Carapanosins D—F from the Seeds of Andiroba (Carapa guianensis, Meliaceae) and Their Effects on LPS-Activated NO Production

Abstract

A novel nor-phragmalin-type limonoid, named carapanosin D (1), and two novel mexicanolide-type limonoids, carapanosins E (2) and F (3), were isolated from the seed oil of andiroba (Carapa guianensis Aublet), a traditional medicine in Brazil and Latin American countries. Their structures were unambiguously determined on the basis of spectroscopic analyses using one-dimensional (1D) and two-dimensional (2D) NMR techniques and High resolution Fast Atom Bombardment Mass Spectrometry (HRFABMS). Compounds 1–3 were evaluated for their effects on the production of nitric oxide (NO) in Lipopolysaccharide (LPS)-activated mouse peritoneal macrophages. The NO inhibitory assay suggested that compounds 2 and 3 have high potency as inhibitors of macrophage activation.

Chemistry and Biology of Novel Meliaceae Limonoids

“…Compounds (833, 774, 549) showed strong inhibitory activities against human carboxylesterase2 (hCES2) with IC 50 values of 6.63, 11.35 and 5.05 μM, respectively 153 . Compounds (261,262,202,195,158) exhibited neuroprotective effects against 6-OHDA-induced cell death in human neuroblastoma SH-SY5Y cells, showing EC 50 values of 0.27, 0.89, 3.08, 7.16 and 3.42 μM, respectively as compared to positive control curcumin with EC 50 value of 6.08 μM 142 366 . The autophagic activity of compound (499) was evaluated on a U-87 MG glioblastoma cell line which showed a weak cytotoxic effect and severe cell proliferation inhibition at 80 µM 173 .…”

“…Nineteen Meliaceae limonoids belonging to this class were reported earlier 12 . They differ in substitution at C4, where there is an aldehyde group in compound (330) and ester group in compound (331). Evodulone This class of limonoid is identified by the presence of an A ring in the form of a seven membered lactone ring and oxygen at C7.…”

Chemistry and Biology of Novel Meliaceae Limonoids

“…Nineteen Meliaceae limonoids belonging to this class were reported earlier 12 . They differ in substitution at C4, where there is an aldehyde group in compound (330) and ester group in compound (331). Evodulone This class of limonoid is identified by the presence of an A ring in the form of a seven membered lactone ring and oxygen at C7.…”

“…Limonoid Substituent Source Carapansin C R = H Carapa guianensis 262 Andirolide A R = OAc Carapa guianensis 263…”

Predictive calculation of structural, nonlinear optical, electronic and thermodynamic properties of andirobin molecule from ab initio and DFT methods

“…1) of molecular formula C 27 H 32 O 7 and a molar mass of 468,54 g/ mol. It is a molecule with anti-inflammatory and analgesic properties, as well as anti-plasmodial activity [2,3]. The crystal structure of andirobin [4] with the labelling of the atoms is shown in Fig.…”