Journal of Natural Products 最新文献_第10页

Development of a Proton Spin Network Fingerprint Library to Support Mass Spectrometry-Based Identification of Pharmacophore-Bearing Constituents in the Botanical Supplement Centella asiatica 建立质子自旋网络指纹文库，支持基于质谱的植物补品积雪草含药团成分鉴定

IF 3.3 2区生物学

Journal of Natural Products Pub Date : 2025-03-28 DOI: 10.1021/acs.jnatprod.4c0148610.1021/acs.jnatprod.4c01486

Sara Neiheisel, Dmitriy Uchenik, Luke Marney, Claudia S. Maier, Nora E. Gray, Amala Soumyanath and Harinantenaina L. Rakotondraibe*,

{"title":"Development of a Proton Spin Network Fingerprint Library to Support Mass Spectrometry-Based Identification of Pharmacophore-Bearing Constituents in the Botanical Supplement Centella asiatica","authors":"Sara Neiheisel, Dmitriy Uchenik, Luke Marney, Claudia S. Maier, Nora E. Gray, Amala Soumyanath and Harinantenaina L. Rakotondraibe*, ","doi":"10.1021/acs.jnatprod.4c0148610.1021/acs.jnatprod.4c01486","DOIUrl":"https://doi.org/10.1021/acs.jnatprod.4c01486https://doi.org/10.1021/acs.jnatprod.4c01486","url":null,"abstract":"Centella asiatica (L.) Urban (Apiaceae) has been utilized for centuries in traditional medicine systems in Southeast Asia and Southern Africa, including Madagascar. Previous studies have reported evidence of the therapeutic potential of C. asiatica formulations in models of Alzheimer’s Disease and other dementias. Caffeoylquinic acids (CQAs) have been identified to be among the pharmacologically relevant metabolites contributing to the botanical’s cognitive enhancement and neuroprotective effects. Isomers of CQAs are, however, difficult to differentiate by commonly used LC-MS techniques, making the characterization, standardization, and batch-to-batch consistency of these formulations challenging. Individual CQAs have unique proton Spin Network Fingerprints (pSNFs) that can be used to distinguish between CQA regioisomers within complex extracts. This work describes the development of a CQA-focused pSNF library that can be used to complement LC-MS methods for the accurate metabolite identification and characterization of bioactive C. asiatica fractions and extracts. The isolation of two new (1 and 2) and four known (3–6) CQAs and CQA analogues from C. asiatica and their contribution to the pSNF library are also discussed herein.","PeriodicalId":47,"journal":{"name":"Journal of Natural Products ","volume":"88 4","pages":"975–984 975–984"},"PeriodicalIF":3.3,"publicationDate":"2025-03-28","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"143867408","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

Isolation and Biosynthesis of Hyellamide, a Glycosylated N-Acyltyrosine Derivative, from the Cyanobacterium Hyella patelloides LEGE 07179. 海蓝藻lege07179糖基化n -酰基酪氨酸衍生物海藻酰胺的分离与生物合成

IF 3.3 2区生物学

Journal of Natural Products Pub Date : 2025-03-28 Epub Date: 2025-02-26 DOI: 10.1021/acs.jnatprod.4c00968

Ângela Brito, Teresa Martins, Sara Freitas, Raquel Castelo Branco, Adriana Rego, Vitor M Vasconcelos, William H Gerwick, Paula Tamagnini, Pedro N Leão

引用次数: 0

Menominin A and B: Cytotoxic Cyclodepsipeptides from the Freshwater Sponge-Associated Cyanobacterium Nostoc sp. UIC 10607. Menominin A和B：来自淡水海绵相关蓝藻的细胞毒性环沉积肽。

IF 3.3 2区生物学

Journal of Natural Products Pub Date : 2025-03-28 Epub Date: 2025-02-20 DOI: 10.1021/acs.jnatprod.4c01445

Lydia J Davis, Aleksej Krunić, Kelsey Alexander, Manead Khin, Jared S Wood, Cody Earp, Manuel Rangel-Grimaldo, Alessandra S Eustáquio, Joanna E Burdette, R Thomas Williamson, Nicholas H Oberlies, Jimmy Orjala

{"title":"Menominin A and B: Cytotoxic Cyclodepsipeptides from the Freshwater Sponge-Associated Cyanobacterium Nostoc sp. UIC 10607.","authors":"Lydia J Davis, Aleksej Krunić, Kelsey Alexander, Manead Khin, Jared S Wood, Cody Earp, Manuel Rangel-Grimaldo, Alessandra S Eustáquio, Joanna E Burdette, R Thomas Williamson, Nicholas H Oberlies, Jimmy Orjala","doi":"10.1021/acs.jnatprod.4c01445","DOIUrl":"10.1021/acs.jnatprod.4c01445","url":null,"abstract":"Menominin A (1) and B (2), two cyclodepsipeptides containing a 3,8-dihydroxy-2-methyltetradecanoic acid residue, were isolated from the freshwater sponge-associated cyanobacterium, Nostoc sp. UIC 10607, using bioactivity-guided and spectroscopic approaches. The planar structures of 1 and 2 were established using HRESIMS and one- and two-dimensional NMR experiments. Comparative genomic analysis revealed unique differences in the putative menominin biosynthetic gene cluster compared to that of the closely related cyanobacterial cyclic lipodepsipeptide, hapalosin, assisting in structure elucidation and highlighting the structural diversity of this class of compounds. Configuration assignments were determined using a combination of J-based configuration analysis, chiral HPLC, modified Mosher's ester analysis, and DFT calculations. Menominin A and B demonstrate antiproliferative bioactivity against the high-grade serous ovarian cancer cell line OVCAR3 (IC50 = 3.1 (1) and 2.4 μM (2)). Menominin A and B are the first reported secondary metabolites from a freshwater sponge-associated cyanobacterium, underscoring the potential of freshwater sponges as a microbial culture source in natural product discovery.","PeriodicalId":47,"journal":{"name":"Journal of Natural Products ","volume":" ","pages":"732-746"},"PeriodicalIF":3.3,"publicationDate":"2025-03-28","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"https://www.ncbi.nlm.nih.gov/pmc/articles/PMC11952978/pdf/","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"143466546","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 Syntheses, Absolute Configuration, and Cytotoxicity Evaluation of Ugonins L, S, U, and Z from the Rhizomes of Helminthostachys zeylanica. 茜草根状茎中乌根素L、S、U和Z的全合成、绝对构型及细胞毒性评价

IF 3.3 2区生物学

Journal of Natural Products Pub Date : 2025-03-28 Epub Date: 2025-03-13 DOI: 10.1021/acs.jnatprod.4c01487

Cheng-Tin Lin, Jing-Jy Cheng, Huei-Ling You, Cheng-Hsun Hsieh, Chiao-Jou Pan, Ming-Jaw Don

引用次数: 0

Phenolics and Phenolic Glycosides from Wrightia pubescens and Their Hepatoprotective Activities. 短毛藤酚类物质和酚苷类物质及其保肝活性。

IF 3.3 2区生物学

Journal of Natural Products Pub Date : 2025-03-28 Epub Date: 2025-02-27 DOI: 10.1021/acs.jnatprod.4c01040

Xingxiang Chen, Ping Yi, Hang Lv, Mimi Zhang, Junwei Yang, Zengguang Zhang, Zhilong Zhao, Yu Mu, Li Han, Xueshi Huang

{"title":"Phenolics and Phenolic Glycosides from Wrightia pubescens and Their Hepatoprotective Activities.","authors":"Xingxiang Chen, Ping Yi, Hang Lv, Mimi Zhang, Junwei Yang, Zengguang Zhang, Zhilong Zhao, Yu Mu, Li Han, Xueshi Huang","doi":"10.1021/acs.jnatprod.4c01040","DOIUrl":"10.1021/acs.jnatprod.4c01040","url":null,"abstract":"Thirty compounds including 13 new phenolic glycosides (1-6, 9-15) and 17 known aromatic compounds and aromatic glycosides (7-8, 16-30) were isolated from the roots of Wrightia pubescens. The structures of the new phenolic glycosides were established by extensive NMR spectroscopic data analysis as well as chemical derivatization method. The isolated compounds were evaluated for their hepatoprotective activities using cell model of acetaminophen (APAP)-induced HepG2 cells. The results indicated that phenolic glycosides (2, 4, 5, 7, 8, 11, 13) pretreatment enhanced the cells viability and reduced the levels of aspartate aminotransferase (AST), alanine aminotransferase (ALT). The hepatoprotective mechanism of a representative new compound, wrightioside D (4), was further investigated. Compound 4 exhibited hepatoprotective effects via reducing oxidative stress by attenuating ROS formation and inhibiting apoptosis in APAP-treated HepG2 cells.","PeriodicalId":47,"journal":{"name":"Journal of Natural Products ","volume":" ","pages":"631-643"},"PeriodicalIF":3.3,"publicationDate":"2025-03-28","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"143514094","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

laeA Gene Introduction Strategy Enabling the Construction of a Prolific Fungal Secondary Metabolite Library. laeA基因导入策略构建高产真菌次生代谢物文库。

IF 3.3 2区生物学

Journal of Natural Products Pub Date : 2025-03-28 Epub Date: 2025-02-20 DOI: 10.1021/acs.jnatprod.4c01317

Aoi Kimishima, Sota Honma, Satoshi Kato, Masako Honsho, Hiroki Kojima, Toshiyuki Tokiwa, Akihiro Sugawara, Kenichi Nonaka, Yasuko Araki, Tadashi Takahashi, Kotaro Ito, Yukihiro Asami

{"title":"laeA Gene Introduction Strategy Enabling the Construction of a Prolific Fungal Secondary Metabolite Library.","authors":"Aoi Kimishima, Sota Honma, Satoshi Kato, Masako Honsho, Hiroki Kojima, Toshiyuki Tokiwa, Akihiro Sugawara, Kenichi Nonaka, Yasuko Araki, Tadashi Takahashi, Kotaro Ito, Yukihiro Asami","doi":"10.1021/acs.jnatprod.4c01317","DOIUrl":"10.1021/acs.jnatprod.4c01317","url":null,"abstract":"LaeA is a putative nuclear methyltransferase protein that epigenetically influences secondary metabolite production in fungi. LaeA has drawn attention as one of the promising approaches to activate fungal chemical production, and the laeA gene has been introduced into some fungal strains with the aim of producing secondary metabolic changes mainly based on the evaluation of mycotoxicity. However, these studies were applied for limited fungal species, and its utility and versatility for broad fungal species remained unclear. In this study, 47 strains were selected composed of three different genera, Pochonia spp., Gamszarea kalimantanensis, and Lecanicillium spp., which have never been modified with the laeA gene. We obtained a total of 125 mutants with laeA genes for our fungal strain library. The chemical productivity and the biological activity of the library were analyzed, and two natural products, radicicol (1) and sch210972 (2), were isolated in more than 10-fold the yield of the parent strains.","PeriodicalId":47,"journal":{"name":"Journal of Natural Products ","volume":" ","pages":"682-687"},"PeriodicalIF":3.3,"publicationDate":"2025-03-28","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"143456241","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

(±)-Feionemycin A and Chromonemycins A-D, Rearranged Aromatic Polyketides Uncovered by Type II Polyketide Gene Cluster Expression. （±）-Feionemycin A和chromonemycin A- d，ⅱ型聚酮基因簇表达揭示的重排芳香聚酮。

IF 3.3 2区生物学

Journal of Natural Products Pub Date : 2025-03-28 Epub Date: 2025-02-27 DOI: 10.1021/acs.jnatprod.4c01433

Xiaofei Huang, Xiao Xu, Luning Zhou, Jiayi Li, Chuanteng Ma, Wenxue Wang, Qian Che, Dehai Li, Tianjiao Zhu, Guojian Zhang

引用次数: 0

Chromene Dimers from Cultures of Basidiomycete Panus similis. 相似担子菌培养物中铬二聚体的研究。

IF 3.3 2区生物学

Journal of Natural Products Pub Date : 2025-03-28 Epub Date: 2025-02-26 DOI: 10.1021/acs.jnatprod.4c01475

Somporn Palasarn, Prattana Tanyapanyachon, Vanicha Vichai, Phongeun Sysouphanthong, Kevin D Hyde, Nattika Saengkrit, Masahiko Isaka

{"title":"Chromene Dimers from Cultures of Basidiomycete Panus similis.","authors":"Somporn Palasarn, Prattana Tanyapanyachon, Vanicha Vichai, Phongeun Sysouphanthong, Kevin D Hyde, Nattika Saengkrit, Masahiko Isaka","doi":"10.1021/acs.jnatprod.4c01475","DOIUrl":"10.1021/acs.jnatprod.4c01475","url":null,"abstract":"Four chromene dimers, panusimilins A-D (1-4) (racemic mixtures), and two previously undescribed chromanes (5a/5b and 6a/6b) were isolated from cultures of basidiomycete Panus similis TBRC-BCC 52578. Interestingly, synthetic compounds closely related to panusimilins A-C (1-3) were previously reported, which were produced by Lewis acid promoted dimerization of a plant-derived chromene, precocene II. In the present study, panusimilins were isolated from the culture broth extract of the fungus P. similis. The chromane monomers were shown to be a non-racemic mixture of enantiomers, and their absolute configurations were elucidated by conversion to Mosher ester derivatives. The isolated compounds were evaluated for their cytotoxic activities. Among them, 2,2-dimethyl-3,4,6-trihydroxychromane (6a/6b) showed selective activity to NCI-H187 cells (IC50 9.1 μM). On the other hand, panusimilin B (2) exhibited antioxidant activity in the DPPH radical scavenging assay (IC50 66 μM).","PeriodicalId":47,"journal":{"name":"Journal of Natural Products ","volume":" ","pages":"777-784"},"PeriodicalIF":3.3,"publicationDate":"2025-03-28","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"143514074","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

Efficient and Selective Biosynthesis of a Precursor-Directed FK506 Analogue: Paving the Way for Click Chemistry. 前体导向FK506类似物的高效和选择性生物合成：为点击化学铺平道路。

IF 3.3 2区生物学

Journal of Natural Products Pub Date : 2025-03-28 Epub Date: 2025-03-10 DOI: 10.1021/acs.jnatprod.4c00394

Dušan Goranovič, Branko Jenko, Barbara Ramšak, Ajda Podgoršek Berke, Leon Bedrač, Jaka Horvat, Martin Šala, Damjan Makuc, Guilhermina M Carriche, Luana Silva, Aleksandra Lopez Krol, Alen Pšeničnik, María Beatriz Durán Alonso, Martina Avbelj, Stojan Stavber, Janez Plavec, Tim Sparwasser, Rolf Müller, Gregor Kosec, Štefan Fujs, Hrvoje Petković

{"title":"Efficient and Selective Biosynthesis of a Precursor-Directed FK506 Analogue: Paving the Way for Click Chemistry.","authors":"Dušan Goranovič, Branko Jenko, Barbara Ramšak, Ajda Podgoršek Berke, Leon Bedrač, Jaka Horvat, Martin Šala, Damjan Makuc, Guilhermina M Carriche, Luana Silva, Aleksandra Lopez Krol, Alen Pšeničnik, María Beatriz Durán Alonso, Martina Avbelj, Stojan Stavber, Janez Plavec, Tim Sparwasser, Rolf Müller, Gregor Kosec, Štefan Fujs, Hrvoje Petković","doi":"10.1021/acs.jnatprod.4c00394","DOIUrl":"10.1021/acs.jnatprod.4c00394","url":null,"abstract":"The medically important immunosuppressant FK506 is a structurally complex macrolactone biosynthesized by a combined polyketide synthase and a nonribosomal peptide synthetase enzyme complex. Its acyltransferase domain 4 (AT4) selects an unusual extender unit, resulting in an allyl moiety on carbon 21 of the macrolactone backbone. Based on the AT4 domain, chemobiosynthetic processes have been developed that enable the introduction of diverse moieties at the carbon 21 position. However, the novel moieties that were introduced into the polyketide backbone are chemically inert. Reported here is a novel and efficient chemobiosynthetic approach that ensures high titer of an FK506 analogue containing a propargyl moiety. The novel FK506 analogue displays lower immunosuppression activity than FK506 with significantly reduced cytotoxicity. More importantly, the propargyl moiety contains a terminal alkyl group, which makes click chemistry reactions possible; this approach may potentially be translated to other medically important drugs of polyketide origin.","PeriodicalId":47,"journal":{"name":"Journal of Natural Products ","volume":" ","pages":"619-630"},"PeriodicalIF":3.3,"publicationDate":"2025-03-28","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"https://www.ncbi.nlm.nih.gov/pmc/articles/PMC11959593/pdf/","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"143583945","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

Additional Bioactive Silvestrol Analogs from the Roots of Aglaia perviridis Collected in Vietnam. 越南产细叶菖蒲根中活性西尔维斯特罗类似物的研究。

IF 3.3 2区生物学

Journal of Natural Products Pub Date : 2025-03-28 Epub Date: 2025-03-04 DOI: 10.1021/acs.jnatprod.4c01247

Ermias Mekuria Addo, Daniel Adu-Ampratwum, Elizabeth N Kaweesa, Garima Agarwal, Dmitriy Uchenik, Tran N Ninh, Djaja D Soejarto, Joanna E Burdette, James R Fuchs, A Douglas Kinghorn, Harinantenaina L Rakotondraibe

{"title":"Additional Bioactive Silvestrol Analogs from the Roots of Aglaia perviridis Collected in Vietnam.","authors":"Ermias Mekuria Addo, Daniel Adu-Ampratwum, Elizabeth N Kaweesa, Garima Agarwal, Dmitriy Uchenik, Tran N Ninh, Djaja D Soejarto, Joanna E Burdette, James R Fuchs, A Douglas Kinghorn, Harinantenaina L Rakotondraibe","doi":"10.1021/acs.jnatprod.4c01247","DOIUrl":"10.1021/acs.jnatprod.4c01247","url":null,"abstract":"The tropical plant Aglaia perviridis is known to produce cyclopenta[b]benzofuran and other types of rocaglate derivatives including silvestrol (3) and 5‴-episilvestrol (4) that are of current pharmacological interest. In the present work, further investigation of A. perviridis roots collected in Vietnam has yielded two new rocaglate acetonide derivatives (1 and 2) and a known pentanor-3,4-seco-dammarane triterpenoid (7) found for the first time as a natural product, in addition to four known rocaglates (3-6). The structures of compounds 1 and 2 were confirmed by partial synthesis experiments, and their potential occurrence as extraction artifacts was investigated by targeted selective ion monitoring using UHPLC-MS. All compounds obtained were evaluated against a panel of four human cancer cell lines, in which the six rocaglate derivatives (1-6) tested all showed submicromolar potencies.","PeriodicalId":47,"journal":{"name":"Journal of Natural Products ","volume":" ","pages":"662-670"},"PeriodicalIF":3.3,"publicationDate":"2025-03-28","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"https://www.ncbi.nlm.nih.gov/pmc/articles/PMC11960728/pdf/","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"143555348","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