Isolation, Structure, and Synthesis of Novel 4-Quinolinone Alkaloids from Esenbeckia leiocarpa

Nakatsu, Tetsuo; Johns, Timothy; Kubo, Isao; Milton, Katharine; Sakai, Masami; Chatani, Katsuhiro; Saito, Ken; Yamagiwa, Yoshiro; Kamikawa, Tadao

doi:10.1021/np50072a017

Cited by 45 publications

(35 citation statements)

References 3 publications

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“…is a climax species endemic to the Atlantic Forest in Brazil with a high density of individuals per population (> 100 trees/ha, Seoane et al 2001). This species is used for various purposes, including civil construction, as a medicinal plant (treatment for Alzheimer's disease), and additionally has allelopathic effects that may be used in crop farming (Nakatsu et al 1990, Sousa et al 2010. E. leiocarpa fl owers are hermaphroditic and pollination occurs by fl ies.…”

Section: Introductionmentioning

confidence: 99%

Low genetic diversity and intrapopulation spatial genetic structure of the Atlantic Forest tree, Esenbeckia leiocarpa Engl. (Rutaceae)

et al. 2014

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Abstract. Studies on population genetics are the key to designing effective in situ management plans for tree species, in particular, those subjected to pressure from anthropogenic processes, such as forest fragmentation and logging. To investigate genetic diversity, inbreeding and intrapopulation spatial genetic structure (SGS) in a fragmented population of the insect-pollinated tropical tree, Esenbeckia leiocarpa, we developed specific microsatellite markers for this species and mapped and sampled 100 individuals in a forest plot. Two issues were addressed in particular: (i) the level of genetic diversity, inbreeding and effective population size, (ii) whether intrapopulation spatial genetic structure exists. Among the 14 loci developed, we only used the three that presented polymorphism to estimate the genetic parameters. Genetic diversity was low, whereby the average number of alleles per locus (A) was 3.3 and observed (H 0 ) and expected heterozygosities (H e ) were 0.336 and 0.298, respectively. The average fixation index was significantly higher than zero (F = 0.112), suggesting inbreeding. Significant SGS was found up to 7 m and between 31 to 38 m, indicating that trees growing within these distances may be related. Estimates of the effective population size indicated that the 100 sampled trees correspond to 14 individuals that are neither related nor inbred. Our results suggest that the microsatellite markers developed in this study are suitable for studies on genetic diversity and structure, mating systems, gene flow and SGS in this species.

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Section: Introductionmentioning

confidence: 99%

Low genetic diversity and intrapopulation spatial genetic structure of the Atlantic Forest tree, Esenbeckia leiocarpa Engl. (Rutaceae)

et al. 2014

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“…All reactions involving air-sensitive reagents were performed under nitrogen in oven-dried glassware using the syringe-septum cap technique. 1 H NMR (300 MHz), 13 C NMR (75 MHz) spectra were recorded in deuterated solvents with tetramethylsilane (TMS, d = 0 ppm) as internal standard. Mass spectra were recorded on a Varian MAT 112 spectrometer (EI, 70 eV) by using GC-MS coupling or via a direct inlet system on a Agilent 1100 Series VS (ESI, 4000 V).…”

Section: Experimental Generalmentioning

confidence: 99%

New general synthesis of α-alkoxyketones via α′-alkylation, α-alkylation and α,α′-dialkylation of α-alkoxyketimines

et al. 2011

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a-Methoxy-and a-ethoxyketones, as important intermediates in organic synthesis and flavor compounds in food chemistry, were synthesized by deprotonation of N-(1-alkoxy-2-propylidene)isopropylamine, prepared by condensation of the corresponding a-alkoxyacetone with isopropylamine, and subsequent reaction of the corresponding 1-azaallylic anions with alkyl halides to afford a¢-alkylated, a-alkylated and a,a¢-dialkylated ketimines. Hydrolysis of the imino function led to the desired substituted a-alkoxyketones. The ratio of a-, a¢-, and a,a¢-(di)alkylated compounds depended on the amount of base used and on the nature of the alkylating reagent.

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“…4,5 Metabolites isolated from E. leiocarpa exhibited antifeedant activity against worm Pectinophora gossypiella. 6 In addition, a geranylcoumarin has been isolated from E. febrifuga, which significantly inhibited the growth of tropical parasite Leishmania major. 7 Phytochemical studies on this genus has allowed the isolation of several secondary metabolites such as flavonoids from E. yaxhoob, 4 E. grandiflora subsp.…”

Section: Introductionmentioning

confidence: 99%

Quinoline alkaloids and friedelane-type triterpenes isolated from leaves and wood of Esenbeckia alata kunt (Rutaceae)

Suárez¹,

Coy-Barrera²,

Caballero³

2011

Quím. Nova

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This work describes the phytochemical exploration of the ethanol extract from leaves and wood of Esenbeckia alata, leading to the isolation and identification of quinoline alkaloids 4-methoxy-3-(3'-methyl-but-2'-enyl)-N-methyl-quinolin-2(1 H)-one, N-methylflindersine, dictamine, kokusaginine, Γ-fagarine, flindersiamine, as well as the fridelane-type triterpenes, frideline, fridelanol and its acetate derivative. Identification of these compounds was based on full analyses of spectroscopic data (¹H, 13C, 1D, 2D, IR, MS) and comparison with data reported in literature. Compound 4-methoxy-3-(3'-methyl-but-2'-enyl)-N-methyl-quinolin-2(1 H)-one is reported for the first time for the genus Esenbeckia

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Isolation, Structure, and Synthesis of Novel 4-Quinolinone Alkaloids from Esenbeckia leiocarpa

Cited by 45 publications

References 3 publications

Low genetic diversity and intrapopulation spatial genetic structure of the Atlantic Forest tree, Esenbeckia leiocarpa Engl. (Rutaceae)

Low genetic diversity and intrapopulation spatial genetic structure of the Atlantic Forest tree, Esenbeckia leiocarpa Engl. (Rutaceae)

New general synthesis of α-alkoxyketones via α′-alkylation, α-alkylation and α,α′-dialkylation of α-alkoxyketimines

Quinoline alkaloids and friedelane-type triterpenes isolated from leaves and wood of Esenbeckia alata kunt (Rutaceae)

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