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- W2397552050 abstract "Ocotillol-type saponins have a wide spectrum of biological activities. Previous studies indicated that the configuration at the C24 position may be responsible for their stereoselectivity in pharmacological action and pharmacokinetics. Natural ocotillol-type saponins share a 20( S )-form but it has been found that the 20( R )-stereoisomers have different pharmacological effects. The semisynthesis of 20( R )-ocotillol-type saponins has not been reported and it is therefore worthwhile clarifying their crystal structures. Two C24 epimeric 20( R )-ocotillol-type saponins, namely (20 R ,24 S )-20,24-epoxydammarane-3β,12β,25-triol, C 30 H 52 O 4 , (III), and (20 R ,24 R )-20,24-epoxydammarane-3β,12β,25-triol monohydrate, C 30 H 52 O 4 ·H 2 O, (IV), were synthesized, and their structures were elucidated by spectral studies and finally confirmed by single-crystal X-ray diffraction. The (Me)C—O—C—C(OH) torsion angle of (III) is 146.41 (14)°, whereas the corresponding torsion angle of (IV) is −146.4 (7)°, indicating a different conformation at the C24 position. The crystal stacking in (III) generates an R 4 4 (8) motif, through which the molecules are linked into a one-dimensional double chain. The chains are linked via nonclassical C—H...O hydrogen bonds into a two-dimensional network, and further stacked into a three-dimensional structure. In contrast to (III), epimer (IV) crystallizes as a hydrate, in which the water molecules act as hydrogen-bond donors linking one-dimensional chains into a two-dimensional network through intermolecular O—H...O hydrogen bonds. The hydrogen-bonded chains extend helically along the crystallographic a axis and generate a C 4 4 (8) motif." @default.
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- W2397552050 date "2016-05-18" @default.
- W2397552050 modified "2023-09-23" @default.
- W2397552050 title "Synthesis and crystal structures of C24-epimeric 20(<i>R</i>)-ocotillol-type saponins" @default.
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- W2397552050 doi "https://doi.org/10.1107/s2053229616007270" @default.
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