The genus Trichilia, belonging to the Meliaceae family, comprises ca. 102 species, some of which have been the subject of phytochemical studies. Compounds of different classes with cytotoxic, antimicrobial, and antioxidant activities were isolated from Thichilia. Trichilia pseudostipularis, a native species, is distributed along the entire Brazilian coast, from southern Santa Catarina to Bahia. Due to the inexistence of previous chemical studies, their wood and roots were investigated. Compounds 3,4-dihydro-4-isopropyl-6-methylnaphthalen-1(2H)-one (1), 3,4-dihydro-7-hydroxy-4-isopropyl-6-methylnaphthalen-1(2H)-one (2), and pseudostipulariol (3) were isolated from wood, while the lactone derivate rel-(2S,3S,4R)-3-hydroxy-4-methyl-2-(13”-phenyl-l’-n-tridecyl)-butanolide (4) was isolated from the roots. Compounds 3 and 4 are reported for the first time. family ca 10 species studies cytotoxic antimicrobial Thichilia pseudostipularis coast Bahia investigated 3,4dihydro4isopropyl6methylnaphthalen12Hone 34dihydro4isopropyl6methylnaphthalen12Hone dihydroisopropylmethylnaphthalenHone 3,4 dihydro isopropyl 6 methylnaphthalen 1 2H one H 1, , (1) 3,4dihydro7hydroxy4isopropyl6methylnaphthalen12Hone 34dihydro7hydroxy4isopropyl6methylnaphthalen12Hone dihydrohydroxyisopropylmethylnaphthalenHone 7 hydroxy 2, 2 (2) (3 rel2S,3S,4R3hydroxy4methyl213phenyllntridecylbutanolide rel2S3S4R3hydroxy4methyl213phenyllntridecylbutanolide relSSRhydroxymethylphenyllntridecylbutanolide rel 2S,3S,4R methyl 13 phenyl l n tridecyl butanolide 2S 3S 4R S R (4 time 4dihydro4isopropyl6methylnaphthalen12Hone Hone 34 3, (1 4dihydro7hydroxy4isopropyl6methylnaphthalen12Hone (2 ( rel2S 4R3hydroxy4methyl213phenyllntridecylbutanolide phenyllntridecylbutanolide 2S3S4R SSR relS Rhydroxymethylphenyllntridecylbutanolide

A new alkaloid, named brazoide Ε (6), three known steroids (campesterol, β-sitosterol, stigmasterol), two glucosides (3-O-β-D-glucopyranosylsitosterol and 3-O-β-D-glucopyranosyl stigmasterol) and sucrose were isolated from the leaves and stems of Justicia wasshauseniana. Their structures were characterized using high-resolution electrospray ionization mass spectrometry (HRESIMS), nuclear magnetic resonance (1D and 2D NMR), and infrared (IR) spectroscopy. To reinforce the structural proposal, an acetylated derivative (6a) was obtained and its data compared to 6. Moreover, circular dichroism spectroscopy (CD) analysis was performed to determine the absolute stereochemistry, time-dependent density functional theory (TD-DFT) at the wB97X-D/def2-TZVP level, adopting functionals M06-2X and wB97X-D and base aug-cc-pVDZ, was employed to confirm the CD analysis. alkaloid 6, 6 , (6) campesterol, campesterol (campesterol βsitosterol, βsitosterol β sitosterol, sitosterol β-sitosterol stigmasterol, stigmasterol 3OβDglucopyranosylsitosterol OβDglucopyranosylsitosterol 3 O D glucopyranosylsitosterol 3OβDglucopyranosyl OβDglucopyranosyl glucopyranosyl wasshauseniana highresolution high resolution HRESIMS, HRESIMS (HRESIMS) 1D NMR, NMR NMR) IR (IR proposal 6a a (6a Moreover (CD stereochemistry timedependent time dependent TDDFT TD DFT (TD-DFT wB97XD/def2TZVP wB97XDdef2TZVP wBXDdefTZVP wB97X D/def2 TZVP def2 wB X def level M062X MX M06 2X M wB97XD wBXD augccpVDZ, augccpVDZ aug cc pVDZ, pVDZ aug-cc-pVDZ (6 (HRESIMS def2TZVP XD XDdef wBX Ddef2 Ddef D/def M0 ( defTZVP

A new phenylpropanoid derivative, named euploic acid (1), was isolated from Euploca procumbens (Mill.) Diane & Hilger, Boraginaceae, along with lithospermic acid B (2), lithospermic acid (3), 9’’-methyl lithospermate (4), and luteolin-7-O-glucoside (5). Compound structures were determined by mass spectrometry (MS), nuclear magnetic resonance (NMR) analysis and comparison with published data. Absolute configuration of 1 was established via electronic circular dichroism (ECD). Anti-inflammatory potential of euploic acid (1) was assessed by measuring its inhibition of cytokine and nitric oxide production in stimulated J774 macrophages. Compound 1 significantly reduced pro-inflammatory mediator production and release by stimulated macrophages at non-cytotoxic concentrations, comparable to the efficacy of dexamethasone. Our findings demonstrate the potential of euploic acid (1) as an effective anti-inflammatory agent. This study contributes to the structural elucidation of a new phenylpropanoid derivative and highlights its promising anti-inflammatory activity in the treatment of inflammatory disorders. 1, , Mill. Mill (Mill. Hilger Boraginaceae 2, 2 (2) 3, 3 (3) 9methyl methyl 9 4, 4 (4) luteolin7Oglucoside luteolinOglucoside luteolin 7 O glucoside 5. 5 . (5) MS, MS (MS) NMR (NMR data ECD. ECD (ECD) Antiinflammatory Anti (1 J J77 proinflammatory pro noncytotoxic non cytotoxic concentrations dexamethasone antiinflammatory anti agent disorders (Mill (2 (3 (4 Oglucoside (5 (MS (ECD ( J7

Abstract Diplopods are terrestrial arthropods important for the dynamics of terrestrial ecosystems. One of the reasons for that can be their low predation rate due to their defensive secretion. Thus, Orthoporus fuscipes, a species belonging to this group and endemic to northeastern Brazil, was investigated as to its population structure and chemical constituents of defensive secretion. The population structure showed that females are larger and have greater mass than do males, along with negative allometric growth between males and females. The defensive secretion hexane extract was submitted to fractionation using SiO2 open-column chromatography and the gas chromatographic coupled to mass spectrometric analysis was applied in the fraction possibilities to identify major fatty acid methyl esthers, along with minor alkanes, alkenes and fatty acids derivatives and the known quinoids 2-methoxy-3-methylhydroquinone, 2-methoxy-3-methyl-1,4-benzoquinone, 2,3-dimethoxy-1,4-benzoquinone and 2,3-dimethoxyhydroquinone. In addition, the cytochrome oxidase I sequence for the species was deposited for the first time. ecosystems Thus fuscipes Brazil SiO opencolumn open column esthers alkanes 2methoxy3methylhydroquinone, 2methoxy3methylhydroquinone methoxymethylhydroquinone 2 methoxy 3 methylhydroquinone, methylhydroquinone 2-methoxy-3-methylhydroquinone 2methoxy3methyl1,4benzoquinone, 2methoxy3methyl14benzoquinone methoxymethylbenzoquinone 1,4 benzoquinone, 1 4 benzoquinone 2-methoxy-3-methyl-1,4-benzoquinone 2,3dimethoxy1,4benzoquinone 23dimethoxy14benzoquinone dimethoxybenzoquinone 2,3 dimethoxy 2,3dimethoxyhydroquinone. 23dimethoxyhydroquinone dimethoxyhydroquinone dimethoxyhydroquinone. 2,3-dimethoxyhydroquinone addition time 2methoxy3methyl1 4benzoquinone 2methoxy3methyl1,4benzoquinone 14 1, 3dimethoxy1 23 2, 3dimethoxyhydroquinone 2,3dimethoxyhydroquinone methoxymethyl 2methoxy3methyl 3dimethoxy

The phytochemical reinvestigation from the heartwood of the extracts of Cordia glazioviana led to the isolation of four still undescribed hydroquinones derivatives designated as cordiaquinol D (1), cordiaquinol E (2), (10R)-10,11-dihydrofuran-1,4-dihydroxy-globiferin (3) and 2-[(1’E,6’E)-3’,8’- dihydroxy-3’,7’-dimethylocta-1’,6’-dienyl]-benzene-1,4-diol (4), along with the naphthoquinone 6-[(2’R)-2’-hydroxy-3’,6’-dihydro-2H-pyran-5’-yl]-2-methoxy-7-methylnaphthalene-1,4-dione (5). Additionally, six previously known compounds were also isolated: rel-1,4-dihydroxy-8(,11(;9(,11(-diepoxy-2-methoxy-8a(-methyl-5,6,7,8,8a,9,10,10a-octahydro-10-antracenone (6), didehydroconicol (7), 1(,6(-dihydroxy-7-epi-eudesm-3-ene (8), 1(,6(-dihydroxy-7-epi-eudesm-4(15)-ene (9), 10,11-dihydroxybisabolol (10), and hamanasal-A (11). The structures of the new compounds were assigned by high-resolution mass spectrometry (HRMS) and nuclear magnetic resonance (NMR) analyses. The relative stereochemistry of 3, 4, and 5 was improved by quantum mechanical calculations. Eight, out of the eleven isolated compounds (2-9), were tested through cellular viability and lipopolysaccharide (LPS)-induced inflammation assays against RAW 264.7 macrophage-like cells. Compounds 3-5 exhibited a stronger effect on LPS-induced NO production (half-maximal inhibitory concentration (IC50) 50.34, 105.83, and 66.73 µM, respectively).

Abstract Phytochemical studies of Cespedesia spathulata (Ochnaceae) leaves using 1H, 13C NMR, and GC-MS have led to the isolation of some metabolites identified for the first time in these species such as cathechin, epicatechin, vitexin, orientin, 6’’-O-acetyl-vitexin, sitosterol, stigmasterol, phytol, 4,5-dihydrovomifoliol and a mixture of aliphatic methyl esters, together with ochnaflavone, which was previously isolated from this plant. The modulating activity of some fractions and compounds from Cespedesia spathulata towards tyrosinase enzyme was assayed by spectroscopic and theoretical means/experiments. The dichloromethane fraction (133 μg mL-1) and ochnaflavone (333 μM) inhibited tyrosinase activity by 20 % and 2.0 %, respectively, whereas the ethyl acetate fraction (666 μg mL-1) and ±catechins (catechin and epicatechin - 800 μM) activated it by 104 % and 384 %, respectively. Quantum chemical calculations suggested that catechin and epicatechin are better activators than L-DOPA by interacting with Cu (II) ions. Molecular docking results suggested that hydrogen bonding and hydrophobic interactions are the main binding forces between each tyrosinase activator and the amino acid residues inside the active protein binding pocket.

A chemical investigation of Anaxagorea dolichocarpa Sprague & Sandwith, a member of Annonaceae family, was carried out. The ethanolic extract from the roots of this plant led, by chromatography tecniches, to isolation of the new azaphenanthrene alkaloids dolichocarpine (1) and 9-methoxyeupolauramine (2), besides the known alkaloids eupolauramine (3), 3-methoxyeupolauridine (4), eupolauramine (5) and 4-methylsampangine (6). The structures of isolated compounds were established by 1D and 2D NMR, HRESIMS, tandem MSn and IR data. The cytotoxicity of compounds 1 - 5 was evaluated against HCT-116 (human colorectal carcinoma) and L929 (murine fibroblast) cell lines.

Abstract The essential oils obtained by hydrodistillation from fresh leaves of Vitex agnus-castus and Ocimum campechianum, and from fresh inflorescences of Ocimum carnosum were analysed by GC-FID and GC-MS. The major components of V. agnus-castus essential oil were identified as 1,8-cineole (47.9%), terpinyl α-acetate (11.6%), sabinene (11.2%) and caryophyllene oxide (9.7%), while in the O. campechianum essential oil were eugenol (72.1%), β-elemene (6.8%), (E)-caryophyllene (6.4%) and bicyclogermacrene (5.2%). Linalool (79.0%), α-epi-cadinol (5.4%), terpinen-4-ol (3.2%) and 1,8-cineole (2.8%) were the major constituents in the O. carnosum essential oil. The essential oils were subsequently evaluated for their larvicidal and cytotoxic activities. Larval bioassay against Aedes aegypti of V. agnus-castus, O. campechianum and O. carnosum essential oils showed LC50 values of 97.55 ± 0.35, 81.45 ± 0.35 and 109.49 ± 0.35 μg/mL, respectively. The in vitro cytotoxic activities of the essential oils has been evaluated on breast adenocarcinoma (MCF-7), lung carcinoma (NCI-H292), pro-myelocytic leukemia (HL-60), and cervical adenocarcinoma (HEP-2) human cell lines, and pro-myelocytic leukemia cells lines (HL-60) were found to be the most sensitive to all the essential oils tested than the others. This is the first report on larvicidal and cytotoxic activities of these essential oils.

Abstract The chemical study of roots from Azadirachta indica A. Juss., Meliaceae, led to the isolation of two new terpenoids, limonoid morenolide and diterpene 17-hydroxy-sandaracopimar-8,15-dien-11-one, in addition to the four well-known limonoids nimbinene, nimbinal, nimbandiol and salannin, and three diterpenoids nimbidiol, ferruginol, and 6,7-dehydroferruginol. Their structural elucidations were based on one and bidimensional Nuclear Magnetic Resonance and Electrospray ionization mass spectrometry spectra data which was compared to the data found in literature. The anti-inflammatory, cytotoxic and antimycobacterial activities of the identified terpenoids were evaluated.

Abstract: This study evaluated the antibacterial, antifungal, and antioxidant effect of 7-hydroxy-4’,6-dimethoxy-isoflavone and essential oil of Myroxylon peruiferum. The compound was isolated and its structure elucidated by NMR. The chemical composition of essential oil determined by GC-MS analysis. To evaluation of antimicrobial activity, the Minimum Inhibitory Concentration (MIC), Minimum Bactericidal Concentration (MBC) and Minimum Fungicidal Concentration (MFC) were performed. In addition to analysis of antioxidant activity, DPPH radical scavenging tests, iron chelating assay (FIC), antioxidant reducing power assay (FRAP) and β-carotene bleaching assay (BCB) were performed. For the essential oil were identified 24 organized compounds having as main constituents; Germacrene D (17.2%), α-pinene (14.8%) and E-caryophyllene (10.8%). The results showed that isoflavone (2000 to 156 μg/mL) and essential oil (5.0 to 1.25%) present antibacterial and antifungal activity against Gram-positive bacteria and filamentous fungi. The isoflavone and the essential oil also presented antioxidant activity in all the tests, mainly on inhibition of the oxidation of β-carotene test concentrations ranging from 60 to 100%. In conclusion, isoflavone and essential oil from M. peruiferum present an antimicrobial alternative against Gram-positive bacteria, especially of the genus Staphylococcus and dermatophyte fungi of the genus Trichophyton, as well as a natural compound antioxidant.

The secondary metabolites of the aerial parts of Phyllanthus acuminatus Vahl (Phyllanthaceae) and the biological activity of one of them were characterized in this study. This chemical investigation led to isolation of two lignans, luclaricin (1), a new arylnaphtalene-typelignan, and justicidin B (2). The structures of isolated compounds were determined based on 1D and 2D-NMR, HRESIMS and IR. The cytotoxic activity of justicidin B was assessed against tumor cell lines (MCF-7, U251, NCI-ADR/RES, NCI-H460, OVCAR-3, HT29 and K562) and a non-tumor cell line (HaCat) using sulforhodamine B assay. Justicidin B showed strong cytotoxic activity against the tumor cell lines HT29, K562 and U251 with GI50 values of 2.28, 3.29 and 5.76 mol L-1, respectively.

A phytochemical investigation from aerial parts of Casearia arborea (Rich.) Urb. (Salicaceae) led to isolation and identification of: sitosterol, 4-en-stigmast-3-one, 13-hydroxy-trans-ent-cleroda-3,14-diene,3-hydroxy-2-oxo-trans-ent-cleroda-3,14-diene (kolavelone), a mixture of 13-hydroxy-trans-ent-cleroda-3,14-diene and an ester ethyl hexadecanoate, kaempferol-3-O-a-L-arabinofuranoside and 4',5,7-trihydroxy-3',5'-dimethoxyflavone (tricin). The compounds have been described for the first time in this species. Five trihydroxy-flavone-hexoside derivatives have been identified by LC-ESI-HR-MS. The antimicrobial activity of kolavelone was evaluated against strains of Staphylococcus, Bacillus, Pseudomonas, Shigella and Candida spores, and its minimum inhibitory concentration (MIC) was determined. The results showed the antimicrobial activity of kolavelone against several bacteria and Candida tropicalis indicating its potential use as antimicrobial agent.

ABSTRACT The organic extracts from stems, roots and leaves of Tephrosia egregia Sandwith, Fabaceae, provided a new flavone, 5-hydroxy-8-(1",2"-epoxy-3"-hydroxy-3"-methylbutyl)-7-methoxyflavone (1), in addition to eleven known compounds: pongaflavone (2), praecansone B (3), 12a-hydroxyrotenone (4), praecansone A, 2',6'-dimethoxy-4',5'-(2",2"-dimethyl)-pyranochalcone, pongachalcone, maackiain, β-sistosterol and its glucoside, p-cumaric acid and cinnamic acid. The structures of all compounds were established on the basis of spectroscopic methods, mainly 1D and 2D NMR and HRESIMS, involving comparison with literature data. Cytotoxicity of compounds 1–4 was evaluated against AGP-01 (cancerous ascitic fluid), HCT-116 (colon adenocarcinoma), HL-60 (leukemia), PC-3 (prostate carcinoma), SF-295 (glioblastoma) and SKMEL 28 (melanoma) cell lines.

ABSTRACT Harrisia adscendens (Gürke) Britton & Rose is a species of the family Cactaceae found in the northeastern semi-arid and popularly known as foxtail. In folk medicine, the roots of this species are used for the treatment of toothache and heartburn. The objective of this study was to perform the isolation and identification of the secondary metabolites obtained from the vegetal drug by chromatographic and spectroscopic techniques and to evaluate the antimicrobial activity of the extract. The qualitative phytochemical analysis of the extract showed suggestive results for the presence of alkaloids. Two compounds were isolated and identified: 2-methyl-9H-β-carboline-2-ion, a β-carboline alkaloid obtained for the first time as a natural product and 2',6'-dihydroxy-4'-methoxyacetophenone-2'-O-β-glucoside. In the antimicrobial tests, it was possible to observe activity against Pseudomonas aeruginosa. The results obtained by spectroscopic techniques allowed to characterize the phytochemical properties of the vegetal drug and may be useful in future studies for production of herbal medicines.

ABSTRACT Phytochemical investigation of Bauhinia acuruana Moric., Fabaceae, resulted in the isolation of sixteen constituents, including two new compounds 2'-hydroxy-2,3,5-trimethoxybibenzyl (1), (2R,3S)-2-(3,4'-dihydroxyphenyl)-5-methoxy-6-methylchroman-3,7-diol (2), together with fourteen known ones (3–16). The structures of the compounds were established by spectroscopic analysis including HR-ESI-MS, 1D and 2D NMR data, followed by comparison with previously reported data from the literature. Compounds 1, 2, 6, 7, 8 and 9 were evaluated for their cytotoxicity, which turned out to be marginal in a panel of six human cancer cell lines.