New antifeedant bromopyrrole alkaloid from the Caribbean sponge Stylissa caribica.
نویسندگان
چکیده
In this first report on the chemistry of the sponge Stylissa caribica, two known bromopyrrole metabolites and a new compound, N-methyldibromoisophakellin (1), were isolated and identified. The structure of 1 was determined using spectroscopic methods and the computer program COCON. N-Methyldibromoisophakellin (1) was shown to be the only secondary metabolite in Stylissa caribica that, at its natural concentration, is active as a feeding deterrent against a common omnivorous reef fish.
منابع مشابه
Oxocyclostylidol, an intramolecular cyclized oroidin derivative from the marine sponge Stylissa caribica.
Pyrrole-imidazole alkaloids are widely distributed in marine sponges of the orders Halichondrida and Agelasida. Chemical investigation of the Caribbean sponge Stylissa caribica has led to the isolation of the first brominated pyrrole-imidazole alkaloid containing an oxidized pyrrole moiety. The isolation and structure elucidation of oxocyclostylidol (1) are discussed in detail.
متن کاملMonobromoisophakellin, a new bromopyrrole alkaloid from the Caribbean sponge Agelas sp.
A detailed analysis of the chemical constituents of a Caribbean specimen of Agelas sp. was carried out. Four brominated compounds (1-4) were isolated and one of them was identified as a new bromopyrrole metabolite, monobromoisophakellin (1). The structure of 1 was determined using spectroscopic methods. All compounds were tested for their antifeedant activity against the Caribbean reef fish Tha...
متن کاملSventrin, a new bromopyrrole alkaloid from the Caribbean sponge Agelas sventres.
A detailed analysis of the secondary metabolites of a specimen of Agelas sventres was carried out here for the first time. The chemistry of Agelas sponges is dominated by bromopyrrole derivatives. Besides three known bromopyrrole metabolites, a new compound, sventrin (1), was isolated and its structure identified using spectroscopic methods. Sventrin (1) was shown to be a feeding deterrent comp...
متن کاملStructures and Solution Conformational Dynamics of Stylissamides G and H from the Bahamian Sponge Stylissa caribica
Two new peptides, stylissamides G and H, were isolated from extracts of a sample of Stylissa caribica collected in deep waters of the Caribbean Sea. A single sample of S. caribica among a collection of 10 samples that were examined by LC-MS appeared to be a different chemotype from the others in that it lacked the familiar pyrrole-2-aminoimidazole alkaloids, stevensine and oroidin, and containe...
متن کاملDisturbance of voltage-induced cellular calcium entry by marine dimeric and tetrameric pyrrole--imidazole alkaloids.
Twelve brominated pyrrole-imidazole alkaloids from the Caribbean sponges Stylissa caribica and Agelas wiedenmayeri were tested for interactions with cellular calcium homeostasis using PC12 cells. Massadine (half maximal concentration: 5.32 +/- 0.007microM), stylissadines A (4.48 +/- 1.1microM) and B (4.6 +/- 1.6microM) as well as tetrabromostyloguanidine (15.6 +/- 0.004microM) reduced voltage-d...
متن کاملذخیره در منابع من
با ذخیره ی این منبع در منابع من، دسترسی به آن را برای استفاده های بعدی آسان تر کنید
برای دانلود متن کامل این مقاله و بیش از 32 میلیون مقاله دیگر ابتدا ثبت نام کنید
ثبت ناماگر عضو سایت هستید لطفا وارد حساب کاربری خود شوید
ورودعنوان ژورنال:
- Journal of natural products
دوره 64 10 شماره
صفحات -
تاریخ انتشار 2001