Triterpenes and limonoids of Cedrela: Distribution, biosynthesis, and ¹H and ¹³C NMR data

Abstract

Cedrela genus, a member of the Meliaceae family, presents both chemical characteristics associated with and those that distinguish it from the rest of its members. The presence of triterpenes and limonoids is the characteristic of the Meliaceae family, but the class and type of these chemical constituents are distinctive for each genus. Cedrela includes cycloartane, ursane, oleanane, tirucallane, butyrospermane, and apotirucallane triterpenes, and its limonoids belongs to six class and nine types, known as class Ia-type havanensines, class Ib-type delevoyin, class II-type gedunin, class IIIb-type andirobin, class IIIgtype mexicanolide, class IVa-type evoludone, class Va-type obacunol, class Vtype limonin, and class VIII. Each of these structural arrangements includes specific traits, defined by their biosynthetic origin, which can be established by means of structural elucidation techniques, particularly 1 H and 13 C NMR, which assisted by 2D NMR techniques, allowing to deduce their structures unequivocally. The constant presence of these skeletal arrangements in Cedrela ensures that they are its chemophenetic markers and their recurrence is an important criterion for their identity. This review is a compilation of the occurrence of triterpenes and limonoids in Cedrela genus, detailing their biosynthetic association and collecting and organizing their NMR data, with the purpose of facilitating its location, analysis, and use in the phytochemical study of species from this genus.

Limonoids isolated from Chisocheton ceramicus Miq. and the antiadipogenic mechanism of action of ceramicine B

“…There are different genera within the Meliaceae family offering a large panel of limonoids, such as the genera Aglaia , [ 11 ] Amoora , [ 12 ] Cedrela , [ 13,14 ] Dysoxylum , [ 15 ] Guarea, [ 16 ] Melia , [ 17 ] Swietenia , [ 18 ] and Walsura . [ 19 ] The list includes also the genus Chisocheton , well known for its richness in limonoids.…”

“…[7][8][9] These limonoids can be used as starting materials to guide the design of derivatives and rearranged molecules with antioxidant and/or anti-inflammatory properties. [10] There are different genera within the Meliaceae family offering a large panel of limonoids, such as the genera Aglaia, [11] Amoora, [12] Cedrela, [13,14] Dysoxylum, [15] Guarea, [16] Melia, [17] Swietenia, [18] and Walsura. [19] The list includes also the genus Chisocheton, well known for its richness in limonoids.…”