lignans and yatein

The two new lignans 3α-O-(β-D-glucopyranosyl)desoxypodophyllotoxin (1) and 4-O-(β-D-glucopyranosyl)dehydropodophyllotoxin (2) were isolated from Cleistanthus boivinianus, together with the known lignans deoxypicropodophyllotoxin (3), (±)-β-apopicropodophyllin (4), (-)-desoxypodophyllotoxin (5), (-)-yatein (6), and β-peltatin-5-O-β-D-glucopyranoside (7). The structures of all compounds were characterized by spectroscopic techniques. Compounds 1, 4, and 5 showed potent antiproliferative activities against the A2780 ovarian cancer cell line, with IC50 values of 33.0 ± 3.6, 63.1 ± 6.7, and 230 ± 1 nM, respectively. Compounds 2 and 7 showed only modest A2780 activities, with IC50 values of 2.1 ± 0.3 and 4.9 ± 0.1 μM, respectively, while compounds 3 and 6 had IC50 values of >10 μM. Compound 1 also had potent antiproliferative activity against the HCT-116 human colon carcinoma cell line, with an IC50 value of 20.5 nM, and compound 4 exhibited modest antiproliferative activity against the A2058 human caucasian metastatic melanoma and MES-SA human uterine sarcoma cell lines, with IC50 values of 4.6 and 4.0 μM, respectively.

Topics: 4-Butyrolactone; Antineoplastic Agents, Phytogenic; Cell Proliferation; Dioxoles; Drug Screening Assays, Antitumor; Forests; HCT116 Cells; Humans; Inhibitory Concentration 50; Lignans; Madagascar; Malpighiaceae; Molecular Structure; Nuclear Magnetic Resonance, Biomolecular; Plant Leaves; Plasmodium falciparum; Stereoisomerism

Little is known about the biosynthesis of yatein, in spite of its importance as a typical heartwood lignan and a key biosynthetic intermediate of the antitumor lignan podophyllotoxin. The present study, based on individual administration of [13C]phenylalanine and deuterium labelled lignans and simultaneous administration of two distinct lignans labelled with deuterium atoms to Anthriscus sylvestris, established the two independent branch pathways from matairesinol, one to afford yatein via thujaplicatin, 5-methylthujaplicatin, and 4,5-dimethylthujaplicatin and the other to bursehernin via pluviatolide. The latter pathway did not lead to yatein, eliminating the presence of a metabolic grid from matairesinol to yatein.

Topics: 4-Butyrolactone; Apiaceae; Benzyl Compounds; Carbon Isotopes; Deuterium; Dioxoles; Furans; Lactones; Lignans; Mass Spectrometry; Phenylalanine; Podophyllin

A new GC-MS method for monitoring lignans was developed to study the variation in plants and elucidate the biosynthetic steps. A simple and fast extraction procedure for lyophilised plant material was developed, giving a lignan-rich extract. A GC-MS method was set up using an apolar WCOT fused silica column using a high temperature programme (150 degrees C to 320 degrees C at 15 degrees C min(-1)). This new GC-MS method gave a clear lignan profile of plant material. It was possible to show the large variation in the concentrations of deoxypodophyllotoxin (DOP), yatein and anhydropodorhizol (AHP) in Anthriscus sylvestris (L.) Hoffm. plants growing on different locations using cinchonidin as an internal standard. In contrast with existing GC methods for lignan analysis no derivatisation is needed. It is also possible to use this method for the detection of different classes of lignans in biosynthetically related plant species.

Topics: 4-Butyrolactone; Apiaceae; Dioxoles; Drugs, Chinese Herbal; Gas Chromatography-Mass Spectrometry; Lignans; Plant Extracts; Podophyllotoxin