rutundic-acid and Neoplasms

To study the chemical constituents and bioactivity of the stem bark of Mitragyna diversifolia.. Compounds were isolated by various chromatographic methods. Their structures were elucidated on the basis of spectroscopic techniques (IR, UV, MS, and NMR), and they were evaluated for their cytotoxic activities by the MTT method.. Eight triterpenes were isolated and identified as 3α, 6β, 19α-trihydroxy-urs-12-en-28-oic acid (1), 3β, 6β, 19α-trihydroxy-urs-12-en-28-oic acid (2), 3-oxo-6β-19α-dihydroxy-urs-12-en-28-oic acid (3), 3β, 6β, 19α-trihydroxy-urs-12-en-24, 28-dioic acid 24-methyl ester (4), 3β, 6β, 19α, 24-tetrahydroxy-urs-12-en-28-oic acid (5), rotundic acid (6), 23-nor-24-exomethylene- 3β, 6β, 19α-trihydroxy-urs-12-en-28-oic acid (7), and pololic acid (8), respectively. All of the isolates were tested against two human tumor cell lines, MCF-7 (breast) and HT-29 (colon).. Compound 1 was a new triterpene. Compounds 5 - 7 exhibited potent inhibitory effects on the growth of MCF-7 and HT-29 cells, and the others showed no cytotoxicity.

Topics: Antineoplastic Agents, Phytogenic; HT29 Cells; Humans; MCF-7 Cells; Mitragyna; Molecular Structure; Neoplasms; Phytotherapy; Plant Bark; Plant Extracts; Plant Stems; Triterpenes

Six novel rotundic acid (RA, 1) derivatives 4a-4f modified at the 28-COOH position were synthesized, and their structures were confirmed by IR, MS, 1H NMR and 13C NMR. The derivatives were evaluated for cytotoxic properties on the following three tumor cell lines: HeLa, HepG2 and SGC-7901. Compound 4f showed better cytotoxic activity compared with RA treatment and lower IC50 (4.16 µM) on HepG2 cells than on HeLa (8.54 µM) and SGC-7901 cells (11.32 µM). The anticancer mechanism of compound 4f was studied through cell cycle progression and apoptosis. Notably, compound 4f was able to induce apoptosis and G0/G1 cell cycle arrest of HepG2 at a concentration of 4.16 µM. In summary, RA was modified to obtain six novel derivatives. Compound 4f exhibited better cytotoxicity and may be developed as a potential agent against hepatocellular carcinoma.

Topics: Antineoplastic Agents; Apoptosis; Cell Line, Tumor; Drug Screening Assays, Antitumor; G1 Phase Cell Cycle Checkpoints; HeLa Cells; Hep G2 Cells; Humans; Neoplasms; Triterpenes