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

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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-hydroxy-5-oxo-2,3,4,5-tetrahydrofuran-2,3-dicarboxylic acid dimethyl sulfoxide monosolvate], C6H6O7C2H6OS, (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.
LanguageEnglish
Pages1368-1371
Number of pages4
JournalActa Crystallographica Section E: Structure Reports
VolumeE73
DOIs
StatePublished - 22 Aug 2017

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tetrahydrofuran
Dimethyl Sulfoxide
esters
Esters
Hydrogen bonds
Dimethyl sulfoxide
Crystal structure
Dicarboxylic Acids
acids
crystal structure
Molecules
Acids
dicarboxylic acids
Lactones
hydrogen
molecules
configurations
hydroxycitric acid

Keywords

  • crystal structure
  • natural products
  • hibiscus
  • lactone acids
  • hydogen bonding

Cite this

@article{710e388055be479ca94b1053079a7735,
title = "Crystal structures of hibiscus acid and hibiscus acid dimethyl ester isolated from Hibiscus sabdariffa (Malvaceae)",
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-hydroxy-5-oxo-2,3,4,5-tetrahydrofuran-2,3-dicarboxylic acid dimethyl sulfoxide monosolvate], C6H6O7C2H6OS, (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.",
keywords = "crystal structure, natural products, hibiscus, lactone acids, hydogen bonding",
author = "Zheoat, {Ahmed M.} and Alexander Gray and John Igoli and Kennedy, {Alan R.} and Ferro, {Valerie A.}",
note = "Accepted on 16/8/2017 as a paper in an open access journal.",
year = "2017",
month = "8",
day = "22",
doi = "10.1107/S2056989017011902",
language = "English",
volume = "E73",
pages = "1368--1371",
journal = "Acta Crystallographica Section E: Structure Reports",
issn = "1600-5368",

}

TY - JOUR

T1 - Crystal structures of hibiscus acid and hibiscus acid dimethyl ester isolated from Hibiscus sabdariffa (Malvaceae)

AU - Zheoat,Ahmed M.

AU - Gray,Alexander

AU - Igoli,John

AU - Kennedy,Alan R.

AU - Ferro,Valerie A.

N1 - Accepted on 16/8/2017 as a paper in an open access journal.

PY - 2017/8/22

Y1 - 2017/8/22

N2 - 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], C6H6O7C2H6OS, (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.

AB - 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], C6H6O7C2H6OS, (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.

KW - crystal structure

KW - natural products

KW - hibiscus

KW - lactone acids

KW - hydogen bonding

UR - http://scripts.iucr.org/cgi-bin/paper?S2056989017011902

U2 - 10.1107/S2056989017011902

DO - 10.1107/S2056989017011902

M3 - Article

VL - E73

SP - 1368

EP - 1371

JO - Acta Crystallographica Section E: Structure Reports

T2 - Acta Crystallographica Section E: Structure Reports

JF - Acta Crystallographica Section E: Structure Reports

SN - 1600-5368

ER -