ABSTRACT
Cedrela odorata (Meliaceae) is a native timber tree to Tropical America, known for its high-quality wood, unfortunately, plantations of this species are severely attacked by Hypsipyla grandella. The attraction or repellency of this pest is related to secondary metabolites such as phenols and limonoids (triterpenes); therefore, it is important to study these compounds to understand the phytochemical phenomena behind this problem. With this aim, the concentration of total phenols and limonoides was evaluated in C. odorata leaves from a plantation established in Tezonapa Veracruz, Mexico. For this, a total of 66 tree leaves samples, from seven sites, were analyzed. Phenols and limonoids concentration showed significant differences not only among different provenances, but also among individual trees of the same site (Tukey, p≤0.05). Phenols concentration was variable and in the range from 49 to 223mg EAG/g e for total phenols, from 7 to 158mg EC/g e for flavonoids and from 4 to 104mg EC/g e for proanthocyanidins. Limonoids concentration was also variable, ranging between 227 and 748mg EL/g e. A major compound was found by High-Performance Liquid Chromatography with Ultraviolet Diode Array Detection (HPLC-UV-DAD), which corresponded to a flavonol kaempferol glycoside derivative; additionally, a flavanol catechin was also detected at low concentrations. GC-MS allowed the identification of the sesquiterpenoids β-elemene, E-caryophyllene, aromadendrene, α-humulene, γ-cadinene, D-germacrene, bicyclogermacrene, and the poly terpenoids D-α-tocopherol and β-sitosterol. Our results suggest that the evaluation of phenols may play an important role as a selection parameter for improvement and conservation programs, if they are complemented with conventional breeding practices.
Cedrela odorata (Meliaceae) es una especie forestal maderable nativa de América Tropical, conocida por la alta calidad de su madera. Plantaciones de esta especie son atacadas severamente por Hypsipyla grandella; la atracción o repelencia de la plaga está relacionada con metabolitos secundarios tipo fenoles y limonoides (triterpenos), por lo que el estudio de estos compuestos es importante para comprender algunos fenómenos fitoquímicos. Se evaluó la concentración de fenoles totales y limonoides en hojas de C. odorata (Meliaceae) de una plantación establecida en Tezonapa Veracruz México, se analizaron 66 individuos de siete procedencias. La concentración de fenoles y limonoides mostró diferencias significativas, no solo entre las procedencias sino también entre los árboles de una determinada procedencia (Tukey, p≤0.05). La concentración de fenoles totales varió de 49 a 223mg EAG/g e, los flavonoides de 7 a 158mg EC/g e y las proantocianidinas de 4 a 104mg EC/g e, mientras que en limonoides se obtuvieron valores de 227 a 748mg EL/g e. Mediante Cromatografía Líquida de Alta Resolución con detector UV-Arreglo de Diodos (HPLC-UV-DAD) se encontró un compuesto mayoritario que corresponde a un flavonol de tipo glicósido de Kaempferol y se identificó el flavanol catequina a bajas concentraciones. Por medio de Cromatografía de Gases-Espectrometría de Masas (CG-MS) se identificaron los sesquiterpenos β-elemeno, E-cariofileno, aromadendreno, humuleno, gama-cadineno, D-germacreno, biciclogermacreno y los poli terpenos Di-α-Tocoferol y β-sitosterol. Nuestros resultados sugieren que la evaluación de los fenoles puede desempeñar un papel importante como parámetro de selección en programas de mejora y conservación, si se complementan con las prácticas convencionales de mejoramiento genético.
Subject(s)
Phenols/analysis , Flavonoids/analysis , Chromatography, High Pressure Liquid , Meliaceae , Cedrela , Limonins/analysis , Flavonols/analysis , Glycosides/analysis , Plant Leaves , MexicoABSTRACT
BACKGROUND: Limonoids are highly oxygenated compounds with a prototypical structure. Their occurrence in the plant kingdom is mainly confined to plant families of Meliaceae and Rutaceae. Owing to their wide range of pharmacological and therapeutic properties, this study was aimed at investigating the potential nitric oxide (NO) and acetylcholinesterase (AChE) inhibitory activity and the cytotoxicity of three limonoids: trichilia lactone D5 (1), rohituka 3 (2) and dregeanin DM4 (3), isolated from Trichilia welwitschii C.DC. RESULTS: Results indicated that the three limonoids had low cytotoxicity towards Vero cells with LC50 values ranging from 89.17 to 75.82 µg/mL. Compounds (2) and (3) had lower cytotoxicity compared to puromycin and doxorubicin used as reference cytotoxic compounds. Compound (1) (LC50 of 23.55 µg/mL) had good antiproliferative activity against RAW 264.7 cancer cells. At the lowest concentration tested (0.5 µg/mL), compound (2) and (3) released the lowest amount of nitric oxide (2.97 and 2.93 µM, respectively). The three limonoids had anti-AChE activity with IC50 values ranged of 19.13 µg/mL for (1), 34.15 µg/mL for (2) and 45.66 µg/mL for (3), compared to galantamine (IC50 of 8.22 µg/mL) used as positive control. CONCLUSION: The limonoid compounds studied in this work inhibited nitric oxide production in LPS-stimulated macrophages and had anti-AChE activity. Trichilia lactone D5 had potential antiproliferative activity against RAW 264.7 cancer cells. The limonoids had low cytotoxicity towards Vero cells lines. This study provided further examples of the importance of limonoids compounds as potential AChE inhibitors and anti-inflammatory agents targeting the inhibition of NO production.