Anti-inflammatory Effect of Dactyloquinone B and Cyclospongiaquinone-1 Mixture in RAW264.7 Macrophage and ICR Mice

Abstract

-Sesquiterpene-quinone is a class of secondary metabolites frequently encountered from marine sponge. The present study was designed to examine the anti-inflammatory action of sponge-derived dactyloquinone B (DQB) and cyclospongiaquinone-1 (CSQ1) mixture using lipopolysaccharide (LPS)-induced inflammatory responses. We measured the production of nitric oxide (NO), tumor necrosis factor-alpha (TNF-α), interleukin-1β (IL-1β), and interleukin-6 (IL-6) and expression of inducible nitric oxide synthase (iNOS) and cyclooxygenase-2 (COX-2) protein. TNF-α, IL-1β, and IL-6 production, which increased by treatment with LPS, were significantly inhibited by DQB and CSQ1 mixture. It also decreased the production of NO production, and iNOS and COX-2 expression. Furthermore, it reduced 12-O-tetradecanoylphorbol 13-acetate (TPA)-induced ear edema of ICR mice. These results demonstrate that sesquiterpene-quinone, DQB and CSQ1 mixture, might serve as a chemical pipeline for the development of anti-inflammatory agent.

Alkaloids fromPiper nigrumExhibit Antiinflammatory Activity via Activating the Nrf2/HO­1 Pathway

“…RAW264.7 cells or bone marrow-derived macrophages were seeded in 24-well plates at a density of 5 × 10 5 cells/well. The plates were pretreated with various concentrations of the test compounds for 30 min and then incubated for a further 24 h the presence or absence of 1 μg/mL lipopolysaccharide (LPS) (Lee et al, 2015a). Tin protoporphyrin (SnPP) or copper protoporphyrin (CuPP) was added to the plates along with the test compounds.…”

Bio-inspired construction of a tetracyclic ring system with an avarane skeleton: total synthesis of dactyloquinone A

“…18 An inseparable mixture of aureol B Δ 3,4 (44), 5-epi-aureol B Δ 3,4 (43), and 5-epi-aureol B (27) (0.6 : 3 : 1) was obtained by column chromatography on silica gel in 60% yield. Dactyloquinone A, dactyloquinone A Δ 3,4 , and dactyloquinone B Δ 3,4 (1 : 7 : 1) were synthesized in 17% overall yield, as shown in Scheme 5. Dactyloquinone A (2) and dactyloquinone A Δ 3,4 (49) were inseparable mixtures after HPLC purification.…”

“…Dactyloquinone A, dactyloquinone A Δ 3,4 , and dactyloquinone B Δ 3,4 (1 : 7 : 1) were synthesized in 17% overall yield, as shown in Scheme 5. Dactyloquinone A (2) and dactyloquinone A Δ 3,4 (49) were inseparable mixtures after HPLC purification.…”

“…Dactyloquinone A and its congeners were first synthesized by this key strategy. These congeners include dactyloquinone A Δ 3,4 , dactyloquinone B Δ 3,4 , aureole B Δ 3,4 , 5-epi-aureole B and 5-epi-aureole B Δ 3,4 . The developed biomimetic strategy could potentially be used for the total synthesis of other members of this family of natural products.…”

“…These natural products were all isolated from marine sponges and exhibit diverse biological activities, including antibacterial and inhibitory activities against Na + /K + -ATPase. [2][3][4] The synthesis of avarane sesquiterpenes has been a hot topic because of their unique structure and remarkable biological activity. 5,6 A tricyclic ring system with avarane skeletons was constructed from a Wieland-Miescher ketone derivative (7, Scheme 1a), as depicted in Scheme 1.…”