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Title: Antiparasitic and antimicrobial indolizidines from the leaves of Prosopis glandulosa var glandulosa from Nevada and Texas USA

Author
item RAHMAN, AZIZ ABDUR - University Of Mississippi
item SAMOYLENKO, VLADIMIR - University Of Mississippi
item JACOB, MELISSA - University Of Mississippi
item SAHU, RAJNISH - University Of Mississippi
item JAIN, SURENDRA - University Of Mississippi
item KHAN, SHABANA - University Of Mississippi
item TEKWANI, BABU - University Of Mississippi
item MUHAMMAD, ILIAS - University Of Mississippi

Submitted to: Planta Medica
Publication Type: Peer Reviewed Journal
Publication Acceptance Date: 2/16/2011
Publication Date: 3/7/2011
Citation: Rahman, A., Samoylenko, V., Jacob, M.R., Sahu, R., Jain, S.K., Khan, S.I., Tekwani, B.L., Muhammad, I. 2011. Antiparasitic and antimicrobial indolizidines from the leaves of Prosopis glandulosa var glandulosa from Nevada and Texas USA. Planta Medica. doi.org/10.1055/s-0030-127096.

Interpretive Summary: The paper is devoted to the isolation and structure elucidation of a new indolizidine alkaloid together with previously known indolizidine analogs from the leaves of Prosopis glandulosa, collected from Nevada and Texas, USA. The isolated compounds have demonstrated potent antimalarial, antileishmanial and antimicrobial activities. This work also suggests that the qualitative and quantitative nature of the bioactive alkaloidal profile in P. glandulosa varies significantly due to geographical location.

Technical Abstract: A new indolizidine alkaloid, named (Delta) 1,6-juliprosopine (1), together with previously known indolizidine analogs (2-6), was isolated from the leaves of Prosopis glandulosa var. glandulosa, collected from Nevada, USA; while two other known indolizidines juliprosopine (6) and juliprosine (7) were isolated from P. glandulosa leaves collected in Texas, USA. The structures of compound 1 and 7 were determined using a combination of NMR and MS techniques. Compound 7 exhibited potent antimalarial activity against Plasmodium falciparum D6 and W2 strains with IC50 values of 170 and 150 ng/mL, respectively, while 1 was found to be less active (IC50 values 560 and 600 ng/mL). Both the compounds were devoid of VERO cells toxicity up to a concentration of 23800 ng/mL. The antileishmanial activity of indolizidines was evaluated against Leishmania donovani promastigotes, axenic amastigotes and amastigotes in THP1 macrophage cultures. When tested against macrophage cultures, the tertiary bases (1, 3, 6) were found to be more potent than quaternary salts (2, 5, 7), displayed IC50 values between 0.8-1.7 µg/mL and 3.1-6.0 µg/mL, respectively. In addition, compound 7 showed potent antifungal activity against Cryptococcus neoformans and antibacterial activity against Mycobacterium intracellulare, while 1 was potent only against C. neoformans and weakly active against other organisms.