Produtos naturais das esponjas marinhas Aaptos sp., Hymeniacidon aff. heliophila, e do nudibrânquio Doris aff. verrucosa

Abstract

Recebido em 22/6/99; aceito em 21/1/00 NATURAL PRODUCTS FROM THE MARINE SPONGES Aaptos sp. AND Hymeniacidon aff. heliophila, AND FROM THE NUDIBRANCH Doris aff. verrucosa. Herein we describe the isolation of homarine and piridiniumbetaine B from the sponge Aaptos sp. Although homarine has a common occurrence among animals, piridiniumbetaine B was only recently isolated from the marine sponge Agelas dispar. The isolation of piridiniumbetaine B from two taxonomically distant marine sponges corroborate previous assumptions that such betaines should be regarded rather as primary metabolites. We have also isolated (9-[5'-(methylthio)-β-D-xylofuranosyl]adenine (xylosyl-MTA) from the mantle of a nudibranch identified as Doris aff. verrucosa. The occurrence of xylosyl-MTA in the mantle of this animal strongly suggests that it is the same nudibranch species described for the Mediterranean sea. We have been unable to detect any other compound in the mantle extract of D. aff. verrucosa other than xylosil-MTA and sterols. GC-MS analysis of the sterol fraction from the nudibranch and its prey, the sponge Hymeniacidon aff. heliophila, revealed the occurrence of the ubiquitous sterols, cholesterol, brassicasterol, cholestanol, 24-methylcholesterol and 24-ethylcholesterol, as the only common metabolites, therefore precluding any assumption concerning the sequestration of secondary metabolites by the nudibranch from H. aff. heliophila. Juntamente com os moluscos tectibrânquios, os moluscos nudibrânquios pertencem à sub-Ordem Opistobranchia, que engloba moluscos que não apresentam concha externa ou que possuem uma concha interna de tamanho pequeno, a qual, presume-se, seja um resquício adaptativo. 4 Por não possuírem conchas (defesa mecânica), presume-se que os moluscos Opistobrânquios desenvolveram a capacidade de sintetizar e/ou de acumular substâncias que atuam como defesas químicas 4-7 . Moluscos nudibrânquios são geralmente sequestradores de produtos naturais provenientes de suas presas (esponjas, ascídias, briozoários, algas, cnidários ou outros moluscos). Todavia, em alguns casos demonstrou-se a capacidade de determinadas espécies de nudibrânquios de biossintetizarem de novo várias substâncias isoladas de suas glândulas digestivas ou de seu manto [8][9][10][11] . Por concentrarem quantidades apreciáveis destes compostos orgânicos para sua defesa, os moluscos opistobrân-quios constituem uma fonte importante de produtos naturais com atividades biológicas. KeywordsEntre

Antibiotic, cytotoxic and enzyme inhibitory activity of crude extracts from Brazilian marine invertebrates

“…Our results indicate that four out of nine samples of sponges belonging to the genus Aaptos present biologically active compounds. Marine sponges belonging to the genus Aaptos are known as producers of 1H-benzo- [de][1,6]-naphtyridine alkaloids, a group of compounds which display several biological activities (Granato et al, 2000;Nakamura et al, 1982;Nakamura et al, 1987;Rudi and Kashman, 1993;Tinto, 1998;Longley et al, 1993;Shen et al, 1999;Coutinho et al, 2002;Takamatsu et al, 2003), and, therefore, compounds related to the aaptamines may be present in the samples of marine sponges herein investigated. Among them, the sponge sample Aaptos BA99-52 showed good antibacterial activity activity against oxacilin resistant S. aureus strain # 35.…”

Checklist de Porifera do Estado de São Paulo, Brasil

“…Aaptos sp. Granato et al (2000), Rangel et al (2001), Muricy & Hajdu (2006), Seleghim et al (2007) Canal de São Sebastião 1-15…”

Aplysfistularine: a novel dibromotyrosine derivative isolated from Aplysina fistularis

“…[4][5][6][7][8][9][10] Marine sponges are a prolific source of a huge variety of secondary metabolites. [11][12][13][14][15] Sponges of the order Verongida, and the family Aplysinidae, characterized by the absence of terpenes and the production of steroids, produce a wide diversity of bromotyrosine-containing metabolites with interesting biological properties. 16 The richest sources of biogenetically, tyrosine--derived bromo-containing amines, are members of the Verongida order, and the genus Aplysina.…”