akuammicine and vincadifformine

Vinca minor is a herbaceous plant from the Apocynaceae family known to produce over 50 monoterpene indole alkaloids (MIAs). These include several biologically active MIAs that have a range of pharmaceutical activities. The present study shows that the MIAs, vincamine, akuammicine, minovincinine, lochnericine and vincadifformine tend to be secreted on V. minor leaf surfaces. A secretion mechanism of MIAs, previously described for Catharanthus roseus, appears to be mediated by a member (CrTPT2) of the pleiotropic drug resistance ABC transporter subfamily. The molecular cloning of an MIA transporter (VmTPT2/VmABCG1) that is predominantly expressed in V. minor leaves was functionally characterized in yeast and established it as an MIA efflux transporter. The similar function of VmTPT2/VmABCG1 to CrTPT2 increases the likelihood that this MIA transporter family may have co-evolved within members of Apocynaceae family to secrete selected MIAs and to regulate leaf MIA surface chemistry.

Topics: Alkaloids; ATP-Binding Cassette Transporters; Cloning, Molecular; Indole Alkaloids; Indoles; Plant Leaves; Plant Proteins; Secologanin Tryptamine Alkaloids; Vinca; Vincamine

Organic chemists are now able to synthesize small quantities of almost any known natural product, given sufficient time, resources and effort. However, translation of the academic successes in total synthesis to the large-scale construction of complex natural products and the development of large collections of biologically relevant molecules present significant challenges to synthetic chemists. Here we show that the application of two nature-inspired techniques, namely organocascade catalysis and collective natural product synthesis, can facilitate the preparation of useful quantities of a range of structurally diverse natural products from a common molecular scaffold. The power of this concept has been demonstrated through the expedient, asymmetric total syntheses of six well-known alkaloid natural products: strychnine, aspidospermidine, vincadifformine, akuammicine, kopsanone and kopsinine.

Topics: Alkaloids; Biological Products; Biomimetics; Catalysis; Chemistry, Organic; Cyclization; Indole Alkaloids; Indoles; Quinolines; Research Design; Strychnine