TABLE 2

1H NMR data for the TFA salts of metabolites MII-1-5, -11, and -13

PositionMII-1aMII-2aMII-3bMII-4bMII-5aMII-11aMII-13a
δHa (J in Hz)δHb (J in Hz)δHa (J in Hz)
36.68 s6.69 s6.68 s7.20 s6.91 s
42.99 br d (14.1) 3.28 m3.01 br d (14.1) 3.27 mN.D.4.88 br s4.86c br s (W1/2= 6.7 Hz)5.24 br s (W1/2= 6.2 Hz)3.07 m, 3.26 m
53.49 m, 3.77 mN.D.N.D.N.D.3.68 br d (12.7), 3.62 m3.64 m, 3.43 m3.44 m, 3.83 m
6a4.35 mN.D.4.37 br d (15.6)4.22 br d (13.5)4.12 br d (12.6)4.34 m4.30 br d (15.5)
72.85 m, 3.47 m2.86 m, 3.47 mN.D.N.D.2.90 t (13.8), 2.85 m3.01 m, 3.07 m2.83 m 3.44 m
87.19 s7.20 s7.03 s6.98 s6.90 s6.91 s6.95 s
117.99 s8.02 s7.95 s8.16 s8.04 s7.65 s7.63 s
1-OCH2O-25.94 and 6.10 br s5.99 and 6.14 br s5.95 and 6.14 br s6.08 and 6.16 br s6.04 and 6.15 br s
9-OMe3.91 s3.88 s3.86 s3.86 s3.86 s
10-OMe3.85 s3.89 s3.83 s3.82 s
N-Me3.17 s3.17 s3.19 s3.18 s3.16 s3.17 s
GlcUA
    1″5.04 d (7.6)5.02 d (7.7)4.94 d (7.8)N.D.4.73 d (8.0)5.31 d (7.6)5.29 d (6.4)
    2′4′3.49–3.67 m3.49–3.65 m3.49–3.67 m3.49–3.673.48–3.67 m3.50–3.643.49 m (2′, 3′), 3.59 m (4′)
    5′3.93 d (10.4)3.93 d (9.5)3.96 d (9.7)3.98 d (10.2)3.99 d (9.7)3.88 d (9.5)3.85 d (9.5)
    1″4.95 d (7.6)
    5″3.94 d (10.4)
Glc
    1″4.90 d (7.7)
    6″3.75 dd (5.2, 12.1), 3.85 dd (2.3, 12.1)
  • N.D., not detected.

  • a Data were obtained from direct NMR measurement (600 MHz, MeOH-d4).

  • b Data were obtained from online HPLC-SPE-NMR.

  • c Signals were buried in DOH and were picked up from a 1D selective total correlation spectroscopy experiment.