Relative Configuration of Glechomafuran Isolated from the Fruits of Smyrnium olusatrum

A forgotten vegetable (Smyrnium olusatrum L., Apiaceae) as a rich source of isofuranodiene

“…Fractions 40-45 yielded furanoeremophil-1-one (90) (174 mg, white solid, 99%). The structures of the compounds furanoeremophil-1-one, glechomafuran and 1b-acetoxyfuranoeudesm-4(15)-ene were confirmed by 1 H-NMR and 13 C-NMR spectra, which were in agreement with those reported in literature (Mölleken, Sinnwell, & Kubeczka, 1998b;Mölleken et al, 1998a;Ulubelen & Öksüz, 1983). …”

“…Although isofuranodiene and curzerene were revealed as two of the main compounds of wild celery essential oil by several authors (Bertoli et al, 2004;Mölleken et al, 1998a;Papaioannou et al, 2010;Ulubelen & Öksüz, 1983), no one verified their concentrations in essential oils by using a different approach, with respect to conventional gas chromatographic conditions, in order to avoid the isofuranodiene rearrangement in the GC injector and column (Baldovini et al, 2001;Yang et al, 2007). Therefore, in the present work, we developed an HPLC-DAD method to quantify these thermosensitive constituents in the essential oils.…”

“…Besides isofuranodiene and curzerene (together 27.4% and 11.3% in green and ripe fruits, respectively), 1b-acetoxyfurano-4(15)-eudesmene was one of the most abundant compounds, accounting for 7.27% and 12.3% in green and ripe fruits, respectively. Ulubelen and Öksüz (1983) examined air-dried fruits of S. olusatrum from the west coast of Turkey, and isolated the furanogermacrane glechomafuran (reported earlier as alexandrofuran). Daroui-Mokaddem et al (2010) analyzed the oil obtained from fresh leaves collected in Algeria, detecting sabinene (27.1%), curzerene (13.7%) and methyl-1 -benzyl-2-oxocyclooctane (12.3%) as the most abundant compounds.…”

Smyrnium olusatrum L.

“…Ulubelen et al . (1983) examined air‐dried fruits of S. olusatrum from coastal west Turkey and isolated the furanogermacrane glechomafuran which Bohlmann & Zdero (1973) described from root tissue.…”

Germacrane Sesquiterpene Esters fromSalvia roborowskii

“…Its molecular formula was confirmed as C 17 H 22 O 5 according to the 13 C-NMR (DEPT) spectrum and EI-MS giving a molecular ion peak at m/z = 306 [M] + . The structure of 4 is easily elucidated as an acetoxy derivative of glechomafuran by direct comparison of its MS, 1 H-and 13 C-NMR spectral data with the known compound glechomafuran reported in the literature [7], [8]. The attachment at C-6 and stereochemistry as b-orientation of the acetoxy group was also assigned on the basis of the typical signal (d H = 6.50, 1H, br s and d C = 65.0, CH).…”