Chemistry and Bioactivity of Briaranes from the South China Sea Gorgonian Dichotella gemmacea

Abstract

Seven new briarane diterpenoids, gemmacolides AZ–BF (1–7), were isolated together with eight known analogues (8–15) from the South China gorgonian Dichotella gemmacea. Their structures were elucidated based on detailed spectroscopic analysis and a comparison with reported data. In an in vitro bioassay, these compounds exhibited different levels of growth inhibition activity against A549 and MG63 cells, giving continuous evidences about the biological contribution of functional groups at C-2, C-12, C-13, and C-16. These compounds were also evaluated for their antibacterial and antifungal activities. Compound 8 exhibited a potential antibacterial activity against both Gram-positive bacterium Bacillus megaterium and Gram-negative bacterium Escherichia coli.

Chemical and biological aspects of octocorals from the Brazilian coast

“…Species of this family are characterized by the presence of sclerites, consisting of double heads and spindles or rods (Cairns, 2007). For the soft corals of the family Ellisellidae, mainly briarane-type diterpenoids were reported, such as gemmacolide A (29), and polyoxygenated steroids such as suberoretisteroid A (30) from Verrucella umbraculum and glycosides of steroids such as Junceelloside C (31) from Dichotella gemmacea (Jiang et al, 2013;Sun et al, 2010;Li et al, 2013a). Five species of this family are found in Brazil.…”

Marine natural products

“…), and gemmacolides AZ-BF 1133-1139 from Dichotella gemmacea. 626 Briarenolides M, P, S, T, ZII and ZVI were found to inhibit production of the pro-inammatory inducible nitric oxide synthase (iNOS), briarenolides N, P and T inhibited the product of COX-2 in LPS-stimulated macrophage cells, and the gemmacolides exhibited low to no cytotoxicity towards two HTCLs and moderate antibacterial activity. The remaining eight diterpenes, all eunicellins, included klymollins Y 1140 and Z 1141 and klyxumollins A-D 1142-1145 (Klyxum molle), 627 and cladieunicellins R 1146 and S 1147 (Cladiella tuberculosa).…”

Briarane Diterpenoids Isolated from Octocorals between 2014 and 2016

“…In addition, seven new briaranes, gemmacolides AZ–BF ( 41 – 47 ) ( Figure 6 ), and eight known analogues, dichotellides M and O [ 23 ], gemmacolide C [ 44 ], juncins P [ 45 ] and ZI [ 46 ], junceellolides D [ 25 ] and K [ 37 ], and (−)-4-deacetyljunceellolide D [ 30 ], were obtained from D. gemmacea , collected from the South China Sea [ 47 ]. The structures of new briaranes 41–47 were determined by spectroscopic methods.…”