Simaroubaceae family

A literature search conducted for the terms quassinoid and simaroubolide (a term used in the 1970s to designate these molecules isolated from plants of the Simaroubaceae family) on the search engines Scopus and Science Direct provided a total of 453 references from 1970 to 2011 Fig. 125.7 illustrates the yearly profile. 

Species belonging to the Simaroubaceae family are widely referenced in the pharmacopoeias of different medical systems around the world, whether they be of contemporary or ancient use, transmitted orally, or from written sources. For example, Ailanthus altissima, the area of natural distribution of which extends from Manchuria to Malaysia, is one of the most cited species in ancient Chinese medical treatise for a wide range of indications. One of the oldest recipes for this species has been recorded in a book in China dating back to 732 AD for the treatment of mental illness [110]. Its bark is stiU registered in actual Chinese and Asian pharmacopoeias, and it is traded across China. The same applies to Brucea javanica fruits in Southeast Asia and to Ailanthus excelsa Roxb. bark, mentioned in ancient and contemporary ayurvedic medicine books [111]. The use of Brucea antidysenterica bark has also been documented since the sixteenth century in ancient Arabic medical pharmacopoeias [112]. 

These types of alkaloids are not of monoterpenoid origin. Plants of the Simaroubaceae family are trees that grow mainly in tropical and, to some extent, subtropical countries. Picrasma quassioides is a Japanese deciduous tree its heartwood contains quassin, tannin, and nigakinone, and is used as a bitter... 

More than ten years have elapsed since the publication of a comprehensive review on the quassinoids, the bitter principles of the Simaroubaceae family (80). Interest in these terpenoids has increased enormously in recent years due in part to the finding of the American National Cancer Institute in the early 1970s that these compounds display marked antileukemic activity. Furthermore, a wide spectrum of other biological properties for the quassinoids has been discovered and studies on chemical modifications of inactive members to yield biologically active ones were undertaken. New structures have been established also and numerous synthetic approaches have been developed which include the total synthesis of the parent compound, quassin (p. 250) and also that of castelanolide (p. 253). 

Todtkilia, Vepris and Zanthaxyhm species of the Rutaceae mily, and Samadera bidwillii of the Simaroubaceae family. 

Methoxycanthin-6-one (15) has been isolated from the bark of both the stem and root of Charpentiera obovata (Amaranthaceae) (32) and the aerial parts of Drymaria cordata (Caryophyllaceae) (33). This is one of the compounds not found in the families Rutaceae and Simaroubaceae. Its UV and IR spectra proved that it was a canthin-6-one alkaloid, and the H-NMR spectrum confirmed the methoxyl funclion. As natural 15 was identical with an authentic compound synthesized by Nelson and Price (31), structure 15 was determined. 

Crude extracts of the root bark from Celastrus paniculatus Willd. (Celastraceae) demonstrated significant activity against cultured P. falciparum (93), and the active principle was shown to be pristimerin, a quinonoid triterpene. The family Simaroubaceae has also yielded a number of compounds with in vivo and in vitro antimalarial activity (94-96) including quassinoids. Bruceantin has been most extensively studied, but is very cytotoxic however, other quassinoids are relatively less toxic to cultured KB cells while retaining potent antimalarial activity (88). Plants from the Meliaceae are commonly used as febrifuges in Africa, and several limonoids from this family, such as nimbolide and gedunin, have also been found to produce moderate inhibition of cultured P. falciparum (97,98). 

The isolation of a new jS-carboline alkaloid, l-acetyl-3-methoxycarbonyl-j8-carboline (10), from the leaves of Vestia lycioides Willd., constitutes the first reported occurrence of a /8-carboline derivative in the family Solanaceae. Several simple jS-carboline derivatives also occur in the bark and roots of Ailanthus malabarica DC. (fam. Simaroubaceae) these include 1-methoxy-carbonyl-j8 -carboline, 4-methoxy-1 -vinyl-/3 -carboline (dehydrocrenatine),... 

The third group of acetylenic compounds is not related clearly to the first two. Acetylenic linkages are occasionally introduced into compounds of diverse biosynthetic origin such as sesquiterpenes, tetraterpenes, and amino acids (Fig. 3.12). These compounds are found in unrelated plant families, among them the Annonaceae, Cupressaceae, Euphor-biaceae, Fabaceae, Lauraceae, Myoporaceae, Sapindaceae, Simaroubaceae, Sterculiaceae, Valerianaceae, and certain algae and mosses. 

Two major groups of metabolically altered tiiterpenes, the limonoids (tetranortriterpenoids) and the quassinoids (decanortriterpenoids) are derived from euphol (1) (Fig. 25.1) or tirucallol (2) (Fig. 25.2). To date, these compounds are restricted in distribution to the Rutaceae, Meliaceae, Cneora-ceae, Simaroubaceae, and, perhaps, the Burseraceae (Connolly and Hill, 1991), and occur variously in seeds, fruits, and wood of plants of these families. In general, the limonoid and quassinoid content of leaves has not been examined (Taylor, 1983). 

Quassinoids are decanortriterpenes known to occur only in the family Simaroubaceae (Polonsky, 1983, 1986). More than 120 compounds and 5 major structural types have been described (Polonsky, 1986). 

The family Rutaceae has been regarded by most system-atists as closely related to the Cneoraceae, Meliaceae, Ptaer-oxylaceae, and Simaroubaceae. Although alkaloids largely... 

---