Cytotoxic Compounds from the Stems of Cinnamomum tenuifolium

Abstract

Three new butanolides, tenuifolide A (1), isotenuifolide A (2), and tenuifolide B (3), a new secobutanolide, secotenuifolide A (4), and one new sesquiterpenoid, tenuifolin (5), along with 16 known compounds were isolated from the stems of Cinnamomum tenuifolium. Their structures were determined by spectroscopic analyses. Compound 4 was found to induce apoptotic-related DNA damage, increase sub-G1 cells, and inhibit the growth of human prostate cancer cells, DU145. In addition, treatment with 4 significantly increased intracellular H2O2 and/or peroxide. The results show that 4 induced (a) noticeable reduction of mitochondrial transmembrane potential (DeltaPsim); (b) significant increase in the ratio of cytochrome c concentration (cytosol/mitochondria); and (c) subsequent activation of caspase-9/caspase-3. Antiproliferation caused by 4 was found to markedly decrease when pretreated with caspase-9/caspase-3 inhibitor. In ROS scavenging, antioxidant, NADPH oxidase, and NO inhibitor studies, pretreatment of DU145 cells with either DPI, dexamethasone, L-NAME, or mannitol decreased 4-induced intracellular DCF fluorescence of ROS. These results suggest that an increase of H2O2 and/or peroxide by 4 is the initial apoptotic event and 4 has anticancer effects on DU145 cells.

Madangones A and B: Two new neolignans from the stem bark of Beilschmiedia madang and their bioactivities

“…Thus, compound (2) was identified as 2,8-dihydroxy-3′,4′-methylenedioxy-5,6-cyclo-1,7-neolign-10-en-4-one, or (-)-madangone B (2). All known compounds, vanilin, vanillic acid, betulin (Lin et al, 2010), β-sitosterol (Huang et al, 2011) and β-sitostenone (Lin et al, 2009) , 1984;Whiting, 1987). The neolignans (1-3), isolated in this study, were tested for their antioxidant, acetylcholinesterase inhibitory and anti-inflammatory activities.…”

Tenuifolide B from Cinnamomum tenuifolium Stem Selectively Inhibits Proliferation of Oral Cancer Cells via Apoptosis, ROS Generation, Mitochondrial Depolarization, and DNA Damage

“…nervosum (Meissn.) Hara [22], an evergreen form of the Lauraceae plant family grown on Orchid Island of Taiwan. Methanol extracts were used to identify a new benzodioxocinone, benzodioxocinone (2,3-dihydro-6,6-dimethylbenzo-[b][1,5]dioxocin-4(6 H )-one), from the leaves of C. tenuifolium [23].…”

“…Alternatively, we previously used the stems of C. tenuifolium [22] to identify several novel compounds, including tenuifolide A, isotenuifolide A, tenuifolide B (TFB), secotenuifolide A, and tenuifolin, along with some known compounds. Secotenuifolide A was found to provide the best antiproliferative effect against two human prostate cancer cells (DU145 and LNCaP) with IC 50 values < 7 μM after 24 h of treatment.…”

Isolation of new esters from the stems ofCinnamomum reticulatumHay

“…Chen, Lo, & C.Y. Chen, 2006;Kuo, Chen, & Hsu, 2007;Kuo, Chen, Tzeng, Lin, & Hsu, 2008aLin, Lo, Wang, & Chen, 2008;Lin et al, 2009;Liu et al, 2008), two n-hexane and CHCl 3 extractions of the stems of C. reticulatum afforded a mixture of 4-hydroxy-3-methoxyphenethyl derivatives (1-5), along with nine known compounds including two butanolides, isoobtusilactone A (6) (Anderson, Ma, Smith, Chang, & Mclaughlin, 1992) and obtusilactone A (7) (Anderson et al, 1992), two amides, N-trans-feruloylmethoxytyramine (8) (Chen, Chang, Yen, & Wu, 1998a) and N-cis-feruloylmethoxytyramine (9) (Chen et al, 1998a), three benzenoids, p-hydroxybenzoic acid (10) (Chen, Chang, Teng, & Wu, 1999), syringic acid (11) (Chen et al, 1999) and vanillic acid (12) (Chen et al, 1999), one lignan, (þ)-syringaresinol (13) (Chen, Wu, Chang, & Wu, 1998b) and one steroid, -sitostenone (14) (Chen, Chang, & Wu, 1997). Among them, 3-5 are new compounds, and 1, 2, 6-11, 13 and 14 were isolated for the first time from this species (Kuo & Shue, 1991).…”