Exploring Chemical Diversity of Phorbas Sponges as a Source of Novel Lead Compounds in Drug Discovery.

Porifera, commonly referred to as marine sponges, are acknowledged as major producers of marine natural products (MNPs). Sponges of the genus Phorbas have attracted much attention over the years. They are widespread in all continents, and several structurally unique compounds have been identified from this species. Terpenes, mainly sesterterpenoids, are the major secondary metabolites isolated from Phorbas species, even though several alkaloids and steroids have also been reported. Many of these compounds have presented interesting biological activities. Particularly, Phorbas sponges have been demonstrated to be a source of cytotoxic metabolites. In addition, MNPs exhibiting cytostatic, antimicrobial, and anti-inflammatory activities have been isolated and structurally characterized. This review provides an overview of almost 130 secondary metabolites from Phorbas sponges and their biological activities, and it covers the literature since the first study published in 1993 until November 2021, including approximately 60 records. The synthetic routes to the most interesting compounds are briefly outlined.

Antitrypanosomal Acetylene Fatty Acid Derivatives from the Seeds of Porcelia macrocarpa (Annonaceae).

Chagas' disease is caused by a parasitic protozoan and affects the poorest population in the world, causing high mortality and morbidity. As a result of the toxicity and long duration of current treatments, the discovery of novel and more efficacious drugs is crucial. In this work, the hexane extract from seeds of Porcelia macrocarpa R.E. Fries (Annonaceae) displayed in vitro antitrypanosomal activity against trypomastigote forms of T. cruzi by the colorimetric MTT assay (IC50 of 65.44 µg/mL). Using chromatographic fractionation over SiO2, this extract afforded a fraction composed by one active compound (IC50 of 10.70 µg/mL), which was chemically characterized as 12,14-octadecadiynoic acid (macrocarpic acid). Additionally, two new inactive acetylene compounds (α,α'-dimacro-carpoyl-ß-oleylglycerol and α-macrocarpoyl-α'-oleylglycerol) were also isolated from the hexane extract. The complete characterization of the isolated compounds was performed by analysis of NMR and MS data as well as preparation of derivatives.

Chemical and biological evaluation of essential oils from two species of Myrtaceae - Eugenia uniflora L. and Plinia trunciflora (O. Berg) Kausel.

The chemical composition and antimicrobial activity of essential oils obtained from leaves of two Myrtaceae species-Eugenia uniflora L. and Plinia trunciflora (O. Berg) Kausel-were determined. Analysis by GC/MS as well as determination of Kovatz indexes indicated atractylone (26.78%) and curzerene (17.96%) as major constituents of E. uniflora oil and α-cadinol (19.15%), apiole (11.15%) and cubenol (5.43%) as main components in P. trunciflora oil. Both essential oils were tested for antimicrobial activity against yeasts and bacteria. E. uniflora and P. trunciflora essential oils were active towards two Gram-positive bacteria, Streptococcus equi and Staphylococcus epidermis. In addition, biological activity of both essential oils was detected for pathogenic yeasts of the genus Candida and Cryptococcus. E. uniflora was active towards all yeast tested and exhibited interesting minimal inhibitory concentrations (0.11 to 3.75 mg/mL) across a broad spectrum of activity.

Variação dos teores de constituintes voláteis de Cymbopogon citratus (DC) Staf, Poaceae, coletados em diferentes regiões do Estado de São Paulo / Variation in the amounts of volatile constituents of Cymbopogon citratus (DC) Staf, Poaceae, collected in different regions of São Paulo State

O óleo essencial extraído de Cymbopogon citratus (DC) Staf, Poaceae, é rico em citral sendo amplamente empregado na indústria química e farmacêutica. Os objetivos desse estudo foram avaliar o conteúdo de citral entre populações de C. citratus coletados em duas regiões diferentes (Ibiúna e Pindamonhangaba, Estado de São Paulo). O óleo essencial extraído de uma população cultivada em Pindamonhangaba-SP apresentou uma concentração alta de citral (aproximadamente 96,0 por cento), enquanto que o óleo extraído da população de Ibiúna-SP apresentou, além de citral, proporções elevadas de outro monoterpeno, o geraniol. Adicionalmente, os óleos essenciais obtidos desta população de C. citratus foram extraídos e analisados ao longo de 24 h (a cada 3 h), sendo que o teor de citral foi maior no período da noite, o que mostra a importância de estudos que avaliam as diferenças químicas associadas às mudanças circadianas. Os componentes dos óleos essenciais foram identificados por RMN de 13C, CG/EM e CG através do índice de Kovats.

The essential oil extracted from Cymbopogon citratus (DC) Staf, Poaceae, is rich in citral and has many applications in chemical and pharmaceutical industry. The aims of this study were evaluate the amount of citral in populations of C. citratus collected in two different regions (Ibiúna and Pindamonhangaba, São Paulo State). The essential oil extracted of a cultivated population in Pidamonhangaba-SP, showed a high content of citral (approximately 96.0 percent), while the essential oil from Ibiuna-SP, showed citral and high amounts of another monoterpene, geraniol. Additionally, the essential oils from this population of C. citratus were extracted and analyzed during 24 h (each 3 h), being the major concentration of citral in the night period, indicating that studies which evaluated the chemical differences associated to circadian changes. The components of essential oils were identified through 13C NMR, GC/MS, GC and Kovat's index.