Phytochemical and pharmacological studies on the seeds of Centratherum anthelminticum

School of Studies in Chemistry and Biochemistry, Vikram University, Ujjain-456 010,

Madhya Pradesh, India

E-mail : bkmehta11@yahoo.com, drdarshana31@gmail.com

Green Technology Department, Ipca Laboratories Limited, Ratlam-457 002, Madhya Pradesh, India

Manuscript received 20 February 2014, accepted 12 March 2014

One new and two known glycosides were isolated from the seeds of Centratherum anthelminticum. The new pentacyclic triterpenoid saponin was shown to contain caulophyllogenin and seven sugar residues forming three glycosyl chains. The structural analysis of its acetylated derivative was determined using a combination of homo-(1D ¹H NMR, ¹³C NMR and ¹³C NMR-DEPT) and heteronuclear 2D NMR techniques (¹H-¹H-COSY, ¹H-¹H-TOCSY, HMQC and HMBC), ESIMS and chemical methods. The structure of the saponin was established as 3-O-β-D-glucopyranosyl-(1→2)- α-L-rhamnopyranosyl-(1→2)-[α-L-arabinopyranosyl-(1→5)]-β-D-glucuronopyranosyl-28-O-β-D-xylopyranosyl-(1→3)-α-L-rhamnopyranosyl-(1→3)-β-D-glucopyranosyl]-16α,23-acetoxyolean-12-en-28-oic acid. The other compounds β-sitosterol-3- O-glucopyranoside and 3-O-[β-D-glucopyranosyl-(1→3)-α-L-rhamnopyranosyl-(1→2)-α-L-arabinopyranosyl]-hederagenin were also isolated from the methanol extract of seeds. Different extracts and compounds were also tested for antifilarial, antimicrobial and cytotoxic activities. Methanolic and aqueous extracts of seeds exhibited some pronounced pharmacological activities under study.