Pteroside A

Chemical and biologically active constituents of Pteris multifida.[Pubmed: 18553125]

J Nat Med. 2008 Oct;62(4):452-5.

A new compound, 4-caffeoyl quinic acid 5-O-methyl ether (2), together with 12 known compounds--identified as (2R,3R)-pterosin L 3-O-beta-D-glucopyrannoside (3), beta-sitosterol beta-D-glucopyranoside (4), apigenin 7-O-beta-D-glucopyranoside (5), luteolin 7-O-beta-D-glucopyranoside (6), sucrose (7), caffeic acid (8), pterosin C 3-O-beta-D-glucopyranoside (9), pteroside C (10), 4,5-dicaffeoyl quinic acid (11), Pteroside A (12), wallichoside (13) and (2S)-5,7,3',5'-tetrahydroxyflavanone (14)--were isolated from Pteris multifida.
METHODS AND RESULTS:
The structure of the new compound was determined by means of physical, chemical and spectroscopic evidence. Compounds 5 and 6 were the main constituents of the plant, with yields of 0.19% and 0.16%, respectively. The cytotoxic activities of 2, 3, and 9-13 were evaluated against a human cell line (KB cells).
CONCLUSIONS:
Among the isolated compounds, pterosin C 3-O-beta-D-glucopyrannoside (9) and 4,5-dicaffeoylquinic acid (11) showed a significant selective cytotoxicity (IC(50) 2.35 and 5.38, respectively), while moderate activity was observed for compound 2 (IC(50) 12.3). The chemosystematics of Pteris species is also discussed.

Phytochemistry. 2016 Aug;128:82-94.

Isolation and characterisation of 13 pterosins and pterosides from bracken (Pteridium aquilinum (L.) Kuhn) rhizome.[Pubmed: 27177933 ]

Systematic phytochemical investigations of the underground rhizome of Pteridium aquilinum (L.) Kuhn (Dennstaedtiaceae) afforded thirty-five pterosins and pterosides.
METHODS AND RESULTS:
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.
CONCLUSIONS:
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.