Pyrrolactams from Marine Sponge <i>Stylissa massa</i> Collected from Myanmar and Their Anti-Vpr Activities

Abstract

A new brominated pyrrolactam stylissaol A (1) together with four known analogues, 2-bromoaldisine, aldisine, spongiacidin D, and Z-hymenialdisine, were isolated from the EtOAc extract of marine sponge Stylissa massa collected in Myanmar. The absolute configuration at C-10 of 1 was determined as R by the electronic circular dichroism (ECD) data. Among the isolated compounds, 2-bromoaldisine showed anti-Viral Protein R (Vpr) activity against TREx-HeLa-Vpr cells with an effective dose of 10 µM and its potency was comparable to that of positive control damnacanthal.

Marine natural products

“…437 Sponges of the genera Stylissa and Astroclera were the sources of stylissaol A 1023 and dimer N(1)-methylisoageliferin 1024, respectively. 438,439 Bromotyrosine-derived alkaloids were reported from a Greek Aplysina 1025-1028, Vietnamese Ecionemia acervus 1029 and an Egyptian Pseudoceratina arabica 1030, respectively. 421,440,441 Bromotyrosines are also commonly encountered in Suberea sponges.…”

A Survey of Recently Discovered Naturally Occurring Organohalogen Compounds

“…13 The red alga Rhodomela confervoides from China contains the four new ureidobromophenols 21−24. 14 An examination of the red alga Vertebrata lanosa, which is commonly found on the coastlines of Europe and North America, finds 23 related metabolites, including the new 3,5dibromotyrosine (25) and 26−30. Sulfonium lanosol 30 is a unique dimethyl sulfonium metabolite.…”

“…The new tryptophan-derived alkaloid, thorectandrin A ( 58 ) was identified in the Southern Australian sponge Thorectandra choanoides . Together with three known analogues, the new pyrrolactam stylissaol ( 59 ) is present in the Myanmar sponge Stylissa massa …”

“…24 Together with three known analogues, the new pyrrolactam stylissaol (59) is present in the Myanmar sponge Stylissa massa. 25 A collection of the Bahamian sponge Aiolochroia crassa (previously, Pseudoceratina crassa) led to the discovery of nine new bromotyrosine alkaloids. These are debromoianthelline (60), pseudoceratinic acid (61), methyl pseudoceratinate (62), 13-oxo-ianthelline (63) Two other rare alkaloids are ma'edamines E (75) and F (76), which embrace a 1,2,3,5-tetrasubstituted pyridinium moiety and are found in Suberea sp.…”