Aphylline, epiaphylline, 10,17-dioxosparteine, gramine, and other unexpected alkaloids from Lupinus hartwegii

Anderson, J.C.; Martin, R. L.

doi:10.1021/jo00883a026

Cited by 18 publications

(4 citation statements)

References 5 publications

(7 reference statements)

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“…calcaratus was not surprising in view of the concurrent presence of gramodendrine in this plant. Gramine was originally obtained from the leaves of germinating barley (Von Euler and Erdtmann, 1935) and has since been isolated from a number of different plants including several species of lupine (Mears and Mabry, 1971; Anderson and Martin, 1976). These phytochemical data demonstrate L. arbustus subsp.…”

Section: Resultsmentioning

confidence: 99%

Identification of toxic alkaloids from the calcaratus subspecies of Lupinus arbustus

Hatfield¹,

Yang²,

Ferguson³

et al. 1985

J. Agric. Food Chem.

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Section: Resultsmentioning

confidence: 99%

Identification of toxic alkaloids from the calcaratus subspecies of Lupinus arbustus

Hatfield¹,

Yang²,

Ferguson³

et al. 1985

J. Agric. Food Chem.

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“…Combined GC/MS has been used to identify quinolizidine alkaloids from Lupinus species previously, without the need for solute derivatization (Anderson and Martin, 1976;Kinghorn et al, 1980). Six alkaloids were identified from a sample of L. sericeus, collected in Utah in June 1964 by using this technique (Table I).…”

Section: Resultsmentioning

confidence: 99%

Reinvestigation of the alkaloids of Lupinus sericeus Pursh. Identification of a new natural product, 10,17-dioxo-.beta.-isosparteine

Ic¹,

Mf²,

Kinghorn³

1982

J. Agric. Food Chem.

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0 5 10 15 20 25 TIME HOURSFigure 4. Rate of reaction of nifluridide at pH 9.0 with the formation of EL-919.balance was obtained by adding together the concentrations of nifluridide and EL-919 (as its nifluridide molecular weight equivalent). RESULTS AND DISCUSSIONThe rapid conversion of nifluridide to EL-919 proceeds as indicated in Figure 1. The rates of disappearance and the corresponding formation of EL-919 are plotted on a semilogarithmic scale in Figures 2-4. The cyclization proceeded via a first-order reaction with half-lives of 15.5, 3.5, and 2.0 h for EL-468 at pH 5.0, 7.0, and 9.0, respectively. The total amount of nifluridide and EL919 present in the final samples analyzed provided a good material balance (80-100%) compared to the initial amount of chemical in the aqueous solutions (Figures 2-4). No other hydrolysis products were observed.On the basis of these results, nifluridide would likely dissipate very rapidly in natural water or in the presence of soil moisture. Thus, the parent compound would not be expected to persist in the environment.Chromatograms demonstrating the determination of both compounds in the aqueous solutions are shown in Figure 5. The direct injection of the solutions into the reverse-phase HPLC system at specified intervals, which were programmed into the WISP, provided an automated rate study by eliminating the need to extract the buffered solutions with a suitable solvent, concentrate the sample U W ----0 5 10 15 0 5 10 15 0 5 10 15 0 5 10 15 c TIME, MINUTES Figure 5. Chromatograms demonstrating the dissipation of nifluridide and the formation of EL-919 at pH 9.0 (A) nifluridide standard, 0.8 pg; (B) EL-919 standard, 0.8 pg; (C) reaction solution at 2 h (45.8% nifluridide, 49.1% EL-919); (D) reaction solution a t 10 h (2.9% nifluridide, 105.7% EL-919).extract, and redissolve the residue in a suitable solvent for injection into the HPLC. It is probable that this direct injection technique could also be applied to many other compounds of environmental interest that are highly labile in aqueous solution.

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“…Interestingly, in 1959, gramine was first discovered in Acer saccharinum, with 1.1 g of prismatic crystals obtained from 3.75 kg of dried maple leaves, which are widely distributed in the United States and southeastern Canada [8]. Then, in 1976, Anderson et al extracted 85 mg of gramine from 640 g of seeds of Lupinus hartwegii (six weeks old) grown in vermiculite [9]. In 1985, Zú ecules 2023, 28, x FOR PEER REVIEW 2 of 17 the chemical synthesis of gramine and its derivatives; and (iii) the diverse biological activities.…”

Section: Extraction and Separationmentioning

confidence: 99%

Recent Developments of Gramine: Chemistry and Biological Activity

Zhang

Jia

et al. 2023

Molecules

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The natural alkaloid gramine has attracted significant attention in both academic and industrial circles because of its potential and diverse biological activities, including antiviral, antibacterial, antifungal, anti-inflammatory and antitumor activities; application in therapy for Alzheimer’s disease; serotonin-receptor-related activity; insecticidal activity; and application as an algicide. In this review, we focus on the research advances that have been made for gramine-based molecules since their discovery, providing key information on their extraction and separation, chemical synthesis and diverse biological activities. Data regarding their mechanisms of action are also presented. This comprehensive and critical review will serve as a guide for developing more drug candidates based on gramine skeletons.

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Aphylline, epiaphylline, 10,17-dioxosparteine, gramine, and other unexpected alkaloids from Lupinus hartwegii

Cited by 18 publications

References 5 publications

Identification of toxic alkaloids from the calcaratus subspecies of Lupinus arbustus

Identification of toxic alkaloids from the calcaratus subspecies of Lupinus arbustus

Reinvestigation of the alkaloids of Lupinus sericeus Pursh. Identification of a new natural product, 10,17-dioxo-.beta.-isosparteine

Recent Developments of Gramine: Chemistry and Biological Activity

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