New Terpenoids from Pfaffia paniculata Kuntze

Pfaffia (Amaranthaceae) has around ninety species in Central and South American, of which Pfaffia paniculata Kuntze (commonly called suma), is the most employed species in commercial preparations in Brazil as “Brazilian ginseng” and has been commonly used for three centuries for the same indications as American and Asian ginseng [1,2]. It is also known as “Para Toda” which means “for all things” since the root of this plant has been used by native Brazilians as a tonic, aphrodisiac, and as a remedy for many types of illnesses, such as diabetes, ulcers, cancer etc [3]. Phytosterols (mainly β-ecdysone), pfaffic acid (hexacyclic nortriterpene) and their glycosides, named pfaffosides A–F (saponins), have been reported from P. paniculata [4–7]. The saponins have demonstrated the ability to inhibit the growth of cultured tumor cell melanomas in vitro [6,7]. These saponins and pfaffic acid derivatives were patented as antitumor compounds in several Japanese patents in the mid-1980s [9,10]. In the present study, a detailed phytochemical investigation of P. paniculata was carried out. Two new nortriterpenoids pfaffine A and B, one monoterpene glycoside pfaffine C, along with the known compounds, ecdysone, 20-hydroxyecdysone, pterosterone, rapisterone, pfaffic acid, pfameric acid, mesembryanthemoidigenic acid, Calenduloside E 6ʹ-methyl ester, oleanolic acid 28-O-β-D-glucopyranoside were isolated from the roots of this plant. Their structures were determined through the extensive analysis of 1D- (1H, 13C, DEPT) and 2D-NMR (COSY, HSQC, HMBC, NOESY) spectra, as well as chemical methods. Acknowledgement: This work is funded in part by the Food Drug Administration contract “Biotanical Dietary Supplement: Science-Base for Authentication” FD-U-002071-07. Authors are thankful to Dr. Vaishali Joshi for the authentication of plant material. References: [1] Vasconcelos JMO (1982), Estudo taxonomico sobre Amaranthaceae no RS, Brasil. Porto Alegre, 151 p. [2] Taniguchi SF, et al. (1997), Phytother. Res., 11: 568–571. [3] Oliveira F, (1986), Revista Brasileira de Farmacognosia, 1: 86–92. [4] Wakunaga Pharmaceutical Co., Ltd., Japan (1984), Jpn. Kokai Tokkyo Koho., 5 pp. [5] Takemoto T, et al. (1983), Tetrahedron Letters, 24, 1057–60. [6] Nishimoto N, et al. (1984), Phytochemistry, 23: 139–42. [7] Nakai S, et al. (1984), Phytochemistry 23: 1703–1705. [8] Oshima M, Gu Y, (2003), Journal of Reproduction and Development, 49: 175–180. [9] Takemoto T, Odajima T, (1984), Jpn. Kokai Tokkyo Koho., 7 pp. [10] Takemoto T, Odajima T, (1984), Jpn. Kokai Tokkyo Koho., 11 pp.