109954-48-5Relevant articles and documents
Evaluation of cancer-preventive activity and structure-activity relationships of 3-demethylubiquinone Q2, isolated from the ascidian Aplidium glabrum, and its synthetic analogs
Fedorov, Sergey N.,Radchenko, Oleg S.,Shubina, Larisa K.,Balaneva, Nadezhda N.,Bode, Ann M.,Stonik, Valentin A.,Dong, Zigang
, p. 70 - 81 (2006)
Purpose. 3-Demethylubiquinone Q2 (1) was isolated from the ascidian Aplidium glabrum. The cancer-preventive properties and the structure-activity relationship for 3-demethylubiquinone Q2 (1) and 12 of its synthetic analogs (3-14) are reported. Methods. Compounds 3-14, having one or several di- or triprenyl substitutions and quinone moieties with methoxyls in different positions, were synthesized. The cancer-preventive properties of compounds 1 and 3-14 were tested in JB6 Cl41 mouse skin cells, using a variety of assessments, including the methanethiosulfonate (MTS) assay, flow cytometry, and soft agar assay. Statistical nonparametric methods were used to confirm statistical significance. Results. All quinones tested were shown to inhibit JB6 Cl41 cell transformation, to induce apoptosis, AP-1, and NF-κB activity, and to inhibit p53 activity. The most promising effects were indicated for compounds containing two isoprene units in a side chain and a methoxyl group at the para-position to a polyprenyl substitution. Conclusions. Quinones 1 and 3-14 demonstrated cancer-preventive activity in JB6 Cl41 cells, which may be attributed to the induction of p53-independent apoptosis. These activities depended on the length of side chains and on the positions of the methoxyl groups in the quinone part of the molecule.
Anti-inflammatory and antimalarial meroterpenoids from the New Zealand ascidian aplidium scabellum
Chan, Susanna T. S.,Pearce, A. Norrie,Januario, Ana H.,Page, Michael J.,Kaiser, Marcel,McLaughlin, Rene J.,Harper, Jacquie L.,Webb, Victoria L.,Barker, David,Copp, Brent R.
experimental part, p. 9151 - 9156 (2011/12/16)
Bioassay-directed fractionation of an extract of the New Zealand ascidian Aplidium scabellum has afforded the anti-inflammatory secondary metabolite 2-geranyl-6-methoxy-1,4-hydroquinone-4-sulfate (1) and a family of pseudodimeric meroterpenoids scabellone
Microwave-mediated claisen rearrangement followed by phenol oxidation: A simple route to naturally occurring 1,4-benzoquinones. The first syntheses of verapliquinones A and B and panicein A
Davis, Christopher J.,Hurst, Timothy E.,Jacob, Aouregan M.,Moody, Christopher J.
, p. 4414 - 4422 (2007/10/03)
The naturally occurring 1,4-benzoquinones 2-methoxy-6-propyl-1,4- benzoquinone (1), 2-methoxy-6-pentyl-1,4-benzoquinone (primin 2), 2-methoxy-6-pentadecyl-1,4-benzoquinone (3), 2-methoxy-6-heptadecyl-l,4- benzoquinone (dihydroirisquinone, pallasone B; 4) were synthesized by a simple protocol involving microwave accelerated Claisen rearrangement of allyl ethers 10, followed by hydrogenation of the side chain alkene, and oxidation to the quinone. The Claisen-based methodology was extended to the first synthesis of the marine benzoquinones verapliquinones A and B (5 and 6), and panicein A (7). Isoarnebifuranone (9) was also synthesized by a similar strategy.
