Biogenesis of Hyoscyamine

  title={Biogenesis of Hyoscyamine},
  author={E. Leete and L. Marion and I. D. Spenser},
THE biogenetic origin of the tropane bases has recently been the subject of some discussion1,2, Mortimer1 suggesting that the tropane skeleton may be derived from the breakdown products of tryptophan metabolism. This novel idea is contrary to the accepted hypothesis that a base such as tropine is produced in vivo by reactions analogous to the in vitro synthesis3 of tropinone from succindialdehyde, methylamine and acetone. The succindialdehyde is considered to be a metabolite of ornithine, and… Expand
Tropane and Related Alkaloids
Tropane alkaloids comprise a large group of bases occurring predominantly in the family of the Solanaceae. Structurally they are esters of carboxylic acids with tropineExpand
Tropane alkaloid biosynthesis: a centennial review.
The aim of this review is to present the innovative ideas and results in exploring the story of tropane alkaloid biosynthesis in plants from 1917 to 2020 and underscores the importance of total synthesis in the study of natural product biosynthesis. Expand
Chapter 5 The Tropane Alkaloids
Publisher Summary This chapter discusses the tropane alkaloids. The rich field of the tropane alkaloids has been investigated intensively in the last five years. The main features of this researchExpand
Biogenetic-type syntheses of natural products.
During the past fifty to sixty years, tremendous advances have been made in the laboratory preparation of complex, naturally occurring organic substances. As early as the first part of the presentExpand
Synthesis of tropine-labeled atropine. I. Micro methods for the synthesis of tropine and for its esterification with tropic acid.
The procedures are designed for the synthesis of labeled tropine and tropine-labeled atropine from labeled arabinose and the results show that micro quantities of reactants routinely produce 67–72 per cent of theoretical tropine yields. Expand
Synthesis of tropine-labeled atropine. IV. Labeling of the 2, 3, and 4 positions of atropine from citric-14-C acid.
This is the first reported syntheses of tropine or atropine labeled with 14C in positions other than the endo-methyl group. Expand
Tropinone synthesis via an atypical polyketide synthase and P450-mediated cyclization
The authors discovered the enzymes AbPYKS and AbCYP82M3, a non-canonical polyketide synthase and a cytochrome P450, that work sequentially to form tropinone from N-methyl-Δ1-pyrrolinium cation. Expand
Recent development in the synthesis and stereochemistry of tropane alkaloids
Abstract Two years ago several comprehensive reviews1,2,3,4 on the stereochemistry of tropane alkaloids which dealt with earlier and more recent results were presented. Since then, however, anExpand
Tropane alkaloids biosynthesis involves an unusual type III polyketide synthase and non-enzymatic condensation
This study provides a long sought-after biosynthetic mechanism to explain condensation between N-methylpyrrolinium and acetate units and identifies an unusual plant type III polyketide synthase that can only catalyze one round of malonyl-CoA condensation. Expand
Chapter 1 Alkaloids in the Plant
This chapter discusses the alkaloids in the plant, and it is suggested that phylogenetical evolution not only involved morphological differentiation but that chemical differentiation is parallel to it and even forms its basis. Expand


A Possible Common Biogenetic Origin of the Nicotine, Tropane and Hygrine Bases
THE isolation of both hyoscine and nicotine from a genotype of Duboisia myoporoides1 suggests the possibility of a close biosynthetic relation between these bases, and is consequently of interest inExpand
Biogenesis of Alkaloids of Solanaceæ
THIRTY-SIX years ago1 I directed attention to the structural relations between hygrine, cuskhygrine, tropine and other similar bases, and drew the conclusion that the units concerned in theExpand
Biosynthesis of the Belladonna Alkaloids
The study of alkaloid metabolism may be expected to yield much information valuable to the wider study of the plant's nitrogen metabolism in general. Expand
Putrescine-1: 4-C14 was fed to mature Daturastramonium in an investigation of the biosynthesis of l-hyoscyamine. Although C14 was metabolized by the plant, no radioactivity was found in the isolate...
Action of Ninhydrin on Keratin
The basic side-chains of keratin must play a fundamental part in the cross-linking reaction, since no strengthening is obtained with completely deaminated fibres, and the extent of reaction is reduced when the lysine side- chains are blocked by means of 1-fluoro-2 : 4-dinitrobenzene or nitroso-benzenes. Expand