Ergoline alkaloids occur in taxonomically unrelated taxa, such as fungi, belonging to the phylum Ascomycetes and higher plants of the family Convolvulaceae. The disjointed occurrence can be explained by the observation that plant-associated epibiotic clavicipitalean fungi capable of synthesizing ergoline alkaloids colonize the adaxial leaf surface of certain Convolvulaceae plant species. The fu...

Two new Amaryllidaceae alkaloids, named lycoranines A (1) and B (2), were isolated from the bulbs of Lycoris radiata. Their structures were elucidated on the basis of extensive spectroscopic analysis. Compound 2 was a new-type alkaloid, which provided a new insight into the biosynthesis of alkaloids in Amaryllidaceae plants.

Carbon monoxide (CO) acts as an important signal in many physiological responses in plants, but its role in plant secondary metabolism is still unknown. Nicotine is the main alkaloid generated in tobacco and the plant hormone jasmonic acid (JA) has previously been reported to efficiently induce its biosynthesis. Whether and how CO interacts with JA to regulate nicotine biosynthesis in tobacco r...

Aj_EasH is a non-heme iron- and α-keto-glutarate-dependent oxidase that is responsible for an unusual cyclopropyl ring formation in the biosynthesis of the fungal ergot alkaloid cycloclavine. The three dimensional structure of Aj_EasH (2.2 Å resolution) reported here provides insight into the mechanism of this unusual and complex reaction.

The straightforward enantioselective construction of the hydroquinoline ring system from 1,5-polycarbonyl derivatives, using (R)-phenyglycinol as a chiral latent form of ammonia, is reported. The process mimics the key steps believed to occur in nature in the biosynthesis of amphibian decahydroquinoline alkaloids. Diastereodivergent routes to enantiopure cis-2,5-disubstituted decahydroquinoline...

Oripavine is the major alkaloid of Papaver orientale. It is an important intermediate in the biosynthesis of morphine alkaloids. Recently, new Papaver somniferum strains have been developed which accumulate thebaine and oripavine, but not morphine and codeine. Therefore, the chemistry of oripavine has been studied intensively to synthesize opioid pharmaceuticals such as oxymorphone, naloxone an...

Several cDNAs of enzymes catalyzing biosynthetic pathways of plant-derived alkaloids have recently been heterologously expressed, and the production of appropriate enzymes from ajmaline and tropane alkaloid biosynthesis in bacteria allows their crystallization. This review describes the architecture of these enzymes with and without their ligands.

Citation Liscombe, David K., Aimee R. Usera, and Sarah E. O’Connor. “Homolog of Tocopherol C Methyltransferases Catalyzes N Methylation in Anticancer Alkaloid Biosynthesis.” Proceedings of the National Academy of Sciences 107.44 (2010) : 18793 18798. Copyright ©2010 by the National Academy of Sciences As Published http://dx.doi.org/10.1073/pnas.1009003107 Publisher National Academy of Sciences ...

The first total synthesis of Aplidiopsamine A, a rare 3H-pyrrolo[2,3-c]quinoline alkaloid from the Aplidiopsis confluata, has been achieved following the proposed biosynthesis. This biomimetic synthesis requires only five steps and proceeds in 20.8% overall yield. Biological evaluation across large panels of discrete molecular targets identified that Aplidiopsamine A is a highly selective PDE4 ...

Lupinus, Baptisia, Sarothamnus, Diumal Rhythm, Photomixotrophic Cell Suspension Cultures, Quinolizidine Alkaloids Fluctuations of quinolizidine alkaloid content in leaflets of Lupinus polyphyllus, L. hartwegii, Baptisia australis, and Sarothamnus scoparius were studied over a 36 h period. The alkaloid contents reached their maximum at noon or early afternoon, and their minimum during the night....