A cyclic ether that is butane in which one hydrogen from each methyl group is substituted by an oxygen.
ChEBI ID: 26911
There is 1 compound belonging to this class, involving 4 study.
| Member | Definition | Role |
|---|---|---|
| tanegool | A lignan that consists of tetrahydrofuran ring substituted by a 4-hydroxy-3-methoxyphenyl group at position 5, a hydroxyphenyl group at position 4 and a hydroxy(4-hydroxy-3-methoxyphenyl)methyl group at position 3. It has been isolated from Taxus yunnanensis. | plant metabolite |
| Pre-1990 | 1990-2000 | 2001-2010 | 2011-2020 | Post-2020 |
|---|---|---|---|---|
| 0 | 0 | 1 | 2 | 1 |
| Article |
|---|
Bioactive Arylnaphthalide Lignans from
Eleven previously undescribed arylnaphthalide lignans ( |
A bio-inspired total synthesis of tetrahydrofuran lignans.
Lignan natural products comprise a broad spectrum of biologically active secondary metabolites. Their structural diversity belies a common biosynthesis, which involves regio- and chemoselective oxidative coupling of propenyl phenols. Attempts to replicate this oxidative coupling have revealed significant challenges for controlling selectivity, and these challenges have thus far prevented the development of a unified biomimetic route to compounds of the lignan family. A practical solution is presented that hinges on oxidative ring opening of a diarylcyclobutane to intercept a putative biosynthetic intermediate. The effectiveness of this approach is demonstrated by the first total synthesis of tanegool in 4 steps starting from ferulic acid, as well as a concise synthesis of the prototypical furanolignan pinoresinol. |
Cytochrome P450 3A4 inhibitory constituents of the wood of Taxus yunnanensis.
From the aqueous extract of the wood of Taxus yunnanensis, which showed cytochrome P450 3A4 (CYP3A4) inhibition, a new isoflavan [(3S,4R)-4'-hydroxy-6,3'-dimethoxyisoflavan-4-ol (1)], a new degraded lignan [2,3-bis(hydroxymethyl)-7-hydroxy-6-methoxy-1-tetralone (2)], and a new lignan [(7R)-7-hydroxytaxiresinol (3)] were isolated, together with nine known lignans. Among the isolates obtained, α-conidendrin (12) showed strong CYP3A4 inhibition with an IC(50) value of 0.2 μM. |
Bioactive lignans from a cultivar of Helianthus annuus.
A bioassay-guided fractionation of water extracts from Helianthus annuus cv. SH-222 was carried out. Ten lignans and a phenylpropanoid were isolated from the polar bioactive fractions of H. annuus. This study is the first to report lignans as constituents of sunflower and is the first time that tanegool has been isolated as a natural aglycone. Additionally, we report biological activities of the isolated compounds. The general bioactivity has been evaluated using the wheat coleoptiles bioassay. The phytotoxic activities of compounds pinoresinol, lariciresinol, dihydro-dehydrodiconiferilic alcohol, and l-(4'-hydroxy-3'-methoxyphenyl)-2-[4' '-(3hydroxypropyl)-2' '-methoxyphenoxy]propane-l,3-diol were also evaluated in a bioassay on the standard target species. The structure-activity relationships are discussed. |