Cytotoxic Polyhydroxylated Oleanane Triterpenoids from Cissampelos pareira var. hirsuta

Abstract

Three new polyhydroxylated oleanane triterpenoids, cissatriterpenoid A−C (1−3), along with one known analogue (4), were isolated from the whole plant of Cissampelos pareira var. hirsuta. Their chemical structures were elucidated by extensive spectroscopic data (IR, HR-ESI-MS, 1H-NMR, 13C-NMR, DEPT, 1H-1H COSY, HSQC, HMBC, NOESY) and the microhydrolysis method. The isolation of compounds 1–4 represents the first report of polyhydroxylated oleanane triterpenoids from the family Menispermaceae. All isolated compounds were evaluated for their cytotoxicity against five human cancer cell lines, and the inhibitory activity against NO release in LPS-induced RAW 264.7 cells. Compound 3 showed the most potent cytotoxic activities against the A549, SMMC-7721, MCF-7, and SW480 cell lines, with IC50 values of 17.55, 34.74, 19.77, and 30.39 μM, respectively, whereas three remaining ones were found to be inactive. The preliminary structure–activity relationship analysis indicated that the γ-lactone ring at C-22 and C-29, and the olefinic bond at C-12 and C-13 were structurally required for the cytotoxicity of polyhydroxylated oleanane triterpenoids against these four cell lines. Based on lipid-water partition coefficients, compound 3 is less lipophilic than 1 and 4, which agrees with their cytotoxic activities. This confirms the potential of C. pareira var. hirsuta in the tumor treatment.

Lignans from the Roots and Rhizomes of Dysosma versipellis and Their Cytotoxic Activities

“…All isolated compounds were evaluated for their in vitro cytotoxic activities against the A-549 and SMMC-7721 cell lines using the MTS assay [ 22 ] with cisplatin and paclitaxel as positive controls, and the IC 50 values are summarized in Table 3 . Compounds 7 – 12 and 14 – 17 showed more potent cytotoxicities against the SMMC-7721 cell line than the A549 cell line.…”

“…By the previously reported MTS method [ 22 ], the cytotoxic activities of compounds 1 – 18 were evaluated against human lung cancer A-549, hepatocellular carcinoma SMMC-7721 cell lines. The cells were cultured in RPMI-1640 medium, supplemented with 10% fetal bovine serum (FBS) at 37 ℃ under 5% CO 2 in a humidified atmosphere.…”

Antimicrobial Activity of Lactones

“…Lactones are a group of compounds widely distributed in nature [ 1 , 2 , 3 , 4 ]. Chemically, they can be classified as intramolecular esters of hydroxycarboxylic acids with different ring sizes.…”