Three New Illudalane Sequiterpenoids from Pteris semipinnata

Abstract

The chemical investigation of the aerial parts of Pteris semipinnata resulted in the isolation of three illudalane sesquiterpenoids, namely (2R)-norpterosin B (1), (2R)-12-O-b-d-glucopyranosylnorpterosin B (2), and semipterosin A (3), along with three known compounds. The structures of 1 -3 were established by spectroscopic methods, including extensive 2D-NMR and CD analyses.

Phytochemicals from fern species: potential for medicine applications

“…The basic flavonoid aglycones in this genus are apigenin, kaempferol, quercetin, and luteolin. For example, two known flavonoids, apigenin 7-O-α-D-glucoside and apigenin 7-O-α-D-glucuronide, have been obtained from P. semipinnata (Zhan et al 2010). New flavonoids are still being isolated from Pteris.…”

“…In addition to diterpenoids, several new sesquiterpenoid indanone derivatives including pterisemipol, (2R)-norpterosin B, (2R)-12-O-β-D-glucopyranosylnorpterosin B and semipterosin A ( Fig. 9) have been found in P. semipinnata (Zhang and Xuan 2007;Zhan et al 2010). Pterosin sesquiterpenoids (Table 4) were first isolated from bracken, P. aquilinum var.…”

Pterisolic Acids A-F, New ent-Kaurane Diterpenoids from the Fern Pteris semipinnata

“…2) from the proton at d H 5.12 (1H, br dd, Jϭ7. 7,6.8 Hz) to the carbons at d C 45.5 (s, C-4) and 54.7 (s, C-8), and from the protons at d H 6.10, 5.74 (each 1H, br s, H-17) to the carbon at d C 75.1 (s), were observed, revealing the presence of hydroxy groups at C-6 and C-13. While the observable HMBC correlations (Fig.…”

“…[1][2][3][4][5][6][7] As part of BioBioPha to assemble a large-scale natural product library which is very valuable in the discovery of new drug leads from nature, [8][9][10][11] the further phytochemical investigation on the whole plants of Pteris semipinnata afforded six new ent-15-oxokauran-19-oic acid derivatives, named pterisolic acids A-F (1-6), along with known ent-kauranoids, ent-9a-hydroxy-15-oxo-16b(H)-kauran-19-oic acid (7), 2) ent-9a-hy-3) Herein, we report the isolation and structure elucidation of these new constituents. …”

Natural sesquiterpenoids

“…200 Three new illudalane sesquiterpenes, (2R)-norpterosin B 212, its glucoside 213 and semipterosin A 214, have been found in an extract of Pteris semipinnata. 201 Another species of this genus, Pteris multifida, contains (2R)-pterosin P 215 and dehydropterosin B 216. 202 The total syntheses of alcyopterosins C, I and L-N have been accomplished.…”