Article
Plant Sciences
Marcelo R. de Amorim, Tiago A. Paz, Luciano da S. Pinto, Felipe Hilario, Camila L. Zanini, Anna Caroline C. Aguiar, Debora E. S. Silva, Maysa Furlan, Rafael V. C. Guido, Tais M. Bauab, Adelino V. de G. Netto, Lourdes C. dos Santos
Summary: In this study, four new alkaloids and four known compounds were isolated from the extract of Paraphaeosphaeria sporulosa F03 strain. The new compounds showed antifungal activity against Candida species and one of them exhibited antiplasmodial activity.
Article
Chemistry, Medicinal
Felipe Hilario, Giulia Polinario, Marcelo Rodrigues de Amorim, Weslei Bruno Botero, Talita Peixoto, Tiago Antunes Paz, Maysa Furlan, Andrea Nastri de Luca Batista, Joao Marcos Batista Jr, Tafs Maria Bauab, Lourdes Campaner dos Santos
Summary: This study investigates the effects of chemical elicitors and epigenetic modifiers on the production and diversification of secondary metabolites in an endophytic fungus. The addition of Cu+2 to the culture medium has the most significant impact on the metabolic profile of the fungus and results in the isolation of seven active compounds. These compounds exhibit relevant antifungal activity against Candida spp.
Article
Biochemistry & Molecular Biology
Qiong Chen, Jun-Jie Yu, Juan He, Tao Feng, Ji-Kai Liu
Summary: This study found that small polyketide metabolites produced by the kiwi endophytic fungus Paraphaeosphaeria sporulosa have anti-Psa activity, which may provide protection to host plants. This finding is significant for the development of the kiwifruit industry.
Article
Microbiology
Viridiana Morales-Sanchez, Carmen E. Diaz, Elena Trujillo, Sonia A. Olmeda, Felix Valcarcel, Ruben Munoz, Maria Fe Andres, Azucena Gonzalez-Coloma
Summary: The ethyl acetate extract from the endophytic fungus Aspergillus sp. SPH2 showed potential biocontrol properties against various plant pathogens, insect pests, and plant parasites. Compound 1, mellein, demonstrated strong ixodicidal effects, while compound 2, neoaspergillic acid, exhibited potent antifungal effects. The study also suggested that compound 2 may be the biosynthetic precursor of compound 3, neohydroxyaspergillic acid.
Article
Plant Sciences
Caroline O. Andrino, Paulo T. Sano, Peter W. Inglis, Nancy Hensold, Fabiane N. Costa, Marcelo F. Simon
Summary: Paepalanthus is a diverse monocot genus with remarkable diversity distributed in the Neotropical highlands of South America, consisting of 410 species with considerable morphological heterogeneity. The study found that Paepalanthus and 16 of its 28 infrageneric categories are not monophyletic, as well as the closely related genus Actinocephalus.
BOTANICAL JOURNAL OF THE LINNEAN SOCIETY
(2021)
Article
Biochemistry & Molecular Biology
Amjad Ayad Qatran Al-Khdhairawi, Jason Siau Ee Loo, Nurliana Abd Mutalib, Normala Abd Latip, Nurhuda Manshoor, Hamidah Abu Bakar, Narendra Babu Shivanagere Nagojappa, Jean-Frederic Weber
Summary: Four previously undescribed alkaloids and four known diterpene pyrones were isolated from the culture of Aspergillus sp. HAB10R12. The chemical structures of the compounds were determined using NMR and MS analysis. The absolute configurations of the compounds were determined through Electronic Circular Dichroism analysis and computational methods. The alkaloids showed no antiproliferative activity against HepG2 and A549 cancer cell lines.
Article
Plant Sciences
Lucas Espindola Florencio Da Silva, Marcelo Trovo
Summary: The study critically evaluates the description, type specimens, and morphology of Paepalanthus decorus, proposing its synonymization under P. flaccidus based on the findings. Detailed comparison of the two species is provided, along with a designated lectotype for P. flaccidus.
Article
Biochemistry & Molecular Biology
Dandan Zhang, Xiaoqing Wang, Bo Liu, Shuhui Li, Yanlei Wang, Tao Guo, Yi Sun, Riccardo Petrelli
Summary: Two new dipyrroloquinones and four known secondary metabolites were isolated and identified from a fungus using mass spectrometry-based metabolic profiling and a bioassay-guided method. Some of these compounds exhibited anti-inflammatory and antitumor activities.
Article
Plant Sciences
Yan Chen, Huan Wang, Xin Ke, Zihuan Sang, Min Kuang, Weiwei Peng, Jianbing Tan, Yuting Zheng, Zhenxing Zou, Haibo Tan
Summary: Two previously undescribed lactones and three new sesquiterpenoids were isolated from the fungus Phomopsis sp. SZSJ-7B. Their chemical structures were determined by various analytical techniques, and one of the lactones showed significant antibacterial activity against methicillin-resistant Staphylococcus aureus.
FRONTIERS IN PLANT SCIENCE
(2022)
Article
Chemistry, Organic
Wen-Yu Zu, Jian-Wei Tang, Kun Hu, Yuan-Fei Zhou, Lei-Lei Gou, Xiao-Zheng Su, Xinxiang Lei, Han-Dong Sun, Pema-Tenzin Puno
Summary: Three novel compounds were isolated from an endophytic fungus, including Chaetolactam A with a unique structure and 11-epi-chaetomugilide B exhibiting potent apoptosis induction activity.
JOURNAL OF ORGANIC CHEMISTRY
(2021)
Article
Chemistry, Medicinal
Mengyi Deng, Xia Chen, Zhengyi Shi, Shuangshuang Xie, Yuben Qiao, Gang Chen, Xiaosheng Tan, Yuanyuan Lu, Changxing Qi, Yonghui Zhang
Summary: Six new metabolites were isolated from an endophytic fungus Aspergillus sp., with compound 2 being the first example of a diphenolic derivative with an unusual structure, and compound 3 being the first example of a pseurotin type natural product with only one hydroxy group substituted on the side chain. Compounds 3, 7, and 8 exhibited inhibitory effects on murine T cell proliferation induced by anti-CD3/anti-CD28 monoclonal antibodies.
Article
Chemistry, Medicinal
Jin Yang, Lizhi Gong, Miaomiao Guo, Yu Jiang, Yi Ding, Zhijie Wang, Xiujuan Xin, Faliang An
Summary: Six new prenylated indole diketopiperazine alkaloids, along with eight known analogues, were isolated from the marine-derived endophytic fungus Aspergillus sp. YJ191021. Compound 1 exhibited moderate antifungal, antibacterial, and anti-inflammatory activities, indicating its potential as a bioactive compound.
Article
Chemistry, Applied
Hong-Mei Lei, Ni Ma, Ting Wang, Pei-Ji Zhao
Summary: Endophytic fungus Colletotrichum sp. F168 was isolated from Huperzia serrata plant and subjected to phytochemical investigation, resulting in the discovery of nine compounds, including two new structures. However, the two new compounds did not exhibit acetylcholinesterase inhibitory activity.
NATURAL PRODUCT RESEARCH
(2021)
Article
Biochemistry & Molecular Biology
Jintong Song, Ke Xu, Chunyu Liu, Tian Wang, Xiaoyi Luan, Lihua Zhu, Zhaojun Chu, Xiaojie Fu, Wenqiang Chang, Xiaoning Wang, Hongxiang Lou
Summary: Fourteen undescribed compounds, including five 2,5-diarylcyclopentenones xylariaones A1-B2, seven a-pyrone derivatives xylaripyones A G, one.-pyrone derivative xylaripyone H, one diketopiperazine cyclo-(L-Leu-N=ethyl-L-Glu), and two known diketopiperazines, were isolated from cultures of the endophytic fungus Xylaria sp., which was separated from Cudrania tricuspidata Bureau ex Lavall ' ee. Their structures were determined by analysing extensive spectroscopic data (HRESIMS and NMR) and electronic circular dichroism (ECD) calculations. Furthermore, these compounds were evaluated for potential antiproliferative activity against the human tumour cell lines PC3 and A549, and the results showed that xylaripyone D exhibited moderate inhibitory activity against the proliferation of PC3 cell lines with an IC50 value of 14.75 μM. Meanwhile, xylariaone A3 and xylaripyone F displayed weak inhibitory effects on NO production in RAW 264.7 murine macrophages with IC50 values of 49.76 and 69.68 μM, respectively.
Article
Biotechnology & Applied Microbiology
Carollayne Goncalves-Magalhaes, Tamara Prado de Morais, Denise Garcia de Santana, Simone Abreu Asmar, Joao Paulo Ribeiro-Oliveira, Jose Magno Queiroz Luz
Summary: This study is the first report on in vitro propagation of Paepalanthus chiquitensis Herzog, providing a cultivation protocol and demonstrating the positive effects of plant growth regulators on its growth.
PLANT CELL TISSUE AND ORGAN CULTURE
(2023)
Review
Microbiology
Bruna Almeida Furquim de Camargo, Bruno Fonseca-Santos, Suzana Goncalves Carvalho, Gabriela Correa Carvalho, Leonardo Delello Di Filippo, Victor Hugo Sousa Araujo, Jonatas Lobato Duarte, Amanda Leticia Polli Silvestre, Tais Maria Bauab, Marlus Chorilli
Summary: Infectious diseases remain a public health problem, and nanotechnology offers new solutions. Lipid-based drug delivery nanosystems have many advantages and can be used to treat infectious diseases caused by viruses, bacteria, fungi, and parasites.
CRITICAL REVIEWS IN MICROBIOLOGY
(2023)
Review
Chemistry, Medicinal
Gabriel Davi Marena, Matheus Aparecido dos Santos Ramos, Gabriela Correa Carvalho, Jose Alberto Paris Junior, Flavia Aparecida Resende, Ione Correa, Gabriela Yuki Bressanim Ono, Victor Hugo Sousa Araujo, Bruna Almeida Furquim de Camargo, Tais Maria Bauab, Marlus Chorilli
Summary: Fungal infections pose a significant public health issue, particularly for immunocompromised individuals, nosocomial settings, patients with chronic diseases, and transplant recipients. Natural products show promise in developing new antifungal drugs, and pharmaceutical nanotechnology can enhance their delivery and clinical efficacy.
PHYTOTHERAPY RESEARCH
(2022)
Article
Chemistry, Medicinal
Jackson Monteiro, Luiz Felipe D. Passero, Jessica A. Jesus, Marcia D. Laurenti, Joao H. G. Lago, Marisi G. Soares, Andrea N. L. Batista, Joao M. Batista Jr, Patricia Sartorelli
Summary: This study isolated and characterized the sesquiterpene (-)-cyclocolorenone from Duguetia lanceolata leaves, and evaluated its antileishmanial activity. Results showed that (-)-cyclocolorenone exhibited inhibitory effects against Leishmania (Leishmania) amazonensis and had low toxicity.
CURRENT TOPICS IN MEDICINAL CHEMISTRY
(2022)
Article
Chemistry, Applied
Tomaz Henrique Duarte Chorro, Edson Leonardo Scarpa de Souza, Otto Daolio Koster, Ellen Christine Polo, Rafaela Costa Carmona, Vitor Hugo Menezes da Silva, Joao Marcos Batista Junior, Carlos Roque Duarte Correia
Summary: A new enantioselective intramolecular strategy for the synthesis of enantioenriched bridged benzoxacines, unsaturated spirobenzofurans, 2,3-dihydrobenzofuran, and 2,3-indoline acetate scaffolds directly from anilines has been developed. The process combines in situ diazotization of the aniline with intramolecular Heck-Matsuda reaction, eliminating the need for isolation and purification of potentially unstable or hard-to-synthesize aryldiazonium salts. The method has been demonstrated to be practical and robust, achieving high yields and enantiomeric ratios.
ADVANCED SYNTHESIS & CATALYSIS
(2023)
Review
Chemistry, Multidisciplinary
Thayssa S. F. Fagundes, Thatyana R. A. Vasconcelos, Fernando M. dos Santos Jr, Bia F. Rajsfus, Diego Allonso, Jose C. J. M. D. S. Menezes, Alessandra L. Valverde, Vinicius R. Campos
Summary: Arthropod-borne viruses (arboviruses) are a significant global public health problem, causing hundreds of millions of infections and thousands of deaths each year. However, there are currently no prophylactic or pharmacological therapies available for most arboviruses. Therefore, there is an urgent need to search for new strategies to prevent arbovirus infections. Marine organisms, with their unique secondary metabolism, offer potential as a source of structurally novel compounds with antiviral and larvicidal activities.
JOURNAL OF THE BRAZILIAN CHEMICAL SOCIETY
(2023)
Article
Infectious Diseases
Gabriel Davi Marena, Gabriela Correa Carvalho, Matheus Aparecido dos Santos Ramos, Marlus Chorilli, Tais Maria Bauab
Summary: Nanoemulsions containing micafungin were developed to improve its action against Candida auris infections, which are becoming increasingly resistant. The nanoemulsions showed good stability and exhibited action against biofilms and in the in vivo infection model. Further studies should be carried out to evaluate their efficacy in mice.
Article
Chemistry, Physical
Carson Wiethan, Ingredy B. Braga, Vitor H. Menezes da Silva, Joao M. Batista Jr, Carlos Roque D. Correia
Summary: The enantioselective synthesis of isoindolones via Heck-Mizoroki reactions of endocyclic enamides using a palladium-bis(oxazoline) catalyst system is described. N,N-ligands prove to be an effective and low-cost alternative to phosphine-based chiral ligand counterparts. The intramolecular Heck reaction enables the construction of tricyclic isoindolones containing chiral centers in high yields and enantiomeric ratios.
Article
Immunology
Alexander Batista-Duharte, Damiana Tellez-Martinez, Deivys Leandro Portuondo, Iracilda Zeppone Carlos
Summary: This study evaluated the impact of regulatory T cell (Treg) depletion on the immunogenicity of an anti-Sporothrix vaccine. The results showed that Treg depletion enhanced the production of specific Th1 lymphocytes and cytokines, and also improved the reduction of fungal load. These findings suggest that Treg depletion may improve the efficacy of vaccination against Sporothrix.
FRONTIERS IN CELLULAR AND INFECTION MICROBIOLOGY
(2023)
Article
Chemistry, Organic
Valdeir C. de Oliveira, Ricardo A. Angnes, Joao M. Batista Jr, Carlos Roque D. Correia
Summary: This work presents an effective method for the synthesis of chiral vinyl cyclopentenols via Heck desymmetrization of cyclopent-3-en-1-ylmethanol using vinyl triflates as coupling agents and chiral N,N ligands. The reaction exhibited high enantioselectivity and diastereoselectivity, with isolated yields of up to 80% and enantiomeric ratios of up to 97:3. The diastereoselectivities were rationalized through experiments using different vinyl triflates and the desymmetrization of a protected olefin substrate.
EUROPEAN JOURNAL OF ORGANIC CHEMISTRY
(2023)
Article
Chemistry, Physical
Joao M. Batista, Valentin Paul Nicu
Summary: Cyclic peptides are important structures in medicinal chemistry, but studying their solution-state structure is challenging. Vibrational circular dichroism (VCD) spectroscopy is a valuable alternative to NMR, but the calculations involved are difficult. In this study, we present a genetic algorithm-guided VCD approach that is simple, more effective, and provides higher resolution of conformers.
PHYSICAL CHEMISTRY CHEMICAL PHYSICS
(2023)
Article
Chemistry, Organic
Karine N. N. de Andrade, Lucas H. H. Martorano, Guilherme S. S. Correa, Fernando M. M. dos Santos Jr, Jose Walkimar de M. Carneiro, Ana Carolina F. de Albuquerque, Anne Caroline C. Gomes, Rodolfo G. G. Fiorot
Summary: C-Glycosyl-flavonoids are natural products with diverse biological applications, exhibiting rotational isomerism. The reasons for this phenomenon, which is characterized by NMR signal duplication, remain unclear. In this study, a DFT investigation was conducted to elucidate the origins of rotational isomerism in a set of C-glycosyl-flavonoids. The results revealed that the rotation around the sugar-aglycone bond at the 8-C position of the flavonoid backbone has the highest energetic barrier. By simulating solvent molecules explicitly, it was found that flavonoid-solvent interactions play a crucial role in NMR signal duplication.
ORGANIC CHEMISTRY FRONTIERS
(2023)
Article
Chemistry, Multidisciplinary
Andrea N. L. Batista, Lucas H. Martorano, Alessandra L. Valverde, Fernando M. dos Santos Jr
Summary: Nuclear magnetic resonance (NMR) spectroscopy provides detailed information about a molecule's chemical structure and stereochemistry. However, it may not always be sufficient to confidently assign the relative configuration of a secondary metabolite. Additional experiments, such as Density Functional Theory (DFT) calculations of chemical shifts, may be necessary to support the assignment. Here, we present the structure analysis of a natural endoperoxide (1) from Plakortis angulospiculatus using quantum NMR calculations for the first time.
NEW JOURNAL OF CHEMISTRY
(2023)
Article
Chemistry, Physical
Tom Vermeyen, Andrea N. L. Batista, Alessandra L. Valverde, Wouter Herrebout, Joao M. Batista Jr
Summary: Vibrational circular dichroism (VCD) is a powerful technique for assessing the stereochemistry of chiral molecules. The need for quantum chemical calculations has limited its use by non-experts. In this study, we propose a method using visual inspection and machine learning to search for and validate IR and VCD spectral markers, allowing for absolute configuration assignments in complex mixtures without DFT calculations. Monoterpene mixtures are used as a proof-of-concept.
PHYSICAL CHEMISTRY CHEMICAL PHYSICS
(2023)
Article
Chemistry, Medicinal
Felipe Hilario, Giulia Polinario, Marcelo Rodrigues de Amorim, Weslei Bruno Botero, Talita Peixoto, Tiago Antunes Paz, Maysa Furlan, Andrea Nastri de Luca Batista, Joao Marcos Batista Jr, Tafs Maria Bauab, Lourdes Campaner dos Santos
Summary: This study investigates the effects of chemical elicitors and epigenetic modifiers on the production and diversification of secondary metabolites in an endophytic fungus. The addition of Cu+2 to the culture medium has the most significant impact on the metabolic profile of the fungus and results in the isolation of seven active compounds. These compounds exhibit relevant antifungal activity against Candida spp.
Article
Spectroscopy
Andrea N. L. Batista, Carlos Henrique T. Santos, Ana Carolina F. de Albuquerque, Fernando M. Santos Jr, Fernanda R. Garcez, Joao M. Batista Jr
Summary: The determination of the absolute configuration of natural products is a challenging task due to the complexity of the molecules produced by nature. Current methods rely on the comparison of optical rotation and/or electronic circular dichroism data, which may lead to misassignments and error propagations. This study presents the use of VCD spectroscopy as a more reliable and sensitive technique for investigating the stereochemistry of bicyclo(3.2.1)octane neolignans.
SPECTROCHIMICA ACTA PART A-MOLECULAR AND BIOMOLECULAR SPECTROSCOPY
(2024)
