
Quassinoids are degraded
triterpene
Triterpenes are a class of terpenes composed of six isoprene units with the molecular formula C30H48; they may also be thought of as consisting of three terpene units. Animals, plants and fungi all produce triterpenes, including squalene, the pre ...
lactones (similar to
limonoids
Limonoids are phytochemicals of the triterpenoid class which are abundant in sweet or sour-scented citrus fruit and other plants of the families Cucurbitaceae, Rutaceae, and Meliaceae. Certain limonoids are antifeedants such as azadirachtin from ...
) of the
Simaroubaceae
The Simaroubaceae, also known as the quassia family, 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 phyloge ...
plant family grouped into C-18, C-19, C-20, C-22 and C-25 types. The prototypical member of the group,
quassin, was first described in the 19th century from plants of the genus ''
Quassia
''Quassia'' ( or ) 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 ...
'' from which it gets its name. It was isolated in 1937, and its structure elucidated in 1961.
Sources
More than 200 currently-known quassinoids have been isolated and identified from various species of simaroubaceae family.
Quassinoids can also be extracted from various Simaroubaceae family species such as; ''
Ailanthus excelsa
''Ailanthus excelsa'', commonly known as tree of heaven, is a large deciduous tree found in India and Sri Lanka. In Tamil, it is also known as Pi-Nari Maram due to its disagreeable odor. The trees are grown along the edges of fields and rivers to ...
'', ''
Ailanthus vilmoriniana
''Ailanthus vilmoriniana'', commonly known as downy tree of heaven, is a tree in the quassia family. It is native to western China, but is occasionally encountered in northern European gardens.
Description
''Ailanthus vilmoriniana'' is a tree ...
'', (the fruits of) ''
Brucea javanica'', ''
Hannoa klaineana'',
''
Pierreodendron kerstingii
''Pierreodendron kerstingii'' is a species of tree in the family Simaroubaceae. It is endemic to West Africa and found in Ivory Coast, Ghana, Togo, and Benin. It is sometimes considered synonym of ''Pierreodendron africanum'', which would then be ...
'',
''
Quassia africana
''Quassia'' ( or ) 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 ...
'',
''
Quassia amara
''Quassia amara'', also known as amargo, bitter-ash, bitterwood, or hombre grande (spanish language, spanish for ''big man'') is a species in the genus ''Quassia'', with some botanists treating it as the sole species in the genus. The genus was na ...
'',
(the wood of ) ''
Picrasma ailanthoides'',
''
Picrasma javanica'', ''
Picrolemma pseudocoffea'', ''
Simaba guianensis
''Simaba'' is a genus of flowering plants belonging to the family Simaroubaceae.
Its native range stretches from southern tropical America and Trinidad, across to western tropical Africa to Angola then across to western Malesia.
It was first pu ...
'', and ''
Simaruba glauca''.
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).
Uses
They are a biologically potent class of natural products, possessing
antimalarial
Antimalarial medications or simply antimalarials are a type of antiparasitic chemical agent, often naturally derived, that can be used to treat or to prevent malaria, in the latter case, most often aiming at two susceptible target groups, young ...
,
antifeedant
Antifeedants are organic compounds produced by plants to repel herbivores through distaste or toxicity. These chemical compounds are typically classified as secondary metabolites in that they are not essential for the metabolism of the plant, but ...
, insecticidal, anti-inflammatory, and anticancer (or anti-leukemic)
properties. The quassinoid bruceantin reached two separate phase II clinical trials in 1982 and 1983.
Other quassinoids include:
*
Bruceanols
*
Bruceolide
*
Eurycomanone
*
Gutolactone
Gutolactone is a chemical compound extracted from '' Simaba guianensis'' and it has displayed antimalarial properties ''in vitro
''In vitro'' (meaning ''in glass'', or ''in the glass'') Research, studies are performed with Cell (biology), cel ...
*
Isobrucein A
*
Neoquassin
*
Nigakihemiacetal A
*
Odyendanol
*
Picrasinol D[
* Quassimarin
* Samaderines
* Simalikalactones (including simalikalactones A, B, C,] simalikalactone D, and simalikalactone E)
References
Other sources
* Z. Guo, S. Vangapandu, R.W. Sindelar, L.A. Walker, R.D. Sindelar., Biologically active quassinoids and their chemistry: potential leads for drug design, Frontier. Med. Chem., 4 (2009), pp. 285-308
External links
*
* {{wiktionary inline, quassinoid
Heterocyclic compounds with 4 rings
Methoxy compounds