Dergiler / Turkish Journal of Chemistry / 2005 / Cilt: 29 - Sayı: 3
Pyranocoumarins from Seseli gummiferum subsp. corymbosum Growing in Turkey
- Sayfa
- 327–334
- DOI
- —
Özet
Seseli gummiferum Pall. ex Sm. subsp. corymbosum (Boiss. & Heldr.) P.H. Davis (Syn: S. corymbosum Boiss. & Heldr.) (Umbelliferae) collected in southern Anatolia was investigated for the presence of coumarins. A new angular-type pyranocoumarin, corymbocoumarin (1), along with 5 known coumarins (2-6) were isolated from the aerial parts of this plant. Corymbocoumarin (1) was established to be (-)-(3'S,4'S)-3' -acetoxy-4'-isovaleryloxy-3',4' -dihydroseselin (1) and coumarins 2-6 were identified as (-)-(3'S,4'S) -3'-acetoxy-4' -angeloyloxy-3' ,4' -dihydroseselin (2), (+)-(3' S,4' S)-3' -hydroxy-4' -angeloyloxy-3', 4' -dihydroseselin (d-laserpitin) (3), (-)-(3' S,4' S)-3' -angeloyloxy-4' -hydroxy-3', 4' -dihydroseselin (4), 3' -acetoxy-4' -isobutyloxy-3', 4' -dihydroseselin (5) and osthole (6), respectively, by spectroscopic methods. The structural elucidation and absolute configurations were determined by chemical correlations with known compounds.
Abstract
Seseli gummiferum Pall. ex Sm. subsp. corymbosum (Boiss. & Heldr.) P.H. Davis (Syn: S. corymbosum Boiss. & Heldr.) (Umbelliferae) collected in southern Anatolia was investigated for the presence of coumarins. A new angular-type pyranocoumarin, corymbocoumarin (1), along with 5 known coumarins (2-6) were isolated from the aerial parts of this plant. Corymbocoumarin (1) was established to be (-)-(3'S,4'S)-3' -acetoxy-4'-isovaleryloxy-3',4' -dihydroseselin (1) and coumarins 2-6 were identified as (-)-(3'S,4'S) -3'-acetoxy-4' -angeloyloxy-3' ,4' -dihydroseselin (2), (+)-(3' S,4' S)-3' -hydroxy-4' -angeloyloxy-3', 4' -dihydroseselin (d-laserpitin) (3), (-)-(3' S,4' S)-3' -angeloyloxy-4' -hydroxy-3', 4' -dihydroseselin (4), 3' -acetoxy-4' -isobutyloxy-3', 4' -dihydroseselin (5) and osthole (6), respectively, by spectroscopic methods. The structural elucidation and absolute configurations were determined by chemical correlations with known compounds.