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Alkaloids Derived from Anthranilic Acid: Quinoline, Acridone, and Quinazoline

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Natural Products

Abstract

In this chapter, some of the latest developments in the groups of natural products collectively known as the quinolin/one, quinazolin/one, and acridone alkaloids are presented. Emphasis is placed on their biogenesis, biological activities, and natural distribution. Quinolin/ones and acridones undoubtedly occur in greatest abundance in plants from the Rutaceae family. The 2-alkylquinolin/4(1H)-ones are typical constituents of the Rutaceae but, surprisingly, they have also been isolated from some bacteria, mainly from Pseudomanas. Fungus Penicillium has yielded a novel class of quinolin/ones, which is based on the combination of amino acids l-valine and l-isoleucine, anthranilic acid, and acetic acid, or these amino acids and tryptamine. They constitute two small groups quinolactacins and quinocitrinines, which are alkaloid types at present unknown from any other source. Quinazoline derivatives are less common in Rutaceae, and a variety of them are produced by bacteria, fungi, and marine animals. In recent years, a number of these alkaloids have been found to possess real pharmacological activity, which is discussed.

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Abbreviations

ACP:

Acyl carrier protein

AMP:

Adenosine monophosphate

Ant:

Anthranilic acid

ATP:

Adenosine triphosphate

AuaAE:

Genes required for quinoline alkaloid aurachin synthesis

CF:

Cystic fibrosis

CML:

Chronic myelogenous leukemia

CoA:

Coenzyme A as part of a thioester, e.g., acetyl-CoA (CH3COSCoA)

CoASH:

Coenzyme A

DMAPP:

Dimethylallyl diphosphate

FPP:

Farnesyl diphosphate

GC-MS:

Gas chromatograph-mass spectrometry

Ger:

Geranyl

Gln:

Glutamine

INCA:

Instituto Nacional do Cancer (Brazil – www.inca.gov.br)

l-Ala:

l-alanine

l-Asp:

Aspartic acid

l-Trp:

l-tryptophan

NADP+ :

Nicotinamide adenine dinucleotide phosphate

NADPH:

Nicotinamide adenine dinucleotide phosphate (reduced)

NMR:

Nuclear magnetic resonance spectroscopy

NRPS:

Nonribosomal peptide synthetase

Phe:

Phenylalanine

PKSs:

Polyketide synthases

PPi:

Inorganic diphosphate

PQS:

Pseudomonas quinolone signal

pqsABCD:

Genes required for PQS synthesis

pqsE:

The function of the pqsE gene is not known but it is required for PQS synthesis

Pro:

Proline

TNF:

Tumor necrosis factor

Val:

Valine

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Acknowledgments

The authors thank the Brazilian agencies: Institutos Nacionais de Ciência e Tecnologia, do Conselho Nacional de Desenvolvimento Cientifico e Tecnológico (CNPq/MCT, INCT, 573742/2008-1), Fundação de Amparo a Pesquisa do Estado de São Paulo (FAPESP, INCT, 08/57859-5), Coordenação de Aperfeiçoamento de Pessoal de Ensino Superior (CAPES), and Financiadora de Estudos e Projetos (FINEP) for their financial support.

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  1. Departamento de Química, Universidade Federal de São Carlos, 13565-905, São Carlos, SP, Brazil

    Dr. Maria Fátima das Graças Fernandes da Silva, João Batista Fernandes, Moacir Rossi Forim, Paulo Cezar Vieira & Israel Cívico Gil de Sá

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  1. Dr. Maria Fátima das Graças Fernandes da Silva
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  2. João Batista Fernandes
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Correspondence to Maria Fátima das Graças Fernandes da Silva .

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  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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da Silva, M.F.d.G.F., Fernandes, J.B., Forim, M.R., Vieira, P.C., de Sá, I.C.G. (2013). Alkaloids Derived from Anthranilic Acid: Quinoline, Acridone, and Quinazoline. In: Ramawat, K., Mérillon, JM. (eds) Natural Products. Springer, Berlin, Heidelberg. https://doi.org/10.1007/978-3-642-22144-6_25

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