title: A unique immuno-stimulant steroidal sapogenin acid from the roots of Asparagus racemosus.
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, D(cal)=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.
authors.affiliation: Natural Product Chemistry (Plants) Division, Indian Institute of Integrative Medicine, Canal Road, Jammu 180001 (J&K), CSIR, India.
authors.forename: Punita
authors.initials: P
authors.lastname: Sharma
authors.forename: Prashant S
authors.initials: PS
authors.lastname: Chauhan
authors.forename: Prabhu
authors.initials: P
authors.lastname: Dutt
authors.forename: Musarat
authors.initials: M
authors.lastname: Amina
authors.forename: Krishan A
authors.initials: KA
authors.lastname: Suri
authors.forename: Bishan D
authors.initials: BD
authors.lastname: Gupta
authors.forename: Om P
authors.initials: OP
authors.lastname: Suri
authors.forename: Kanaya L
authors.initials: KL
authors.lastname: Dhar
authors.forename: Deepak
authors.initials: D
authors.lastname: Sharma
authors.forename: Vivek
authors.initials: V
authors.lastname: Gupta
authors.forename: Naresh K
authors.initials: NK
authors.lastname: Satti
mesh_terms: D000276:Adjuvants, Immunologic / Q000008:administration & dosage* / Q000737:chemistry / Q000302:isolation & purification; D000818:Animals; D015703:Antigens, CD / Q000378:metabolism; D027761:Asparagus Plant / Q000737:chemistry*; D018360:Crystallography, X-Ray; D016572:Cyclosporine / Q000494:pharmacology; D016207:Cytokines / Q000378:metabolism; D016867:Immunocompromised Host; D007166:Immunosuppressive Agents / Q000494:pharmacology; D007978:Levamisole / Q000494:pharmacology; D051379:Mice; D015394:Molecular Structure; D010936:Plant Extracts / Q000008:administration & dosage* / Q000737:chemistry / Q000302:isolation & purification; D018517:Plant Roots / Q000737:chemistry*; D013150:Spirostans / Q000008:administration & dosage* / Q000737:chemistry / Q000302:isolation & purification; D013237:Stereoisomerism
chemical_list: C560401:21-nor-18,27-dimethyl-1,2,3-trihydroxy-25-spirost-4-en-19-oic acid; D000276:Adjuvants, Immunologic; D015703:Antigens, CD; D016207:Cytokines; D007166:Immunosuppressive Agents; D010936:Plant Extracts; D013150:Spirostans; D007978:Levamisole; D016572:Cyclosporine