Celastraceae family

Maytenus illicifolia Mart, ex Reiss. (Celastraceae family), more commonly known as Cangorosa, is found in South America where it is used for its analgesic, antipyretic, antiseptic, and anticancer properties and for birth control, particularly in Paraguay. 

Members of the Celastraceae family produce a wide variety of macrocyclic sesquiterpene pyridine alkaloids, which will be discussed below. In addition, various nicotinoyl esters of the base sesquiterpene structure p-dihydroagarofuran are produced, such as in the cangorins [160], wilforcidine [161], triptofordinines [162], and related compounds [163]. 

As a general rule, the biosynthesis of skeletons belonging to the Celastraceae family is extremely specific, the triterpene-quinones and P-dihydro-agarofiiran type skeleton sesquiterpenes from these species having a notably high degree of oxidation. The presence of tritetpene-quinones indicates the biosynthetic specificity of the Celastraceae family since these compounds are synthesized in the roots and are virtually exclusive to the family. 

The next few pages are an update on the state of the Celastraceae family in Latin America, detailing the different chemical structures found and the results of the studies of biological activity carried out since the last publication on the subject [1]. 

THE SYSTEMAT1CS OF THE CELASTRACEAE FAMILY AND THE LATIN AMERICAN GENERA... 

The Celastraceae family consists of about 55 genera and 850 species. According to Takhtajan [4], Hippocrateaceae would be subordinate to the Celastraceae. Systematically the Celastraceae family is arranged hierarchically as follows ... 

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). 

M. loesner Urb. and M. buxifolia (A. Rich) Griseb collected on the island of Cuba have been extensively studied by H. Ripperger et al. [46-47] who isolated a series of new macrocyclic alkaloids of the spermidin type, commonly found in the Celastraceae family the new alkaloids could be related to others already obtained by Kupchan s group. 

Plants of the Celastraceae family had been used in folk medicine of various countries [2]. From the species of this family, sesquiterpenes,... 

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]. 

Lupane triterpenes are very common in the Celastraceae family. Esters of lupane triterpenes with aromatic acids have been isolated from others sources but in Celastraceae 0-caffeoyl esters are the most frequently found. C-3 position is the most common compromised with esterification and the stereochemistry of the ester moiety is usually p. 

Ursanes are a triterpene skeleton-type commonly isolated from plants of the Celastraceae family. 

Among the compounds related to triterpene recently isolated from the Celastraceae family cytotoxic cardenolides and a possible Diels-Alder adduct have been reported in the literature by Ankli et al. [59] and our research group [60]. 

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]. 

Trimeric compounds have only been isolated from one species of the Celastraceae family, M. scutioides, by Gonzalez et al. [8]. The two compounds were based on pristimerin units, one in the quinoid form and two in the aromatic form. 

Products isolated from plants of the Celastraceae family have showed insecticidal and antifeedant activities, as discussed earlier. The compounds reported belong to the agarofuran sesquiterpene-type and sesquiterpene pyridine-type alkaloids. Nevertheless, the only description of insecticidal activity of quinone methides found is from Avilla et al [102], Despite the fact that the compounds assayed were known the... 

In the course of these research programmes, many characteristic bioactive compounds have been reported. Polyester sesquiterpenes and pyridine-sesquiterpene alkaloids with insect antifeedant or insecticidal properties have been isolated from some species and recently sesquiterpene pyridine alkaloids with immunosuppressive or antitumoral activities have also been described. Diterpene triepoxides with potent antileukemic and immunosupressive activities and triterpenoid quinonemethides, named as celastroloids , with antibiotic and cytostatic activities, have been isolated from species of the Celastraceae family. 

Many researchers in different parts of the world are actively involved in recording the available information on traditional medicine. To contribute to this vast task we present in this review a compilation of the ethnomedical uses of the species of the Celastraceae family, recorded from the NAPRALERT data base up to September 1997. 

The Celastraceae family took on a new lease of life in the seventies when the maytansinoids, compounds with exceptional antitumoral properties, were discovered [116]. Nonetheless, the maytansinoids have not been made into a useful drug form as they cause serious gastro-intestinal damage when applied to rats [117]. 

The Celastraceae family is a rich source of sesquiterpene esters based on the dihydro-3-agarofuran [5,11-epoxy-5P,10a-eudesm-4(14)-ene] skeleton, and they are considered to be chemotaxonomic indicators of the family [6]. X-ray data and a conformational study by molecular mechanics showed that in every instance with only slight variations, the rraw-fiised A and B rings formed a chair-chair decalin system, slightly distorted by the presence of the 1,3-diaxial bond responsible for the tetrahydrofuran C ring, practically perpendicular to the plain formed by carbons C-5, C-7, C-8 and C-10, Fig. (1). 

The presence of alkaloids in plants of the Celastraceae family has been recognized for more than 50 years [119]. Since the first publication appeared in 1934 on the presence of alkaloids in the plants of this family [147], isolation of alkaloidal components from these plants and their structural studies have been performed by a number of investigators. 

---