Hydrophilic and Cell-Penetrable Pyrrolidinyl Peptide Nucleic Acid via Post-synthetic Modification with Hydrophilic Side Chains.

Peptide nucleic acid (PNA) is a nucleic acid mimic in which the deoxyribose-phosphate was replaced by a peptide-like backbone. The absence of negative charge in the PNA backbone leads to several unique behaviors including a stronger binding and salt independency of the PNA-DNA duplex stability. However, PNA possesses poor aqueous solubility and cannot directly penetrate cell membranes.

Cytotoxic and anti-angiogenic properties of minor 3,4-seco-cycloartanes from Gardenia sootepensis exudate.

Gardenia plants have long been used as traditional medicines in various countries including Thailand. In this study, two new 3,4-seco-cycloartane triterpenes, sootependial (1) and sootepenoic acid (2), were isolated from bud exudate of G. sootepensis, together with five known compounds.

Antiangiogenic activity of 3,4-seco-cycloartane triterpenes from Thai Gardenia spp. and their semi-synthetic analogs.

Twelve naturally occurring 3,4-seco-cycloartane triterpenes (1-12) isolated from Gardenia sootepensis and Gardenia obtusifolia, and eight semi-synthetic derivatives (13-20) were evaluated for their antiangiogenic activity on a rat aortic sprouting assay, an ex vivo model of angiogenesis. Among these compounds, sootepin B (1) displayed the most potent activity in terms of the inhibition of microvessel sprouting from rat aortic rings in a dose-dependent manner with IC(50) value of 4.46 μM.

Gardenoins E-H, cycloartane triterpenes from the apical buds of Gardenia obtusifolia.

Four new cycloartane triterpenes, named gardenoins E-H (1-4), were isolated from the apical buds of Gardenia obtusifolia, together with five known cycloartanes. Only compound 1 displayed cytotoxicity against colon, hepatic and lung cancer cell lines.

Xylorumphiins A-D, mexicanolide limonoids from the seed kernels of Xylocarpus rumphii.

Four new mexicanolide limonoids, named xylorumphiins A-D (1-4), were isolated from the seed kernels of Xylocarpus rumphii, together with three known limonoids. Their structures and configurations were established on the basis of spectroscopic data.

Cytotoxic 3,4-seco-cycloartane triterpenes from the exudate of Gardenia tubifera.

Four new 3,4-seco-cycloartanes, gardenoins A-D (1-4), together with the known compound secaubryenol (5), were isolated from the exudate of Gardenia tubifera. The structures of 1-4 were elucidated on the basis of spectroscopic analysis. The cytotoxic activity of compounds 1-4 was evaluated against five human tumor cell lines.

Cytotoxic 3,4-seco-cycloartane triterpenes from Gardenia sootepensis.

Five new 3,4-seco-cycloartanes, sootepins A-E (1-5), along with four known triterpenes (6-9), were isolated from the apical buds of Gardenia sootepensis. Their structures were elucidated on the basis of spectroscopic methods (1D and 2D NMR, HRESIMS, and X-ray crystallography), and the compounds were tested for in vitro cytotoxic activity against human breast (BT474), lung (CHAGO), liver (Hep-G2), gastric (KATO-3), and colon (SW-620) cancer cell lines. Generally, the compounds possessing an exomethylene gamma-lactone ring showed broad cytotoxicity for all cell lines tested.