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Orthidines A–E, tubastrine, 3,4-dimethoxyphenethyl-β-guanidine, and 1,14-sperminedihomovanillamide: potential anti-inflammatory alkaloids isolated from the New Zealand ascidian Aplidium orthium that act as inhibitors of neutrophil respiratory burst
- Source :
-
Tetrahedron . Jun2008, Vol. 64 Issue 24, p5748-5755. 8p. - Publication Year :
- 2008
-
Abstract
- Abstract: In addition to the known dihydroxystyrylguanidine alkaloid tubastrine (1), five new dimers, orthidines A–E (2–6) and the biosynthetically unrelated 1,14-sperminedihomovanillamide (orthidine F, 7) were isolated from the New Zealand ascidian Aplidium orthium. The structures of the new compounds, elucidated by interpretation of spectroscopic data, encompass benzodioxane neolignan-type scaffolds (2–5) and a 1,2,3,4-tetrasubstituted cyclobutane (6), the latter likely having arisen via [π2s+π2s] dimerization of tubastrine. The subunit head-to-tail orientation of dimer 6 was established unambiguously by interpretation of data from a 2 J,3 J-HMBC NMR experiment. The structure of 7 was also confirmed by facile synthesis. Compounds 1–4, 6, and 7 inhibited the in vitro production of superoxide by PMA-stimulated human neutrophils in a dose-dependent manner with IC50s of 10–36μM and this was associated with inhibition of superoxide production by neutrophils in vivo in a murine model of gouty inflammation. [Copyright &y& Elsevier]
- Subjects :
- *ORGANONITROGEN compounds
*GREEN products
*RAW materials
*OXYGEN
Subjects
Details
- Language :
- English
- ISSN :
- 00404020
- Volume :
- 64
- Issue :
- 24
- Database :
- Academic Search Index
- Journal :
- Tetrahedron
- Publication Type :
- Academic Journal
- Accession number :
- 32073538
- Full Text :
- https://doi.org/10.1016/j.tet.2008.04.012