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Two Unusual Methylidenecyclopropane Glucosides from Metaxya rostrata C.Presl.

Kainz KP, Virtbauer J, Kählig H, Arion V, Donath O, Reznicek G, Huber W, Marian B, Krenn L - Helv. Chim. Acta (2012)

Bottom Line: Two new natural compounds, (1R,2E)-2-(6-hydroxyhexylidene)cyclopropyl-β-D-glucopyranoside (1) and (6E)-6-[(2R)-2-(β-D-glucopyranosyloxy)cyclopropylidene]hexanoic acid (2), glucosides of a very rare methylidenecyclopropane alcohol, as well as two known glycosides of phenolic acids, namely 4-O-β-D-glucopyranosylcaffeic acid (3) and (E)-4-O-β-D-glucopyranosylcoumaric acid (4), and methyl α-fructofuranoside (5) were isolated for the first time from the rhizomes of the tree fern Metaxya rostrata C.Presl.The structures were elucidated on the basis of detailed spectroscopic data analysis, and the structure of 1 was additionally confirmed by X-ray crystal-structure analysis.

View Article: PubMed Central - PubMed

Affiliation: Department of Pharmacognosy, University of Vienna Althanstr. 14, AT-1090 Vienna.

ABSTRACT
Two new natural compounds, (1R,2E)-2-(6-hydroxyhexylidene)cyclopropyl-β-D-glucopyranoside (1) and (6E)-6-[(2R)-2-(β-D-glucopyranosyloxy)cyclopropylidene]hexanoic acid (2), glucosides of a very rare methylidenecyclopropane alcohol, as well as two known glycosides of phenolic acids, namely 4-O-β-D-glucopyranosylcaffeic acid (3) and (E)-4-O-β-D-glucopyranosylcoumaric acid (4), and methyl α-fructofuranoside (5) were isolated for the first time from the rhizomes of the tree fern Metaxya rostrata C.Presl. The structures were elucidated on the basis of detailed spectroscopic data analysis, and the structure of 1 was additionally confirmed by X-ray crystal-structure analysis.

No MeSH data available.


ORTEP Plot (ellipsoids 50% probability) of compound 1
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fig03: ORTEP Plot (ellipsoids 50% probability) of compound 1

Mentions: Compound 1 additionally was crystallized in a solvent mixture of MeOH and Et2O. X-Ray-diffraction analysis established the relative configuration of the stereogenic centre in the methylidenecyclopropyl-alcohol moiety relative to glucose (Fig. 3)1) The absolute configuration of the glucose was established after hydrolysis, reaction of the sugar with chiral (−)-(R)-butan-2-ol, trimethylsilylation, and GC/MS analysis of the resulting derivative [5] [6], and, consequently, the absolute configuration of the aglycone was deduced as (R).


Two Unusual Methylidenecyclopropane Glucosides from Metaxya rostrata C.Presl.

Kainz KP, Virtbauer J, Kählig H, Arion V, Donath O, Reznicek G, Huber W, Marian B, Krenn L - Helv. Chim. Acta (2012)

ORTEP Plot (ellipsoids 50% probability) of compound 1
© Copyright Policy - open-access
Related In: Results  -  Collection

License
Show All Figures
getmorefigures.php?uid=PMC3569612&req=5

fig03: ORTEP Plot (ellipsoids 50% probability) of compound 1
Mentions: Compound 1 additionally was crystallized in a solvent mixture of MeOH and Et2O. X-Ray-diffraction analysis established the relative configuration of the stereogenic centre in the methylidenecyclopropyl-alcohol moiety relative to glucose (Fig. 3)1) The absolute configuration of the glucose was established after hydrolysis, reaction of the sugar with chiral (−)-(R)-butan-2-ol, trimethylsilylation, and GC/MS analysis of the resulting derivative [5] [6], and, consequently, the absolute configuration of the aglycone was deduced as (R).

Bottom Line: Two new natural compounds, (1R,2E)-2-(6-hydroxyhexylidene)cyclopropyl-β-D-glucopyranoside (1) and (6E)-6-[(2R)-2-(β-D-glucopyranosyloxy)cyclopropylidene]hexanoic acid (2), glucosides of a very rare methylidenecyclopropane alcohol, as well as two known glycosides of phenolic acids, namely 4-O-β-D-glucopyranosylcaffeic acid (3) and (E)-4-O-β-D-glucopyranosylcoumaric acid (4), and methyl α-fructofuranoside (5) were isolated for the first time from the rhizomes of the tree fern Metaxya rostrata C.Presl.The structures were elucidated on the basis of detailed spectroscopic data analysis, and the structure of 1 was additionally confirmed by X-ray crystal-structure analysis.

View Article: PubMed Central - PubMed

Affiliation: Department of Pharmacognosy, University of Vienna Althanstr. 14, AT-1090 Vienna.

ABSTRACT
Two new natural compounds, (1R,2E)-2-(6-hydroxyhexylidene)cyclopropyl-β-D-glucopyranoside (1) and (6E)-6-[(2R)-2-(β-D-glucopyranosyloxy)cyclopropylidene]hexanoic acid (2), glucosides of a very rare methylidenecyclopropane alcohol, as well as two known glycosides of phenolic acids, namely 4-O-β-D-glucopyranosylcaffeic acid (3) and (E)-4-O-β-D-glucopyranosylcoumaric acid (4), and methyl α-fructofuranoside (5) were isolated for the first time from the rhizomes of the tree fern Metaxya rostrata C.Presl. The structures were elucidated on the basis of detailed spectroscopic data analysis, and the structure of 1 was additionally confirmed by X-ray crystal-structure analysis.

No MeSH data available.