Bioactive Compounds from a Gorgonian Coral Echinomuricea sp. (Plexauridae)

Abstract

A new labdane-type diterpenoid, echinolabdane A (1), and a new sterol, 6-epi-yonarasterol B (2), were isolated from a gorgonian coral identified as Echinomuricea sp. The structures of metabolites 1 and 2 were elucidated by spectroscopic methods. Echinolabdane A (1) possesses a novel tetracyclic skeleton with an oxepane ring jointed to an α,β-unsaturated-γ-lactone ring by a hemiketal moiety, and this compound is the first labdane-type diterpenoid to be obtained from marine organisms belonging to the phylum Cnidaria. 6-epi-Yonarasterol B (2) is the first steroid derivative to be isolated from gorgonian coral belonging to the genus Echinomuricea, and this compound displayed significant inhibitory effects on the generation of superoxide anions and the release of elastase by human neutrophils.

Anti-Inflammatory Activities of Natural Products Isolated from Soft Corals of Taiwan between 2008 and 2012

“…Compounds 265 , 266 , 271 , 275 , 277 , 278 , 280 , 281 , 283 – 286 , 288 , 290 , 291 , 293 and 319 suppressed LPS-induced expression level of COX-2 in murine macrophage cells (RAW264.7) [ 21 , 74 , 75 , 76 , 77 , 78 , 79 , 80 , 84 ]. At 10 µg/mL, compounds 321 and 322 inhibited the generation of superoxide anion and the release of elastase by activated human neutrophils [ 73 , 85 ].…”

Echinohalimane A, a Bioactive Halimane-Type Diterpenoid from a Formosan Gorgonian Echinomuricea sp. (Plexauridae)

“…In previous studies, two bisabolane-type sesquiterpenoids, (7 S ,10 R )-(+)-10,11-epoxycurcuphenol and (+)-curcuphenol [4]; a labdane-type diterpenoid, echinolabdane A [5]; a clerodane-type diterpenoid, echinoclerodane A [6]; and a steroid analogue, 6- epi -yonarasterol B [5], had been isolated from a Formosan gorgonian coral identified as Echinomuricea sp. (Plexauridae).…”

Natural Product Chemistry of Gorgonian Corals of the Family Plexauridae Distributed in the Indo-Pacific Ocean

“…Two sesquiterpenoids, including new natural product (7 S ,10 R )-(+)-10,11-epoxycurcuphenol ( 28 ) and known metabolite (+)-curcuphenol ( 29 ) [10], along with a new labdane-type diterpenoid, echinolabdane A ( 30 ), a new sterol, 6- epi -yonarasterol B ( 31 ) [11], a new clerodane-type diterpenoid, echinoclerodane A ( 32 ) [12] and a new halimane-type diterpenoid, echinohalimane A ( 33 ) [13], were isolated from the gorgonian coral Echinomuricea sp., collected off the coast of southern Taiwan (Table 6). The structures of metabolites 28 – 33 were elucidated by spectroscopic methods.…”

“…The structures of metabolites 28 – 33 were elucidated by spectroscopic methods. Echinolabdane A ( 30 ) possesses a novel tetracyclic skeleton with an oxepane ring joined to an α,β-unsaturated-γ-lactone ring by a hemiketal moiety [11]. Echinolabdane A ( 30 ), echinoclerodane A ( 32 ) and echinohalimane A ( 33 ) are the first labdane-, clerodane- and halimane-type diterpenoids to be obtained from marine organisms belonging to the phylum Cnidaria, respectively [11,12,13].…”

“…This compound also exhibited weak cytotoxicity toward DLD-1 and CCRF-CEM tumor cells [9]. Steroid 31 displayed significant inhibitory effects on the generation of superoxide anions and the release of elastase by human neutrophils [11]. Clerodane 32 exhibited weak cytotoxicity toward MOLT-4 and HL-60 tumor cells and displayed a significant inhibitory effect on the generation of superoxide anions by human neutrophils [12].…”