Journal of Natural Products 最新文献_第6页

Neuroprotective Indole Alkaloids from the Soil-Derived Fungus Trichocladium sp. XZ8

IF 3.3 2区生物学

Journal of Natural Products Pub Date : 2025-01-11 DOI: 10.1021/acs.jnatprod.4c0125010.1021/acs.jnatprod.4c01250

Xiao-Qi Duan, Xin-Yu Wang, Huai-Chang Qi, Yi-Jie Zhai* and Wen-Bo Han*,

{"title":"Neuroprotective Indole Alkaloids from the Soil-Derived Fungus Trichocladium sp. XZ8","authors":"Xiao-Qi Duan, Xin-Yu Wang, Huai-Chang Qi, Yi-Jie Zhai* and Wen-Bo Han*, ","doi":"10.1021/acs.jnatprod.4c0125010.1021/acs.jnatprod.4c01250","DOIUrl":"https://doi.org/10.1021/acs.jnatprod.4c01250https://doi.org/10.1021/acs.jnatprod.4c01250","url":null,"abstract":"A chemical investigation of the soil-derived fungus Trichocladium sp. XZ8 led to the isolation of five new indole alkaloids, trichindoles A–E (1–5), with diverse architectures, along with seven known analogues (6–12). Their structures were elucidated by extensive spectroscopic data analysis, and their absolute configurations were determined by single-crystal X-ray diffraction and modified Mosher’s method. Compound 1 is a polyketide-alkaloid hybrid incorporating a rare succinimide motif, and compound 2 represents the first example of a dimeric isopentenyl indole-containing alkaloid bridged by a propane-1,2-diol moiety. Compounds 1, 4, 8, 11, and 12 showed significant neuroprotective effects against RSL3-induced ferroptosis in PC12 cells at 10 μM. Moreover, 1 and 4 might ameliorate RSL3-induced ferroptosis through the regulation of the SLC7A11 pathway and ferritinophagy, suggesting their potential as promising lead compounds for the treatment of neurodegenerative diseases.","PeriodicalId":47,"journal":{"name":"Journal of Natural Products ","volume":"88 1","pages":"175–182 175–182"},"PeriodicalIF":3.3,"publicationDate":"2025-01-11","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"143087804","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

IF 3.3 2区生物学

Journal of Natural Products Pub Date : 2025-01-09 DOI: 10.1021/acs.jnatprod.4c0110910.1021/acs.jnatprod.4c01109

Yan Cheng, Davlat Akramov, Lola Yakhshilikova, Chengwei Zhu, Jie Lu, Jin Suo, Santhosh Pugazh, Hongjian Qin, Safomuddin Abduahadi, Jishan Qin, Tianwen Hu, Jingshan Shen, Feipu Yang* and Haji A. Aisa*,

{"title":"Structural Similarity in Natural Products Leading to Sample Misidentification: A Case Study of the Bisbenzylisoquinoline Alkaloids Oxyacanthine and Berbamine","authors":"Yan Cheng, Davlat Akramov, Lola Yakhshilikova, Chengwei Zhu, Jie Lu, Jin Suo, Santhosh Pugazh, Hongjian Qin, Safomuddin Abduahadi, Jishan Qin, Tianwen Hu, Jingshan Shen, Feipu Yang* and Haji A. Aisa*, ","doi":"10.1021/acs.jnatprod.4c0110910.1021/acs.jnatprod.4c01109","DOIUrl":"https://doi.org/10.1021/acs.jnatprod.4c01109https://doi.org/10.1021/acs.jnatprod.4c01109","url":null,"abstract":"The similar structures of natural compounds and the absence of NMR data for commercial products raise the risk of misidentification. This work reports a case in which purchased samples labeled as “berbamine” from 14 suppliers are oxyacanthine (1). The NMR data of all purchased samples were consistent. The X-ray crystallography characterization of one sample revealed it to be 1. The NMR data of 1 were fully assigned for the first time. Berbamine (2) was isolated from the roots of Berberis sieboldii Miq. The NMR data of 2 were assigned, and its crystal structure was reported for the first time. The authors intend to raise awareness and support the academic/industrial community through a study of this misidentification case.","PeriodicalId":47,"journal":{"name":"Journal of Natural Products ","volume":"88 1","pages":"191–198 191–198"},"PeriodicalIF":3.3,"publicationDate":"2025-01-09","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"143091299","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 Glycosmis pentaphylla Alkaloid Derivatives: Pyranoacridone-Hydroxamic Acid Cytotoxic Conjugates with HDAC and Topoisomerase II α Dual Inhibitory Activity. 五葡萄糖生物碱衍生物的半合成：吡喃吖啶酮-羟肟酸细胞毒偶联物与HDAC和拓扑异构酶II α双重抑制活性。

IF 3.3 2区生物学

Journal of Natural Products Pub Date : 2025-01-08 DOI: 10.1021/acs.jnatprod.4c00843

Parusu Kavya Teja, Bao Q Ly, Vinal Upadhyay, Sourav Das, Santosh Kumar Behera, Amit Mandoli, Dhaval K Shah, Siddheshwar K Chauthe

{"title":"Semisynthesis of Glycosmis pentaphylla Alkaloid Derivatives: Pyranoacridone-Hydroxamic Acid Cytotoxic Conjugates with HDAC and Topoisomerase II α Dual Inhibitory Activity.","authors":"Parusu Kavya Teja, Bao Q Ly, Vinal Upadhyay, Sourav Das, Santosh Kumar Behera, Amit Mandoli, Dhaval K Shah, Siddheshwar K Chauthe","doi":"10.1021/acs.jnatprod.4c00843","DOIUrl":"https://doi.org/10.1021/acs.jnatprod.4c00843","url":null,"abstract":"Inspired by our previous efforts in the semisynthetic modification of naturally occurring pyranoacridones, we report the targeted design and semisynthesis of dual inhibitors of HDAC and topoisomerase II α (Topo II α) derived from Glycosmis pentaphylla des-N-methylacronycine (1) and noracronycine (8) pyranoacridone alkaloids. Designed from the clinically approved SAHA, the cytotoxic pyranoacridone nuclei from the alkaloids served as the capping group, while a hydroxamic acid moiety functioned as the zinc-binding group. Out of 16 compounds evaluated in an in vitro cytotoxicity assay, KT32 (10c) with noracronycine (8) as the capping group and five-carbon linker hydroxamic acid side chains showed good cytotoxic activity with IC50 values of 1.0, 1.5, and 0.3 μM on MCF-7, CALU-3, and SCC-25 cell lines, respectively. KT32 (10c) showed potent HDAC inhibitory activity and partial Topo II α inhibitory activity in both enzyme assays. The SAR results strongly aligned with the predicted binding affinities from the molecular docking study. KT32 (10c) was further explored for a preliminary mechanistic understanding of SCC-25 cell lines. Flow cytometry analysis suggests that KT32 (10c) induces cell death through apoptosis, as evidenced by the substantial increase in the population of late apoptotic cells.","PeriodicalId":47,"journal":{"name":"Journal of Natural Products ","volume":" ","pages":""},"PeriodicalIF":3.3,"publicationDate":"2025-01-08","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"142941395","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

Cyclopenta[bc]benzopyran Derivatives and Limonoids from Aglaia edulis with Cytotoxic and Anti-DENV Activity

IF 3.3 2区生物学

Journal of Natural Products Pub Date : 2025-01-05 DOI: 10.1021/acs.jnatprod.4c0119410.1021/acs.jnatprod.4c01194

Ping Yi, Jian-Fei Qiu, Xiao-Meng Yang, Fei-Fei Chen, Jue Yang, Juan Liu, Jun Jin, Lian-Xin Qi, Xiao-Jiang Hao, Jia-Hong Wu* and Chun-Mao Yuan*,

{"title":"Cyclopenta[bc]benzopyran Derivatives and Limonoids from Aglaia edulis with Cytotoxic and Anti-DENV Activity","authors":"Ping Yi, Jian-Fei Qiu, Xiao-Meng Yang, Fei-Fei Chen, Jue Yang, Juan Liu, Jun Jin, Lian-Xin Qi, Xiao-Jiang Hao, Jia-Hong Wu* and Chun-Mao Yuan*, ","doi":"10.1021/acs.jnatprod.4c0119410.1021/acs.jnatprod.4c01194","DOIUrl":"https://doi.org/10.1021/acs.jnatprod.4c01194https://doi.org/10.1021/acs.jnatprod.4c01194","url":null,"abstract":"Eighteen cyclopenta[b]benzopyran derivatives (1–5 and 11–23) and 10 limonoids (6–10 and 24–28) were identified from Aglaia edulis, including 10 undescribed compounds (1–10), all of which were identified by analysis of spectroscopic data, electronic circular dichroism calculations, and X-ray crystallography studies. Nine compounds displayed significant cytotoxic activity against three cancer cells, with IC50 values of 3–900 nM. Sixteen compounds demonstrated potent antiviral activity on the dengue virus, with selectivity index values between 13.0 and 532.6. A mechanism of action investigation revealed that compound 11 may function as an eIF4E activator, which could suppress the expression of the E protein, thereby conferring significant activity against the dengue virus.","PeriodicalId":47,"journal":{"name":"Journal of Natural Products ","volume":"88 1","pages":"119–132 119–132"},"PeriodicalIF":3.3,"publicationDate":"2025-01-05","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"143090750","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

Anthelmintic Potential of Conjugated Long-Chain Fatty Acids Isolated from the Bioluminescent Mushroom Neonothopanus gardneri. 生物发光蘑菇加特纳新乳菇共轭长链脂肪酸的驱虫潜能

IF 3.3 2区生物学

Journal of Natural Products Pub Date : 2025-01-04 DOI: 10.1021/acs.jnatprod.4c00546

Maria D A Oliveira, Teresinha de Jesus A Dos S Andrade, Joaquim S C Junior, Nerilson Marques Lima, Hugo G Machado, Jioji N Tabudravu, Francisco das Chagas L Pinto, Lucas Fukui-Silva, Monique C Amaro, Josué de Moraes, Dulce Helena S Silva, Antônia Maria das Graças L Citó, Chistiane Mendes Feitosa

{"title":"Anthelmintic Potential of Conjugated Long-Chain Fatty Acids Isolated from the Bioluminescent Mushroom Neonothopanus gardneri.","authors":"Maria D A Oliveira, Teresinha de Jesus A Dos S Andrade, Joaquim S C Junior, Nerilson Marques Lima, Hugo G Machado, Jioji N Tabudravu, Francisco das Chagas L Pinto, Lucas Fukui-Silva, Monique C Amaro, Josué de Moraes, Dulce Helena S Silva, Antônia Maria das Graças L Citó, Chistiane Mendes Feitosa","doi":"10.1021/acs.jnatprod.4c00546","DOIUrl":"https://doi.org/10.1021/acs.jnatprod.4c00546","url":null,"abstract":"With praziquantel being the sole available drug for schistosomiasis, identifying novel anthelmintic agents is imperative. A chemical investigation of the fruiting body of the bioluminescent mushroom Neonothopanus gardneri Berk. resulted in the isolation of new conjugated long-chain fatty acids (8E,10E,12S,13S)-12,13-dihydroxy-7-oxo-octadeca-8,10-dienoic acid (1) and (7S,8S,9E,11E)-7,8-dihydroxy-13-oxo-octadeca-9,11-dienoic acid (2) and three previously described compounds, (7R,8R,9Z)-7,8-dihydroxyoctadec-9-enoic acid (3), (2E)-dec-2-ene-1,10-dioic acid (4), and a ketolactone marasmeno-1,15-dione (5). Their planar structures were elucidated based on 1D and 2D NMR and MS/MS spectroscopic analyses. Compound 3 displayed significant antiparasitic activity against Schistosoma mansoni ex vivo (EC50 < 10 μM). No toxicity was observed in mammalian cells or Caenorhabditis elegans.","PeriodicalId":47,"journal":{"name":"Journal of Natural Products ","volume":" ","pages":""},"PeriodicalIF":3.3,"publicationDate":"2025-01-04","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"142925810","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

Chemical Basis of the Traditional Ayurvedic Detoxification Process of the Toxic Medicinal Plant Plumbago zeylanica

IF 3.3 2区生物学

Journal of Natural Products Pub Date : 2025-01-03 DOI: 10.1021/acs.jnatprod.3c0097510.1021/acs.jnatprod.3c00975

Ankur Kumar Tanwar, Debanjan Chatterjee, Neha Jain, Shivam Sharma, Kulbhushan Tikoo and Inder Pal Singh*,

{"title":"Chemical Basis of the Traditional Ayurvedic Detoxification Process of the Toxic Medicinal Plant Plumbago zeylanica","authors":"Ankur Kumar Tanwar, Debanjan Chatterjee, Neha Jain, Shivam Sharma, Kulbhushan Tikoo and Inder Pal Singh*, ","doi":"10.1021/acs.jnatprod.3c0097510.1021/acs.jnatprod.3c00975","DOIUrl":"https://doi.org/10.1021/acs.jnatprod.3c00975https://doi.org/10.1021/acs.jnatprod.3c00975","url":null,"abstract":"Certain medicinal plants utilized in the traditional ayurvedic system are poisonous when used raw, but are used following a detoxification process. The Ayurvedic Formulary of India (AFI) provides details about these detoxification (known as “sodhana”) processes as per traditional procedures. This research endeavor aimed to uncover the fundamental principles underlying the detoxification approach applied to Plumbago zeylanica, commonly referred to as “swet chitrak”, in which plumbagin is the primary toxic constituent. Both unprocessed and processed (detoxified) extracts as well as the detoxification media were subjected to analysis for secondary metabolites using different analytical techniques. This investigation revealed a reduction in plumbagin content, its conversion to epoxyplumbagin and zeylanone and a noteworthy decrease in cis- and trans-isoshinanolone during detoxification. Furthermore, it was confirmed that pure plumbagin when subjected to the same detoxification conditions, is partially converted into epoxyplumbagin, and that cis and trans-isoshinanolone showed interconversion. The current work establishes the chemical basis of the age-old traditional ayurvedic process of detoxification of P. zeylanica.","PeriodicalId":47,"journal":{"name":"Journal of Natural Products ","volume":"88 1","pages":"15–23 15–23"},"PeriodicalIF":3.3,"publicationDate":"2025-01-03","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"143090136","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

Retraction of “Direct Identification of α-Bisabolol Enantiomers in an Essential Oil Using a Combined Ion Mobility–Mass Spectrometry/Quantum Chemistry Approach”

IF 3.3 2区生物学

Journal of Natural Products Pub Date : 2024-12-30 DOI: 10.1021/acs.jnatprod.4c0144410.1021/acs.jnatprod.4c01444

Erik Laurini, Stéphane Andreani, Alain Muselli, Sabrina Pricl and Aura Tintaru*,

引用次数: 0

Neuromodulating Alkaloids from Millipede Defensive Secretions

IF 3.3 2区生物学

Journal of Natural Products Pub Date : 2024-12-30 DOI: 10.1021/acs.jnatprod.4c0116210.1021/acs.jnatprod.4c01162

Carla Menegatti, Jared S. Wood, Paige Banks, Kenneth Knott, Jonathan S. Briganti, Anthony J. Briganti, Samuel V. G. McNally, Paul E. Marek, Anne M. Brown, Tappey H. Jones, R. Thomas Williamson and Emily Mevers*,

{"title":"Neuromodulating Alkaloids from Millipede Defensive Secretions","authors":"Carla Menegatti, Jared S. Wood, Paige Banks, Kenneth Knott, Jonathan S. Briganti, Anthony J. Briganti, Samuel V. G. McNally, Paul E. Marek, Anne M. Brown, Tappey H. Jones, R. Thomas Williamson and Emily Mevers*, ","doi":"10.1021/acs.jnatprod.4c0116210.1021/acs.jnatprod.4c01162","DOIUrl":"https://doi.org/10.1021/acs.jnatprod.4c01162https://doi.org/10.1021/acs.jnatprod.4c01162","url":null,"abstract":"Millipedes have long been known to produce structurally diverse chemical defenses, including hydrogen cyanide, terpenoid alkaloids, and oxidized aromatics. Although the hydrogen cyanide and oxidized aromatic producing millipedes have been well studied, less than 10% of the terpenoid alkaloid producers have been chemically investigated. Several previous studies have shown that alkaloids disorient predators, but their biochemical target is currently unknown. Herein, we investigated the defensive secretions of a colobognath millipede, Ischnocybe plicata, and elucidated the constitution, absolute configuration, and conformation of four new highly oxidized terpenoid alkaloids, termed ischnocybines, using a range of analytical techniques. The ischnocybines are actively secreted from the defensive glands and were shown to disorient ants, a likely common predator. Evaluation of the ischnocybines in a panel of neuroreceptors revealed that ischnocybine A possesses potent (Ki 13.6 nM) and selective (100-fold) binding affinity for sigma-1, an orphan neuroreceptor, over sigma-2. These molecules represent the most complex alkaloids to be discovered from millipedes and provide the first potential insights into a biochemical target responsible for their defensive properties.","PeriodicalId":47,"journal":{"name":"Journal of Natural Products ","volume":"88 1","pages":"110–118 110–118"},"PeriodicalIF":3.3,"publicationDate":"2024-12-30","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"https://pubs.acs.org/doi/epdf/10.1021/acs.jnatprod.4c01162","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"143087007","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

Total Synthesis and Anti-Inflammatory Activity of Tectoridin and Related Isoflavone Glucosides

IF 3.3 2区生物学

Journal of Natural Products Pub Date : 2024-12-28 DOI: 10.1021/acs.jnatprod.4c0110810.1021/acs.jnatprod.4c01108

Hongbo Dong, Yuanwei You, Xiuli Yang, Ling Mei, Yufei Che, Na Wang, Ting Peng and Yujiao He*,

{"title":"Total Synthesis and Anti-Inflammatory Activity of Tectoridin and Related Isoflavone Glucosides","authors":"Hongbo Dong, Yuanwei You, Xiuli Yang, Ling Mei, Yufei Che, Na Wang, Ting Peng and Yujiao He*, ","doi":"10.1021/acs.jnatprod.4c0110810.1021/acs.jnatprod.4c01108","DOIUrl":"https://doi.org/10.1021/acs.jnatprod.4c01108https://doi.org/10.1021/acs.jnatprod.4c01108","url":null,"abstract":"The first total syntheses of four isoflavone glucosides, tectoridin (1), tectoridin A (2), tectorigenin 7-O-β-d-glucopyranosyl-12-O-β-d-glucopyranoside (3), and isotectroigenin 7-O-β-d-glucopyranoside (4), have been accomplished. Key steps in our synthetic approach include a regioselective halogenation reaction, followed by methanolysis to introduce the −OCH3 group into isoflavone frameworks and a PTC-promoted stereoselective glycosidation to establish glycosidic bonds. The synthesized isoflavone glucosides (1–4) and their corresponding aglycones (32 and 34) were evaluated for anti-inflammatory activity against nitric oxide (NO), tumor necrosis factor-α (TNF-α), interleukin-6 (IL-6), and interleukin-1 β (IL-1β) in lipopolysaccharide (LPS)-induced RAW264.7 cells. Aglycones 32 and 34 exhibited stronger anti-inflammatory activity in vitro compared to isoflavone glucosides 1–4.","PeriodicalId":47,"journal":{"name":"Journal of Natural Products ","volume":"88 1","pages":"94–102 94–102"},"PeriodicalIF":3.3,"publicationDate":"2024-12-28","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"143086930","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

Genome Mining of the Marine-Derived Fungus Trichoderma erinaceum F1-1 Unearths Bergamotene-Type Sesquiterpenoids. 海洋真菌毛霉F1-1基因组挖掘发现佛手柑素型倍半萜类。

IF 3.3 2区生物学

Journal of Natural Products Pub Date : 2024-12-27 Epub Date: 2024-12-02 DOI: 10.1021/acs.jnatprod.4c00905

Wencong Yang, Shurong Tian, Yi-Fan Du, Xian-Liang Zeng, Jia-Jing Liang, Wen-Jian Lan, Hang Li

{"title":"Genome Mining of the Marine-Derived Fungus Trichoderma erinaceum F1-1 Unearths Bergamotene-Type Sesquiterpenoids.","authors":"Wencong Yang, Shurong Tian, Yi-Fan Du, Xian-Liang Zeng, Jia-Jing Liang, Wen-Jian Lan, Hang Li","doi":"10.1021/acs.jnatprod.4c00905","DOIUrl":"10.1021/acs.jnatprod.4c00905","url":null,"abstract":"Terpenoids are a vast group of natural products known for their remarkable biological properties and structural diversity. UbiA terpene synthases are increasingly recognized for producing various terpenoids. In this study, we identified a biosynthetic gene cluster (bgt) encoding a UbiA terpene synthase BgtA in the genome of the marine-derived fungus Trichoderma erinaceum F1-1. The gene bgtA was validated to encode the biosynthesis of (-)-α-trans-bergamotene (1). Heterologous expression of the bgt gene cluster in the characterized host Aspergillus nidulans LO8030 activated the biosynthetic pathway, leading to the isolation of eight previously undocumented bergamotene-derived sesquiterpenoids (2-9). Their structures, including the absolute configurations, were elucidated by a combination of spectroscopic analysis, ECD spectra, chemical hydrolysis, single-crystal X-ray diffraction, and biosynthetic considerations. We further demonstrated that the production of these structurally intricate sesquiterpenoids in heterologous expression is attributable to the concerted action of the UbiA terpene synthase BgtA, the cytochrome P450 BgtC, and endogenous enzymes. This study underscores the immense biosynthetic potential of fungal UbiA terpene synthase gene clusters and shows genome mining is a promising strategy for the discovery of novel terpenoids from fungi.","PeriodicalId":47,"journal":{"name":"Journal of Natural Products ","volume":" ","pages":"2746-2756"},"PeriodicalIF":3.3,"publicationDate":"2024-12-27","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"142764808","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