Terpenoids from Maytenus Species and Assessment of Their Reversal Activity against a Multidrug‐Resistant Leishmania tropica Line

Abstract

The phytochemical analysis of the root bark extracts of the Chilean Maytenus, M. chubutensis, and M. magellanica (Celastraceae), led to the isolation of one phenolic nortriterpene, 1, and one diterpene with a nor-ent-kaurene skeleton, 2. In addition, four known compounds were isolated, among which compound 3 has been isolated for the first time from a natural source. Their structures were elucidated by spectroscopic methods, including 1D- and 2D-NMR (COSY, ROESY, HSQC, and HMBC) experiments, comparison with data reported in the literature, and chemical correlations. The isolated compounds were assayed for their reversal activity against a multidrug-resistant Leishmania tropica line, overexpressing a P-glycoprotein related transporter. Compound 1 showed moderate multidrug-resistance reversal activity.

Microbiological evaluation of isolated compounds from the bark of Maytenus guianensis Klotzsch ex Reissek (Celastraceae)

“…Furthermore, the family has species with great therapeutical relevance, presenting various pharmacological activities, such as: antiulcerogenic, insecticidal, immunosuppressive, anti-rheumatic, antibacterial and anticancer (FONSECA et al, 2007), and given that, species of this family have been object of many phytochemical investigations and secondary metabolites isolated of these species have shown great biological activity (FONSECA et al, 2007;ALMEIDA et al, 2010;DING et al, 2010;LIMA et al, 2010;ANTONISAMY et al, 2011;KENNEDY et al, 2011;SANTOS et al, 2013), of which we can cite the friedelane pentacyclic triterpenes, quinonamethides, sesquiterpenes, secofriedelanes, steroids, agarofuranic derivatives, proanthocyanidin glycosides, flavonoids, sesquiterpene pyridine alkaloids and catequines (SILVA et al, 2008;SOUSA et al, 2012;HURTADO, 2013).…”

The Potential of Traditional Knowledge to Develop Effective Medicines for the Treatment of Leishmaniasis

“…It has been demonstrated that different species have leishmanicidal activity, and such activity can be mainly related to terpenes and sesquiterpenes synthesized by this genus ( Alvarenga et al, 2008 ). Although only in vitro studies have been carried out so far, the most important finding is related to the potential of molecules against multidrug resistant parasites ( Pérez-Victoria et al, 1999 ; Kennedy et al, 2001 , 2011 ). The plant Juniperus excelsa M. Bieb (Cupressaceae) was cited only once by traditional communities, and few studies have been conducted on this species.…”

A Review on Phytochemicals of the Genus Maytenus and Their Bioactive Studies

“…Three compounds 6-oxo-iguesterol (23), 6-oxo-tingenol (24) and 3-O-methoxy-6-oxo-tingenol (25) have been obtained from the root bark of M. canariensis [12]. Four new triterpenes blepharotriol (26), 6-deoxoblepharodol (27), isoblepharodol (28) and 7-oxo-blepharodol (29) were separated from M. blepharodes [23].…”

“…Six new compounds, including 7-oxo-7, 8-dihydro-scutione (34), 6,23-dioxo-7,8-dihydropristimerol-23-oic Acid (35), 23-nor-blepharodol (36), 3-methoxy-6-oxo-tingenol-23-oic Acid (37), retusonine (38) and were isolated from the root bark of M. retusa [25]. A new compound 3-O-Methyl-6-oxo-pristimerol (40) has been isolated from the hexane/Et 2 O 1:1 extract of the root bark of M. chubutensis [26]. Compounds 3β,24-epoxy-2α,3α-dihydroxy-D:A-friedooleanan-29-oic acid methyl ester (41), 2α-acetoxy-3β,24-epoxy-3α-hydroxy-D:A-friedooleanan-29-oic acid methyl ester (42), 3α-hydroxy-D:Afriedooleanan-28-oic acid (43) and 3-oxo-D:A-friedooleanan-28,30-olide (44) were obtained from the root bark of M. jelskii [27].…”