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A Comparative Study on the DNA Interactions and Biological Activities of Benzophenanthridine and Protoberberine Alkaloids. 苯并菲啶和原小檗碱生物碱 DNA 相互作用和生物活性的比较研究
IF 3.3 2区 生物学
Journal of Natural Products Pub Date : 2024-09-27 Epub Date: 2024-08-30 DOI: 10.1021/acs.jnatprod.4c00416
Shuang Zu, Zhenhao Long, Xiangru Zhang, Jing Sheng, Yang Xu, Haojun Sun, Xiangjun Liu, Dihua Shangguan
{"title":"A Comparative Study on the DNA Interactions and Biological Activities of Benzophenanthridine and Protoberberine Alkaloids.","authors":"Shuang Zu, Zhenhao Long, Xiangru Zhang, Jing Sheng, Yang Xu, Haojun Sun, Xiangjun Liu, Dihua Shangguan","doi":"10.1021/acs.jnatprod.4c00416","DOIUrl":"10.1021/acs.jnatprod.4c00416","url":null,"abstract":"<p><p>Numerous small molecules exert antitumor effects by interacting with DNA, thereby influencing processes, such as DNA replication, transcription, meiosis, and gene recombination. Benzophenanthridine and protoberberine alkaloids are known to bind DNA and exhibit many pharmacological activities. In this study, we conducted a comparative analysis of the interactions between these two classes of alkaloids with G-quadruplex (G4) DNA and double-stranded DNA (dsDNA). Protoberberine alkaloids showed a greater affinity for binding with G4s than with dsDNA, while benzophenanthridine alkaloids exhibited a significantly stronger binding capacity for dsDNA, especially in regions that are rich in AT base pairs. Benzophenanthridine alkaloids also exhibited much stronger toxicity to various cancer cells. Compared with protoberberine alkaloids, benzophenanthridine alkaloids displayed much stronger activity in inhibiting cellular DNA and RNA synthesis, arresting the cell cycle in the G2/M phase, inducing cell apoptosis, and leading to intracellular DNA damage. Given that dsDNA constitutes the predominant form of DNA within cells for the majority of the cell cycle, the significant antiproliferative activity of benzophenanthridine alkaloids could be attributed, in part, to their higher binding affinity for dsDNA, thereby exerting a more significant impact on cellular proliferation. These findings have valuable implications for understanding the biological activities of isoquinoline alkaloids and their antitumor applications.</p>","PeriodicalId":47,"journal":{"name":"Journal of Natural Products ","volume":" ","pages":"2170-2179"},"PeriodicalIF":3.3,"publicationDate":"2024-09-27","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"142102187","PeriodicalName":null,"FirstCategoryId":null,"ListUrlMain":null,"RegionNum":2,"RegionCategory":"生物学","ArticlePicture":[],"TitleCN":null,"AbstractTextCN":null,"PMCID":"","EPubDate":null,"PubModel":null,"JCR":null,"JCRName":null,"Score":null,"Total":0}
引用次数: 0
Pemuchiamides A and B, Proline-Rich Linear Lipopeptides, Isolated from a Marine Hormoscilla sp. Cyanobacterium. Pemuchiamides A 和 B,富含脯氨酸的线性脂肽,从海洋 Hormoscilla sp.
IF 3.3 2区 生物学
Journal of Natural Products Pub Date : 2024-09-27 Epub Date: 2024-08-15 DOI: 10.1021/acs.jnatprod.4c00733
Kensuke Irie, Ghulam Jeelani, Tomoyoshi Nozaki, Arihiro Iwasaki
{"title":"Pemuchiamides A and B, Proline-Rich Linear Lipopeptides, Isolated from a Marine <i>Hormoscilla</i> sp. Cyanobacterium.","authors":"Kensuke Irie, Ghulam Jeelani, Tomoyoshi Nozaki, Arihiro Iwasaki","doi":"10.1021/acs.jnatprod.4c00733","DOIUrl":"10.1021/acs.jnatprod.4c00733","url":null,"abstract":"<p><p>Pemuchiamides A and B (<b>1</b> and <b>2</b>) were isolated from a marine <i>Hormoscilla</i> sp. cyanobacterium collected from Pemuchi Beach on Hateruma Island, Japan. Although <b>1</b> and <b>2</b> existed as a complex mixture of rotamers in chloroform-<i>d</i>, detailed analyses of their 2D NMR and tandem mass spectra revealed their planar structures, respectively. The absolute configurations of <b>1</b> and <b>2</b> were established via the degradation and derivatization reactions. Pemuchiamide A (<b>1</b>) exhibited potent growth-inhibitory activity against <i>Trypanosoma brucei rhodesiense</i>, the causative organism of African sleeping sickness, while <b>2</b> showed 10-fold weaker activity than <b>1</b>. This result indicates that the presence of a hydroxy group at the C-3 position of the 4-aminobutanoic acid moiety negatively affects antitrypanosomal activity.</p>","PeriodicalId":47,"journal":{"name":"Journal of Natural Products ","volume":" ","pages":"2292-2301"},"PeriodicalIF":3.3,"publicationDate":"2024-09-27","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"141981197","PeriodicalName":null,"FirstCategoryId":null,"ListUrlMain":null,"RegionNum":2,"RegionCategory":"生物学","ArticlePicture":[],"TitleCN":null,"AbstractTextCN":null,"PMCID":"","EPubDate":null,"PubModel":null,"JCR":null,"JCRName":null,"Score":null,"Total":0}
引用次数: 0
Characterization of a Xylosyltransferase from Panax notoginseng Catalyzing Ginsenoside 2'-O Glycosylation in the Biosynthesis of Notoginsenosides. 三七中催化人参皂苷 2'-O 糖基化的木糖基转移酶在三七皂苷生物合成过程中的特性。
IF 3.3 2区 生物学
Journal of Natural Products Pub Date : 2024-09-27 Epub Date: 2024-08-27 DOI: 10.1021/acs.jnatprod.4c00298
Rong Liu, Xiaoyi Wu, Zhouqian Jiang, Xuan Liu, Yifeng Zhang, Huan Zhao, Jie Gao, Wei Gao, Yating Hu, Luqi Huang
{"title":"Characterization of a Xylosyltransferase from <i>Panax notoginseng</i> Catalyzing Ginsenoside 2'-<i>O</i> Glycosylation in the Biosynthesis of Notoginsenosides.","authors":"Rong Liu, Xiaoyi Wu, Zhouqian Jiang, Xuan Liu, Yifeng Zhang, Huan Zhao, Jie Gao, Wei Gao, Yating Hu, Luqi Huang","doi":"10.1021/acs.jnatprod.4c00298","DOIUrl":"10.1021/acs.jnatprod.4c00298","url":null,"abstract":"<p><p>Notoginsenosides are important bioactive compounds from <i>Panax notoginseng</i> (Burk.) F. H. Chen, most of which have xylose in their sugar chains. However, the xylosyltransferases involved in the generation of notoginsenosides remain poorly understood, posing a bottleneck for further study of the biosynthesis of notoginsenosides. In this work, a new xylosyltransferase gene, <i>PnUGT57</i> (named <i>UGT94BW1</i>), was identified from <i>P. notoginseng</i>, which has a distinct sequence and could catalyze the 2'-<i>O</i> glycosylation of ginsenosides Rh1 and Rg1 to produce notoginsenosides R2 and R1, respectively. We first characterized the optimal conditions for the <i>Pn</i>UGT57 activity and its enzymatic kinetic parameters, and then, molecular docking and site-directed mutagenesis were performed to elucidate the catalytic mechanism of <i>Pn</i>UGT57. Combined with the results of site-directed mutagenesis, Glu26, Ser266, Glu267, Trp347, Ser348, and Glu352 in <i>Pn</i>UGT57 were identified as the key residues involved in 2'-<i>O</i> glycosylation of C-6 O-Glc, and <i>Pn</i>UGT57<sup>R175A</sup> and <i>Pn</i>UGT57<sup>G237A</sup> could significantly improve the catalytic activity of <i>Pn</i>UGT57. These findings not only provide a new xylosyltransferase gene for augmenting the plant xylosyltransferase database but also identify the pivotal sites and catalytic mechanism of the enzyme, which would provide reference for the modification and application of xylosyltransferases in the future.</p>","PeriodicalId":47,"journal":{"name":"Journal of Natural Products ","volume":" ","pages":"2160-2169"},"PeriodicalIF":3.3,"publicationDate":"2024-09-27","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"142071403","PeriodicalName":null,"FirstCategoryId":null,"ListUrlMain":null,"RegionNum":2,"RegionCategory":"生物学","ArticlePicture":[],"TitleCN":null,"AbstractTextCN":null,"PMCID":"","EPubDate":null,"PubModel":null,"JCR":null,"JCRName":null,"Score":null,"Total":0}
引用次数: 0
Stereoselective Oxidation of α-Copaene, a Fire Ant Repellent Sesquiterpene from the Essential Oil of Dipterocarpus turbinatus. α-槐烯的立体选择性氧化,α-槐烯是一种来自双齿桉树精油的驱火蚁倍半萜。
IF 3.3 2区 生物学
Journal of Natural Products Pub Date : 2024-09-27 Epub Date: 2024-08-28 DOI: 10.1021/acs.jnatprod.4c00758
Ginson George, Farhan Mahmood Shah, Abbas Ali, Dileep Kumar Guddeti, Noura Alowaifi, Joseph Lee, Jian Chen, Ikhlas A Khan, Xing-Cong Li
{"title":"Stereoselective Oxidation of α-Copaene, a Fire Ant Repellent Sesquiterpene from the Essential Oil of <i>Dipterocarpus turbinatus</i>.","authors":"Ginson George, Farhan Mahmood Shah, Abbas Ali, Dileep Kumar Guddeti, Noura Alowaifi, Joseph Lee, Jian Chen, Ikhlas A Khan, Xing-Cong Li","doi":"10.1021/acs.jnatprod.4c00758","DOIUrl":"10.1021/acs.jnatprod.4c00758","url":null,"abstract":"<p><p>Imported fire ants are significant agricultural pests. Repellents can be used to prevent foraging fire ants from entering sensitive areas, including electrical equipment, nursing homes, and hospitals. Bioassay-guided fractionation of the essential oil extracted from gurjun balsam (<i>Dipterocarpus turbinatus</i>) resulted in the identification of (-)-α-copaene (<b>1</b>) as the repellent constituent with a minimum repellent effective dose (MRED) of 15.6 μg/g against both red imported fire ants (<i>Solenopsis invicta</i>) and hybrid imported fire ants (<i>Solenopsis invicta</i> × <i>Solenopsis richteri</i>). Stereoselective oxidation of <b>1</b> via autoxidation and chemical methods produced (-)-5<i>R</i>-hydroperoxy-α-copaene (<b>2</b>), (+)-3<i>S</i>-hydroperoxycopa-4-ene (<b>3</b>), (-)-α-copaene oxide (<b>4</b>), (+)-β-copaen-4α-ol (<b>5</b>), copaenediol (<b>6</b>), and copaene ketol (<b>7</b>). Reduction of <b>2</b> and <b>3</b> with triphenylphosphine afforded (-)-5<i>R</i>-hydroxy-α-copaene (<b>2a</b>) and (+)-3<i>S</i>-hydroxycopa-4-ene (<b>3a</b>), respectively, which led to the structural revision of copa-3-en-2α-ol and copa-2-en-4-ol as <b>2a</b> and <b>3</b>, respectively. The configurational assignment of compound <b>4</b> in the literature was also clarified by the detailed analysis of 2D NMR spectroscopic data. Compounds <b>2</b>-<b>7</b> showed repellency with MREDs ranging from 3.9 to 15.6 μg/g against hybrid and red imported fire ants, indicating that chemical modification can enhance the repellent effect of (-)-α-copaene.</p>","PeriodicalId":47,"journal":{"name":"Journal of Natural Products ","volume":" ","pages":"2302-2309"},"PeriodicalIF":3.3,"publicationDate":"2024-09-27","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"142085890","PeriodicalName":null,"FirstCategoryId":null,"ListUrlMain":null,"RegionNum":2,"RegionCategory":"生物学","ArticlePicture":[],"TitleCN":null,"AbstractTextCN":null,"PMCID":"","EPubDate":null,"PubModel":null,"JCR":null,"JCRName":null,"Score":null,"Total":0}
引用次数: 0
CASE-DFT Structure Elucidation of Proton-Deficient Chlorodepsidones from the Indonesian Lichen Teloschistes flavicans and Structure Revision of Flavicansone. CASE-DFT 印度尼西亚地衣中缺失质子的 Chlorodepsidones 的结构解析及 Flavicansone 的结构修订。
IF 3.3 2区 生物学
Journal of Natural Products Pub Date : 2024-09-27 Epub Date: 2024-05-23 DOI: 10.1021/acs.jnatprod.4c00277
Solenn Ferron, Friardi Ismed, Mikhail E Elyashberg, Alexei V Buevich, Nurwahidatul Arifa, Joël Boustie, Philippe Uriac, Pierre Le Pogam, Françoise Le Dévéhat
{"title":"CASE-DFT Structure Elucidation of Proton-Deficient Chlorodepsidones from the Indonesian Lichen <i>Teloschistes flavicans</i> and Structure Revision of Flavicansone.","authors":"Solenn Ferron, Friardi Ismed, Mikhail E Elyashberg, Alexei V Buevich, Nurwahidatul Arifa, Joël Boustie, Philippe Uriac, Pierre Le Pogam, Françoise Le Dévéhat","doi":"10.1021/acs.jnatprod.4c00277","DOIUrl":"10.1021/acs.jnatprod.4c00277","url":null,"abstract":"<p><p>Biodiscovery efforts in Indonesia have aimed to explore the understudied chemical diversity of its rich lichen flora, seeking to find new products endowed with significant biological properties. The chemical screening of a <i>Teloschistes flavicans</i> extract led to selection of this species for further investigation. LC/MS and <sup>1</sup>H NMR-based dereplication pinpointed six chlorodepsidones from the thallus of a sample of this lichen. This led to the streamlined isolation and the subsequent structure elucidation of the three new compounds norflavicansone <b>1</b>, flavicansone <b>2</b>, and isocaloploicin <b>3</b>, along with the known chlorodepsidones <b>4</b>-<b>6</b>, stictic acid <b>7</b>, aurantiamide acetate <b>8</b>, and parietin <b>9</b>. The challenging structure elucidation of these proton-deficient metabolites benefited from a state-of-the-art workflow involving a synergistic combination of Computer-Assisted Structure Elucidation (CASE) and Density Functional Theory (DFT) calculations of the top-ranked candidates. This investigation also led to the revision of flavicansone's structure, previously described from this species. The three new molecules that are being reported here are remarkable in that they represent hybrid depsidones in which one of the aromatic rings is derived from orsellinic acid and the other is derived from β-orcinol, a rare structural feature for lichen depsidones.</p>","PeriodicalId":47,"journal":{"name":"Journal of Natural Products ","volume":" ","pages":"2148-2159"},"PeriodicalIF":3.3,"publicationDate":"2024-09-27","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"141079790","PeriodicalName":null,"FirstCategoryId":null,"ListUrlMain":null,"RegionNum":2,"RegionCategory":"生物学","ArticlePicture":[],"TitleCN":null,"AbstractTextCN":null,"PMCID":"","EPubDate":null,"PubModel":null,"JCR":null,"JCRName":null,"Score":null,"Total":0}
引用次数: 0
Natural and Bioinspired Lipidic Alkynylcarbinols as Leishmanicidal, Antiplasmodial, Trypanocidal, Fungicidal, Antibacterial, and Antimycobacterial Agents 作为利什曼杀菌剂、抗原虫剂、杀锥虫剂、杀真菌剂、抗菌剂和抗霉菌剂的天然和生物脂类炔基碳水化合物
IF 5.1 2区 生物学
Journal of Natural Products Pub Date : 2024-09-20 DOI: 10.1021/acs.jnatprod.4c00513
Jon Bouvet, Valérie Maraval, Stéphanie Ballereau, Vania Bernardes-Génisson, Yves Génisson
{"title":"Natural and Bioinspired Lipidic Alkynylcarbinols as Leishmanicidal, Antiplasmodial, Trypanocidal, Fungicidal, Antibacterial, and Antimycobacterial Agents","authors":"Jon Bouvet, Valérie Maraval, Stéphanie Ballereau, Vania Bernardes-Génisson, Yves Génisson","doi":"10.1021/acs.jnatprod.4c00513","DOIUrl":"https://doi.org/10.1021/acs.jnatprod.4c00513","url":null,"abstract":"The present review article recapitulates for the first time the antipathogenic biological data of a series of lipidic natural products and synthetic analogues thereof characterized by the presence in their structure of an alkynylcarbinol unit. The cytotoxic properties of such natural and bioinspired compounds have been covered by several literature overviews, but to date, no review article detailing their activity against pathogens has been proposed. This article thus aims at providing a comprehensive overview of the field including early studies from the 1970s and 1980s with a specific focus on results published from the late 1990s until nowadays. Publications presenting the data of almost 50 different natural products are reported. Detailed activities encompass the fields of leishmanicidal, antiplasmodial, trypanocidal, fungicidal, and mainly antibacterial and antimycobacterial compounds. The few published studies aimed at exploring the structure–activity relationship in these series are also described. Around 15 different synthetic analogues of natural products, selected among the most active reported, are also presented. The rare data available regarding the antipathogenic mode of action of these products are recalled, and finally, a comparative analysis of the available biological data is proposed with the aim of identifying the key structural determinants for the bioactivity against pathogens of these unusual compounds.","PeriodicalId":47,"journal":{"name":"Journal of Natural Products ","volume":"52 1","pages":""},"PeriodicalIF":5.1,"publicationDate":"2024-09-20","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"142247430","PeriodicalName":null,"FirstCategoryId":null,"ListUrlMain":null,"RegionNum":2,"RegionCategory":"生物学","ArticlePicture":[],"TitleCN":null,"AbstractTextCN":null,"PMCID":"","EPubDate":null,"PubModel":null,"JCR":null,"JCRName":null,"Score":null,"Total":0}
引用次数: 0
Discovery, Biosynthesis, and Characterization of Rodencin, a Two-Component Lanthipeptide, Harboring d-Amino Acids Introduced by the Unusual Dehydrogenase RodJA 发现、生物合成和表征含有由非同寻常的脱氢酶 RodJA 引入的 d-Aminoids 的双组分肽--Rodencin
IF 5.1 2区 生物学
Journal of Natural Products Pub Date : 2024-09-20 DOI: 10.1021/acs.jnatprod.4c00170
Yuxin Fu, Eleftheria Pateri, Oscar P. Kuipers
{"title":"Discovery, Biosynthesis, and Characterization of Rodencin, a Two-Component Lanthipeptide, Harboring d-Amino Acids Introduced by the Unusual Dehydrogenase RodJA","authors":"Yuxin Fu, Eleftheria Pateri, Oscar P. Kuipers","doi":"10.1021/acs.jnatprod.4c00170","DOIUrl":"https://doi.org/10.1021/acs.jnatprod.4c00170","url":null,"abstract":"Lanthipeptides, a group of ribosomally synthesized and post-translationally modified peptides (RiPPs), exhibit diverse structures and bioactivities. Their biosynthetic enzymes serve as valuable tools for peptide bioengineering. Here, we report a class II lanthipeptide biosynthetic gene cluster in a <i>Bacillus</i> strain, driving the biosynthesis of a two-component lanthipeptide, termed rodencin, featured by the presence of two different <span>d</span>-amino acids, i.e., <span>d</span>-Ala and <span>d</span>-Abu. Rodencin displays synergistic antimicrobial activity against food-borne pathogens such as <i>Bacillus cereus</i>, <i>Staphylococcus aureus</i>, and <i>Listeria monocytogenes</i>. The α-peptide of rodencin contains one <span>d</span>-Ala and the β-peptide features both <span>d</span>-Ala and <span>d</span>-Abu. These are installed by dehydratases RodM1 and RodM2 and dehydrogenase RodJ<sub>A</sub>, the activities of which were successfully reconstituted using a dedicated <i>E. coli</i> expression system. To illustrate the unusual <span>d</span>-Abu incorporation potential of the enzymes, analogous to the <span>d</span>-amino acid-containing β peptide of lacticin 3147, was successfully produced with the rodencin heterologous expression system, by employing RodM2 and the dehydrogenase RodJ<sub>A</sub>.","PeriodicalId":47,"journal":{"name":"Journal of Natural Products ","volume":"7 1","pages":""},"PeriodicalIF":5.1,"publicationDate":"2024-09-20","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"142247428","PeriodicalName":null,"FirstCategoryId":null,"ListUrlMain":null,"RegionNum":2,"RegionCategory":"生物学","ArticlePicture":[],"TitleCN":null,"AbstractTextCN":null,"PMCID":"","EPubDate":null,"PubModel":null,"JCR":null,"JCRName":null,"Score":null,"Total":0}
引用次数: 0
Medullins A-H, Sesquiterpenes from Perenniporia medulla-panis, and Their Cellular Signaling Mechanism in HDF Cells 髓苷 A-H(来自秘鲁髓苷的倍半萜)及其在 HDF 细胞中的细胞信号机制
IF 5.1 2区 生物学
Journal of Natural Products Pub Date : 2024-09-18 DOI: 10.1021/acs.jnatprod.4c00436
Dae-Won Ki, Ji-Yul Kim, Young-Hee Lee, Dae-Cheol Choi, Ho-Keun Yi, In-Kyoung Lee, Bong-Sik Yun
{"title":"Medullins A-H, Sesquiterpenes from Perenniporia medulla-panis, and Their Cellular Signaling Mechanism in HDF Cells","authors":"Dae-Won Ki, Ji-Yul Kim, Young-Hee Lee, Dae-Cheol Choi, Ho-Keun Yi, In-Kyoung Lee, Bong-Sik Yun","doi":"10.1021/acs.jnatprod.4c00436","DOIUrl":"https://doi.org/10.1021/acs.jnatprod.4c00436","url":null,"abstract":"A chemical investigation of an ethyl acetate-soluble layer in the culture broth of <i>Perenniporia medulla-panis</i> resulted in the isolation of eight novel sesquiterpenes conjugated Gly (<b>1</b>), <span>l</span>-Val (<b>2</b>), <span>l</span>-Ala (<b>3</b>), <span>l</span>-Tyr (<b>4</b>), <span>l</span>-Thr (<b>5</b>), <span>l</span>-Ile (<b>6</b>), <span>l</span>-Leu (<b>7</b>), and <span>l</span>-Phe (<b>8</b>). Elucidation of their structures was performed through comprehensive spectroscopic analysis. The absolute configuration of the sesquiterpene skeleton was ascertained using modified Mosher’s methods. The configurations of the amino acid units in compounds <b>2</b>–<b>8</b> were identified through acid hydrolysis followed by LC-MS analysis employing Marfey’s method. Compounds <b>1</b>–<b>3</b> and <b>5</b>–<b>8</b> showed significant regulating effect on MAP kinase activity (p-ERK and p-JNK) in human diploid fibroblast (HDF) cells.","PeriodicalId":47,"journal":{"name":"Journal of Natural Products ","volume":"13 1","pages":""},"PeriodicalIF":5.1,"publicationDate":"2024-09-18","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"142247431","PeriodicalName":null,"FirstCategoryId":null,"ListUrlMain":null,"RegionNum":2,"RegionCategory":"生物学","ArticlePicture":[],"TitleCN":null,"AbstractTextCN":null,"PMCID":"","EPubDate":null,"PubModel":null,"JCR":null,"JCRName":null,"Score":null,"Total":0}
引用次数: 0
Medullins A-H, Sesquiterpenes from Perenniporia medulla-panis, and Their Cellular Signaling Mechanism in HDF Cells 髓苷 A-H(来自秘鲁髓苷的倍半萜)及其在 HDF 细胞中的细胞信号机制
IF 3.3 2区 生物学
Journal of Natural Products Pub Date : 2024-09-18 DOI: 10.1021/acs.jnatprod.4c0043610.1021/acs.jnatprod.4c00436
Dae-Won Ki*, Ji-Yul Kim, Young-Hee Lee, Dae-Cheol Choi, Ho-Keun Yi, In-Kyoung Lee and Bong-Sik Yun*, 
{"title":"Medullins A-H, Sesquiterpenes from Perenniporia medulla-panis, and Their Cellular Signaling Mechanism in HDF Cells","authors":"Dae-Won Ki*,&nbsp;Ji-Yul Kim,&nbsp;Young-Hee Lee,&nbsp;Dae-Cheol Choi,&nbsp;Ho-Keun Yi,&nbsp;In-Kyoung Lee and Bong-Sik Yun*,&nbsp;","doi":"10.1021/acs.jnatprod.4c0043610.1021/acs.jnatprod.4c00436","DOIUrl":"https://doi.org/10.1021/acs.jnatprod.4c00436https://doi.org/10.1021/acs.jnatprod.4c00436","url":null,"abstract":"<p >A chemical investigation of an ethyl acetate-soluble layer in the culture broth of <i>Perenniporia medulla-panis</i> resulted in the isolation of eight novel sesquiterpenes conjugated Gly (<b>1</b>), <span>l</span>-Val (<b>2</b>), <span>l</span>-Ala (<b>3</b>), <span>l</span>-Tyr (<b>4</b>), <span>l</span>-Thr (<b>5</b>), <span>l</span>-Ile (<b>6</b>), <span>l</span>-Leu (<b>7</b>), and <span>l</span>-Phe (<b>8</b>). Elucidation of their structures was performed through comprehensive spectroscopic analysis. The absolute configuration of the sesquiterpene skeleton was ascertained using modified Mosher’s methods. The configurations of the amino acid units in compounds <b>2</b>–<b>8</b> were identified through acid hydrolysis followed by LC-MS analysis employing Marfey’s method. Compounds <b>1</b>–<b>3</b> and <b>5</b>–<b>8</b> showed significant regulating effect on MAP kinase activity (p-ERK and p-JNK) in human diploid fibroblast (HDF) cells.</p>","PeriodicalId":47,"journal":{"name":"Journal of Natural Products ","volume":"87 9","pages":"2194–2203 2194–2203"},"PeriodicalIF":3.3,"publicationDate":"2024-09-18","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"142326308","PeriodicalName":null,"FirstCategoryId":null,"ListUrlMain":null,"RegionNum":2,"RegionCategory":"生物学","ArticlePicture":[],"TitleCN":null,"AbstractTextCN":null,"PMCID":"","EPubDate":null,"PubModel":null,"JCR":null,"JCRName":null,"Score":null,"Total":0}
引用次数: 0
Reaping the Chemical Diversity of Morinagamyces vermicularis Using Feature-Based Molecular Networking 利用基于特征的分子网络收获莫里纳加米氏菌(Marinagamyces vermicularis)的化学多样性
IF 3.3 2区 生物学
Journal of Natural Products Pub Date : 2024-09-15 DOI: 10.1021/acs.jnatprod.4c0065410.1021/acs.jnatprod.4c00654
Karen Harms, Esteban Charria-Girón, Alberto Miguel Stchigel, Yasmina Marin-Felix* and Frank Surup*, 
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