Pentacyclic triterpenes from Cecropia telenitida with immunomodulatory activity on dendritic cells

Abstract

Pentacyclic triterpene Natural product Cytokine modulation Anti-inflammatory activity Dendritic cells Pentacyclic triterpenes are a large family of plant metabolites that exhibit a wide array of biological activities. The genus Cecropia,which encompasses many plant species, has been used as traditional medicine for the treatment of inflammatory diseases and is known to produce many active pentacyclic triterpenes. In this study we investigated the chemical composition of a pentacyclic triterpene fraction from the roots of Cecropia telenitida Cuatrec., Urticaceae. A novel compound, which we termed yarumic acid, and four known molecules (serjanic acid, spergulagenic acid A, 20-hydroxy-ursolic acid and goreishic acid I) were isolated and characterised. In a dendritic cell (DC)based assay, we demonstrated that non-toxic doses of these pentacyclic triterpenes inhibited the secretion of at least one of the proinflammatory cytokines tested (IL-1β, IL-12p40, IL-12p70, TNF-α). Spergulagenic acid A also inhibited nitric oxide production in lipopolysaccharide-stimulated dendritic cell. Serjanic acid and spergulagenic acid A, which were the most potent abundant compounds in the pentacyclic triterpene fraction, showed the most activity in the dendritic cell-based assay. These results show that all pentacyclic triterpenes might contribute to the anti-inflammatory activities of C. telenitida. Moreover, yarumic acid as well as the four known pentacyclic triterpenes, can be exploited as potential immunomodulatory/anti-inflammatory agents

Zebiriosides A-L, oleanane saponins from the roots of Dendrobangia boliviana

“…The 3b configuration of the hydroxyl group was confirmed by the ROESY experiment in which correlations were observed between H-3a, H-5a, and H-23a. These data are consistent with serjanic acid or 3b-hydroxy-30-methylcarboxylate oleane-12-ene-28-oic acid (Montoya Pelaez et al, 2013). The deshielded nature of C-3 (d C 91.2) suggested a monodesmosidic saponin with an osidic chain at this position.…”

Pentacyclic Triterpenes from Cecropia telenitida Can Function as Inhibitors of 11β-Hydroxysteroid Dehydrogenase Type 1

“…The chemical structure derived from these data is illustrated in Figure 4 A. This molecule is closely related to yarumic acid, which was previously isolated and characterized from the same plant source [ 21 ]. To the best of our knowledge, however, this is the first report of this new molecular entity, which we named isoyarumic acid.…”

“…Previous studies indicated that the roots of C. telenitida contained the greatest concentration of PT molecules [ 21 ]. Therefore, 5 kg of dried roots were collected and processed in a solid-liquid semi-pilot plant to extract molecules according to their polarity.…”

“…The capability of triterpene molecules from natural sources to inhibit the enzyme, 11β-HSD1, has been previously reported [ 14 , 32 , 33 ]. Triterpenoid molecules are chemotaxonomic markers of Cecropia plants [ 21 , 34 ]. Due to the chemical properties of these molecules, fraction DE16, which eluted in a mixture of solvents of moderate polarity (Dichloromethane/Ethyl acetate), was expected to be enriched in this class of molecules.…”

“…The first reported chemical analysis of the Colombia endemic plant Cecropia telenitida revealed a new PT known as yarumic acid and four previously identified PT molecules [ 21 ]. In that study, a dendritic cell model was used to test the anti-inflammatory properties of the identified PTs.…”