Two New Alkylated Piperidine Alkaloids from Western Honey Mesquite: Prosopis glandulosa Torr. var. torreyana

Samoylenko, Volodymyr; Dunbar, D. Chuck; Jacob, Melissa R.; Joshi, Vaibhav; Ashfaq, Muhammad; Ilias, Mohammad

doi:10.1055/s-2008-1075314

Cited by 3 publications

(6 citation statements)

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“…The last is one of the most relevant members of the "lipid alkaloids," a family that also comprises prosopine, juliprosopine, cassine, and carnavaline [3][4][5][6][7]. The biological activities of these compounds range from antifungal to antimicrobial [8][9][10][11], and reports also point to their antiinflammatory properties and propose them as candidates for use in Alzheimer's disease therapy [12,13]. Several studies suggest that the mode of action of these molecules is related to their ability to interact with ion channels and transport mechanisms [12][13][14][15][16].…”

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confidence: 99%

“…The Prosopis genus, composed by more than 40 species of shrubs and trees distributed throughout Asia, Africa, and the Americas [17], is an important source of piperidine alkaloids. For example, prosopine and prosopinine have been obtained from the leaves of P. africana [4], the barks of P. glandulosa, P. nigra, P. ruscifolia, and P. vinalillo have yielded several cassine and N-methylcassine isomers [9,18], and juliprosopin and many related compounds have been isolated from the leaves of P. juliflora and P. glandulosa [5,[8][9][10][11]19]. More recently, we described the isolation and structural characterization of three new N-methylated piperidin-3-ols from the bark of P. affinis, including N-methyl-2-isocassine, N-methyl-6-isocassine, and N-methyl-6-isocarnavaline [20].…”

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confidence: 99%

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Aggregation Behavior of 6-Isocassine andN-Methyl-6-Isocassine: Insights into the Biological Mode of Action of Lipid Alkaloids

Reina¹,

Bottini²,

Bennadji

et al. 2016

Natural Product Communications

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The aggregation behavior of 6-isocassine and N-methyl-6-isocassine, two piperidin-3-ol alkaloids isolated respectively from the barks of Prosopis nigra and P. affinis, was investigated using a combination of NOE experiments and diffusion measurements in solvents of varying polarity and hydrogen bonding capacity. While the NOE enhancements for N-methyl-6-isocassine are positive, regardless of the solvent, those for 6-isocassine shift from negative to positive when going from chloroform-d to methanol-d 4 solution. In addition, despite the self-diffusion coefficients of both compounds being virtually identical in methanol-d 4 , N-methyl-6-isocassine diffuses nearly twice as fast as the non-methylated alkaloid in chloroform-d. The changes in rotational and translational dynamics observed between solvents for 6-isocassine suggest that the molecule forms dimeric head-to-head aggregates in non-polar aprotic environments, a behavior that could help explain the biological mode of action that has been proposed for this type of alkaloids.

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confidence: 99%

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confidence: 99%

Aggregation Behavior of 6-Isocassine andN-Methyl-6-Isocassine: Insights into the Biological Mode of Action of Lipid Alkaloids

Reina¹,

Bottini²,

Bennadji

et al. 2016

Natural Product Communications

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“…extracts as a potential source of biopesticides has not been recently reviewed. Piperidine alkaloids have also been identified in leaves, pods, roots, and flowers of other Prosopis species, such as P. glandulosa [21,22] P. ruscifolia [23], P. africana [24], P. affinis [11], P. alpataco, P. argentina, P. chilensis, P. flexuosa and P. pugionata [9]. Two kinds of piperidine alkaloids could be found in Prosopis spp.…”

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confidence: 99%

“…Prosopis glandulosa, popularly known as honey mesquite, is a medium sized tree with spiny branches native from the north of Mexico to the south of EE.UU [50]. The polar extracts (ethanolic and aqueous) of the leaves have displayed antifungal activity and the alkaloid rich fraction derived of the extracts recorded higher activity [21,22,50]. Besides, the aqueous extract has been used to generate silver nanoparticles with antibacterial and antifungal activity [51,52].…”

Section: Prosopis Glandulosamentioning

confidence: 99%

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The Potential of Piperidine Alkaloids-rich Extracts from Prosopis spp. to Combat Plant Pests and Diseases

Muro-Medina

García-Morales

Caltempa

et al. 2022

IJBcRR

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The genus Prosopis comprises 44 species of spiny small trees adapted to arid and semiarid regions of the planet that have been used by human populations as a source of wood, food and medicine. Prosopis spp. possess high quantities of phenolic compounds and piperidine alkaloids with antioxidant, neurotoxic, antimicrobial, antimalarial, insecticidal and allelopathic activities. Juliprosopine is the major and more characterized piperidine alkaloid present in the genus Prosopis. In this review we present the potential of Prosopis spp. extracts and piperidine alkaloids for the control of plant pests and diseases and discuss the possibility of their use as an alternative in organic agriculture.

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Laboratory Evaluations of Durability of Southern Pine Pressure Treated With Extractives From Durable Wood Species

Kirker¹,

Bishell²,

Lebow³

2015

J Econ Entomol

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Extracts from sawdust of four naturally durable wood species [Alaskan yellow cedar, AYC, Cupressus nootkanansis D. Don 1824; eastern red cedar, ERC, Juniperus virginiana L.; honey mesquite, HM, Prosopis glandulosa Torr.; and black locust, BL, Robinia pseudoacacia L.] were used to treat southern pine, Pt, Pinus taeda L. sapwood blocks. Extractive treated blocks were evaluated for decay resistance in standard soil bottle fungal assays challenged with brown and white rot decay fungi. Results showed that extractives did impart some improvement to decay resistance of Pt blocks. BL- and HM-treated Pt blocks were also used in choice and no-choice assays to determine feeding preference and damage by eastern subterranean termites (Reticulitermes flavipes) Kollar. Minimal feeding on treated blocks was seen in both choice and no-choice assays. In choice assays, there was similar mortality between HM and BL arenas; however, in no-choice assays, complete mortality was recorded for HM-treated Pt and high mortality was seen with BL-treated Pt. Subsequent dose mortality termite assays showed HM to be effective in killing R. flavipes at low concentrations. Both HM and BL show promise as deterrents or termiticidal protectants and will be further evaluated in field studies.

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Two New Alkylated Piperidine Alkaloids from Western Honey Mesquite: Prosopis glandulosa Torr. var. torreyana

Cited by 3 publications

References 0 publications

Aggregation Behavior of 6-Isocassine andN-Methyl-6-Isocassine: Insights into the Biological Mode of Action of Lipid Alkaloids

Aggregation Behavior of 6-Isocassine andN-Methyl-6-Isocassine: Insights into the Biological Mode of Action of Lipid Alkaloids

The Potential of Piperidine Alkaloids-rich Extracts from Prosopis spp. to Combat Plant Pests and Diseases

Laboratory Evaluations of Durability of Southern Pine Pressure Treated With Extractives From Durable Wood Species

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