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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.


Structures of compounds 1–5
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fig01: Structures of compounds 1–5

Mentions: Rhizomes of Metaxya rostrata were extracted with hot water according to the ethnomedicinal procedure and fractionated. After vacuum liquid chromatography and repeated column chromatography on silica gel or Sephadex LH-20, two new compounds 1 and 2, two phenolic acid glycosides 3 and 4, and a methyl glycoside 5 have been isolated (Fig. 1).


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)

Structures of compounds 1–5
© Copyright Policy - open-access
Related In: Results  -  Collection

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

fig01: Structures of compounds 1–5
Mentions: Rhizomes of Metaxya rostrata were extracted with hot water according to the ethnomedicinal procedure and fractionated. After vacuum liquid chromatography and repeated column chromatography on silica gel or Sephadex LH-20, two new compounds 1 and 2, two phenolic acid glycosides 3 and 4, and a methyl glycoside 5 have been isolated (Fig. 1).

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.