| Article ID | Journal | Published Year | Pages | File Type |
|---|---|---|---|---|
| 2029348 | Steroids | 2011 | 7 Pages |
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.
Research highlights▶ A new sapogenin 1, having 21-nor and C19 carboxylic acid characteristics,isolated from A. racemosus. ▶ 1 was identified as 21-nor-18β,27α-dimethyl-1β,2β,3β-trihydroxy-25-spirost-4-en-19β-oic acid. ▶ Crystallography of 1 confirmed conformation of rings (B,C,F) as chair, A as half chair and E as envelop. ▶ Compound 1 showed promising immunostimulatory activity in experimental animals.
