dos S Grecco S et al. (2014), Structural crystalline characterization of saku...

ECB-ART-43448

Molecules 2014 Jun 06;196:7528-42. doi: 10.3390/molecules19067528.

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Structural crystalline characterization of sakuranetin--an antimicrobial flavanone from twigs of Baccharis retusa (Asteraceae).

dos S Grecco S , Dorigueto AC , Landre IM , Soares MG , Martho K , Lima R , Pascon RC , Vallim MA , Capello TM , Romoff P , Sartorelli P , Lago JH .

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Bioactivity-guided fractionation of an antimicrobial active extract from twigs of Baccharis retusa C. DC. (Asteraceae) yielded the flavanone 5,4''-dihydroxy-7-methoxy-flavanone (sakuranetin) as responsible for the detected activity. The structure of the bioactive compound was established on the basis of spectroscopic data analysis, including NMR and MS. Additionally, the structure of a new crystal form of sakuranetin was confirmed by X-ray diffratometry. The minimum inhibitory concentrations (MIC) of isolated compound were determined against pathogenic yeast belonging to the genus Candida (six species), Cryptococcus (two species/four serotypes) and S. cerevisiae BY 4742 (S288c background) and ranged from 0.32 to 0.63 μg/μL. Our results showed that sakuranetin, which structure was fully characterized, could be used as a tool for the design of novel and more efficacious antifungal agents.

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Genes referenced: LOC100893907 LOC105444942

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References [+] :

Allen, The Cambridge Structural Database: a quarter of a million crystal structures and rising. 2002, Pubmed

	Figure 1. Chemical structure of 5,4'-dihydroxy-7-methoxy-flavanone (sakuranetin).
	Figure 2. ORTEP plot and atom numbering of (a) molecule A and (b) molecule B of sakuranetin-monohydrate (S-enantiomer arbitrary chosen). Ellipsoids represent 50%-probability level. Double-dotted lines represent intramolecular H-bond. Disorder in the rings is detailed in light grey and black. Water molecules were omitted for clarity.
	Figure 3. Superimposed structures for the sakuranetin-anhydrous and sakuranetin-dihydrate forms.
	Figure 4. Superimposed structures for: (a) conformers Aa + Ba of sakuranetin-monohydrate; (b) conformers Ab + Bb of sakuranetin-monohydrate; and (c) conformers Ab of sakuranetin-monohydrate + sakuranetin-dihydrate. Hydrogen atoms were omitted for clarity. [Color legend: light grey = Aa and Ab; dark grey = Ba, Bb and sakuranetin-dihydrate].
	Figure 5. Details of molecules A and B in sakuranetin-monohydrate related to the pseudo-inversion center. Solid green lines show atoms related by the inversion center (black point). The inversion symmetry is forbidden for the stereogenic atoms C10 and C26 in the homologous chromane rings (highlighted by circles).
	Figure 6. A section of the supramolecular 2D assembly of sakuranetin-monohydrate (Molecule A), projected onto (001). The chains propagation along [100] and [010] are evident. Hydrogen bonds are shown as dashed lines. Displacement ellipsoids are drawn at the 30% probability level. H of carbon atoms were omitted for clarity. [Symmetry codes: (i) x, y − 1, z; (ii) −x, −y, z; (iii) x, y + 1, z; (iv) x + 1, y + 1, z; (v) x − 1, y + 1, z; (vi) x − 1, y, z].
	Figure 7. The crystal packing illustration of sakuranetin-monohydrate onto the bc plane.
	Figure 8. The crystal packing illustration of sakuranetin-monohydrate onto the ac plane.
	Figure 9. A section of the supramolecular double chain of sakuranetin-monohydrate projected onto (104) with double chain propagation along [010]. Hydrogen bonds are shown as dashed lines. Displacement ellipsoids are drawn at the 30% probability level. H of carbon atoms were omitted for clarity. [Symmetry code: (vii) x + 1, y, z].