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

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Zheoat, Ahmed M. ; Gray, Alexander I. ; Igoli, John O. ; Kennedy, Alan R. ; Ferro, Valerie A. (2017)
  • Publisher: International Union of Crystallography
  • Journal: Acta Crystallographica Section E: Crystallographic Communications, volume 73, issue Pt 9, pages 1,368-1,371 (issn: 2056-9890, eissn: 2056-9890)
  • Related identifiers: doi: 10.1107/S2056989017011902, pmc: PMC5588582
  • Subject: Chemistry | natural products | hydrogen bonding | lactone acids | hibiscus | QD1-999 | crystal structure | Research Communications

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