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

Prosopis glandulosa Torr. var. torreyana (L. Benson) M. C. Johnston root bark, collected in Texas, yielded two new alkylated piperidine alkaloids, namely 3-isocassine (1) and N-methyl-3-isocassine (2), together with the previously reported N-methylcassine (3). In addition, the alkylated piperidinyl indolizidine alkaloid juliprosopine (4) was isolated from the leaves of the same plant. The structures and stereochemistry of compounds 1–4 were determined from 1D and 2D NMR data, including COSY, HMQC, HMBC and NOESY experiments, and ESI-HRMS. Juliprosopine (4) demonstrated antimicrobial activities against a panel of microorganisms, including potent antifungal activities against Aspergillus fumigatus.

[1]  Qui Khuong-Huu,et al.  Alcaloïdes Pipéridiniques II. Structures de la Prosopine et de la Prosopinine, Alcaloïdes du Prosopis Africana (Guill. et Perr.) Taub. [1] , 2010 .

[2]  D. Austin.  Healing with Plants in the American and Mexican West , 1997, Economic Botany.

[3]  Zaheer-ul-Haq,et al.  Juliflorine: a potent natural peripheral anionic-site-binding inhibitor of acetylcholinesterase with calcium-channel blocking potential, a leading candidate for Alzheimer's disease therapy. , 2005, Biochemical and biophysical research communications.

[4]  H. Makabe,et al.  Total synthesis of (-)-cassine. , 2003, Organic letters.

[5]  Robert H. Gilman,et al.  Rapid, Low-Technology MIC Determination with Clinical Mycobacterium tuberculosis Isolates by Using the Microplate Alamar Blue Assay , 1998, Journal of Clinical Microbiology.

[6]  A. Pahl,et al.  Total synthesis of the piperidinol alkaloid (−)-(2R,3R,6S)-cassine , 1997 .

[7]  Aqeel Ahmad,et al.  STUDY ON THE ANTIFUNGAL EFFICACY OF JULIFLORINE AND A BENZENE-INSOLUBLE ALKALOIDAL FRACTION OF PROSOPIS JULIFLORA , 1997 .

[8]  M. Hesse,et al.  ORGANIC NATURAL SUBSTANCES. 180. JULIPROSINE, A FURTHER ALKALOID ISOLATED FROM PROSOPIS JULIFLORA A. DC , 1982 .

[9]  M. Hesse,et al.  Über Juliprosin, ein weiteres Alkaloid aus Prosopis julifloraA.DC. 180. Mitteilung über organische Naturstoffe† , 1981 .

[10]  M. Hesse,et al.  Die Konstitution des Alkaloides Juliprosopin aus Prosopisjuliflora A. Dc. 176. Mitteilung über organische Naturstoffe , 1980 .

[11]  J. Cabrera,et al.  Isolation of N-Methylcassine From Species of the Genus Prosopis , 1980 .

[12]  V. Ahmad,et al.  New Alkaloids from Prosopis juliflora DC , 1978 .

[13]  A. Burkart.  A Monograph of the Genus Prosopis (Leguminosae Subfam. Mimosoideae) , 1976, Journal of the Arnold Arboretum.

[14]  R. Highet.  Alkaloids of Cassia Species. I. Cassine1 , 1964 .