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Covering period: up to 2019Water-soluble natural products constitute a relevant group of secondary metabolites notably known for presenting potent biological activities. Examples are aminoglycosides, β-lactam antibiotics, saponins of both terrestrial and marine origin, and marine toxins. Although extensively investigated in the past, particularly during the golden age of antibiotics, hydrophilic fractions have been less scrutinized during the last few decades. This review addresses the possible reasons on why water-soluble metabolites are now under investigated and describes approaches and strategies for the isolation of these natural compounds. It presents examples of several classes of hydrosoluble natural products and how they have been isolated. Novel stationary phases and chromatography techniques are also reviewed, providing a perspective towards a renaissance in the investigation of water-soluble natural products.

Investigation of the endophytic fungi Nigrospora sphaerica, Nigrospora oryzae, and Pseudofusicoccum stromaticum MeOH fractions isolated from the leaves of Vochysia divergens, a medicinal species from the Brazilian Pantanal, led to the identification of five compounds, namely a new compound (1E,8Z)-10,11-dihydroxy-5,5,8-trimethyl-4-oxocycloundeca-1,8-diene-1-carbaldehyde (1) and four known compounds: 5-methylmellein (2), sclerone (3), daldinone A (4), and lasiodiplodin (5). All compounds were identified using spectroscopic methods, and 1 was corroborated with mass spectrometry, while the known compounds were compared with data in the literature. The relative configuration of compound 1 was determined based on theoretical conformational studies as well as the J experimental values between the hydroxymethyne hydrogens. The antimicrobial activity of the compounds was evaluated. Promising results were obtained for compounds 2, 4, and 5 since they inhibited the bacterium Pseudomonas aeruginosa, an opportunistic pathogen, suggesting the potential of these microorganisms as a source of new antibacterial agents.

Herein reported are results of the chemical and biological investigation of red propolis collected at the Brazilian Northeast coastline. New propolones A-D (1-4), with a 3-{3-[(2-phenylbenzofuran-3-yl)methyl]phenyl}chromane skeleton; propolonones A-C (5-7), with a 3-[3-(3-benzylbenzofuran-2-yl)phenyl]chromane skeleton; and propolol A (8), with a 6-(3-benzylbenzofuran-2-yl)-3-phenylchromane skeleton, were isolated as constituents of Brazilian red propolis by cytotoxicity-guided assays and structurally identified by analysis of their spectroscopic data. Propolone B (2) and propolonone A (5) display significant cytotoxic activities against an ovarian cancer cell line expressing a multiple drug resistance phenotype when compared with doxorubicin.

Investigation of the marine sponge Agelas dispar MeOH fractions using feature-based molecular networking, dereplication, and isolation led to the discovery of new bromopyrrole-derived metabolites. An in-house library of bromopyrrole alkaloids previously isolated from A. dispar and Dictyonella sp. was utilized, along with the investigation of an MS/MS fragmentation of these compounds. Our strategy led to the isolation and identification of the disparamides A−C (1–3), with a novel carbon skeleton. Additionally, new dispyrins B–F (4–8) and nagelamides H2 and H3 (9 and 10) and known nagelamide H (11), citrinamine B (12), ageliferin (13), bromoageliferin (14), and dibromoageliferin (15) were also isolated and identified by analysis of spectroscopic data. Analysis of MS/MS fragmentation data and molecular networking analysis indicated the presence of hymenidin (16), oroidin (17), dispacamide (18), monobromodispacamide (19), keramadine (20), longamide B (21), methyl ester of longamide B (22), hanishin (23), methyl ester of 3-debromolongamide B (24), and 3-debromohanishin (25). Antibacterial activity of ageliferin (13), bromoageliferin (14), and dibromoageliferin (15) was evaluated against susceptible and multi-drug-resistant ESKAPE pathogenic bacteria Klabsiella pneumoniae, Escherichia coli, Staphylococcus aureus, Pseudomonas aeruginosa, Acinetobacter baumannii, and Enterococcus faecalis. Dibromoageliferin (15) displayed the most potent antimicrobial activity against all tested susceptible and MDR strains. Compounds 13–15 presented no significant hemolytic activity up to 100 μM.

Microbial strains isolated from extreme and understudied environments, such as caves, are still poorly investigated for the production of bioactive secondary metabolites. Investigation of the ethyl acetate extract from the growth medium produced by the soil-derived fungus Aspergillus sp. SDC28, isolated from a Brazilian cave, yielded two anthraquinones: versicolorin C (1) and versiconol (2). The complete assignment of nuclear magnetic resonance and mass spectroscopic data of 1 and 2 was performed for the first time. Moreover, the yet unreported absolute configuration of both compounds was unambiguously established by analysis of experimental and theoretical electronic circular dichroism data. Vibrational circular dichroism was also applied to confirm the absolute stereochemistry of 2. Compounds 1 and 2 showed cytotoxic activity against human ovarian cancer cells (OVCAR3).

The COVID-19 pandemic, caused by severe acute respiratory syndrome coronavirus 2 (SARS-CoV-2), remains a global public health crisis. The reduced efficacy of therapeutic monoclonal antibodies against emerging SARS-CoV-2 variants of concern (VOCs), such as omicron BA.5 subvariants, has underlined the need to explore a novel spectrum of antivirals that are effective against existing and evolving SARS-CoV-2 VOCs. To address the need for novel therapeutic options, we applied cell-based high-content screening to a library of natural products (NPs) obtained from plants, fungi, bacteria, and marine sponges, which represent a considerable diversity of chemical scaffolds. The antiviral effect of 373 NPs was evaluated using the mNeonGreen (mNG) reporter SARS-CoV-2 virus in a lung epithelial cell line (Calu-3). The screening identified 26 NPs with half-maximal effective concentrations (EC

Made available in DSpace on 2019-10-04T12:39:55Z (GMT). No. of bitstreams: 0 Previous issue date: 2019-08-01 Conselho Nacional de Desenvolvimento Científico e Tecnológico (CNPq) National Institute of Science and Technology (INCT BioNat), Brazil National Institute of Science and Technology (INCT Areas Umidas), Brazil Fundação de Amparo à Pesquisa do Estado de São Paulo (FAPESP) Centre for Scientific Computing (NCC/GridUNESP) of Sao Paulo State University (UNESP) Prenyl indole alkaloids constitute a diverse class of natural products with complex chemical structures and potent biological activities. Investigation of the growth medium EtOAc extract produced by the endophytic fungus Aspergillus terreus P63 collected from roots of the grass Axonopus leptostachyus, yielded the prenylated indole alkaloid, giluterrin, bearing an unprecedented carbon skeleton. The structure of giluterrin was established by analysis of spectroscopic data and HRMS. The absolute configuration of giluterrin was determined by combination of electronic and vibrational circular dichroism analyses. Giluterrin presented antiproliferative profile for prostate (PC-3) and kidney (786-0) cancer cell lines. Univ Sao Paulo, Inst Quim Sao Carlos, CP 780, BR-13560970 Sao Carlos, SP, Brazil Univ Fed Mato Grosso, Dept Quim, Inst Ciencias Exatas & Terra, BR-78060900 Cuiaba, MT, Brazil Univ Fed Mato Grosso, Dept Biol, Inst Ciencias Exatas & Nat, Campus Rondonopolis, BR-78735901 Rondonopolis, MT, Brazil Inst Fed Mato Grosso, BR-78721520 Rondonopolis, MT, Brazil Univ Fed Mato Grosso do Sul, Inst Quim, BR-79070900 Campo Grande, MS, Brazil Univ Fed Mato Grosso, Inst Biociencias, BR-78060900 Cuiaba, MT, Brazil Univ Estadual Paulista, Inst Quim, Nuleo Bioensaios Biossintese & Ecofisiol Prod Nat, Dept Quim Organ, BR-14800900 Araraquara, SP, Brazil Univ Fed Mato Grosso, Dept Enfermagem, Campus Rondonopolis, BR-78735901 Rondonopolis, MT, Brazil Univ Fed Sao Carlos, Dept Quim, BR-13565905 Sao Carlos, SP, Brazil Univ Estadual Campinas, Inst Biol, Dept Biol Func & Estrutural, BR-13083865 Campinas, SP, Brazil Univ Sao Francisco, Lab Pesquisa Biol Celular & Mol Tumores & Compost, BR-12916900 Braganca Paulista, SP, Brazil Univ Fed Sao Paulo, Inst Ciencia & Tecnol, BR-12231280 Sao Jose Dos Campos, SP, Brazil Univ Estadual Paulista, Inst Quim, Nuleo Bioensaios Biossintese & Ecofisiol Prod Nat, Dept Quim Organ, BR-14800900 Araraquara, SP, Brazil National Institute of Science and Technology (INCT BioNat), Brazil: 465637/2014-0 National Institute of Science and Technology (INCT Areas Umidas), Brazil: 421733/2017-9 FAPESP: 2013/50228-8 FAPESP: 2014/25222-9

Studies of secondary metabolites (natural products) that cover their isolation, chemical synthesis and bioactivity investigation present myriad opportunities for discovery. For example, the isolation of novel secondary metabolites can inspire advances in chemical synthesis strategies to achieve their practical preparation for biological evaluation. In the process, chemical synthesis can also provide unambiguous structural characterization of the natural products. Although the isolation, chemical synthesis and bioactivity studies of natural products are mutually beneficial, they are often conducted independently. Here, we demonstrate the benefits of a collaborative study of the phomactins, diterpenoid fungal metabolites that serve as antagonists of the platelet activating factor receptor. Our isolation of novel phomactins has spurred the development of a bioinspired, unified approach that achieves the total syntheses of six congeners. We also demonstrate in vitro the beneficial effects of several phomactins in suppressing the rate of repopulation of tumour cells following gamma radiation therapy.

Marine sponges are a rich source of terpenoids with rearranged spongian carbon skeletons. Investigation of extracts from the sponge Darwinella cf. oxeata yielded four new rearranged diterpenoids, oxeatine (2) and oxeatamides H-J (3-5), as well as the known metabolites oxeatamide A (6), oxeatamide A methyl ester (7), and membranolide (1). Oxeatine (2) has a new heterocyclic skeleton, while oxeatamide J (5) has an N-methyl urea group included in a γ-lactam moiety. UPLC-QTOF analysis of the extract obtained from the mantle of the nudibranch Felimida grahami indicated the presence of 1 and 4.

A new method of screening was developed to generate 770 organic and water-soluble fractions from extracts of nine species of marine sponges, from the growth media of 18 species of marine-derived fungi, and from the growth media of 13 species of endophytic fungi. The screening results indicated that water-soluble fractions displayed significant bioactivity in cytotoxic, antibiotic, anti

Made available in DSpace on 2020-12-10T19:48:12Z (GMT). No. of bitstreams: 0 Previous issue date: 2020-01-01 Fundação de Amparo à Pesquisa do Estado de São Paulo (FAPESP) Coordenação de Aperfeiçoamento de Pessoal de Nível Superior (CAPES) A new method of screening was developed to generate 770 organic and water-soluble fractions from extracts of nine species of marine sponges, from the growth media of 18 species of marine-derived fungi, and from the growth media of 13 species of endophytic fungi. The screening results indicated that water-soluble fractions displayed significant bioactivity in cytotoxic, antibiotic, anti-Leishmania, anti-Trypanosoma cruzi, and inhibition of proteasome assays. Purification of water-soluble fractions from the growth medium of Penicillium solitum IS1-A provided the new glutamic acid derivatives solitumine A (1), solitumine B (2), and solitumidines A-D (3-6). The structures of compounds 1-6 have been established by analysis of spectroscopic data, chemical derivatizations, and vibrational circular dichroism calculations. Although no biological activity could be observed for compounds 1-6, the new structures reported for 1-6 indicate that the investigation of water-soluble natural products represents a relevant strategy in finding new secondary metabolites. Univ Sao Paulo, Inst Quim Sao Carlos, CP 780, BR-13560970 Sao Carlos, SP, Brazil Univ Fed Sao Carlos, Dept Quim, BR-13565905 Sao Carlos, SP, Brazil Univ Estadual Paulista, Inst Biociencias, Dept Bioquim & Microbiol, Campus Rio Claro,Avenida 24-A,1515, Rio Claro, SP, Brazil Univ Fed Sao Paulo, Inst Ciencia & Tecnol, BR-12231280 Sao Jose Dos Campos, SP, Brazil Univ Franca, Nucleo Pesquisa Ciencia & Tecnol, Ave Dr Armando Salles Oliveira,201 Pq Univ, BR-14404600 Franca, SP, Brazil Univ Sao Paulo, Dept Ciencias Exatas, Escola Super Agr Luiz de Queiroz, Agron, Ave Padua Dias 11,CP 9, BR-13418900 Piracicaba, SP, Brazil Natl Ctr Res Energy & Mat, Brazilian Biosci Natl Lab, Giuseppe Maximo Scolfaro 10000, BR-13083970 Campinas, SP, Brazil Univ Estadual Campinas, Inst Biol, BR-13083862 Campinas, SP, Brazil Univ Estadual Paulista, Inst Biociencias, Dept Bioquim & Microbiol, Campus Rio Claro,Avenida 24-A,1515, Rio Claro, SP, Brazil FAPESP: 2013/50228-8 FAPESP: 2016/21341-9 FAPESP: 2017/06014-4 FAPESP: 2013/23153-7 FAPESP: 2016/16033-3

Made available in DSpace on 2020-12-12T02:18:32Z (GMT). No. of bitstreams: 0 Previous issue date: 2020-10-01 Coordenação de Aperfeiçoamento de Pessoal de Nível Superior (CAPES) 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 isolated from scale-up cultures of Saccharicola sp., an endophyte of Eugenia jambolana. The structures were established by analysis of spectroscopic data, including 1D and 2D NMR. The absolute configuration of 1 was determined using Mosher's method. Speciosin U (1) and trans-3,4-dihydro-3,4-dihydroxy-anofinic acid (7) exhibited a potent acetylcholinesterase (AChE) inhibitory activity comparable to reference inhibitor galantamine. Furthermore, speciosin U (1) presented antifungal activity invitro against the phytopathogenic fungi Cladosporium cladosporioides, while compounds 4-hydroxy-3-(3′-methylbut-3′-en-1′-ynyl)-benzoic acid (4) and 4-hydroxy-3-prenyl-benzoic acid (5) exhibited antifungal activity against C. sphaerospermum. Environmental Chemistry Federal University of Tocantins UFT Chemistry Institute Department of Organic Chemistry São Paulo State University UNESP São Carlos Institute of Chemistry University of São Paulo USP CP 780 Departamento de Química Grupo de Cromatografa de Bioafnidade e Produtos Naturais Faculdade de Filosofia Ciências e Letras de Ribeirão Preto Universidade de São Paulo, USP Institute of Botany - Plant Biochemistry and Physiology Section Faculdade de Ciências Farmacêuticas Universidade Estadual Paulista UNESP Departamento de Biofísica e Fisiologia Laboratório de Cancerologia Experimental Universidade Federal do Piauí UFPI Chemistry Institute Department of Organic Chemistry São Paulo State University UNESP Faculdade de Ciências Farmacêuticas Universidade Estadual Paulista UNESP

While tetrodotoxin (TTX) is commonly found in pufferfish tissues, it is unclear if bacterial symbionts isolated from pufferfish tissues can produce TTX. In this investigation, UPLC qTOF-MS/MS analysis of tissue extracts obtained from Sphoeroides spengleri and Canthigaster figuereidoi identified TTX in their composition, indicating their consumption is unsafe. UPLC qTOF-MS/MS analysis coupled with Molecular Networking indicated new TTX analogs (methyl-TTX, TTX-acetate, hydroxypropyl-TTX and glycerol-TTX). Bacterial extracts from sixteen strains revealed a compound with a [M+H]+ ion at m/z 320.1088, identical to TTX. However, TTX itself was not detected in these cultures by UPLC-MS/MS. Neurotoxicity of Vibrio A665 purified fraction 2 (with precursor [M+H]+ ion at m/z 320.1088) was significant in human neural stem cells (hNSCs), but the Nav blockage activity was not confirmed by the veratridine/ouabain essays, indicating a possible difference in the mechanism of action between the bacterium A665 purified fraction 2 and TTX. Vibrios symbionts of pufferfish point out involving in the production of TTX precursors.

The new pyrrole-imidazole and pyrrole-guanidine alkaloids 4-debromooroidin (1), 4-debromougibohlin (2), 5-debromougibohlin (3), and 5-bromopalau'amine (4), along with the known hymenidin (5) and (+)-monobromoisophakellin (6), have been isolated from a Dictyonella sp. marine sponge, collected at the Amazon River mouth. The bromine-substitution pattern observed for compounds 1, 2 and 4 is unusual among bromopyrrole alkaloids isolated from marine sponges. The 20S proteasome inhibitory activities of compounds 1-6 have been recorded, with 5-bromopalau'amine (4) being the most active in this series.

Made available in DSpace on 2020-12-12T01:09:13Z (GMT). No. of bitstreams: 0 Previous issue date: 2020-01-01 Coordenação de Aperfeiçoamento de Pessoal de Nível Superior (CAPES) Fundação de Amparo à Pesquisa do Estado de São Paulo (FAPESP) Conselho Nacional de Desenvolvimento Científico e Tecnológico (CNPq) This work is aimed at investigating the effects of ascorbic acid as sacrificial agent in the photoelectrocatalytic reduction of CO2 to alcohol. The results show that the addition of electron donor agent (0.2 mol L−1 ascorbic acid) to the electrolyte (0.1 mol L−1 sodium sulfate pH 4.5) led to an improvement of 22% and 12% in CO2/methanol and CO2/ethanol conversion respectively, after 3 h of photoelectrolysis conducted on TiO2 nanotubes decorated with ZIF-8 nanoparticles under Eapp = 0.1 V and UV–Vis irradiation. The photoelectrocatalytic results were compared with photocatalytic, photolytic and electrocatalytic performance. The findings of this work unfold an interesting perspective for the use of sacrificial agent in photoelectrocatalysis and the generation of products of great energetic value from pollutants that cause environmental degradation in systems carried out under constant pressure and low temperature. Institute of Chemistry Federal University of Mato Grosso do Sul, Av. Senador Filinto Muller, 1555, CP 549 Universidade do Vale do Taquari (Univates) Center of Sciences and Engineering São Paulo State University (UNESP) Institute of Chemistry Instituto de Química de São Carlos Universidade de São Paulo, CP 780 São Paulo State University (UNESP) Institute of Chemistry FAPESP: 2014/50945-1 FAPESP: 2015/18109-4 CNPq: 310253/2016-0 CNPq: 409792/2018-7

Two new eremophilane-type sesquiterpenes, xylarenones F (3) and G (4), have been isolated from solid substrate cultures of a Camarops sp. endophytic fungus isolated from Alibertia macrophylla, together with the known compounds xylarenones C (1) and D (2). The structures and relative configurations of 1-4 were elucidated by extensive NMR and HRESIMS spectroscopic analysis. Due to their effects on the respiratory burst of neutrophils, which included inhibition of the reactive oxygen species production, these sesquiterpenes exhibited potential anti-inflammatory and antioxidant properties.

Made available in DSpace on 2018-12-11T16:45:55Z (GMT). No. of bitstreams: 0 Previous issue date: 2017-01-01 China Scholarship Council National Institute of General Medical Sciences National Cancer Institute Incorporation of the histone deacetylase (HDAC) inhibitor, suberoylanilide hydroxamic acid (SAHA), to a culture broth of the endophytic fungus Phoma sp. nov. LG0217 isolated from Parkinsonia microphylla changed its metabolite profile and resulted in the production of (10′S)-verruculide B (1), vermistatin (2) and dihydrovermistatin (3). When cultured in the absence of the epigenetic modifier, it produced a new metabolite, (S,Z)-5-(3′,4′-dihydroxybutyldiene)-3-propylfuran-2(5H)-one (4) together with nafuredin (5). The structure of 4 was elucidated by spectroscopic analyses and its absolute configuration was determined by application of the modified Mosher's ester method. The absolute structure of (10′S)-verruculide B was determined as 5-[(10′S,2′E,6′E)-10′,11′-dihydroxy-3′,7′,11′-trimethyldodeca-2′,6′-dien-1′-yl]-(3R)-6,8-dihydroxy-3-methylisochroman-1-one (1) with the help of CD and NOE data. Compound 1 inhibited the activity of protein tyrosine phosphatases (PTPs) 1B (PTP1B), Src homology 2-containing PTP 1 (SHP1) and T-cell PTP (TCPTP) with IC50values of 13.7���3.4, 8.8���0.6, and 16.6���3.8�μM, respectively. Significance of these activities and observed modest selectivity of 1 for SHP1 over PTP1B and TCPTP is discussed. Natural Products Center School of Natural Resources and the Environment College of Agriculture and Life Sciences University of Arizona, 250 E. Valencia Road NuBBE – N�cleo de Bioensaios Bioss�ntese e Ecofisiologia de Produtos Naturais Departamento de Qu�mica Org�nica Instituto de Qu�mica UNESP Universidade Estadual Paulista Department of Pharmacology and Toxicology College of Pharmacy University of Arizona School of Plant Sciences College of Agriculture and Life Sciences University of Arizona NuBBE – N�cleo de Bioensaios Bioss�ntese e Ecofisiologia de Produtos Naturais Departamento de Qu�mica Org�nica Instituto de Qu�mica UNESP Universidade Estadual Paulista National Institute of General Medical Sciences: P41 GM094060 National Cancer Institute: R01 CA090265

Made available in DSpace on 2018-11-26T17:16:37Z (GMT). No. of bitstreams: 0 Previous issue date: 2016-12-01. Added 1 bitstream(s) on 2019-10-09T18:26:28Z : No. of bitstreams: 1 S0100-40422016001001221.pdf: 307314 bytes, checksum: 6b335c5840da812552d884ce513fa034 (MD5) Fundação de Amparo à Pesquisa do Estado de São Paulo (FAPESP) Conselho Nacional de Desenvolvimento Científico e Tecnológico (CNPq) Coordenação de Aperfeiçoamento de Pessoal de Nível Superior (CAPES) Seven phenolic derivatives including p-hydroxyphenyllactic acid (1), p-hydroxybenzoic acid (2), p-hydroxybenzaldehyde (3), phenyllactic acid (4), n-butyl-3,4-dihydroxybenzoate (5), n-hexyl-3,4-dihydroxybenzoate (6) and n-octyl-3,4-dihydroxybenzoate (7) were produced using Camarops sp. via the one strain-many compounds (OSMAC) approach. Their structures were determined using 2D NMR and ESI-MS spectra and were compared with works reported in the literature. This paper deals with the first report of these compounds in Camarops sp. Univ Estadual Paulista, Inst Quim, Dept Quim Organ, NuBBE Nucleo Bioensaios Biossintese & Ecofisiol P, BR-14800900 Araraquara, SP, Brazil Univ Fed Tocantins, Colegiado Ciencias Exatas & Biotecnol, BR-77402970 Gurupi, TO, Brazil Univ Fed Vicosa, Inst Ciencias Exatas & Tecnol, BR-38810000 Rio Paranaiba, MG, Brazil Univ Estadual Paulista, Inst Quim, Dept Quim Organ, NuBBE Nucleo Bioensaios Biossintese & Ecofisiol P, BR-14800900 Araraquara, SP, Brazil FAPESP: 2013/07600-3 CNPq: 563286/2010-5

Made available in DSpace on 2018-11-26T17:24:25Z (GMT). No. of bitstreams: 0 Previous issue date: 2017-02-01. Added 1 bitstream(s) on 2019-10-09T18:26:38Z : No. of bitstreams: 1 S0100-40422017000200138.pdf: 202296 bytes, checksum: c62a99e173bd0ac6821167f6739b0587 (MD5) Fundação de Amparo à Pesquisa do Estado de São Paulo (FAPESP) Conselho Nacional de Desenvolvimento Científico e Tecnológico (CNPq) Coordenação de Aperfeiçoamento de Pessoal de Nível Superior (CAPES) 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) benzoic acid (6), were isolated from the ethyl acetate extract of the endophytic fungus Aspergillus versicolor associated with the Piper aduncum plant. Their structures were determined on the basis of detailed interpretation of 1 D and 2D NMR spectra and in comparison with works reported in the literature. This paper, in effect, deals with the first report of these compounds in A. versicolor. Univ Estadual Paulista, Inst Quim, Dept Quim Organ, BR-14800900 Araraquara, SP, Brazil Univ Fed Mato Grosso, Dept Ciencias Biol, BR-78735901 Rondonopolis, MT, Brazil Univ Fed Vicosa, Inst Ciencias Exatas & Tecnol, BR-38810000 Rio Paranaiba, MG, Brazil Inst Bot, Nucleo Pesquisa Fisiol & Bioquim, BR-01061970 Sao Paulo, SP, Brazil Univ Amazonas, Fac Ciencias Agr, BR-69077000 Manaus, Amazonas, Brazil Univ Estadual Paulista, Inst Quim, Dept Quim Organ, BR-14800900 Araraquara, SP, Brazil FAPESP: 03/02176-7 FAPESP: 2013/07600-3 CNPq: 563286/2010-5