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.
Highlights
Meliaceae plants are a well-known source of structurally diverse limonoids with a wide range of bioactivities, such as antimalarial and antifeedant
Our series of studies on the components of the seed oil of C. guianensis revealed the structures of carapanolides A and B [8], guianolide A and B [9], carapanolides C–I [10], carapanolides J–L [11], carapanolides M–S [12], carapanolides T–X [13], and carapanosins A–C [14] in the seed oil of andiroba
We reported the absolute structure of guianolactones A and B from the seed oil of C. guianasis (Meliaceae) [15]
Summary
Meliaceae plants are a well-known source of structurally diverse limonoids with a wide range of bioactivities, such as antimalarial and antifeedant. Limonoids in the plant kingdom occur mainly in the Meliaceae, Rutaceae, and Simaroubaceae families [1]. Andiroba is one of the Meliaceae plants in the rain forests of South America, and its woody four-cornered nut has four cells, each of which contains two to three seeds with oil-rich kernels. We reported the absolute structure of guianolactones A and B from the seed oil of C. guianasis (Meliaceae) [15]. Our recent study of the seed oil of C. guianasis revealed the structures of an unusual. We describe the isolation and structural determination of three new limonoids and the effects of 1–3 on the production of nitric oxide (NO) in Lipopolysaccharide.
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