Xanthonoid
Encyclopedia
A xanthonoid is a chemical natural phenol
ic compound formed from the xanthone
backbone. Many members of the Clusiaceae
contain xanthonoids.
Xanthonoid biosynthesis in cell cultures of Hypericum androsaemum
involves the presence of a benzophenone synthase
condensing a molecule of benzoyl-CoA
with three malonyl-CoA
yielding to 2,4,6-trihydroxybenzophenone. This intermediate is subsequently converted by a benzophenone 3′-hydroxylase, a cytochrome P450 monooxygenase, leading to the formation of 2,3′,4,6-tetrahydroxybenzophenone.
Some examples are tomentonone, zeyloxanthonone and calozeyloxanthone isolated from the bark of Calophyllum tomentosum
, apetalinone A, B, C and D from Calophyllum apetalum, gaudichaudione A, B, C, D, E, F, G, H, gaudichaudiic acid A, B, C, D, E, morellic acid and forbesione from Garcinia gaudichaudii, methylswertianin and bellidifolin from Swertia punicea
or psorospermin obtained from Psorospermum febrifugum. Cassiaxanthone can be found in Cassia reticulata.
Cytotoxic
xanthones (gambogin, morellin dimethyl acetal, isomoreollin B, moreollic acid, gambogenic acid, gambogenin, isogambogenin, desoxygambogenin, gambogenin dimethyl acetal, gambogellic acid, gambogic acid
, isomorellin, morellic acid, desoxymorellin and hanburin) can be isolated from the dry latex of Garcinia hanburyi
(gamboge tree).
Natural phenol
Natural phenols, bioavailable phenols, plant phenolics, low molecular weight phenols or phenoloids are a class of natural products. They are small molecules containing one or more phenolic group. These molecules are smaller in size than polyphenols, containing less than 12 phenolic groups...
ic compound formed from the xanthone
Xanthone
Xanthone is an organic compound with the molecular formula C13H8O2. It can be prepared by the heating of phenyl salicylate. In 1939, xanthone was introduced as an insecticide and it currently finds uses as ovicide for codling moth eggs and as a larvicide...
backbone. Many members of the Clusiaceae
Clusiaceae
The Clusiaceae or Guttiferae Juss. is a family of plants formerly including about 37 genera and 1610 species of trees and shrubs, often with milky sap and fruits or capsules for seeds. It is primarily tropical...
contain xanthonoids.
Xanthonoid biosynthesis in cell cultures of Hypericum androsaemum
Hypericum androsaemum
Hypericum androsaemum, commonly known as tutsan, is a plant in the genus Hypericum native to open woods and hillsides in Eurasia. It is a perennial shrub reaching up to 1.5 m in height.-Common name:...
involves the presence of a benzophenone synthase
Benzophenone synthase
In enzymology, a benzophenone synthase is an enzyme that catalyzes the chemical reactionThus, the two substrates of this enzyme are malonyl-CoA and 3-hydroxybenzoyl-CoA, whereas its 3 products are CoA, 2,3',4,6-tetrahydroxybenzophenone, and CO2....
condensing a molecule of benzoyl-CoA
Benzoyl-CoA
Benzoyl-CoA is a molecule implied in the activity of the different enzymes 4-hydroxybenzoyl-CoA reductase, benzoyl-CoA reductase, benzoyl-CoA 3-monooxygenase, benzoate-CoA ligase, 2alpha-hydroxytaxane 2-O-benzoyltransferase, anthranilate N-benzoyltransferase, biphenyl synthase, glycine...
with three malonyl-CoA
Malonyl-CoA
Malonyl-CoA is a coenzyme A derivative.-Functions:It plays a key role in chain elongation in fatty acid biosynthesis and polyketide biosynthesis....
yielding to 2,4,6-trihydroxybenzophenone. This intermediate is subsequently converted by a benzophenone 3′-hydroxylase, a cytochrome P450 monooxygenase, leading to the formation of 2,3′,4,6-tetrahydroxybenzophenone.
Some examples are tomentonone, zeyloxanthonone and calozeyloxanthone isolated from the bark of Calophyllum tomentosum
Calophyllum tomentosum
Calophyllum tomentosum is a species of flowering plant in the Calophyllaceae family, commonly known as 'bintangur'.It is found in Sri Lanka and the Western Ghats.-References:...
, apetalinone A, B, C and D from Calophyllum apetalum, gaudichaudione A, B, C, D, E, F, G, H, gaudichaudiic acid A, B, C, D, E, morellic acid and forbesione from Garcinia gaudichaudii, methylswertianin and bellidifolin from Swertia punicea
Swertia punicea
Swertia punicea is a plant species in the genus Swertia.The xanthonoids methylswertianin and bellidifolin can be isolated from S. punicea....
or psorospermin obtained from Psorospermum febrifugum. Cassiaxanthone can be found in Cassia reticulata.
Cytotoxic
Cytotoxicity
Cytotoxicity is the quality of being toxic to cells. Examples of toxic agents are a chemical substance, an immune cell or some types of venom .-Cell physiology:...
xanthones (gambogin, morellin dimethyl acetal, isomoreollin B, moreollic acid, gambogenic acid, gambogenin, isogambogenin, desoxygambogenin, gambogenin dimethyl acetal, gambogellic acid, gambogic acid
Gambogic acid
Gambogic acid is a xanthonoid that is derived from the brownish or orange resin from Garcinia hanburyi. This natural chemical has shown promising antitumor activity in clinical trials with mice. Garcinia hanburyi is a small to medium sized evergreen tree with smooth grey bark...
, isomorellin, morellic acid, desoxymorellin and hanburin) can be isolated from the dry latex of Garcinia hanburyi
Garcinia hanburyi
Garcinia hanburyi is a plant species in the genus Garcinia the gamboge trees.Names :* English : Hanbury's Garcinia, Gambojia, Gamboge, Indian Gamboge tree* Indian : Tamāla or Tamal* German : Gummi-gutti...
(gamboge tree).