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Acta Crystallographica Section E

Structure Reports
Online
ISSN 1600-5368

Guggulsterone E, a lipid-lowering agent from Commiphora mukul

Sanjay Sarkhel, Umesh Yadava, Prem Prakas, Girish K. Jain, Satywan Singh and
Prakash R. Maulik

Copyright © International Union of Crystallography

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Acta Cryst. (2001). E57, o285–o286 Sanjay Sarkhel et al.  C21 H28 O2
 organic papers
Acta Crystallographica Section E
Structure Reports
Guggulsterone E, a lipid-lowering agent from
Online Commiphora mukul
ISSN 1600-5368

Sanjay Sarkhel,a Umesh Yadava,a The crystal structure of the title compound [4,17(20)-(cis)- Received 6 February 2001
pregnadiene-3,16-dione, C21H28O2] shows that the two mol- Accepted 14 February 2001
Prem Prakas,b Girish K. Jain,b Online 28 February 2001
Satywan Singhb and Prakash R. ecules in the asymmetric unit have similar conformations. The
Maulika* fused-ring system contains one sofa, two chairs and one CDRI communication
envelope. Weak intermolecular CÐH


O hydrogen bonds, No. 6135.
a
Membrane Biology Division, Central Drug together with van der Waals interactions, stabilize the
Research Institute, Lucknow 226 001, India, and
b
structure.
Division of Pharmaceutics, Central Drug
Research Institute, Lucknow 226 001, India
Comment
Correspondence e-mail:
Guggulsterone E, an active constituent of an ayurvedic drug
maulik_prakas@yahoo.com
guggulip derived from Commiphora mukul (Verma et al.,
1998), possesses a signi®cant cholesterol and lipid-lowering
activity. It has been marketed in India as a hypolipidaemic
Key indicators drug. In view of its potential medicinal importance, the present
Single-crystal X-ray study study of the title compound, (I), was undertaken to determine
T = 293 K the conformation of its steroid nucleus.
Mean (C±C) = 0.011 A Ê
R factor = 0.063
wR factor = 0.237
Data-to-parameter ratio = 8.4

For details of how these key indicators were

automatically derived from the article, see
http://journals.iucr.org/e.

The X-ray diffraction study of (I) shows that the asymmetric

unit contains two molecules of similar conformations and the
structure of one molecule with the atomic numbering scheme
is shown in Fig. 1. The molecule contains one fused-ring
system (A/B/C/D) and ®ve chiral centres. The torsion angles
(Table 1) and least-squares-plane calculations indicate that, in
both the molecules in the asymmetric unit, ring A is in a
distorted sofa conformation, while rings B and C adopt a
puckered and nearly a chair conformation, respectively. Ring
D adopts an envelope conformation. The ring systems B/C and
C/D are trans-fused with each other.
Based on literature precedence (Hill et al., 1991), the
pregnane steroids have C10-substituents in a -orientation.
# 2001 International Union of Crystallography
Printed in Great Britain ± all rights reserved
Acta Cryst. (2001). E57, o285±o286
Accordingly, the methyl groups at C10 and C13 have -axial
orientation in both the molecules in the asymmetric unit. The
shorter bond lengths C3ÐC4/C33ÐC34 1.453 (12)/
1.428 (11) AÊ and C16ÐC17/C46ÐC47 1.470 (11)/1.500 (12) A Ê
are indicative of possible double-bond conjugation. The
torsion angles C16ÐC17ÐC18ÐC19 ÿ174.5 (7) and C46Ð
C47ÐC48ÐC49 ÿ177.8 (7) indicate that the title compound
is the E-isomer of guggulsterone. The crystal structure analysis
reveals the presence of weak intermolecular CÐH


O
DOI: 101107/S1600536801003142 Sanjay Sarkhel et al.  C21H28O2 o285
electronic reprint
organic papers
interactions (Table 2) which, along with the van der Waals
forces, stabilize the solid-state structure.

Experimental
Guggulsterone E was isolated by column chromatography of the
ethyl acetate extract from Commiphora mukul following the avail-
able protocol (Patil et al., 1972). Diffraction-quality crystals were
grown by slow evaporation of a methanol solution at room
temperature.
Crystal data
C21H28O2 Dx = 1.170 Mg mÿ3
Mr = 312.44 Mo K radiation
Monoclinic, P21 Cell parameters from 50
a = 7.4634 (11) AÊ re¯ections
Ê
b = 13.747 (2) A  = 2.3±12.3
Ê
c = 17.352 (3) A  = 0.07 mmÿ1 Figure 1
 = 94.862 (12) T = 293 (2) K The molecular structure of (I) with labelling of the non-H atoms and
V = 1773.8 (5) AÊ3 Needle, colourless displacement ellipsoids at the 50% probability level.
Z=4 0.35  0.25  0.20 mm

Data collection
Bruker P4 diffractometer h = ÿ1 ! 8
±2 scans k = ÿ16 ! 1 Table 2
4388 measured re¯ections l = ÿ20 ! 20 Ê ,  ).
Hydrogen-bonding geometry (A
3522 independent re¯ections 3 standard re¯ections
2257 re¯ections with I > 2(I) every 97 re¯ections DÐH


A DÐH H


A D


A DÐH


A
Rint = 0.031 frequency: 60 min i
C21ÐH21C


O2 0.96 2.745 3.625 (10) 153
max = 25.0 intensity decay: none
C21ÐH21B


O31i 0.96 2.813 3.723 (10) 159
Re®nement C32ÐH32B


O2ii 0.97 2.453 3.237 (10) 138
C45ÐH45A


O1iii 0.97 2.425 3.274 (11) 146
Re®nement on F 2 w = 1/[ 2(Fo2) + (0.1494P)2 C50ÐH50B


O32iii 0.96 2.759 3.641 (10) 153
R[F 2 > 2(F 2)] = 0.063 + 1.4424P] C51ÐH51B


O1iii 0.96 2.725 3.678 (12) 172
wR(F 2) = 0.237 where P = (Fo2 + 2Fc2)/3
Symmetry codes: (i) 1 ÿ x; 12 ‡ y; 1 ÿ z; (ii) x ÿ 1; y; z; (iii) 1 ÿ x; y ÿ 12; 2 ÿ z.
S = 0.92 (
/)max < 0.001
3522 re¯ections
max = 0.20 e A Ê ÿ3
421 parameters
min = ÿ0.20 e A Ê ÿ3 All H atoms were placed in idealized positions geometrically and
H-atom parameters constrained Absolute structure: Flack (1983) allowed to ride on their parent atoms. The present study does not
Flack parameter = ÿ1 (4)
establish the absolute con®guration of the title molecule, and it is not
known from other work. There are only 281 Friedel pairs, and the
anomalous scattering effects are negligible.
Data collection: XSCANS (Siemens, 1996); cell re®nement:
Table 1
Selected torsion angles ( ). XSCANS; data reduction: XSCANS; program(s) used to solve
structure: SHELXTL-NT (Bruker, 1997); program(s) used to re®ne
C10ÐC1ÐC2ÐC3 ÿ52.0 (8) C32ÐC33ÐC34ÐC35 ÿ4.6 (12) structure: SHELXTL-NT; molecular graphics: NRCVAX (Gabe et
C1ÐC2ÐC3ÐC4 29.3 (10) C33ÐC34ÐC35ÐC40 ÿ4.7 (12)
C2ÐC3ÐC4ÐC5 ÿ1.3 (13) C40ÐC35ÐC36ÐC37 ÿ54.2 (9)
al., 1989) and ORTEP (Johnson, 1965); software used to prepare
C3ÐC4ÐC5ÐC10 ÿ4.6 (13) C35ÐC36ÐC37ÐC38 54.4 (9) material for publication: SHELXTL-NT.
C10ÐC5ÐC6ÐC7 ÿ48.0 (10) C36ÐC37ÐC38ÐC39 ÿ54.9 (8)
C5ÐC6ÐC7ÐC8 52.5 (9) C37ÐC38ÐC39ÐC40 56.8 (8)
C6ÐC7ÐC8ÐC9 ÿ56.8 (8) C32ÐC31ÐC40ÐC50 ÿ75.4 (8) SS thanks CSIR (India) for an SRF award.
C7ÐC8ÐC9ÐC10 58.3 (7) C32ÐC31ÐC40ÐC35 45.4 (8)
C2ÐC1ÐC10ÐC5 45.3 (8) C34ÐC35ÐC40ÐC31 ÿ15.8 (10) References
C2ÐC1ÐC10ÐC20 ÿ72.9 (8) C36ÐC35ÐC40ÐC39 50.9 (8)
C4ÐC5ÐC10ÐC1 ÿ17.5 (10) C38ÐC39ÐC40ÐC35 ÿ52.0 (7) Bruker (1997). SHELXTL-NT. Version 5.1. Bruker AXS Inc., Madison,
C6ÐC5ÐC10ÐC9 45.3 (8) C41ÐC42ÐC43ÐC51 ÿ68.0 (8) Wisconsin, USA.
C8ÐC9ÐC10ÐC5 ÿ50.8 (7) C47ÐC43ÐC44ÐC45 38.1 (7) Flack, H. D. (1983). Acta Cryst. A39, 876±881.
C11ÐC12ÐC13ÐC21 ÿ67.0 (8) C43ÐC44ÐC45ÐC46 ÿ38.0 (8) Gabe, E. J., Le Page, Y., Charland, J. ±P., Lee, F. L. & White, P. S. (1989). J.
C17ÐC13ÐC14ÐC15 40.0 (6) C44ÐC45ÐC46ÐC47 22.2 (8) Appl. Cryst. 22, 384±387.
C13ÐC14ÐC15ÐC16 ÿ36.8 (7) C45ÐC46ÐC47ÐC43 1.2 (8) Hill, R. A., Kirk, D. N., Makin, H. L. J. & Murphy, G. M. (1991). Dictionary of
C14ÐC15ÐC16ÐC17 19.7 (8) C44ÐC43ÐC47ÐC46 ÿ23.5 (7) Steroids. London: Chapman and Hall.
C15ÐC16ÐC17ÐC13 5.6 (8) C46ÐC47ÐC48ÐC49 ÿ177.8 (7) Johnson, C. K. (1965). ORTEP. Report ORNL-3794. Oak Ridge National
C14ÐC13ÐC17ÐC16 ÿ27.8 (6) H9ÐC9ÐC8ÐH8 ÿ178
Laboratory, Tennessee, USA.
C16ÐC17ÐC18ÐC19 ÿ174.5 (7) H39ÐC39ÐC38ÐH38 ÿ179
C40ÐC31ÐC32ÐC33 ÿ54.8 (9) C21ÐC13ÐC14ÐH14 176
Patil, V. D., Nayak, U. R. & Dev, S. (1972). Tetrahedron, 28, 2341±2352.
C31ÐC32ÐC33ÐC34 33.3 (10) C51ÐC43ÐC44ÐH44 176 Siemens (1996). XSCANS. Version 2.21. Siemens Analytical X-ray Instru-
ments Inc., Madison, Wisconsin, USA.
Verma, N., Singh, S. K. & Gupta, R. C. (1998). J. Chromatogr. B, 708, 243±248.

o286 Sanjay Sarkhel et al.  C21H28O2 Acta Cryst. (2001). E57, o285±o286
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