Structural Crystalline Characterization of Sakuranetin — An Antimicrobial Flavanone from Twigs of Baccharis retusa (Asteraceae)
Abstract
:1. Introduction
2. Results and Discussion
2.1. Chemical Characterization of Sakuranetin by NMR and MS
2.2. Structural Crystalline Characterization of Sakuranetin
Empirical Formula | 2 (C16H14O5·H2O) |
---|---|
Formula weight | 602.53 |
Temperature/K | 120(1) K |
Wavelength/Å | 1.54180 |
Crystal system | Monoclinic |
Space group | P21 |
Unit cell dimensions/Å and ° | a = 4.825(5), b = 13.978(5), c = 21.077(5) |
β = 91.091(5) | |
Volume/Å3 | 1421.3(16) |
Z/Z' | 4/2 |
Density (calculated)/Mg.m−3 | 1.422 |
Absorption coefficient/mm−1 | 0.921 |
F(000) | 640 |
Crystal size | 0.28 × 0.14 × 0.02 mm3 |
Theta range for data collection | 4.20 to 63.27° |
Index ranges | −5 d h d 3, −15 d k d 15, −24 d l d 23 |
Reflections collected | 4538 |
Independent reflections | 3241 [R(int) = 0.0269] |
Completeness to theta = 63.27° | 84.1% |
Refinement method | Full-matrix least-squares on F2 |
Data/restraints/parameters | 3241/1/395 |
Goodness-of-fit on F2 | 1.040 |
Final R index [I > 2 sigma(I)] | R1 = 0.0609, wR2 = 0.1601 |
R index (all data) | R1 = 0.0917, wR2 = 0.1816 |
Largest diff. peak and hole/e.Å−3 | 0.547 and −0.248 |
Torsion Angle | (I)-Anhydrous † | (I)-Dihydrate † | (I)-MonohydrateMolecule A | (I)-MonohydrateMolecule B | ||
---|---|---|---|---|---|---|
conformer a | conformer b | conformer a | conformer b | |||
φ1 | −66.43 | −66.13 | −41.04 | −82.46 | −46.04 | −78.78 |
φ2 | 111.35 | 112.62 | 137.70 | 106.53 | 126.89 | 100.64 |
φ3 | 56.27 | 56.07 | 85.38 | 43.96 | 76.62 | 43.89 |
φ4 | −125.94 | −125.19 | −95.89 | −127.05 | −110.45 | −136.69 |
D–H–A | d (D–H) | d (H–A) | d (D–A) | <(DHA) |
---|---|---|---|---|
O1-H1...O2 | 0.82 | 1.90 | 2.632(9) | 147.7 |
O6-H6...O7 | 0.82 | 1.89 | 2.622(9) | 148.8 |
O5-H5...O12 i | 0.82 | 2.18 | 2.97(1) | 161.5 |
O10-H10a...O11 iv | 0.82 | 2.18 | 2.97(1) | 161.5 |
O12-H12c...O1 | 1.056(6) | 1.783(6) | 2.839(9) | 179.5(5) |
O12-H12d...O5 iv | 0.993(6) | 1.632(7) | 2.625(9) | 179.6(5) |
O11-H11b...O6 | 1.096(5) | 1.830(6) | 2.926(8) | 179.6(4) |
O11-H11a...O10 i | 1.105(6) | 1.826(7) | 2.93(1) | 179.9(4) |
O1-H1...O7 vii | 0.82 | 2.41 | 2.87(1) | 116.3 |
O6 vii-H6...O2 | 0.82 | 2.41 | 2.87(1) | 116.3 |
2.3. Antifungal Sensibility Test
Species | Designation | Source * | MIC (µg/µL) Sakuranetin ** |
---|---|---|---|
Candida dubliniensis | ATCC 7978 | ATCC | 0.63 (99%) |
Candida tropicalis | ATCC 13803 | ATCC | 0.63 (98%) |
Candida glabrata | ATCC 90030 | ATCC | 0.63 (99%) |
Candida parapsilosis | Clinical isolate 68 | CBMAI | 0.63 (98%) |
Candida krusei | Clinical isolate 9602 | CBMAI | 0.63 (99%) |
Candida albicans | CBMAI 560 | CBMAI | 0.32 (99%) |
Cryptococcus neoformans | KN99α (serotype A) | LIMIc | 0.32 (99%) |
Cryptococcus gattii | R265 (serotype B) | LIMIc | 0.32 (97%) |
Cryptococcus gattii | NIH312 (serotype C) | LIMIc | 0.32 (97%) |
Cryptococcus neoformans | JEC21 (serotype D) | LIMIc | 0.08 (98%) |
Saccharomyces cerevisiae | BY4742 | LIMIc | 0.32 (99%) |
3. Experimental
3.1. General Experimental Procedures
3.2. Plant Material
3.3. Extraction and Isolation
3.4. 5,4'-Dihydroxy-7-methoxyflavanone (sakuranetin)
3.5. X-ray Crystallography
3.6. Disk Diffusion Assay
3.7. Minimum Inhibitory Concentration
4. Conclusions
Acknowledgments
Author Contributions
Conflicts of Interest
References
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Dos S. Grecco, S.; Dorigueto, A.C.; Landre, I.M.; Soares, M.G.; Martho, K.; Lima, R.; Pascon, R.C.; Vallim, M.A.; Capello, T.M.; Romoff, P.; et al. Structural Crystalline Characterization of Sakuranetin — An Antimicrobial Flavanone from Twigs of Baccharis retusa (Asteraceae). Molecules 2014, 19, 7528-7542. https://doi.org/10.3390/molecules19067528
Dos S. Grecco S, Dorigueto AC, Landre IM, Soares MG, Martho K, Lima R, Pascon RC, Vallim MA, Capello TM, Romoff P, et al. Structural Crystalline Characterization of Sakuranetin — An Antimicrobial Flavanone from Twigs of Baccharis retusa (Asteraceae). Molecules. 2014; 19(6):7528-7542. https://doi.org/10.3390/molecules19067528
Chicago/Turabian StyleDos S. Grecco, Simone, Antônio C. Dorigueto, Iara M. Landre, Marisi G. Soares, Kevin Martho, Ricardo Lima, Renata C. Pascon, Marcelo A. Vallim, Tabata M. Capello, Paulete Romoff, and et al. 2014. "Structural Crystalline Characterization of Sakuranetin — An Antimicrobial Flavanone from Twigs of Baccharis retusa (Asteraceae)" Molecules 19, no. 6: 7528-7542. https://doi.org/10.3390/molecules19067528