Abstract
Systematic phytochemical investigations of the underground rhizome of Pteridium aquilinum (L.) Kuhn (Dennstaedtiaceae) afforded thirty-five pterosins and pterosides. By detailed analysis of one- and two-dimensional nuclear magnetic resonance spectroscopy, circular dichroism (CD) and high-resolution mass spectrometric data, thirteen previously undescribed pterosins and pterosides have been identified. Interestingly, for the first time 12-O-β-D-glucopyranoside substituted pterosins, rhedynosides C and D, and the sulfate-containing pterosin, rhedynosin H, alongside the two known compounds, histiopterosin A and (2S)-pteroside A2, were isolated from the rhizomes of subsp. aquilinum of bracken. In addition, six-membered cyclic ether pterosins and pterosides, rhedynosin A and rhedynoside A, are the first examples of this type of pterosin-sesquiterpenoid. Additionally, the three previously reported compounds (rhedynosin I, (2S)-2-hydroxymethylpterosin E and (2S)-12-hydroxypterosin A) were obtained for the first time from plants as opposed to mammalian metabolic products. Single crystal X-ray diffraction analysis was applied to the previously undescribed compounds (2R)-rhedynoside B, (2R)-pteroside B and (2S)-pteroside K, yielding the first crystal structures for pterosides, and three known pterosins, (2S)-pterosin A, trans-pterosin C and cis-pterosin C. Rhedynosin C is the only example of the cyclic lactone pterosins with a keto group at position C-14. Six selected pterosins ((2S)-pterosin A, (2R)-pterosin B and trans-pterosin C) and associated glycosides ((2S)-pteroside A, (2R)-pteroside B and pteroside Z) were assessed for their anti-diabetic activity using an intestinal glucose uptake assay; all were found to be inactive at 300 μM
Original language | English |
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Pages (from-to) | 82-94 |
Number of pages | 13 |
Journal | Phytochemistry |
Volume | 128 |
Early online date | 10 May 2016 |
DOIs | |
Publication status | Published - 01 Aug 2016 |
Keywords
- Pteridium aquilinum
- Dennstaedtiaceae
- Bracken pterosins
- Pterosides
- Norsesquiterpenes
- Sesquiterpenoids
- Pterosins A and B
- Circular dichroism
- SGLT1 and GLUT2 transporters
- Glycosides/chemistry
- Indans/chemistry
- Pteridium/chemistry
- Sesquiterpenes/chemistry
- Diabetes Mellitus/drug therapy
- Animals
- Nuclear Magnetic Resonance, Biomolecular
- Rhizome/chemistry
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