ChemInform Abstract: Unusual Terpenes with Novel Carbon Skeletons from the West Indian Sea Whip Pseudopterogorgia elisabethae (Octocorallia)

Abstract

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Metabolitos secundarios, letalidad y actividad antimicrobiana de los extractos de tres corales y tres moluscos marinos de Sucre, Venezuela

“…Aunque no se ha informado la presencia de alcaloides en octocorales de los géneros Muricea y Eunicea, la biosíntesis de este tipo de compuestos ha sido comprobada en otros organismos marinos, tal es el caso del alcaloide aceropterina aislado del gorgonio caribeño Pseudopterogorgia acerosa y una variedad de alcaloides bioactivos en moluscos bivalvos, esponjas y tunicados (Rodríguez & Soto 1996, Kuramato et al 2004. La detección de triterpenos y sesquiterpenlactonas en los extractos crudos de los octocorales, se correlaciona con la abundancia de este grupo de terpenoides en octocorales pertenecientes a las indias Occidentales (Coll 1992, Rodríguez 1995, en los que destacan diterpenos y sequiterpenlactonas con características estructurales únicas y actividades biológicas significativas, aislados de los géneros Eunicea y Pseudopterogorgia (Rodríguez et al 1998, Rodríguez & Ramírez 2001, Wei et al 2004, Gazón et al 2005. En lo referente a la biosíntesis de terpenos en moluscos, se han aislado diterpenos diacilglicéridos con importante actividad biológica en Austrodoris kerguelencis (Davies-Coleman & Faulkner 1991), posiblemente utilizados por este organismo como mecanismo de defensa.…”

Efforts toward the Total Synthesis of Elisabethin A

“…The material was used in the next reaction without further purification. 1 H-NMR (400 MHz, CDCl 3 ): δ = 9.83 (s, 1H), 7.38 (d, J = 1.9 Hz, 1H), 7.34 (dd, J = 8.0, 2.0 Hz, 1H), 6.97 (d, J = 8.0 Hz, 1H), 3.85 (s, 3H), 1.32−1.21 (m, 3H), 1.08 (d, J = 7.5 Hz, 18H); 13…”

“…The product was obtained as a dark red oil and directly subjected to following ester hydrolysis without further purification. 1…”

“…The crude oil was purified by flash chromatography (petroleum ether/ethyl acetate, 10:1), and the pure product was obtained as a yellow oil in 89% yield (15.7 g, 50.7 mmol). 1 (E)-Triisopropyl(2-methoxy-3-methyl-4-(penta-2,4-dien-1yloxy)phenoxy)silane (15). A 500 mL three-necked flask was charged with compound 14 (5.0 g, 16 mmol, 1 equiv) in 100 mL of dry THF.…”

“…From the same marine organism, various novel metabolites were isolated, namely, elisabethin B (2), elisabethin C (3), elisabethin D (4), and its corresponding acetate (5) (Figure 2). 1,2 Additionally, P. elisabethae was the source for elisapterosin B (6) and tetracyclic colombiasin A (7). 2,3 Their novel carbon framework paired with the high density of stereochemical information has made these two molecules attractive targets for total synthesis during the past two decades.…”