Gindarudine, a novel morphine alkaloid from Stephania glabra Deepak Kumar Semwal * , Usha Rawat Department of Chemistry, H.N.B. Garhwal University Srinagar, Uttarakhand 246174, India Received 24 November 2008 Abstract A novel morphine alkaloid, named gindarudine 1 has been isolated from ethanol extract of Stephania glabra tubers, together with four known alkaloids, palmatine, dehydrocorydalmine, stepharanine, and 8-(4 0 -methoxybenzyl)-xylopinine. Compound 1 was elucidated as 3,6-O,N-detrimethyl-10-hydroxy-1-methoxy-thebaine by means of spectroscopic data including 2D NMR studies. # 2009 Deepak Kumar Semwal. Published by Elsevier B.V. on behalf of Chinese Chemical Society. All rights reserved. Keywords: Stephania glabra; Menispermaceae; Gindaru; Gindarudine Stephania glabra vern. gindaru, belonging to family Menispermaceae is a large, climbing shrub, indigenous to lower Himalaya of India. The tubers of the plant used for the treatment of variety of disorders, including asthma, tuberculosis, dysentery and fever. It is used as psycomedicine by natives in India [1,2]. More than thirty alkaloids of different classes have been isolated from the plant [3–6]. This paper reports the isolation and characterization of a novel morphine alkaloid, gindarudine (1) from the tubers. Gindarudine (1)(Fig. 1), brown crystalline solid, mp 178–180 8C, ½a 20 D 0, deduced the molecular formula C 17 H 17 NO 5 from the molecular ion peak at m/z 315.1107 in its HREIMS. It was recognized as morphine alkaloid by characteristic orange-red color with dilute nitric acid, UV absorption maxima at l MeOH max 276, 233 nm and IR bands at y KBr max 3516 (OH) and 1454 (NH) cm 1 [7]. 1 H, 13 C NMR, COSY, HMBC and NOESY data are summarized in Table 1. The 1 H NMR spectrum exhibited the signals for three aromatic protons (d 6.65, 6.83 and 6.90 all singlets), a methoxyl (d 3.83 s), two aromatic hydroxyls (d 11.23, OH-3 and d 9.56, OH-6), an aliphatic hydroxyl (d 4.26, OH-10) and a cyclic NH (d 4.26). The 13 C NMR and DEPT spectra showed seventeen signals including one methoxyl carbon (d 56.68). These data were somewhat similar to known compound thebaine [8] except the presence of hydroxyl groups and absence of N-methyl group. The HMBC experiments (Fig. 2) showed correlation of OH-3 (d 11.23) to C-2 (d 116.5) / C-4 (d 143.3), OH-6 (9.56) to C-5 (d 59.7) / C-7 (d 112.0) and OH-10 (d 4.26) to C-9 (d 50.5), suggesting that these hydroxyl groups should be located to C-3, C-6 and C-10, respectively. The NOESY experiments showed strong correlation of OMe-1 (d 3.83) to H-2 (d 6.65) and H-10 (d 4.42), suggested that methoxyl group located at C-1, which was further supported by the HMBC correlation of OMe-1 to C-1 (d 145.4). On the basis of these findings and the most abundant ion at m/z 234 (100%) in MS (Fig. 3), the structure of 1 was established as 3,6-O, N-detrimethyl 10-hydroxy 1-methoxythebaine. www.elsevier.com/locate/cclet Available online at www.sciencedirect.com Chinese Chemical Letters 20 (2009) 823–826 * Corresponding author. E-mail address: dr_dks.1983@yahoo.co.in (D. Kumar Semwal). 1001-8417/$ – see front matter # 2009 Deepak Kumar Semwal. Published by Elsevier B.V. on behalf of Chinese Chemical Society. All rights reserved. doi:10.1016/j.cclet.2009.03.002