Quinoline alkaloids from Sebastiania corniculata (Euphorbiaceae)

Machado, Daniela de Nazaré M.; Júnior, Sebastião F. Palmeira; Conserva, Lúcia M.; Lemos, Rosangela P. de Lyra

doi:10.1016/j.bse.2004.08.004

Cited by 7 publications

(1 citation statement)

References 11 publications

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“…Chemophenetics do not aim to elucidate phylogenetic relationships but to describe the matrix of natural products and use them for the phenetic characterization of clades [ 6 ]. Several studies using chemophenetic and chemotaxonomic approaches have been described in the literature, including several genera of the Euphorbiaceae such as Senefelderopsis [ 7 ], Euphorbia [ 8 , 9 , 10 ], Mallotus [ 5 ], Chrozophora [ 11 ], Croton [ 12 ], Alchornea [ 13 ], Sapium [ 14 ], and Sebastiania [ 15 ], among other examples.…”

Section: Introductionmentioning

confidence: 99%

Chemophenetic Significance of Anomalocalyx uleanus Metabolites Are Revealed by Dereplication Using Molecular Networking Tools

et al. 2021

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Anomalocalyx uleanus (Pax & K. Hoffm.) Ducke (Euphorbiaceae) is a singular species in the genus and is restricted and exclusive to the Brazilian Amazon. A phytochemical study of A. uleanus leaves was performed, yielding the isolation of five major compounds: catechin/epicatechin, afzelin, quercetin 3-O-α-L-rhamnopyranoside, and astilbin. The phytochemical compositions of the methanolic extracts of leaves, roots, bark, and stem bark were determined using a dereplication approach. Forty-six compounds were annotated from the liquid chromatography-mass spectrometry (LC-MS/MS) data, while four lipids were identified using gas chromatography-mass spectrometry (GC-MS). In total, fifty compounds were detected, and they belonged to the primary metabolism and several classes of natural products such as flavonoids, flavonoids O-glycosides, flavonoids C-glycosides, biflavonoids, procyanidin, triterpene, triterpenes esterified with phenylpropanoids, phenylpropanoid derivatives, flavonolignans, coumarins, quinic acid derivatives, and benzoic acid derivatives. This is the first report on the phytochemical data of the genus Anomalocalyx, and the results of this study will contribute to the chemosystematic knowledge of the Euphorbiaceae family and justify the need for investigation of the pharmacological potential of the species A. uleanus.

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Section: Introductionmentioning

confidence: 99%

Chemophenetic Significance of Anomalocalyx uleanus Metabolites Are Revealed by Dereplication Using Molecular Networking Tools

et al. 2021

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Reactivity of 2-Methyl-4H-3,1-benzoxazin-4-ones and 2-Methyl-4H-pyrido[2,3-d][1,3]oxazin-4-one under Microwave Irradiation Conditions

Prousis

Tzani

Avlonitis

et al. 2013

J. Heterocyclic Chem.

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The reactivity of variably substituted 2‐methyl‐4H‐3,1‐benzoxazin‐4‐ones and 2‐methyl‐4H‐pyrido[2,3‐d][1,3]oxazin‐4‐one towards carbon and oxygen nucleophiles under microwave irradiation conditions was investigated. Optimization of the reaction conditions of oxazinones with carbon nucleophiles led to the synthesis of a series of 4‐hydroxy‐quinolin‐2‐ones and 4‐hydroxy‐1,8‐naphthyridin‐2‐ones in high yields, whereas reaction with a variety of alcohols proceeded smoothly to the formation of the corresponding N‐acetyl‐anthranilates and nicotinates.

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Structural analogues of quinoline alkaloids: Straightforward route to [1,3]dioxolo[4,5‐c]quinolines with antibacterial properties

Horák

Kořistek

Šamšulová

et al. 2020

Journal of Heterocyclic Chem

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Compounds bearing [1,3]dioxolo‐quinoline scaffolds have been found in quinoline‐based natural products; the only exception is the [1,3]dioxolo[4,5‐c]quinoline moiety with a rare occurrence in both natural and synthetic derivatives. In this article, we report the preparation of diversely substituted and functionalized [1,3]dioxolo[4,5‐c]quinolines using [1,3]dioxolo[4,5‐c]quinoline‐4‐carbaldehyde (DQC) as the common intermediate. DQC was synthesized on a large scale from anthranilic acid and chloroacetone as the starting materials, with the rearrangement of acetonyl‐anthranilate as the key step. The developed method allows for the simple preparation of [1,3]dioxolo[4,5‐c]quinolines with various C2 substituents on the quinoline scaffold. Additionally, the synthetic route was successfully applied to the preparation of 3‐hydroxyquinoline‐4(1H)‐ones. The target compounds were tested against representative Gram‐positive/negative bacteria, and two derivatives exhibited submicromolar minimum inhibitory concentrations against Micrococcus luteus.

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Quinoline alkaloids from Sebastiania corniculata (Euphorbiaceae)

Cited by 7 publications

References 11 publications

Chemophenetic Significance of Anomalocalyx uleanus Metabolites Are Revealed by Dereplication Using Molecular Networking Tools

Chemophenetic Significance of Anomalocalyx uleanus Metabolites Are Revealed by Dereplication Using Molecular Networking Tools

Reactivity of 2-Methyl-4H-3,1-benzoxazin-4-ones and 2-Methyl-4H-pyrido[2,3-d][1,3]oxazin-4-one under Microwave Irradiation Conditions

Structural analogues of quinoline alkaloids: Straightforward route to [1,3]dioxolo[4,5‐c]quinolines with antibacterial properties

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