Chemical profile and antimicrobial activity of (L.) R. Br. essential oils.

(L.) R. Br.

New cyclopeptide alkaloid of Condalia buxifolia and the absolute stereochemistry of Condaline A.

During the course of a study of Condalia buxifolia (Rhamnaceae), one new cyclopeptide alkaloid condaline B (1), together with six known cyclopeptide alkaloids, condaline A (2), and the scutianines B (3), - D (4) and -E (5), frangulanine (6), and 3,4,28-tris-epi-scutianene N (7), were isolated from the rind bark of Condalia buxifolia. Their structures have been confirmed through spectroscopic analyses such as 1D and 2D NMR experiments. The absolute stereochemistry of condaline A (2), was elucidated by X-ray crystal structure determination of its HI salt.

antiproliferative activity of alkaloids isolated from A.DC (Apocynaceae).

In this work, four alkaloids from the stem bark of were isolated, namely: voacangine (); ethyl apovincaminate (); affinisine () and voachalotine (). The alkaloids were tested for antiproliferative capacity in eight tumor cell lines: U251 (glioma), MCF-7 (breast), NCI-ADR/RES (drug resistant ovary), 786-0 (kidney), NCI-H460 (lung), HT-29 (colon), K562 (leukemia) and PC-3 (prostate) and a non-tumor keratinocyte cell line (HaCat). Antiproliferative activity was observed after 48 hours and results expressed as the concentration needed to induce 50% growth inhibition (GI50) in µM.

Alkaloids from the stem barks of Scutia buxifolia Reissek (Rhamnaceae): Structures and antimicrobial evaluation.

A reinvestigation of the chemical constituents of the stem barks of Scutia buxifolia, a member of the Rhamnaceae, resulted, along with the known alkaloids scutianine C and scutianene L, in the isolation of three undescribed diastereoisomeric alkaloids - scutianine N, 27-epi-scutianine N and 3, 4, 7-tri-epi-scutianine N -, one undescribed non macrocyclic alkaloid - scutianine Q - and a neutral compound -scutianene M. Their structures were determined using extensive NMR techniques and HRMS. The absolute configurations of the stereogenic centers of the three diastereoisomeric alkaloids have been assigned by gas chromatography employing modified cyclodextrins as chiral stationary phases.

First report on the production of phytotoxic metabolites by under optimized conditions of submerged fermentation.

An alternative to controlling weeds resistant to conventional herbicides is the isolation of new active principles. Fungi can produce phytotoxic metabolites that may be used in the development of new herbicides. The objectives of this study were: (1) isolate, select, and identify a fungus producer of phytotoxic metabolites and (2) optimize the culture conditions of this fungus in a low-cost culture medium, with the aim of increasing the phytotoxic effects of their metabolites in weeds and commercial plants.

essential oil from Brazil: phytochemical composition, genotoxicity, protective effects on and antimycobacterial activity.

(Weinm) DC. essential oil was obtained by hydrodistillation of wild flowers from southern Brazil. We explored, for the first time, the phytochemical composition, toxicity, resistance to oxidative stress in , and antimycobacterial activities of essential oil.

Evaluation of prolyl oligopeptidase and acetylcholinesterase inhibition by Roxb. from Brazil.

Roxb. (Phyllanthaceae) is a plant used in Brazilian folk medicine for the treatment of intestinal infections and diabetes. Despite its use in traditional medicine, it was reported that extract may cause several effects in the central nervous system (CNS) of animals, such as agitation and signs of depression.

Antibacterial activity of Discaria americana Gillies ex Hook (Rhamnaceae).

Ethnopharmacology Relevance: Discaria americana Gillies ex Hook (sin. Discaria febrifuga and Discaria longispina) (Rhamnaceae) is a plant native from Rio Grande do Sul (Southern Brazil), Uruguay and Argentine, and has been used in Brazilian traditional medicine as antipyretic agent, and for stomach disorders. In Rio Grande do Sul, Uruguay and Argentine, the roots, in decoction, are used as tonic and febrifuge.

Chemical constituents from Valeriana polystachya Smith and evaluation of their effects on the acetylcholinesterase and prolyl oligopeptidase activities.

Two new iridoids (1-2) and a new decomposition product of valepotriates (3), together with fifteen known compounds (4-18) were isolated from the roots and rhizomes of Valeriana polystachya Smith, a native species from the Pampa Biome. Their structures were elucidated by means of NMR spectroscopy, mass spectrometry and optical rotation. The structures of 3 and 18 were further confirmed by single crystal X-ray diffraction analysis.

Phytochemical and antimicrobial study of Pilocarpus pennatifolius Lemaire.

The investigation of the crude extract of leaves and bark of Pilocarpus pennatifolius Lemaire allowed isolated of a not yet described coumarin, together with three known coumarins (bergapten, xanthotoxin and dimethyl allyl xanthyletin), and a not yet described imidazole alkaloid. All structures were established by means of spectral analysis, including extensive 2D NMR studies. In addition, the alkaloid had its absolute stereochemistry determined by X-ray diffraction.

Antimicrobial Evaluation of Erythrinan Alkaloids from Erythrina cristagalli L.

Background: Several species of the genus Erythrina have been used as sedative, antidepressant, and anticonvulsant. Erythrina crista-galli is native to the Pampa Biome and is widely used for medicinal purposes. Erythrinan alkaloids exhibit a range of pharmacological properties.

A phytochemical study of the from Southern Brazil: Na,K-ATPase activity inhibition and antioxidant properties.

This study investigated the antioxidant activity of (CG) and its effect on Na, K-ATPase from cardiac muscle The ethanolic extract showed higher antioxidant capacity compared to aqueous and ethyl acetate fraction. Ethyl acetate fraction showed β-sitosterol-3-O-β-glucoside, kaempferol, quercetin, isoquercetin, gallic acid methyl ester, and gallic acid. The ethanolic extract also reduced the Na,K-ATPase activity.

Phytochemical analysis of bark from Helietta apiculata Benth and antimicrobial activities.

Extraction and characterization of natural products from the bark of the trunk of Helietta apiculata Benth (Rutaceae) afforded nine alkaloids, eight furoquinoline and one quinolone, limonine, three cinnamic acid derivatives, three neolignans, tetracosanoic acid, six coumarins, of which apiculin A and apiculin B (neolignans), and tanizin (coumarin) are previously undescribed compounds. The structures of all compounds were determined by spectroscopic methods, and the crystal structures of two of the newly undescribed compounds, apiculin A and apiculin B, were determined by X-ray analysis. Extracts and pure compounds isolated from Helietta apiculata showed promising antimicrobial activities.

Chemical composition and evaluation of prolyl oligopeptidase and acetylcholinesterase inhibitory activities of Leonurus Sibiricus L. from Brazil.

Chemical investigation of the aerial parts of Leonurus sibiricus L. used in Brazilian folk medicine led to the identification of the following constituents: the labdane-type diterpenoid leojaponin, the phytosterols β-sitosterol and β-sitosterol glucoside and the alkaloid leonurine. The crude extracts obtained from methanol and methanol/1% HCl and pure compounds isolated from L.

Lanostane-type triterpenes from the fungal endophyte Scleroderma UFSMSc1 (Persoon) Fries.

Two lanostane triterpenoids (sclerodols A and B) were isolated from the culture of the Eucalyptus grandis derived from the endophyte Scleroderma UFSM Sc1(Persoon) Fries together with three known compounds: one related triterpenoid lanosta-8,23-dien-3β,25-diol, the disaccharide α,β-trehalose, and the sugar alcohol mannitol. Their structures were elucidated on the basis of 2D NMR, HRME, and single-crystal X-ray diffraction data. The methanol crude extract and the isolated lanostane triterpenoids showed promising anticandidal activities.

Chemical Composition and Inhibitory Effects of Hypericum brasiliense and H. connatum on Prolyl Oligopeptidase and Acetylcholinesterase Activities.

Background: The genus Hypericum (family Clusiaceae) comprises various species that are used in traditional medicine, such as wound healing, antidepressant, and anticancer agents.

Objective: The aim of this study was to evaluate the inhibitory capacity of extracts and fractions from two Hypericum species used in the Brazilian folk medicine (H. brasiliense and H.

Structure-activity relationship of benzophenanthridine alkaloids from Zanthoxylum rhoifolium having antimicrobial activity.

Zanthoxylum rhoifolium (Rutaceae) is a plant alkaloid that grows in South America and has been used in Brazilian traditional medicine for the treatment of different health problems. The present study was designed to evaluate the antimicrobial activity of the steam bark crude methanol extract, fractions, and pure alkaloids of Z. rhoifolium.

In vitro evaluation of caffeoyl and cinnamoyl derivatives as potential prolyl oligopeptidase inhibitors.

A screening of the natural product chlorogenic acid, isolated from the Brazilian medicinal plant Hypericum brasiliense, caffeic acid, cinnamic acid, and p-methoxycinnamic acid, and derivatives of caffeoylquinic, caffeoyl, and cinnamoyl against the enzymes prolyl oligopeptidase and dipeptidyl peptidase IV was carried out. Caffeoylquinic, caffeoyl, and cinnamoyl derivatives were prepared using simple derivatization procedures and through coupling reactions with the amino acid proline. The dipeptidyl peptidase IV assay showed inhibitory activity of the tested compounds at a high concentration (500 µM) in the range of 81.

Cyclopeptide alkaloids: stereochemistry and synthesis of the precursors of discarines C and D and myrianthine A.

The stereochemistry of discarines C (1) and D (2) and myrianthine A (3), three cyclopeptide alkaloids isolated from Discaria febrifuga, was determined by a combination of NMR studies of 1-3, enantioselective gas chromatography, and comparison of NMR data with those of synthetic tripeptides. For the synthesis of peptides, the nonproteinogenic amino acid 3-phenylserine was also obtained in its four diastereoisomeric forms (l and d threo, obtained by recrystallization of the diastereoisomeric tripeptide, and l and d erythro, obtained by a Mitsunobu reaction with the threo-tripeptides). The general synthetic strategy described in this paper allows the tripeptide to be obtained with the free N-terminal extremity protected or dimethylated.

Antimicrobial activity of Schinus lentiscifolius (Anacardiaceae).

Ethnopharmacological Relevance: Schinus lentiscifolius Marchand (syn. Schinus weinmannifolius Engl) is a plant native to Rio Grande do Sul (Southern Brazil) and has been used in Brazilian traditional medicine as antiseptic and antimicrobial for the treatment of many different health problems as well as to treat leucorrhea and to assist in ulcer and wound healing. Although it is a plant widely used by the population, there are no studies proving this popular use.

Absolute configuration of franganine.

The absolute configuration of franganine (1), a cyclopeptide alkaloid isolated from the methanol root bark extract of Discaria americana, was established on the basis of detailed NMR spectroscopic data and X-ray diffraction analysis of its salt (2).

Inhibitory effect of verbascoside isolated from Buddleja brasiliensis Jacq. ex Spreng on prolyl oligopeptidase activity.

The phenylpropanoid glycoside verbascoside [2-(3,4-dihydroxyphenylethyl)-1-O-α-L-rhamnopyranosyl-(1→3)-β-D-(4-O-caffeyl)-glucopyranoside] (1) has been isolated as the main constituent of the crude extract of Buddleja brasiliensis Jacq. ex Spreng from Southern Brazil. The crude extract, main fractions and the compound 1 were evaluated for inhibition of the enzymes acetylcholinesterase (AChE), dipeptidyl peptidase-IV (DPP-IV) and prolyl oligopeptidase (POP).

Cyclopeptide alkaloids from Scutia buxifolia Reiss.

Scutianene E (1), 3,4,28-tris-epi-scutiaene E (2), 28-epi-scutianene E (3) and scutianene L (4), four neutral cyclopeptide alkaloids, were isolated from Scutia buxifolia Reiss, together with four known cyclopeptide alkaloids, scutianines B, C, D and E. Scutianenes 1-3 are diastereoisomeric compounds, with 3-hydroxyleucine as a β-hydroxy amino acid unit, which is connected to the styryl fragment via an ether bridge, β-phenylserine, as a common ring-bonded amino acid residue. Attached to the amino group of β-hydroxyamino acid is a side chain [trans-CH=CH-Ph].

Flavonoids with prolyl oligopeptidase inhibitory activity isolated from Scutellaria racemosa Pers.

Prolyl oligopeptidase (POP) is a serine protease highly expressed in the brain that hydrolyses peptide bonds at the carboxyl terminal of prolyl residues. There is evidence that this enzyme participates in several functions of the central nervous system. Scutellaria racemosa Pers demonstrated significant and selective POP inhibition.

Quinolone alkaloids from Waltheria douradinha.

A phytochemical investigation of the stems of Waltheria douradinha resulted in isolation of two 4-quinolone alkaloids, waltherione B and vanessine, along with three known alkaloids, waltherione A, antidesmone and O-methyltembamide. Their structures were elucidated on the basis of their 2D NMR spectroscopic analyses, and from X-ray crystallographic analysis of waltherione A and the O-methyl derivative of waltherione B. Additionally, waltherione B and vanessine, and the O- and N-methyl derivatives of waltherione A and waltherione B, were evaluated for their antimicrobial activities; only vanessine displayed any (weak) antimicrobial activity.