Quinone/Hydroquinone Sesquiterpenes

Marcos, Isidro S.; Conde, A.; Moro, Rosalina F.; Basabe, P.; Díez, David; Urones, Julio G.

doi:10.2174/157019310791384128

Cited by 80 publications

(87 citation statements)

References 148 publications

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“…The chemical structure of ilimaquinone contains a benzoquinone moiety, combined with trans-decalin ring system bearing an exocyclic double bond as a rearranged drimane-type sesquiterpene unit (Capon and MacLeod, 1987). Since the initial isolation of ilimaquinone, more than 170 sesquiterpene quinone analogs have been identified, forming a characteristic class of secondary metabolites with abundant structural variants with promising biological activities (Marcos et al, 2010). The first complete synthesis of ilimaquinone and related analogs was accomplished in 1995, and a number of attempts with different approaches have been reported, which reflects the biological significance of this class of compounds.…”

Section: Introductionmentioning

confidence: 99%

Ilimaquinone induces death receptor expression and sensitizes human colon cancer cells to TRAIL-induced apoptosis through activation of ROS-ERK/p38 MAPK–CHOP signaling pathways

Truong

Kim

et al. 2014

Food and Chemical Toxicology

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Section: Introductionmentioning

confidence: 99%

Ilimaquinone induces death receptor expression and sensitizes human colon cancer cells to TRAIL-induced apoptosis through activation of ROS-ERK/p38 MAPK–CHOP signaling pathways

Truong

Kim

et al. 2014

Food and Chemical Toxicology

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“…1 These molecules feature an epoxydon core substituted with isoprenoid units, frequently a C15 farnesyl chain. The biological activities of members of this family are diverse, and differ depending on whether the isoprenoid chain is linear or cyclized.…”

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confidence: 99%

Late-Stage Terpene Cyclization by an Integral Membrane Cyclase in the Biosynthesis of Isoprenoid Epoxycyclohexenone Natural Products

Tang¹,

Cui

et al. 2017

Org. Lett.

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Macrophorins are representative members of isoprenoid epoxycyclohexenones, containing cyclized drimane moieties. We located and characterized the biosynthetic gene cluster of macrophorin from Penicillium terrestris. MacJ encoded by this cluster was characterized to be the first example of membrane-bound type II terpene cyclases catalyzing the cyclization of meroterpenoids via direct protonation of terminal olefinic bond in the acyclic yanuthone. The late-stage functionalization and substrate promiscuity of MacJ make it a potential biocatalyst for synthesizing macrophorin analogs.

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“…2 Ilimaquinone is one of the most well-known sesquiterpene-quinones comprised of sesquiterpene and benzoquinone subunits, 3,4 and its mechanism of action associated with Golgi membrane was reported. 5 As a part of the chemical investigation of marine sponge, a series of cyclospongiaquinones were isolated from Stelospongia conulata.…”

Section: Introductionmentioning

confidence: 99%

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

Lee

Hwang

et al. 2015

Nat Prod Sci

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-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.

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Quinone/Hydroquinone Sesquiterpenes

Cited by 80 publications

References 148 publications

Ilimaquinone induces death receptor expression and sensitizes human colon cancer cells to TRAIL-induced apoptosis through activation of ROS-ERK/p38 MAPK–CHOP signaling pathways

Ilimaquinone induces death receptor expression and sensitizes human colon cancer cells to TRAIL-induced apoptosis through activation of ROS-ERK/p38 MAPK–CHOP signaling pathways

Late-Stage Terpene Cyclization by an Integral Membrane Cyclase in the Biosynthesis of Isoprenoid Epoxycyclohexenone Natural Products

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

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