9
ꢀ,19-Cyclolanost-12,24E-dien-1ꢁ,3ꢀ,6ꢁ,16ꢀ,27-pentaol (cyclotanogenin, 2). White crystals, mp 249–252°C
ꢅ1
13
(
MeOH). IR spectrum (KBr, ꢄ, cm ): 3600–3200 (OH), 3040 (cyclopropane-ring CH ). Table 2 lists the C NMR spectral
data. FAB-MS m/z 475.674 [M + H] (calcd for C H O , 475.535).
2
+
2
9 47 5
Alkaline Hydrolysis of 1. Compound 1 (12 mg) was hydrolyzed by KOH solution (0.5%) at 25°C for 1 h. The
reaction mixture was neutralized and purified over a column of SiO to afford 3.
2
9
ꢀ,19-Cyclolanost-12,24E-dien-1ꢁ,3ꢀ,6ꢁ,16ꢀ,27-pentaol-O-ꢀ-D-galactopyranoside (3). White crystals, mp 277–
80°C (MeOH). IR spectrum (KBr, ꢄ, cm ): 3580–3200 (OH), 3043 (cyclopropane-ring CH ). Table 2 lists the C NMR
ꢅ1
13
2
2
+
spectral data. FAB-MS m/z 637.815 [M + H] (calcd for C H O , 637.8157).
3
5 57 10
3
-O-L-Rhamnopyranosyl-(1ꢃ2)-O-ꢀ-D-xylopyranosyl-(1ꢃ2)-O-ꢀ-D-glucuronopyranosyl-soyasapogenol B
2
0
(
astragaloside VIII) (4). White crystals, mp 222–224°C (MeOH), [ꢁ] ꢅ17.3° (c 0.4, EtOH–H O, 1:1). IR spectrum (KBr,
ꢄ, cm ): 3410 (OH), 1726. Í NMR spectrum (400 MHz, CD OD, ꢆ, ppm, J/Hz): 1.64 (m, H -1), 1.02 (m, H -1), 2.15 (m,
D 2
–
1
1
3
a
b
H -2), 1.82 (m, H -2), 3.32 (dd, J = 8.6, 3.1, H-3), 0.95 (m, H-5), 1.63 (m, H -6), 1.38 (m, H -6), 1.57 (m, H -7), 1.41 (m,
a
b
a
b
a
H -7), 1.58 (m, H-9), 1.88 (m, H-11), 5.24 (br.s, H-12), 1.78 (m, H -15), 1.04 (m, H -15), 1.75 (m, H -16), 1.32 (m, H -16),
b
a
b
a
b
2
.05 (dd, J = 13.6, 3.8, H-18), 1.74 (m, H -19), 0.96 (m, H -19), 1.44 (m, H -2), 1.33 (m, H -21), 3.39 (m, H-22), 1.20 (3H, s,
a b a b
Me-23), 1.23 (3H, s, Me-24), 0.89 (3H, s, Me-25), 0.98 (3H, s, Me-26), 1.13 (3H, s, Me-27), 0.83 (3H, s, Me-28), 0.92 (3H, s,
Me-29), 1.02 (3H, s, Me-30), 1.27 (3H, d, J = 6.4, Rha Me), 5.19 (d, J = 8.1, GlcA H-1ꢂ), 4.92 (d, J = 7.6, Xyl H-1ꢂꢂ), 4.12 (d,
1
3
J = 1.2, Rha H-1ꢂꢂꢂ). C NMR spectrum (100 MHz, CD OD, ꢆ, ppm): 39.6 (C-1), 26.8 (C-2), 91.9 (C-3), 44.5 (C-4), 57.4
3
(
(
C-5), 19.2 (C-6), 34.2 (C-7), 40.6 (C-8), 48.8 (C-9), 37.0 (C-10), 24.7 (C-11), 122.3 (C-12), 144.6 (C-13), 43.3 (C-14), 26.5
C-15), 29.9 (C-16), 38.4 (C-17), 46.4 (C-18), 47.4 (C-19), 31.4 (C-20), 42.1 (C-21), 76.8 (C-22), 63.6 (C-23), 22.8 (C-24),
1
(
7
6.1 (C-25), 17.3 (C-26), 25.2 (C-27), 20.2 (C-28), 32.3 (C-29), 28.9 (C-30), 105.1 (Glc A C-1ꢂ), 78.3 (C-2ꢂ), 78.8 (C-3ꢂ), 73.6
C-4ꢂ), 77.5 (C-5ꢂ), 169.6 (C-6ꢂ), 100.5 (Xyl C-1ꢂꢂ), 79.4 (C-2ꢂꢂ), 78.5 (C-3ꢂꢂ), 70.3 (C-4ꢂꢂ), 66.7 (C-5ꢂꢂ), 100.7 (Rha C-1ꢂꢂꢂ),
0.9 (C-2ꢂꢂꢂ), 70.7 (C-3ꢂꢂꢂ), 72.8 (C-4ꢂꢂꢂ), 68.1 (C-5ꢂꢂꢂ), 16.9 (C-6ꢂꢂꢂ).
ACKNOWLEDGMENT
We thank Drs. V. D. Mshvildadze and A. Picette (Department of Fundamental Sciences, University of Quebec,
Chicoutimi, Canada for assistance in determining the NMR spectra.
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1
2
.
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