Simaroubaceae species

Figure 5 Biological activities associated with quassinoids, from Simaroubaceae species, may not be linked to a common mechanism of action/ Different testing procedures have indicated insecticidal activity for quassin, anticancer activity for quassimarin (also present in Quassia amara) and antimalarial activity for simalikalactone-D/...

Until 1985 only three quassinoids with Cis skeleton had been isolated from Simaroubaceae species, Samaderine A (5) isolated from Samadera indica [7], and laurycolactone A (6) and B (7) isolated from Eurycoma longifolia Jack [8],... 

Two decades passed and twenty-three more quassinoids were isolated from Simaroubaceae species in a total of thirty-two quassinoids with C19 skeleton identified so far. 

The eight new quassinoids C19 type shinjulactone B (19) with a presence of a l,2-seco-l-nor-(5->10)-a >eo-picrasan-2,5-olide skeleton have been isolated from Simaroubaceae species. 

To proceed, they are striped, all quassinoids identified since the year of 1985 up to 2003. The identified quassinoids are divided by Simaroubaceae species. 

Under the name of quassia or quassia wood Quassiae lignum), two indiscriminate species were then sold in Europe Quassia amara (mainly root, wood and stems) and Picrasma excelsa (Sw.) Planch, (formerly Picraena excelsa (Sw.) Lindley) or Jamaican quassia (trunk wood) [17,18, 20]. Quassia wood was initially used as an antiseptic, for meat preservation and as antipyretic. But because of its bitter principles its main recommendation was as a digestive and tonic [17, 21]. Q. amara was rapidly registered in various European pharmacopoeias, alone or with other Simaroubaceae species with the same reputation, such as Picrasma excelsa or Simarouba amara Aubl. [22-25]. The reputation of quassia wood then spread to the United States, where the medicinal use of cups mostly made of Q. amara wood became popular [26]. Meanwhile, a few Simaroubaceae were registered in North American official pharmaceutical documents, such as the King s American Dispensatory [27] or the United States Dispensatory [28]. 

Table 125.2 Medicinal uses of Simaroubaceae species (Part of plant used AP aereal part, Bd bud. Ft fruit, L leaf, Bk bark, RBk root bark, R root. Res resin, 5 seed, SBk Stem bark. ...

Lastly, three Simaroubaceae species are described as antivenom Brucea antidysenterica. Quassia amara, and Simaba cedron, with a veiy strong convergence of use for the cotyledons of Simaba cedron seeds in South America). Brucea antidysenterica, Brucea javanica, Eurycoma longifolia. Quassia undulata, and Picrasma javanica are known as antidotes to food poisoning or other types poisoning. Central nervous system troubles, such as dementia, nervousness, and epilepsy, and alcohol addiction are treated with preparations of Ailanthus altissima. Quassia undulata, Simarouba amara, or Picrasma excelsa. 

Methoxycanthin-6-one (7) has been found in the bark (stem, root, branch, and sapling) and leaves of Pentaceras australis (35). This compound has also been found in three species of Rutaceae including P. australis, five species of Simaroubaceae, and one species of Caryophyl-laceae. The number of species of plants containing 7 is second only to those containing 1. Readers are referred to Volume 3 (p. 249) of this treatise for its structure (5). 

Only two species of Simaroubaceae plants are known in Japan, namely P. ailanthoides described above, and Ailanthus altissima. The former plant grows wild in Japan, whereas the latter plant is a deciduous ornamental tree native to China that was imported into Japan at the end of the nineteenth century. This tree is known as Tree of Heaven, meaning that this tree grows very fast to be able to touch heaven quickly. Canthin-6-one alkaloids isolated from Simaroubaceae plants were reviewed by Ohmoto and Zasshi [5]. 

A species of enigmatic affinities, Harrisonia abyssinica, usually placed in the Simaroubaceae (but see the discussion above), contains both the widespread limonoid bitter principle, obacunone (47) and a second limonoid, harrisonin (48). Harrisonin has insect antifeedant activity, is cytotoxic, and has antibacterial activity. This compound inhibits feeding... 

Canthin-6-one (30) and a series of related alkaloids are found in one species of Pentaceras, several species of Zanthoxylum (Rutaceae), and several species of the Simaroubaceae (Fig. 35.9) (Waterman and Khalid, 1981). These alkaloids also have been reported from the Malvaceae, Caryophyllaceae, and Amaranthaceae (Tillequin, 1993). Similar compounds... 

The history of quassinoids began in the mid-eighteenth century, after the discovery in 1760 of the febrifuge properties of a Simaroubaceae, Quassia amara L. (Fig. 125.5). The medicinal property of the roots of this species was revealed to Carl G. Dahlberg, a Dutch army officer, by a Suriname slave and famous healer named Kwasi. This recipe was subsequently made public by Daniel Rolander, a Swedish naturalist. Linnaeus, excited by the discovery of this plant and its uses, named it in honor of the healer. The botanist, however, committed an error in its description, corrected in 1763 by his disciple C.M. Blom [17-20]. 

Studies based on traditional use of Simaroubaceae continued in the 1980s, especially by Phillipson et al. [63-67]. Many articles rai this subject followed, with, for example, the reisolation of simalikalactone D and the isolation and characterization of gutolactone from the bark of Simaba guianensis Aubl., a species used by people in the Amazon Basin [68]. Also, cedronin was isolated from the bark of Simaba cedron, a species used in Central and South America for the treatment of malaria [69], and samaderines B, E, X, and Z were isolated from Quassia indica branches used in the Indonesian traditional pharmacopeia [70]. In our work, it was chosen to test the traditional remedies as prepared by local people. This approach highlighted the remarkable activity of a decoction made from the... 

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]. 

Deoxygenated products have a restricted distribution. Acridone itself (1) was isolated from Toddalia acukata (97) and Thamnosma montana (98), which also contains 10-methylacridone (30) (99, 100). Alkaloids lacking oxygenated substitution at C-3 include 1-hydroxyacridone, 1,7-dihydroxyacridone, and 1,8-dihydroxyacridone derivatives. It should be noted that 1-methoxy-10-methylacridone (31) and 1,8-dihydroxyacridone (32) were isolated from Samadera aff. bidwillii, the only species of the Simaroubaceae which has afforded this type of secondary metabolite (101). 

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

Martiriol and a few other non-halogenated cyclic ethers have also been identified in several species of Laurenda. The first to have been isolated is teurilene, a tricyclic squalenoid from a Japanese variety of Laurenda obtusa (Suzuki et al., 1985).It is a meso compotmd, optically inactive by internal symmetry, and strongly cytotoxic with an ED50 of 0.18 pgml against leukemia P-388. A compound very similar to the latter, emylene, was discovered later in a plant of the family Simaroubaceae, Eurycoma longifolia (Morita et al., 1993). 

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