Maytenus species

Avilla, J. Teixido, A. Velasquez, C. Alvarenga, N. Ferro, E. Canela, R. Insecticidal activity of Maytenus species (Celastraceae) nortriterpene quinone methide against codling moth, Cydia pomonella (L.) (Lepidoptera Tortricidae). J. Agric. Food Chem. 2000, 48, 88-92. 

This triterpene skeleton-type is not very common in Celastraceae. Not many examples were found in the literature covered by this review, and most of them were reported for a Maytenus species. 

From two Maytenus species collected in Paraguay, two new pristimerin-related compounds were isolated, 15-a-hydroxypristimerin (57), from M. scutioides [72], and 15-a-hydroxy-21-keto-pristimerin (58) from M. catingarum [73], the last one isolated in our laboratory. The structure of compound (57) was elucidated by spectroscopic means, including MS, h and 13C - NMR, and H - 13C heteronuclear... 

Compounds (57) and (58), isolated from Maytenus species [72,73], were tested against several Gram-positive and Gram-negative bacteria and the yeast Candida albicans. Both compounds were more active than pristimerin (53) and, in the case of (57), than cephotaxime against certain strains. Those data support the hypothesis of Gonzalez [101] that the... 

A very high antitumor activity was earlier found in some extracts of African Maytenus species (M ovata Loes, M. buchananii). This promoted a thorough investigation for the active principle, maytansine, which was shown to be present in minute amounts [116]. This product is structurally related to ansamycins and it is uncommon for a secondary plant metabolite to be related to metabolites from fungi. 

Isolation and Structure Proof. The maytansinoids were (lie first ansamacrolides to be found in plants. The term maytansinoids refers to those ansamacrolides related to maytansinc, whereas the term maytansides refers to maytansinoids lacking the ester side chain at C-3 as well as the corresponding elimination products. Maytansine was first isolated from the alcoholic extract of Maytenus ovatus Loes. Several other maytansinoids and maytansides have been isolated from this species. The structure of niaytan-sine was established by x-ray crystallographic analysis, and the structures of the other maytansinoids and maytansides were arrived at by comparative nmr studies using maytansine. The absolute configuration of maytansine is 3(5), 4(5), 5(5), 6(R), 7(5), 10(5), and 2 (5). 

An important consideration in the agricultural production of plants containing medicinally active components is that they are sometimes produced by, or in consequence of, microbial agents present in or on the plant. These also constitute part of the biodiversity regulated by law, may be pathogenic to other economic crops and are not always easily cultured. Production in the natural habitat raises no problems. As an example one may notice that the maytansinoids, ansa-macrolides, which form part of the chemical make-up of Maytenus ilicifolia and M. aquifolia, Celastraceae, the two species most highly considered for stomach ulcer treatment, have been shown to be produced by bacteria associated with the plants. ... 

The root extracts of Maytenus senegalensis have been shown to inhibit protein kinase C, as well as having lethality against brine shrimp. The dihydroagarofuran sesquiterpene alkaloids mayteine, putterine A and putterine B have been isolated from the root extracts. Quinonemethide triterpenoids, which have revealed potential anti-tumour and antimicrobial activities, are another diverse group of secondary metabolites from the related species Maytenus ilicifolia. ... 

In the course of these research programmes, cytotoxic quinones, polyester sesquiterpenes and pyridine-sesquiterpene alkaloids with antifeedant and/or insecticidal properties have been isolated from Latin American species, in particular those of the Maytenus genus which is extensively used by rural communities and tribes in the Andes and the Amazon basin. Recently some sesquiterpene alkaloids with immunosuppressive activity and sesquiterpenes with antitumoral activity have also been described [3]. 

The Celastraceae family is probably related phylogenetically with the Aquifoliaceae the presence of glandular discs around the ovary and the bright coloured aril in the Celastraceae are the principal differences between the two families. The Celastraceae family is pantropically distributed with radiation towards temperate or temperate-cold climates. In other words, the Celastraceae are principally concentrated in the tropical and subtropical regions and to a lesser extent in the temperate zones of the world (Figure la). The family is better represented in Central America and the West Indies than m South America except for the Maytenus genus [5] (15 species in Peru and 15 in Venezuela). 

The Celastraceae genera are very diversified some of the taxa with most species are Maytenus (225 tropical), Salacia (200 tropical), Euonomynus (176 Himalayas, China and Japan), Hippocratea (120 tropical, South America, Mexico and the South of the USA), Cassine (40 South Africa, Madagascar, tropical Asia and the Pacific), Celastrus (30 principally Asia, some in Australia and in tropical and temperate zones of America), Elaodendrum (16 tropical and subtropical), Pachystima (5 North America) and Gyminda (3 Central America, Mexico and Florida). 

Wilfordin, tryptofordin and celangulin (Fig. 14) are antifeedant compounds obtained from extracts of the Celastraceae species Maytenus rigida [78], Trypterigium wilfordii [79] and Celastrus angulatus [77, 80], respectively, and as some products isolated from South American species have similar structural characteristics, they too have been assayed. 

Anti-inflammatory and antipyretic properties have recently been ascribed to global and purified methanol extracts obtained from the aerial part of Maytenus boaria (Mol.), a quite widespread tree species in the rural areas of Chile and Argentina. 

The Celastraceae family, named commonly as the bittersweet family, consists of 50-55 genera with 800-850 species with pantropical distribution. Nevertheless, a fair number of species are found in temperate regions. The largest genera are Maytenus (225 species), Euonymus (200 species), Cassine (40 species), and Celastrus (30 species) [12, 13]. 

Dimers are a class of compounds isolated from only seven species of Celastraceae family [8,88]. These triterpene dimers were found to be composed of one quinoid type and one aromatic type of triterpene derived from pristimerin, tingenone and / or their congeners joined together by two ether linkages formed between the two A rings or between the A and B rings. From the methylene chloride soluble portion of a methanolic extract of Maytenus chuchuhuasca, four dimeric compounds were isolated by Shirota et al. [88]. 

The leaves of this species have also been of interest in tests for radioprotection in a comparative study with the increase in phagocitosis of the reticular endothelial system [113]. More recently, May terms species have attracted a certain interest because of the particular properties, such as antitumoral and contraceptive ones of the extracts. For example, antitumor activity of a number of phenoldienone triterpenes isolated from Maytenus sp. has been shown [114] and it was demonstrated that they inhibit the synthesis of proteins and of uridine incorporation into DNA [115]. 

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