Chemical and chemotaxonomical studies of ferns. XXXIX. Chemical studies on the constituents of Pteris bella Tagawa and Pteridium aquilinum subsp. wightianum (Wall) Shich.

Isolation and characterisation of 13 pterosins and pterosides from bracken (Pteridium aquilinum (L.) Kuhn) rhizome

“…The remaining 1 H NMR signals were in agreement with a pterosin-type structure (Fukuoka et al, 1978;Kovganko et al, 2004;Kuraishi et al, 1985;Tanaka et al, 1982). The 13 C NMR data of 5 (Table 4) shows fourteen distinct carbon environments, confirming the presence of a pentasubstituted aromatic ring, including a low-field signal at C 208.9 ppm (C=O) assigned as the C-1 of a pterosin-type sesquiterpene skeleton.…”

“…In the IR spectrum, strong bands at νmax 1703 and 3428 cm -1 were indicative of carbonyl and hydroxyl groups, respectively. The maximum UV absorbances of 4 appeared at 214, 258 and 306 nm, in agreement with 1-indanone compounds (Tanaka et al, 1982;Yoshihira et al, 1971). Analysis of the NMR and MS spectral data showed that 4 is structural similar to 3.…”

“…In the FT-ICR-MS, 11 was shown to have the molecular formula C21H29ClO7, with a molecular mass 14 Da higher than 10. The UV, IR and NMR data of 11 were similar to those of pterosin H (Hayashi et al, 1972;Padwa et al, 1996;Tanaka et al, 1982) with the exception that 11 contained a sugar moiety. Of particular interest was a pair of geminally coupled doublets in the 1 H NMR spectrum at H 5.11 (1 H, d, J = 12.4 Hz) and H 4.78 (1 H, d, J = 12.4 Hz).…”

“…One-and two-dimensional NMR experiments combined with mass spectrometry were used to identify thirteen novel natural products (1-13) (Supplementary Information 1) belonging to the sesquiterpenoid family. The structures of twenty two previously reported pterosins and pterosides 14, 27, 29 (Lee et al, 2012), 15-18, 30-33, 35 (Kuroyanagi et al, 1979), 19-25 (Fukuoka et al, 1978), 26 (Kuraishi et al, 1985;Tanaka et al, 1982), 28 (Murakami et al, 1980), 34 (Castillo et al, 2003) were determined by the comparison of their spectroscopic data with those reported in the literature . The structures of compound 1-13 are shown in Figs.…”

“…Other pterosins have been isolated from different subsp. of Pteridium aquilinum (Fukuoka et al, 1978;Kuraishi et al, 1985;Murakami et al, 1980;Sengupta et al, 1976;Tanaka et al, 1982;Yoshihira et al, 1971). Pterosins are sesquiterpenoids and their structures are derivatives of 1-indanone.…”