Briavioids A–C, discovery of new polyacetoxybriaranes from octocoral Briareum violaceum (Quoy & Gaimard, 1833)

Briavioids E–G, Newly Isolated Briarane-Diterpenoids from a Cultured Octocoral Briareum violaceum

“…Briavioid A ( 9 ) was reported in our previous publication [ 12 ]. Its relative stereochemistry was established through a combination of the NOESY experiment and a single-crystal X-ray diffraction analysis with a molybdenum radiation (Mo Kα, λ = 0.71073 Å) source.…”

“…However, the configuration obtained from the X-ray analysis with Mo Kα could only be considered absolute when the structure contained at least one heavy atom. Thus, in order to determine the absolute configuration of this compound, the material of briavioid A ( 9 ) obtained in previous publication [ 12 ] was recrystallized, and the diffraction experiment was carried out using a diffractometer equipped with Cu Kα (λ = 1.54178 Å) radiation source (Flack parameter x = 0.01(5)). An Oak Ridge Thermal-Ellipsoid Plot (ORTEP) diagram ( Figure 8 ) showed the absolute configurations of the stereogenic carbons of 9 to be (1 R ,2 R ,3 S ,4 R ,7 S ,8 S ,9 S ,10 S ,11 R ,12 S ,14 S ,17 R ).…”

“…The detailed extraction procedures for the crude extract and the ethyl acetate extract used in this study are described in our previous publication [ 12 ]. The EtOAc extract (31.2 g) was applied to a silica gel open column and eluted with gradients of hexanes/EtOAc (100% hexanes~100% ethyl acetate, stepwise), resulting in 11 fractions (fractions A–K).…”

“…We reported herein the isolation and structural determination of all isolates, as well as the anti-inflammatory profile of compounds 1 , 2 and 4 – 8 using an in vitro assay to screen the reducing ability of these compounds against iNOS and COX-2 protein expression. In addition, the absolute configuration of briavioid A ( 9 ) [ 12 ] ( Figure 1 ), obtained in previous study, was further reported for its absolute stereochemistry using a single-crystal X-ray diffraction analysis with a diffractometer equipped with a copper radiation (Cu Kα) source.…”

Towards Sustainable Medicinal Resources through Marine Soft Coral Aquaculture: Insights into the Chemical Diversity and the Biological Potential

“…In a recent study on the chemical constituents of the cultured soft coral Briareum violaceum , three new polyacetoxybriarane diterpenoids, briavioids A-C ( 166 – 168 ), as well as two known analogues, briaexcavatin M ( 111 ) and excavatolide F ( 169 ), were isolated. The structure of briavioid A ( 166 ) was fully confirmed by single-crystal X-ray diffraction analysis [ 65 ] ( Figure 11 ).…”