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. 2017 Aug 21;73(Pt 9):1368-1371.
doi: 10.1107/S2056989017011902. eCollection 2017 Sep 1.

Crystal structures of hibiscus acid and hibiscus acid dimethyl ester isolated from Hibiscus sabdariffa (Malvaceae)

Ahmed M Zheoat  1 , Alexander I Gray  1 , John O Igoli  1 , Alan R Kennedy  2 , Valerie A Ferro  1
Affiliations

Crystal structures of hibiscus acid and hibiscus acid dimethyl ester isolated from Hibiscus sabdariffa (Malvaceae)

Ahmed M Zheoat et al. Acta Crystallogr E Crystallogr Commun. .

Abstract

The biologically active title compounds have been isolated from Hibiscus sabdariffa plants, hibiscus acid as a dimethyl sulfoxide monosolvate [systematic name: (2S,3R)-3-hy-droxy-5-oxo-2,3,4,5-tetra-hydro-furan-2,3-di-carb-oxy-lic acid dimethyl sulfoxide monosolvate], C6H6O7·C2H6OS, (I), and hibiscus acid dimethyl ester [systematic name: dimethyl (2S,3R)-3-hy-droxy-5-oxo-2,3,4,5-tetra-hydro-furan-2,3-di-carboxyl-ate], C8H10O7, (II). Compound (I) forms a layered structure with alternating layers of lactone and solvent mol-ecules, that include a two-dimensional hydrogen-bonding construct. Compound (II) has two crystallographically independent and conformationally similar mol-ecules per asymmetric unit and forms a one-dimensional hydrogen-bonding construct. The known absolute configuration for both compounds has been confirmed.

Keywords: crystal structure; hibiscus; hydrogen bonding; lactone acids; natural products.

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Figures

Figure 1
Figure 1
The mol­ecular structure of compound (I), with the atom labelling and 50% probability displacement ellipsoids.
Figure 2
Figure 2
The mol­ecular structures of the two independent mol­ecules comprising the asymmetric unit of (II), with the atom labelling and 50% probability displacement ellipsoids.
Figure 3
Figure 3
Hydrogen-bonding contacts in (I).
Figure 4
Figure 4
The crystal packing of compound (I), viewed along the a axis.
Figure 5
Figure 5
A section of the extended structure of (II), with the hydrogen-bonded polymer extending left and right parallel to the a axis.
See this image and copyright information in PMC

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