Two new tropane alkaloid N-oxides substituted by a methylpyrrole moiety were isolated from the bark of Erythroxylum vacciniifolium Mart. (Erythroxylaceae), a Brazilian indigenous plant, locally known as catuaba and used in traditional medicine as an aphrodisiac. The alkaloid structures were determined by a combination of high resolution mass spectrometry and multi-dimensional NMR spectroscopy.

Recent advances in the cell, developmental, and molecular biology of alkaloid biosynthesis have heightened our appreciation for the complexity and importance of plant secondary pathways. Several biosynthetic genes involved in the formation of tropane, benzylisoquinoline, and terpenoid indole alkaloids have now been isolated. The early events of signal perception, the pathways of signal transduc...

Thirty-four alkaloids were identified in the organs of Hyoscyamus albus L. by gas-liquid chromatography-mass spectrometry (GLC-MS). Eight new compounds for the roots, eleven for the stems, twelve for the leaves, nineteen for the flowers, and seven for the seeds were detected. The alkaloids 5-(2-oxopropyl)-hygrine (8) and phygrine (20) are new for this species and 3-(hydroxyacetoxy)tropane (9), ...

The medicinally applied tropane alkaloids hyoscyamine and scopolamine are produced in Atropa belladonna L. and in a small number of other Solanaceae. Calystegines are nortropane alkaloids that derive from a branching point in the tropane alkaloid biosynthetic pathway. In A. belladonna root cultures, calystegine molar concentration is 2-fold higher than that of hyoscyamine and scopolamine. In th...

A stereoselective synthesis of (+)-physoperuvine, a tropane alkaloid from Physalis peruviana Linne has been developed using a one-pot tandem aza-Claisen rearrangement and ring closing metathesis reaction to form the key amino-substituted cycloheptene ring.

This review describes certain reminiscences about an area of chemical pharmacology I have been involved with, on and off, for many years. Specifically it focuses on tropane, a fascinating, naturally occurring bicyclic chemical ring system that lends itself to many pharmaceutical and therapeutic applications. My involvement with the tropane ring has started more than 60 years ago in 1949, when, ...

The purpose of the present study was to determine the tropane alkaloid content of four Hyoscyamus species from Iran, i.e. H. pusillus L., H. niger L., H. reticulatus L. and H. kurdicus Bornm. Determination of alkaloids was performed by the HPLC method. Samples were extracted with chloroform-methanol-25% ammonium hydroxide 15:5:1 (V/V/V). HPLC separation was performed on Eurospher C18 reversed p...

agrobacterium rhizogenes causes hairy root disease in plants. these hairy roots are ge-netically stable and grow rapidly. transformed hairy roots of hyoscyamus muticus in-duced by the bacterium can produce tropane alkaloids in trace amounts of intact plant tissues. in this research, in order to compare growth and biosynthetic stability of hairy roots with wild type ones, leaf and nodal segments...

agrobacterium rhizogenes (pri), a causative agent of hairy root disease, effectively induces hairy root formation in a variety of plant species. in our study four bacterial strains ar15834, a4, 9435 and c318 and three explants types leaf, stems and roots, were examined. hairy roots were induced from roots, stems and leaf explants. the highest transformation efficiency of 77% was achieved by usi...

The esterification of methylecgonine (2-carbomethoxy-3β-tropine) with benzoic acid is the final step in the biosynthetic pathway leading to the production of cocaine in Erythoxylum coca. Here we report the identification of a member of the BAHD family of plant acyltransferases as cocaine synthase. The enzyme is capable of producing both cocaine and cinnamoylcocaine via the activated benzoyl- or...