Journal of Natural Products 最新文献_第5页

Total Synthesis and Reconfirmation of the Absolute Configuration of (3R,4S)-6-Acetyl-3-hydroxy-7-methoxy-2,2-dimethylchroman-4-yl(Z)-2-methylbut-2-enoate Isolated from Ageratina grandifolia 桔梗中(3R,4S)-6-乙酰-3-羟基-7-甲氧基-2,2-二甲基铬-4-基(Z)-2-甲基丁-2-烯酸酯的全合成及绝对构型的再确认

IF 3.3 2区生物学

Journal of Natural Products Pub Date : 2025-04-28 DOI: 10.1021/acs.jnatprod.5c0026910.1021/acs.jnatprod.5c00269

Sanket S. Shete, Swetha Balamurugan and D. Srinivasa Reddy*,

引用次数: 0

Heterologous Expression of the Fellutanine Biosynthetic Gene Cluster and Characterization of the Dual Prenylation of cyclo(l-Trp-l-Trp) by a Single DMATS Enzyme 费芦氨酸生物合成基因簇的异源表达及单DMATS酶对环（l-Trp-l-Trp）双戊酰化的表征

IF 3.3 2区生物学

Journal of Natural Products Pub Date : 2025-04-27 DOI: 10.1021/acs.jnatprod.4c0111610.1021/acs.jnatprod.4c01116

Wei-Peng Chen, Wei Lin, Wei Chen, Shu-zhen Chen, Jian-Bin Xiao, Xing-Tong Chen, Chao Chen, Fan Cai, Ming-Liang Zhang, Qin Li, Huai-Dong Zhang*, Li Li* and Hui Zhang*,

{"title":"Heterologous Expression of the Fellutanine Biosynthetic Gene Cluster and Characterization of the Dual Prenylation of cyclo(l-Trp-l-Trp) by a Single DMATS Enzyme","authors":"Wei-Peng Chen, Wei Lin, Wei Chen, Shu-zhen Chen, Jian-Bin Xiao, Xing-Tong Chen, Chao Chen, Fan Cai, Ming-Liang Zhang, Qin Li, Huai-Dong Zhang*, Li Li* and Hui Zhang*, ","doi":"10.1021/acs.jnatprod.4c0111610.1021/acs.jnatprod.4c01116","DOIUrl":"https://doi.org/10.1021/acs.jnatprod.4c01116https://doi.org/10.1021/acs.jnatprod.4c01116","url":null,"abstract":"2,5-Diketopiperazines (2,5-DKPs) are recognized for their structural rigidity and diverse bioactivities, making them significant in drug discovery. However, the stereochemical complexity of 2,5-DKPs presents challenges in chemical synthesis, particularly concerning indole derivatives such as indole diketopiperazines (IDKPs). Prenylation and oxidation further diversify these structures, enhancing their bioactivity and membrane affinity. Despite recent advances, the biosynthetic pathways of IDKPs, especially those involving dual prenylation, remain inadequately understood. In this study, the fellutanine biosynthetic gene cluster from Nannizzia fulva was cloned and heterologously expressed in Aspergillus nidulans. A partially oxidized intermediate in the fellutanine biosynthetic pathway was characterized. The dimethylallyl tryptophan synthase (DMATS) enzyme FelB was shown to catalyze consecutive prenylations at two C-2 positions of cyclo(l-Trp-l-Trp) in both in vivo and in vitro assays. Additionally, comparative studies with the known DMATS enzyme OkaC revealed differences in the regioselectivity. Furthermore, the biprenylation mechanism of FelB and OkaC was elucidated through molecular docking and active site analysis.","PeriodicalId":47,"journal":{"name":"Journal of Natural Products ","volume":"88 5","pages":"1111–1119 1111–1119"},"PeriodicalIF":3.3,"publicationDate":"2025-04-27","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"144114623","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

Dichloromethyl-Containing Derivatives from Streptomyces agglomeratus 5-2-6, a Soil Bacterium Isolated from the Qinghai-Tibet Plateau. 青藏高原土壤细菌凝集链霉菌5-2-6的含二氯甲基衍生物

IF 3.3 2区生物学

Journal of Natural Products Pub Date : 2025-04-25 Epub Date: 2025-03-24 DOI: 10.1021/acs.jnatprod.4c01248

Doudou Dong, Wei Zhang, Wei Ding

{"title":"Dichloromethyl-Containing Derivatives from Streptomyces agglomeratus 5-2-6, a Soil Bacterium Isolated from the Qinghai-Tibet Plateau.","authors":"Doudou Dong, Wei Zhang, Wei Ding","doi":"10.1021/acs.jnatprod.4c01248","DOIUrl":"10.1021/acs.jnatprod.4c01248","url":null,"abstract":"Six novel dichloromethyl-containing polyketides (1-6), including four pyranone analogs (1-4) and two furanone isomers (5, 6), were isolated from Streptomyces agglomeratus 5-2-6, which was obtained from the Qinghai-Tibet Plateau, China. Additionally, two new linear dichloromethyl compounds (7, 8) were obtained via heterologous expression of agg(A-K) in Streptomyces coelicolor M1152. The structures and absolute configurations of these compounds were primarily elucidated via high-resolution ESIMS, NMR, Mo2(OAc)4-induced electronic circular dichroism, and application of the modified Mosher's method. Notably, 1-6 feature a dichloromethyl moiety, which is reported for the first time in pyranone- and furanone-type natural products. Furthermore, the results of in vivo gene deletion, isotope labeling, and in vitro enzyme reaction experiments revealed a rare single-component flavin-dependent halogenase, AggA, which catalyzes the dichlorination of activated sp3-methylene groups.","PeriodicalId":47,"journal":{"name":"Journal of Natural Products ","volume":" ","pages":"896-906"},"PeriodicalIF":3.3,"publicationDate":"2025-04-25","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"143690492","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

Unifying the Absolute Configuration of Dibenzopyrrocoline Alkaloids with Relative Configuration Revision of Cryptowolinol and Description of Isocryptaustoline from Cryptocarya oubatchensis. 二苯并吡咯碱类生物碱的绝对构型与隐油酚的相对构型的统一及隐油酚异隐油酚的描述。

IF 3.3 2区生物学

Journal of Natural Products Pub Date : 2025-04-25 Epub Date: 2025-03-31 DOI: 10.1021/acs.jnatprod.4c01315

Rany B Mbeng Obame, Sidney Gallard, Sacha Gibert, Jean-François Gallard, Solenn Ferron, Blandine Séon-Méniel, Guillaume Bernadat, Mehdi A Beniddir, Pierre Le Pogam

{"title":"Unifying the Absolute Configuration of Dibenzopyrrocoline Alkaloids with Relative Configuration Revision of Cryptowolinol and Description of Isocryptaustoline from Cryptocarya oubatchensis.","authors":"Rany B Mbeng Obame, Sidney Gallard, Sacha Gibert, Jean-François Gallard, Solenn Ferron, Blandine Séon-Méniel, Guillaume Bernadat, Mehdi A Beniddir, Pierre Le Pogam","doi":"10.1021/acs.jnatprod.4c01315","DOIUrl":"10.1021/acs.jnatprod.4c01315","url":null,"abstract":"Dibenzopyrrocoline alkaloids, found in lauraceous and hernandiaceous plants, have been studied since the 1950s. The absolute configuration of these alkaloids, including cryptaustoline, has been a topic of debate due to conflicting studies. Having in our laboratory some authentic samples of dibenzopyrrocoline-type Cryptocarya alkaloids, we decided to reinvestigate their absolute configuration using modern spectroscopic techniques along with TDDFT calculations. The NMR reinvestigation of the authentic sample of cryptowolinol led us to revise its relative configuration using ML-J-DP4 and DP4+ analyses. Moreover, the absolute configuration of all dibenzopyrrocoline alkaloids reported to date benefitted from a complete re-evaluation based on a comparison with TDDFT-SR and TDDFT-ECD predictions leading to a unified absolute configuration. At last, this patrimonial reinvestigation unveiled a historical sample corresponding to a heretofore unpublished dibenzopyrrocoline alkaloid, which we named isocryptaustoline. The reisolation of this molecule from the total alkaloid extract of Cryptocarya oubatchensis makes it a genuine natural product.","PeriodicalId":47,"journal":{"name":"Journal of Natural Products ","volume":" ","pages":"935-942"},"PeriodicalIF":3.3,"publicationDate":"2025-04-25","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"143750272","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

Emerging Investigators at the Forefront of Natural Products Research. 天然产物研究前沿的新兴研究者。

IF 3.3 2区生物学

Journal of Natural Products Pub Date : 2025-04-25 DOI: 10.1021/acs.jnatprod.5c00229

Bradley S Moore, Sonja Krane, Roberto Berlinck, Katherine Maloney, Cedric Pearce, Philip Proteau

引用次数: 0

Topical Application of Oxylipin (3S)-16,17-Didehydrofalcarinol in Mice Infected with Leishmania mexicana: A Possible Treatment for Localized Cutaneous Leishmaniasis. 氧脂素(3S)-16,17-双去氢镰藻醇局部应用于感染墨西哥利什曼原虫的小鼠：一种治疗局部皮肤利什曼病的可能方法。

IF 3.3 2区生物学

Journal of Natural Products Pub Date : 2025-04-25 Epub Date: 2025-04-03 DOI: 10.1021/acs.jnatprod.4c01411

Ana G Carrillo-Aké, José Delgado-Domínguez, Rocely Buenaventura Cervantes-Sarabia, Adriana Ruiz-Remigio, Jaime Zamora-Chimal, Norma Salaiza-Suazo, Luis W Torres-Tapia, Sergio R Peraza-Sánchez, Ingeborg Becker

{"title":"Topical Application of Oxylipin (3S)-16,17-Didehydrofalcarinol in Mice Infected with Leishmania mexicana: A Possible Treatment for Localized Cutaneous Leishmaniasis.","authors":"Ana G Carrillo-Aké, José Delgado-Domínguez, Rocely Buenaventura Cervantes-Sarabia, Adriana Ruiz-Remigio, Jaime Zamora-Chimal, Norma Salaiza-Suazo, Luis W Torres-Tapia, Sergio R Peraza-Sánchez, Ingeborg Becker","doi":"10.1021/acs.jnatprod.4c01411","DOIUrl":"10.1021/acs.jnatprod.4c01411","url":null,"abstract":"Pentavalent antimonials are the first-line treatment for localized cutaneous leishmaniasis. However, they have disadvantages such as their elevated toxicity, high costs, and parenteral application. Plant-derived compounds may be an alternative treatment against this disease. Previous in vitro studies have shown that (3S)-16,17-didehydrofalcarinol (1), a polyacetylene oxylipin isolated from Tridax procumbens, is active against Leishmania mexicana. We have analyzed the mechanism of action of compound 1, evaluating reactive oxygen species production, apoptosis of L. mexicana, cytotoxicity in murine macrophages, and its efficacy in controlling the disease progression and parasite load when applied topically in C57BL/6 mice infected with L. mexicana. Results show that parasites incubated with 1.6 μM compound 1 significantly increased reactive oxygen species production (p ≤ 0.05). The percentage of apoptosis also increased significantly (p ≤ 0.05) and did not affect the viability of macrophages. The application of the topical formulations with 0.5% and 0.75% compound 1 for 7 weeks reduced disease progression and parasite load. We demonstrate that compound 1 generates the death of L. mexicana by apoptosis through reactive oxygen species production. We conclude that compound 1 can be used a possible alternative treatment for localized cutaneous leishmaniasis, enabling a less painful and more accessible therapy.","PeriodicalId":47,"journal":{"name":"Journal of Natural Products ","volume":" ","pages":"959-966"},"PeriodicalIF":3.3,"publicationDate":"2025-04-25","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"https://www.ncbi.nlm.nih.gov/pmc/articles/PMC12038837/pdf/","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"143778608","PeriodicalName":null,"FirstCategoryId":null,"ListUrlMain":null,"RegionNum":2,"RegionCategory":"生物学","ArticlePicture":[],"TitleCN":null,"AbstractTextCN":null,"PMCID":"OA","EPubDate":null,"PubModel":null,"JCR":null,"JCRName":null,"Score":null,"Total":0}

引用次数: 0

Chiral Optical Sensing of Amino Acids with 2-Trifluoromethyl Benzaldehyde for Ophiopogon japonicus Authentication. 2-三氟甲基苯甲醛对麦冬氨基酸的手性光学传感鉴定。

IF 3.3 2区生物学

Journal of Natural Products Pub Date : 2025-04-25 Epub Date: 2025-03-26 DOI: 10.1021/acs.jnatprod.4c01389

Xijian Wu, Zijie Su, Biling Huang, Xin Peng, Xing Zhang, Shaohua Huang

引用次数: 0

IF 3.3 2区生物学

Journal of Natural Products Pub Date : 2025-04-25 Epub Date: 2025-03-31 DOI: 10.1021/acs.jnatprod.5c00109

Liangguang Yi, Chan Guo, Qiao Yan, Martin G Banwell, Yu-Tao He, Ya-Jian Hu, Michelle L Coote, Zhipeng Pei, Li-Juan Yu, Jas S Ward, Steven E Bottle

{"title":"Studies Related to the Proposed Biotransformation of Bohemamine D into the Co-occurring Marine Natural Product Spinoxazine B.","authors":"Liangguang Yi, Chan Guo, Qiao Yan, Martin G Banwell, Yu-Tao He, Ya-Jian Hu, Michelle L Coote, Zhipeng Pei, Li-Juan Yu, Jas S Ward, Steven E Bottle","doi":"10.1021/acs.jnatprod.5c00109","DOIUrl":"10.1021/acs.jnatprod.5c00109","url":null,"abstract":"The 1,3-oxazin-6-one-containing spinoxazines A and B (2 and 3, respectively) have been isolated from the marine-derived Streptomyces spinoverrucosus strain SNB-048 and, by another group, from the Solar Saltern-derived Streptomyces sp. KMF-004. Two distinct pathways have been proposed for the conversion of the co-occurring pyrrolizidine alkaloid bohemamine D (1) into compound 3. Here, we report that the readily prepared compound 10, which embodies the 2-hydroxy-1,2-dihydro-3H-pyrrol-3-one core of bohemamine D (1) and is the bis-O-methyl ether of the alkaloid discoipyrrole C, is converted into 1,3-oxazin-6-one 11 on heating at elevated temperatures in air. The mechanism of this conversion was studied using density functional theory and the biosynthetic implications of it are discussed. The photochemical reaction of compound 10 in the presence of oxygen is also detailed and, again, the possible biosynthetic implications of the resulting conversion are considered.","PeriodicalId":47,"journal":{"name":"Journal of Natural Products ","volume":" ","pages":"1004-1011"},"PeriodicalIF":3.3,"publicationDate":"2025-04-25","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"143750267","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

Emerging Investigators at the Forefront of Natural Products Research 天然产物研究前沿的新兴研究者

IF 3.3 2区生物学

Journal of Natural Products Pub Date : 2025-04-25 DOI: 10.1021/acs.jnatprod.5c0022910.1021/acs.jnatprod.5c00229

Bradley S. Moore*, Sonja Krane, Roberto Berlinck, Katherine Maloney, Cedric Pearce and Philip Proteau,

引用次数: 0

Semisynthetic Derivatives of Perovskone: Development of a Promising Class of Antiprotozoal Lead Compounds. 钙钛矿半合成衍生物：一类有前途的抗原虫先导化合物的开发。

IF 3.3 2区生物学

Journal of Natural Products Pub Date : 2025-04-25 Epub Date: 2025-04-07 DOI: 10.1021/acs.jnatprod.5c00138

Mona Kamelan Zargar Zarin, Mahdi Moridi Farimani, Mostafa Alilou, Farzaneh Azargoon, Marcel Kaiser, Thomas Gelbrich, Marzieh Tabefam, Peyman Salehi

{"title":"Semisynthetic Derivatives of Perovskone: Development of a Promising Class of Antiprotozoal Lead Compounds.","authors":"Mona Kamelan Zargar Zarin, Mahdi Moridi Farimani, Mostafa Alilou, Farzaneh Azargoon, Marcel Kaiser, Thomas Gelbrich, Marzieh Tabefam, Peyman Salehi","doi":"10.1021/acs.jnatprod.5c00138","DOIUrl":"10.1021/acs.jnatprod.5c00138","url":null,"abstract":"Perovskones, intricate triterpenoids with potent antiplasmodial activity, predominantly derive from Salvia hydrangea DC. ex Benth. In this study, ample quantities of the parent compound, perovskone (1), were isolated from the plant. Using perovskone (1) as a feedstock, seven semisynthetic analogues (2-8) were generated via reactions like hydroxylation, elimination, and esterification. Structural characterization was performed by using 1D and 2D NMR, HRMS, and X-ray diffraction experiments. The compounds underwent in vitro antiparasitic testing against Leishmania donovani, Trypanosoma brucei rhodesiense, Plasmodium falciparum, and Trypanosoma cruzi. Cytotoxicity evaluation was performed using rat myoblast (L6) cells. Perovskone (1) demonstrated excellent activity against T. cruzi, showing an IC50 value of 0.89 μM and a selectivity index (SI) of 14.9. Perovskone I (4) and perovskone G (2) exhibited potent activity against P. falciparum (IC50 values of 0.03 and 0.08 μM, respectively), with favorable SIs of 843.0 and 80.0, comparable to those of chloroquine and artemisinin. Perovskone M (8) displayed promising antileishmanial activity (IC50 = 0.44 μM, SI = 22), comparable to the efficacy of miltefosine against L. donovani (IC50 = 0.51 μM). We believe that the current study holds immense potential for the development of promising leads in antiplasmodial drug discovery.","PeriodicalId":47,"journal":{"name":"Journal of Natural Products ","volume":" ","pages":"1041-1047"},"PeriodicalIF":3.3,"publicationDate":"2025-04-25","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"143802034","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