Journal of Natural Products 最新文献

筛选
英文 中文
Cyclitols and Aminocyclitols as Signals: Their Roles in Supporting Ecosystems and Promoting Human Health 环醇和氨基环醇作为信号:它们在支持生态系统和促进人类健康中的作用。
IF 3.7 2区 生物学
Journal of Natural Products Pub Date : 2026-08-28 Epub Date: 2026-02-04 DOI: 10.1021/acs.jnatprod.5c01437
Leigh Skala, Patrick K. Murdach, Taylor Hennelly, Taifo Mahmud
{"title":"Cyclitols and Aminocyclitols as Signals: Their Roles in Supporting Ecosystems and Promoting Human Health","authors":"Leigh Skala,&nbsp;Patrick K. Murdach,&nbsp;Taylor Hennelly,&nbsp;Taifo Mahmud","doi":"10.1021/acs.jnatprod.5c01437","DOIUrl":"10.1021/acs.jnatprod.5c01437","url":null,"abstract":"<p>Secondary metabolites (a.k.a. natural products) are believedtoplay beneficial roles for the producing organisms, such as copingwith environmental stress or outcompeting other organisms. Some ofthem may function as signals. One such class of natural products isthe cyclitol/aminocyclitol family of compounds, which includes <em>myo</em>-inositol and its derivatives, the aminoglycoside antibiotics,and the C<sub>7</sub>-cyclitols and C<sub>7</sub>N-aminocyclitols.While the function of inositol and its derivatives as intracellularsignaling molecules has been well established, more recent studieshave also demonstrated their important ecological roles. Studies havealso shown that aminoglycoside antibiotics may function as signalsthat regulate biofilm formation in bacteria and secondary metaboliteproduction in fungi. Several C<sub>7</sub>-cyclitols and C<sub>7</sub>N-aminocyclitols, <em>e.g</em>., acarbose, validamycin, andkirkamide, have been associated with gut microbiota modulation, generegulation in fungi and insects, and/or plant–bacteria endosymbiosis.While mycosporine-like amino acids (MAAs) are well known for theirUV-protective activities, studies with human cells and animals haveshown intriguing biological activities involving gene regulation andactivation of signaling pathways. This article reviews the roles ofthis family of natural products as signaling molecules involved invarious biological events, including bacterial colonization and generegulation, with physiological and ecological implications that mayaffect human health and other organisms.</p>","PeriodicalId":47,"journal":{"name":"Journal of Natural Products ","volume":"89 8","pages":"2223–2237"},"PeriodicalIF":3.7,"publicationDate":"2026-08-28","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"146111498","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
Evaluation of the Alkaloid Secretions within the Millipede Brachycybe and Their Pheromone Properties 短足千足虫生物碱分泌及其信息素特性的评价。
IF 3.7 2区 生物学
Journal of Natural Products Pub Date : 2026-08-28 Epub Date: 2026-07-21 DOI: 10.1021/acs.jnatprod.6c00556
Arden Hatch, Anne C. Jones, Luisa F. Vasquez-Valverde, Paige Banks, Isabel Gooding, Lisa Markoff, Paul E. Marek, Emily Mevers
{"title":"Evaluation of the Alkaloid Secretions within the Millipede Brachycybe and Their Pheromone Properties","authors":"Arden Hatch,&nbsp;Anne C. Jones,&nbsp;Luisa F. Vasquez-Valverde,&nbsp;Paige Banks,&nbsp;Isabel Gooding,&nbsp;Lisa Markoff,&nbsp;Paul E. Marek,&nbsp;Emily Mevers","doi":"10.1021/acs.jnatprod.6c00556","DOIUrl":"10.1021/acs.jnatprod.6c00556","url":null,"abstract":"<p><em>Brachycybe</em> is a genus of the millipede subterclass Colobognatha, a group that exhibits rare social characteristics, including species aggregations and male brood care. Although it has been hypothesized that alkaloid-based defensive secretions may also function as pheromones, no studies have examined these traits. Here, we evaluated the chemical secretions of six species, two of which had not been previously studied, and conducted Y-tube pheromone assays. Chemical investigations elucidated the structures of three new metabolites: hydrogosodesmine acid (<strong>6</strong>), homo-hydrogosodesmine acid (<strong>7</strong>), and buzonamine acid (<strong>8</strong>). Y-tube pheromone assays revealed that <em>Brachycybe producta</em> is significantly attracted to conspecifics (<em>p</em> = 0.0428) and is deterred by a different species of alkaloid-producing millipede (<em>p</em> = 0.0161). The former assay was repeated using a mixture of the crude (<em>p</em> = 0.0428) and purified (<em>p</em> = 0.0433) chemical defense secretion from<em>B. producta</em>. This study provides the first evidence that colobognath millipede chemical secretions serve both defensive and pheromone roles.</p>","PeriodicalId":47,"journal":{"name":"Journal of Natural Products ","volume":"89 9","pages":"93–102"},"PeriodicalIF":3.7,"publicationDate":"2026-08-28","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"148547011","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
Utilize Metabolomics Molecular Networking to Guide the Discovery of Chemical Entities from Cordyceps militaris Against Blue Light Hazards 利用代谢组学分子网络指导发现蛹虫草抗蓝光危害的化学实体。
IF 3.7 2区 生物学
Journal of Natural Products Pub Date : 2026-08-28 Epub Date: 2026-07-09 DOI: 10.1021/acs.jnatprod.6c00427
Ho-Cheng Wu, Andrea Gu, Ya-Lin Chang, Chung-Kuang Lu, Yi-Chieh Lee, Po-Wei Yu, Tzong-Huei Lee
{"title":"Utilize Metabolomics Molecular Networking to Guide the Discovery of Chemical Entities from Cordyceps militaris Against Blue Light Hazards","authors":"Ho-Cheng Wu,&nbsp;Andrea Gu,&nbsp;Ya-Lin Chang,&nbsp;Chung-Kuang Lu,&nbsp;Yi-Chieh Lee,&nbsp;Po-Wei Yu,&nbsp;Tzong-Huei Lee","doi":"10.1021/acs.jnatprod.6c00427","DOIUrl":"10.1021/acs.jnatprod.6c00427","url":null,"abstract":"<p>Increasing exposure to blue light has raised concernabout retinalinjury, particularly in retinal pigment epithelial (RPE) cells. <em>N</em>-retinylidene-<em>N</em>-retinylethanolamine (A2E),a photosensitive fluorophore associated with age-related macular degeneration,is an important mediator of this process. In this study, feature-basedmolecular networking guided the identification of cordylutenes A–J(<strong>1</strong>–<strong>10</strong>), a new molecular family ofblue light–protective fungal pigments from <em>Cordyceps militaris</em>. These metabolites possess a previouslyunreported symmetric all-<em>E</em> C20 polyene dicarbonylskeleton with carotenoid-like UV absorption. They were characterizedat the molecular-family level by shared UV features and diagnostic,internally consistent MS<sup>2</sup> fragmentation patterns. CordylutenesA (<strong>1</strong>) and B (<strong>2</strong>) were isolated as representativemembers for structural characterization. In an A2E-mediated blue-lightinjury model in ARPE-19 cells, the cordylutene complex (CCL, 1 μg/mL)and cordylutene A (<strong>1</strong>, 0.1 μg/mL) improved cellviability to 84.78 ± 4.02% and 92.14 ± 1.88%, respectively,and reduced intracellular oxidative stress to 63.67 ± 3.33% and43.89 ± 9.59%, respectively. These findings identify cordylutenesas a new family of fungal pigments with protective effects in an A2E-mediatedphoto-oxidative retinal cell injury model.</p>","PeriodicalId":47,"journal":{"name":"Journal of Natural Products ","volume":"89 8","pages":"2265–2274"},"PeriodicalIF":3.7,"publicationDate":"2026-08-28","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"148417083","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
Diacarnusins A-F, nor-Terpene Endoperoxides of the Red Sea Sponge Diacarnus erythraeanus 红海海绵diacarus Red thrraeanus的非萜内过氧化物diacarusins A-F。
IF 3.7 2区 生物学
Journal of Natural Products Pub Date : 2026-08-28 Epub Date: 2026-07-17 DOI: 10.1021/acs.jnatprod.6c00510
Rania Hasib Afana, Lilach Raijman-Nagar, Micha Ilan, Shmuel Carmeli
{"title":"Diacarnusins A-F, nor-Terpene Endoperoxides of the Red Sea Sponge Diacarnus erythraeanus","authors":"Rania Hasib Afana,&nbsp;Lilach Raijman-Nagar,&nbsp;Micha Ilan,&nbsp;Shmuel Carmeli","doi":"10.1021/acs.jnatprod.6c00510","DOIUrl":"10.1021/acs.jnatprod.6c00510","url":null,"abstract":"<p>Six new <em>nor-</em>terpene endoperoxides, diacarnusinsA–F (<strong>1</strong>–<strong>6</strong>), along with fiveknown ones (<strong>7</strong>–<strong>11</strong>), were isolatedfrom the extract of the Red Sea sponge <em>Diacarnus erythraeanus</em>, which presented cytotoxic activity against the colon carcinomacell line. The structure elucidation was performed by analysis ofmass spectrometric and 1D and 2D NMR data. The relative and absoluteconfigurations of the stereocenters of the compounds were deducedbased on the Capon and Macleod empirical rule and comparison of thesign of their specific rotations with those of endoperoxides withproven absolute configurations. The cytotoxicity of the pure compoundswas evaluated against a panel of cancer cell lines. The structureelucidation and biological activity of the compounds are discussed.</p>","PeriodicalId":47,"journal":{"name":"Journal of Natural Products ","volume":"89 8","pages":"2314–2321"},"PeriodicalIF":3.7,"publicationDate":"2026-08-28","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"148467845","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 Cyclotides via LC-MS/MS from the Vietnamese Plant Viola annamensis Bak.f.: Insights into Antimicrobial and Larvicidal Activities 通过LC-MS/MS表征越南植物紫叶堇菜(Viola annamensis bakf .f.)的环核苷酸:抗菌和杀幼虫活性的研究
IF 3.7 2区 生物学
Journal of Natural Products Pub Date : 2026-08-28 Epub Date: 2026-07-08 DOI: 10.1021/acs.jnatprod.6c00512
Tien T. Dang, Tam T. T. Tran, Uyen N. P. Nguyen, Son H. Pham, Tuan H. N. Nguyen
{"title":"Characterization of Cyclotides via LC-MS/MS from the Vietnamese Plant Viola annamensis Bak.f.: Insights into Antimicrobial and Larvicidal Activities","authors":"Tien T. Dang,&nbsp;Tam T. T. Tran,&nbsp;Uyen N. P. Nguyen,&nbsp;Son H. Pham,&nbsp;Tuan H. N. Nguyen","doi":"10.1021/acs.jnatprod.6c00512","DOIUrl":"10.1021/acs.jnatprod.6c00512","url":null,"abstract":"<p><em>Viola annamensis</em> Bak.f.,a Vietnameseendemic species, is reported here for the first time as a source ofcyclotides. LC–MS and LC - MS/MS analyses identified 11 cyclotides(3.1–3.8 kDa) bearing the conserved cyclic cystine knot (CCK)motif, including four novel cyclotides designated Vian A, Vian B,Vian C, and Vian D. Fraction M1 contained eight cyclotides, includingVian A, whereas fractions M2 and M3 mainly contained Vian B/Vian Cand Vian D, respectively. Vian D was successfully purified, sequenced,and evaluated for antimicrobial activity. The peptide mixtures M2and Vian D showed antibacterial activity against <em>Pseudomonas aeruginosa</em>, <em>Bacillus subtilis</em>, and <em>Listeria ivanovii</em>. Minimum inhibitoryconcentration (MIC) values for M2 and Vian D ranged from 6.2 to 8.3mg/mL, confirming the contribution of these cyclotides to the antimicrobialproperties of <em>V.</em><em>annamensis</em>. Cytotoxicity assessment using the <em>Artemia salina</em> assay showed low toxicity for the salt-precipitated sample, withan LC<sub>50</sub> value of 1.042 mg/mL, whereas the purified peptidemixtures exhibited higher, concentration-dependent toxicity. Amongthem, M1 demonstrated greater potency, with an LC<sub>50</sub> of0.049 mg/mL, followed by M2 with an LC<sub>50</sub> of 0.131 mg/mL.This study identifies <em>V. annamensis</em> as a novel source of new cyclotides with potential antimicrobialapplications.</p>","PeriodicalId":47,"journal":{"name":"Journal of Natural Products ","volume":"89 8","pages":"2300–2313"},"PeriodicalIF":3.7,"publicationDate":"2026-08-28","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"148402956","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
Nigroepocins A-D: Antifungal Polyketides from Nigrospora sp. SN56127 with Activity against Fusarium graminearum 黑孢菌素A-D:黑孢菌SN56127抗真菌多酮类化合物。
IF 3.7 2区 生物学
Journal of Natural Products Pub Date : 2026-08-28 Epub Date: 2026-07-14 DOI: 10.1021/acs.jnatprod.6c00455
Shijun Zhong, Jiajun Chen, Huiyuan Yu, Yifan Miao, Yinan Wang, Zhiguo Yu
{"title":"Nigroepocins A-D: Antifungal Polyketides from Nigrospora sp. SN56127 with Activity against Fusarium graminearum","authors":"Shijun Zhong,&nbsp;Jiajun Chen,&nbsp;Huiyuan Yu,&nbsp;Yifan Miao,&nbsp;Yinan Wang,&nbsp;Zhiguo Yu","doi":"10.1021/acs.jnatprod.6c00455","DOIUrl":"10.1021/acs.jnatprod.6c00455","url":null,"abstract":"<p>Nigroepocins A-D (<strong>1</strong>–<strong>4</strong>), alongwith one known compound clavatol (<strong>5</strong>), were isolated fromthe fermentation broth of <em>Nigrospora</em> sp. SN56127.Their structures, including absolute configurations, were determinedby NMR, MS, and single-crystal X-ray diffraction analyses. Each ofthe four compounds (<strong>1</strong>–<strong>4</strong>) possessesa three-membered epoxy ring, which is rare in other compounds isolatedfrom <em>Nigrospora</em>. All compounds (<strong>1</strong>–<strong>5</strong>) were evaluated for their antifungal activities against <em>Fusarium graminearum</em>, and nigroepocin A (<strong>1</strong>) exhibited inhibition with EC<sub>50</sub> values of 110 and 23.1μM against mycelial growth and conidial germination, respectively.</p>","PeriodicalId":47,"journal":{"name":"Journal of Natural Products ","volume":"89 8","pages":"2413–2420"},"PeriodicalIF":3.7,"publicationDate":"2026-08-28","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"148443509","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
Sulphopreussomerins: Sulfur-Containing Preussomerins Isolated from the Marine-Derived Fungus Pyrenochaetopsis indica 含硫前菌素:从海源真菌印度热毛藻中分离出的含硫前菌素。
IF 3.7 2区 生物学
Journal of Natural Products Pub Date : 2026-08-28 Epub Date: 2026-05-15 DOI: 10.1021/acs.jnatprod.6c00324
Georgia Karyofyllidou, Rachel Serrano, Víctor González-Menéndez, Jesús Martín, Thomas A. Mackenzie, Maria C. Ramos, Juan Ortega-Vidal, Olivier P. Thomas, José R. Tormo, Olga Genilloud, Fernando Reyes
{"title":"Sulphopreussomerins: Sulfur-Containing Preussomerins Isolated from the Marine-Derived Fungus Pyrenochaetopsis indica","authors":"Georgia Karyofyllidou,&nbsp;Rachel Serrano,&nbsp;Víctor González-Menéndez,&nbsp;Jesús Martín,&nbsp;Thomas A. Mackenzie,&nbsp;Maria C. Ramos,&nbsp;Juan Ortega-Vidal,&nbsp;Olivier P. Thomas,&nbsp;José R. Tormo,&nbsp;Olga Genilloud,&nbsp;Fernando Reyes","doi":"10.1021/acs.jnatprod.6c00324","DOIUrl":"10.1021/acs.jnatprod.6c00324","url":null,"abstract":"<p>The organic extract of <em>Pyrenochaetopsis indica</em> CF-301929, a fungal strain collected from theCoral Sea in Australia,showed broad-spectrum activity against the fungal phytopathogens <em>Zymoseptoria tritici</em>, <em>Colletotrichum acutatum</em>, <em>Fusarium proliferatum</em>, and <em>Magnaporthe grisea</em>. After extensivepurification, five compounds were isolated, including three new sulfurcontaining preussomerins <strong>1</strong>–<strong>3</strong> alongwith two previously described molecules, ascochytatin (<strong>4</strong>) and preussomerin G (<strong>5</strong>). The new compounds incorporaterare thioglycolic or 2-hydroxy-3-mercaptopropionic acid moieties intheir structures, and they represent the first members of a new classof preussomerins that we have named sulphopreussomerins. Multiplespectroscopic analyses, including HRESIMS and 1D/2D NMR experimentswere used to elucidate their structures while the proposed absoluteconfiguration of compound <strong>1</strong> was assigned by comparisonof the experimental and theoretical ECD spectra. When tested againsta fungal phytopathogen panel, preussomerin G exhibited, as previouslyreported, strong antifungal activity and cytotoxicity, whereas sulphopreussomerinA and ascochytatin showed moderate antifungal activity against <em>Z. tritici</em> with no detectable cytotoxicity.</p>","PeriodicalId":47,"journal":{"name":"Journal of Natural Products ","volume":"89 8","pages":"2253–2264"},"PeriodicalIF":3.7,"publicationDate":"2026-08-28","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"147947246","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 Insights into Metal-Chelating Natural Inhibitors of Factor Inhibiting HIF-1α 金属螯合因子抑制HIF-1α天然抑制剂的结构见解。
IF 3.7 2区 生物学
Journal of Natural Products Pub Date : 2026-08-28 Epub Date: 2026-07-15 DOI: 10.1021/acs.jnatprod.6c00734
Yochidamai Akhsanitaqwim, Yu Nakashima, Naotaka Ikumi, Hiroyuki Morita
{"title":"Structural Insights into Metal-Chelating Natural Inhibitors of Factor Inhibiting HIF-1α","authors":"Yochidamai Akhsanitaqwim,&nbsp;Yu Nakashima,&nbsp;Naotaka Ikumi,&nbsp;Hiroyuki Morita","doi":"10.1021/acs.jnatprod.6c00734","DOIUrl":"10.1021/acs.jnatprod.6c00734","url":null,"abstract":"<p>Factorinhibiting HIF-1α (FIH) is a 2-oxoglutarate-dependentoxygenase that controls hypoxia signaling and metabolic homeostasisby hydroxylating HIF-1α. Although selective pharmacologicalinhibition of FIH represents an emerging therapeutic strategy formetabolic disorders, structurally diverse natural inhibitors remainlargely unexplored. Here, we identified five natural FIH inhibitorsspanning distinct phytochemical classes, including three flavonoids(wogonin, luteolin, morin), a coumarin (isofraxidin), and an anthraquinone(rhein). Co-crystal structures revealed that structurally diversenatural products converge on a common bidentate metal-chelation geometrywithin the FIH active site despite substantial differences in scaffoldarchitecture. Among these inhibitors, wogonin most closely mimickedthe orientation of the HIF-1α Asn803 side chain within the substrate-bindingcleft, resulting in inhibitory potency comparable to that of the 2-oxoglutarateanalog <em>N</em>-oxalylglycine. These findings establishthe first structural framework for natural-product-based FIH inhibitionand demonstrate that structurally distinct natural inhibitors adopta conserved metal-chelation geometry within the FIH active site. Thisframework provides a basis for the future development of metabolicallyoriented FIH inhibitors.</p>","PeriodicalId":47,"journal":{"name":"Journal of Natural Products ","volume":"89 8","pages":"2405–2412"},"PeriodicalIF":3.7,"publicationDate":"2026-08-28","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"148443517","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
Xeniaphyllane-Type Diterpenoids from the Soft Coral Sclerophytum humesi: Resolving Absolute Configurations and Anti-Alzheimer’s Potential 软珊瑚硬珊瑚中的xeniaphylene型二萜:解析绝对构型和抗阿尔茨海默病的潜力。
IF 3.7 2区 生物学
Journal of Natural Products Pub Date : 2026-07-24 Epub Date: 2026-07-09 DOI: 10.1021/acs.jnatprod.6c00535
Phuong Vu Luu, Cuong-Quoc Nguyen, Huong Lien Ton-Nu, Thuy-Tien Thi Phan, Quoc-Dung Tran Huynh, Ngoc-Thac Pham, Huong-Giang Le, Lo-Yun Chen, Yu-Chia Chang, Jui-Hsin Su, Bo-Rong Peng, Kuei-Hung Lai
{"title":"Xeniaphyllane-Type Diterpenoids from the Soft Coral Sclerophytum humesi: Resolving Absolute Configurations and Anti-Alzheimer’s Potential","authors":"Phuong Vu Luu,&nbsp;Cuong-Quoc Nguyen,&nbsp;Huong Lien Ton-Nu,&nbsp;Thuy-Tien Thi Phan,&nbsp;Quoc-Dung Tran Huynh,&nbsp;Ngoc-Thac Pham,&nbsp;Huong-Giang Le,&nbsp;Lo-Yun Chen,&nbsp;Yu-Chia Chang,&nbsp;Jui-Hsin Su,&nbsp;Bo-Rong Peng,&nbsp;Kuei-Hung Lai","doi":"10.1021/acs.jnatprod.6c00535","DOIUrl":"10.1021/acs.jnatprod.6c00535","url":null,"abstract":"<p>A combined bioassay- and <sup>1</sup>H NMR-guided isolation strategyled to the discovery of four new terpenoids, including three xeniaphyllane-typediterpenoids, sclerohumins P–R (<strong>1–3</strong>), anda norcaryophyllene-type, sclerophyllene A (<strong>4</strong>), from thesoft coral <em>Sclerophytum humesi</em>. Thestructures and absolute configurations of these compounds were elucidatedby comprehensive spectroscopic analysis, including NMR, HRESIMS, SOR,TDDFT-ECD, and DP4+ probability analysis. The stereogenic centersat C-15 in related xeniaphyllanes were proposed for the first timebased on comparative SOR analysis. Compounds <strong>1</strong> and <strong>2</strong> possess a tricyclic 4/9-fused carbocyclic framework featuringan epoxide moiety, whereas compounds <strong>3</strong> and <strong>4</strong> exhibit related bicyclic scaffolds. A plausible biogenetic pathwayoriginating from geranylgeranyl pyrophosphate (GGPP) was proposedto account for their structural diversity. Compounds <strong>1</strong> and <strong>2</strong> showed potent AChE inhibitory activity (IC<sub>50</sub> = 1.7 and 4.4 μM, respectively), while being inactiveagainst BChE and noncytotoxic toward normal cell lines (HEK293 andVero). Mechanistic studies combining enzyme kinetics and moleculardocking revealed that <strong>1</strong> and <strong>2</strong> act as mixed-typeAChE inhibitors, with <em>K</em><sub>i</sub> values of 1.02and 1.87 μM, respectively. These findings represent the firstreport of xeniaphyllane-type diterpenoids with potential for neurotherapeuticdevelopment.</p>","PeriodicalId":47,"journal":{"name":"Journal of Natural Products ","volume":"89 7","pages":"2143–2156"},"PeriodicalIF":3.7,"publicationDate":"2026-07-24","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"148409723","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
Biosynthesis of Benzohydroxamic Acid in Streptomyces angustmyceticus 链霉菌苯甲羟肟酸的生物合成。
IF 3.7 2区 生物学
Journal of Natural Products Pub Date : 2026-07-24 Epub Date: 2026-06-23 DOI: 10.1021/acs.jnatprod.6c00526
Jiangpeng Yu, Peibo Liang, Jie Wang, Qing Yang, Wei Li
{"title":"Biosynthesis of Benzohydroxamic Acid in Streptomyces angustmyceticus","authors":"Jiangpeng Yu,&nbsp;Peibo Liang,&nbsp;Jie Wang,&nbsp;Qing Yang,&nbsp;Wei Li","doi":"10.1021/acs.jnatprod.6c00526","DOIUrl":"10.1021/acs.jnatprod.6c00526","url":null,"abstract":"<p>Benzohydroxamic acid (BHA) is animportant hydroxamatescaffoldwith potential applications in medicinal chemistry and crop protection,but it has not previously been established as a natural product. Here,we report the discovery and biosynthetic characterization of BHA from <em>Streptomyces angustmyceticus</em>. A conserved TsnB-likegene cassette comprising <em>SaAmOx-AS</em>, <em>SaAmOx</em>, and <em>SaHAT</em> was identified by genome mining, indicatinga potential capacity for hydroxamate formation and transfer. BHA wasdetected as a fermentation product of <em>S. angustmyceticus</em> and structurally confirmed by comparison with an authentic standard,compound purification, and NMR spectroscopic analysis. Benzoic acidwas established as the aromatic precursor of BHA through deuterium-labelingexperiments with benzaldehyde and cinnamic acid. SaHAT was identifiedas the key hydroxamate-transfer enzyme that directly converts benzoicacid, rather than benzoyl-CoA, to BHA using glutamyl hydroxamate asthe hydroxamate donor in an ATP- and Mg<sup>2+</sup>-dependent reaction.BHA production was reconstituted in <em>Escherichia coli</em> by heterologous coexpression of SaAmOx-AS, SaAmOx, and SaHAT, confirmingthat these three enzymes form a minimal biosynthetic module. Thiswork establishes BHA as a microbial natural product and provides afoundation for engineering hydroxamate-containing compounds.</p>","PeriodicalId":47,"journal":{"name":"Journal of Natural Products ","volume":"89 7","pages":"2133–2142"},"PeriodicalIF":3.7,"publicationDate":"2026-07-24","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"148306283","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
0
×
引用
GB/T 7714-2015
复制
MLA
复制
APA
复制
导出至
BibTeX EndNote RefMan NoteFirst NoteExpress
×
提示
您的信息不完整,为了账户安全,请先补充。
现在去补充
×
提示
您因"违规操作"
具体请查看互助需知
我知道了
×
提示
确定
请完成安全验证×
相关产品
×
本文献相关产品
联系我们:info@booksci.cn Book学术提供免费学术资源搜索服务,方便国内外学者检索中英文文献。致力于提供最便捷和优质的服务体验。 Copyright © 2023 布克学术 All rights reserved.
京ICP备2023020795号-1
ghs 京公网安备 11010802042870号
Book学术文献互助
Book学术文献互助群
群 号:604180095
Book学术官方微信
小红书