Quassinoids are degraded triterpene lactones (similar to limonoids) of the Simaroubaceae plant family grouped into C-18, C-19, C-20, C-22 and C-25 types. [1] The prototypical member of the group, quassin, was first described in the 19th century from plants of the genus Quassia from which it gets its name. [2] It was isolated in 1937, [3] and its structure elucidated in 1961. [4]
More than 200 currently-known quassinoids have been isolated and identified from various species of simaroubaceae family. [5]
Quassinoids can also be extracted from various Simaroubaceae family species such as; Ailanthus excelsa , [6] Ailanthus vilmoriniana , [7] (the fruits of) Brucea javanica , [8] Hannoa klaineana , [9] [10] Pierreodendron kerstingii , [11] Quassia africana , [12] [13] Quassia amara , [14] [15] (the wood of ) Picrasma ailanthoides , [16] Picrasma javanica , [17] Picrolemma pseudocoffea , [18] Simaba guianensis , [19] and Simaruba glauca . [20]
They are found in species from American and West African genera (belonging mainly to the tribe Simaroubeae) and from the East African and Asian genera (belonging mainly to Picrasmeae and Soulameae tribes). [21]
They are a biologically potent class of natural products, possessing antimalarial, [15] [22] antifeedant, [23] insecticidal, [24] anti-inflammatory, [25] and anticancer (or anti-leukemic) [11] [26] [27] properties. The quassinoid bruceantin reached two separate phase II clinical trials in 1982 [28] and 1983. [29]
Other quassinoids include: [30]
Quassia is a plant genus in the family Simaroubaceae. Its size is disputed; some botanists treat it as consisting of only one species, Quassia amara from tropical South America, while others treat it in a wide circumscription as a pantropical genus containing up to 40 species of trees and shrubs.
Quassin is a white, bitter, crystalline substance that is the prototypical example of the family of quassinoids. It can be extracted from the quassia tree, from which it gets its name. It was first isolated in 1937, and its chemical structure was elucidated in 1961. XIX
The Simaroubaceae are a small, mostly tropical, family in the order Sapindales. In recent decades, it has been subject to much taxonomic debate, with several small families being split off. A molecular phylogeny of the family was published in 2007, greatly clarifying relationships within the family. Together with chemical characteristics such as the occurrence of petroselinic acid in Picrasma, in contrast to other members of the family such as Ailanthus, this indicates the existence of a subgroup in the family with Picrasma, Holacantha, and Castela.
Quassia amara, also known as amargo, bitter-ash, bitter-wood, or hombre grande is a species in the genus Quassia, with some botanists treating it as the sole species in the genus. The genus was named by Carl Linnaeus who named it after the first botanist to describe it: the Surinamese freedman Graman Quassi. Q. amara is used as insecticide, in traditional medicine and as additive in the food industry.
Phenanthrenoids are chemical compounds formed with a phenanthrene backbone. These compounds occur naturally in plants, although they can also be synthesized.
Hannoa is a genus of plant in the family Simaroubaceae. Found in tropical parts of Africa.
A depside is a type of polyphenolic compound composed of two or more monocyclic aromatic units linked by an ester group. Depsides are most often found in lichens, but have also been isolated from higher plants, including species of the Ericaceae, Lamiaceae, Papaveraceae and Myrtaceae.
Prodelphinidin is a name for the polymeric tannins composed of gallocatechin. It yields delphinidin during depolymerisation under oxidative conditions.
Ergosterol peroxide (5α,8α-epidioxy-22E-ergosta-6,22-dien-3β-ol) is a steroid derivative. It has been isolated from a variety of fungi, yeast, lichens and sponges, and has been reported to exhibit immunosuppressive, anti-inflammatory, antiviral, trypanocidal and antitumor activities in vitro.
Amentoflavone is a biflavonoid constituent of a number of plants including Ginkgo biloba, Chamaecyparis obtusa (hinoki), Biophytum sensitivum, Selaginella tamariscina, Hypericum perforatum and Xerophyta plicata.
Patuletin is an O-methylated flavonol. It can be found in the genus Eriocaulon.
Simarouba amara is a species of tree in the family Simaroubaceae, found in the rainforests and savannahs of South and Central America and the Caribbean. It was first described by Aubl. in French Guiana in 1775 and is one of six species of Simarouba. The tree is evergreen, but produces a new set of leaves once a year. It requires relatively high levels of light to grow and grows rapidly in these conditions, but lives for a relatively short time. In Panama, it flowers during the dry season in February and March, whereas in Costa Rica, where there is no dry season it flowers later, between March and July. As the species is dioecious, the trees are either male or female and only produce male or female flowers. The small yellow flowers are thought to be pollinated by insects, the resulting fruits are dispersed by animals including monkeys, birds and fruit-eating bats and the seeds are also dispersed by leaf cutter ants.
Simarouba is a genus of trees and shrubs in the family Simaroubaceae, native to the neotropics. It has been grouped in the subtribe Simaroubina along with the Simaba and Quassia genera. They have compound leaves, with between 1 and 12 pairs of alternate pinnate leaflets. Their flowers are unisexual, relatively small and arranged in large panicles. Plants are dioecious, bearing only male or female flowers. The individual flowers have between 4 and 6 sepals and petals and between 8 and 12 stamens. The fruit is a carpophore and has up to 5 drupaceous mericarps.
Astringin is a stilbenoid, the 3-β-D-glucoside of piceatannol. It can be found in the bark of Picea sitchensis and Picea abies.
Dihydrostilbenoids (bibenzyls) are natural phenols formed from the dihydrostilbene (bibenzyl) backbone.
Castela emoryi, with the common names crucifixion thorn, Emory's crucifixion-thorn, and Spanish: chaparro amargosa, is a shrub species in the genus Castela of the family Simaroubaceae.
Tabernaemontanine is a naturally occurring monoterpene indole alkaloid found in several species in the genus Tabernaemontana including Tabernaemontana divaricata.
Samadera is a genus of trees belonging to the family Simaroubaceae, in the order Sapindales. The genus is native to eastern Africa (Tanzania), across to parts of tropical Asia and parts of eastern Australia.
Ferroquine is a synthetic compound related to chloroquine which acts as an antimalarial, and shows good activity against chloroquine-resistant strains. It contains an organometallic ferrocene ring which is unusual in pharmaceuticals, and while it was first reported in 1997, it has progressed slowly through clinical trials, with results from Phase II trials showing reasonable safety and efficacy, and further trials ongoing.
Samadera indica, the bitter wood or Niepa bark tree, is a species of plant in the family Simaroubaceae. It is a shrub or tree and grows primarily in wet tropical regions, from west Africa, through India, then down through Indonesia to Malesia.
Media related to quassinoids at Wikimedia Commons
The dictionary definition of quassinoid at Wiktionary