Depside
Encyclopedia
A depside is a type of polyphenol
ic compound composed of two or more monocyclic aromatic
units linked by an ester
bond. Depsides are most often found in lichen
s, but have also been isolated from higher plants
, including species of the Ericaceae
, Lamiaceae
, Papaveraceae
and Myrtaceae
. Depsides have antibiotic
, anti-HIV
, antioxidant
, and anti-proliferative activity. As inhibitors of prostaglandin
synthesis and leukotriene B4
biosynthesis, depsides are potent non-steroidal anti-inflammatories
.
A depsidase is a type of enzyme that cuts depside bonds. One such enzyme is tannase
.
Gyrophoric acid
, found in the lichen Cryptothecia rubrocincta
, is a depside.
Polyphenol
Polyphenols are a structural class of natural, synthetic, and semisynthetic organic chemicals characterized by the presence of large multiples of phenol structural units...
ic compound composed of two or more monocyclic aromatic
Aromaticity
In organic chemistry, Aromaticity is a chemical property in which a conjugated ring of unsaturated bonds, lone pairs, or empty orbitals exhibit a stabilization stronger than would be expected by the stabilization of conjugation alone. The earliest use of the term was in an article by August...
units linked by an ester
Ester
Esters are chemical compounds derived by reacting an oxoacid with a hydroxyl compound such as an alcohol or phenol. Esters are usually derived from an inorganic acid or organic acid in which at least one -OH group is replaced by an -O-alkyl group, and most commonly from carboxylic acids and...
bond. Depsides are most often found in lichen
Lichen
Lichens are composite organisms consisting of a symbiotic organism composed of a fungus with a photosynthetic partner , usually either a green alga or cyanobacterium...
s, but have also been isolated from higher plants
Vascular plant
Vascular plants are those plants that have lignified tissues for conducting water, minerals, and photosynthetic products through the plant. Vascular plants include the clubmosses, Equisetum, ferns, gymnosperms and angiosperms...
, including species of the Ericaceae
Ericaceae
The Ericaceae, commonly known as the heath or heather family, is a group of mostly calcifuge flowering plants. The family is large, with roughly 4000 species spread across 126 genera, making it the 14th most speciose family of flowering plants...
, Lamiaceae
Lamiaceae
The mints, taxonomically known as Lamiaceae or Labiatae, are a family of flowering plants. They have traditionally been considered closely related to Verbenaceae, but in the 1990s, phylogenetic studies suggested that many genera classified in Verbenaceae belong instead in Lamiaceae...
, Papaveraceae
Papaveraceae
Papaveraceae, informally known as the poppy family, are an economically important family of 44 genera and approximately 770 species of flowering plants in the order Ranunculales. The family is cosmopolitan, occurring in temperate and subtropical climates, but almost unknown in the tropics...
and Myrtaceae
Myrtaceae
The Myrtaceae or Myrtle family are a family of dicotyledon plants, placed within the order Myrtales. Myrtle, clove, guava, feijoa, allspice, and eucalyptus belong here. All species are woody, with essential oils, and flower parts in multiples of four or five...
. Depsides have antibiotic
Antibiotic
An antibacterial is a compound or substance that kills or slows down the growth of bacteria.The term is often used synonymously with the term antibiotic; today, however, with increased knowledge of the causative agents of various infectious diseases, antibiotic has come to denote a broader range of...
, anti-HIV
HIV
Human immunodeficiency virus is a lentivirus that causes acquired immunodeficiency syndrome , a condition in humans in which progressive failure of the immune system allows life-threatening opportunistic infections and cancers to thrive...
, antioxidant
Antioxidant
An antioxidant is a molecule capable of inhibiting the oxidation of other molecules. Oxidation is a chemical reaction that transfers electrons or hydrogen from a substance to an oxidizing agent. Oxidation reactions can produce free radicals. In turn, these radicals can start chain reactions. When...
, and anti-proliferative activity. As inhibitors of prostaglandin
Prostaglandin
A prostaglandin is any member of a group of lipid compounds that are derived enzymatically from fatty acids and have important functions in the animal body. Every prostaglandin contains 20 carbon atoms, including a 5-carbon ring....
synthesis and leukotriene B4
Leukotriene B4
Leukotriene B4 is a leukotriene involved in inflammation. It is produced from leukocytes in response to inflammatory mediators and is able to induce the adhesion and activation of leukocytes on the endothelium, allowing them to bind to and cross it into the tissue...
biosynthesis, depsides are potent non-steroidal anti-inflammatories
Non-steroidal anti-inflammatory drug
Nonsteroidal anti-inflammatory drugs, usually abbreviated to NSAIDs or NAIDs, but also referred to as nonsteroidal anti-inflammatory agents/analgesics or nonsteroidal Anti-inflammatory medicines , are drugs with analgesic and antipyretic effects and which have, in higher doses, anti-inflammatory...
.
A depsidase is a type of enzyme that cuts depside bonds. One such enzyme is tannase
Tannase
In enzymology, a tannase is an enzyme that catalyzes the chemical reactionThus, the two substrates of this enzyme are digallate and H2O, whereas its product is gallate....
.
Gyrophoric acid
Gyrophoric acid
Gyrophoric acid is a depside that can be found in the lichen Cryptothecia rubrocincta and in Xanthoparmelia pokomyi....
, found in the lichen Cryptothecia rubrocincta
Cryptothecia rubrocincta
Cryptothecia rubrocincta is a species of lichen in the Arthoniaceae family of fungi. The species is distributed in subtropical and tropical locations throughout the southeastern United States, as well as Central and South America, and has been collected infrequently in a few locales in Africa...
, is a depside.