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

Allbwn ymchwil: Cyfraniad at gyfnodolynErthygladolygiad gan gymheiriaid

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Isolation and characterisation of 13 pterosins and pterosides from bracken (Pteridium aquilinum (L.) Kuhn) rhizome. / Mohammad, Rizgar; Nur-e-Alam, Mohammad; Lahmann, Martina et al.
Yn: Phytochemistry, Cyfrol 128, 08.2016, t. 82-94.

Allbwn ymchwil: Cyfraniad at gyfnodolynErthygladolygiad gan gymheiriaid

HarvardHarvard

Mohammad, R, Nur-e-Alam, M, Lahmann, M, Parveen, I, Tizzard, GJ, Coles, SJ, Fowler, M, Drake, AF, Heyes, D & Thoss, V 2016, 'Isolation and characterisation of 13 pterosins and pterosides from bracken (Pteridium aquilinum (L.) Kuhn) rhizome', Phytochemistry, cyfrol. 128, tt. 82-94. https://doi.org/10.1016/j.phytochem.2016.05.001

APA

Mohammad, R., Nur-e-Alam, M., Lahmann, M., Parveen, I., Tizzard, G. J., Coles, S. J., Fowler, M., Drake, A. F., Heyes, D., & Thoss, V. (2016). Isolation and characterisation of 13 pterosins and pterosides from bracken (Pteridium aquilinum (L.) Kuhn) rhizome. Phytochemistry, 128, 82-94. https://doi.org/10.1016/j.phytochem.2016.05.001

CBE

Mohammad R, Nur-e-Alam M, Lahmann M, Parveen I, Tizzard GJ, Coles SJ, Fowler M, Drake AF, Heyes D, Thoss V. 2016. Isolation and characterisation of 13 pterosins and pterosides from bracken (Pteridium aquilinum (L.) Kuhn) rhizome. Phytochemistry. 128:82-94. https://doi.org/10.1016/j.phytochem.2016.05.001

MLA

VancouverVancouver

Mohammad R, Nur-e-Alam M, Lahmann M, Parveen I, Tizzard GJ, Coles SJ et al. Isolation and characterisation of 13 pterosins and pterosides from bracken (Pteridium aquilinum (L.) Kuhn) rhizome. Phytochemistry. 2016 Awst;128:82-94. Epub 2016 Mai 10. doi: 10.1016/j.phytochem.2016.05.001

Author

Mohammad, Rizgar ; Nur-e-Alam, Mohammad ; Lahmann, Martina et al. / Isolation and characterisation of 13 pterosins and pterosides from bracken (Pteridium aquilinum (L.) Kuhn) rhizome. Yn: Phytochemistry. 2016 ; Cyfrol 128. tt. 82-94.

RIS

TY - JOUR

T1 - Isolation and characterisation of 13 pterosins and pterosides from bracken (Pteridium aquilinum (L.) Kuhn) rhizome

AU - Mohammad, Rizgar

AU - Nur-e-Alam, Mohammad

AU - Lahmann, Martina

AU - Parveen, Ifat

AU - Tizzard, Graham J.

AU - Coles, Simon J.

AU - Fowler, Mark

AU - Drake, Alex F.

AU - Heyes, Darren

AU - Thoss, Vera

PY - 2016/8

Y1 - 2016/8

N2 - 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.

AB - 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.

U2 - 10.1016/j.phytochem.2016.05.001

DO - 10.1016/j.phytochem.2016.05.001

M3 - Article

VL - 128

SP - 82

EP - 94

JO - Phytochemistry

JF - Phytochemistry

SN - 0031-9422

ER -