Journal of Natural Products 最新文献_第10页

Goondolinones A and B: Terpenyl-quinolin-4(1H)-ones from an Australian Volcanic Crater Soil-Derived Actinomadura sp., with Selective Activity against Dirofilaria immitis (Heartworm). Goondolinones A and B: Terpenyl-quinolin-4(1H)-ones from an Australian Volcanic Crater Soil-Derived Actinomadura sp.

IF 3.3 2区生物学

Journal of Natural Products Pub Date : 2024-12-27 Epub Date: 2024-11-24 DOI: 10.1021/acs.jnatprod.4c01146

Jianying Han, David F Bruhn, Dana C Roberts, Erica J Burkman, Yovany Moreno, Paul V Bernhardt, Angela A Salim, Robert J Capon

{"title":"Goondolinones A and B: Terpenyl-quinolin-4(1H)-ones from an Australian Volcanic Crater Soil-Derived Actinomadura sp., with Selective Activity against Dirofilaria immitis (Heartworm).","authors":"Jianying Han, David F Bruhn, Dana C Roberts, Erica J Burkman, Yovany Moreno, Paul V Bernhardt, Angela A Salim, Robert J Capon","doi":"10.1021/acs.jnatprod.4c01146","DOIUrl":"10.1021/acs.jnatprod.4c01146","url":null,"abstract":"A chemical investigation of the Australian pasture soil-derived Actinomadura sp. S4S-00245B09, supported by chemical, bioactivity and cultivation profiling, yielded a new class of terpenyl-quinolin-4(1H)-ones, goondolinones A and B (1 and 2), featuring an unprecedented fused seven-membered ether. Structures were assigned to 1 and 2 on the basis of detailed spectroscopic analysis, including X-ray analysis of 1, and biosynthetic considerations. Goondolinone A (1) lacks antibacterial or antifungal properties, is noncytotoxic to two human carcinoma cell lines, but exhibits selective inhibition of the motility of heartworm Dirofilaria immitis microfilaria (EC50 5.1 μM) and L4 larvae (EC50 21.4 μM). As a new anthelmintic scaffold, future understanding of the structure activity relationship and mechanism of action of 1 could inform the discovery of new treatments for heartworm and other filarial diseases, capable of safeguarding the health and welfare of companion animals.","PeriodicalId":47,"journal":{"name":"Journal of Natural Products ","volume":" ","pages":"2855-2862"},"PeriodicalIF":3.3,"publicationDate":"2024-12-27","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"142708598","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

Goondomycins A-H: Carbocyclic ansa-Polyketides from an Australian Pasture Streptomyces with Selective Activity against Dirofilaria immitis. Goondomycins A-H: Carbocyclic ansa-Polyketides from an Australian Pasture Streptomyces with Selective Activity against Dirofilaria immitis.

IF 3.3 2区生物学

Journal of Natural Products Pub Date : 2024-12-27 Epub Date: 2024-11-26 DOI: 10.1021/acs.jnatprod.4c00987

Jianying Han, David F Bruhn, Dana C Roberts, Erica Burkman, Yovany Moreno, Angela A Salim, Robert J Capon

引用次数: 0

Spiro-meroterpenoids, Syzygioblanes D-H, Isolated from Indonesian Medicinal Plant Syzygium oblanceolatum. 从印尼药用植物斜针叶桐中分离的螺粒萜类化合物，syzygioblane D-H。

IF 3.3 2区生物学

Journal of Natural Products Pub Date : 2024-12-27 Epub Date: 2024-12-13 DOI: 10.1021/acs.jnatprod.4c01154

Nona Koga, Kaede Kawashima, Chihiro Ito, Tomoya Nishida, Shuichi Fukuyoshi, Yohei Saito, Katsunori Miyake, Saidanxia Amuti, Abdul Rahim, Ahmad Najib, Gemini Alam, Atsushi Mizokami, Nobuyuki Tanaka, Kyoko Nakagawa-Goto

{"title":"Spiro-meroterpenoids, Syzygioblanes D-H, Isolated from Indonesian Medicinal Plant Syzygium oblanceolatum.","authors":"Nona Koga, Kaede Kawashima, Chihiro Ito, Tomoya Nishida, Shuichi Fukuyoshi, Yohei Saito, Katsunori Miyake, Saidanxia Amuti, Abdul Rahim, Ahmad Najib, Gemini Alam, Atsushi Mizokami, Nobuyuki Tanaka, Kyoko Nakagawa-Goto","doi":"10.1021/acs.jnatprod.4c01154","DOIUrl":"10.1021/acs.jnatprod.4c01154","url":null,"abstract":"Syzygioblanes A-C (1-3), isolated from the Indonesian traditional herbal medicine Syzygium oblanceolatum (S. oblanceolatum), are meroterpenoids with a spiro ring formed through a [4 + 2] cycloaddition of the flavanone desmethoxymatteucinol with cyclic sesquiterpenoids. Our ongoing phytochemical investigation of S. oblanceolatum resulted in the isolation of five additional spiro-meroterpenoids, syzygioblanes D-H (4-8), which are hybrids of the same flavanone with eudesmane/cadinane-type sesquiterpenoids. A possible biosynthetic pathway involves enzymatic dearomative hydroxylation of desmethoxymatteucinol followed by [4 + 2] cyclization of the resulting diene with a cyclic sesquiterpene containing an exocyclic methylene to form the unique spiro ring in the syzygioblane molecule. The isolated syzygioblanes F (6) and G (7) demonstrated collateral sensitivity by inhibiting the growth of multidrug-resistant tumor cell lines more than the related chemosensitive tumor cell lines.","PeriodicalId":47,"journal":{"name":"Journal of Natural Products ","volume":" ","pages":"2872-2880"},"PeriodicalIF":3.3,"publicationDate":"2024-12-27","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"142816775","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

Correction to Triterpenoid Saponins from Dianthus versicolor. 石竹中三萜皂苷的校正。

IF 3.3 2区生物学

Journal of Natural Products Pub Date : 2024-12-27 Epub Date: 2024-12-04 DOI: 10.1021/acs.jnatprod.4c01363

Li Ma, Yu-Cheng Gu, Jian-Guang Luo, Jun-Song Wang, Xue-Feng Huang, Ling-Yi Kong

引用次数: 0

Tyrosinase Inhibitory Properties of Compounds Isolated from Artocarpus integer Roots. 从整叶蒿根中分离出的化合物对酪氨酸酶的抑制特性

IF 3.3 2区生物学

Journal of Natural Products Pub Date : 2024-12-27 Epub Date: 2024-11-18 DOI: 10.1021/acs.jnatprod.4c00957

Ittipon Siridechakorn, Dina Nur Shinta, Ardiansah Ardiansah, Paratchata Batsomboon, Nattaya Ngamrojanavanich, Siwattra Choodej, Khanitha Pudhom

引用次数: 0

Synthesis and Evaluation of 9-epi-Koshidacin B as Selective Inhibitor of Histone Deacetylase 1. 9-epi-Koshidacin B选择性组蛋白去乙酰化酶1抑制剂的合成及评价

IF 3.3 2区生物学

Journal of Natural Products Pub Date : 2024-12-27 Epub Date: 2024-12-10 DOI: 10.1021/acs.jnatprod.4c00913

Rajat Ghosh, Sima Biswas, Angshuman Bagchi, Shital K Chattopadhyay

引用次数: 0

Synthesis, Biological Evaluation, and Mechanistic Insights of Rubrolide Analogues as Antitumor Agents. 作为抗肿瘤药物的 Rubrolide 类似物的合成、生物学评价和机理研究。

IF 3.3 2区生物学

Journal of Natural Products Pub Date : 2024-12-27 Epub Date: 2024-11-28 DOI: 10.1021/acs.jnatprod.4c00946

Haoyu Wu, Guangyao Lv, Liying Liu, Ruilin Hu, Feng Zhao, Mingxiang Song, Sisi Zhang, Huaying Fan, Shengjun Dai, Saif Ur Rehman, Hongbo Wang, Xiaofeng Mou

{"title":"Synthesis, Biological Evaluation, and Mechanistic Insights of Rubrolide Analogues as Antitumor Agents.","authors":"Haoyu Wu, Guangyao Lv, Liying Liu, Ruilin Hu, Feng Zhao, Mingxiang Song, Sisi Zhang, Huaying Fan, Shengjun Dai, Saif Ur Rehman, Hongbo Wang, Xiaofeng Mou","doi":"10.1021/acs.jnatprod.4c00946","DOIUrl":"10.1021/acs.jnatprod.4c00946","url":null,"abstract":"Marine natural products and their analogues have as of now been acknowledged as an important source of bioactive molecules for the treatment of cancer. Rubrolides, a unique group of γ-butenolides derived from marine microorganisms, have shown strong cytotoxic activity against various tumor cells. In this study, we synthesized and characterized 21 rubrolide analogues (including 16 new compounds) and investigated their antitumor activities in order to screen more active molecules and elucidate their mechanism of action. Primary MTT assay showed that compounds 1 and 4-9 all exhibited excellent antiproliferative activities. In particular, compound 7 showed broad-spectrum cytotoxic activity against six tumor cell lines, with IC50 values mostly ranging from 2.5 to 0.2 μM. Further mechanistic studies revealed that compound 7 could penetrate HCT116 and Hela cells, localize in the endoplasmic reticulum, and upregulate the PERK-eIF2α-CHOP pathway, inducing ER stress and increasing intracellular reactive oxygen species (ROS) levels to ultimately trigger apoptosis in tumor cells. Additionally, compound 7 was found to upregulate Cyclin B1 protein expression, causing cell cycle reticulum at the G2/M phase. In vivo studies further demonstrated that liposomal delivery of compound 7 exhibited a potent antitumor efficacy against Hela xenograft tumors. Based on these results, marine-derived rubrolide analogues show significant potential as novel lead compounds for antitumor drug development.","PeriodicalId":47,"journal":{"name":"Journal of Natural Products ","volume":" ","pages":"2779-2789"},"PeriodicalIF":3.3,"publicationDate":"2024-12-27","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"142737786","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 Chalcone Derivatives as Bifunctional Molecules with Anti-SARS-CoV-2 and Anti-inflammatory Activities. 发现具有抗 SARS-CoV-2 和抗炎活性的双功能分子查尔酮衍生物

IF 3.3 2区生物学

Journal of Natural Products Pub Date : 2024-12-27 Epub Date: 2024-11-14 DOI: 10.1021/acs.jnatprod.4c00657

Xuwen Chen, Hongtao Li, Meiting Wang, Donghui Sun, Jiani Lu, Tong Zhu, Hongzhuan Chen, Lili Chen, Shunying Liu

{"title":"Discovery of Chalcone Derivatives as Bifunctional Molecules with Anti-SARS-CoV-2 and Anti-inflammatory Activities.","authors":"Xuwen Chen, Hongtao Li, Meiting Wang, Donghui Sun, Jiani Lu, Tong Zhu, Hongzhuan Chen, Lili Chen, Shunying Liu","doi":"10.1021/acs.jnatprod.4c00657","DOIUrl":"10.1021/acs.jnatprod.4c00657","url":null,"abstract":"Danshensu extracted with traditional Chinese medicine Salvia miltiorrhiza has a wide range of bioactivities. Danshensu containing a catechol moiety has a moderate inhibitory effect on SARS-CoV-2 3CLpro (IC50 = 2.2 μM) by a reversible covalent interaction and exhibits good anti-inflammatory activity. To enhance the inhibitory activity, we introduced Michael receptors into the side chain of danshensu as a possible covalent warhead and blocked the covalent binding sites of catechol moiety to yield chalcone derivatives. The resulting chalcone derivatives, A4 and A7, were found to inhibit SARS-CoV-2 3CLpro in vitro with IC50 values of 83.2 and 261.3 nM, respectively. Furthermore, A4 and A7 inhibit viral replication in the SARS-CoV-2 replicon system with EC50 values of 19.9 and 11.7 μM, respectively. Time-dependent inhibition experiment and mass spectrometry show that A4 acted as a noncovalent mixed inhibitor, while A7 likely binds covalently at Cys145. The interaction mechanism between SARS-CoV-2 3CLpro and A4 or A7 was characterized by molecular docking studies. Additionally, both A4 and A7 demonstrated potent anti-inflammatory activity in lipopolysaccharide (LPS)-stimulated RAW264.7 macrophage cells. These promising results suggest that chalcone derivatives A4 and A7 can serve as bifunctional molecules with both antivirus and anti-inflammatory properties.","PeriodicalId":47,"journal":{"name":"Journal of Natural Products ","volume":" ","pages":"2680-2694"},"PeriodicalIF":3.3,"publicationDate":"2024-12-27","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"142612705","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

Semisynthesis of Nocarterphenyl A and Its Analogues

IF 3.3 2区生物学

Journal of Natural Products Pub Date : 2024-12-27 DOI: 10.1021/acs.jnatprod.4c0119810.1021/acs.jnatprod.4c01198

Yong Wang, Yanchao Xu, Dan Wu, Dongyang Wang, Peng Fu*, Weiming Zhu* and Liping Wang*,

{"title":"Semisynthesis of Nocarterphenyl A and Its Analogues","authors":"Yong Wang, Yanchao Xu, Dan Wu, Dongyang Wang, Peng Fu*, Weiming Zhu* and Liping Wang*, ","doi":"10.1021/acs.jnatprod.4c0119810.1021/acs.jnatprod.4c01198","DOIUrl":"https://doi.org/10.1021/acs.jnatprod.4c01198https://doi.org/10.1021/acs.jnatprod.4c01198","url":null,"abstract":"p-Terphenyl compounds are known to possess a diverse range of biological activities, making the synthesis of novel p-terphenyl derivatives a significant research objective. In this study, we report the first synthesis of nocarterphenyl A (1), characterized by a thiazole-fused p-terphenyl framework. Furthermore, we synthesized 18 additional analogs, including the naturally occurring compound 5-methoxy-4,7-bis(4-methoxyphenyl)benzo[d]thiazol-6-ol (9), employing a similar synthetic approach. Notably, compounds 12, 13, 15–17, and 19 demonstrated potent inhibitory effects against protein tyrosine phosphatase 1B (PTP1B), exhibiting IC50 values ranging from 2.2 to 7.9 μM, which are lower than that of oleanolic acid (13.2 μM). Additionally, compound 14 was found to inhibit α-glucosidase from human colorectal adenocarcinoma (Caco-2) cells with an IC50 value of 10.4 μM, which is also lower than that of acarbose (11.2 μM).","PeriodicalId":47,"journal":{"name":"Journal of Natural Products ","volume":"88 1","pages":"133–140 133–140"},"PeriodicalIF":3.3,"publicationDate":"2024-12-27","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"143086465","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

Pattern-Based Genome Mining Guides Discovery of the Antibiotic Indanopyrrole A from a Marine Streptomycete. 基于模式的基因组挖掘指导从海洋链霉菌中发现抗生素茚并吡咯 A。

IF 3.3 2区生物学

Journal of Natural Products Pub Date : 2024-12-27 Epub Date: 2024-11-22 DOI: 10.1021/acs.jnatprod.4c00934

Douglas Sweeney, Alexander Bogdanov, Alexander B Chase, Gabriel Castro-Falcón, Alma Trinidad-Javier, Samira Dahesh, Victor Nizet, Paul R Jensen

{"title":"Pattern-Based Genome Mining Guides Discovery of the Antibiotic Indanopyrrole A from a Marine Streptomycete.","authors":"Douglas Sweeney, Alexander Bogdanov, Alexander B Chase, Gabriel Castro-Falcón, Alma Trinidad-Javier, Samira Dahesh, Victor Nizet, Paul R Jensen","doi":"10.1021/acs.jnatprod.4c00934","DOIUrl":"10.1021/acs.jnatprod.4c00934","url":null,"abstract":"Terrestrial actinomycetes in the genus Streptomyces have long been recognized as prolific producers of small-molecule natural products, including many clinically important antibiotics and cytotoxic agents. Although Streptomyces can also be isolated from marine environments, their potential for natural product biosynthesis remains underexplored. The MAR4 clade of largely marine-derived Streptomyces has been a rich source of novel halogenated natural products of diverse structural classes. To further explore the biosynthetic potential of this group, we applied pattern-based genome mining, leading to the discovery of the first halogenated pyrroloketoindane natural products, indanopyrrole A (1) and B (2), and the bioinformatic linkage of these compounds to an orphan biosynthetic gene cluster (BCG) in 20 MAR4 genomes. Indanopyrrole A displays potent broad-spectrum antibiotic activity against clinically relevant pathogens. A comparison of the putative indanopyrrole BGC with that of the related compound indanomycin provides new insights into the terminal cyclization and offloading mechanisms in pyrroloketoindane biosynthesis. Broader searches of public databases reveal the rarity of this BGC while also highlighting opportunities for discovering additional compounds in this uncommon class.","PeriodicalId":47,"journal":{"name":"Journal of Natural Products ","volume":" ","pages":"2768-2778"},"PeriodicalIF":3.3,"publicationDate":"2024-12-27","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"https://www.ncbi.nlm.nih.gov/pmc/articles/PMC11686505/pdf/","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"142685431","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