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A unique immuno-stimulant steroidal sapogenin acid from the roots of Asparagus racemosus
Authors:Sharma Punita  Chauhan Prashant S  Dutt Prabhu  Amina Musarat  Suri Krishan A  Gupta Bishan D  Suri Om P  Dhar Kanaya L  Sharma Deepak  Gupta Vivek  Satti Naresh K
Institution:a Natural Product Chemistry (Plants) Division, Indian Institute of Integrative Medicine, Canal Road, Jammu 180001 (J&K), CSIR, India
b Cell Biology Lab., Pharmacology Division, Indian Institute of Integrative Medicine, Canal Road, Jammu 180001 (J&K), CSIR, India
c Post-Graduate Department of Physics, University of Jammu, Jammu 180006 (J&K), India
Abstract:A new steroidal sapogenin molecule 1 having unique characteristics, 21-nor and unusual C19 carboxylic acid has been isolated from the roots of Asparagus racemosus. On the basis of chemical evidence, extensive spectroscopic analysis including two dimensional (2D) NMR and X-ray studies of single crystal, the structure of 1 was determined as (1S,2R,3S,8S,9S,10S,13S,14S,16S,17R,22R,25R)-21-nor-18β,27α-dimethyl-1β,2β,3β-trihydroxy-25-spirost-4-en-19β-oic acid. 1 crystallizes in monoclinic space group P21 with a = 9.295(2), b = 11.238(2), c = 11.376(2) Å; β = 91.993(4)°, Z = 2, Dcal = 1.344 Mg/m3. The structure was solved by direct methods and refined by full-matrix least-squares procedure to a final R-value of 0.0561 for 4064 observed reflections. 1 was tested against the type of immune responses generated during treatment in normal and immune-suppressed animals and detailed biological activity evaluation suggests it to be a potent immunostimulator.
Keywords:Asparagus racemosus  Steroidal sapogenin  X-ray crystallography  Restraint stress  Immunostimulation  Cyclosporin-A
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