Journal of Natural Products 最新文献_第8页

Revisiting the Cyclocephagenols via Astragalus condensatus: Structural Insights and Configurational Revision. 通过黄芪重新审视环黄芪醇：结构见解和构型修正。

IF 3.3 2区生物学

Journal of Natural Products Pub Date : 2024-11-22 Epub Date: 2024-10-26 DOI: 10.1021/acs.jnatprod.4c00751

Fadime Aydoğan, Pankaj Pandey, Frank R Fronczek, Daneel Ferreira, Ikhlas A Khan, Zulfiqar Ali, Amar G Chittiboyina

{"title":"Revisiting the Cyclocephagenols via Astragalus condensatus: Structural Insights and Configurational Revision.","authors":"Fadime Aydoğan, Pankaj Pandey, Frank R Fronczek, Daneel Ferreira, Ikhlas A Khan, Zulfiqar Ali, Amar G Chittiboyina","doi":"10.1021/acs.jnatprod.4c00751","DOIUrl":"10.1021/acs.jnatprod.4c00751","url":null,"abstract":"The phytochemical investigation of the MeOH extract of Astragalus condensatus roots led to the discovery of a new tetrahydropyran cycloartane-type triterpenoid, astracondensatol A (1), alongside six known cyclocephagenol derivatives (2, 3, 20, 32, 35, and 36). Elucidation of their structures involved 1D and 2D-NMR spectroscopy and mass data analysis. Upon comparing NMR spectroscopic data with prior literature, several carbon shift anomalies, particularly at C-24, prompted a reevaluation using quantum chemical calculations, resulting in the revision of the 24S to 24R absolute configuration for compound 2 and 38 other reported cyclocephagenol-type triterpenoids. X-ray crystallography data further supported the analysis in establishing the absolute configuration of compound 2. Ambiguous NOE correlations and publication bias could have played a significant role in miss-assigning the C-24 absolute configuration in tetrahydropyran cycloartane-type triterpenoids.","PeriodicalId":47,"journal":{"name":"Journal of Natural Products ","volume":" ","pages":"2657-2664"},"PeriodicalIF":3.3,"publicationDate":"2024-11-22","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"142491142","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

Structurally Diverse Duclauxins from a Coral-Derived Talaromyces sp. and Insight into Determining the Configuration at C-1 of Heptacyclic Duclauxins by ¹H NMR. 来自珊瑚衍生的塔拉酵母菌的结构多样的杜鹃花素，以及通过 1H NMR 确定七环杜鹃花素 C-1 构型的启示。

IF 3.3 2区生物学

Journal of Natural Products Pub Date : 2024-11-22 Epub Date: 2024-11-04 DOI: 10.1021/acs.jnatprod.4c00709

Hanxiao Zeng, Yaxing Wang, Chenyang Wang, Yahui Huang, Shuang Lin, Jiangchun Wei, Weiguang Sun, Fei Cao, Yonghui Zhang, Zhengxi Hu

{"title":"Structurally Diverse Duclauxins from a Coral-Derived Talaromyces sp. and Insight into Determining the Configuration at C-1 of Heptacyclic Duclauxins by 1H NMR.","authors":"Hanxiao Zeng, Yaxing Wang, Chenyang Wang, Yahui Huang, Shuang Lin, Jiangchun Wei, Weiguang Sun, Fei Cao, Yonghui Zhang, Zhengxi Hu","doi":"10.1021/acs.jnatprod.4c00709","DOIUrl":"10.1021/acs.jnatprod.4c00709","url":null,"abstract":"A chemical investigation of the coral-derived fungus Talaromyces sp. TJ403-AL05 led to the isolation of 18 duclauxin analogues (1-18), 14 of which, taladuxins A-N (1-14), are new and consist of the first example of duclauxin fused with one 1,6-dioxaspiro[4.5]decan-2-one moiety (1), as well as its biosynthetic product (2), and 12 6/6/6/5/6/6/6 heptacyclic derivatives (3-14). Comprehensive spectroscopic analyses, electronic circular dichroism (ECD) calculations, DP4+ probability analyses, single-crystal X-ray diffraction, and vibrational circular dichroism (VCD) calculations were employed to characterize their structures and revise the published structure of verruculosin B. An efficient 1H NMR method was established to discriminate 1R and 1S configurations at C-1 of 6/6/6/5/6/6/6 heptacyclic duclauxins according to chemical shift differences of diastereotopic methylene H2-11 or H2-12 (ΔδH-11 or ΔδH-12). Compounds 4, 7-8, 13-15, and 18 exhibited moderate inhibition of Arabidopsis thaliana 4-hydroxyphenylpyruvate dioxygenase (AtHPPD), with IC50 values ranging from 17.1 to 71.3 μM.","PeriodicalId":47,"journal":{"name":"Journal of Natural Products ","volume":" ","pages":"2592-2603"},"PeriodicalIF":3.3,"publicationDate":"2024-11-22","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"142574985","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

MACE, an Open Access Database of Electron Impact Mass Spectra of Natural Products MACE，天然产品电子碰撞质谱开放存取数据库

IF 3.3 2区生物学

Journal of Natural Products Pub Date : 2024-11-22 DOI: 10.1021/acs.jnatprod.4c0124010.1021/acs.jnatprod.4c01240

Stefan Schulz, and , Anton Möllerke,

引用次数: 0

Pullenvalenes E-H: Triterpenyl-Aminoglycosides from an Australian Soil-Derived Fungus, Clonostachys sp. Pullenvalenes E-H: Triterpenyl-Aminoglycosides from an Australian Soil-Derived Fungus, Clonostachys sp.

IF 3.3 2区生物学

Journal of Natural Products Pub Date : 2024-11-22 Epub Date: 2024-11-12 DOI: 10.1021/acs.jnatprod.4c01068

Yanan Wang, Jolynn Kiong, Amila Agampodi Dewa, Angela A Salim, Zeinab G Khalil, Robert J Capon

{"title":"Pullenvalenes E-H: Triterpenyl-Aminoglycosides from an Australian Soil-Derived Fungus, Clonostachys sp.","authors":"Yanan Wang, Jolynn Kiong, Amila Agampodi Dewa, Angela A Salim, Zeinab G Khalil, Robert J Capon","doi":"10.1021/acs.jnatprod.4c01068","DOIUrl":"10.1021/acs.jnatprod.4c01068","url":null,"abstract":"Chemical profiling of soil-derived microbes collected under the auspices of the Australian citizen science initiative Soils for Science detected two fungi, Clonostachys sp. S4S-07771A07 and Coccidiodes sp. S4S-14879B01, capable of producing pullenvalenes, a rare class of triterpene glycoside. Cultivation profiling followed by scaled up cultivation and fractionation of the former yielded the known pullenvalenes A-D (1-4) and the new analogues E-H (5-8), with structures secured by detailed spectroscopic analysis and biogenetic considerations. This study reveals that the pullenvalenes 1-8 are produced by several genera of fungi (Clonostachys, Coccidiodes and Talaromyces) recovered from different geographic locations and substrates. We also draw attention to structural and biosynthetic similarities with the known Red Sea sponge metabolites neviotines A-D (9-12) and abudinols A-B (13-14), prompting speculation that the latter may be products of sponge-associated fungi.","PeriodicalId":47,"journal":{"name":"Journal of Natural Products ","volume":" ","pages":"2649-2656"},"PeriodicalIF":3.3,"publicationDate":"2024-11-22","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"142612710","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

Doubly Homologated Tyrosine-Containing Peptides from the Cyanobacterium Microcystis aeruginosa NIES-4285 and Their Biosynthesis. 来自铜绿微囊藻 NIES-4285 蓝藻的双同源含酪氨酸肽及其生物合成。

IF 3.3 2区生物学

Journal of Natural Products Pub Date : 2024-11-22 Epub Date: 2024-10-30 DOI: 10.1021/acs.jnatprod.4c00972

Chin-Soon Phan, Zhengyi Ling, Jakia Jerin Mehjabin, Kenichi Matsuda, Nurcahyo Iman Prakoso, Taiki Umezawa, Toshiyuki Wakimoto, Tatsufumi Okino

{"title":"Doubly Homologated Tyrosine-Containing Peptides from the Cyanobacterium Microcystis aeruginosa NIES-4285 and Their Biosynthesis.","authors":"Chin-Soon Phan, Zhengyi Ling, Jakia Jerin Mehjabin, Kenichi Matsuda, Nurcahyo Iman Prakoso, Taiki Umezawa, Toshiyuki Wakimoto, Tatsufumi Okino","doi":"10.1021/acs.jnatprod.4c00972","DOIUrl":"10.1021/acs.jnatprod.4c00972","url":null,"abstract":"Chemical investigation of the cyanobacterium Microcystis aeruginosa NIES-4285 led to the isolation of six new natural products, microginins 705 (1), 719 (2), 733A (3), 733B (4), and 733C (5), and anabaenopeptin 885 (7), and three known compounds, anabaenopeptins 871 (6), B (8), and F (9). Planar structures and absolute configurations for 1-7 were determined by 2D NMR, HRMS, and Marfey's analyses. Microginin 733C (5), and anabaenopeptins 871 (6) and 885 (7) contained a unique residue of 2-amino-5-(4-hydroxyphenyl)pentanoic acid (Ahppa): doubly homologated tyrosine (di-hTyr). The biosynthetic origin of this nonproteinogenic amino acid di-hTyr was investigated, and it was found that MaHphABCDE are involved in the production of di-hTyr. In addition, biochemical characterization of aminotransferase MaHphE showed that it is a promiscuous enzyme. This result expanded the biocatalytic toolbox for amino acid homologation.","PeriodicalId":47,"journal":{"name":"Journal of Natural Products ","volume":" ","pages":"2629-2639"},"PeriodicalIF":3.3,"publicationDate":"2024-11-22","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"142542874","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

Expression of Concern for "Tepuazines A-E: Phenazine Glycosides from a Venezuelan Quartz-Rich (Tepui) Cave Soil-Derived Streptomyces virginiae CMB-CA091". 表达对 "Tepuazines A-E: Phenazine Glycosides from a Venezuelan Quartz-Rich (Tepui) Cave Soil-Derived Streptomyces virginiae CMB-CA091 "的关注。

IF 3.3 2区生物学

Journal of Natural Products Pub Date : 2024-11-22 Epub Date: 2024-11-13 DOI: 10.1021/acs.jnatprod.4c01237

Philip J Proteau

引用次数: 0

New Discorhabdin D Analogues from Latrunculia spp. Sponges. 从 Latrunculia spp.海绵中提取的新 Discorhabdin D 类似物。

IF 3.3 2区生物学

Journal of Natural Products Pub Date : 2024-11-22 Epub Date: 2024-10-25 DOI: 10.1021/acs.jnatprod.4c01036

Maria Orfanoudaki, Masoumeh Dalilian, Lin Du, Cindy H Chau, William D Figg, Barry R O'Keefe, Tanja Grkovic

引用次数: 0

Expression of Concern for “Tepuazines A–E: Phenazine Glycosides from a Venezuelan Quartz-Rich (Tepui) Cave Soil-Derived Streptomyces virginiae CMB-CA091” 对 "Tepuazines A-E: Phenazine Glycosides from a Venezuelan Quartz-Rich (Tepui) Cave Soil-Derived Streptomycese virginiae CMB-CA091" 表示关注

IF 3.3 2区生物学

Journal of Natural Products Pub Date : 2024-11-13 DOI: 10.1021/acs.jnatprod.4c0123710.1021/acs.jnatprod.4c01237

Philip J. Proteau*,

引用次数: 0

Pullenvalenes E–H: Triterpenyl-Aminoglycosides from an Australian Soil-Derived Fungus, Clonostachys sp. Pullenvalenes E-H: Triterpenyl-Aminoglycosides from an Australian Soil-Derived Fungus, Clonostachys sp.

IF 3.3 2区生物学

Journal of Natural Products Pub Date : 2024-11-12 DOI: 10.1021/acs.jnatprod.4c0106810.1021/acs.jnatprod.4c01068

Yanan Wang, Jolynn Kiong, Amila Agampodi Dewa, Angela A. Salim, Zeinab G. Khalil and Robert J. Capon*,

{"title":"Pullenvalenes E–H: Triterpenyl-Aminoglycosides from an Australian Soil-Derived Fungus, Clonostachys sp.","authors":"Yanan Wang, Jolynn Kiong, Amila Agampodi Dewa, Angela A. Salim, Zeinab G. Khalil and Robert J. Capon*, ","doi":"10.1021/acs.jnatprod.4c0106810.1021/acs.jnatprod.4c01068","DOIUrl":"https://doi.org/10.1021/acs.jnatprod.4c01068https://doi.org/10.1021/acs.jnatprod.4c01068","url":null,"abstract":"Chemical profiling of soil-derived microbes collected under the auspices of the Australian citizen science initiative Soils for Science detected two fungi, Clonostachys sp. S4S-07771A07 and Coccidiodes sp. S4S-14879B01, capable of producing pullenvalenes, a rare class of triterpene glycoside. Cultivation profiling followed by scaled up cultivation and fractionation of the former yielded the known pullenvalenes A–D (1–4) and the new analogues E–H (5–8), with structures secured by detailed spectroscopic analysis and biogenetic considerations. This study reveals that the pullenvalenes 1–8 are produced by several genera of fungi (Clonostachys, Coccidiodes and Talaromyces) recovered from different geographic locations and substrates. We also draw attention to structural and biosynthetic similarities with the known Red Sea sponge metabolites neviotines A–D (9–12) and abudinols A–B (13–14), prompting speculation that the latter may be products of sponge-associated fungi.","PeriodicalId":47,"journal":{"name":"Journal of Natural Products ","volume":"87 11","pages":"2649–2656 2649–2656"},"PeriodicalIF":3.3,"publicationDate":"2024-11-12","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"142685206","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

Exploring Biological Targets of Magnolol and Honokiol and their Nature-Inspired Synthetic Derivatives: In Silico Identification and Experimental Validation of Estrogen Receptors 探索 Magnolol 和 Honokiol 及其受大自然启发的合成衍生物的生物靶标：雌激素受体的硅学鉴定和实验验证

IF 3.3 2区生物学

Journal of Natural Products Pub Date : 2024-11-11 DOI: 10.1021/acs.jnatprod.4c0063410.1021/acs.jnatprod.4c00634

Annachiara Tinivella, Jerome C. Nwachukwu, Luca Pinzi, Maria Antonietta Dettori, Davide Fabbri, Paola Carta, Kendall W. Nettles and Giulio Rastelli*,

{"title":"Exploring Biological Targets of Magnolol and Honokiol and their Nature-Inspired Synthetic Derivatives: In Silico Identification and Experimental Validation of Estrogen Receptors","authors":"Annachiara Tinivella, Jerome C. Nwachukwu, Luca Pinzi, Maria Antonietta Dettori, Davide Fabbri, Paola Carta, Kendall W. Nettles and Giulio Rastelli*, ","doi":"10.1021/acs.jnatprod.4c0063410.1021/acs.jnatprod.4c00634","DOIUrl":"https://doi.org/10.1021/acs.jnatprod.4c00634https://doi.org/10.1021/acs.jnatprod.4c00634","url":null,"abstract":"In this work, we describe the results of a computational investigation aimed at identifying potential biological targets of honokiol, magnolol and a series of synthetic prodrug derivatives obtained through esterification of the free hydroxyl groups. The ligand-based and structure-based analyses revealed that these compounds potentially interact with several biological targets, some of which are known while others are new. Honokiol, magnolol, and three of the newly synthesized derivatives may bind to estrogen receptors ERα and ERβ. Biological testing confirmed that these compounds modulate estrogen-regulated transcriptional activity mediated by ERα or ERβ with potencies in the nanomolar range. In particular, magnolol and one of its derivatives (10) behaved as partial antagonists of ERα and ERβ, while compounds 8 and 11 behaved as partial agonists. These findings validate the computational predictions and shed light on the mechanism of action of these natural compounds, paving the way for further investigation in the context of targeted therapies.","PeriodicalId":47,"journal":{"name":"Journal of Natural Products ","volume":"87 11","pages":"2568–2579 2568–2579"},"PeriodicalIF":3.3,"publicationDate":"2024-11-11","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"142691391","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