Isolation and characterization of bioactive compounds from the bark of Litsea costalis.

The bark of Litsea costalis affords two new compounds named 4,4'-diallyl-5,5'-dimethoxy-[1,1'-biphennyl]-2,2'-diol, biseugenol A (1) and 2,2'-oxybis (4-allyl-1-methoxybenzene), biseugenol B (2) along with two known compounds (3-4), namely 5-methoxy-2-Hydroxy Benzaldehyde (3), and (E)-4-styrylphenol (4). The structures of 1 and 2 were determined using 1D and 2D NMR data. Also, the IR and NMR data were combined with quantum chemical calculations in the DFT approach using the hybrid B3LYP exchange-correlation function to confirm the structures of the compounds. Compounds showed fairly potent anticancer activity against cell lines and antioxidant (DPPH).

Flavonoids and linderone from Lindera oxyphylla and their bioactivities.

A new linderone A, namely 2-cinnamoyl-3-hydroxy-4, 5-dimethoxycyclopenta-2, 4-dienone (5), together with three known flavonoids (1-3) and one linderone (4), were isolated from the bark of Lindera oxyphylla. Extensive spectroscopic analysis including 1D and 2D-NMR spectra determined their sturctures. In addition, the antioxidant activity of all the compounds has been determined using 2, 2-diphenyl-1-picrylhydrazyl radical scavenging (DPPH), ferric reducing antioxidant power (FRAP) and ferrous ion chelating (FIC) methods. Compound 3 showed excellent DPPH scavenging activity with IC50% value of 8.5 ± 0.004% (µg/mL) which is comparable with vitamin C. This compound, also showed an absorbance value of 1.00 ± 0.06% through FRAP test when compared with Butyl Hydroxy Aniline (BHA). However, FIC showed low activity for all the isolated compounds (chelating activity less than 50%) in comparison with ethylene diamine tetra acetic acid (EDTA). Anticancer activity for all compounds has also been measured on A375 human melanoma, HT-29 colon adenocarcinoma, MCF-7 human breast adenocarcinoma cells, WRL-68 normal hepatic cells, A549 non-small cell lung cancer cells and PC-3 prostate adenocarcinoma cell line. Compound 1 showed A549=65.03%, PC-3=30.12%, MCF-7=47.67, compound 2 showed PC-3=90.13%, compound 3 showed MCF-7=79.57 and for compound 5 MCF-7 is 96.33.

A triclinic polymorph of (E)-2-(1-hy-droxy-3-phenyl-prop-2-en-1-yl-idene)-4,5-dimeth-oxy-cyclo-pent-4-ene-1,3-dione.

The title compound, C(16)H(14)O(5), is a triclinic polymorph of a previously reported monoclinic structure [Hosseinzadeh et al. (2011 ▶). Acta Cryst. E67, o1544]. The mol-ecule is roughly planar, the r.m.s. deviation from the least-squares plane of all non-H atoms being 0.092 Å. In the crystal, adjacent mol-ecules are linked through C-H⋯O hydrogen bonds into an infinite two-dimensional network parallel to (011). The layers are further connected via C-H⋯π inter-actions, forming a three-dimensional structure. Intra-molecular O-H⋯O and C-H⋯O hydrogen bonds are also observed.

Whole-mol-ecule disordered (E)-2-(1-hy-droxy-3-phenylprop-2-en-1-yl-idene)-4,5-dimeth-oxycyclo-pent-4-ene-1,3-dione isolated from Lindera oxyphylla (Lauraceae).

In the mol-ecule of the title compound, C(16)H(14)O(5), all non-H atoms are approximately co-planar [maximum atomic deviation = 0.064 (5) Å]. The hy-droxy group is a hydrogen-bond donor to a carbonyl O atom. Weak intermolecular C-H⋯O hydrogen bonding is present in the crystal structure. The crystal structure is 'whole-mol-ecule disordered' about an axis that runs approximately along the length of the mol-ecule; the occupancy of the two disorder components was set as exactly 0.5. An intra-molecular O--H⋯O hydrogen bond exists in each component.