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The bioactive compound 5-hydroxy-7-methoxy-2-phenylchroman-4-one (pinostrobin , I ), was isolated from aerial parts of Nolana ramossisima I.M. Johnst., a Chilean endemic species , using a combination of medium pressure column chromatography and high speed countercurrent liquid-liquid chromatography (HSCCC). The compound crystallized as a non-centrosymmetric polymorph in the orthorhombic chiral space group P2 1 2 1 2 1 . Its structure had been previously reported by Shoja ( Acta Cryst . C45, 828, 1989) and Yamovoi et al. ( Khim. Prir. Soedin (5), 361, 2001) in the centrosymmetric space groups Pbca and P21/c, respectively. INTRODUCTION High speed countercurrent chromatography (HSCCC) is a support-free liquid-liquid partition chromatographic technique which eliminates the problem of the adsorption of a sample onto a solid support and has been widely used for the purification of natural products, including flavanones 1 . In this work this fast technique has been applied in combination with medium pressure column chromatography for the purification of the phenolic constituents in an organic extract of aerial parts of

A NON-CENTROSYMMETRIC POLYMORPH OF 5-HYDROXY-7-METHOXY-2-PHENYLCHROMAN-4-ONE