Chemistry of Natural Compounds, Vol. 48, No. 3, July, 2012 [Russian original No. 3, May-June, 2012]
STEROID COMPOUNDS FROM STEMS OF Yucca gloriosa
M. M. Benidze, A. V. Skhirtladze, and E. P. Kemertelidze*
UDC 547.918
We studied previously the chemical composition of Yucca gloriosa L. (Spanish bayonet) introduced into Georgia on
an industrial scale. Several dozen steroid glycosides, derivatives of various aglycons, were isolated from leaves, flowers, and
rhizomes. The steroidal sapogenin tigogenin from the leaves was recommended as raw material for synthesizing steroidal
hormonal drugs [1, 2]. Dried leaves on the lower tier of the living plant that consisted mainly of spirostanol glycosides were
a source of the proposed fungicidal drug Gloriofucin [3]. Total steroidal saponins of flowers were called Alexin and were an
effective stimulator of the growth and development of agricultural crops [4]. Glycosides from the plant rhizomes exhibited the
same activity [5].
In continuation of studies of Y. gloriosa, herein we communicate results from a study of steroids from the stems,
which make up about 35% of the total plant mass.
Stems of Y. gloriosa that were collected at the Tbilisi Medicinal Plant Experimental Plot of Kutateladze Pharmaceutical
Chemistry Institute were peeled, ground, and dried. Raw material (300 g) was extracted with refluxing MeOH (70%). The
MeOH was distilled off. The precipitate that formed in the aqueous liquid upon cooling was filtered off and recrystallized
from MeOH to afford a white crystalline powder (0.1 g) that gave a reaction for steroidal glycosides of the spirostanol series
2
0
[
6]. The compound melted at 302–306°C, [ꢀ] –27.0° (c 1.0, CHCl ). It gave a single spot on TLC at the level of an authentic
D 3
sample of yuccaloeside A. A mixed sample with it did not cause melting-point depression. Acid hydrolysis formed the
aglycon with mp 185–188°C. Its physicochemical properties were identical to those of smilagenin. The monosaccharide part
of the hydrolysate contained D-glucose and D-galactose.
The glycoside was characterized as 25R,5ꢁ-spirostan-3ꢁ-ol 3-O-ꢁ-D-glucopyranosyl-(1ꢂ2)-ꢁ-D-galactopyranoside
and was yuccaloeside A, which was first isolated by us from leaves of Y. aloifolia [7].
The aqueous liquid remaining after the separation of yuccaloeside A was purified of lipophilic substances by a small
amount of CHCl and extracted exhaustively with water-saturated n-BuOH. The solvent was distilled off to afford total
3
steroidal saponins as an amorphous yellow powder (24 g, 8% of starting raw material) that contained at least 15 glycosides of
the spiro- and furostanol series according to TLC.
At this stage, we limited ourselves to studying only the composition of the stem sapogenins.
The BuOH extract (6 g) was hydrolyzed with HCl (8%) in the presence of benzene [8] to obtain total sapogenins
consisting of four components. The total sapogenins (1.4 g) were chromatographed over a column of Al O (1:20 ratio).
2
3
From the first petroleum-ether effluents isolated sapogenin 1; from subsequent petroleum-ether–benzene (7:3 and 2:8),
sapogenins 2 and 3; and from the final benzene:CHCl (3:2), sapogenin 4.
3
The sapogenins were recrystallized from MeOH to afford white crystals of 1 (0.14 g), 2 (0.07), 3 (0.07 ), and 4 (0.06).
2
0
–1
Sapogenin 1, mp 186–188°C, [ꢀ] –65° (c 1.0, CHCl ). IR spectrum (ꢃ, cm ): 3386 (OH), 1272, 1218, 987, 918,
D
3
9
00, 848; intensity 900>918 (25R-configuration). A mixed sample with authentic smilagenin did not show mp depression.
2
0
The sapogenin acetate was prepared {mp 148–150°C, [ꢀ]D –61° (c 1.0, CHCl )}. Sapogenin 1 was identified as smilagenin,
3
5
ꢁ,25R-spirostan-3ꢁ-ol [9–11].
Sapogenin 2, mp 201–203°C, [ꢀ] –68° (c 1.0, CHCl ). IR spectrum (ꢃ, cm ): 3378, 1079, 1041, 979, 956, 922,
2
0
–1
D
3
2
0
9
02, 864; 902>922 (25R-configuration). Sapogenin acetate: mp 206–208°C, [ꢀ] –75° (c 1.0, CHCl ). The TLC mobility
D
3
and physicochemical properties of sapogenin 2 corresponded with tigogenin, 5ꢀ,25R-spirostan-3ꢁ-ol [9–11].
2
0
–1
Sapogenin 3, mp 265–268°C, [ꢀ]D +8° (c 1.0, CHCl ). IR spectrum (ꢃ, cm ): 3394, 1712, 1241, 968, 918, 902,
3
2
0
8
60; 902>918 (25R-configuration). Sapogenin acetate: mp 244–245°C, [ꢀ]D –2° (c 1.0, CHCl ). The TLC mobility and
3
physicochemical properties corresponded with gekogenin, 5ꢀ,12-keto,25R-spirostan-3ꢁ-ol [9–11].
I. G. Kutateladze Institute of Pharmaceutical Chemistry, Tbilisi, 0159, Georgia, e-mail: ether_kemertelidze@yahoo.com.
Translated from Khimiya Prirodnykh Soedinenii, No. 3, May–June, 2012, pp. 464–465. Original article submitted November
1
8, 2011.
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0009-3130/12/4803-0518 ©2012 Springer Science+Business Media, Inc.
Benidze
