Anti-inflammatory and anticancer activities of (−)-zeylenol from stems of Uvaria grandiflora

Abstract

Uvaria grandiflora has stimulated rigorous phytochemical investigation aimed at determining chemical structures and biological activities. In recent years, many polyoxygenated cyclohexenes have been isolated from this genus. This study reports that zeylenol isolated from the stems of U. grandiflora possess potential anti-inflammatory, anticancer, and caspase-3 activities. The structure of this compound was elucidated from spectroscopic analysis, particularly 2D NMR techniques. The anti-inflammatory effect and toxicity of zeylenol were evaluated in animal models and compared to that of reference drugs. In addition, the cytotoxicity of the isolated compound against human breast cancer MDA-MB231 and hepatocellular carcinoma HepG2 cell lines were studied. The test (−)-zeylenol at the dose of 1 mg/ear significantly inhibited oedema formation by 90%, 69%, 52%, and 52% after 15, 30, 60, and 120 min, respectively. Zeylenol was found to be toxic to both MDA-MB231 and HepG2 cells in a dose response manner with IC50 values of 54 ± 10 and > 80 µM, respectively. The compound induced MDA-MB231 cell apoptosis via caspase-3 activation. Zeylenol probably possesses anti-inflammatory activity by inhibiting the synthesis or release of various inflammatory mediators and might be used to induce human breast cancer MDA-MB231 cell apoptosis.

Annonaceae: Breaking the Wall of Inflammation

“…Thus, this study provides some scientific evidence of the usage of these three species in traditional anti-cancer and anti-inflammatory regimens. Seangphakdee et al ( 2013 ) reported similar anti-inflammatory activity for poly-oxygenated cyclohexane zeylenol (35) (Figure 1 ) isolated from Uvaria grandiflora . Anti-inflammatory activity of zeylenol (35) was evaluated on rats using ear edema assay.…”

Antioxidant and antimicrobial alkaloids isolated from twigs of Uvaria grandiflora Roxb.

“…The antimicrobial activity against tested microbes including Staphylococcus aureus (ATCC29213), Escherichia coli (ATCC25922), and Candida albicans (ATCC 10231) at 10 µg/ml concentration revealed that all the compounds screened did not show inhibitory activity (for information detail; see Table S4). According to literature reports, the crude extracts and pure compounds isolated from various parts of U. grandiflora were examined for several biological activities such as cytotoxic, anti-inflammatory, antioxidant, and antimicrobial activities [6][7][8][9][20][21][22]. To the best our search from SciFinder database, compounds 1-6 have never been investigated for their antioxidant activity.…”

Anti-infective activities of 11 plants species used in traditional medicine in Malaysia

“…We were unable to characterize the other peaks because of impurity and then insufficient amount and further work need to be done with this plant. Zeylenol is a known constituent of U. grandiflora (Seangphakdee et al, 2013) whereas ferrudiol is reported for the first time from this plant. We tested zeylenol and ferrudiol for cytotoxicity against MRC-5, which were both non-toxic.…”