , Simeon Fogue Kouam , 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 IC<sub>50</sub> 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}
Yu-Rui Xie , Shan-Shan Ling , Yan-Xi Li , Mei-Ru Wang , Hai-Yang Liu
{"title":"Two new phenolic glycosides from the rhizomes of Paris yunnanensis","authors":"Yu-Rui Xie , Shan-Shan Ling , Yan-Xi Li , Mei-Ru Wang , 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 EC<sub>50</sub> value of 72.6 μM, while Vitamin C was used as the positive control (EC<sub>50</sub> = 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 , Reo Takahashi , Zulfikar , Mayuka Hakozaki , Yuko Kanno , Shota Uesugi , Takuya Koseki , 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 IC<sub>50</sub> 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}
Sorraya Champakam , Virayu Suthiphasilp , Brian O. Patrick , Zi Han Loh , Tharakorn Maneerat , Thidarat Duangyod , Rawiwan Charoensup , Panom Winyayong , Phunrawie Promnart , Sarot Cheenpracha , Siau Hui Mah , Raymond J. Andersen , Surat Laphookhieo
{"title":"Chalcones, flavonoids, and aristolactam alkaloids from Friesodielsia kingii and their biological activities","authors":"Sorraya Champakam , Virayu Suthiphasilp , Brian O. Patrick , Zi Han Loh , Tharakorn Maneerat , Thidarat Duangyod , Rawiwan Charoensup , Panom Winyayong , Phunrawie Promnart , Sarot Cheenpracha , Siau Hui Mah , Raymond J. Andersen , 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 IC<sub>50</sub> 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 IC<sub>50</sub> 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}
Zao-Yu Xu , Chao-Fan Wang , Wen Li , Nan Fu , Rui Zhan
{"title":"Alkaloids from Dendrobium nobile and their anti-inflammatory activities","authors":"Zao-Yu Xu , Chao-Fan Wang , Wen Li , Nan Fu , 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 IC<sub>50</sub> 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}