Massuo Jorge Kato

• PhD
• Professor (Full) at University of São Paulo

Declines in biodiversity generated by anthropogenic stressors at both species and population levels can alter emergent processes instrumental to ecosystem function and resilience. As such, understanding the role of biodiversity in ecosystem function and its response to climate perturbation is increasingly important, especially in tropical systems w...

Declines in biodiversity generated by anthropogenic stressors at both species and population levels can alter emergent processes instrumental to ecosystem function and resilience. As such, understanding the role of biodiversity in ecosystem function and its response to climate perturbation is increasingly important, especially in tropical systems w...

The potential emergence of zoonotic diseases has raised significant concerns, particularly in light of the recent pandemic, emphasizing the urgent need for scientific preparedness. The bioprospection and characterization of new molecules are strategically relevant to the research and development of innovative drugs for viral and bacterial treatment...

Quinolizidine alkaloids (QAs) are nitrogen-containing compounds produced naturally as specialized metabolites distributed in plants and animals (e.g., frogs, sponges). The present review compiles the available information on the chemical diversity and biological activity of QAs reported during the last three decades. So far, 397 QAs have been isola...

Declines in biodiversity generated by anthropogenic stressors at both species and population levels can alter emergent processes instrumental to ecosystem function and resilience. As such, understanding the role of biodiversity in ecosystem function and its response to climate perturbation is increasingly important, especially in tropical systems w...

Declines in biodiversity generated by anthropogenic stressors at both species and population levels can alter emergent processes instrumental to ecosystem function and resilience. As such, understanding the role of biodiversity in ecosystem function and its response to climate perturbation is increasingly important, especially in tropical systems w...

The Genisteae tribe belongs to the Fabaceae family. The wide occurrence of secondary metabolites, explicitly highlighting the quinolizidine alkaloids (QAs), characterizes this tribe. In the present study, twenty QAs (1-20), including lupanine (1-7), sparteine (8-10), lupanine (11), cytisine and tetrahydrocytisine (12-17), and matrine (18-20)-type Q...

Declines in biodiversity generated by anthropogenic stressors at both species and population levels can alter emergent processes instrumental to ecosystem function and resilience. As such, understanding the role of biodiversity in ecosystem function and its response to climate perturbation is increasingly important, especially in tropical systems w...

Peperomia incana (Haw.) A. Dietr. as a new source of cannabinoids with cytotoxic and microbial activities

Plastoquinone is a key electron carrier in photosynthesis and an essential cofactor for the biosynthesis of carotenoids. p-Hydroxyphenylpyruvate dioxygenase (HPPD) is a vital enzymatic step in plastoquinone biosynthesis that is the target of triketone herbicides, such as those derived from the pharmacophore backbone of the natural product leptosper...

Species richness in tropical forests is correlated with other dimensions of diversity, including the diversity of plant–herbivore interactions and the phytochemical diversity that influences those interactions. Understanding the complexity of plant chemistry and the importance of phytochemical diversity for plant–insect interactions and overall for...

Malaria is one of the most widespread parasitic diseases, especially in Africa, Southeast Asia and South America. One of the greatest problems for control of the disease is the emergence of drug resistance, which leads to a need for the development of new antimalarial compounds. The biosynthesis of isoprenoids has been investigated as part of a str...

Urodele amphibians (∼768 spp.), salamanders and newts, are a rich source of molecules with bioactive properties, especially those isolated from their skin secretions. These include pharmacological attributes, such as antimicrobial, antioxidant, vasoactive, immune system modulation, and dermal wound healing activities. Considering the high demand fo...

Several Piper species accumulate piperamides as secondary metabolites, and although they have relevant biological importance, many details of their biosynthetic pathways have not yet been described experimentally. Experiments involving enzymatic reactions and labeled precursor feeding were performed using the species Piper tuberculatum and Piper ar...

In addition to the morphophysiological changes experienced by amphibians during metamorphosis, they must also deal with a different set of environmental constraints when they shift from the water to the land. We found that Pithecopus azureus secretes a single peptide ([M + H]+ = 658.38 Da) at the developmental stage that precedes the onset of terre...

Foundational hypotheses addressing plant–insect codiversification and plant defense theory typically assume a macroevolutionary pattern whereby closely related plants have similar chemical profiles. However, numerous studies have documented variation in the degree of phytochemical trait lability, raising the possibility that phytochemical evolution...

The continuous and indiscriminate use of insecticides has been responsible for the emergence of insecticide resistant vector insect populations, especially in Aedes aegypti. Thus, it is urgent to find natural insecticide compounds with novel mode of action for vector control. The goal of this study was to investigate the larvicidal activity of esse...

The chemical composition of seedlings and adult plants of several Piper species were analyzed by ¹H NMR spectroscopy combined with principal component analysis (PCA) and HPLC-DAD, HPLC-HRESIMS and GC-MS data. The chromatographic profile of crude extracts from leaves of Piper species showed remarkable differences between seedlings and adult plants....

The genus Eois Hübner (Geometridae: Larentiinae) comprises 254 valid species, 217 of which were described from the Neotropics and 31 of those having their type locality in Brazil. Since this species rich genus has never been revised, and may potentially include many cryptic undescribed species, Eois embodies a problematic taxonomic scenario. The ac...

Leishmaniasis is considered a neglected disease, which makes it an unattractive market for the pharmaceutical industry; hence, efforts in the search for biologically active substances are hampered by this lack of financial motivation. Thus, in the present study, we report the leishmanicidal activity and the possible mechanisms of action of compound...

The genus Eois Hübner (Geometridae: Larentiinae) comprises 254 valid species. Being a hyperdiverse genus, Eois potentially includes many undescribed cryptic species and embodies a problematic taxonomic scenario. The actual diversity of Eois is greatly underestimated and the Neotropical fauna needs to be well known since it figures as one of the mos...

Plant secondary chemistry is known to be an important driver of plant–insect community structure across ecological scales. Recently, the concept of phytochemical diversity (PD) has been introduced to help describe variation in plant secondary chemistry and explain how this variation affects community structure. Previous studies show that PD among i...

Peperomia pellucida (L.) HBK (Piperaceae) (“jabuti herb”) is an herbaceous plant that is widespread in the tropics and has several ethnomedicinal uses. The phytochemical study of leaf extracts resulted in the isolation of 2,4,5-trimethoxycinnamic acid, 5,6,7-trimethoxyflavone, 2,4,5-trimethoxystyrene, 2,4,5-trimethoxybenzaldehyde, dillapiol, and se...

Aniba rosiodora has been exploited since the end of the nineteenth century for its essential oil, a valuable ingredient in the perfumery industry. This species occurs mainly in Northern South America, and the morphological similarity among different Aniba species often leads to misidentification, which impacts the consistency of products obtained f...

Over evolutionary timescales, shifts in plant secondary chemistry may be associated with patterns of diversification in associated arthropods. Although foundational hypotheses of plant-insect codiversification and plant defense theory posit closely related plants should have similar chemical profiles, numerous studies have documented variation in t...

Piper is one of two large genera in the Piperaceae, and with ca. 2600 species, is one of the largest plant genera in the world. Species delimitation and evaluation of genetic diversity among populations are important requisites for conservation and adequate exploitation of economically important species. DNA barcoding has been used as a powerful to...

Malaria, caused by protozoa of the genus Plasmodium, is a disease that infects hundreds of millions of people annually, causing an enormous social burden in many developing countries. Since current antimalarial drugs are starting to face resistance by the parasite, the development of new therapeutic options has been prompted. The enzyme Plasmodium...

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Altered cell metabolism is a hallmark of cancer and critical for its development. Particularly, activation of one-carbon metabolism in tumor cells can sustain oncogenesis while contributing to epigenetic changes and metabolic adaptation during tumor progression. We assessed whether increased one-carbon metabolism activity is a metabolic feature of...

Isoxazole analogues derived from the neolignans veraguensin, grandisin, and machilin G were previously synthesized with different substitution patterns through the bioisosterism strategy. These compounds were tested on intracellular amastigotes of Leishmania (Leishmania) amazonensis; the derivatives proved to be active against intracellular amastig...

Banana (Musa spp.) is an important crop worldwide, but black Sigatoka disease caused by the fungus Pseudocercospora fijiensis threatens fruit production. In this work, we examined the potential of the endophytes of banana plants Enterobacter cloacae and Klebsiella pneumoniae, as antagonists of P. fijiensis and support plant growth in nutrient limit...

Amides have been recognized as potent insecticidal natural products but, despite their variety of targets and mechanisms of action, their metabolic fate in insects is virtually unknown. The currently accepted hypothesis is that specialist herbivores are capable of biotransforming xenobiotics rendering them more polar and excretable while generalist...

Background/Aim: Colorectal cancer is a common type of cancer with reported resistance to treatment, in most cases due to loss of function of apoptotic and cell-cycle proteins. Piperlongumine (PPLGM) is a natural alkaloid isolated from Piper species, with promising anti-cancer properties. This study investigated whether PPLGM is able to induce cell...

Using bioisosterism as a medicinal chemistry tool, 16 3,5‐diaryl‐isoxazole analogues of the tetrahydrofuran neolignans veraguensin, grandisin and machilin G were synthesized via 1,3‐dipolar cycloaddition reactions, with yields from 43% to 90%. Antitrypanosomatid activities were evaluated against Trypanosoma cruzi, Leishmania (L.) amazonensis and Le...

Póster PSNA 2018

Sit-and-wait predators use different strategies to encounter potential prey. Rhinoleucophenga myrmecophaga Vidal et (Vidal et Vilela; Diptera: Drosophilidae) larvae build sticky shelters on top of extrafloral nectaries (EFNs) of Qualea grandiflora Mart (Vochysiaceae), a common plant in the Brazilian cerrado savanna. Although larval shelters block t...

Schistosomiasis, caused by helminth flatworms of the genus Schistosoma, is an infectious disease mainly associated with poverty that affects millions of people worldwide. Since treatment for this disease relies only on the use of praziquantel, there is an urgent need to identify new antischistosomal drugs. Piplartine is an amide alkaloid found in s...

Amides are important natural products which occur in a few plant families. Piplartine and piperine, major amides in Piper tuberculatum and P. nigrum, respectively, have shown a typical N–CO cleavage when analyzed by EI-MS or HRESI-MS. In this study several synthetic analogs of piplartine and piperine were subjected to both types of mass spectrometr...

As part of our continuing phytochemical survey on Piper species, three previously undescribed alkenylphenols were isolated and characterized, including 4-[(3′E)-tetradec-3′-en-1-yl] phenol (1) and 4-[(2′E,4′E)-heptadeca-2′,4′-dien-1-yl] phenol (3) from P. diospyrifolium and 4-[(3′E)-hexadec-3′-en-1-yl] phenol (2) from P. dilatatum. The structures o...

The phytochemical study on dichlorometane extracts of leaves, stem and roots of Piper mollicomum Kunth (Piperaceae) led to isolation of the known piperamides tembamide (1), (R)-(-)-tembamide acetate (2) and riparin I (3). Compounds 1 and 2 displayed moderate in vitro antifungal activity against Cladosporium cladosporioides (5.0 μg) and Cladosporium...

The phytochemical study on dichlorometane extracts of leaves, stem and roots of Piper mollicomum Kunth (Piperaceae) led to isolation of the known piperamides tembamide (1), (R)-(-)-tembamide acetate (2) and riparin I (3). Compounds 1 and 2 displayed moderate in vitro antifungal activity against Cladosporium cladosporioides (5.0 μg) and Cladosporium...

Phytochemical variation among plant species is one of the most fascinating and perplexing features of the natural world and has implications for both human health and the functioning of ecosystems. A key area of research on phytochemical variation has focused on insects that feed on plants and the enormous diversity of plant-derived compounds that...

Many isolates of the genus Photorhabdus have been reported around the world. Here we describe the first Brazilian Photorhabdus isolate, found in association with the entomopathogenic nematode Heterorhabditis baujardi LPP7, from the Amazonian forest in Monte Negro (RO, Brazil). The new isolate can be grouped with the Hb-Hm clade of P. luminescens su...

Piper gaudichaudianum Kunth (Piperaceae) accumulates gaudichaudianic acid, a prenylated benzopyran, as its major component. Interestingly, this trypanocidal compound occurs as a racemic mixture. Herein, transcriptomic investigations of Piper gaudichaudianum using the RNA-seq approach are reported, and from the analysis of the transcripts expressed...

Bragantina and Cingapura are the main black pepper (Piper nigrum L.) cultivars and the Pará state is the largest producer in Brazil with about 90% of national production, representing the third largest production in the world. The infection of Fusarium solani f. sp. piperis, the causal agent of Fusarium disease in black pepper, was monitored on the...

Secondary metabolites from plants possess a wide range of chemical structures and functions [1]. They play an important role in plants life cycle and are recruited in defense roles especially against pathogens and herbivores.[2,3] Most of the phytochemical studies have been carried out on adult individuals. Studies on seedlings and throughout the p...

The study of variability of the tetrahydrofuran lignan (−)-grandisin in leaves of Piper solmsianum (Piperaceae) revealed two unknown compounds, that were isolated and determined to be the all-cis tetrahydrofuran lignans 1a [rel-(7R,8S,7′S,8′R)-3,4,5,3′,4′,5′-hexamethoxy-7,7′-epoxylignan] and 1b [rel-(7R,8S,7′S,8R′)-3′,4′-methylenedioxy-3,4,5,5′-tet...

Piper tuberculatum (Piperaceae) is a species that accumulates especially amides as secondary metabolites and several biological activities was previously reported. In this article, we report a proteomic study of P. tuberculatum. Bidimensional electrophoresis (2D SDS-PAGE) and mass spectrometry (ESI-Q-TOF) were used in this study. Over a hundred spo...

Piplartine, an alkaloid produced by plants in the genus Piper, displays promising anticancer activity. Understanding the gas-phase fragmentation of piplartine by electrospray ionization tandem mass spectrometry can be a useful tool to characterize biotransformed compounds produced by in vitro and in vivo metabolism studies. As part of our efforts t...

A longstanding paradigm in ecology is that there are positive associations between herbivore diversity, specialization, and plant species diversity, with a focus on taxonomic diversity. However, phytochemical diversity is also an informative metric, as insect herbivores interact with host-plants not as taxonomic entities, but as sources of nutrient...

Peperomia obtusifolia, an ornamental plant from the Piperaceae family, accumulates a series of secondary metabolites with interesting biological properties. From a biosynthesis standpoint, this species produces several benzopyrans derived from orsellinic acid, which is a polyketide typically found in fungi. Additionally, the chiral benzopyrans were...

Context: Plants of the Piperaceae family produce piplartine that was used to synthesize the cinnamides. Objective: To assess the effects of piplartine (1) and cinnamides (2–5) against the protozoa responsible for malaria and leishmaniasis, and peritoneal cells of Swiss mice. Materials and methods: Cultures of Leishmania amazonensis, Plasmodium falc...

Schistosomiasis is a world health problem, and praziquantel is the only drug currently used for the treatment. There is some evidence that extensive monotherapy of praziquantel may be leading to drug resistance in the parasite. In order to find alternative treatments, the effects of the combination of epiisopiloturine (EPI), piplartine (PPT) and pr...

In this study, the potential antileukemic activity of grandisin, a lignan extracted from Piper solmsianum, was evaluated against the leukemic line K562. The cytotoxicity of grandisin (0.018 to 2.365 µM) was evaluated in K562 and normal peripheral blood lymphocytes by Trypan Blue Exclusion and MTT methods after 48h exposure to the drug. In both meth...

The known kavalactones (E)-4-methoxy-6-styryl-2H-pyran-2-one, 4-methoxy-6-(3-phenyloxiran-2-yl)-2H-pyran-2-one, 6-(1,2-dihydroxy-2-phenylethyl)-4-methoxy-2H-pyran-2-one, the three benzoic acid derivatives methyl-4-methoxy-3-(3’-methyl-2’-butenyl)benzoate and methyl 2,2-dimethyl-4-oxochroman-6-carboxylate, and a new methyl 4-methoxy-3-(3-methylbut-2...

The Peperomia is one of the giant genus among Angiosperms with approximately 1600 species spread in the tropics. Their species are valuable as ornamental and several medicinal uses were described but their phytochemistry is poorly investigated compared to Piper (2000 species). In spite of this scarcity, typical classes of secondary metabolites isol...

Phylloquinone is a redox active naphthoquinone involved in electron transport in plants. The function of this reduced form remains unclear due to its instability, which has precluded detection. Herein, a simple method that permits the stabilization of the reduced form of phylloquinone by di-O-methylation and HPLC detection is described.

While MALDI imaging is providing many interesting findings as regards metabolite localization in phytochemical factories in specialized cell types in situ, one major problem is in ensuring that localization data can distinguish between isobaric (same molecular weight) species. Accordingly, we considered that by applying ion mobility mass spectromet...

Crude CH2Cl2 extract from leaves of Piper laevicarpu (Piperaceae) displayed antitrypanosomal activity against trypomastigote forms of Trypanosoma cruzi (Y strain) and antimicrobial potential against Cryptococcus gattii (strain-type WM 178). Bioactivity-guided fractionation of crude extract afforded one new natural bioactive lactam derivative, named...

Vascular plant species in the Piperaceae produce different classes of important bioactive compounds, including lignans and neolignans, alkaloids, amides, prenylated benzoic acids and chromenes, dihydrochalcones, flavonoids, and various phenylpropanoids. For example, Piper solmsianum accumulates (-)-grandisin whose anti-chagasic properties are docum...

The silverleaf whitefly Bemisia tabaci (Genn.) biotype B (Hemiptera: Aleyrodidae) is one of the most severe tomato pests in the world. The damage caused by this insect may compromise up to 100% of crop production, and management of this pest has relied on spraying of synthetic insecticides. However, due to the environmental issues associated with t...

The use of the voltammetry of immobilized particles (VIMP) approach, by means of the voltammetric response of microparticulate films from ethanolic leaf extracts in contact with aqueous electrolytes and direct contact probe leaf voltammetry, to monitor the defense of plants against external stressors is described. This approach is applied to study...

The Sairecabur volcano (5971 m), in the Atacama Desert, is a high-altitude extreme environment with high daily temperature variations, acidic soils, intense UV radiation, and low availability of water. Four different species of yeasts were isolated from this region using oligotrophic media, identified and characterized for their tolerance to extrem...

Plants form symbiotic associations with endophytic bacteria within tissues of leaves, stems, and roots. It is unclear whether or how plants obtain nitrogen from these endophytic bacteria. Here we present evidence showing nitrogen flow from endophytic bacteria to plants in a process that appears to involve oxidative degradation of bacteria. In our e...

Common bean (Phaseolus vulgaris) is present in the daily diet of various countries and, as for other legumes, has been investigated for its nutraceutical potential. Thus, 16 genotypes from different gene pools, representing seven types of seed coats and different responses to pathogens and pests, were selected to verify their isoflavone contents. T...

The presence of peptides has been identified in all African pipid genera; nevertheless, little is known about skin secretion of South American frog genus Pipa. Skin secretion from captive and wild Pipa carvalhoi were obtained in the presence or absence of norepinephrine stimulation. The <10kDa fraction was analyzed by liquid chromatography and mass...

The essential oils are a notably complex natural mixture, and due to the complexity of the sample and of the analysis, new methods, such as two-dimensional gas chromatography, should be tested to show the enhanced sensitivity and superior resolution of comprehensive two-dimensional gas chromatography (GC × GC). In the present work, the chemical com...

Bioactivity-guided fractionation of the separate CH2Cl2 extracts from the aerial parts of Peperomia alata and P. trineura yielded seven polyketides: alatanone A [3-hydroxy-2-(5'-phenylpent-4'E-enoyl)cyclohex-2-en-1-one, 1a] and alatanone B [3-hydroxy-2-(3'-phenyl-6'-methylenedioxypropanoyl)cyclohex-2-en-1-one, 2a] from P. alata and trineurone A [3-...

The search of alternative compounds to control tropical diseases such as schistosomiasis has pointed to secondary metabolites derived from natural sources. Piper species are candidates in strategies to control the transmission of schistosomiasis due to their production of molluscicidal compounds. A new benzoic acid derivative and three flavokawains...

The effectiveness of the amides piplartine and piperlonguminine isolated from Piper species for controlling L3 and L4 of Aedes aegypti (L.) was assessed through bioassays at concentrations ranging from 1 to 300 g/l ml. Piplartine reduced the mosquito development period and caused larval mortality only at concentrations > 100 microg/ml, whereas pipe...

• Premise of the study: Nine microsatellite (simple sequence repeat [SSR]) loci were characterized for natural populations of Piper solmsianum, a potential source of bioactive secondary metabolites, and analyzed to assess the levels of genetic diversity in this species. • Methods and Results: Based on an enriched library using the oligonucleotides...

The known prenylated benzoic acid derivative 3-geranyl-4-hydroxy-5-(3″,3″-dimethylallyl)benzoic acid (1) and two new chromane natural products were isolated from the methanolic extract of the leaves of Piper kelleyi Tepe (Piperaceae), a midcanopy tropical shrub that grows in lower montane rain forests in Ecuador and Peru. Structure determination us...

The increased demand for drug discovery of plant origin led organic chemists to intensify studies to elucidate the metabolic pathway of some metabolites of interest. Often, these metabolites show low accumulation in plant matrices and / or exhibit structural complexity, which make it impossible to obtain them by synthesis or semi-synthesis. Thus, u...

Piper regnellii (Piperaceae) contains high levels neolignans with diverse biological activities, including insecticidal. Despite the insecticidal activity of these neolignans, Naupactus bipes (Coleoptera: Curculionidae) larvae and adults were found feeding on the leaves (adults) and roots (larvae) of P. regnellii. The present study investigated the...