Über Juliprosin, ein weiteres Alkaloid aus Prosopis julifloraA.DC. 180. Mitteilung über organische Naturstoffe

Abstract

Juliprosine, a Further Alkaloid Isolated from Prosopis juliforu A.DC SummaryBy catalytic hydrogenation of the second base juliprosine (2) isolated from Prosopis julifora (Leguminosae) the hexahydroderivative 5 was formed. The same product was obtained also by catalytic hydrogenation of juliprosopine

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)

“…1 It is known to contain piperidine alkaloids having medicinal properties. 2 Many alkaloids such as, juliprosopine, julifloricine, julifloridine, juliprosinine, 4 3′-oxojuliprosopine, sceojuliprosopinol, 3-oxojuliprosine and 3′-oxo-juliprosine 5 have been isolated from leaves and there in vitro biological activities demonstrated, which include anti-inflammatory, 2 antibacterial, 6,7 antifungal, 8 hemolytic, 9 allelopathic, 10 cytotoxic 11 and antitumoral. 12 Although the plant is reported to contain pharmacologically active piperidine alkaloids, limited work had been done to study the distribution profile of its metabolite.…”

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

“…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.…”

“…The UV spectrum of 1 demonstrated absorption bands at λ max 198 and 230 nm, typical of indolizinium chromophore. 8 The NMR spectra of 1 revealed a 2,3-dihydro-1H-indolizinium nucleus 8,9 consisting of two trisubstituted and a tetrasubstituted olefin [δ H-5′ 8.64 and δ H-7″″ 8.18, each 1H, s; δ C 137.3, 144.3 (2 × d); δ C 139.1, 141.3, 155.0 (3 × s)], and three methylenes at δ C-1″″ 31.6, δ C-2″″ 20.9 and δ C-3″″ 59.4. In addition, NMR spectra displayed oxymethine, methine adjacent to nitrogen, methylene, and methyl signals, each accounting for 2 carbons and assigned to two piperidinyl rings, as well as ten methylenes for two decanyl moieties.…”

“…1 revealed a 2,3-dihydro-1H-indolizinium nucleus 8,9 consisting of two trisubstituted and a tetrasubstituted olefin [δ H-5′ 8.64 and δ H-7″″ 8.18, each 1H, s; δ C 137.3, 144.3 (2 × d); δ C 139.1, 141.3, 155.0 (3 × s)], and three methylenes at δ C-1″″ 31.6, δ C-2″″ 20.9 and δ C-3″″ 59. 4.…”

“…In addition, NMR spectra displayed oxymethine, methine adjacent to nitrogen, methylene, and methyl signals, each accounting for 2 carbons and assigned to two piperidinyl rings, as well as ten methylenes for two decanyl moieties. Comparison of the NMR spectra of 1 and (2S,3R,6S)-juliprosine (9) 8,12 suggested close similarities for the dihydroindolizidinium ring and attached decanyl residues, but showed notable differences for the piperidinyl rings (δ C 51.5, 68.4, 26.7, 28.2, 49.0, 11.9 and 29.3; C-2/2′-C-7/7′, and C-1″/1‴; vs. δ C 57.2, 67.6, 31.4, 25.6, 55.8, 18.1, and 36.0/36.1 for 9), thereby suggesting that 1 was a diastereoisomer of 9. Strong shielding of 13 C chemical shift values for C-2/2′, C-6/6′, C-7/7′ and C-1″/1‴ of the piperidine ring and attached methylene carbons indicated that the relative configurations of C-2/2′ and C-6/6′ were different (ie.…”