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Molecules. 2017 Mar 24;22(4). pii: E519. doi: 10.3390/molecules22040519.

(R)-(-)-Aloesaponol III 8-Methyl Ether from Eremurus persicus: A Novel Compound against Leishmaniosis.

Author information

1
Department of Drug Sciences, Medicinal Chemistry and Pharmaceutical Technology Section, University of Pavia, Viale Taramelli 12, 27100 Pavia, Italy. daniela.rossi@unipv.it.
2
Department of Drug Sciences, Medicinal Chemistry and Pharmaceutical Technology Section, University of Pavia, Viale Taramelli 12, 27100 Pavia, Italy. karzchem@yahoo.com.
3
Department of Science-Chemistry, University of Garmian, Kalar 46021, Kurdistan Region, Iraq. karzchem@yahoo.com.
4
Department of Drug Sciences, Medicinal Chemistry and Pharmaceutical Technology Section, University of Pavia, Viale Taramelli 12, 27100 Pavia, Italy. raffaella.gaggeri@irst.emr.it.
5
Istituto Scientifico Romagnolo per lo Studio e la Cura dei Tumori (IRST) Srl-IRCCS Via Piero Maroncelli, 40, 47014 Meldola (FC), Italy. raffaella.gaggeri@irst.emr.it.
6
Department of Drug Sciences, Medicinal Chemistry and Pharmaceutical Technology Section, University of Pavia, Viale Taramelli 12, 27100 Pavia, Italy. serena.dellavolpe01@universitadipavia.it.
7
Department of Drug Sciences, Medicinal Chemistry and Pharmaceutical Technology Section, University of Pavia, Viale Taramelli 12, 27100 Pavia, Italy. lauretta.maggi@unipv.it.
8
Dipartimento di Medicina Molecolare e Traslazionale, Università di Brescia, Viale Europa 11, 25123 Brescia, Italy. giuseppe.mazzeo@unibs.it.
9
Dipartimento di Medicina Molecolare e Traslazionale, Università di Brescia, Viale Europa 11, 25123 Brescia, Italy. giovanna.longhi@unibs.it.
10
Dipartimento di Medicina Molecolare e Traslazionale, Università di Brescia, Viale Europa 11, 25123 Brescia, Italy. smrmachado@gmail.com.
11
Centro Grandi Strumenti, University of Pavia, Via Bassi 21, 27100 Pavia, Italy. federica.corana@unipv.it.
12
Department of Earth and Environmental Sciences, University of Pavia, Via S. Epifanio 14, 27100 Pavia, Italy. emanuela.martino@unipv.it.
13
CESPU, Instituto de Investigação e Formação Avançada em Ciências e Tecnologias da Saúde, 4585-116 Gandra PRD, Portugal. smrmachado@gmail.com.
14
CIBIO-UP, Centro de Investigação em Biodiversidade e Recursos Genéticos, Universidade do Porto, InBIO, 4485-661 Vairão, Portugal. smrmachado@gmail.com.
15
Faculty of Pharmacy, University of Coimbra, Pólo das Ciências da Saúde, Azinhaga de Santa Comba, 3000-548 Coimbra, Portugal. raquel.varandas@ci.uc.pt.
16
CNC-Center for Neurosciences and Cell Biology, University of Coimbra, Rua Larga Faculty of Medicine, Pólo I, 3004-504 Coimbra, Portugal. raquel.varandas@ci.uc.pt.
17
Faculty of Pharmacy, University of Coimbra, Pólo das Ciências da Saúde, Azinhaga de Santa Comba, 3000-548 Coimbra, Portugal. mcsousa@ci.uc.pt.
18
CNC-Center for Neurosciences and Cell Biology, University of Coimbra, Rua Larga Faculty of Medicine, Pólo I, 3004-504 Coimbra, Portugal. mcsousa@ci.uc.pt.
19
Department of Drug Sciences, Medicinal Chemistry and Pharmaceutical Technology Section, University of Pavia, Viale Taramelli 12, 27100 Pavia, Italy. simona.collina@unipv.it.

Abstract

Leishmaniosis is a neglected tropical disease which affects several millions of people worldwide. The current drug therapies are expensive and often lack efficacy, mainly due to the development of parasite resistance. Hence, there is an urgent need for new drugs effective against Leishmania infections. As a part of our ongoing study on the phytochemical characterization and biological investigation of plants used in the traditional medicine of western and central Asia, in the present study, we focused on Eremurus persicus root extract in order to evaluate its potential in the treatment of leishmaniosis. As a result of our study, aloesaponol III 8-methyl ether (ASME) was isolated for the first time from Eremurus persicus root extract, its chemical structure elucidated by means of IR and NMR experiments and the (R) configuration assigned by optical activity measurements: chiroptical aspects were investigated with vibrational circular dichroism (VCD) and electronic circular dichroism (ECD) spectroscopies and DFT (density functional theory) quantum mechanical calculations. Concerning biological investigations, our results clearly proved that (R)-ASME inhibits Leishmania infantum promastigotes viability (IC50 73 µg/mL), inducing morphological alterations and mitochondrial potential deregulation. Moreover, it is not toxic on macrophages at the concentration tested, thus representing a promising molecule against Leishmania infections.

KEYWORDS:

(R)-aloesaponol III-8 methyl ether; Eremurus persicus; drug identification; leishmaniosis; plant extract

PMID:
28338625
PMCID:
PMC6154379
DOI:
10.3390/molecules22040519
[Indexed for MEDLINE]
Free PMC Article

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