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Terpenoid Alkaloids Derived by Amination Reaction

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Natural Products

Abstract

Terpenoid alkaloids are a class of pseudoalkaloids, in which a nitrogen atom is inserted in the skeleton on a late biosynthetic stage. This class of compounds, sharing structural diversity, interesting chemistry, and promising pharmacological properties, has for a long time stimulated the interest of the scientific community and is covered in this chapter. The occurrence, phytochemistry with classification, and biological activities of monoterpenoid alkaloids reported between 2000 and Feb. 2012 and that of diterpenoid alkaloids reported between 2009 and Feb. 2012 are presented together with the biosynthetic approaches.

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Abbreviations

6T-CEM:

Human acute T lymphocyte leukemia cell line

AChBP:

Acetylcholine-binding protein

ED50 :

Effective dose fifty percent

ent-CPP:

Ent-copalyl diphosphate

GA–MLRs:

Genetic algorithm–multiple linear regressions

GA–PLS:

Genetic algorithm–partial least squares

GGPP:

Geranylgeranyl pyrophosphate

hERG:

Human ether-á-go-go-related gene

HR-ESI-MS:

High-resolution electrospray ionization mass spectrum

IR:

Infrared

LoVo:

Human colon carcinoma cell line

MCF-7:

Michigan Cancer Foundation-7

MDA-MB-435:

Human breast carcinoma cell

MLA:

Methyllycaconitine

MTT:

3-(4,5-dimethylthiazol-2-yl)-2,5-diphenyltetrazolium bromide

nAChR:

Nicotinic acetylcholine receptor

NMR:

Nuclear magnetic resonance

nor-BNI:

Norbinaltorphimine

NTI:

Naltrindole

QSAR:

Quantitative structure–activity relationship

SRB:

Sulforhodamine B

β-FNA:

β-funaltrexamine

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Author information

Authors and Affiliations

  1. Molecular Targets Laboratory, Center for Cancer Research, Frederick National Laboratory for Cancer Research, Frederick, MD, 21702, USA

    Dr. Krishna Prasad Devkota

  2. Organic and Bioorganic Chemistry, Department of Chemistry, Bielefeld University, 10 01 31, Bielefeld, 33501, Germany

    Prof. Norbert Sewald

Authors
  1. Dr. Krishna Prasad Devkota
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  2. Prof. Norbert Sewald
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Correspondence to Krishna Prasad Devkota .

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Editors and Affiliations

  1. Botany Department, M.L. Sukhadia University, Durga Nursery Road, Udaipur, 313001, Rajasthan, India

    Kishan Gopal Ramawat

  2. Institute of Vine and Wine Sciences, Biological-Active Plant Substances Study, University of Bordeaux, 210 Chemin de Leysotte CS 50008, Villenave d'Ornon, 33882, France

    Jean-Michel Mérillon

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Devkota, K.P., Sewald, N. (2013). Terpenoid Alkaloids Derived by Amination Reaction. In: Ramawat, K., Mérillon, JM. (eds) Natural Products. Springer, Berlin, Heidelberg. https://doi.org/10.1007/978-3-642-22144-6_30

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