Clerodane Diterpenes from the Marine Sponge Raspailia bouryesnaultae Collected in South Brazil
| Autor: | Fernanda Nienkötter Sardá, João Luís Carraro, Cláudia Maria Oliveira Simões, Louis P. Sandjo, Eloir Paulo Schenkel, Eliane de Oliveira Tabalipa, Cintia Lhullier, Naira Fernanda Zanchett Schneider |
|---|---|
| Jazyk: | angličtina |
| Rok vydání: | 2019 |
| Předmět: |
0106 biological sciences
Magnetic Resonance Spectroscopy viruses Pharmaceutical Science Herpesvirus 1 Human medicine.disease_cause Virus Replication 01 natural sciences sponge chemistry.chemical_compound Drug Discovery Moiety Pharmacology Toxicology and Pharmaceutics (miscellaneous) lcsh:QH301-705.5 0303 health sciences biology Molecular Structure Chemistry antiproliferative effects Stereoisomerism Nuclear magnetic resonance spectroscopy Porifera Raspailia bouryesnaultae clerodane diterpenes Brazil Stereochemistry Antineoplastic Agents Antiviral Agents Article Diterpenes Clerodane 03 medical and health sciences Inhibitory Concentration 50 anti-herpes activity Decalin 010608 biotechnology medicine Animals Humans IC50 030304 developmental biology Cell Proliferation biology.organism_classification In vitro Sponge Herpes simplex virus lcsh:Biology (General) A549 Cells Diterpene Drug Screening Assays Antitumor |
| Zdroj: | Marine Drugs, Vol 17, Iss 1, p 57 (2019) Marine Drugs Volume 17 Issue 1 |
| ISSN: | 1660-3397 |
| Popis: | The marine sponge Raspailia bouryesnaultae, collected in South Brazil, was selected for detailed investigation considering the results of a screening that pointed to an in vitro antiproliferative effect against non-small cells of human lung cancer (A549) and anti-herpes activity against Herpes Simplex virus type 1 (KOS and 29R strains) of ethanolic extracts. The fractionation and chemical investigation of the sponge&rsquo s hexanic fraction led to the isolation and structural elucidation of six clerodane diterpenes. The main component was identified as the already-reported raspailol (1), isolated from a sponge of the same genus collected in New Zealand. The structure of a new diterpene (2) with a rearranged skeleton was established by high-resolution mass spectrometry (HRMS) and 1D and 2D Nuclear magnetic resonance spectroscopy (NMR) experiments, and named here as raspadiene. Furthermore, four diterpenes were elucidated as isomers of clerodane diterpenes previously obtained from plants, namely kerlinic acid (3), kerlinic acid methyl ester (4), annonene (5), and 6-hydroxyannonene (6). They differ in their stereochemistry, since these diterpenes are characterized by a trans ring fusion at the decalin moiety and the relative configuration of the two methyl groups at C-8 and C-9 in a cis relationship (type trans/cis). The Raspailia diterpenes have a cis ring fusion at the decalin moiety, and the two methyl groups at C-8 and C-9 are in a trans relationship (type cis/trans). The isolated compounds were evaluated for their potential antiproliferative effects on human cancer cell line A549, and it was observed that the diterpenes bearing a hydroxyl group at C-6 exhibited moderate cytotoxic activity, with 50% inhibitory concentration (IC50) values lower than 25 &mu M. The evaluation of the potential anti-herpes activity against Herpes Simplex Virus type 1 (HSV-1, KOS and 29R strains) showed that the more promising results were observed for the new compound 2, since it inhibited HSV-1 (KOS and 29R strains) replication by 83% and 74%, respectively. |
| Databáze: | OpenAIRE |
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