Rapid assessment of chemical compounds from Phyllogorgia dilatata using Raman spectroscopy

Abstract The gorgonian Phyllogorgia dilatata is endemic to the Brazilian coast which is listed as threatened with extinction. This species is known to produce sterols, mono- to tetra-terpenes, conjugated polyenals and peptides. The main objective of this study is to present an alternative method for identification of different classes of compounds based upon a Raman mapping technique using FT-Raman spectroscopy. The Raman analysis performed directly on the tissues (in situ) revealed the occurrence of peridinin, diadinoxanthin, conjugated polyenal and linoleic acid, that were also confirmed by Raman analysis of partitioned crude extracts. We have demonstrated that the technique has potential for use in guiding chromatographic separations and in providing information with respect to the early stages of a tissue necrosis through “purpling”. It may become a valuable non-destructive technique for monitoring the accumulation or production of metabolites during a biological interaction.

A microbial community analysis of the octocoral Eunicea fusca

While there is a significant and growing body of knowledge describing the microbial communities of marine invertebrates such as sponges, there are very few such studies focused on octocorals. The octocoral Eunicea fusca is common on reefs in various regions of the Caribbean and has been the subject of natural product investigations. As part of an effort to describe the microbial community associated with octocorals, a culture-independent analysis of the bacterial community of E. fusca was conducted. Specifically, a 16S rDNA clone library analysis was performed to provide baseline data. A total of 40 bacteria members from 11 groups were found. In general, Proteobacteria were the dominant group with a total of 24 species and α-Proteobacteria represented the highest percentage of bacteria associated with E. fusca (27.5 percent). Other prominent groups observed were Acidobacteria, Actinobacteria, Cyanobacteria, Planctomycetes, delta-Proteobacteria, Lentisphaerae and Nitrospirae. This is the first analysis of bacterial populations associated with the gorgonian E. fusca.

Antiherpes screening of marine organisms from Colombian Caribbean Sea

The exploration of marine environment represents a promising strategy in the search for new active antiviral compounds. The isolation and characterization of the nucleosides spongothymidine and spongouridine from the sponge Cryptotethia crypta used as models for the synthesis of ara-A (vidarabine), that has been used therapeutically against herpetic encephalitis, was the most important contribution since the late 1970s. This paper describes the in vitro antiviral evaluation of 26 organic extracts obtained from eleven octocoral species and fifteen marine sponges. Cytotoxicity was evaluated on Vero cells by MTT assay and the antiviral activity was tested against Herpes Simplex Virus type 1 (HSV-1, KOS strain) by plaque number reduction assay. Results were expressed as 50 percent cytotoxic (CC50) and 50 percent inhibitory (IC50) concentrations, respectively, in order to calculate the selectivity index (SI= CC50/IC50) of each extract. Among the tested marine octocoral species, only three extracts showed antiviral activity, but with low selectivity indices (<3.0). Among the tested marine sponges, eight extracts showed SI values higher than 2.0, and three can be considered promising (Aka cachacrouense, Niphates erecta and Dragmacidon reticulatum) with SI values of 5.0, 8.0 and 11.7, respectively, meriting complementary studies in order to identify the bioactive components of these sponge extracts, which are in course now.

Aislamiento y caracterización estructural de un nuevo triterpeno del octocoral Plexaura Flexuosa Lamoroux. / Isolation and structural caracterization of a new triterpene from the octocoral Plexaura Flexuosa Lamoroux / Isolamento e caracterização estrutural de um novo triterpeno do octocoral Plexaura Flexuosa Lamoroux.

Estudios previos de productos naturales de origen marino han demostrado que los octocorales producen una variedad de metabolitos con diversas estructuras químicas y bioactividades. Con el objetivo de estudiar al octocoral Plexaura flexuosa Lamoroux se analizó el extracto en acetona de un ejemplar colectado en la Bahía de Mochima, estado Sucre, Venezuela. Se evaluaron las propiedades antibacteriana, antifúngica y tóxica del extracto, revelándose una marcada actividad antibacteriana contra las bacterias Gram positiva Staphylococcus aureus y Bacillus cereus, así como una letalidad significativa mediante el bioensayo de Artemia salina. La fracción soluble en hexano de dicho extracto exhibió actividad antifúngica contra Candida albicans y Trichosporum sp. A partir de dicha fracción se aisló un sólido blanquecino, usando sucesivas cromatografías de columna eluidas con mezclas de hexano:AcOEt en diferentes proporciones. El compuesto se cristalizó con AcOEt, obteniéndose cristales blancos en forma de agujas con punto de fusión de 194,8-195,0°C. Para la identificación estructural de este sólido se realizaron análisis espectroscópicos (IR, RMN¹H, RMN13C, HMQC, HMBC y COSY¹H-¹H), los cuales evidenciaron la presencia de un esqueleto triterpenoidal tetracíclico con cadena lateral, ocho metilos, un doble enlace trisustituído y un grupo epóxido exocíclico. El análisis sistemático de los datos espectrales y su posterior comparación con estructuras reportadas permitieron establecer la estructura posible del compuesto como un derivado 3,5-epoxi del dinosterol.

Previous studies of natural products of marine origin have showen that octocorals produce a variety of metabolites with diverse chemical structures and significant bioactivities. The acetone extract of the octocoral Plexaura flexuosa Lamoroux collected at Mochima Bay, Sucre state, Venezuela, was analyzed and evaluated for its antibacterial, antifungal and toxic properties, showing a significant antibacterial activity against the Gram positive bacteria Staphylococcus aureus and Bacillus cereus, and also a significant lethality in the Artemia salina bioassay. The hexane-soluble fraction of this extract exhibited antifungal activity against Candida albicans and Trichosporum sp. A white solid was isolated from this fraction by successive column chromatography with different proportions of hexane:EtOAc mixtures as eluting solvents. The compound was crystallized with EtOAc, forming needle-shaped white crystals with a melting point of 194.8-195.0°C. Subsequently, spectroscopy analyses were performed for the structural identification of this solid, employing IR, ¹HNMR, 13CNMR, HMQC, HMBC and ¹H-¹HCOSY, which revealed the presence of tetra-cyclical triterpene skeleton with a side chain, eight methyl groups, a trisubstituted double bond and an exocyclical epoxy group. Spectral data analysis and comparison with reported structures permitted the establishment of a of 3.5-epoxy dinosterol derivative as the possible structure of the compound.

Estudos prévios de produtos naturais de origem marinho têm demonstrado que os octocorais produzem uma variedade de metabolitos com diversas estruturas químicas e bioatividades. Com o objetivo de estudar ao octocoral Plexaura flexuosa Lamoroux se analisou o extrato em acetona de um exemplar recolhido na Bahia de Mochima, estado Sucre, Venezuela. Avaliaram-se as propriedades antibacteriana, antifúngica e tóxica do extrato, revelando-se uma marcada atividade antibacteriana contra as bactérias Gram positiva Staphylococcus aureus e Bacillus cereus, assim como uma letalidade significativa mediante o bioensaio de Artêmia salina. A fração solúvel em hexano de dito extrato exibiu atividade antifúngica contra Candida albicans e Trichosporum sp. A partir de dita fração se isolou um sólido branco, usando sucessivas cromatografias de coluna eluídas com misturas de hexano: AcOEt em diferentes proporções. O composto se cristalizou com AcOEt, obtendo-se cristais brancos em forma de agulhas com ponto de fusão de 194,8 - 195,0°C. Para a identificação estrutural de este sólido se realizaram análises espectroscópicas (IR, RMN¹H, RMN13C, HMQC, HMBC e COSY¹H-¹H), as quais evidenciaram a presença de um esqueleto triterpenoide tetracíclico com cadeia lateral, oito metilos, um duplo enlace trisubstituído e um grupo epóxido exocíclico. A análise sistemática dos dados espectrais e sua posterior comparação com estruturas relatadas permitiram estabelecer a estrutura possível do composto como um derivado 3,5-epóxi do dinosterol.