New Triterpenoids fromKadsura heteroclitaand their Cytotoxic Activity

Abstract

Phytochemical investigations of the stem of Kadsura heteroclita (Roxb) Craib (Schizandraceae) resulted in the isolation and structure elucidation of six new triterpenoidal compounds named heteroclitalactones A-E (1-5) as well as heteroclic acid (6) and heteroclitalactone F (7), which was isolated for the first time from a natural source, and the six known compounds schisanlactone E (8), cycloartenone (9), schisandronic acid (10), nigranoic acid (11), changnanic acid (12) and schisanlactone B (13), respectively. The structures of these compounds were characterized by extensive 1D and 2D NMR spectral analyses. The majority of these triterpenoids showed moderate cytotoxic activity against the human tumor cell lines Bel-7402, BGC-823, MCF-7 and HL-60. Among the compounds tested, heteroclitalactone D (4) showed the strongest cytotoxic activity against the HL-60 cells with an IC50 of 6.76 microM.

Structural determination of seven new triterpenoids from Kadsura heteroclita by NMR techniques

“…11 Furthermore, the UV spectrum ( max log ε D 208 (4.26), 242 (4.24), 330 (4.08) nm) and HMBC experiment confirmed that four double bonds are conjugated to form an A, B-seco-9, 19-cyclolanostene skeleton. 10 The acetoxyl group (υ C 169.87, 21.30; υ H 2.06, s) was located at C-12 since H-12 was correlated with C-18, C-11, C-13, C-14, C-9 and the carbonyl carbon of the acetoxyl group as shown in Fig. 2.…”

“…The 13 C NMR ( ,ˇ-unsaturated lactone was assigned as ring A on the basis of the results of HMBC and 1 H-1 H COSY analysis. 10 A six-membered ,ˇ-unsaturated lactone was demonstrated by the presence of a mass spectroscopic fragment at m/z 111 and the results of 1 H-1 H COSY and HMBC spectroscopic data. 11 Furthermore, the UV spectrum ( max log ε D 208 (4.26), 242 (4.24), 330 (4.08) nm) and HMBC experiment confirmed that four double bonds are conjugated to form an A, B-seco-9, 19-cyclolanostene skeleton.…”

“…1 The presence of triterpenoids, lignans and sesquiterpenes has been reported in this genus. 2 -9 Our previous phytochemical study on the stem of K. heteroclita resulted in the isolation of 13 triterpenoids including heteroclitalactones A-F. 10 As a continuation of our investigation on the stem of the title plant, we describe here the isolation and structure elucidation of seven new triterpenoids, named heteroclitalactones G-M (1-7). Their structures (Fig.…”

Cytotoxic and potential anticancer constituents from the stems ofSchisandra pubescens

“…Previously, tigloylgomisin P (2) had been reported to possess cytotoxicity against the Nicotiana BY-2 cell line (Smejkal et al, 2010) and schisanlactone B (8) was found to inhibit human cancer cell lines Bel-7402 and HL-60 (Wang et al, 2006). No prior literature had addressed the cytotoxicities of cagayanone (3), (À)-gomisin L 2 (4), micranoic acid B (5) and lancifodilactone H (6).…”

Bioactive metabolites of Schisanlactone E transformed by Cunninghamella blakesleana AS 3.970

“…Triterpenes with unique lanostane skeletons are the major constituents of the plants of genus Kadsura. Biological investigations indicated that these triterpenes had moderate cytotoxic effects against several cancer cell lines including Bel-7402, BGC-823, MCF-7, HL-60 and P388, as well as inhibitory effects against HBV, HBeAg and HIV [6]. Schisanlactone E (SE) is a typical triterpene obtained from genus Kadsura.…”