Dimericbiscognienyne A (1), an unusual diisoprenyl-cyclohexene-type meroterpenoid dimer, was isolated from Biscogniauxia sp. together with three new monomeric diisoprenyl-cyclohexene-type meroterpenoids (2-4) and one new isoprenyl-benzoic acid-type meroterpenoid (5). All structures were determined by extensive NMR spectroscopic methods, quantum chemical calculations, chemical derivatization, and X-ray crystallography. The formation of 1 is related to a unique intermolecular redox coupling Diels-Alder adduct reaction. Their cytotoxicities and short-term memory enhancement activities against Alzheimer's disease were assessed.

Recent studies suggest that the nanorods consisting of europium hydroxide could promote angiogenesis. In this study, we sought to determine if additional types of nanoparticles were capable of enhancing angiogenesis and in addition, understand the underlying mechanisms. For this reason, we employed a method that combines a high throughput in vitro cell based screen coupled with an in vivo validation using vascular specific green fluorescent protein (GFP) reporter transgenic zebrafish for examining proangiogenesis activity. After screening multiple types of nanoparticles, we discovered that four of them: EuIII(OH)3 rods (Eu Rods), EuIII(OH)3 spheres (Eu Spheres), TbIII(OH)3 rods (Tb Rods) and TbIII(OH)3 spheres (Tb Spheres), were the most effective in promoting angiogenesis. We also showed that ionic forms of europium nitrate [Eu(NO3)3] (Eu) and terbium nitrate [Tb(NO3)3] (Tb), the two lanthanide elements for these four nanoparticles, were also capable of enhancing angiogenesis. However, this effect was further enhanced by nanoparticle synthesis. Finally, we demonstrated that reactive oxygen species H2O2 is a key factor in the process of proangiogenesis by lanthanide elemental nanoparticles.

The alkyne is a biologically significant moiety found in many natural products and a versatile functional group widely used in modern chemistry. Recent studies have revealed the biosynthesis of acetylenic bonds in fatty acids and amino acids. However, the molecular basis for the alkynyl moiety in acetylenic prenyl chains occurring in a number of meroterpenoids remains obscure. Here, we identify the biosynthetic gene cluster and characterize the biosynthetic pathway of an acetylenic meroterpenoid biscognienyne B based on heterologous expression, feeding experiments, and in vitro assay. This work shows that the alkyne moiety is constructed by an unprecedented cytochrome P450 enzyme BisI, which shows promiscuous activity towards C5 and C15 prenyl chains. This finding provides an opportunity for discovery of new compounds, featuring acetylenic prenyl chains, through genome mining, and it also expands the enzyme inventory for de novo biosynthesis of alkynes.

Two pairs of enantiomeric phthalide trimers [(-)/(+) triligustilides A (1a/1b) and (-)/(+) triligustilides B (2a/2b)] with complex polycyclic skeletons simultaneously possessing bridged, fused, and spiro ring systems were isolated from Angelica sinensis, together with two pairs of new phthalide dimers. The biogenetic pathways of new phthalides were proposed, and their bioactivities were also evaluated. This is the first time optically pure polymeric phthalides have been obtained from racemates, and their absolute configurations are reported.