Vanderlan Bolzani

Vanderlan Bolzani
São Paulo State University | Unesp · Department of Chemistry

Professor

About

79
Publications
8,019
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626
Citations
Citations since 2016
69 Research Items
580 Citations
2016201720182019202020212022050100150
2016201720182019202020212022050100150
2016201720182019202020212022050100150
2016201720182019202020212022050100150

Publications

Publications (79)
Article
Full-text available
Investigating the chemical diversity of natural products from tropical environments is an inspiring approach to developing new drug candidates for neglected tropical diseases (NTDs). In the present study, phenotypic screenings for antiprotozoal activity and a combination of computational and biological approaches enabled the identification and char...
Article
Cyclotides are mini-proteins with potent bioactivities and outstanding potential for agricultural and pharmaceutical applications. More than 450 different plant cyclotides have been isolated from six angiosperm families. In Brazil, studies involving this class of natural products are still scarce, despite its rich floral biodiversity. Herein were i...
Article
Full-text available
In Brazil, research with natural products had a strong impulse when FAPESP supported the creation of the Laboratory of Chemistry of Natural Products of the Institute of Chemistry of USP (1966). In 1999, FAPESP launched the Research Program in the Characterization, Conservation, Restoration and Sustainable Use of Biodiversity (BIOTA-FAPESP), which i...
Article
Background: Chikungunya fever is an endemic disease caused by the Chikungunya virus (CHIKV). To date there is no antiviral treatment against this infection or licensed vaccine to prevent it. Our study aims to evaluate whether (-)-cassine (1) and (-)-spectaline (2), the main alkaloids of Senna spectabilis, display anti-CHIKV activity. Both compound...
Article
To design a green chemistry future, the development of new protocols for standardization of phytomedicines should consider both traditional and environmental parameters. In the present study, we developed a new natural deep eutectic solvent (NADES)-based microwave-assisted extraction (MAE) of phenolics from leaves of Eugenia uniflora L. This specie...
Article
Eight phenolic compounds were isolated from Eugenia pyriformis leaves fraction by semi-preparative HPLC and characterized by Nuclear Magnetic Resonance (NMR) and mass spectrometry (ESI-MS). Five compounds were isolated and identified for the first time in E. pyriformis species, while this is the first report of the accumulation of isoquercitrin, qu...
Article
Full-text available
We report the major conclusions of the online open-access workshop "Computational Applications in Secondary Metabolite Discovery (CAiSMD)" that took place from 08 to 10 March 2021. Invited speakers from academia and industry and about 200 registered participants from five continents (Africa, Asia, Europe, South America, and North America) took part...
Article
Exploratory factor analysis was applied to determine the chemical differences between fruitbodies of three Agaricus subrufescens mushroom strains [from Japan (JP), Brazil (ABZ), and Belgium (T2)] grown with handmade and commercial supplements. The composition of the ABZ strain cultivated with agro-industrial waste supplement presented a high nutrit...
Article
In this work, we developed a green HPLC-PAD method to fingerprint Eugenia uniflora L. leaves by employing Design of Experiments with inexpensive food grade bioethanol as mobile-phase organic modifier aiming to cover Green Analytical Chemistry (GAC) principles and concepts. Initially, two different chromatographic columns coupled with five chromatog...
Article
In the present study, a series of chalcones and their B-aryl analogues were prepared and evaluate as inhibitors of myeloperoxidase (MPO) chlorinating activity, using in vitro and ex vivo assays. Among these, B-thiophenyl chalcone (analogue 9) demonstrated inhibition of in vitro and ex vivo MPO chlorinating activity, exhibiting IC50 value of 0.53 an...
Article
Natural products are a valuable source of biologically active compounds and continue to play an important role in modern drug discovery due to their great structural diversity and unique biological properties. Brazilian biodiversity is one of the most extensive in the world and could be an effective source of new chemical entities for drug discover...
Article
From an environmental perspective, searching for useful compounds in agri-food by-products by employing inefficient and polluting analytical procedures is paradoxical. This work aimed to develop a green, simplified, and highly efficient experimental setup for extracting and tentatively identifying the broadest range of metabolites in sugarcane soli...
Article
Three new oxygenated cyclohexanoids, namely, speciosin U (1), speciosin V (2) and speciosin W (3), along with four known compounds consisting of 4-hydroxy-3-(3′-methylbut-3′-en-1′-ynyl)-benzoic acid (4), 4-hydroxy-3-prenyl-benzoic acid (5), 2,2-dimethyl-2H-chromene-6-carboxylic acid (6) and trans-3,4-dihydro-3,4-dihydroxy-anofinic acid (7) were iso...
Article
The thermal behavior of two commercially available sweeteners based on Stevia rebaudiana Bertoni was studied by TG–DSC and EGA. The composition prior and after heating was analyzed by LC–MS/MS to identify the steviol glycosides present in each formulation and thermal degradation products, respectively. The two formulations (S1 and S2) presented the...
Article
Niedenzuella multiglandulosa (Malpighiaceae) is a neotropical liana responsible for cattle intoxication outbreaks in Brazil that may lead to abortion and even death of the animals, causing substantial losses in Brazilian trade balance. A phytochemical study of N. multiglandulosa leaves was performed in order to obtain chemical information about sec...
Article
Full-text available
In this study, the chemical composition, total phenolic content, and antioxidant activity (DPPH, ORAC and FRAP assays) of A. subrufescens and P. ostreatus, cultivated with handmade and commercials supplements, were compared. Additionally, the compounds ergosterol, saccharopine, and hexitol were identified in A. subrufescens by HPLC‐MS/MS. The antio...
Article
Introduction Crotalaria spectabilis is an important species used as a pre‐plant cover for soybean crops to control the proliferation of endoparasitic nematodes. Species from the Crotalaria genus are known for presenting pyrrolizidine alkaloids (PAs) in their composition, however, C. spectabilis is still considered chemically under‐explored. Object...
Article
Two new polyketides, named koninginin T (1) and U (2), were isolated from Phomopsis stipata - an endophytic fungus isolated from Styrax camporum Pohl. The structures of polyketides 1 and 2 were defined through the analysis of spectroscopic data. Antifungal and acetylcholinesterase inhibitory activities of these compounds were evaluated using TLC bi...
Chapter
Databases play an important role in various computational techniques, including virtual screening (VS) and molecular modeling in general. These collections of molecules can contain a large amount of information, making them suitable for several drug discovery applications. For example, vendor, bioactivity data or target type can be found when searc...
Chapter
Technological advances have contributed to the evolution of the natural product chemistry and drug discovery programs. Recently, computational methods for nuclear magnetic resonance (NMR) and mass spectrometry (MS) have speeded up and facilitated the process of structural elucidation even in high complex biological samples. In this chapter, the cur...
Chapter
Structure elucidation is an important and sometimes time-consuming step for natural products research. This step has evolved in the past few years to a faster and more automated process due to the development of several computational programs and analytical techniques. In this paper, the topics of NMR prediction and CASE programs are addressed. Fur...
Article
Full-text available
Technological advances have contributed to the evolution of the natural product chemistry and drug discovery programs. Recently, computational methods for nuclear magnetic resonance (NMR) and mass spectrometry (MS) have speeded up and facilitated the process of structural elucidation even in high complex biological samples. In this chapter, the cur...
Preprint
Highlights •Hedyosulide is a new sesterterpene lactone from Hedyosmum brasiliense Mart. ex Miq. •Hedyosulide was highly selective for the most infective forms Trypanosoma cruzi. •Most of the isolated sesquiterpene lactones were not trypanosomicidal. •This sesterterpene lactone can be a model for designing new anti-T. cruzi drugs.
Article
Full-text available
Flavonoids represent an important class of natural products with a central role in plant physiology and human health. Their accurate annotation using untargeted mass spectrometry analysis still relies on differentiating similar chemical scaffolds through spectral matching to reference library spectra. In this work, we combined molecular network ana...
Article
Full-text available
Chemical investigation of the crude PDB extract obtained from the endophytic fungus Schizophyllum commune afforded the pure substances, cyclo(L-Pro-L-Val) (1), uracil (2), cyclo(Pro-Tyr) (3), p-hydroxybenzoic acid (4) and a mixture of Rel.cyclo(Pro-Phe) (5) and Rel.cyclo(Pro-Ile) (6). When cultured in corn, the extract of this fungus yielded N-(2-p...
Article
Aim: The increase in the number of fungal infections worldwide, coupled with the limitations of current antifungal chemotherapy, demand the development of safe and effective new antifungals. Here, we presented the synthesis of a novel acridone (M14) and its antifungal properties against species of Candida and dermatophytes. Methods and results:...
Article
Ethanolic extracts of propolis are consumed for their health benefits even though direct consumption of alcoholic extracts is not always ideal. Natural Deep Eutectic Solvents (NADES) can potentially extract similar compounds as alcoholic extracts while being better for direct consumption. Therefore, in this work alternative solvents for the extract...
Article
Full-text available
Structure elucidation is an important and sometimes time-consuming step for natural products research. This step has evolved in the past few years to a faster and more automated process due to the development of several computational programs and analytical techniques. In this paper, the topics of NMR prediction and CASE programs are addressed. Fur...
Article
Full-text available
The upscaling of Xylaria cubensis, an endophyte of Eugenia brasiliensis (Myrtaceae), in PDB medium led to the isolation of known compounds including cytochalasin D (7) and cytochalasin C (8), which exhibited relatively higher phytotoxic activity in all the concentrations tested compared to the commercial herbicide GOAL®. Besides the aforementioned...
Article
Full-text available
Traditionally, the screening of metabolites in microbial matrices is performed by monocultures. Nonetheless, the absence of biotic and abiotic interactions generally observed in nature still limit the chemical diversity and leads to “poorer” chemical profiles. Nowadays, several methods have been developed to determine the conditions under which cry...
Article
Full-text available
Women have achieved great advances standing up for themselves in the last 100 years. Many important women were essential for the development of science but only a few (5% from total awarded individuals) have won Nobel prizes for their work. In this brief contribution, we would like to show that gender equality is in process and highlight the gaps t...
Article
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NuBBEDB is the first library of natural products of Brazilian biodiversity. It includes a large variety of classes of compounds and structural types of secondary metabolites of plants, fungi, insects, marine organisms and bacteria. So far the chemical diversity and complexity of NuBBEDB has not been characterized in a systematic and detailed manner...
Article
Leishmaniasis is one of the most important neglected tropical diseases (NTDs) that are especially common among low-income populations in developing regions of Africa, Asia, and the Americas. Many natural products, particularly alkaloids, have been reported to have inhibitory activity against arginase, the key enzyme in the pathology caused by Leish...
Article
Natural deep eutectic solvents have been used as an alternative to organic solvents for the extraction of plants metabolites, allowing for the extraction of compounds of different polarities, while being inexpensive, non‐toxic and easy to prepare. This work presents the comparison of the chromatographic profiles by HPLC with diode array detection o...
Article
Full-text available
We describe herein the design and synthesis of N-phenyl phthalimide derivatives with inhibitory activities against Plasmodium falciparum (sensitive and resistant strains) in the low micromolar range and noticeable selectivity indices against human cells. The best inhibitor, 4-amino-2-(4-methoxyphenyl)isoindoline-1,3-dione (10), showed a slow-acting...
Article
Full-text available
One new natural product, 1-phenylethyl-O-α-L-rhamnopyranoside, together with eight known diketopiperazines and two benzene derivatives were isolated from the endophytic fungus Colletotrichum crassipes, whereas six known compounds including two griseofulvins, three cytochalasins and one dihydroisocoumarin were produced from the endophyte Xylaria sp....
Article
Full-text available
Biologically active cyclotides have been found on some flowering plants species and are involved in the role of the plant protection. As part of studies focusing on peptides from Brazilian plant species, we are reporting the detection by LC-MS of several cyclotides from leaves and stems of Noisettia orchidiflora (Violaceae). From stems it was possi...
Article
Over the past six decades, acetonitrile (ACN) has been the most employed organic modifier in reversed-phase high-performance liquid chromatography (RP-HPLC), followed by methanol (MeOH). However, from the growing environmental awareness that leads to the emergence of “green analytical chemistry,” new research has emerged that includes finding repla...
Article
Chalcones α-β-unsaturated ketones are found in large plant species. Synthesis of chalcones and its three analogues hydroxy group at 2′, 3′ and 4′ positions (2–4) was carried out. The studies of thermal behavior were made by thermogravimetry (TG) and differential scanning calorimetry, both under oxygen and nitrogen purge gases. In addition, the kine...
Article
The natural small molecule piperlongumine A is toxic selectively to cancer cells in vitro and in vivo. This toxicity has been correlated with cancer cell ROS, DNA damage and apoptotic cell death increases. We demonstrate here a new mechanistic property of piperlongumine: it inhibits selectively human immunoproteasome with no noticeable inhibition o...
Article
Niedenzuella multiglandulosa is a plant species known for having high toxicity and to cause death in cattle and sheep, promoting economic losses in Brazilian trade balance difficult to estimate. This work aims to evaluate the potential of thermoanalytical techniques (TG–DSC, TG-FTIR) and FTIR to identify compositional differences between the powder...
Article
Full-text available
A new compound named methyl (6S,7S,2E,4E)-6,7-dihydroxy-4,6-dimethyl octanoate was isolated from Saccharicola sp. using high performance liquid chromatography-solid phase extraction-transfer tube (HPLC-SPE-TT), together with four known compounds, fusaric acid, trans-4-hydroxymellein, thymidine and adenosine. Saccharicola sp. was isolated from the s...
Article
Full-text available
Chemical investigation of the leaves of Casearia gossypiosperma Briq., Salicaceae, led to the isolation of two known flavonoids, (+)-taxifolin and quercetin, the leaves of Casearia decandra Jacq. have afforded hydroquinone, the leaves of Casearia rupestris Eichler and Casearia lasiophylla Eichler have afforded a diterpene, (E)-phytol, and the leave...
Article
Aim: This work aimed to evaluate the activity of 3'-hydroxychalcone against Cryptococcus gattii in planktonic and biofilm forms and their toxicity using alternative animal models. Materials & methods: Minimum inhibitory concentration and minimum fungicide concentration were determined. Biofilm formation and the susceptibility tests were performe...
Article
Hepatitis C virus (HCV) affects about 170 million people worldwide. The current treatment has a high cost and variable response rates according to the virus genotype. Acridones, a group of compounds extracted from natural sources, showed potential antiviral actions against HCV. Thus, this study aimed to evaluate the effect of a panel of 14 syntheti...
Article
Dodecyl protocatechuate (dodecyl) is a derivative of protocatechuic acid (3,4-dihydroxybenzoic acid) that possesses anti-oxidant and antifungal properties. Nanostructured lipid systems (NLS) can potentiate the action of many antifungal agents, reducing the required dose and side effects by improving their activity. This work aimed to evaluate dodec...
Article
Three new isoaigialones, A, B, and C (1–3), along with aigialone (4), were isolated from the crude EtOAc extract of a Phaeoacremonium sp., an endophytic fungus obtained from the leaves of Senna spectabilis. The structures of these compounds were elucidated based on the analysis of spectroscopic data. Compounds 2 and 4 were active against the phytop...
Article
Apoptosis is considered an escape mechanism from the host immune system for the fungus Paracoccidioides spp, and it serves as a vehicle for entry into macrophages without stimulating microbicidal activities. Recently, gp43 of P. brasiliensis was demonstrated to be involved in this process. Therefore, as a new therapeutic alternative, it is very imp...
Article
Artepillin C, a natural product present in the Brazilian green propolis, has several biological properties. Among these properties, the antitumor action of this product is noteworthy and makes it a promising drug candidate for the treatment of several types of cancer. This paper describes the in vitro metabolism of Artepillin C in rat and human liv...
Article
Flavonoids in the broad sense of the term are virtually universal plant pigments. Synthesis of flavanone and 6-hydroxyflavanone was carried out and identified by H and C NMR. Details concerning the thermal behavior were evaluated by thermogravimetry under oxygen and nitrogen purge gases. Additionally, the kinetic studies were evaluated from several...
Chapter
Molecular imprinting has become one of the most effective techniques in developing biomimetic material and, within these approaches, molecularly imprinted polymers (MIP) have proven their potential in synthetic recognition. Their advantages, when compared to biological material (like enzymes and antibodies), include high chemical and thermal stabil...
Article
Cryptococcosis is an opportunistic fungal infection responsible for high morbidity and mortality in immunocompromised patients. Combination of antifungal substances is a promising way to increase the percentage of successful treatment. Pedalitin (PED) is a natural substance obtained from Pterogyne nitens. The aim of this study was to verify the eff...
Article
Full-text available
Six known compounds, three peptide derivatives: cyclo-(tryptophyl-phenylalanyl) (2), diketopiperazine dimer WIN 64821 (3) and 3-hydroxy-15H-tryptophenaline (4), one adenine derivative: 2-hydroxy-6-N-isopentenyl-adenine (5), one phtalide derivative: 4-methoxyphtalide (1) and one benzoic acid derivative: 3-hydroxy-4-(1-hydroxy-1,5-dimethyl-hexyl) ben...
Article
Two rearranged sesquiterpenes, 3,5,9-trihydroxy presilphiperfolane (1) and 4-deoxy-10-oxodihydrobo- trydial (2), and two branched polyketides, 4-((E)-pent-1-enyl)-3-((1'S,2'S)-1',2'-dihydroxybut-3-enyl)- 5H-furan-2-one (3) and (2E,4R)-2,4-dimethylnon-2-enoic acid (4), along with three known compounds (2E,4S)-2,4-dimethyloct-2-enoic acid (5), xylare...
Article
Full-text available
Objective: To evaluate anti-Candida and anti-Cryptococcus activities of 15 non-alkaloidal compounds from Pterogyne nitens Tulasne (Leguminosae), a South American medicinal plant. Methods: Compounds were submitted to antifungal assays, using microdilution method described by Clinical and Laboratory Standards Institute document, with minor modificati...
Article
In this work, we present the in vitro schistosomicidal activity evaluation of the most active dichloromethane fraction (FDm) (ED50 = 83.5 μg/mL) and of a mixture of the major alkaloids ((−)-cassine/(−)-spectaline, C/E) (ED50 = 37.4 μg/mL) from the flowers of Senna spectabilis against adult worms and cercariae. We also demonstrate other toxic effect...