Journal of Natural Products 最新文献

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Schinortriterpenoids with an Unprecedented Oxatricyclo[4.2.1.04,8]nonane Bridged System from Schisandra chinensis [4.2.1.04,8]壬烷桥接五味子三萜类化合物
IF 3.7 2区 生物学
Journal of Natural Products Pub Date : 2026-09-25 Epub Date: 2026-09-02 DOI: 10.1021/acs.jnatprod.6c00640
Peng Jiang, Yu-Meng Luo, Fan-Ying Deng, Shu-Jun Zhang, Yi-Qiang Zhang, Wei Guan, Zhi-Chao Hao, Zhen-Qiang Liu, Yuan-Yuan Zhou, Qing-Shan Chen, Li-Li Zhang, Tian-Gang Lu, Rui-Yan Wu, Peng-Zhou Xi, Yan Liu
{"title":"Schinortriterpenoids with an Unprecedented Oxatricyclo[4.2.1.04,8]nonane Bridged System from Schisandra chinensis","authors":"Peng Jiang,&nbsp;Yu-Meng Luo,&nbsp;Fan-Ying Deng,&nbsp;Shu-Jun Zhang,&nbsp;Yi-Qiang Zhang,&nbsp;Wei Guan,&nbsp;Zhi-Chao Hao,&nbsp;Zhen-Qiang Liu,&nbsp;Yuan-Yuan Zhou,&nbsp;Qing-Shan Chen,&nbsp;Li-Li Zhang,&nbsp;Tian-Gang Lu,&nbsp;Rui-Yan Wu,&nbsp;Peng-Zhou Xi,&nbsp;Yan Liu","doi":"10.1021/acs.jnatprod.6c00640","DOIUrl":"https://doi.org/10.1021/acs.jnatprod.6c00640","url":null,"abstract":"<p>Six new schinortriterpenoids (SNTs), including one structurally unique SNT featuring a caged oxatricyclo[4.2.1.0<sup>4,8</sup>]nonane bridged system (<strong>1</strong>) and five previously undescribed SNTs (<strong>2</strong>−<strong>6</strong>), were isolated from the fruits of <em>Schisandra chinensis</em>. The structures and configurations of compounds <strong>1</strong>−<strong>6</strong> were elucidated via comprehensive spectroscopic analysis, nuclear magnetic resonance (NMR) calculations, DP4+ analysis, electronic circular dichroism (ECD) calculations, and single-crystal X-ray diffraction. All compounds were evaluated for their neuroprotective activity against H<sub>2</sub>O<sub>2</sub>-induced injury in PC12 cells, and compound <strong>1</strong> exhibited potent neuroprotective activity, with an EC<sub>50</sub> value of 1.02 ± 0.18 μM. Nuclear receptor subfamily 3 group C member 2 (NR3C2) was identified as a potential target through which compound <strong>1</strong> exerts its neuroprotective effect through virtual screening, molecular dynamics (MD) simulation, and experimental validation. The discovery of compound <strong>1</strong> broadens the chemical diversity of known SNTs and provides a novel bioactive scaffold for natural product development.</p>","PeriodicalId":47,"journal":{"name":"Journal of Natural Products ","volume":"89 9","pages":"2513–2526"},"PeriodicalIF":3.7,"publicationDate":"2026-09-25","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"149152835","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
α-Synuclein Binding Alkaloids from the Australian Bryozoan Amathia tricornis 澳洲苔藓虫Amathia tricornis α-Synuclein结合生物碱
IF 3.7 2区 生物学
Journal of Natural Products Pub Date : 2026-09-25 Epub Date: 2026-09-02 DOI: 10.1021/acs.jnatprod.6c00883
Francesca Ferretti, Joshua B. Hayton, George D. Mellick, Anthony R. Carroll
{"title":"α-Synuclein Binding Alkaloids from the Australian Bryozoan Amathia tricornis","authors":"Francesca Ferretti,&nbsp;Joshua B. Hayton,&nbsp;George D. Mellick,&nbsp;Anthony R. Carroll","doi":"10.1021/acs.jnatprod.6c00883","DOIUrl":"https://doi.org/10.1021/acs.jnatprod.6c00883","url":null,"abstract":"<p>In this study, we conducted the first chemical investigation of the Australian bryozoan <em>Amathia tricornis</em>, leading to the isolation and characterization of 11 new metabolites, including the bromoindoles tricornamines A−E (<strong>1</strong>−<strong>5</strong>), phenethylamine amathamines E−F (<strong>6</strong>−<strong>7</strong>), and guanadino-containing phenethylamides tricornamides A−D (<strong>8</strong>−<strong>11</strong>), together with three known compounds; amathamides E−F (<strong>12</strong>−<strong>13</strong>) and lamourimidazolinium trifluoroacetate (<strong>14</strong>). We also report the binding affinity of <strong>6</strong>, <strong>7</strong>, <strong>9</strong> and <strong>10</strong> to the Parkinson’s disease implicated protein α-synuclein. This has provided new insight into the structure−activity relationships of brominated phenethylamino metabolites towards this neurodegenerative disease-relevant target. The new natural products expand the chemical diversity reported from <em>Amathia</em> species and further support bryozoans as a promising source of unique compounds.</p>","PeriodicalId":47,"journal":{"name":"Journal of Natural Products ","volume":"89 9","pages":"2706–2717"},"PeriodicalIF":3.7,"publicationDate":"2026-09-25","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"149152836","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
Structural Revision of Natural Dibenzofurans Based on Their Spectroscopic Characteristics 基于光谱特征的天然二苯并呋喃结构修正
IF 3.7 2区 生物学
Journal of Natural Products Pub Date : 2026-09-25 Epub Date: 2026-09-01 DOI: 10.1021/acs.jnatprod.6c00685
Yang Gong, Wei-Juan Zu, Xing-Kun Rong, Yi-Ling Yang, Rong Liu, Bei Jiang, Chao-Jiang Xiao
{"title":"Structural Revision of Natural Dibenzofurans Based on Their Spectroscopic Characteristics","authors":"Yang Gong,&nbsp;Wei-Juan Zu,&nbsp;Xing-Kun Rong,&nbsp;Yi-Ling Yang,&nbsp;Rong Liu,&nbsp;Bei Jiang,&nbsp;Chao-Jiang Xiao","doi":"10.1021/acs.jnatprod.6c00685","DOIUrl":"https://doi.org/10.1021/acs.jnatprod.6c00685","url":null,"abstract":"<p>Dibenzofurans are a relatively small but important group of natural products. To better identify, explore, and utilize these compounds, this paper summarizes their spectroscopic characteristics for the first time. A comprehensive analysis was conducted on a total of 208 natural dibenzofurans. The structures of 37 dibenzofurans may have been incorrectly interpreted, of which 30 were revised, with the remaining seven pending identification. Furthermore, the NMR chemical shifts of another 23 dibenzofurans were reassigned or completely assigned.</p>","PeriodicalId":47,"journal":{"name":"Journal of Natural Products ","volume":"89 9","pages":"2582–2602"},"PeriodicalIF":3.7,"publicationDate":"2026-09-25","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"149152899","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
MALDI Tandem Mass Spectrometry for Colony-Based Dereplication of Natural Products MALDI串联质谱法用于天然产物菌落分离
IF 3.7 2区 生物学
Journal of Natural Products Pub Date : 2026-09-25 Epub Date: 2026-08-24 DOI: 10.1021/acs.jnatprod.6c00765
Robert A. Shepherd, Limar Y. Gad, Michael Strobel, Gordon T. Luu, Jin Feng, Carlo De Silva, Shaun M. K. McKinnie, Mingxun Wang, Laura M. Sanchez
{"title":"MALDI Tandem Mass Spectrometry for Colony-Based Dereplication of Natural Products","authors":"Robert A. Shepherd,&nbsp;Limar Y. Gad,&nbsp;Michael Strobel,&nbsp;Gordon T. Luu,&nbsp;Jin Feng,&nbsp;Carlo De Silva,&nbsp;Shaun M. K. McKinnie,&nbsp;Mingxun Wang,&nbsp;Laura M. Sanchez","doi":"10.1021/acs.jnatprod.6c00765","DOIUrl":"https://doi.org/10.1021/acs.jnatprod.6c00765","url":null,"abstract":"<p>Microbial libraries remain an important resource for natural product discovery; however, constructing taxonomically and chemically diverse collections remains a challenge. Advances in dereplication strategies, including molecular networking, have reduced the rediscovery of known bioactive molecules and facilitated the identification of novel chemical scaffolds, but these approaches are typically applied after library construction. Furthermore, many dereplication workflows require fermentation and extraction, increasing the time needed to assess a microbe’s metabolite profile. Here, we integrate matrix-assisted laser desorption/ionization tandem mass spectrometry (MALDI-MS/MS) into the bioinformatics platform IDBac, enabling characterization of microbial taxonomic identity, metabolite production potential, and preliminary metabolite annotation through GNPS2 molecular networking. This workflow facilitates strain prioritization by providing metabolite annotations directly from single microbial colonies prior to scale-up and extraction. Application of this approach to marine actinomycetes enabled the annotation of lavanducyanin and multiple napyradiomycin analogs. Subsequent investigation led to the discovery of napyradiomycin B8 from marine <em>Streptomyces</em> sp. CNZ-289, which was confirmed by 1D and 2D NMR spectroscopy and MALDI-MS/MS. Expanding this workflow to 25 commensal marine vertebrate-derived bacterial isolates resulted in the annotation of known bioactive natural products, including surugamides, antimycins, desferrioxamine siderophores, and the isolation and elucidation of harmane derivatives using NMR.</p>","PeriodicalId":47,"journal":{"name":"Journal of Natural Products ","volume":"89 9","pages":"2643–2655"},"PeriodicalIF":3.7,"publicationDate":"2026-09-25","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"149153034","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
Enzymatic Hydrogen Cyanide Release from Mandelonitrile Esters in Oribatid Mites 甲螨体内曼德拉腈酯酶解氰化氢的研究
IF 3.7 2区 生物学
Journal of Natural Products Pub Date : 2026-09-25 Epub Date: 2026-09-08 DOI: 10.1021/acs.jnatprod.6c00671
Daisuke Moriyama, Chihiro Takahara, Satoshi Shimano, Nobuhiro Shimizu
{"title":"Enzymatic Hydrogen Cyanide Release from Mandelonitrile Esters in Oribatid Mites","authors":"Daisuke Moriyama,&nbsp;Chihiro Takahara,&nbsp;Satoshi Shimano,&nbsp;Nobuhiro Shimizu","doi":"10.1021/acs.jnatprod.6c00671","DOIUrl":"https://doi.org/10.1021/acs.jnatprod.6c00671","url":null,"abstract":"<p>Arthropods use chemical defenses against predators by releasing toxic or repellent compounds from specialized exocrine glands. Oribatulid mites (Oribatida: Oribatulidae) contain mandelonitrile hexanoate (MNH); when they are subjected to physical stimuli, MNH decomposes to release hydrogen cyanide (HCN), suggesting that cyanogenesis is an effective defense strategy in these mites. However, the underlying process remains unclear. Here, we investigated the defensive secretions of the oribatid mites, <em>Phauloppia adjecta</em> and <em>Oribatula sakamorii,</em> and identified MNH and mandelonitrile octanoate (MNO), along with the sesquiterpenes β-selinene and calarene. Chiral gas chromatography analysis determined the absolute configurations of MNH and MNO as the (<em>R</em>)-isomers, consistent with the configuration of mandelonitrile<span></span>a known defensive compound in polydesmid millipedes. (<em>R</em>)-MNO did not undergo spontaneous hydrolysis in water at pH 3−8, suggesting that a mite-derived enzyme is required for HCN production. In vitro experiments showed that a crude mite enzyme extract incubated with (<em>R</em>)-MNO generated over 200 nmol of HCN, whereas negligible production occurred in the controls. These findings support an enzyme-dependent cyanogenic defense mechanism wherein mandelonitrile esters stored in the oil glands release HCN upon enzyme interaction during disturbance, potentially protecting conspecifics from predation.</p>","PeriodicalId":47,"journal":{"name":"Journal of Natural Products ","volume":"89 9","pages":"2527–2535"},"PeriodicalIF":3.7,"publicationDate":"2026-09-25","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"149153036","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
Toluquinol-Derived Meroterpenoids from an Engineered Aspergillus oryzae Harboring Key Biosynthetic Genes from Carnivorous Fungus Arthrobotrys oligospora 含有肉食性真菌寡孢节肢菌关键生物合成基因的工程米曲霉的甲苯醌类衍生物
IF 3.7 2区 生物学
Journal of Natural Products Pub Date : 2026-09-25 Epub Date: 2026-08-24 DOI: 10.1021/acs.jnatprod.6c00697
Rui-Jin Jiang, Dong-Lou Wang, Xiao-Mei Yan, Dao-Sheng Xue, Jia-Hao Gu, Xiao-Xu Bi, Yong-Ming Yan, Ying Wang, Xue-Mei Niu, Jiang-Bo He
{"title":"Toluquinol-Derived Meroterpenoids from an Engineered Aspergillus oryzae Harboring Key Biosynthetic Genes from Carnivorous Fungus Arthrobotrys oligospora","authors":"Rui-Jin Jiang,&nbsp;Dong-Lou Wang,&nbsp;Xiao-Mei Yan,&nbsp;Dao-Sheng Xue,&nbsp;Jia-Hao Gu,&nbsp;Xiao-Xu Bi,&nbsp;Yong-Ming Yan,&nbsp;Ying Wang,&nbsp;Xue-Mei Niu,&nbsp;Jiang-Bo He","doi":"10.1021/acs.jnatprod.6c00697","DOIUrl":"https://doi.org/10.1021/acs.jnatprod.6c00697","url":null,"abstract":"<p>Engineered <em>Aspergillus oryzae</em> strains possessing four biosynthetic genes (<em>AOL_s00215g276</em>−<em>279</em>) from carnivorous fungus <em>Arthrobotrys oligospora</em> enabled the isolation of 17 toluquinol-derived meroterpenoids. Thirteen were previously undescribed, including (±)-spinulinoid G (<strong>1a</strong>/<strong>1b</strong>), (±)-kuhistanol H (<strong>2a</strong>/<strong>2b</strong>), (±)-anthoponoid J (<strong>3a</strong>/<strong>3b</strong>), (±)-anthoponoid K (<strong>4a</strong>/<strong>4b</strong>), (+)-nitrosporeunol E (<strong>5a</strong>), (<em>E</em>)-2-methyl-3′-methoxyfarnesyl toluquinol (<strong>6</strong>), methylfarnesylquinone B (<strong>7</strong>), methylfarnesylquinone C (<strong>8</strong>), and didehydroconicol B (<strong>9</strong>), along with four known analogues (<strong>5b</strong>, <strong>10</strong>−<strong>12</strong>). Their structures were elucidated by extensive spectroscopic analyses, and the absolute configurations were assigned by TDDFT-ECD calculations and/or comparison of optical rotation data with those of structurally related compounds. Several compounds (<strong>2a</strong>, <strong>2b</strong>, <strong>4a</strong>, <strong>10</strong>, and <strong>12</strong>) exhibited cytotoxic activity against human cancer cell lines BGC803, HCT116, MIA PaCa-2, and HeLa. Compound <strong>2b</strong> showed prominent cytotoxicity against HCT116 and HeLa cells, with IC<sub>50</sub> values of 7.69 μM and 5.60 μM, respectively. Furthermore, network pharmacology highlighted compounds <strong>2b</strong> and <strong>4a</strong> and suggested HIF1A and PIK3CA as candidate targets, for which molecular docking predicted plausible binding modes. These findings expand meroterpenoid structural diversity and provide promising small-molecule scaffolds for anticancer lead development.</p>","PeriodicalId":47,"journal":{"name":"Journal of Natural Products ","volume":"89 9","pages":"2582–2602"},"PeriodicalIF":3.7,"publicationDate":"2026-09-25","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"149153043","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
Differentiating 5-Thiooxazoles from Oxazolone-Coupled Thioamides in RiPP Natural Products RiPP天然产物中5-硫代唑与恶唑酮偶联硫酰胺的鉴别
IF 3.7 2区 生物学
Journal of Natural Products Pub Date : 2026-09-25 Epub Date: 2026-08-12 DOI: 10.1021/acs.jnatprod.6c00701
Olivia M. Manley, Tucker J. Shriver, José M. Ayala, Benjamin C. Owen, Joshua J. Ziarek, Amy C. Rosenzweig
{"title":"Differentiating 5-Thiooxazoles from Oxazolone-Coupled Thioamides in RiPP Natural Products","authors":"Olivia M. Manley,&nbsp;Tucker J. Shriver,&nbsp;José M. Ayala,&nbsp;Benjamin C. Owen,&nbsp;Joshua J. Ziarek,&nbsp;Amy C. Rosenzweig","doi":"10.1021/acs.jnatprod.6c00701","DOIUrl":"https://doi.org/10.1021/acs.jnatprod.6c00701","url":null,"abstract":"<p>Conversion of cysteine residues to 5-thiooxazole moieties by multinuclear nonheme iron-dependent oxidative enzymes (MNIOs) is a prevalent modification in ribosomally synthesized, post-translationally modified peptide (RiPP) natural products. However, this post-translational modification (PTM) is difficult to distinguish from MNIO-produced oxazolone-coupled thioamides, such as those present in the RiPP methanobactin. The RiPP virulence factor oxazolin contains six copper-binding heterocycles installed by an MNIO. Here, we reassign these PTMs, originally described as oxazolones/thioamides, as 5-thiooxazoles on the basis of detailed comparative chemical and structural characterization of oxazolin and methanobactin. These data establish a benchmark for differentiating these two PTMs in newly discovered RiPPs.</p>","PeriodicalId":47,"journal":{"name":"Journal of Natural Products ","volume":"89 9","pages":"2734–2740"},"PeriodicalIF":3.7,"publicationDate":"2026-09-25","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"149153106","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
A Penta-Thiooxazole RiPP Confers Periplasmic Defense to Oxidative Stress in Pseudomonas aeruginosa 五硫恶唑RiPP对铜绿假单胞菌氧化应激的质周防御作用
IF 3.7 2区 生物学
Journal of Natural Products Pub Date : 2026-09-25 Epub Date: 2026-08-24 DOI: 10.1021/acs.jnatprod.6c00542
Zhuangzhuang Chu, Hanzhong Feng, Hang Xu, Xuelin Li, Jun Hou, XinXiang Lei, Yong Wang, Yong-Xing He
{"title":"A Penta-Thiooxazole RiPP Confers Periplasmic Defense to Oxidative Stress in Pseudomonas aeruginosa","authors":"Zhuangzhuang Chu,&nbsp;Hanzhong Feng,&nbsp;Hang Xu,&nbsp;Xuelin Li,&nbsp;Jun Hou,&nbsp;XinXiang Lei,&nbsp;Yong Wang,&nbsp;Yong-Xing He","doi":"10.1021/acs.jnatprod.6c00542","DOIUrl":"https://doi.org/10.1021/acs.jnatprod.6c00542","url":null,"abstract":"<p>Multinuclear non-heme iron-dependent oxidases (MNIOs) constitute an emerging family of post-translational modifying enzymes that catalyze atypical modifications. Despite their widespread distribution across bacteria, only a small number of MNIO family members have been biochemically characterized, and the catalytic capabilities, product structures, and physiological functions of the vast majority remain unexplored. Here, we report the discovery and characterization of <em>aen</em> gene cluster, a previously uncharacterized MNIO-associated gene cluster in the opportunistic pathogen <em>Pseudomonas aeruginosa</em> PAO1. We demonstrate that the AenBC enzyme complex catalyzes four-electron oxidation of all five cysteine residues in the precursor peptide AenA, yielding a mature product, aeruginin, whose cysteine-derived modifications are most consistent with five 5-thiooxazole motifs. Under competitive metal incubation conditions, HR-MS analysis revealed that aeruginin preferentially associates with Fe<sup>3+</sup> rather than copper. Functional analyses reveal that deletion of <em>aenA</em> results in a highly specific growth defect under chlorite stress, accompanied by significant upregulation of the periplasmic disulfide isomerase DsbG. Together, these findings expand the known structural diversity of MNIO-derived RiPPs and suggest a potential role for aeruginin in chlorite responsive periplasmic stress adaptation.</p>","PeriodicalId":47,"journal":{"name":"Journal of Natural Products ","volume":"89 9","pages":"2462–2473"},"PeriodicalIF":3.7,"publicationDate":"2026-09-25","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"149153033","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
Unravelling the Enantiomeric Distribution of Key Sandalwood Sesquiterpenoids by Enantioselective Gas Chromatography and Molecular Rotational Resonance 对映选择气相色谱和分子旋转共振揭示檀香主要倍半萜的对映体分布
IF 3.7 2区 生物学
Journal of Natural Products Pub Date : 2026-09-25 Epub Date: 2026-09-04 DOI: 10.1021/acs.jnatprod.6c00530
Cecilia L. Cagliero, Reilly E. Sonstrom, Carlo Bicchi, Norbert A. Braun, Daniel Joulain, Nicolas Baldovini
{"title":"Unravelling the Enantiomeric Distribution of Key Sandalwood Sesquiterpenoids by Enantioselective Gas Chromatography and Molecular Rotational Resonance","authors":"Cecilia L. Cagliero,&nbsp;Reilly E. Sonstrom,&nbsp;Carlo Bicchi,&nbsp;Norbert A. Braun,&nbsp;Daniel Joulain,&nbsp;Nicolas Baldovini","doi":"10.1021/acs.jnatprod.6c00530","DOIUrl":"https://doi.org/10.1021/acs.jnatprod.6c00530","url":null,"abstract":"<p>The enantiomeric distribution of α- and β-santalol in various <em>Santalum</em> and <em>Osyris</em> species of different origins was determined by the combination of enantioselective gas chromatography and chiral tagging molecular rotational resonance spectroscopy, supported by the preparation of (+)- and (−)-α-santalol standards by total synthesis and isolation of (−)-β-santalol from <em>Santalum album </em>essential oil. (−)-β-Santalol was largely dominant in all <em>Santalum</em> essential oil samples (&gt;99%) except for the mixtures of santalols produced by biotechnology. The enantiomeric distribution of α-santalol was much less in favor of the levorotatory enantiomer, contained in percentages up to 5 and 45% in some <em>Santalum</em> and <em>Osyris</em> samples, respectively. The olfactory evaluations of synthetic (+)- and (−)-α-santalol samples by a panel of 56 assessors showed that they were very weak to odorless for most panelists.</p>","PeriodicalId":47,"journal":{"name":"Journal of Natural Products ","volume":"89 9","pages":"2452–2461"},"PeriodicalIF":3.7,"publicationDate":"2026-09-25","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"149153151","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
Starter Unit Promiscuity of Dictyostelid Type III Polyketide Synthases Generates Diverse Acylphloroglucinols with Antimicrobial Activity Dictyostelid III型聚酮合酶的起始单元混杂产生多种具有抗菌活性的酰基间苯三酚
IF 3.7 2区 生物学
Journal of Natural Products Pub Date : 2026-09-25 Epub Date: 2026-08-07 DOI: 10.1021/acs.jnatprod.6c00631
Nattapong Dedkad, Sukhita Sathitnaitham, Kamonchat Prommarit, Thanyaporn Chittavichai, Supanut Utthiya, Wanchat Sirisarn, Piyangkun Lueangjaroenkit, Supachai Vuttipongchaikij, Passorn Wonnapinij, Pakorn Wattana-Amorn
{"title":"Starter Unit Promiscuity of Dictyostelid Type III Polyketide Synthases Generates Diverse Acylphloroglucinols with Antimicrobial Activity","authors":"Nattapong Dedkad,&nbsp;Sukhita Sathitnaitham,&nbsp;Kamonchat Prommarit,&nbsp;Thanyaporn Chittavichai,&nbsp;Supanut Utthiya,&nbsp;Wanchat Sirisarn,&nbsp;Piyangkun Lueangjaroenkit,&nbsp;Supachai Vuttipongchaikij,&nbsp;Passorn Wonnapinij,&nbsp;Pakorn Wattana-Amorn","doi":"10.1021/acs.jnatprod.6c00631","DOIUrl":"https://doi.org/10.1021/acs.jnatprod.6c00631","url":null,"abstract":"<p><em>Cavenderia subdiscoidea</em> and <em>Cavenderia ungulata</em> are dictyostelid social amoebae found in northern Thailand. Genomic analysis identified two type III polyketide synthase genes, designated <em>cspks</em> and <em>cupks</em>. Heterologous expression of both genes in <em>Aspergillus oryzae</em> NSAR1 yielded a variety of acylphloroglucinols derived from different starter units. Among these were cavenderic acids A−E (<strong>1−5</strong>) and two related ester derivatives (<strong>6−7</strong>). Compounds <strong>1</strong> and <strong>2</strong> are reported here for the first time as natural products, whereas compounds <strong>3−7</strong> are new compounds. Structural analysis suggested that compounds <strong>1−7</strong> are biosynthetically derived from C4−C10 α,ω-dicarboxylic acid CoA thioesters, representing a putative and unprecedented starter-unit class for type III PKSs. Additionally, four known acylphloroglucinols (<strong>8−10</strong> and <strong>12</strong>) and one new derivative (<strong>11</strong>), derived from saturated and unsaturated fatty acid starter units, were identified. These findings demonstrate the broad starter-unit promiscuity of <em>Cavenderia</em> type III PKSs and their ability to generate structurally diverse acylphloroglucinols when expressed in a heterologous host. Compounds <strong>1</strong>, <strong>3−4</strong>, and <strong>8−11</strong> were evaluated for antimicrobial activity. Compound <strong>8</strong> (jambone C) exhibited the strongest antibacterial activity against several Gram-positive bacteria. Comparison of the tested compounds further suggested that terminal polar functional groups reduced antibacterial activity, providing preliminary structure−activity relationship insights for acylphloroglucinols.</p>","PeriodicalId":47,"journal":{"name":"Journal of Natural Products ","volume":"89 9","pages":"2486–2501"},"PeriodicalIF":3.7,"publicationDate":"2026-09-25","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"149153132","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}
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