Molecules 2017, 22, 81; doi:10.
3390/molecules22010081 S1 of S7
Supplementary Materials: Microbial Glycosylation of
Daidzein, Genistein and Biochanin A. Two New
Glucosides of Biochanin A
Sandra Sordon, Jarosław Popłoński, Tomasz Tronina and Ewa Huszcza
List of contents:
1. NMR spectra of compounds obtained by biotransformation with the use of Absidia coerulea AM 93
strain indicating the mixture of products: 7-O-β-D-glucopyranosyl-5-hydroxy-4′-methoxyisoflavone
(sissotrin) and 5-O-β-D-glucopyranosyl-7-hydroxy-4′-methoxyisoflavone (isosissotrin).
Figures S1–S2: 1H-NMR (600 MHz, CD3OD) spectra.
Figure S3: COSY (150 MHz, CD3OD) spectra.
Figure S4: 13C-NMR (150 MHz, CD3OD) spectra.
Figures S5–S7: HSQC (150 MHz, CD3OD) spectra.
Figures S8–S11: HMBC (150 MHz, CD3OD) spectra.
Figure S12: 13C-NMR (150 MHz, CD3OD) superimposed spectra of sissotrin and mixture of
sissotrin and isosissotrin.
2. Negative-ion HR-ESIMS spectra of mixture of 7-O-β-D-glucopyranosyl-5-hydroxy-4′-
methoxyisoflavone (sissotrin) and 5-O-β-D-glucopyranosyl-7-hydroxy-4′-methoxyisoflavone
(isosissotrin) obtained by biotransformation by Absidia coerulea AM 93.
Figure S13: HR-ESIMS spectrum.
Figure S1. 1H-NMR (600 MHz, CD3OD) spectra of mixture of sissotrin and isosissotrin obtained by
biotransformation by Absidia coerulea AM 93.
Molecules 2017, 22, 81; doi:10.3390/molecules22010081 S2 of S7
Figure S2. 1H-NMR (600 MHz, CD3OD) spectra of the aromatic region of sissotrin (A) and isossisotrin
(B) mixture obtained by biotransformation by Absidia coerulea AM 93.
Figure S3. COSY (150 MHz, CD3OD) spectra of mixture of sissotrin and isosissotrin obtained by
biotransformation by Absidia coerulea AM 93.
Molecules 2017, 22, 81; doi:10.3390/molecules22010081 S3 of S7
Figure S4. 13C-NMR (150 MHz, CD3OD) spectra of mixture of sissotrin and isosissotrin obtained by
biotransformation by Absidia coerulea AM 93.
Figure S5. HSQC (150 MHz, CD3OD) spectra of mixture of sissotrin and isosissotrin obtained by
biotransformation by Absidia coerulea AM 93.
Molecules 2017, 22, 81; doi:10.3390/molecules22010081 S4 of S7
Figure S6. HSQC (150 MHz, CD3OD) spectra of mixture of sissotrin and isosissotrin (correlations of
aromatic A-ring protons: H-6 and H-8) obtained by biotransformation by Absidia coerulea AM 93.
Figure S7. HSQC (150 MHz, CD3OD) spectra of mixture of sissotrin and isosissotrin (correlations of
H-1″ protons) obtained by biotransformation by Absidia coerulea AM 93.
Molecules 2017, 22, 81; doi:10.3390/molecules22010081 S5 of S7
Figure S8. HMBC (150 MHz, CD3OD) spectra of mixture of sissotrin and isosissotrin obtained by
biotransformation by Absidia coerulea AM 93.
Figure S9. HMBC (150 MHz, CD3OD) spectra of mixture of sissotrin and isosissotrin (correlations of
aromatic A-ring protons-H-6 and H-8) obtained by biotransformation by Absidia coerulea AM 93.
Molecules 2017, 22, 81; doi:10.3390/molecules22010081 S6 of S7
Figure S10. HMBC (150 MHz, CD3OD) spectra of mixture of sissotrin and isosissotrin (correlations of
H-1″ protons) obtained by biotransformation by Absidia coerulea AM 93.
Figure S11. HMBC correlations for sissotrin and isosissotrin obtained by biotransformation by
Absidia coerulea AM 93.
Molecules 2017, 22, 81; doi:10.3390/molecules22010081 S7 of S7
Figure S12. 13C-NMR (150 MHz, CD3OD) spectra of sissotrin (obtained by biotransformation by
Absidia glauca AM 177 (1) and by Rhizopus nigricans UPF 701 * (2)) and mixture of sissotrin and
isosissotrin obtained by biotransformation by Absidia coerulea AM 93 (3). Arrows indicated selected
carbon signals of sissotrin. On the NMR spectra of products obtained by biotransformation by
Absidia coerulea AM 93 those carbon signals are doubled. * Result not included in this paper.
Figure S13. Negative-ion HR-ESIMS spectra of mixture of sissotrin and isosissotrin obtained by
biotransformation by Absidia coerulea AM 93.
