ISSN:
1572-8854
Keywords:
C28-Steroidal lactone
;
ergostane derivatives
;
antineo plastic activity
Source:
Springer Online Journal Archives 1860-2000
Topics:
Geosciences
,
Physics
Notes:
Abstract The withanolide Withaperuvin E, C28H36O8, has been obtained from the air dried roots of Physalis peruviana and purified by silica gel chromatography. This compound exhibits significant antineo plastic activity. Prismatic pale yellow crystals were obtained from a methanol/acetone solution. The compound crystallizes together with a partially occupied [40(1)%] acetic acid molecule, in space group P212121, Z = 4, D c = 1.242 g cm−3, with unit, cell parameters a = 11.431(3), b = 14.104(1), c = 17.387(5)Å, V = 2803.2(11)Å3, and μ(CuKα) = 0.072mm−1. Through the X-ray analysis the molecule was found to be comprised of a steroidal skeleton with a β-oriented oxygen bridging atoms C(5) and C(6) in ring B. Steroid ring conformations are: A sofa; B sofa; C chair; D intermediate half-chair/sofa; the lactone ring E has a sofa conformation. All rings of the steroid skeleton are trans connected. The absolute configuration of the Withaperuvin E skeleton corresponds to that of naturally occurring steroids, C(18) and C(19) both being β-oriented. The partially occupied acetic acid molecule forms a hydrogen bond to the steroid molecule. Hydrogen bonding also occurs between OH(14) and a symmetry related oxygen O(20) of the steroid.
Type of Medium:
Electronic Resource
URL:
http://dx.doi.org/10.1023/A:1023204408338
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