Carapanolides M–S from seeds of andiroba (Carapa guianensis, Meliaceae) and triglyceride metabolism-promoting activity in high glucose-pretreated HepG2 cells

Five novel phragmalin-type limonoids, carapanolides M–Q (1–5), together with two mexicanolide-type limonoids, carapanolides R–S (6–7), were isolated from the oil of Carapa guianensis AUBLET (Meliaceae) seeds, a traditional medicine in Brazil and Latin American countries. Their structures were elucidated on the basis of spectroscopic analyses using 1D and 2D NMR techniques and a single-crystal X-ray diffraction analysis. Compounds 1–7 along with 12 known limonoids, 8–19, isolated from the flower and seed oil of C. guianensis were assayed to determine their triglyceride metabolism-promoting activities in the high glucose-pretreated human hepatocellular carcinoma cell line, HepG2. Gedunin-type limonoid: 14 (% of control at 10 μM: 35.4±3.9), 13 (55.0±3.6 at 10 μM), and 18 (75.4±4.2 at 10 μM) significantly reduced TG levels in hepatocytes.

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