Isolation and chemical characterization of components from Azadirachta indica and Melia azedarach with biological activity

PIERLUIGI CABONI; NIKOLETTA G. NTALLI; CARLOS A. BUENO; LAURA E. ALCHÉ

Emerging Trends in Dietary Components for Preventing and Combating Disease

ACS Books

Año: 2012; p. 51 - 77

In this chapter we review the biological activities of Azadirachtaindica A. Juss (neem) (AI) and Melia azedarach L. (chinaberry)(MA), as well as the principle components this activity has beenattributed to. We develop analytical methods for the structureelucidation and quantitation of the most abundant limonoids of AIand MA seeds and we report on their biological properties. Thelimonoids afforded by AI were azadirachtin A and B, nimbin,salannin and their acetyl derivatives; while MA afforded a newtriterpenoid, named 3-
-tigloylmelianone, as well as three knownlimonoids named methyl kulonate, 21--acetoxymelianone andmelianone. The structures elucidation of the limonoids wasperformed by means of 1D and 2D-NMR and the accuracy oftheoretical exact mass values, was deduced by the employment ofHPLC-Q-TOF analysis. According to our results 21--acetoxymelianone and 3-
-tigloylmelianone gather bothantiproliferative (IC50 = 100 and 91.8 μg/ml) and cytotoxic (CC50 =90.6 and 64.7 μg/ml) activities against the tumorigenic cell lineA549, while melianone exhibited the highest cytotoxic activitywith an CC50 calculated at 3.6 μg/ml. Methyl kulonate as well aslimonoids isolated from AI were not found neither cytotoxic norantiproliferative. In extends, MA fruits? methanol extract wasanalysed by GC/MS and was found to contain hexadecanoic,acetic, and hexanoic acids as well as furfural, 5-hydroxymethylfurfural. This extract was found nematicidal againstMeloidogyne incognita, both in terms of juveniles paralysis(EC50/96h = 0.04 %) and biological cycle arrest (EC50 = 0.91 %), andthe activity has been attributed to its contents in organic acids andaldehydes rather than its limonoids contents. A linear relationshipof organic acids? C atom number and nematicidal activity wasestablished at 31.2-500 μg/mL. Furfural exhibited the highestnematicidal activity both after nematodes immersion in testsolutions and after exposure to its vapours (EC 50/1 day = 8.5 and24.1 μg/mL, respectively).