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Helvetica Chimica Acta – Vol. 96 (2013)
(40 – 63 mm; Merck, Germany). Optical rotations: SEPA-3000 Automatic digital polarimeter. NMR
Spectra: Bruker-AM-400 and -DRX-500 instrument; in (D5)pyridine and (D6)DMSO with SiMe4 as
internal standard; d in ppm, J in Hz. FAB-MS (negative-ion mode) and HR-ESI-MS (negative-ion
mode): VG-AutoSpec-3000 and API-Qstar Pulsar LC/TOF spectrometers, resp; in m/z.
Plant Material. The dried leaves of Yucca elephantipes were collected from the East Garden of the
Kunming Botanical Garden, Chinese Academy of Sciences, Yunnan, P. R. China, on August, 2005. A
voucher specimen (KUN No. 0831640) has been deposited with the Herbarium of the Kunming Institute
of Botany, Chinese Academy of Sciences.
Extraction and Isolation. The dried leaves (3.8 kg) of Yucca elephantipes were extracted three times
with MeOH (each 5 l) under reflux for 2 h each time. After evaporation of the solvent, the residue was
suspended in H2O (5 l), and then partitioned with petroleum ether (each 1 l, 5 times), CHCl3 (each 1 l,
5 times), and BuOH (each 1 l, 5 times), successively. The BuOH fraction (150 g) was subjected to CC
(SiO2 (3700 g), CHCl3/MeOH/H2O 7:3 :0.5): Fractions 1 – 6. Fr. 1 (20 g) was subjected to CC (MCI gel
CHP-20P H2O/MeOH 1:0 ! 0 :1, then SiO2, CHCl3/MeOH/H2O 9 :1:0.1 ! 7:3 :0.5, and finally RP-8,
H2O/MeOH 4 :6 ! 0 :1): 1 (10 mg), 2 (6 mg), and 3 (8 mg). Fr. 2 (27 g) was applied to CC (MCI gel
CHP-20P, H2O/MeOH 1:0 ! 0 :1, then RP-8, H2O/MeOH, 6 :4 ! 0 :1, then Sephadex LH-20, H2O/
MeOH 1:0 ! 0 :1, and finally SiO2, CHCl3/MeOH/H2O 7:3 :0.5): 4 (31 mg) and 7 (170 mg). Fr. 4 (11 g)
was subjected to CC (Diaion HP-20, H2O/MeOH 1:0 ! 0 :1, then MCI gel CHP-20P, MeOH/H2O
2 :8 ! 1:0, and finally SiO2, CHCl3/MeOH/H2O 6 :4 :1): 6 (34 mg) and 10 (90 mg). Fr. 5 (20 g) was
applied to CC(MCI-gel CHP-20P, MeOH/H2O 0 :1 ! 1:0, then RP-8, MeOH/H2O 2 :8 ! 1:0), and
finally SiO2, CHCl3/MeOH/H2O 6 :4 :1): 5 (170 mg). Fr. 6 (14 g) was subjected to CC(MCI gel CHP-20P,
MeOH/H2O 0 :1 ! 1:0 and then SiO2, CHCl3/MeOH/H2O 6 :4 :1): 5 (450 mg), 8 (80 mg), and 9
(60 mg).
Elephanoside G (¼(3b,25S)-Spirost-5-en-3-yl O-b-d-Glucopyranosyl-(1 ! 3)-O-b-d-glucopyrano-
syl-(1 ! 4)-b-d-galactopyranoside; 1). White amorphous powder. [a]2D6 ¼ ꢀ35.9 (c ¼ 0.12, MeOH).
1H-NMR (C5D5N, 500 MHz): 0.80 (s, Me(18)); 0.83 – 0.86 (m, HꢀC(9)); 0.87 (s, Me(19)); 0.94 – 0.97 (m,
HaꢀC(1)); 0.99 – 1.03 (m, HaꢀC(12)); 1.03 – 1.06 (m, HꢀC(14)); 1.06 (d, J ¼ 7.0, Me(27)); 1.13 (d, J ¼ 6.9,
Me(21)); 1.29 – 1.31 (m, HaꢀC(7)); 1.32 – 1.34 (m, HaꢀC(24)); 1.36 – 1.38 (m, HaꢀC(15)); 1.39 – 1.41 (m,
HaꢀC(23)); 1.42 – 1.45 (m, HꢀC(11)); 1.49 – 1.53 (m, HꢀC(8)); 1.56 – 1.59 (m, HꢀC(25)); 1.64 – 1.67 (m,
HbꢀC(12)); 1.69 – 1.71 (m, HbꢀC(1)); 1.72 – 1.74 (m, HaꢀC(2)); 1.77 (dd, J ¼ 6.5, 8.5, HꢀC(17)); 1.84 – 1.86
(m, HbꢀC(7)); 1.87 – 1.89 (m, HbꢀC(23)); 1.91 – 1.93 (m, HꢀC(20)); 1.95 – 2.01 (m, HbꢀC(15)); 2.07 – 2.10
(m, HbꢀC(2)); 2.12 – 2.15 (m, HbꢀC(24)); 2.44 (t, J ¼ 11.5, HaꢀC(4)); 2.66 (dd, J ¼ 2.5, 11.5, HbꢀC(4));
3.35 (br. d, J ¼ 11.0, HaꢀC(26)); 3.89 – 3.92 (m, HꢀC(3)); 3.93 – 3.95 (m, Glc HꢀC(5’’’)); 4.03 (br. d, J ¼
11.0, HbꢀC(26)); 4.05 – 4.07 (m, Glc HꢀC(2’’’)); 4.08 – 4.10 (m, Gal HꢀC(5’)); 4.11 – 4.13 (m, Gal
HꢀC(3’)); 4.14 (t, J ¼ 8.0, Glc HꢀC(3’’)); 4.20 – 4.23 (m, Glc HꢀC(4’’’)); 4.45 – 4.48 (m, Gal HꢀC(2’));
4.49 – 4.52 (m, HꢀC(16)); 4.56 (br. s, Gal HꢀC(4’)); 4.90 (d, J ¼ 7.5, Gal HꢀC(1’)); 5.14 (d, J ¼ 7.8, Glc
HꢀC(1’’)); 5.22 (d, J ¼ 7.4, Glc HꢀC(1’’’)); 5.30 (d, J ¼ 4.5, HꢀC(6)). 13C-NMR (C5D5N, 125 MHz): Table.
FAB-MS (neg.): 899 ([M ꢀ H]ꢀ), 737 ([M ꢀ 162 ꢀ H]ꢀ), 575 ([M ꢀ 162 ꢀ 162 ꢀ H]ꢀ), 413 ([M ꢀ 162 ꢀ
162 ꢀ 162 ꢀ H]ꢀ). HR-ESI-MS (neg.): 899.4652 ([M ꢀ H]ꢀ, C45H71O1ꢀ8 ; calc. 899.4640).
Elephanoside H (¼(3b,5b,25R)-3-[(2-O-b-d-Glucopyranosyl-b-d-galactopyranosyl)oxy]spirostan-
1
12-one; 2). White amorphous powder. [a]2D3 ¼ ꢀ21.3 (c ¼ 0.46, MeOH). H-NMR (C5D5N, 400 MHz):
0.67 (d, J ¼ 5.0, Me(27)); 0.88 – 0.92 (m, HaꢀC(7)); 0.96 (s, Me(19)); 1.06 (s, Me(18)); 1.16 – 1.19 (m,
HbꢀC(7)); 1.31 (d, J ¼ 6.8, Me(21)); 1.40 – 1.43 (m, HꢀC(14)); 1.64 – 1.67 (m, HꢀC(25)); 1.68 – 1.69 (m,
HꢀC(9)); 1.82 – 1.84 (m, HꢀC(8)); 1.90 – 1.95 (m, HꢀC(20)); 2.17 (dd, J ¼ 4.8, 13.9, HaꢀC(11)); 2.19 – 2.25
(m, HꢀC(5)); 2.34 (t, J ¼ 13.9, HbꢀC(11)); 2.81 (dd, J ¼ 7.1, 8.1, HꢀC(17)); 3.49 (br. t, J ¼ 10.2, HaꢀC(26));
3.58 (br. d, J ¼ 10.2, HbꢀC(26)); 3.82 – 3.86 (m, Glc HꢀC(5’’)); 4.01 – 4.04 (m, Gal HꢀC(5’)); 4.21 (t, J ¼
8.6, Glc HꢀC(3’’)); 4.23 – 4.25 (m, HꢀC(3)); 4.09 (t, J ¼ 8.6, Glc HꢀC(2’’)); 4.25 (dd, J ¼ 2.6, 9.0, Gal
HꢀC(3’)); 4.33 (t, J ¼ 8.6, Glc HꢀC(4’’)); 4.52 – 4.54 (m, HꢀC(16)); 4.56 (d, J ¼ 2.6, Gal HꢀC(4’)); 4.67 (t,
J ¼ 9.0, Gal HꢀC(2’)); 4.88 (d, J ¼ 7.6, Gal HꢀC(1’)); 5.29 (d, J ¼ 7.6, Glc HꢀC(1’’)). 13C-NMR (C5D5N,
100 MHz): Table. FAB-MS (neg.): 753 ([M ꢀ H]ꢀ), 591 ([M ꢀ 162 ꢀ H]ꢀ). HR-ESI-MS (neg.): 753.4059
([M ꢀ H]ꢀ, C39H61O1ꢀ4 ; calc. 753.4061).
Acid Hydrolysis of 1 and the Determination of the Absolute Configuration of the Sugar Units. Saponin
1 (4 mg) was dissolved in 2m HCl/dioxane 1:1 (2 ml) and hydrolyzed at 958 for 6 h. The mixture was