Ardisiaquinones are a group of closely-related chemical compounds found in plants in the genus ''

Ardisia ''Ardisia'' (coralberry or marlberry) is a genus of flowering plants in the family Primulaceae. It was in the former Myrsinaceae family now recognised as the myrsine sub-family Myrsinoideae. They are distributed in the Americas, Asia, Australia, ...

''. The first examples, ardisiaquinones A-C, were isolated in 1968 from ''

Ardisia sieboldii ''Ardisia'' (coralberry or marlberry) is a genus of flowering plants in the family Primulaceae. It was in the former Myrsinaceae family now recognised as the myrsine sub-family Myrsinoideae. They are distributed in the Americas, Asia, Australia ...

''. In 1995, ardisiaquinones D, E, and F were discovered, also from ''Ardisia sieboldii''. In 2001, ardisiaquinones G, H and I were isolated from ''

Ardisia teysmanniana ''Ardisia'' (coralberry or marlberry) is a genus of flowering plants in the family Primulaceae. It was in the former Myrsinaceae family now recognised as the myrsine sub-family Myrsinoideae. They are distributed in the Americas, Asia, Australia ...

''. Chemically, the ardisiaquinones consist of two variably-substituted

1,4-benzoquinone 1,4-Benzoquinone, commonly known as ''para''-quinone, is a chemical compound with the formula C6H4O2. In a pure state, it forms bright-yellow crystals with a characteristic irritating odor, resembling that of chlorine, bleach, and hot plastic o ...

units connected by a long

alkyl In organic chemistry, an alkyl group is an alkane missing one hydrogen. The term ''alkyl'' is intentionally unspecific to include many possible substitutions. An acyclic alkyl has the general formula of . A cycloalkyl is derived from a cycloalk ...

alkenyl In organic chemistry, an alkene is a hydrocarbon containing a carbon–carbon double bond. Alkene is often used as synonym of olefin, that is, any hydrocarbon containing one or more double bonds.H. Stephen Stoker (2015): General, Organic, an ...

chain.

Research

Ardisiaquinones are of research interest because they possess 5-lipoxygenase (5-LOX) inhibitor activity and 5-LOX has clinical relevance in inflammation. For example, ardisiaquinone A protects against liver injury in an animal model of ischemia-reperfusion injury. Likewise, ardisiaquinone G has also shown 5-LOX inhibition. Ardisiaquinone A has also been shown to have an antiallergic effect in an animal model. Other ardisiaquinones have shown antiproliferative and antimicrobial effects ''

in vitro ''In vitro'' (meaning in glass, or ''in the glass'') studies are performed with microorganisms, cells, or biological molecules outside their normal biological context. Colloquially called "test-tube experiments", these studies in biology an ...

''. Laboratory syntheses of ardisiaquinones A and B have been reported.

Chemical structures

File:Ardisiaquinone A.svg, Ardisiaquinone A File:Ardisiaquinone B.svg, Ardisiaquinone B File:Ardisiaquinone C.svg, Ardisiaquinone C File:Ardisiaquinone D.svg, Ardisiaquinone D File:Ardisiaquinone E.svg, Ardisiaquinone E File:Ardisiaquinone F.svg, Ardisiaquinone F File:Ardisiaquinone G.svg, Ardisiaquinone G

References

{{reflist Benzoquinones Ardisia