Isolation and characterisation of 13 pterosins and pterosides from bracken (Pteridium aquilinum (L.) Kuhn) rhizome
Isolation and characterisation of 13 pterosins and pterosides from bracken (Pteridium aquilinum (L.) Kuhn) rhizome
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-?-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 ?M.
82-94
Mohammad, Rizgar Hassan
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Nur-e-Alam, Mohammad
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Lahmann, Martina
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Parveen, Ifat
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Tizzard, Graham J.
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Coles, Simon
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Fowler, Mark
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Drake, Alex F.
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Heyes, Derren
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Thoss, Vera
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August 2016
Mohammad, Rizgar Hassan
727cf718-172b-4986-9148-0b59dbbd0415
Nur-e-Alam, Mohammad
32b7b448-599c-4918-ab9e-fefdb848293a
Lahmann, Martina
6aa6edf8-6928-4ba8-9c51-2bad7571f493
Parveen, Ifat
7839b403-8949-4b72-ac84-840c07561b11
Tizzard, Graham J.
8474c0fa-40df-43a6-a662-7f3c4722dbf2
Coles, Simon
3116f58b-c30c-48cf-bdd5-397d1c1fecf8
Fowler, Mark
75c802cc-cac8-46fb-a5c7-bcaa3e12e873
Drake, Alex F.
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Heyes, Derren
bb47f6dd-4641-40cd-a2e5-82d2f4c7407e
Thoss, Vera
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Mohammad, Rizgar Hassan, Nur-e-Alam, Mohammad, Lahmann, Martina, Parveen, Ifat, Tizzard, Graham J., Coles, Simon, Fowler, Mark, Drake, Alex F., Heyes, Derren and Thoss, Vera
(2016)
Isolation and characterisation of 13 pterosins and pterosides from bracken (Pteridium aquilinum (L.) Kuhn) rhizome.
Phytochemistry, 128, .
(doi:10.1016/j.phytochem.2016.05.001).
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-?-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 ?M.
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Accepted/In Press date: 1 May 2016
e-pub ahead of print date: 10 May 2016
Published date: August 2016
Organisations:
Organic Chemistry: SCF
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Local EPrints ID: 399081
URI: http://eprints.soton.ac.uk/id/eprint/399081
ISSN: 0031-9422
PURE UUID: 0ddb324a-d913-41af-9721-216fbcc35c8d
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Date deposited: 05 Aug 2016 08:37
Last modified: 15 Mar 2024 05:47
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Author:
Rizgar Hassan Mohammad
Author:
Mohammad Nur-e-Alam
Author:
Martina Lahmann
Author:
Ifat Parveen
Author:
Mark Fowler
Author:
Alex F. Drake
Author:
Derren Heyes
Author:
Vera Thoss
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