Rogiolol Acetate: A Novel β‐Chamigrene‐Type Sesquiterpene Isolated from a Marine Sponge
Graziano Guella, Ines Mancini, Giuseppe Chiasera, Francesco Pietra
Abstract
Graziano Guella, Ines Mancini, Giuseppe Chiasera, Francesco Pietra
Abstract
Abstract The marine sponge Spongia zimocca SCHMIDT, 1862, collected in front of the torrent II Rogiolo, south of Livorno, contains the sesquiterpene rogiolol acetate (= (+)‐(2R,3S,6R,8R,9R)‐2,8‐dibromo‐9‐chloro‐1,1,9‐trimethyl‐5‐methylidenespiro[5.5]undec‐3‐yl acetate; (+)‐3a), which represents the first chamigrane isolated from a sponge. Although compounds of this class are common in red seaweeds of the genus Laurencia, and our sponge actually contains 9‐bromochamigrene and a variety of other metabolites of nearby growing Laurencia sp., (+)‐3a is unique to our sponge.
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Abstract The marine sponge Spongia zimocca SCHMIDT, 1862, collected in front of the torrent II Rogiolo, south of Livorno, contains the sesquiterpene rogiolol acetate (= (+)‐(2R,3S,6R,8R,9R)‐2,8‐dibromo‐9‐chloro‐1,1,9‐trimethyl‐5‐methylidenespiro[5.5]undec‐3‐yl acetate; (+)‐3a), which represents the first chamigrane isolated from a sponge. Although compounds of this class are common in red seaweeds of the genus Laurencia, and our sponge actually contains 9‐bromochamigrene and a variety of other metabolites of nearby growing Laurencia sp., (+)‐3a is unique to our sponge.
Key concepts: Sponge, Sesquiterpene, Chemistry, Laurencia, Stereochemistry, Genus, Terpenoid, Botany