Journal of Natural Products 最新文献

Iodide Enhances the Production of Pseurotin D over Pseurotin A by Inverting the Preference for the S_N2 versus the S_N2' Product in the Final Nonenzymatic Step.

IF 3.3 2区生物学

Journal of Natural Products Pub Date : 2024-12-23 DOI: 10.1021/acs.jnatprod.4c01128

Yukyung Choi, Yeongseo Kim, Jin Wook Cha, Gyu Sung Lee, Huong T Pham, Men Thi Ngo, Saegun Kim, Chung Sub Kim, Kyo Bin Kang

引用次数: 0

The Paradox of Antimalarial Terpenoid Isonitrile Biosynthesis Explained. Proposal of Cyanoformate as an NC Delivery Vector.

IF 3.3 2区生物学

Journal of Natural Products Pub Date : 2024-12-20 DOI: 10.1021/acs.jnatprod.4c01295

Tadeusz F Molinski

引用次数: 0

Metabologenomics-Driven Discovery of Nocardimicins from a Psychrophilic Nocardia sp. Strain.

IF 3.3 2区生物学

Journal of Natural Products Pub Date : 2024-12-20 DOI: 10.1021/acs.jnatprod.4c01140

Suling Xu, Nengfei Wang, Qingzhou Meng, Wenjie Ma, Huayue Li

引用次数: 0

Pyridoxal 5'-Phosphate (PLP)-Dependent β- and γ-Substitution Reactions Forming Nonproteinogenic Amino Acids in Natural Product Biosynthesis.

IF 3.3 2区生物学

Journal of Natural Products Pub Date : 2024-12-19 DOI: 10.1021/acs.jnatprod.4c01226

Taku Mizutani, Ikuro Abe

引用次数: 0

Cardenolides in Asclepias syriaca Seeds: Exploring the Legacy of Tadeus Reichstein.

IF 3.3 2区生物学

Journal of Natural Products Pub Date : 2024-12-18 DOI: 10.1021/acs.jnatprod.4c00960

Paola Rubiano-Buitrago, Ronald A White, Amy P Hastings, Frank C Schroeder, Anurag A Agrawal, Christophe Duplais

{"title":"Cardenolides in Asclepias syriaca Seeds: Exploring the Legacy of Tadeus Reichstein.","authors":"Paola Rubiano-Buitrago, Ronald A White, Amy P Hastings, Frank C Schroeder, Anurag A Agrawal, Christophe Duplais","doi":"10.1021/acs.jnatprod.4c00960","DOIUrl":"https://doi.org/10.1021/acs.jnatprod.4c00960","url":null,"abstract":"The common milkweed Asclepias syriaca is widespread in North America and produces cardenolide toxins that deter herbivores by targeting the transmembrane enzyme Na+/K+-ATPase. In 1979, Nobel Laureate Tadeus Reichstein elucidated the structure of novel cardenolides isolated from A. syriaca roots and proposed structures for several other cardenolides that could not be confirmed. In this study, we investigate the cardenolide composition of A. syriaca seeds, focusing on their abundance and in vitro inhibitory potency on the sensitive porcine Na+/K+-ATPase and that of the highly resistant large milkweed bug, Oncopeltus fasciatus. We identify five previously unreported cardenolides (1-5), three of which are predominantly found in seeds, in addition to the known syrioside (6), aspecioside (7), and the 2-thiazoline ring-containing cardenolide labriformin (8). Glucopyranosyl-allomethylosyl-12-deoxy aspecioside (5) is distinguished by lack of oxidation at C-12, and compounds 2, 3, 6, and 8 contain a rare 1,4-dioxane motif. Inhibitory efficacy of the isolated cardenolides for sensitive and resistant enzymes appears to be correlated. Finally, we confirmed the structure of compound 2, originally proposed by Tadeus Reichstein, and are pleased to share his original 1979 handwritten manuscript.","PeriodicalId":47,"journal":{"name":"Journal of Natural Products ","volume":" ","pages":""},"PeriodicalIF":3.3,"publicationDate":"2024-12-18","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"142845311","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

Breviane Spiroditerpenoids with Anti-inflammatory and Antiviral Activities from Deep-Sea-Derived Fungus Penicillium sp. F59.

IF 3.3 2区生物学

Journal of Natural Products Pub Date : 2024-12-17 DOI: 10.1021/acs.jnatprod.4c00997

Yinghui Lv, Wenping Song, Zongze Shao, Tianlei Ying, Bihong Hong, Wenjing Tian, Siwen Niu

{"title":"Breviane Spiroditerpenoids with Anti-inflammatory and Antiviral Activities from Deep-Sea-Derived Fungus Penicillium sp. F59.","authors":"Yinghui Lv, Wenping Song, Zongze Shao, Tianlei Ying, Bihong Hong, Wenjing Tian, Siwen Niu","doi":"10.1021/acs.jnatprod.4c00997","DOIUrl":"https://doi.org/10.1021/acs.jnatprod.4c00997","url":null,"abstract":"Twelve new breviane spiroditerpenoids, namely, chrysobreviones A-L (1-12), together with seven structurally related analogues (13-19) were isolated from the EtOAc extract of the fermented cultures of deep-sea-derived fungus Penicillium sp. F59. These structures including absolute configurations were resolved on the basis of extensive analysis of NMR spectroscopic data and HRESIMS, in association with experimental and calculated ECD data as well as the modified Mosher's method. Compound 1 represented the first breviane derivative containing an unusual octahydrodifuro[2,3-b:2',3'-d]furan moiety, while 7 and 9 were the first breviones featuring an epoxy ring and an 18-hydroxymethyl group, respectively. The anti-inflammatory and antiviral activities of compounds 1-19 were evaluated. Compounds 1, 8, 16, and 17 showed inhibitory effects against NO secretion in LPS-activated Raw264.7 macrophage cells with IC50 values ranging from 1.4 to 12.9 μM, while 1 and 7 exhibited antiviral effects against severe acute respiratory syndrome coronavirus-2 (SARS-CoV-2) omicron subvariant BA.2 pseudovirus with IC50 values of 8.5 and 10.3 μM, respectively.","PeriodicalId":47,"journal":{"name":"Journal of Natural Products ","volume":" ","pages":""},"PeriodicalIF":3.3,"publicationDate":"2024-12-17","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"142833095","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

Chromones Featuring a [6,6]-Spiroketal Moiety Produced by Coculture of the Endophytic Fungi Chaetomium virescens and Xylaria Grammica.

IF 3.3 2区生物学

Journal of Natural Products Pub Date : 2024-12-17 DOI: 10.1021/acs.jnatprod.4c00773

Sitian Zhang, Nanjing Ding, Xinyu Zheng, Yuling Lu, Jiangchun Wei, Hanxiao Zeng, Weiguang Sun, Yuan Zhou, Ya Gao, Yonghui Zhang, Zhengxi Hu

{"title":"Chromones Featuring a [6,6]-Spiroketal Moiety Produced by Coculture of the Endophytic Fungi Chaetomium virescens and Xylaria Grammica.","authors":"Sitian Zhang, Nanjing Ding, Xinyu Zheng, Yuling Lu, Jiangchun Wei, Hanxiao Zeng, Weiguang Sun, Yuan Zhou, Ya Gao, Yonghui Zhang, Zhengxi Hu","doi":"10.1021/acs.jnatprod.4c00773","DOIUrl":"https://doi.org/10.1021/acs.jnatprod.4c00773","url":null,"abstract":"Under the guidance of HPLC-DAD analysis, ten new chromones featuring a rare [6,6]-spiroketal moiety, namely chaetovirexylariones A-J (1-10), together with two known congeners (11-12), were isolated from coculture of the endophytic fungi Chaetomium virescens and Xylaria grammica, from the rhizome of the medicinal plant Smilax glabra Roxb. Their structures were elucidated via a combination of NMR and HRESIMS data, and the absolute configurations of 1-10 were determined by the chemical conversion and single-crystal X-ray diffraction (Cu Kα) experiments, as well as the comparison of the experimental and calculated electronic circular dichroism (ECD) data. Compound 6 is the first report as a racemate of this type of natural product. Compound 10 represents the first example of a [6,6]-spiroketal chromone bearing a 5-amino-3-methyl-2-pentenoic acid fragment. Compound 8 demonstrated a reduction in PTX resistance of SW620/AD300 by a factor of 45, and had the potential to be an effective P-gp inhibitor and an antitumor chemotherapy sensitizer.","PeriodicalId":47,"journal":{"name":"Journal of Natural Products ","volume":" ","pages":""},"PeriodicalIF":3.3,"publicationDate":"2024-12-17","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"142833102","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

Phenalenones and Polyesters from Talaromyces stipitatus and Structure Revision of Talaromycesone A.

IF 3.3 2区生物学

Journal of Natural Products Pub Date : 2024-12-16 DOI: 10.1021/acs.jnatprod.4c00885

Nirmal K Chaudhary, Daniel Vuong, Ernest Lacey, Andrew M Piggott, Peter Karuso

引用次数: 0

Is Linalyl Anthranilate Indeed Found In Plant Samples? GC-MS Misidentifications in the Scientific Literature.

IF 3.3 2区生物学

Journal of Natural Products Pub Date : 2024-12-16 DOI: 10.1021/acs.jnatprod.4c01118

Katarzyna Pokajewicz, Tomasz Biernat, Piotr P Wieczorek

{"title":"Is Linalyl Anthranilate Indeed Found In Plant Samples? GC-MS Misidentifications in the Scientific Literature.","authors":"Katarzyna Pokajewicz, Tomasz Biernat, Piotr P Wieczorek","doi":"10.1021/acs.jnatprod.4c01118","DOIUrl":"https://doi.org/10.1021/acs.jnatprod.4c01118","url":null,"abstract":"Linalyl anthranilate (LNA) has been identified in a number of plant extracts and essential oils by various authors using gas chromatography-mass spectrometry (GC-MS). However, the reported retention behavior of LNA in these studies is inconsistent with the retention data provided in the NIST database. Therefore, the objective of this study was to determine whether the reports of LNA were the result of misidentifications in GC-MS analyses or if the linear NIST retention index was inaccurate. To accomplish this, linalyl anthranilate was synthesized in a two-step procedure, and the resulting product was authenticated using nuclear magnetic resonance (NMR) and GC-MS analyses. This is a new synthetic route to linalyl anthranilate. Subsequently, retention indices for linalyl anthranilate were determined on three commonly used GC phases: polydimethylsiloxane, 5% diphenyl-95% polydimethylsiloxane, and polyethylene glycol. The study confirmed the accuracy of the NIST retention data, establishing the linear retention index data for LNA on a semi-nonpolar GC column as 2051. However, LNA reported in the literature by various authors exhibited a retention index in the elution window of approximately 1000-1400, strongly suggesting that these reports were the result of GC-MS misidentifications. A review of all reported occurrences of LNA in natural samples found no credible evidence of its presence. In many cases, it appears to be a misidentification of linalyl acetate caused by the occurrence of an erroneous spectrum in the older versions of the NIST mass spectra database.","PeriodicalId":47,"journal":{"name":"Journal of Natural Products ","volume":" ","pages":""},"PeriodicalIF":3.3,"publicationDate":"2024-12-16","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"142833104","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 of Cyclic Lipopeptides, Octaminomycins C and D, by Engineering LysR Transcriptional Regulator of Streptomyces sp.

IF 3.3 2区生物学

Journal of Natural Products Pub Date : 2024-12-13 DOI: 10.1021/acs.jnatprod.4c01047

Joon Soo An, Jung Min Kim, Jaeho Han, Jun Young Lee, Sang-Jip Nam, Sang Kook Lee, Yeo Joon Yoon, Dong-Chan Oh

引用次数: 0