Die Konstitution des Alkaloides Juliprosopin aus <i>Prosopis</i><i>juliflora</i> A. Dc. 176. Mitteilung über organische Naturstoffe

Ott-Longoni, R.; Viswanathan, N.; Hesse, Manfred

doi:10.1002/hlca.19800630738

Cited by 54 publications

(27 citation statements)

References 15 publications

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“…23 A voucher specimen was deposited in Dungar College herbarium, Rajasthan, India (DCH5092). Samples were thoroughly washed with tap water and distilled water in order to remove any foreign particle attached to its surface and kept in oven to dry at a temperature below 50 o C. The alkaloidal extract was obtained by the method described by Ott Longoni et al 24 which is based on an acid/basic extraction process leading to the production of the alkaloid rich fraction (ARF).…”

Section: Methodsmentioning

confidence: 99%

Study of the distribution profile of piperidine alkaloids in various parts of Prosopis juliflora by the application of Direct Analysis in Real Time Mass Spectrometry (DART-MS)

Singh

Verma

2012

Nat. Prod. Bioprospect.

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Direct Analysis in Real Time Mass Spectrometry (DART-MS) was applied to identify and study the distribution profile of piperidine alkaloids in different parts of Prosopis juliflora, without isolation and separation of the compounds by standard chromatographic techniques. With the help of DART-MS, chemical fingerprint of raw plant parts were generated, which revealed the presence of piperidine alkaloids in leaf, pod and flower. A comparative study of the distribution pattern, showed variation in the presence and distribution of these alkaloids in various parts of P. juliflora. The leaves and pod displayed the largest alkaloid pattern with a total of 12 different alkaloids in each part, whereas only 4 alkaloids were present in flower. Alkaloids: julifloridine, prosopine, prosopinine and prosafrinine were ubiquitously distributed in all the alkaloid rich plant parts. Juliprosopine was pre-eminet alkaloid in leaf, whereas pod and flower displayed copious amounts of julifloridine.

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Section: Methodsmentioning

confidence: 99%

Study of the distribution profile of piperidine alkaloids in various parts of Prosopis juliflora by the application of Direct Analysis in Real Time Mass Spectrometry (DART-MS)

Singh

Verma

2012

Nat. Prod. Bioprospect.

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“…The extract was filtered, and the residue was submerged in methanol (1.5 L/kg) using the above process. An alkaloidal extract was obtained by an acid/base modified extraction as described by Ott-Longoni et al (1980). The methanol extract was concentrated in a rotary evaporation system at 40°C, and this concentrated residue was agitated with 0.2 N HCl for 16 h, followed by filtration.…”

Section: Obtaining the Total Alkaloid Extract (Tae) And Alkaloidal Frmentioning

confidence: 99%

Autophagy protects against neural cell death induced by piperidine alkaloids present in Prosopis juliflora (Mesquite)

Silva

Cuevas

Muñoz

et al. 2017

An. Acad. Bras. Ciênc.

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Prosopis juliflora is a shrub that has been used to feed animals and humans. However, a synergistic action of piperidine alkaloids has been suggested to be responsible for neurotoxic damage observed in animals. We investigated the involvement of programmed cell death (PCD) and autophagy on the mechanism of cell death induced by a total extract (TAE) of alkaloids and fraction (F32) from P. juliflora leaves composed majoritary of juliprosopine in a model of neuron/glial cell co-culture. We saw that TAE (30 µg/mL) and F32 (7.5 µg/mL) induced reduction in ATP levels and changes in mitochondrial membrane potential at 12 h exposure. Moreover, TAE and F32 induced caspase-9 activation, nuclear condensation and neuronal death at 16 h exposure. After 4 h, they induced autophagy characterized by decreases of P62 protein level, increase of LC3II expression and increase in number of GFP-LC3 cells. Interestingly, we demonstrated that inhibition of autophagy by bafilomycin and vinblastine increased the cell death induced by TAE and autophagy induced by serum deprivation and rapamycin reduced cell death induced by F32 at 24 h. These results indicate that the mechanism neural cell death induced by these alkaloids involves PCD via caspase-9 activation and autophagy, which seems to be an important protective mechanism.

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“…The 1 H and 13 C NMR spectra of 2 (Table 1) were similar to those observed for 1, except for differences associated with the presence of a dehydroindolizidine carbon skeleton, 25,26 consisting of four triplets (δ C 33.4, 21.8, 54.7, 55.5), three doublets (δC 123.8, 42.8, 65.8) and a singlet (δ C 136.1), instead of a 2,3-dihydro-1H-indolizinium nucleus 8,9 in 1 ( Table 1).…”

Section: Resultsmentioning

confidence: 52%

“…COSY and HMBC correlations led to the 13 C assignments for C-2/2′-C-7/7′ which indicated two different configurations for the alkylpiperidine rings. This was substantiated by comparing the 13 C data of the 2 β-methyl-3β-hydroxy-6β-piperidine ring of isoprosopilosine and juliprosopine (5), 25,26 suggesting two alternative structures [3 (R = X, R 1 = Y) or 3a (R = Y, R 1 = X)] for isoprosopilosine. This compound contained two different decanyl-substituted piperidine rings, where the configurations of the C-2 methyl and C-6 methylene groups were different compared to 2 or 5.…”

Section: Resultsmentioning

confidence: 89%

Indolizidine, Antiinfective and Antiparasitic Compounds from Prosopis glandulosa Torr. Var. glandulosa

Samoylenko¹,

Ashfaq²,

Jacob³

et al. 2009

Planta Med

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A new potent antiinfective and antiparasitic 2,3-dihydro-1H-indolizinium chloride, (1), was isolated from Prosopis glandulosa Torr. var. glandulosa. Three additional new (2-4) and one known (5), indolizidines were also isolated, and the dihydrochloride salts of 1-3 (compounds 6, 7 and 8) were prepared. Structures were determined by 1D and 2D NMR and mass spectra. Compound 1 showed potent in vitro antifungal activity against Cryptococcus neoformans and Aspergillus fumigatus (IC 50 values = 0.4 and 3.0 μg/mL, respectively), and antibacterial activity against methicillin-resistant Staphylococcus aureus and Mycobacterium intracellulare (IC 50 values of 0.35 and 0.9 μg/mL, respectively). The remarkable in vitro fungicidal activity of 1-4 against C. neoformans (MFCs = 0.63→1.25 μg/mL) and 2, 3, and 5 against A. fumigatus (MFCs = 0.63→2.5 μg/mL) were similar to amphotericin B, but >2-4-fold more potent than 6-8. Prosopilosidine (1) showed potent in vivo activity at 0.0625 mg/Kg/day/ip for 5 days in a murine model of cryptococcosis by eliminating ~76% of C. neoformans infection from brain tissue compared to ~83% with amphotericin B at 1.5 mg/Kg/day. Compounds 1 and 4 exhibited potent activity and high selectivity index (SI) values against chloroquine sensitive (D6) and chloroquine resistant (W2) strains of Plasmodium falciparum with IC 50 values of 39 and 95 ng/mL, and 42 and 120 ng/mL, respectively; (chloroquine, IC 50 = 17 and 140 ng/mL). Prosopilosine (1) also showed in vivo antimalarial activity with an ED 50 value of ~2 mg/Kg/day/ip against Plasmodium bergheiinfected mice after 3 days of treatment.Plants of the genus Prosopis are trees or shrubs distributed in arid and semiarid tropical and subtropical regions. P. glandulosa Torrey var. glandulosa (Leguminosae), a medium-sized * To whom correspondence should be addressed. Tel. (662) Decoctions of leaves and pods are generally used to make eye washes to treat pink eye. 5 An ethanolic extract of P. glandulosa from Pakistan yielded triterpenes, flavonoids, glycosides and the indolizidine alkaloid juliprosopine. [6][7][8][9][10] Among the indolizidines reported from Prosopis species to date, 6-11 the stereochemistry of juliprosine and juliprosopine were established by chemical synthesis. 12 The piperidinyl indolizidines, such as juliprosopine, and their analogs exhibited in vitro antibmicrobial, antidermatophytic, pesticidal, and amebicidal activities. 11,[13][14][15][16][17][18][19][20] In addition, their toxicity, 20-22 DNA binding activity 23 , inhibitory effects on β-glucosidase enzymes 23 and plant growth inhibitory activities were also reported. 10,24 This paper describes the isolation of the new potent antifungal and antimalarial dihydroindolizinium chloride prosopilosidine (1) from honey mesquite, together with three new analogs prosopilosine (2), isoprosopilosine (3) and isoprosopilosidine (4), and the known juliprosopine (5). 25,26 P. glandulosa Torrey var. glandulosa, has not previously been subjected to chemical or biological investigations. Prosop...

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Die Konstitution des Alkaloides Juliprosopin aus Prosopisjuliflora A. Dc. 176. Mitteilung über organische Naturstoffe

Cited by 54 publications

References 15 publications

Study of the distribution profile of piperidine alkaloids in various parts of Prosopis juliflora by the application of Direct Analysis in Real Time Mass Spectrometry (DART-MS)

Study of the distribution profile of piperidine alkaloids in various parts of Prosopis juliflora by the application of Direct Analysis in Real Time Mass Spectrometry (DART-MS)

Autophagy protects against neural cell death induced by piperidine alkaloids present in Prosopis juliflora (Mesquite)

Indolizidine, Antiinfective and Antiparasitic Compounds from Prosopis glandulosa Torr. Var. glandulosa

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