β-Phenylethylamines and the isoquinoline alkaloids

Bentley, K. W.

doi:10.1039/b509523a

Cited by 451 publications

(155 citation statements)

References 105 publications

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“…Although there are no reports of the occurrence of these compounds in Piper gaudichaudianum, two aporphinoid alkaloids, cepharadione A and piperolactam E, were isolated from Piper caninum and Piper taiwanense, respectively. 30 …”

Section: Resultsmentioning

confidence: 99%

Biosynthetic Insights into p-Hydroxybenzoic Acid-Derived Benzopyrans in Piper gaudichaudianum

Batista¹,

Batista²,

Souza-Moreira³

et al. 2017

J. Braz. Chem. Soc.

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Piper gaudichaudianum Kunth (Piperaceae) accumulates gaudichaudianic acid, a prenylated benzopyran, as its major component. Interestingly, this trypanocidal compound occurs as a racemic mixture. Herein, transcriptomic investigations of Piper gaudichaudianum using the RNAseq approach are reported, and from the analysis of the transcripts expressed it was possible to propose a complete biosynthetic pathway for the production of gaudichaudianic acid, including the steps that originate its precursor, p-hydroxybenzoic acid. Peperomia obtusifolia (L.) A. Dietr. (Piperaceae) also accumulates racemic benzopyrans, however, its chromanes originate from the polyketide pathway, while the chromenes from Piper derives from the shikimate pathway. Recent transcriptomic and proteomic studies of the former species did not identify polyketide synthases involved in the production of the benzopyran moiety, but revealed the expression of tocopherol cyclase, which may be responsible for the cyclization of the 3,4-dihydro-2H-pyran ring. The analysis of the enzymes involved in the secondary metabolism of Piper gaudichaudianum and the comparison with the data previously obtained from Peperomia obtusifolia can provide valuable information on how these compounds are biosynthesized.Keywords: Piperaceae, chromene, transcriptome, RNA-seq, de novo assembly, biosynthesis IntroductionChromanes and chromenes, which are secondary metabolites commonly found in some species from Piper and Peperomia genera (Piperaceae), are characterized by the presence of a benzopyran ring with various levels of oxidation. [1][2][3] This nucleus is considered a privileged structure that is very common in bioactive natural products, such as coumarins, flavones, tocopherols (vitamin E) and tetrahydrocannabinoids. 4,5 The benzopyran moieties, 2H-chromenes and chromanes, isolated from Piper gaudichaudianum and Peperomia obtusifolia, respectively, have been demonstrated as potent trypanocidal compounds. 6,7 Curiously, both classes of compounds occur as racemic mixtures in these species, though their formation follows two distinct biosynthetic routes. 6,8,9 In Piper gaudichaudianum, chromenes originate from the shikimate pathway and use p-hydroxybenzoic acid (p-HBA) as a precursor. 10 In the case of Peperomia obtusifolia, chromanes are formed through the polyketide pathway and use orsellinic acid as a precursor. 1,11 Additionally, the formation of both classes of metabolites involves the condensation of an aromatic unit (p-HBA or orsellinic acid) and an isoprene unit (dimethylallyl pyrophosphate, isopentenyl pyrophosphate or geranyl pyrophosphate), followed by cyclization that gives rise to the benzopyran ring. During cyclization, the carbon atom at C-2 becomes a stereogenic center and, different from other benzopyrans such as vitamin E, both enantiomers are biosynthesized (Figure 1). Thus, the study of the proteins and genes possibly responsible for the biosynthesis of benzopyrans in these species, as well as the comparison between them, may provide new insights into how...

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Section: Resultsmentioning

confidence: 99%

Biosynthetic Insights into p-Hydroxybenzoic Acid-Derived Benzopyrans in Piper gaudichaudianum

Batista¹,

Batista²,

Souza-Moreira³

et al. 2017

J. Braz. Chem. Soc.

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“…Supplementary data ( 1 H, 13 C spectra of representative compounds and crystal data of 3a) and general information associated with this article can be found in the supporting information …”

Section: Supplementary Datamentioning

confidence: 99%

“…[10][11] On the other hand, kojic acid, a natural pyrone fungal metabolite and a common by-product in the fermentation of soy sauce, sake, rice wine and usually employed as food additive to prevent oxidative browning and also as depigmentation agent in cosmetics. [12][13][14][15] Some of the kojic acid derivatives are reported to exhibit antimicrobial property against a variety of bacteria, fungi, 16 and displayed their potential as a polyfunctional backbone for new antimicrobial agents. 17 In general; combination of two different heterocyclic moieties in a single framework often enhances the biological properties remarkably.…”

Section: Graphical Abstractmentioning

confidence: 99%

One-pot catalyst free synthesis of novel kojic acid tagged 2-aryl/alkyl substituted-4H-chromenes and evaluation of their antimicrobial and anti-biofilm activities

Bingi

Emmadi

Chennapuram

et al. 2015

Bioorganic & Medicinal Chemistry Letters

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“…A comprehensive review on kojic acid, and a critical review on metal complexes of hydroxypyrones in medicinal inorganic chemistry have been recently published [1,2]. HKa, recognized at first as an antibiotic substance, has antibacterial and antifungal properties, and inhibits the rate of the formation of pigmented products in plant and in animal tissue, as well as the rate of oxygen uptake when o-dihydroxy-and trihydroxy phenols are oxidized by tyrosinase [3][4][5][6].…”

Section: Introductionmentioning

confidence: 99%

Iron(III) and aluminum(III) complexes with hydroxypyrone ligands aimed to design kojic acid derivatives with new perspectives

Nurchi

Crisponi

Lachowicz

et al. 2010

Journal of Inorganic Biochemistry

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β-Phenylethylamines and the isoquinoline alkaloids

Cited by 451 publications

References 105 publications

Biosynthetic Insights into p-Hydroxybenzoic Acid-Derived Benzopyrans in Piper gaudichaudianum

Biosynthetic Insights into p-Hydroxybenzoic Acid-Derived Benzopyrans in Piper gaudichaudianum

One-pot catalyst free synthesis of novel kojic acid tagged 2-aryl/alkyl substituted-4H-chromenes and evaluation of their antimicrobial and anti-biofilm activities

Iron(III) and aluminum(III) complexes with hydroxypyrone ligands aimed to design kojic acid derivatives with new perspectives

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