New Steroidal Erythrityl Triesters from the Heat Processed Roots of Panax ginseng

Two new compounds stigmasta-3α-ol-3α-(2′R,3′S)-butane-1′,2′,3′,4′-tetraolyl-2′,3′-dioctadec-9″/9？-enoyl-4′-octadec-9″″,12″″-dienoate (1) and stigmasta-5-en-3β-ol-3β-(2′R,3′S)-butane-1′,2′,3′,4′-tetraolyl-2′,3′-dioctadec-9″/9？-enoyl-4′-octadec-9″″,12″″-dienoate (2) along with β-sitosterol-β-D-glucoside were isolated and identified from the heat processed roots of Panax ginseng. The structures of the new compounds were elucidated by 1D and 2D NMR (COSY, HSQC, and HMBC) spectroscopic techniques aided by FAB-MS, ESI FT/MS, and IR spectra. 1. Introduction Ginseng (Panax ginseng C. A. Meyer, Araliaceae) is one of the most important oriental medicinal plants in Japan, Korea and China [1]. Of the two kinds of ginseng, white ginseng is air dried, and red ginseng is produced by steaming raw ginseng at 98–100°C for 2-3？h. It has been reported that red ginseng is more effective in pharmacological activities than white ginseng [2–5]. The differences in biological activities and chemical constituents of red and white ginsengs have been reported. Anticancer properties and other pharmacological activities of Panax ginseng [6–8] have been studied and ginsenosides are recognized as active anticancer compounds [6]. Compared with Asian white ginseng, red ginseng has stronger anticancer activities [9, 10]. Recently, there was a report using a steaming process to treat American ginseng root [5]. In the study, however, the treatment temperature was 100°C and, thus, chemical constituents did not change significantly. Anticarcinogenic and antidiabetic effects of P. ginseng have been reported [9, 11]. Several other compounds and biological activities have been reported from the ginseng roots of P. ginseng [12–14]. The most well-known chemical constituent of ginseng is ginsenosides, which are dammarane glycosides. Dammarane glycosides were reported from many parts of ginseng and heat processed P. ginseng roots [15, 16]. The chemical and morphological variations of Panax notoginseng and their relationship were recently described [17]. In continuation of our previous work [18, 19] on P. ginseng roots, two more new compounds were isolated as natural products. This paper deals with the isolation and structure elucidation of two new compounds, stigmasta-3α-ol-3α-(2′R,3′S)-butane-1′,2′,3′,4′-tetraolyl-2′,3′-dioctadec-9′′/9′′′-enoyl-4′-octadec-9′′′′,12′′′′-dienoate (1) and stigmasta-5-en-3β ol-3β-(2′R,3′S)-butane-1′,2′,3′,4′-tetraolyl-2′,3′-dioctadec-9′′/9′′′-enoyl-4′-octadec-9′′′′,12′′′′-dienoate (2), on the basis of 1H and 13C NMR, spectroscopic studies, including 2D-NMR (COSY, HMBC,