Abstract

The genus Datura (Solanaceae) contains nine species of medicinal plants that have held both curative utility and cultural significance throughout history. This genus’ particular bioactivity results from the enormous diversity of alkaloids it contains, making it a valuable study organism for many disciplines. Although Datura contains mostly tropane alkaloids (such as hyoscyamine and scopolamine), indole, beta-carboline, and pyrrolidine alkaloids have also been identified. The tools available to explore specialized metabolism in plants have undergone remarkable advances over the past couple of decades and provide renewed opportunities for discoveries of new compounds and the genetic basis for their biosynthesis. This review provides a comprehensive overview of studies on the alkaloids of Datura that focuses on three questions: How do we find and identify alkaloids? Where do alkaloids come from? What factors affect their presence and abundance? We also address pitfalls and relevant questions applicable to natural products and metabolomics researchers. With both careful perspectives and new advances in instrumentation, the pace of alkaloid discovery—from not just Datura—has the potential to accelerate dramatically in the near future.

Highlights

  • Perhaps no plants on Earth have been more famous—and infamous—throughout history than those in the genus Datura

  • The exact composition and type of alkaloids found changes with plant age as well: in the roots of yellowed, senile D. stramonium plants harvested in autumn, only five alkaloids were detected by Gas Chromatography-Mass Spectrometry (GC-mass spectrometry (MS)), suggesting very slow tropane alkaloid synthesis, whereas forty-two different tropane alkaloids were detected in the roots while the fruits were maturing [72]

  • To understand how alkaloids are synthesized, what their ultimate roles in the plant may be, how they relate to substances found in similar plants, or what bioactivities they may have, more of their structures need to be known, and known unambiguously beyond the putative annotations that dominate the literature

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Summary

Introduction

A complex, multidisciplinary effort with contributions from drug discovery and pharmacology, plant breeding and bioengineering, evolutionary biology, analytical chemistry, and ethnobotany has sought to elucidate the peculiar and powerful properties of these plants and the substances within that cause them. This comprehensive review covers the alkaloids of Datura, the tools used to detect and identify them, the factors affecting their content and composition, and challenges facing the plant natural products field as a whole. This information could aid anyone interested in discovering novel alkaloids or studying plant breeding or engineering systems for alkaloid production

Medicine and Culture
Description
Flower
Extraction and Purification of Alkaloids
Other Mass Spectrometry Methods
15 N-labeled
H-15 N-HMBC
History—And Some Troublesome Aspects of Identifying and aReporting
H-1 H COSY
Alkaloids of the Genus Datura—Tropane Alkaloids
Chirality
Biosynthesis
Trisubstituted
Disubstituted Tropanes
Trisubstituted and Epoxytropanes
Alkaloids
Pyrrolidines
Miscellaneous Alkaloids
Factors
Location within the Plant
Ploidy of Plants
Light and Water Amount
Chemical Additives
Insect Herbivory
Findings
Conclusions and Future Challenges
Full Text
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