Steroidal saponins from the roots of Asparagus racemosus Patricia Y. Hayes a , Aisyah H. Jahidin a , Reg Lehmann b , Kerry Penman b , William Kitching a , James J. De Voss a, * a Department of Chemistry, SMMS, The University of Queensland, Brisbane, Qld. 4072, Australia b MediHerb Research Laboratories, Brisbane Technology Park, Qld. 4113, Australia Received 7 June 2007; received in revised form 30 August 2007 Available online 23 October 2007 Abstract Five steroidal saponins, shatavarins VI–X, together with five known saponins, shatavarin I (or asparoside B), shatavarin IV (or aspar- inin B), shatavarin V, immunoside and schidigerasaponin D5 (or asparanin A), have been isolated from the roots of Asparagus racemosus by RP-HPLC and characterized by spectroscopic (1D and 2D NMR experiments) and spectrometric (LCMS) methods. Ó 2007 Elsevier Ltd. All rights reserved. Keywords: Saponins; Shatavarins; Asparagus racemosus; Asparagaceae; NMR 1. Introduction Asparagus racemosus, commonly known as Shatavari, is found in forests throughout India, especially in the North of India and is cultivated for both medicinal and ornamen- tal purposes. The tuberous root of A. racemosus is used in traditional Indian medicine as a galactologue and for the treatment of diverse ailments including dysentery, tumors, inflammations, neuropathy, nervous disorders, bronchitis, hyperacidity, certain infectious diseases (Goyal et al., 2003), conjunctivitis (Sharma and Singh, 2002), spasm, chronic fevers, and rheumatism (Capasso et al., 2003). Pharmacological studies with animals have manifested the potency of A. racemosus extract as an antioxidant (Parihar and Hemnani, 2004; Kamat et al., 2000), antiana- phylactic (Padmalatha et al., 2002), adaptogen (Rege et al., 1999; Bhattacharya et al., 2000), antistress (Bhattacharya et al., 2002; Muruganandam et al., 2002), antiulcer (De et al., 1997; Goel and Sairam, 2002; Datta et al., 2002; Sai- ram et al., 2003), antidiarrhoeal (Venkatesan et al., 2005), antibacterial (Mandal et al., 2000a), antitussive (Mandal et al., 2000b), molluscicide (Chifundera et al., 1993) and radioprotective agent (Arora et al., 2005), and as a sub- strate for inulinase production (Singh et al., 2006), with the biggest focus being on its ability in modulating the immune system (Thatte et al., 1987; Thatte and Dahanu- kar, 1988; Rege et al., 1989; Rege and Dahanukar, 1993; Dhuley, 1997; Diwanay et al., 2004; Gautam et al., 2004). One human trial confirmed the herb’s potency in treating dyspepsia (Dalvi et al., 1990). A limited number of steroidal saponins have been reported previously from the roots of this plant, with the major one being shatavarins I and IV (Ravikumar et al., 1987; Joshi and Sukh, 1988; Jadhav and Bhutani, 2006), immunoside (Handa et al., 2003) and shatavarin V (Hayes et al., 2006b). Recently, the racemosides (Mandal et al., 2006) were described from the only study of the fruits of A. racemosus. Our preliminary work on the saponin content of A. rac- emosus roots revised the structures of the two major sapo- nins of this plant, shatavarins I, 10 and IV, 7 (Hayes et al., 2006a). We unambiguously demonstrated (based on exten- sive 1D and 2D NMR experiments) that the previous reports wrongly assigned the glycosidic linkages in both shatavarin I and IV. Further confirmation was provided by the isolation of a new minor steroidal saponin from the A. racemosus roots (Hayes et al., 2006b), shatavarin 0031-9422/$ - see front matter Ó 2007 Elsevier Ltd. All rights reserved. doi:10.1016/j.phytochem.2007.09.001 * Corresponding author. Tel.: +61 7 3365 3825; fax: +61 7 3365 4299. E-mail address: j.devoss@uq.edu.au (J.J. De Voss). www.elsevier.com/locate/phytochem Available online at www.sciencedirect.com Phytochemistry 69 (2008) 796–804 PHYTOCHEMISTRY