
A xanthonoid is a chemical
natural phenol
In biochemistry, naturally occurring phenols are natural products containing at least one phenol functional group. Phenolic compounds are produced by plants and microorganisms. Organisms sometimes synthesize phenolic compounds in response to eco ...
ic compound formed from the
xanthone
Xanthone is an organic compound with the molecular formula O 6H4sub>2CO. It is a white solid.
In 1939, xanthone was introduced as an insecticide and it currently finds uses as ovicide for codling moth eggs and as a larvicide. Xanthone is also ...
backbone. Many members of the
Clusiaceae
The Clusiaceae or Guttiferae Juss. (1789) (''nom. alt. et cons.'' = alternative and valid name) are a family of plants including 13 genera and ca 750 species. Several former members of Clusiacae are now placed in Calophyllaceae and Hypericacea ...
contain xanthonoids.
Xanthonoid biosynthesis in cell cultures of ''
Hypericum androsaemum'' involves the presence of a
benzophenone synthase condensing a molecule of
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
In enzymology, a 2al ...
with three
malonyl-CoA
Malonyl-CoA is a coenzyme A derivative of malonic acid.
Functions
It plays a key role in chain elongation in fatty acid biosynthesis and polyketide biosynthesis.
Fatty acid biosynthesis
Malonyl-CoA provides 2-carbon units to fatty acids and com ...
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'' is a species of flowering plant in the family Calophyllaceae, commonly known as bintangur. It is found in Sri Lanka
Sri Lanka (, ; si, ශ්රී ලංකා, Śrī Laṅkā, translit-std=ISO (); ta, � ...
'',
apetalinone A,
B,
C and
D from ''
Calophyllum apetalum
''Calophyllum'' is a genus of tropical flowering plants in the family Calophyllaceae. They are mainly distributed in Asia, with some species in Africa, the Americas, Australasia, and the Pacific Islands.
History
Members of the genus ''Ca ...
'',
gaudichaudione A,
B,
C,
D,
E,
F,
G,
H,
gaudichaudiic acid A,
B,
C,
D,
E,
morellic acid and
forbesione from ''
Garcinia gaudichaudii
''Garcinia morella'' is a species of tree in the family Clusiaceae found in India, and Sri Lanka.
Common names
*Assamese: Kũzi Thekera (কুঁঁজী ঠেকেৰা)
* English: ''gamboge'' (Sri Lanka), ''gamboge'' ( India)
*Tamil: '' ...
'',
methylswertianin and
bellidifolin from ''
Swertia punicea'' or
psorospermin obtained from ''
Psorospermum febrifugum''.
Cassiaxanthone can be found in ''
Cassia reticulata''.
Cytotoxic
Cytotoxicity is the quality of being toxic to cells. Examples of toxic agents are an immune cell or some types of venom, e.g. from the puff adder (''Bitis arietans'') or brown recluse spider (''Loxosceles reclusa'').
Cell physiology
Treating ...
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).
[Cytotoxic xanthones from Garcinia hanburyi. Jun Asano, Kazuhiro Chiba, Masahiro Tada and Takao Yoshii, Phytochemistry, Volume 41, Issue 3, February 1996, Pages 815-820, ]
References
{{xanthonoid
Xanthonoids
Secondary metabolites